[go: up one dir, main page]

WO2012128233A1 - Composition colorée pour filtres de couleurs, et filtres de couleurs - Google Patents

Composition colorée pour filtres de couleurs, et filtres de couleurs Download PDF

Info

Publication number
WO2012128233A1
WO2012128233A1 PCT/JP2012/056945 JP2012056945W WO2012128233A1 WO 2012128233 A1 WO2012128233 A1 WO 2012128233A1 JP 2012056945 W JP2012056945 W JP 2012056945W WO 2012128233 A1 WO2012128233 A1 WO 2012128233A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituent
substituted
colorant
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2012/056945
Other languages
English (en)
Japanese (ja)
Inventor
裕介 飯田
美幸 平佐
昌平 坂本
理人 伊藤
北村　健一
英範 皆嶋
清水　宏明
秀一 木村
貫 岩田
俊啓 吉沢
深雪 田中
三上　譲司
鈴木　雄太
中村　高士
由昌 宮沢
須田　康政
西田　和史
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toyochem Co Ltd
Artience Co Ltd
Original Assignee
Toyo Ink SC Holdings Co Ltd
Toyochem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2011093515A external-priority patent/JP4993026B1/ja
Priority claimed from JP2011118726A external-priority patent/JP5782834B2/ja
Priority claimed from JP2011156970A external-priority patent/JP5982657B2/ja
Application filed by Toyo Ink SC Holdings Co Ltd, Toyochem Co Ltd filed Critical Toyo Ink SC Holdings Co Ltd
Priority to KR1020137027447A priority Critical patent/KR101550427B1/ko
Priority to CN201280013839.8A priority patent/CN103460086B/zh
Publication of WO2012128233A1 publication Critical patent/WO2012128233A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B25/00—Quinophthalones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators

Definitions

  • the present invention relates to a color liquid crystal display device, a color filter colorant used in the production of a color filter used for a color image pickup tube element, a color composition, and a color filter formed using the same. .
  • liquid crystal display device In the liquid crystal display device, a liquid crystal layer sandwiched between two polarizing plates controls the amount of light passing through the first polarizing plate by controlling the degree of polarization of light passing through the first polarizing plate.
  • the type using twisted nematic (TN) type liquid crystal is the mainstream.
  • a liquid crystal display device is capable of color display by providing a color filter between two polarizing plates, and has recently been used in televisions, personal computer monitors, and the like. The demand for higher brightness and higher color reproducibility is increasing.
  • a color filter has two or more kinds of fine band (striped) filter segments arranged in parallel or intersecting on the surface of a transparent substrate such as glass, or the fine filter segments are arranged vertically and horizontally. It is made up of those arranged in In general, it is often formed by three-color filter segments of red, green, and blue. Each segment is as fine as several microns to several hundreds of microns, and is arranged regularly in a predetermined arrangement for each hue. .
  • a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon.
  • the formation thereof must generally be performed at a high temperature of 200 ° C. or higher, preferably 230 ° C. or higher. For this reason, it is required to use a colorant having excellent heat resistance and light resistance in the production of a color filter.
  • a quinophthalone compound is known as a pigment dispersant for stabilizing the dispersion of Pigment Yellow 138.
  • Patent Document 1 discloses a quinophthalone compound containing a sulfonic acid
  • Patent Document 2 discloses a quinophthalone compound to which a phthalimidomethyl group is added.
  • Patent Document 3 discloses a quinophthalone compound starting from the following compound (1) as a pigment composition with improved dispersion stability over time.
  • Patent Document 4 describes that a pigment composition excellent in coloring power, sharpness, and the like can be obtained by using a compound in which a quinophthalone structure is dimerized.
  • Patent Document 5 discloses a quinophthalone compound having a naphthalene ring for coloring a polymer material. However, all of these quinophthalone compounds are for the purpose of coloring plastics, and their suitability for color filter applications is unknown.
  • Patent Documents 6 to 12 It is also known to use an aluminum phthalocyanine pigment as a coloring composition for a green color filter segment.
  • an aluminum phthalocyanine pigment it is necessary to use a yellow pigment in combination.
  • the conventional quinophthalone compound known as a yellow pigment has the above-mentioned problems, when these are used in combination, the contrast ratio and coloring power of the color filter are not sufficient.
  • the pigment contained in the filter segment is subjected to a fine processing.
  • the pigment whose primary particles or secondary particles have been miniaturized generally tends to aggregate and it is very difficult to obtain a stable coloring composition even if it is intended to stabilize. there were.
  • a finely-treated pigment is difficult to stably disperse in a pigment carrier at a high concentration and causes various problems with respect to the production process and the product itself.
  • a pigment dispersant is used in order to maintain a good dispersion state.
  • the pigment dispersant has both a structure that adsorbs to the pigment and a structure that has a high affinity for the solvent that is the dispersion medium, and the performance is determined by the balance between these two parts.
  • Various pigment dispersants are used in accordance with the surface state of the pigment to be dispersed.
  • pigments having an acid-biased surface have basic functional groups having electrostatic adsorption.
  • a dispersant is used. In this case, the basic functional group serves as a pigment adsorption site.
  • Patent Documents 13 to 17 Examples of using a basic pigment dispersant having an amino group as a basic functional group in a coloring composition for a color filter are described in Patent Documents 13 to 17, for example. However, although they have a certain degree of dispersion ability, it has not been possible to stabilize the dispersion of pigments that have been subjected to ultrafine processing, which is desired to be used for high contrast, as a color filter coloring composition. .
  • Patent Document 18 A composition has been proposed (Patent Document 18).
  • a voltage holding ratio can be given as an index representing the display performance of the liquid crystal display device.
  • Liquid crystal is an extremely high insulating material, and when the polar compound remaining in the color filter coloring composition elutes into the liquid crystal cell, the voltage between the electrodes decreases, leading to a decrease in voltage holding ratio, and display unevenness. Generation
  • Patent Documents 19 to 21 propose green coloring compositions for color filters containing phthalocyanine dyes having various structures and quinophthalone dyes.
  • these green coloring compositions for color filters have problems of insufficient lightness and poor heat resistance and light resistance.
  • Patent Document 22 proposes a green coloring composition for a color filter containing a zinc phthalocyanine pigment and a quinophthalone dye as a means for improving brightness.
  • zinc phthalocyanine-based pigments have high acidity and are easily extracted into the liquid crystal phase laminated on the color filter layer, leading to a decrease in voltage holding ratio, resulting in display unevenness and poor alignment.
  • An embodiment of the present invention relates to a color composition for a color filter, comprising a colorant, a binder resin, and a solvent, wherein the colorant contains a colorant represented by the general formula (1).
  • R 1 to R 13 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or a substituent.
  • the sulfamoyl group which may have a group is shown.
  • the adjacent groups of R 1 to R 4 and / or R 10 to R 13 together form an aromatic ring which may have a substituent. That is, at least one adjacent set of groups out of R 1 to R 4 and / or at least one adjacent set of groups out of R 10 to R 13 are combined to have a substituent.
  • An aromatic ring that may be formed is formed.
  • the colorant represented by the general formula (1) is preferably a colorant selected from the general formulas (1A) to (1C).
  • R 14 to R 28 , R 29 to R 43 , and R 44 to R 60 are each independently: a hydrogen atom; a halogen atom; A good alkyl group; an alkoxyl group that may have a substituent; an aryl group that may have a substituent; —SO 3 H, —COOH, and monovalent to trivalent metal salts of these acidic groups; A salt; an optionally substituted phthalimidomethyl group; or an optionally substituted sulfamoyl group.
  • the colorant may further contain a colorant selected from general formulas (8A) and (8B).
  • X 1 to X 4 may each independently have an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • Y 1 to Y 4 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • Z represents a hydroxyl group, a chlorine atom, —OP ( ⁇ O) R 1 R 2 , or —O—SiR 3 R 4 R 5 .
  • R 1 to R 5 are each independently a hydrogen atom, a hydroxyl group, an alkyl group that may have a substituent, an aryl group that may have a substituent, an alkoxyl group that may have a substituent, or It represents an aryloxy group which may have a substituent, and Rs may be bonded to each other to form a ring.
  • n 1 to m 4 and n 1 to n 4 each independently represent an integer of 0 to 4, and m 1 + n 1 , m 2 + n 2 , m 3 + n 3 , m 4 + n 4 are each 0 to 4 may be the same or different.
  • X 5 to X 12 may each independently have an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • Y 5 to Y 12 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • L represents —O—SiR 6 R 7 —O—, —O—SiR 6 R 7 —O—SiR 8 R 9 —O—, or —O—P ( ⁇ O) R 10 —O—
  • R 6 to R 10 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, or a substituent.
  • the aryloxy group which may have a group is represented.
  • n 5 to m 12 and n 5 to n 12 each independently represent an integer of 0 to 4, and m 5 + n 5 , m 6 + n 6 , m 7 + n 7 , m 8 + n 8 , m 9 + n 9 , m 10 + n 10 , m 11 + n 11 , and m 12 + n 12 are each 0 to 4, and may be the same or different.
  • the colorant may further contain a dispersant.
  • the dispersant is a urethane prepolymer having isocyanate groups at both ends, obtained by reacting the hydroxyl group of the vinyl polymer (A) having two hydroxyl groups in one terminal region with the isocyanate group of diisocyanate (B).
  • a pigment dispersant obtained by reacting the isocyanate group of (E) with a primary and / or secondary amino group of an amine compound containing at least a polyamine (C), wherein the vinyl polymer (A) is ethylene oxide.
  • An ethylenically unsaturated monomer (a1) having at least one of a chain or a propylene oxide chain may be included in the copolymer composition.
  • the colorant may further contain a colorant represented by the general formula (6).
  • R 1 to R 6 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, Or, -O-R 7 is represented.
  • R 7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 1 to R 6 are not all hydrogen atoms.
  • embodiment of this invention contains a coloring agent, binder resin, and a solvent, and the said coloring agent contains the coloring agent represented by General formula (6),
  • the coloring composition for color filters characterized by the above-mentioned.
  • the colorant may further contain a colorant selected from general formulas (8A) and (8B).
  • the colorant may further contain a colorant represented by the general formula (7).
  • R 1 to R 6 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group. Or represents —O—R 11 .
  • R 11 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 7 to R 10 are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group, carboxyl group, substituted or unsubstituted And a sulfoamide group, a substituted or unsubstituted heterocyclic residue, —SR 12 , —O—R 12 , or —COO—R 12 .
  • R 12 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • an embodiment of the present invention contains a colorant, a binder resin, and a solvent, and the colorant contains a colorant represented by the general formula (7A). Related to things.
  • the colorant represented by the general formula (7A) may be a colorant represented by the general formula (7B).
  • R 1 to R 6 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group. Or represents —O—R 11 .
  • R 11 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 7 to R 10 are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group, carboxyl group, substituted or unsubstituted And a sulfoamide group, a substituted or unsubstituted heterocyclic residue, —S—R 12 , —O—R 12 or —COO—R 12 .
  • R 12 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 7 to R 10 is —O—R 12 .
  • R 13 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • R 14 to R 17 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or —O—R 18 or —COO—R 12 .
  • R 18 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • at least one of R 14 to R 17 is —O—R 18 .
  • the above colorant may further contain a yellow colorant.
  • the yellow colorant is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, and C.I. I.
  • the colorant may contain a colorant selected from the group consisting of a green colorant, a blue colorant and a red colorant.
  • the color filter coloring composition may further contain a photopolymerizable monomer and / or a photopolymerization initiator.
  • an embodiment of the present invention relates to a color filter comprising a filter segment formed using the above-described color filter coloring composition.
  • the present invention relates to the following Embodiments I to VIII.
  • the problem of the present embodiment is that it has excellent coloring power, and further, when used in a color filter, a colorant for color filter, a coloring composition, and a color filter using the same, which can obtain high brightness and high contrast ratio. Is to provide.
  • the present inventors have found that when used as a color filter colorant containing a quinophthalone compound having a specific structure, it is possible to produce a color filter that is excellent in dispersibility and coloring power and gives high brightness and contrast ratio.
  • the present embodiment has been reached.
  • this embodiment relates to a color filter colorant characterized by containing a quinophthalone compound represented by the general formula (1).
  • the quinophthalone compound represented by the general formula (1) is preferably any one of the general formulas (1A) to (1C).
  • R 14 to R 28 , R 29 to R 43 , and R 44 to R 60 may each independently be a hydrogen atom or a halogen atom.
  • the colorant preferably contains a yellow colorant.
  • the yellow colorant is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, and C.I. I. It is preferably at least one selected from CI Pigment Yellow 185.
  • the color filter coloring composition may contain a green colorant and / or a blue colorant.
  • the coloring composition for color filters may contain a photopolymerizable monomer and / or a photopolymerization initiator.
  • at least one green filter segment is a color formed by the above color filter coloring composition. It may be a filter.
  • the color filter colorant has high brightness, high contrast ratio, and excellent coloring power.
  • a coloring composition, and a color filter using the same can be provided.
  • the problem of the present embodiment is that it has excellent coloring power and dispersibility, and further, when used in a color filter, a color composition for a color filter capable of obtaining a high brightness and a high contrast ratio, and a color filter using the same Is to provide.
  • the present inventors have excellent dispersibility and coloring power, and give high brightness and contrast ratio when a pigment containing a quinophthalone compound having a specific structure and an aluminum phthalocyanine pigment are used as colorants for a color filter.
  • the present inventors have found that a color filter can be produced and have reached this embodiment.
  • this embodiment is a color filter coloring composition containing a colorant, a binder resin, and an organic solvent, and the colorant is represented by the general formula (1A), the general formula (1B), and the general formula (1C).
  • the coloring composition for color filters characterized by containing the 1 or more types of pigment chosen from the quinophthalone compound represented by this, and an aluminum phthalocyanine pigment.
  • the aluminum phthalocyanine pigment is any one of the general formula (8A) and the general formula (8B).
  • the coloring composition for color filters contains a photopolymerizable monomer and / or a photopolymerization initiator.
  • substrate may be sufficient.
  • An object of the present embodiment is to provide a coloring composition for a color filter excellent in dispersibility, fluidity, and storage stability, and a color filter using the same.
  • a pigment dispersant made of a vinyl polymer containing an ethylenically unsaturated monomer (a1) having at least one of an ethylene oxide chain or a propylene oxide chain in a copolymer composition is used for the quinophthalone pigment. .
  • this embodiment is a color filter coloring composition
  • a colorant a pigment dispersant, and an organic solvent
  • the colorant is a quinophthalone pigment
  • the pigment dispersant is The urethane prepolymer (E) having an isocyanate group at both ends, obtained by reacting the hydroxyl group of a vinyl polymer (A) having two hydroxyl groups at one end region with the isocyanate group of diisocyanate (B).
  • a pigment dispersant obtained by reacting an isocyanate group with a primary and / or secondary amino group of an amine compound containing at least a polyamine (C), and the vinyl polymer (A) is an ethylene oxide chain or a propylene oxide chain.
  • the copolymer composition contains an ethylenically unsaturated monomer (a1) having at least one of It related to the color composition.
  • the total number of repeating units of the ethylene oxide chain and the propylene oxide chain of the ethylenically unsaturated monomer (a1) is preferably 1 to 50.
  • the content of the ethylenically unsaturated monomer (a1) is preferably in the range of 10 to 90% by weight out of the total 100% by weight of the copolymer composition of the vinyl polymer (A).
  • the weight average molecular weight of the vinyl polymer (A) having two hydroxyl groups in one end region is preferably 500 to 20,000.
  • the quinophthalone pigment is C.I. I.
  • a pigment yellow 138 and / or a quinophthalone compound represented by the general formula (1) It is preferable to contain a pigment yellow 138 and / or a quinophthalone compound represented by the general formula (1).
  • the quinophthalone compound is preferably represented by any one of the general formulas (1A) to (1C).
  • substrate may be sufficient.
  • the quinophthalone pigment is used in combination with a pigment dispersant composed of a vinyl polymer containing an ethylenically unsaturated monomer having at least one of an ethylene oxide chain or a propylene oxide chain in a copolymer composition.
  • a coloring composition for a color filter having both high contrast and dispersion stability, and a color filter using the same and having a high contrast ratio.
  • the problem to be solved by the present embodiment is a coloring composition for a color filter that is excellent in brightness, contrast ratio, and coloring power when used in a color filter, and has other characteristics (heat resistance, light resistance, sensitivity). And a color filter using the same.
  • the inventors of the present invention have the color composition containing the quinophthalone pigment [A] having a specific structure and the quinophthalone dye [B] having a specific structure, so that the coloring composition for a color filter can solve the above-described problems. As a result, the present embodiment has been reached.
  • this embodiment is a color filter coloring composition containing a colorant, a binder resin, and an organic solvent, and the colorant is represented by general formula (1A), general formula (1B), and general formula ( 1 C) 1 or more types of quinophthalone pigment [A] and the quinophthalone dye [B] represented by General formula (6) are contained, It is related with the coloring composition for color filters characterized by the above-mentioned.
  • R 14 to R 28 , R 29 to R 43 , and R 44 to R 60 are preferably each independently a hydrogen atom or a halogen atom.
  • at least one of R 1 to R 6 in the general formula (6) is preferably —OR 7 .
  • substrate may be sufficient.
  • the object of the present embodiment is a colorant that is excellent in color characteristics (lightness) and that satisfies other physical properties (heat resistance, light resistance, solvent resistance), a colored composition comprising the same, and a color using the same
  • the object is to provide a color filter having excellent characteristics (brightness).
  • the present inventors have found a quinophthalone dye having excellent color characteristics (brightness), and have made this embodiment based on this finding.
  • this embodiment relates to a quinophthalone dye represented by the general formula (6).
  • the colorant in the color composition for color filters comprising at least a colorant and a binder resin, the colorant may be a color filter color composition containing the quinophthalone dye.
  • the colorant may contain a pigment.
  • at least one filter segment may be a color filter formed of the above-described color filter coloring composition.
  • a quinophthalone dye having excellent color characteristics (brightness) and other physical properties (heat resistance, light resistance, solvent resistance) can be obtained. Furthermore, a color filter excellent in color characteristics (brightness) can be formed by preparing a color filter with a color filter coloring composition containing the quinophthalone dye. Moreover, the other physical properties (heat resistance, light resistance, solvent resistance) of the formed color filter are also good.
  • the problem to be solved by the present embodiment is to provide a green coloring composition for a color filter having excellent lightness and excellent heat resistance, light resistance, and voltage holding ratio, and a color filter using the same. .
  • this embodiment is a green coloring composition for a color filter containing a colorant, a binder resin, and an organic solvent, in which the colorant is represented by the following general formula (8C) and a general formula It contains the quinophthalone pigment
  • a 1 to A 16 each independently represent a hydrogen atom, a halogen atom, a nitro group, an alkyl group which may have a substituent, or an aryl which may have a substituent.
  • R 1 and R 2 are each independently hydrogen atom, hydroxy group, an optionally substituted alkyl group, an optionally substituted aryl group, or an -OR 3, and R 1 R 2 may be bonded to each other to form a ring.
  • R 3 is an alkyl group which may have a substituent or an aryl group which may have a substituent.
  • R 1 and R 2 in the general formula (8C) is preferably an aryl group which may have a substituent, or —OR 3 .
  • the green coloring composition for color filters may contain a photopolymerizable monomer and / or a photopolymerization initiator.
  • substrate may be sufficient.
  • general formula (8C) has the same structure as that of general formula (8A), although the method for expressing substituents is different.
  • the green coloring composition for a color filter of the present embodiment it is possible to provide a color filter having excellent lightness and excellent heat resistance, light resistance, and voltage holding ratio.
  • the problem to be solved by the present embodiment is to provide a coloring composition for a color filter excellent in contrast ratio and coloring power, and a color filter using the same.
  • the coloring composition for color filters can solve the above-mentioned problems by containing the quinophthalone dye [A1] having a specific structure and the quinophthalone dye [A2] having a specific structure. This embodiment has been reached.
  • the colorant in a color filter coloring composition containing a colorant, a binder resin, and an organic solvent, the colorant is a quinophthalone dye [A1] represented by the general formula (6) and the following general formula:
  • the present invention relates to a coloring composition for a color filter comprising a quinophthalone dye [A2] represented by the formula (7).
  • R 1 to R 6 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group. Or represents —O—R 11 .
  • R 11 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 7 to R 10 are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group, carboxyl group, substituted or unsubstituted And a sulfoamide group, a substituted or unsubstituted heterocyclic residue, —SR 12 , —O—R 12 , or —COO—R 12 .
  • R 12 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • An object of the present embodiment is to provide a pigment excellent in color characteristics (lightness), a coloring composition containing the same, and a color filter excellent in color characteristics (lightness) using the same.
  • the present inventors have found a quinophthalone dye having excellent color characteristics (brightness), and have made this embodiment based on this finding.
  • this embodiment is represented by the following general formula (7A), a quinophthalone dye for a color filter.
  • R 1 to R 6 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group. Or represents —O—R 11 .
  • R 11 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 7 to R 10 are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group, carboxyl group, substituted or unsubstituted And a sulfoamide group, a substituted or unsubstituted heterocyclic residue, —SR 12 , —O—R 12 , or —COO—R 12 .
  • R 12 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group.
  • R 7 to R 10 is —O—R 12 .
  • the quinophthalone dye is preferably represented by the following general formula (7B).
  • R 13 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • R 14 to R 17 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or —O—R 18 .
  • R 18 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • R 14 to R 17 is —O—R 18 .
  • the colorant contains the quinophthalone dye.
  • the colorant may further contain a pigment.
  • at least one filter segment may be a color filter formed of the color filter coloring composition.
  • a quinophthalone dye for a color filter having excellent color characteristics (brightness) can be obtained. Furthermore, a color filter excellent in color characteristics (brightness) can be formed by preparing a color filter with a color filter coloring composition containing the quinophthalone dye. Moreover, the other physical properties (heat resistance, light resistance, solvent resistance) of the formed color filter are also good.
  • the subject of the present invention is 2011-60734 filed on March 18, 2011, Japanese Patent Application No. 2011-093515 filed on April 19, 2011, and Japanese Patent Application No. 2011-93705 filed on April 20, 2011, May 2011.
  • Japanese Patent Application No. 2011-118726 filed on the 27th Japanese Patent Application No. 2011-143658 filed on June 29, 2011, Japanese Patent Application No. 2011-150514 filed on July 7, 2011, Japanese Patent Application No. 2011-150 filed on July 15, 2011 156970, Japanese Patent Application No. 2011-174656 filed on August 10, 2011, Japanese Patent Application No. 2011-181111 filed on August 23, 2011, and Japanese Patent Application No. 2011-286172 filed on December 27, 2011. And are hereby incorporated by reference in their entirety.
  • FIG. 1 is a spectrum of a coating film in Example 5 of Embodiment V.
  • FIG. FIG. 2 is a spectrum of the coating film in Reference Example 1 of Embodiment V.
  • FIG. 3 is a spectrum of the coating film of Reference Example 3 of Embodiment V.
  • FIG. 4 is a spectrum of the coating film in Example 1 of Embodiment VIII.
  • FIG. 5 is a spectrum of the coating film in Reference Example 1 of Embodiment VIII.
  • FIG. 6 is a spectrum of the coating film of Reference Example 4 of Embodiment VIII.
  • the coloring composition for a color filter includes a quinophthalone compound represented by the general formula (1), a quinophthalone dye represented by the general formula (6), and a quinophthalone represented by the general formula (7).
  • a colorant selected from pigments is contained alone or in combination.
  • the coloring composition for color filters may contain the phthalocyanine pigment represented by general formula (8A) or (8B), and may contain other colorants. Each colorant will be described below.
  • halogen atom includes fluorine, chlorine, bromine, Iodine is mentioned.
  • stearyl group linear or branched alkyl group such as 2-ethylhexyl group, trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, pendyl group, 4-methylpentyl group, 4-tert-butylbenzyl group, 4-methoxy Examples thereof include an alkyl group having a substituent such as a pendyl group, a 4-nitrobenzyl group, and a 2,4-dichlorobenzyl group.
  • alkoxyl groups such as 3-dimethyl-3-pentoxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group, trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group, 2,2-ditrifluoromethylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitro
  • alkoxyl group having a substituent such as a propoxy group and a benzyloxy
  • examples of the aryl group which may have a substituent include an aryl group such as a phenyl group, a naphthyl group, an anthranyl group, a p-methylphenyl group, a p-bromophenyl group, a p-nitrophenyl group, a p- Methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4 , 5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthraquinonyl group and the like aryl groups having a substituent.
  • an aryl group such as a phenyl group, a naphthyl group, an anthranyl
  • acidic groups include —SO 3 H and —COOH
  • monovalent to trivalent metal salts of these acidic groups include sodium salts, potassium salts, magnesium salts, calcium salts, iron salts, aluminum salts.
  • Etc alkyl ammonium salt of acidic group
  • quaternary alkyl such as ammonium salt of long-chain monoalkylamine such as octylamine, laurylamine, stearylamine, palmityltrimethylammonium, dilauryldimethylammonium, distearyldimethylammonium salt, etc.
  • An ammonium salt is mentioned.
  • the “substituent” in the phthalimidomethyl group (C 6 H 4 (CO) 2 N—CH 2 —) which may have a substituent and the sulfamoyl group (H 2 NSO 2 —) which may have a substituent “Includes the above halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, and the like.
  • At least one adjacent set of groups out of R 1 to R 4 in the general formula (1) and / or at least one adjacent set of groups out of R 10 to R 13 are united,
  • An aromatic ring which may have a substituent is formed.
  • the aromatic ring herein includes a hydrocarbon aromatic ring and a heteroaromatic ring.
  • the hydrocarbon aromatic ring includes a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and the heteroaromatic ring includes pyridine.
  • the quinophthalone compound used for the color filter colorant is preferably any one of the general formulas (1A) to (1C).
  • R 14 to R 28 , R 29 to R 43 and R 44 to R 60 a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, An aryl group which may have a substituent, —SO 3 H; —COOH; and a monovalent to trivalent metal salt of these acidic groups; an alkylammonium salt, an optionally substituted phthalimidomethyl group, or
  • the sulfamoyl group which may have a substituent is synonymous with the group demonstrated by General formula (1).
  • R 14 to R 28 , R 29 to R 43 , and R 44 to R 60 in the general formulas (1A) to (1C) are hydrogen atoms or halogen atoms. Is more preferable from the viewpoint of lowering the viscosity of the dispersion.
  • quinophthalone compound used for the colorant for the color filter include the following quinophthalone compounds (a) to (r), but are not limited thereto.
  • the quinophthalone compound can be produced, for example, by the method described in Japanese Patent Publication No. 2930774.
  • a general method for producing the quinophthalone compound represented by the general formula (1) will be described.
  • the condensation of phthalic anhydride can proceed in a two-step process by maintaining the reaction mixture at 140 to 160 ° C. for 1 to 3 hours before reaching 160 to 200 ° C.
  • R 61 to R 65 have the same meanings as R 5 to R 9 in formula (1).
  • R 66 to R 69 have the same meanings as R 1 to R 4 and R 10 to R 13 in formula (1).
  • 1 to 2 equivalents of phthalic anhydride represented by the general formula (3) is added to 1 equivalent of 8-aminoquinaldine represented by the general formula (2) and 1 to 140 to 160 ° C.
  • the phthalic anhydride represented by the general formula (3) having a different structure is added in an amount of 1 to 2 equivalents, and the mixture is heated and condensed at 160 to 200 ° C. It is possible to condense phthalic anhydrides having different structures on the amino group side and the methyl group side.
  • two or more structurally different quinophthalone compounds can be synthesized simultaneously by reacting 8-aminoquinaldine with two or more structurally different phthalic anhydrides (hereinafter, “ Co-synthesis method). For example, by condensing 1.8 equivalent of tetrachlorophthalic anhydride and 1.2 equivalent of other phthalic anhydride to 1 equivalent of 8-aminoquinaldine, C.I. I. Pigment Yellow 138 and a specific quinophthalone compound can be produced simultaneously.
  • the compound of the general formula (5) can be synthesized from the quinophthalone compound represented by the compound (1).
  • a quinophthalone compound represented by general formula (1) is synthesized by condensing phthalic anhydride represented by general formula (5) and general formula (3) in benzoic acid at 160 to 200 ° C. Is also possible.
  • the manufacturing method of a quinophthalone compound is not limited to these methods.
  • the colorant of this embodiment may contain two or more quinophthalone compounds. At this time, quinophthalone compounds produced separately may be mixed together, or two or more quinophthalone compounds may be produced at the same time by a cosynthesis method and used as a colorant.
  • these separately prepared quinophthalone compounds may be simply mixed before dispersing the two kinds of pigments, or may be pulverized and mixed by a salt milling process described later.
  • C.I. I. When it contains CI Pigment Yellow 138, it is desirable to use it after being pulverized and mixed by a cosynthesis method or a salt milling process.
  • Pigment Yellow 138 and the quinophthalone compound represented by the general formula (1) are pulverized and mixed together, so that fine particles are obtained and a high contrast ratio is obtained as compared with the case where each is subjected to salt milling alone. .
  • the colored composition containing the quinophthalone compound represented by the general formula (1) has a yellow hue itself, and when used in combination with other colorants, the same color yellow filter segment, and further green It can be set as the coloring composition for forming a filter segment and a red filter segment.
  • the coloring composition of this embodiment can obtain the coloring composition used for the green filter segment which has high brightness and high contrast by using together a green coloring agent and / or a blue coloring agent.
  • the quinophthalone dye represented by the general formula (6) is also referred to as a “quinophthalone dye” represented by the general formula (6) in the present specification.
  • the substituted or unsubstituted alkyl group in R 1 to R 7 in the general formula (6) is a linear, branched, monocyclic or condensed polycyclic alkyl group having 1 to 30 carbon atoms, or 2 carbon atoms. To 30 and includes one or more ester bonds (—COO—) and / or ether bonds (—O—), linear, branched, monocyclic or condensed polycyclic alkyl groups.
  • linear, branched, monocyclic or condensed polycyclic alkyl group having 1 to 30 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group.
  • nonyl group, decyl group, dodecyl group, octadecyl group, trifluoromethyl group, isopropyl group, isobutyl group, isopentyl group, 2-ethylhexyl group, sec-butyl group, tert-butyl group, sec-pentyl group, tert- Examples include, but are not limited to, pentyl group, tert-octyl group, neopentyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, boronyl group, 4-decylcyclohexyl group and the like. It is not something.
  • linear or branched alkyl group having 2 to 30 carbon atoms and including one or more ester bonds include —CH 2 —CH 2 —CH 2 —COO—CH 2 —CH 3 , —CH 2 —CH (—CH 3 ) —CH 2 —COO—CH 2 —CH 3 , —CH 2 —CH 2 —CH 2 —OCO—CH 2 —CH 3 , —CH 2 —CH 2 —CH 2 —CH 2 —COO—CH 2 —CH (CH 2 —CH 3 ) —CH 2 —CH 2 —CH 2 —CH 3 , — (CH 2 ) 5 —COO— (CH 2 ) 11 —CH 3 , —CH 2 —CH Examples include 2 -CH 2 —CH— (COO—CH 2 —CH 3 ) 2, but are not limited thereto.
  • linear or branched alkyl group having 2 to 30 carbon atoms and containing one or more ether bonds include —CH 2 —O—CH 3 , —CH 2 —CH 2 —O—.
  • monocyclic or condensed polycyclic alkyl group having 2 to 30 carbon atoms and optionally including one or more ether bonds include the following, but are not limited thereto. Absent.
  • linear, branched, and alkyl groups having 3 to 30 carbon atoms and including one or more ester bonds (—COO—) and ether bonds (—O—) include —CH 2 — CH 2 —COO—CH 2 —CH 2 —O—CH 2 —CH (CH 2 —CH 3 ) —CH 2 —CH 2 —CH 2 —CH 3 , —CH 2 —CH 2 —COO—CH 2 —CH 2 —O—CH 2 —CH 2 —O—CH 2 —CH (CH 2 —CH 3 ) —CH 2 —CH 2 —CH 2 —CH 3 may be mentioned, but is not limited thereto. .
  • Examples of the substituted or unsubstituted alkenyl group for R 1 to R 7 include linear, branched, monocyclic or condensed polycyclic alkenyl groups having 1 to 18 carbon atoms. They may have a plurality of carbon-carbon double bonds in the structure.
  • Specific examples include vinyl group, 1-propenyl group, allyl group, 2-butenyl group, 3-butenyl group, isopropenyl group, isobutenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4- Pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, cyclopentenyl, cyclohexenyl, 1,3-butadienyl, cyclohexadienyl, cyclopenta Although a dienyl group etc. can be mentioned, it is not limited to these.
  • the substituted or unsubstituted aryl group in R 1 to R 7 is a substituted or unsubstituted monocyclic or condensed polycyclic aromatic group having 6 to 18 carbon atoms, such as a phenyl group, a 1-naphthyl group, 2-naphthyl group, p-biphenyl group, m-biphenyl group, 2-anthryl group, 9-anthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, 2-fluorenyl group, 3-fluorenyl group, 9-fluorenyl group, 1-pyrenyl group, 2-pyrenyl group, 3-perylenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 4-methylbiphenyl group, terphenyl group, 4-methyl-1 -Naphtyl group, 4-tert-butyl-1-naph
  • At least one of R 1 to R 6 in the general formula (6) is preferably —OR 7 .
  • the quinophthalone dye represented by the general formula (6) can be obtained by reacting the corresponding 2-methylquinoline and naphthalenedicarboxylic anhydride in benzoic acid at a high temperature as shown in the following reaction formula.
  • the quinophthalone dye of the general formula (6) has tautomers having structures such as the following general formulas (6a) and (6b), and these tautomers are also within the scope of the present invention. It is.
  • quinophthalone dye represented by the general formula (6) include the following dyes, but the dye of the present invention is not limited thereto.
  • the quinophthalone dye represented by the general formula (6) can be used as a coloring material for coloring printing ink, IJ ink, plastic, paint, fiber, stationery, writing instrument, cosmetics and the like.
  • Examples of the halogen atom in R 1 to R 10 in the general formula (7) and the general formula (7A) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, but are not limited thereto. is not.
  • the substituted or unsubstituted alkyl group in R 1 to R 12 is a linear, branched, monocyclic or condensed polycyclic alkyl group having 1 to 30 carbon atoms, or an ester bond having 2 to 30 carbon atoms
  • linear, branched, monocyclic or condensed polycyclic alkyl group having 1 to 30 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group.
  • linear or branched chain having 2 to 30 carbon atoms include —CH 2 —CH 2 —CH 2 —COO—CH 2 —CH 3 , —CH 2 —CH (—CH 3 ) — CH 2 —COO—CH 2 —CH 3 , —CH 2 —CH 2 —CH 2 —OCO—CH 2 —CH 3 , —CH 2 —CH 2 —CH 2 —CH 2 —COO—CH 2 —CH (CH 2 —CH 3 ) —CH 2 —CH 2 —CH 2 —CH 3 , — (CH 2 ) 5 —COO— (CH 2 ) 11 —CH 3 , —CH 2 —CH 2 —CH 2 —CH— (COO —CH 2 —CH 3 ) 2
  • Monocyclic or condensed having 2 to 30 carbon atoms and optionally containing at least one bond selected from an ester bond (—COO—), an ether bond (—O—), and a sulfide bond (—S—)
  • Specific examples of the polycyclic alkyl group include the following, but are not limited thereto.
  • Examples of the substituted or unsubstituted alkenyl group for R 1 to R 12 include linear, branched, monocyclic or condensed polycyclic alkenyl groups having 1 to 18 carbon atoms. They may have a plurality of carbon-carbon double bonds in the structure.
  • Specific examples include vinyl group, 1-propenyl group, allyl group, 2-butenyl group, 3-butenyl group, isopropenyl group, isobutenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4- Pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, cyclopentenyl, cyclohexenyl, 1,3-butadienyl, cyclohexadienyl, cyclopenta Although a dienyl group etc. can be mentioned, it is not limited to these.
  • the substituted or unsubstituted aryl group in R 1 to R 12 is a monocyclic or condensed polycyclic aromatic group which may contain a substituted or unsubstituted heteroatom having 6 to 30 carbon atoms, such as a phenyl group 1-naphthyl group, 2-naphthyl group, p-biphenyl group, m-biphenyl group, 2-anthryl group, 9-anthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, 2-fluorenyl group 3-fluorenyl group, 9-fluorenyl group, 1-pyrenyl group, 2-pyrenyl group, 3-perylenyl group, terphenyl group, thienyl group, benzothienyl group, naphthothienyl group, furyl group, pyranyl group, pyrrolyl group, imidazolyl Group, pyridyl group,
  • the hydrogen atom of the substituted or unsubstituted alkyl group in R 1 to R 12 and the substituted or unsubstituted aryl group may be further substituted with another substituent.
  • Such substituents include halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, nitro groups, hydroxyl groups, substituted or unsubstituted alkoxyl groups, substituted or unsubstituted aryloxy groups. Can be mentioned.
  • a halogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group include a halogen atom in R 1 to R 12 , a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. Synonymous with group.
  • the substituted or unsubstituted alkoxyl group is a group in which an oxygen atom is bonded to a substituted or unsubstituted alkyl group in R 1 to R 12 .
  • the substituted or unsubstituted reeloxy group is a group in which an oxygen atom is bonded to a substituted or unsubstituted aryl group in R 1 to R 12 .
  • the quinophthalone dye for color filters represented by the general formula (7A) is particularly preferable.
  • the halogen atom, the substituted or unsubstituted alkyl group, the substituted or unsubstituted alkyl group, and the substituted or unsubstituted aryl group in R 13 to R 18 in the general formula (7B) are a halogen atom in R 1 to R 12 . It is synonymous with an atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group.
  • the quinophthalone dye for a color filter represented by the general formula (7) can be obtained by reacting the corresponding 2-methylquinoline and the corresponding phthalic anhydride in benzoic acid at a high temperature as shown in the following reaction formula. I can do it.
  • the quinophthalone dye of the general formula (7) has tautomers having the structures of the following general formulas (7a) and (7b). These tautomers are also within the scope of the present invention. It is.
  • quinophthalone dye represented by the general formula (7A) include the following dyes, but the dye of the present invention is not limited thereto.
  • the aluminum phthalocyanine pigment used in the present embodiment is not particularly limited as long as it has a structure in which trivalent aluminum is coordinated at the center of the phthalocyanine ring.
  • aluminum is known to have a structure such as a dimer and a trimer in addition to a monomer, because it is trivalent and has a bond in addition to a bond with phthalocyanine.
  • the phthalocyanine ring can be chemically modified and can take various structures.
  • the aluminum phthalocyanine pigment in the present embodiment may take any form such as not only a monomer but also a structure such as a dimer or a trimer, or a chemical modification of a phthalocyanine ring.
  • the aluminum phthalocyanine pigment those represented by the structure of the general formula (8A) or the general formula (8B) are preferable in terms of color characteristics and dispersibility.
  • X 1 to X 4 may be the same or different. Specific examples thereof include an alkyl group which may have a substituent, an aryl group which may have a substituent, and a substituent.
  • the substituents may be the same or different.
  • halogen groups such as fluorine, chlorine and bromine, amino groups, hydroxyl groups and nitro groups.
  • an alkyl group, an aryl group, a cycloalkyl group, an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, and the like can be given.
  • alkyl group of the alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group,
  • alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group.
  • Examples include a linear or branched alkyl group such as an n-octyl group, a stearyl group, and a 2-ethylhexyl group.
  • alkyl group having a substituent examples include a trichloromethyl group, a trifluoromethyl group, 2, 2, 2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4 -Methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group, etc. That.
  • aryl group of the aryl group which may have a substituent examples include a phenyl group, a naphthyl group, and an anthryl group, and the “aryl group having a substituent” includes a p-methylphenyl group, p- Bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl Group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthraquinonyl group and the like.
  • Examples of the “cycloalkyl group” of the cycloalkyl group which may have a substituent include a cyclopentyl group, a cyclohexyl group, an adamantyl group and the like, and examples of the “cycloalkyl group having a substituent” include 2,5 -Dimethylcyclopentyl group, 4-tert-butylcyclohexyl group and the like.
  • Examples of "" include 3-methylpyridyl group, N-methylpiperidyl group, N-methylpyrrolyl group and the like.
  • alkoxyl group of the alkoxyl group which may have a substituent, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, 2 , 3-dimethyl-3-pentyloxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group and the like linear and branched alkoxyl groups such as “alkoxyl having a substituent”
  • the group include trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2-ditrifluoromethylpropoxy group, 2- Ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benz
  • Examples of the “aryloxy group” of the aryloxy group which may have a substituent include a phenoxy group, a naphthoxy group, and an anthryloxy group, and the “aryloxy group having a substituent” includes p-methyl Examples include phenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chlorophenoxy group.
  • alkylthio group examples include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a decylthio group, a dodecylthio group, and an octadecylthio group.
  • alkylthio group having a substituent examples include a methoxyethylthio group, an aminoethylthio group, a benzylaminoethylthio group, a methylcarbonylaminoethylthio group, a phenylcarbonylaminoethylthio group, and the like.
  • arylthio group examples include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a 9-anthrylthio group, and the like, and “an arylthio group having a substituent” Chlorophenylthio group, trifluoromethylphenylthio group, cyanophenylthio group, nitrophenylthio group, 2-aminophenylthio group, 2-hydroxyphenylthio group and the like.
  • Y 1 to Y 4 include a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group (C 6 H 4 (CO) 2 N—CH 2 —), a sulfamoyl group ( H 2 NSO 2 —).
  • the phthalimidomethyl group having a substituent represents a structure in which a hydrogen atom in the phthalimidomethyl group is substituted by a substituent
  • the sulfamoyl group having a substituent is a hydrogen atom in the sulfamoyl group substituted by a substituent. Represents the resulting structure.
  • Preferred Y is a halogen atom and a sulfamoyl group.
  • a phthalocyanine compound in which m 1 to m 4 are 0 can also be suitably used.
  • the halogen atom include fluorine, chlorine, bromine and iodine.
  • the “substituent” of the phthalimidomethyl group which may have a substituent and the sulfamoyl group which may have a substituent has the same meaning as the substituents of X 1 to X 4 .
  • Z is represented by a hydroxyl group, a chlorine atom, —OP ( ⁇ O) R 1 R 2 , or —O—SiR 3 R 4 R 5 , wherein R 1 and R 2 are a hydrogen atom, a hydroxyl group, respectively.
  • R 1 and R 2 are a hydrogen atom, a hydroxyl group, respectively.
  • alkyl group in R 1 and R 2 methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n-hexyl group, n-octyl group
  • a linear or branched alkyl group such as a stearyl group or 2-ethylhexyl group
  • the substituent when the alkyl group is an alkyl group having a substituent includes a halogen atom such as chlorine, fluorine and bromine
  • alkoxyl groups such as methoxy groups
  • aromatic groups such as phenyl groups and tolyl groups
  • nitro groups alkoxyl groups such as methoxy groups, aromatic groups such as phenyl groups and tolyl groups.
  • alkyl group having a substituent examples include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2-ethoxyethyl group, and a 2-butoxyethyl group.
  • the aryl group in R 1 and R 2 there are a phenyl group, a naphthyl group, an anthryl group, and the like.
  • the substituent is a halogen atom such as chlorine, fluorine, bromine, an alkyl group, There are alkoxyl groups, amino groups, nitro groups and the like. Further, there may be a plurality of substituents.
  • Examples of the aryl group having a substituent include p-tolyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-dimethylamino group.
  • Examples include a phenyl group, 2-methyl-4-chlorophenyl group, 4-methoxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group and the like.
  • alkoxyl group in R 1 and R 2 examples include methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, neopentyloxy group, 2,3-dimethyl-3- Examples include a linear or branched alkoxyl group such as a pentyloxy group, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group, and the like. There are halogen atoms such as chlorine, fluorine and bromine, aryl groups such as alkoxyl groups, phenyl groups and tolyl groups, and nitro groups.
  • alkoxyl group having a substituent examples include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2-ditrifluoro group.
  • alkoxyl group having a substituent examples include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2-ditrifluoro group.
  • examples include methylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benzyloxy group and the like.
  • the aryloxy group in R 1 and R 2 there are a phenoxy group, a naphthaloxy group, an anthryloxy group, and the like.
  • the substituent is a halogen atom such as chlorine, fluorine, bromine or the like.
  • aryloxy group having a substituent examples include, for example, p-methylphenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chloro There are phenoxy groups and the like.
  • R 1 and R 2 are an aryl group or a substituent which may have a substituent.
  • An aryloxy group which may have is preferable. More preferably, R 1 and R 2 are both aryl groups or aryloxy groups. Further preferably, R 1 and R 2 are both phenyl groups or phenoxy groups.
  • R 3 , R 4 and R 5 are each independently an alkyl group having 1 to 18 carbon atoms or an aromatic group having 4 or less rings. If it is in said range, the extinction coefficient per unit weight is enough, and the pigment concentration in a coloring composition can be made into a suitable range.
  • the alkyl group in R 3 , R 4 and R 5 may be linear, branched or cyclic, and has a functional group with a total number of heteroatoms of 3 or less. May be.
  • the aromatic ring may contain a hetero atom, and each aromatic ring may have a functional group in the range of 2 or less hetero atoms.
  • Z is more preferably —OP ( ⁇ O) R 1 R 2 from the viewpoint of heat resistance and light resistance.
  • X 5 to X 12 may be the same or different. Specific examples thereof include an alkyl group which may have a substituent, an aryl group which may have a substituent, and a substituent.
  • the substituents may be the same or different.
  • halogen groups such as fluorine, chlorine and bromine, amino groups, hydroxyl groups and nitro groups.
  • an alkyl group, an aryl group, a cycloalkyl group, an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, and the like can be given.
  • alkyl group of the alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group,
  • alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group.
  • Examples include a linear or branched alkyl group such as an n-octyl group, a stearyl group, and a 2-ethylhexyl group.
  • alkyl group having a substituent examples include a trichloromethyl group, a trifluoromethyl group, 2, 2, 2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4 -Methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group, etc. That.
  • aryl group of the aryl group which may have a substituent examples include a phenyl group, a naphthyl group, and an anthryl group, and the “aryl group having a substituent” includes a p-methylphenyl group, p- Bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl Group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthraquinonyl group and the like.
  • Examples of the “cycloalkyl group” of the cycloalkyl group which may have a substituent include a cyclopentyl group, a cyclohexyl group, an adamantyl group and the like, and examples of the “cycloalkyl group having a substituent” include 2,5 -Dimethylcyclopentyl group, 4-tert-butylcyclohexyl group and the like.
  • Examples of "" include 3-methylpyridyl group, N-methylpiperidyl group, N-methylpyrrolyl group and the like.
  • alkoxyl group of the alkoxyl group which may have a substituent, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, 2 , 3-dimethyl-3-pentyloxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group and the like linear and branched alkoxyl groups such as “alkoxyl having a substituent”
  • the group include trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2-ditrifluoromethylpropoxy group, 2- Ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benz
  • Examples of the “aryloxy group” of the aryloxy group which may have a substituent include a phenoxy group, a naphthoxy group, and an anthryloxy group, and the “aryloxy group having a substituent” includes p-methyl Examples include phenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chlorophenoxy group.
  • alkylthio group examples include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a decylthio group, a dodecylthio group, and an octadecylthio group.
  • alkylthio group having a substituent examples include a methoxyethylthio group, an aminoethylthio group, a benzylaminoethylthio group, a methylcarbonylaminoethylthio group, a phenylcarbonylaminoethylthio group, and the like.
  • arylthio group examples include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a 9-anthrylthio group, and the like, and “an arylthio group having a substituent” Chlorophenylthio group, trifluoromethylphenylthio group, cyanophenylthio group, nitrophenylthio group, 2-aminophenylthio group, 2-hydroxyphenylthio group and the like.
  • Y 5 to Y 12 include a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group (C 6 H 4 (CO) 2 N—CH 2 —), a sulfamoyl group ( H 2 NSO 2 —).
  • the phthalimidomethyl group having a substituent represents a structure in which a hydrogen atom in the phthalimidomethyl group is substituted by a substituent
  • the sulfamoyl group having a substituent is a hydrogen atom in the sulfamoyl group substituted by a substituent. Represents the resulting structure.
  • Preferred Y is a halogen atom and a sulfamoyl group.
  • a phthalocyanine compound in which m 1 to m 4 are 0 can also be suitably used.
  • the halogen atom include fluorine, chlorine, bromine and iodine.
  • the “substituent” of the phthalimidomethyl group which may have a substituent and the sulfamoyl group which may have a substituent has the same meaning as the substituent of X 5 to X 12 .
  • L represents —O—SiR 6 R 7 —O—, —O—SiR 6 R 7 —O—SiR 8 R 9 —O—, or —O—P ( ⁇ O) R 10 —.
  • O— represents that R 6 to R 10 each independently have a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • An alkoxyl group or an aryloxy group which may have a substituent is represented.
  • the alkyl group in R 6 to R 10 includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, and an n-octyl group.
  • a linear or branched alkyl group such as a stearyl group or 2-ethylhexyl group
  • the substituent when the alkyl group is an alkyl group having a substituent includes a halogen atom such as chlorine, fluorine and bromine
  • Examples include alkoxyl groups such as methoxy groups, aromatic groups such as phenyl groups and tolyl groups, and nitro groups. Further, there may be a plurality of substituents.
  • alkyl group having a substituent examples include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2-ethoxyethyl group, and a 2-butoxyethyl group.
  • aryl group in R 6 to R 10 there are a phenyl group, a naphthyl group, an anthryl group, and the like.
  • substituents include a halogen atom such as chlorine, fluorine, and bromine, an alkyl group, There are alkoxyl groups, amino groups, nitro groups and the like. Further, there may be a plurality of substituents.
  • Examples of the aryl group having a substituent include p-tolyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-dimethylamino group.
  • Examples include a phenyl group, 2-methyl-4-chlorophenyl group, 4-methoxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group and the like.
  • Examples of the alkoxyl group in R 6 to R 10 include methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, neopentyloxy group, 2,3-dimethyl-3- Examples include a linear or branched alkoxyl group such as a pentyloxy group, an n-hexyloxy group, an n-octyloxy group, a stearyloxy group, and a 2-ethylhexyloxy group.
  • Examples include halogen atoms such as chlorine, fluorine and bromine, aryl groups such as alkoxyl groups, phenyl groups and tolyl groups, and nitro groups. Further, there may be a plurality of substituents.
  • Examples of the alkoxyl group having a substituent include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2-ditrifluoro group. Examples include methylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benzyloxy group and the like.
  • the aryloxy group in R 6 to R 10 there are a phenoxy group, a naphthaloxy group, an anthryloxy group, and the like.
  • the substituent is a halogen atom such as chlorine, fluorine, bromine or the like.
  • aryloxy group having a substituent examples include, for example, p-methylphenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chloro There are phenoxy groups and the like.
  • R 6 to R 7 and R 6 to R 9 and R 10 have a substituent from the viewpoint of the viscosity and color characteristics of the dispersion.
  • An aryl group which may have a substituent or an aryloxy group which may have a substituent is preferable. More preferably, R 6 to R 7 , R 6 to R 9 , and R 10 are all aryl groups or aryloxy groups. More preferably, R 6 to R 7 , R 6 to R 9 , and R 10 are all phenyl groups or phenoxy groups.
  • the coloring composition containing the colorant represented by the general formula (1), (6) or (7) has a yellow hue, and is used in combination with other pigments as necessary.
  • a coloring composition that exhibits yellow, further green, and red can be obtained, and a colorant that is excellent in resistance, color development, and color reproducibility can be obtained.
  • a green pigment and / or a blue pigment By using together with a green pigment and / or a blue pigment, a green colorant having a high brightness and used for a green filter segment can be obtained.
  • a red pigment and using an orange pigment as needed), the red colorant used for the red filter segment which has high brightness can be obtained.
  • a yellow colorant for use in a yellow filter segment having excellent durability and high coloring power while maintaining high brightness.
  • a dye can be used in combination with the above filter segment.
  • pigments and dyes are exemplified.
  • the green pigment it is preferable to use a polyhalogenated phthalocyanine pigment.
  • the polyhalogenated phthalocyanine pigment represents a phthalocyanine pigment having at least two or more halogen atoms. Specifically, C.I. I. And CI Pigment Green 7, 10, 36, 37, 58 and the like. Of these, C.I. I. Pigment Green 36 and 58.
  • an aluminum phthalocyanine pigment As the blue pigment, it is preferable to use an aluminum phthalocyanine pigment.
  • Aluminum phthalocyanine pigments are preferred pigments because they have higher coloring power than halogenated phthalocyanine pigments. Thereby, the addition amount of a pigment can be reduced or the film thickness of a color filter can be reduced. Moreover, the point which does not contain a halogen atom is also preferable in consideration of environmental safety.
  • ⁇ As yellow pigment C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181 182,185,187,188,193,194,198,199,213,214,21
  • red dyes such as xanthene, azo, disazo, and anthraquinone can be used.
  • red dyes such as xanthene, azo, disazo, and anthraquinone
  • C.I. I. examples thereof include salt-forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338.
  • Particularly preferred pigments here are C.I. I. Pigment Red 177,254.
  • Orange pigment includes C.I. I. And CI Pigment Blue Orange 38, 43, 71, or 73.
  • Yellow dyes include azo dyes, azo metal complex dyes, anthraquinone dyes, indigo dyes, thioindigo dyes, phthalocyanine dyes, diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, thiazine dyes, cationic dyes, cyanine dyes, nitro dyes, quinoline dyes , Naphthoquinone dyes and oxazine dyes.
  • yellow dyes include C.I. I. Acid Yellow 2, 3, 4, 5, 6, 7, 8, 9, 9: 1, 10, 11, 11: 1, 12, 13, 14, 15, 16, 17, 17: 1, 18, 20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40: 1, 41, 42, 42: 1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66, 67, 68, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 19 Etc.
  • C.I. Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44: 1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, 134 etc. are also mentioned.
  • C.I. I. Disperse Yellow 1, 2, 3, 5, 7, 8, 10, 11, 13, 13, 23, 27, 33, 34, 42, 45, 48, 51, 54, 56, 59, 60, 63, 64 67, 70, 77, 79, 82, 85, 88, 93, 99, 114, 118, 119, 122, 123, 124, 126, 163, 184, 184: 1, 202, 211, 229, 231, 232 233, 241, 245, 246, 247, 248, 249, 250, 251 and the like.
  • the preferred colorant content in all the non-volatile components of the colored composition according to this embodiment is 10 to 90% by weight, more preferably 15 to 85% by weight from the viewpoint of sufficient color reproducibility and stability. And most preferably 20 to 80% by weight.
  • the weight ratio of yellow pigment / aluminum phthalocyanine pigment represented by the general formula (8A) and / or (8B) is preferably 80/20 to 10/90. By satisfying this range, it is possible to form a green filter segment having excellent brightness and a wide chromaticity range.
  • the general formula (1) is added to 100 parts by weight of the quinophthalone compound represented by the general formula (1).
  • the range of 10 to 1500 parts by weight of the quinophthalone dye represented by 6) is preferred, and the range of 100 to 1200 parts by weight is more preferred.
  • the amount of the quinophthalone dye represented by the general formula (6) is more than 10 parts by weight, the effect of improving the brightness can be exhibited.
  • the contrast ratio and sensitivity when used as a photosensitive coloring composition are preferable.
  • the usage ratio of the green pigment and / or blue pigment to the quinophthalone dye represented by the general formula (6) is generally based on 100 parts by weight of the pigment.
  • the quinophthalone dye represented by the formula (6) is preferably 1 to 1200 parts by weight, more preferably 5 to 600 parts by weight.
  • the addition amount of the quinophthalone dye represented by the general formula (6) is 1 part by weight or more, the reproducible chromaticity region is wide, and when it is 1200 parts by weight or less, the hue does not change.
  • a yellow pigment and a quinophthalone dye represented by the general formula (6) are used in combination as a colorant (or coloring composition) for forming a green filter segment, a green pigment and / or a blue pigment and yellow coloring are used.
  • the use ratio of the colorant is preferably 1 to 1200 parts by weight, more preferably 5 to 600 parts by weight of the yellow colorant with respect to 100 parts by weight of the pigment. It is.
  • the reproducible chromaticity region is wide when the amount of yellow colorant added is 1 part by weight or more, and the hue does not change when it is 1200 parts by weight or less.
  • the yellow pigment and the general formula (6) As a colorant (or coloring composition) for forming a green filter segment, when a yellow pigment and a quinophthalone dye represented by the general formula (6) are used in combination, the yellow pigment and the general formula (The blending ratio with the content of the quinophthalone dye represented by 6) is preferably 1 to 400 parts by weight of the quinophthalone dye represented by the general formula (6) with respect to 100 parts by weight of the yellow pigment. The amount is preferably 5 to 300 parts by weight.
  • the usage ratio of the red pigment and the quinophthalone dye represented by the general formula (6) is the general formula (6) with respect to 100 parts by weight of the red pigment.
  • the quinophthalone dye represented by the formula is preferably 1 to 800 parts by weight, more preferably 5 to 400 parts by weight.
  • the addition amount of the quinophthalone dye represented by the general formula (6) is 1 part by weight or more, the reproducible chromaticity region is wide, and when it is 800 parts by weight or less, the hue does not change.
  • the mixing ratio of the red pigment and the nophthalone dye represented by the general formula (6) is 1 for the quinophthalone dye represented by the general formula (6) with respect to 100 parts by weight of the red pigment. It is preferably ⁇ 400 parts by weight, more preferably 5 to 300 parts by weight.
  • the phthalocyanine dye represented by the general formula (8A) or (8B) and the quinophthalone dye represented by the general formula (6) are used in combination, 100 parts by weight of the phthalocyanine dye represented by the general formula (6) is used. On the other hand, the range of 3 to 1200 parts by weight of the quinophthalone dye represented by the general formula (6) is preferable, and the range of 5 to 800 parts by weight is more preferable.
  • the amount of the quinophthalone dye represented by the general formula (8A) or (8B) is more than 3 parts by weight, the effect of improving the brightness can be sufficiently exhibited. On the other hand, when the amount is less than 1200 parts by weight, the heat resistance and light resistance are improved, which is preferable.
  • the general formula is used with respect to 100 parts by weight of the quinophthalone dye represented by the general formula (6).
  • the quinophthalone dye represented by (7) is preferably in the range of 11 to 900 parts by weight. A more preferred range is 27 to 650 parts by weight, and a further more preferred range is 43 to 400 parts by weight.
  • the amount of the quinophthalone dye represented by the general formula (7) is 11 parts by weight or more, the fluorescence of the quinophthalone dye represented by the general formula (6) is sufficiently quenched, the contrast ratio becomes high, and 900 parts by weight or less. The case is preferable because the coloring power is at a practical level.
  • the use ratio of the green pigment and / or blue pigment and the quinophthalone dye represented by the general formulas (6) and (7) is preferably 5 to 1000 parts by weight, more preferably 100 parts by weight of the pigment. 17 to 600 parts by weight.
  • the addition amount of the quinophthalone dye represented by the general formulas (6) and (7) is 5 parts by weight or more, the reproducible chromaticity region becomes narrow, and when it is 1000 parts by weight or less, the hue does not change.
  • a green pigment and / or a blue pigment and a yellow colorant (yellow pigment and general formulas (6) and (6)) 7)
  • the mixture ratio of the quinophthalone dye represented by 7) is preferably 5 to 1000 parts by weight, more preferably 17 to 600 parts by weight of the yellow colorant with respect to 100 parts by weight of the green pigment and / or blue pigment. It is.
  • the added amount of the yellow colorant is 5 parts by weight or more, the reproducible chromaticity region is wide, and when it is 600 parts by weight or less, the hue does not change.
  • the yellow pigment and the quinophthalone dye represented by the general formulas (6) and (7) are used in combination, the yellow pigment and the quinophthalone dye represented by the general formulas (6) and (7) are considered in consideration of the color composition.
  • the content of the quinophthalone dye represented by the general formulas (6) and (7) is preferably 1 to 400 parts by weight, more preferably 5 to The range is 300 parts by weight.
  • the usage ratio of the red pigment and the quinophthalone dye represented by the general formulas (6) and (7) is 100 parts by weight of the red pigment.
  • the quinophthalone dye represented by the general formulas (6) and (7) is preferably 1 to 100 parts by weight, more preferably 5 to 50 parts by weight.
  • the addition amount of the quinophthalone dye represented by the general formulas (6) and (7) is 1 part by weight or more, the reproducible chromaticity region is wide, and when it is 100 parts by weight or less, the hue does not change.
  • the use ratio of the green pigment and / or blue pigment to the quinophthalone dye represented by the general formula (7A) is preferably 1 to 1200 parts by weight of the quinophthalone dye represented by the general formula (7A) with respect to 100 parts by weight of the pigment. More preferably, it is 5 to 600 parts by weight.
  • the addition amount is 1 part by weight or more, the reproducible chromaticity region is wide, and when it is 1200 parts by weight or less, the hue does not change.
  • a green pigment and / or a blue pigment and a yellow colorant (a yellow pigment, a color pigment, and a general formula (7A)
  • the yellow colorant is preferably used in an amount of 1 to 1200 parts by weight, more preferably 5 to 600 parts by weight, based on 100 parts by weight of the pigment.
  • the addition amount is 1 part by weight, the reproducible chromaticity region is wide, and when it is 1200 parts by weight or less, the hue does not change.
  • the yellow pigment and the quinophthalone dye represented by the general formula (7A) are used in combination to form a pigment for a green filter segment, considering the color composition, the yellow pigment and the quinophthalone dye represented by the general formula (7A)
  • the blending ratio with the content is preferably 1 to 400 parts by weight of the quinophthalone dye represented by the general formula (7A) with respect to 100 parts by weight of the yellow pigment, and more preferably 100 parts by weight of the yellow pigment.
  • the quinophthalone dye represented by the general formula (7A) is in the range of 5 to 300 parts by weight.
  • the usage ratio of the yellow pigment and the quinophthalone dye represented by the general formula (7A) is represented by the general formula (100 parts by weight of the yellow pigment).
  • the quinophthalone dye represented by 7A) is preferably 1 to 1200 parts by weight, more preferably 5 to 600 parts by weight.
  • the mixing ratio of the yellow pigment and the quinophthalone dye represented by the general formula (7A) is 1 for the quinophthalone dye represented by the general formula (7A) with respect to 100 parts by weight of the yellow pigment. It is preferably ⁇ 400 parts by weight, more preferably 5 to 300 parts by weight.
  • the usage ratio of the red pigment and the quinophthalone dye represented by the general formula (7A) is the general formula (7A) with respect to 100 parts by weight of the red pigment. Is preferably 1 to 800 parts by weight, more preferably 5 to 400 parts by weight.
  • the addition amount of the quinophthalone dye represented by the general formula (7A) is 1 part by weight or more, the reproducible chromaticity region is wide, and when it is 800 parts by weight or less, the hue does not change.
  • the mixing ratio of the red pigment and the quinophthalone dye represented by the general formula (7A) is 1 for the quinophthalone dye represented by the general formula (7A) with respect to 100 parts by weight of the red pigment. It is preferably from ⁇ 400 parts by weight, more preferably from 5 to 300 parts by weight. Any of the above blends can be appropriately adjusted and used in consideration of the heat resistance, light resistance, and brightness of the colorant.
  • the colorant is a pigment
  • the method of miniaturization There are no particular restrictions on the method of miniaturization.
  • any of wet grinding, dry grinding, and dissolution precipitation methods can be used, and refinement is performed by performing a salt milling process using a kneader method, which is one type of wet grinding. Can do.
  • the primary particle diameter of the pigment is preferably 5 nm or more because of good dispersion in the colorant carrier.
  • a particularly preferred range is from 10 to 80 nm.
  • the primary particle diameter of the pigment was measured by directly measuring the size of the primary particle from an electron micrograph of the pigment using a TEM (transmission electron microscope). Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the pigment particles.
  • Salt milling is a batch or continuous type of mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent, such as a kneader, 2-roll mill, 3-roll mill, ball mill, attritor, sand mill, planetary mixer, etc.
  • the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water after mechanically kneading while heating using a kneader.
  • the water-soluble inorganic salt serves as a crushing aid, and the pigment is crushed using the high hardness of the inorganic salt during salt milling.
  • water-soluble inorganic salt sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price.
  • the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by weight and most preferably 300 to 1000 parts by weight with respect to 100 parts by weight of the total weight of the pigment from the viewpoint of both processing efficiency and production efficiency.
  • the water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used.
  • a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated.
  • the water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, most preferably 50 to 500 parts by weight, based on 100 parts by weight of the total weight of the pigment.
  • a resin When the salt is milled with a pigment, a resin may be added as necessary.
  • the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used.
  • the resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent.
  • the amount of resin used is preferably in the range of 5 to 200 parts by weight with respect to 100 parts by weight of the total weight of the pigment.
  • the binder resin is one that disperses a colorant, or one that dyes or penetrates, and includes conventionally known thermoplastic resins, thermosetting resins, and the like.
  • the binder resin is preferably a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.
  • the binder resin is preferable because it exerts a chemical interaction with the quinophthalone dye represented by the general formula (6), thereby improving the contrast ratio by quenching the fluorescence.
  • thermoplastic resin examples include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin.
  • an alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer it is preferable to use an alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer.
  • an active energy ray-curable resin having an ethylenically unsaturated double bond can also be used.
  • an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain for an alkali development resist for color filters no coating film foreign matter is generated after the colorant is applied.
  • the stability of the colorant is preferably improved.
  • a linear resin that does not have an ethylenically unsaturated double bond in the side chain is used, the colorant is not easily trapped in the resin and the colorant mixture, and has a degree of freedom.
  • the colorant component easily aggregates and precipitates, but by using an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain, the colorant is converted into a resin in a mixture of resin and colorant.
  • the colorant component does not easily aggregate and precipitate, and the resin is three-dimensionally crosslinked when exposed to active energy rays to form a film. It is estimated that the colorant component is less likely to aggregate and precipitate even if the colorant molecules are fixed and the solvent is removed in the subsequent development step.
  • alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer examples include resins having an acidic group such as a carboxyl group or a sulfone group.
  • Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an ⁇ -olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer.
  • At least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.
  • the alkali-soluble resin preferably has a hydrophilic functional group separately from an acidic group such as acrylic acid from the viewpoint of dispersibility of the quinophthalone pigment.
  • a hydrophilic functional group an ethylenically unsaturated monomer having a hydroxyl group and / or a (poly) alkylene oxide structure and having no aromatic ring is preferably used.
  • Specific examples of such ethylenically unsaturated monomers include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and glycerol mono (meth).
  • Hydroxyl group-containing (meth) acrylates such as acrylate, 4-hydroxyvinylbenzene, and 2-hydroxy-3-phenoxypropyl acrylate; 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-methoxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, diethylene glycol monoethyl ether (meth) acrylate, diethylene glycol mono-2-ethylhex Ether (meth) acrylate, dipropylene glycol monomethyl ether (meth) acrylate, triethylene glycol monomethyl ether (meth) acrylate, triethylene glycol monoethyl ether (meth) acrylate, tripropylene glycol monomethyl ether (meth) acrylate, tetraethylene glycol Monomethyl ether (meth) acrylate, polyethylene
  • the content of the ethylenically unsaturated monomer having the hydroxyl group and / or (poly) alkylene oxide structure and having no aromatic ring can be appropriately selected within a range that does not impair the solubility in the synthesis solvent.
  • propylene glycol monomethyl ether acetate is used as the synthesis solvent, it can be suitably used in a range of preferably 5 to 50% by weight, more preferably 10 to 35% by weight.
  • the weight average molecular weight (Mw) of the alkali-soluble resin is preferably in the range of 5,000 to 100,000, more preferably in the range of 5,000 to 40,000.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 50,000, and the value of Mw / Mn is preferably 10 or less.
  • the glass transition temperature of the alkali-soluble resin (hereinafter sometimes referred to as Tg) is preferably ⁇ 40 to 70 ° C., more preferably ⁇ 30 to 30 ° C., and ⁇ 20 to 10 from the viewpoint of dispersion stability. More preferably.
  • Tg of main homopolymers used for calculation.
  • Methacrylic acid 130 ° C (403K) Butyl acrylate: -54 ° C (219K) Benzyl methacrylate: 55 ° C
  • Benzyl methacrylate 55 ° C
  • Paracumylphenol ethylene oxide-modified acrylate (M-110, manufactured by Toagosei Co., Ltd.): 35 ° C (308K) 4-hydroxybutyl acrylate: ⁇ 80 ° C. (193 K) 2-hydroxyethyl methacrylate: 55 ° C.
  • (328 K) methoxypolyethylene glycol methacrylate manufactured by NOF Corporation, PME-400
  • ⁇ 60 ° C. (213 K) butyl methacrylate 20 ° C (293K)
  • an active energy ray-curable resin having an ethylenically unsaturated active double bond for example, a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, an amino group, etc.
  • a molecule is prepared, and a (meth) acryl compound having a reactive substituent such as an isocyanate group, an aldehyde group, or an epoxy group or cinnamic acid is reacted to form a photocrosslinkable group such as a (meth) acryloyl group or a styryl group.
  • a method of obtaining a resin introduced into a linear polymer, or a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an ⁇ -olefin-maleic anhydride copolymer with a hydroxyalkyl (meth) acrylate A method of half-esterification with a (meth) acrylic compound having a hydroxyl group such as a hydroxyl group such as a hydroxyalkyl (meth) acrylate ( A) A method of adding a (meth) acrylic compound having an isocyanate group such as (meth) acryloyloxyethyl isocyanate to a linear polymer copolymerized with an acrylic compound, or a carboxyl group such as (meth) acrylic acid There is a method of adding a (meth) acryl compound having an epoxy group such as glycidyl (meth) acrylate to the linear polymer to be included.
  • thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferable as the color composition for color filters.
  • Examples of the monomer constituting the thermoplastic resin include the following. For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) Acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypol
  • thermosetting resin examples include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.
  • an epoxy resin and a melamine resin are used more suitably from a viewpoint of heat resistance improvement.
  • the weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 100,000 in order to disperse the colorant preferably, and more preferably in the range of 5,000 to 80,000, 10,000.
  • the range of ⁇ 80,000, 7,000 to 50,000, 8,000 to 50,000 can be taken.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 50,000, and more preferably in the range of 5,000 to 50,000 and 2,500 to 40,000.
  • the value of Mw / Mn is preferably 10 or less.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are obtained by connecting four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation.
  • HCV-8120GPC gel permeation chromatography
  • This is a polystyrene-equivalent molecular weight measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by the company and using tetrahydrofuran as the mobile phase.
  • the weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 to 50,000 in order to disperse the colorant preferably.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 40,000, and the value of Mw / Mn is preferably 10 or less.
  • the binder resin When the binder resin is used as a coloring composition for a color filter, a colorant adsorbing group and a carboxyl group that acts as an alkali-soluble group during development, an aliphatic group that acts as an affinity group for the colorant carrier and solvent, and an aromatic group
  • the balance of groups is important for the dispersibility, penetrability, developability, and durability of the colorant, and it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g.
  • the acid value is less than 20 mgKOH / g, the solubility in the developing solution is poor and it is difficult to form a fine pattern.
  • it exceeds 300 mgKOH / g a fine pattern does not remain by development.
  • the binder resin is preferably used in an amount of 20 to 500 parts by weight, more preferably 30 to 500 parts by weight with respect to 100 parts by weight of the colorant.
  • it is preferably used in an amount of 20 to 400 parts by weight. If it is 20 parts by weight or more, the fluorescence is sufficiently quenched.
  • the amount is 400 parts by weight or less, self-quenching by the quinophthalone dyes represented by the general formula (6) is not inhibited.
  • the colorant is sufficiently dispersed and permeated in the colorant carrier, and is applied onto a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 ⁇ m.
  • an organic solvent is included. The organic solvent is selected in consideration of good applicability of the coloring composition, solubility of each component of the coloring composition, and safety.
  • organic solvent examples include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane.
  • the dispersibility of the coloring agent, the penetrability, and the coating property of the coloring composition are good, so that alkyl lactates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate It is preferable to use glycol acetates such as ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone.
  • alkyl lactates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate
  • glycol acetates such as ethylene glycol monoethyl ether acetate
  • alcohols such as benzyl alcohol and diacetone alcohol
  • ketones such as cyclohexanone.
  • Organic solvents can be used singly or in combination of two or more at any ratio as necessary.
  • the organic solvent is used in an amount of 500 to 4000 parts by weight with respect to 100 parts by weight of the colorant because the colored composition can be adjusted to an appropriate viscosity to form a filter segment having a desired uniform film thickness. It is preferably 800 to 4000 parts by weight.
  • the coloring composition may contain a dispersion aid.
  • a dispersion aid such as a pigment derivative, a resin-type dispersant, or a surfactant can be appropriately used. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the color composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has lightness and viscosity stability. Become good.
  • the fluorescence of the quinophthalone dye is quenched by the chemical interaction between the quinophthalone dye and the dye derivative or the resin-type dispersant, resulting in a good contrast ratio.
  • dye derivative examples include compounds obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group which may have a substituent into an organic pigment, anthraquinone, acridone, or triazine.
  • quinophthalone dye When the quinophthalone dye emits fluorescence, those having an anthraquinone skeleton, an acridone skeleton, or a phthalocyanine skeleton are preferable from the viewpoint of fluorescence quenching. Furthermore, what has a sulfonamide as a substituent is preferable.
  • the content of the pigment derivative is preferably 0.5 parts by weight or more, more preferably 1 part by weight or more, and most preferably 3 parts by weight or more with respect to 100 parts by weight of the colorant from the viewpoint of improving dispersibility. Further, from the viewpoint of heat resistance and light resistance, it is preferably 40 parts by weight or less, more preferably 35 parts by weight or less.
  • the resin-type dispersant has a colorant-affinity part having a property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize.
  • resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts.
  • Oil-soluble dispersants such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc.
  • Resin water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more, not necessarily limited thereto.
  • an ethylenically unsaturated monomer (a1) having at least one of an ethylene oxide chain or a propylene oxide chain is copolymerized as a resin-type dispersant. It is preferable to use a dispersant contained in the composition from the viewpoints of dispersibility, fluidity, and storage stability.
  • the resin type dispersant will be described in the following item of pigment dispersant.
  • a polymer dispersant having a basic functional group is preferred because the viscosity of the coloring composition is lowered and a high contrast is exhibited with a small addition amount, and a nitrogen atom-containing graft copolymer is preferred.
  • a nitrogen atom-containing acrylic block copolymer and a urethane polymer dispersant having a functional group containing a tertiary amino group, a quaternary ammonium base, a nitrogen-containing heterocyclic ring, or the like in the side chain are preferable.
  • resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 167 manufactured by Big Chemie Japan.
  • the content of the resin-type dispersant is preferably 0.1 to 55 parts by weight, more preferably 0.1 to 45 parts by weight with respect to 100 parts by weight of the colorant.
  • the content of the resin-type dispersant is 0.1 parts by weight or more, the added effect is sufficiently obtained, and when the content is 55 parts by weight or less, the dispersion is very good.
  • the resin-type dispersant is preferably used in an amount of about 5 to 200% by weight relative to the total amount of the pigment, and more preferably about 10 to 100% by weight from the viewpoint of film formability.
  • the pigment dispersant contains an ethylenically unsaturated monomer (a1) having at least one of an ethylene oxide chain or a propylene oxide chain in a copolymer composition, and a vinyl polymer having two hydroxyl groups in one terminal region (A ) And the isocyanate group of the urethane prepolymer (E) having an isocyanate group at both ends, obtained by reacting the hydroxyl group of the diisocyanate (B), It is synthesized by reacting a primary and / or secondary amino group of an amine compound containing at least polyamine (C).
  • the vinyl polymer part derived from the vinyl polymer (A) having two hydroxyl groups in one end region is selected from a wide range of pigment carriers and dispersion media by selecting an ethylenically unsaturated monomer constituting the vinyl polymer part. It functions as a solvent affinity site.
  • the amino group introduced via the hydroxyl group present in one end region of the vinyl polymer site and the urea binding site function as an acidic site adsorbing site on the pigment surface.
  • vinyl polymer having two hydroxyl groups in one end region (A) is an ethylene oxide chain or a propylene oxide chain.
  • An ethylenically unsaturated monomer (a1) having at least one, and an ethylenically unsaturated monomer (a2) copolymerizable with (a1), two hydroxyl groups and one thiol group in the molecule It is preferably obtained by radical polymerization in the presence of the compound (a3) having A method in which radical polymerization is carried out in the presence of a polymerization initiator and a polymerization solvent is preferably used.
  • the ethylenically unsaturated monomer (a1) having at least one of ethylene oxide chain or propylene oxide chain
  • the ethylenically unsaturated monomer (a1) is not particularly limited as long as it has at least one of an ethylene oxide chain or a propylene oxide chain, and a conventionally known monomer can be used. Specific examples include 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, diethylene glycol monoethyl ether (meth) acrylate.
  • the ethylene oxide chain and / or propylene oxide chain of the ethylenically unsaturated monomer (a1) is used for the purpose of improving the dispersibility of the quinophthalone pigment.
  • the ethylenically unsaturated monomer (a1) only needs to have at least one of an ethylene oxide chain or a propylene oxide chain, and more preferably has at least an ethylene oxide chain.
  • the dispersibility with respect to the quinophthalone pigment is determined by the number of moles of ethylene oxide and / or propylene oxide added to the ethylenically unsaturated monomer (a1) forming the vinyl polymer (A) and the ethylenic property of the vinyl polymer (A).
  • the preferred range varies depending on the quinophthalone pigment and the pigment dispersant, but is preferably 1 to 50 in terms of the number of moles of ethylene oxide and / or propylene oxide added in the ethylenically unsaturated monomer (a1). Is more preferable, and 4 to 13 is particularly preferable.
  • the added mole number is 50 or less, the compatibility with the solvent and the dispersibility are good, and the viscosity does not easily increase during dispersion.
  • the blending ratio of the ethylenically unsaturated monomer (a1) is preferably 10 to 90% by weight, preferably 20 to 80% by weight with respect to 100% by weight in total with the ethylenically unsaturated monomer (a2) described later. % Is more preferable, and 30 to 70 parts by weight is particularly preferable.
  • the content is 10% by weight or more, the dispersibility is good.
  • the content is 90% by weight or less, the compatibility with the solvent is excellent, the dispersibility is good, and the viscosity at the time of dispersion is good.
  • the ethylenically unsaturated monomer (a2) is a monomer other than the ethylenically unsaturated monomer (a1) and can be copolymerized with the ethylenically unsaturated monomer (a1). If it is, it will not specifically limit, According to a use, it can select suitably.
  • styrenes such as styrene and ⁇ -methylstyrene
  • Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether
  • fatty acid vinyls such as vinyl acetate and vinyl propionate can also be used.
  • a carboxyl group-containing ethylenically unsaturated monomer can be used in combination.
  • the carboxyl group-containing ethylenically unsaturated monomer include (meth) acrylic acid, (meth) acrylic acid dimer, itaconic acid, maleic acid, fumaric acid, crotonic acid, 2- (meth) acryloyloxyethyl phthalate, 2 -(Meth) acryloyloxypropyl phthalate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxypropyl hexahydrophthalate, ⁇ -carboxyethyl (meth) acrylate, and ⁇ -carboxypoly Examples include caprolactone (meth) acrylate.
  • One or two or more types can be selected from the ethylenically unsaturated monomers listed above, and at least methyl (meth) acrylate and ethyl (meth) from the viewpoint of solubility in solvents and resistance.
  • An ethylenically unsaturated monomer selected from acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, and t-butyl (meth) acrylate; Part of it is preferably used.
  • the compound (a3) having two hydroxyl groups and one thiol group in the molecule includes two hydroxyl groups and one thiol group in the molecule.
  • a vinyl polymer (A) can be obtained by mixing and heating a2) and, optionally, a polymerization initiator.
  • Compound (a3) is preferably obtained by bulk polymerization or solution polymerization using 0.5 to 30 parts by weight based on 100 parts by weight of the total of ethylenically unsaturated monomers (a1) and (a2), More preferred is 1 to 20 parts by weight, still more preferred is 2 to 15 parts by weight, and particularly preferred is 2 to 10 parts by weight.
  • the molecular weight of the vinyl polymer (A) can be adjusted to a suitable range by using the compound (a3) within the above preferred range.
  • the weight average molecular weight (Mw) in terms of polystyrene in the gel permeation chromatography (GPC) of the vinyl polymer (A) is preferably 500 to 20,000, more preferably 1,000 to 10,000, and more preferably 2,000 to 7,500 is particularly preferred.
  • the molecular weight is 20,000 or less, the molecular weight of the vinyl polymer portion is in an appropriate range and the effect of dispersibility is good.
  • the effect of the steric repulsion is sufficient, and the aggregation of the pigment is sufficiently suppressed.
  • Polymerization initiator In the polymerization, 0.001 to 5 parts by weight of a polymerization initiator can be arbitrarily used with respect to 100 parts by weight of the total of ethylenically unsaturated monomers (a1) and (a2). As the polymerization initiator, an azo compound and an organic peroxide can be used.
  • azo compounds examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane 1-carbonitrile), 2 , 2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2'-azobis (2-methylpropionate) 4,4′-azobis (4-cyanovaleric acid), 2,2′-azobis (2-hydroxymethylpropionitrile), and 2,2′-azobis [2- (2-imidazolin-2-yl) ) Propane] and the like.
  • organic peroxides examples include benzoyl peroxide, t-butyl perbenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di (2-ethoxyethyl) peroxy
  • examples thereof include dicarbonate, t-butyl peroxyneodecanoate, t-butyl peroxybivalate, (3,5,5-trimethylhexanoyl) peroxide, dipropionyl peroxide, and diacetyl peroxide.
  • These polymerization initiators can be used alone or in combination of two or more.
  • Polymerization solvent In the case of solution polymerization, ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, hexane, acetone, hexane, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, and Although diethylene glycol diethyl ether etc. are used, it is not specifically limited to these. These polymerization solvents may be used as a mixture of two or more, but are preferably used for final use.
  • diisocyanate (B) As the diisocyanate (B) constituting the pigment dispersant, conventionally known diisocyanates (B) can be used. For example, aromatic diisocyanate (b1), aliphatic diisocyanate (b2), aromatic-aliphatic diisocyanate (b3) ), Alicyclic diisocyanate (b4) and the like.
  • Aromatic diisocyanates (b1) include xylylene diisocyanate, 1,3-phenylene diisocyanate, 4,4′-diphenyl diisocyanate, 1,4-phenylene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,4-tolylene diene Examples include isocyanate, 2,6-tolylene diisocyanate, 4,4′-toluidine diisocyanate, naphthylene diisocyanate, and 1,3-bis (isocyanatomethyl) benzene.
  • Examples of the aliphatic diisocyanate (b2) include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, Examples include dodecamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate.
  • aromatic-aliphatic diisocyanate (b3) examples include ⁇ , ⁇ ′-diisocyanate-1,3-dimethylbenzene, ⁇ , ⁇ ′-diisocyanate-1,4-dimethylbenzene, ⁇ , ⁇ ′-diisocyanate-1,4. -Diethylbenzene, 1,4-tetramethylxylylene diisocyanate, 1,3-tetramethylxylylene diisocyanate, and the like.
  • Examples of the alicyclic diisocyanate (b4) include 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate (IPDI), 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate. Methyl-2,4-cyclohexane diisocyanate, and methyl-2,6-cyclohexane diisocyanate.
  • IPDI 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate
  • IPDI 1,3-cyclopentane diisocyanate
  • 1,3-cyclohexane diisocyanate 1,4-cyclohexane diisocyanate
  • Methyl-2,4-cyclohexane diisocyanate, and methyl-2,6-cyclohexane diisocyanate are examples of the alicyclic di
  • the listed diisocyanates (B) are not necessarily limited to these, and two or more kinds can be used in combination.
  • the diisocyanate (B) is preferably an aliphatic diisocyanate (b2), an aromatic-aliphatic diisocyanate (b3), or an alicyclic diisocyanate (b4) from the viewpoint of hardly yellowing, and more preferably an alicyclic diisocyanate. (B4) is preferred, and most preferred is 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (also known as isophorone diisocyanate, IPDI).
  • IPDI isophorone diisocyanate
  • some polyisocyanates having three or more isocyanate groups in one molecule can be used as long as they do not gel when the pigment dispersant is produced.
  • these include, for example, the isocyanurate bodies of the diisocyanate (B) listed above, trimethylolpropane adduct type, and biuret type.
  • the urethane prepolymer (E) refers to a product obtained by reacting the hydroxyl group of the vinyl polymer (A) having two hydroxyl groups in one terminal region with the isocyanate group of the diisocyanate (B).
  • a known synthesis catalyst can be used, and examples thereof include tertiary amine compounds and organometallic compounds.
  • tertiary amine compound examples include triethylamine, triethylenediamine, N, N-dimethylbenzylamine, N-methylmorpholine, and diazabicycloundecene (DBU).
  • DBU diazabicycloundecene
  • organometallic compounds examples include tin compounds and non-tin compounds.
  • tin compounds include: Dibutyltin dichloride, dibutyltin oxide, dibutyltin dibromide, dibutyltin dimaleate, dibutyltin dilaurate (DBTDL), dibutyltin diacetate, dibutyltin sulfide, tributyltin sulfide, tributyltin oxide, tributyltin acetate, triethyltin ethoxide, tributyl Examples thereof include tin ethoxide, dioctyl tin oxide, tributyltin chloride, tributyltin trichloroacetate, and tin 2-ethylhexanoate.
  • DBTDL dibutyltin dilaurate
  • dibutyltin diacetate dibutyltin sulfide, tributyltin sulfide, tributyl
  • Titanium series such as dibutyltitanium dichloride, tetrabutyltitanate, butoxytitanium trichloride, lead oleate
  • Lead systems such as lead 2-ethylhexanoate, lead benzoate, and lead naphthenate
  • Iron systems such as iron 2-ethylhexanoate and iron acetylacetonate
  • Cobalt-based compounds such as cobalt benzoate and cobalt 2-ethylhexanoate
  • Zinc series such as zinc naphthenate and zinc 2-ethylhexanoate
  • Zirconium-based compounds such as zirconium naphthenate
  • dibutyltin dilaurate (DBTDL), tin 2-ethylhexanoate and the like are preferable in terms of reactivity and hygiene.
  • the catalysts such as the tertiary amine compounds and organometallic compounds can be used alone or in combination depending on the case.
  • the organometallic compound catalyst used in the synthesis of the urethane prepolymer (E) remarkably accelerates the reaction even in the further reaction with the amine described later.
  • a known solvent is preferably used for the synthesis of the urethane prepolymer (E).
  • the use of a solvent serves to facilitate reaction control.
  • Examples of the solvent used for this purpose include: Examples include ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, hexane, acetone, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether. Is not to be done.
  • the concentration in the urethane prepolymer reaction system when a solvent is used is preferably 30 to 95% by weight in terms of reaction control in terms of the solid content concentration of the urethane prepolymer. More preferably, the content is 40 to 90% by weight. If it is 30% by weight or more, the reaction is fast and no unreacted material remains. If it is 95% by weight or less, the reaction does not proceed partly rapidly and the molecular weight and the like can be easily controlled.
  • urethanization reaction in which the hydroxyl group of the vinyl polymer (A) and the isocyanate group of the diisocyanate (B) are reacted to form the urethane prepolymer (E).
  • 1) A method of reacting by charging the whole amount 2) A method of adding a vinyl polymer (A) and, if necessary, a solvent to a flask, dropping a diisocyanate (B) and adding a catalyst as required.
  • 2) is preferable when the reaction is precisely controlled.
  • the reaction temperature for obtaining the urethane prepolymer (E) is preferably 120 ° C. or lower. More preferably, it is 50 to 110 ° C. When the temperature is higher than 110 ° C., it becomes difficult to control the reaction rate, and a urethane prepolymer having a predetermined molecular weight and structure cannot be obtained.
  • the urethanization reaction is preferably carried out at 50 to 110 ° C. for 1 to 20 hours in the presence of a catalyst.
  • the molar ratio of the diisocyanate (B) to the vinyl polymer (A) is preferably 1.01 to 3.00 from the viewpoint of the productivity of the urethane prepolymer, and the design of the dispersant that is the final product (pigment adsorption site) 1.30 to 2.30 is more preferable from the viewpoint of the balance of the solvent-affinity part and 1.30 to 2.30 from the viewpoint of the dispersion stability of the pigment dispersion using the dispersant which is the final product. 00 is most preferred.
  • the dispersant as the final product has a high molecular weight, and the viscosity of the pigment dispersion using the dispersant, and further the paint or ink using the dispersant increases, which causes a practical problem.
  • the diisocyanate (B) having no vinyl polymer part derived from the vinyl polymer (A) and the urethane part derived therefrom increase, and the dispersant is the final product. May degrade performance.
  • the polyamine (C) constituting the pigment dispersant is a compound having at least two primary and / or secondary amino groups, and is used for reacting with an isocyanate group to form a urea bond.
  • An example of such an amine is diamine (c1).
  • diamine (c1) examples include diamine (c1-1) having two primary amino groups, diamine (c1-2) having two secondary amino groups, and diamine (c1-3) having primary and secondary amino groups. Can be mentioned.
  • diamine (c1-1) having two primary amino groups known ones can be used. Specifically, Ethylenediamine, propylenediamine [alias: 1,2-diaminopropane or 1,2-propanediamine], trimethylenediamine [alias: 1,3-diaminopropane or 1,3-propanediamine], tetramethylenediamine [alias: 1 , 4-diaminobutane], 2-methyl-1,3-propanediamine, pentamethylenediamine [alias: 1,5-diaminopentane], hexamethylenediamine [alias: 1,6-diaminohexane], 2,2- Aliphatic diamines such as dimethyl-1,3-propanediamine, 2,2,4-trimethylhexamethylenediamine, and tolylenediamine; Alicyclic diamines such as isophorone diamine and dicyclohexylmethane-4,4′-diamine; and Examples thereof include aromatic di
  • diamine (c1-2) having two secondary amino groups known ones can be used. Specifically, examples thereof include N, N-dimethylethylenediamine, N, N-diethylethylenediamine, and N, N′-di-tert-butylethylenediamine.
  • N-methylethylenediamine [alias: methylaminoethylamine], N-ethylethylenediamine [alias: ethylaminoethylamine], N-methyl-1,3-propanediamine [alias: N-methyl-1,3-diaminopropane or methylamino Propylamine], N, 2-methyl-1,3-propanediamine, N-isopropylethylenediamine [alias: isopropylaminoethylamine], N-isopropyl-1,3-diaminopropane [alias: N-isopropyl-1,3- Propanediamine or isopropylaminopropylamine], and N-lauryl-1,3-propanediamine [also known as N-lauryl-1,3-diaminopropane or laurylaminopropylamine].
  • the polyamine constituting the pigment dispersant is a compound having at least two primary and / or secondary amino groups, and the primary and / or secondary amine reacts with an isocyanate group to form a urea group.
  • This urea group is a pigment.
  • the polyamine (C) is a compound having two primary and / or secondary amino groups at both ends and further having a secondary and / or tertiary amino group at both ends other than the ends. Is particularly preferable because the adsorptivity to the quinophthalone pigment is improved.
  • polyamine (C) examples include polyamines having two primary and / or secondary amino groups at both ends as shown below, and further having secondary and / or tertiary amino groups at both ends. c2).
  • polyamine (c2) examples include a polyamine (c2-1) having a secondary amino group other than both ends and a polyamine (c2-2) having a tertiary amino group other than both ends.
  • polyamine (c2-1) having a secondary amino group other than both ends examples include, for example, iminobispropylamine [also known as N, N-bis (3-aminopropyl) amine], N, N′-bisaminopropyl- Examples thereof include 1,3-propylenediamine, N, N′-bisaminopropyl-1,4-butylenediamine, and the like.
  • polyamine (c2-2) having a tertiary amino group other than both ends examples include, for example, methyliminobispropylamine [alias N, N-bis (3-aminopropyl) methylamine], lauryliminobispropylamine [alias] N, N-bis (3-aminopropyl) laurylamine] and the like.
  • a polymer (c3) having two or more primary and / or secondary amino groups and having a molecular weight distribution can also be used.
  • Examples of the polymer (c3) having a primary and / or secondary amino group include an ethylenically unsaturated monomer having a primary amino group and an ethylenically unsaturated monomer having a secondary amino group, such as vinylamine and allylamine.
  • Homopolymers (so-called polyvinylamine and polyallylamine), copolymers thereof with other ethylenically unsaturated monomers, ring-opening polymers of ethyleneimine, and polycondensates of ethylene chloride and ethylenediamine Or a ring-opening polymer of oxazolidone-2 (so-called polyethyleneimine).
  • (c1), (c2), and (c3) exemplified as the polyamine (C) are preferable from the viewpoint of control of synthesis, and (c2) is preferable from the viewpoint of dispersion performance.
  • a polyamine (c2-1) having a secondary amino group other than both ends is preferable.
  • a monoamine in addition to the polyamine (C), a monoamine can also be used.
  • the monoamine is a monoamine compound having one primary amino group or one secondary amino group in the molecule, and the monoamine suppresses excessively high molecular weight in the reaction of diisocyanate (B) and polyamine (C). Used as a reaction terminator.
  • the monoamine may have a polar functional group other than the primary amino group or the secondary amino group in the molecule. Examples of such a polar functional group include a hydroxyl group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, a cyano group, and a nitroxyl group.
  • the monoamine conventionally known ones can be used, specifically, Aminomethane, aminoethane, 1-aminopropane, 2-aminopropane, 1-aminobutane, 2-aminobutane, 1-aminopentane, 2-aminopentane, 3-aminopentane, isoamylamine, N-ethylisoamylamine, 1-amino Hexane, 1-aminoheptane, 2-aminoheptane, 2-octylamine, 1-aminononane, 1-aminodecane, 1-aminododecane, 1-aminotridecane, 1-aminohexadecane, stearylamine, aminocyclopropane, aminocyclobutane Aminocyclopentane, aminocyclohexane, aminocyclododecane, 1-amino-2-ethylhexane, 1-amino-2-methylpropane, 2-a
  • a monoamine compound having only a secondary amino group as an aliphatic amine having no rigidity is preferable because of good dispersibility.
  • the tertiary amino group does not have an active hydrogen that reacts with the isocyanate group
  • the diamine having the primary or secondary amino group and the tertiary amino group is used as a monoamine constituting the pigment dispersant.
  • a tertiary amino group having an effect of improving the pigment adsorption ability can be introduced into the polymer terminal of the dispersant.
  • diamine having a primary or secondary amino group and a tertiary amino group examples include N, N-dimethylethylenediamine, N, N-diethylethylenediamine, N, N-dimethyl-1,3-propanediamine, and N, N A diamine having a primary amino group and a tertiary amino group, such as 1,2,2-tetramethyl-1,3-propanediamine; and Examples thereof include a diamine having a secondary amino group and a tertiary amino group such as N, N, N′-trimethylethylenediamine.
  • the urea-bonded active hydrogen after the reaction of the primary amine group and the isocyanate group has low reactivity, and under the polymerization conditions of the dispersant, it does not further react with the isocyanate group and the molecular weight does not increase.
  • the pigment dispersant is In the presence of a compound (a3) having two hydroxyl groups and one thiol group in the molecule, an ethylenically unsaturated monomer (a1) represented by the general formula (1) and an ethylenically unsaturated monomer
  • a urethane prepolymer (E) having an isocyanate group at both ends is prepared by reacting the hydroxyl group of the vinyl polymer (A) having two hydroxyl groups in one terminal region with the isocyanate group of diisocyanate (B).
  • the second step It is preferable to produce by the third step of reacting the isocyanate group of the urethane prepolymer (E) having an isocyanate group at both ends with the primary and / or secondary amino group of the polyamine (C).
  • the method is roughly divided into a method of dropping polyamine (C) and 2) a method of adding a solution of polyamine (C) and a solvent as required to a flask and dropping a urethane prepolymer (E) solution. Either method may be used, but the method 2) is preferable from the viewpoint of the dispersion performance of the pigment dispersant to be synthesized.
  • the temperature of the urea reaction is preferably 100 ° C. or less. More preferably, it is 70 degrees C or less. Even at 70 ° C., the reaction rate is high, and when it cannot be controlled, 50 ° C. or less is more preferable. When the temperature is higher than 100 ° C., it is difficult to control the reaction rate, and it is difficult to obtain a urethane urea resin having a predetermined molecular weight and structure.
  • the compounding ratio with the urethane prepolymer (E) and the polyamine (C) is not particularly limited, and can be arbitrarily selected depending on the pigment type.
  • the end point of the reaction can be judged from the disappearance of the isocyanate peak by the isocyanate% measurement or IR measurement due to titration.
  • the weight average molecular weight (Mw) in terms of polystyrene in gel permeation chromatography (GPC) of the pigment dispersant contained in the color filter coloring composition is preferably 1,000 to 100,000, more preferably 1, 500 to 50,000, particularly preferably 1,500 to 20,000.
  • the amine value of the obtained dispersant is preferably 1 to 100 mgKOH / g, more preferably 2 to 80 mgKOH / g, and further preferably 3 to 60 mgKOH / g.
  • the amine value is 1 mgKOH / g or more, the functional group that adsorbs to the pigment is sufficient, so the dispersion of the pigment is good.
  • the amine value is 100 mgKOH / g or less, the pigments do not aggregate and the effect of reducing the viscosity is sufficient.
  • the coating film appearance is good.
  • the pigment dispersant is preferably used in an amount of 5 to 70% by weight, more preferably 10 to 50% by weight, based on the quinophthalone pigment. If it is 5% by weight or more, a good pigment dispersion effect can be obtained, and if it is 70% by weight or less, it does not adversely affect, for example, heat resistance other than dispersibility.
  • Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate
  • Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostea
  • the content of the surfactant is preferably 0.1 to 55 parts by weight, more preferably 0.1 to 45 parts by weight with respect to 100 parts by weight of the colorant.
  • the content of the resin-type dispersant is 0.1 parts by weight or more, the added effect is sufficiently obtained, and when the content is 55 parts by weight or less, the dispersion is very good.
  • One embodiment of the coloring composition may contain a photopolymerizable monomer.
  • the photopolymerizable monomer includes a monomer or oligomer that is cured by ultraviolet rays or heat to produce a transparent resin, and these can be used alone or in admixture of two or more.
  • the content of the photopolymerizable monomer is preferably 5 to 400 parts by weight with respect to 100 parts by weight of the colorant, and more preferably 10 to 300 parts by weight from the viewpoint of photocurability and developability. .
  • Monomers and oligomers that are cured by ultraviolet rays or heat to produce transparent resins include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate , Cyclohexyl (meth) acrylate, ⁇ -carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglyme Diether ether di (meth) acrylate
  • the colored composition of the present embodiment may contain a photopolymerization initiator.
  • a photopolymerization initiator When the composition is cured by ultraviolet irradiation and a filter segment is formed by photolithography, it can be prepared in the form of a solvent developing type or alkali developing type photosensitive coloring composition by adding a photopolymerization initiator or the like.
  • the content of the photopolymerization initiator is preferably 2 to 200 parts by weight with respect to 100 parts by weight of the colorant, and more preferably 3 to 150 parts by weight, for example, from the viewpoint of photocurability and developability. 5 to 150 parts by weight, 5 to 200 parts by weight, 10 to 150 parts by weight can be taken.
  • photopolymerization initiator examples include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1
  • Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as benzyl di
  • One embodiment of the coloring composition may contain a sensitizer.
  • Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetrapheny
  • Sensitizers can be used singly or in combination of two or more at any ratio as required.
  • the content of the sensitizer is preferably 3 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator contained in the coloring composition, and 5 to 50 parts by weight from the viewpoint of photocurability and developability. It is more preferable that
  • One embodiment of the coloring composition may contain a polyfunctional thiol that acts as a chain transfer agent.
  • the polyfunctional thiol may be a compound having two or more thiol groups. For example, hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene Glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, Pentaerythritol tetrakisthiopropionate, trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, 1,4-
  • the content of the polyfunctional thiol is preferably 0.1 to 30% by weight, more preferably 1 to 20% by weight, based on the weight (100% by weight) of the total solid content of the coloring composition.
  • the content of the polyfunctional thiol is 0.1% by weight or more, the effect of adding the polyfunctional thiol is sufficiently exhibited, and when it is 30% by weight or less, the sensitivity is in a good range and the resolution is increased.
  • One embodiment of the coloring composition may contain an antioxidant.
  • the antioxidant prevents the photopolymerization initiator and thermosetting compound contained in the colored composition from oxidizing and yellowing due to the thermal process during thermal curing and ITO annealing. can do. Therefore, by including an antioxidant, yellowing due to oxidation during the heating step can be prevented, and a high coating film transmittance can be obtained.
  • the “antioxidant” may be a compound having an ultraviolet absorbing function, a radical scavenging function, or a peroxide decomposing function.
  • an antioxidant a hindered phenol type, a hindered amine type, a phosphorus type is used.
  • Sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylate-based, and triazine-based compounds, and known ultraviolet absorbers and antioxidants can be used.
  • a hindered phenol antioxidant a hindered amine antioxidant, a phosphorus antioxidant, or a sulfur antioxidant is preferable from the viewpoint of achieving both transmittance and sensitivity of the coating film.
  • Agents More preferably, they are hindered phenolic antioxidants, hindered amine antioxidants, or phosphorus antioxidants.
  • antioxidants can be used singly or as a mixture of two or more at any ratio as required. Further, when the content of the antioxidant is 0.5 to 5.0% by weight based on the solid content weight of the coloring composition (100% by weight), the brightness and sensitivity are more preferable.
  • One embodiment of the coloring composition may contain an amine-based compound that functions to reduce dissolved oxygen.
  • amine compounds examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate.
  • examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.
  • ⁇ Leveling agent> In one embodiment of the coloring composition, it is preferable to add a leveling agent in order to improve the leveling property of the composition on the transparent substrate.
  • a leveling agent dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable.
  • dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by BYK Chemie.
  • Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie.
  • Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination.
  • the leveling agent content is preferably 0.003 to 0.5% by weight based on the total weight of the coloring composition (100% by weight).
  • a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule. Specifically, although it has a hydrophilic group, its solubility in water is small, and when added to a colored composition, its surface tension reducing ability is low, and even though it has low surface tension reducing ability, it can be applied to a glass plate. Those having good wettability and capable of sufficiently suppressing the chargeability at an addition amount that does not cause defects in the coating film due to foaming are preferable.
  • dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
  • the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used.
  • Dimethylpolysiloxanes having polyalkylene oxide units are commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
  • ⁇ Anionic, cationic, nonionic or amphoteric surfactants can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
  • anionic surfactant examples include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, monoethanolamine laurylsulfate , Lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, and the like.
  • Nonionic surfactants include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate, etc.
  • amphoteric surfactants such as alkylbetaines such as alkyldimethylaminoacetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.
  • One embodiment of the coloring composition may contain a curing agent, a curing accelerator, and the like as necessary in order to assist the curing of the thermosetting resin.
  • a curing agent phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Of these, compounds having two or more phenolic hydroxyl groups in one molecule and amine curing agents are preferred.
  • the curing accelerator examples include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl- N, N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (eg, triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (eg, dimethylamine, etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg, imidazole) 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2-ethyl -4-methylimidazole, etc.), phospho
  • One embodiment of the coloring composition may contain other additive components as necessary.
  • a storage stabilizer can be included to stabilize the viscosity of the composition over time.
  • adhesion improving agents such as a silane coupling agent, can also be contained.
  • Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned.
  • the storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the colorant.
  • adhesion improver examples include vinyl silanes such as vinyl tris ( ⁇ -methoxyethoxy) silane, vinyl ethoxy silane and vinyl trimethoxy silane, (meth) acryl silanes such as ⁇ -methacryloxypropyl trimethoxy silane, ⁇ - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) methyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, N- ⁇ (aminoethyl) ⁇ -aminopropyltrime
  • a colored composition (hereinafter also referred to as a pigment dispersion) comprises a colorant in a colorant carrier such as a binder resin and / or solvent, preferably together with a dispersion aid, kneader, It can be produced by finely dispersing using various dispersing means such as a roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor. At this time, when two or more colorants are included, two or more colorants may be simultaneously dispersed in the colorant carrier, or those separately dispersed in the colorant carrier may be mixed. In addition, if the colorant has high solubility, specifically, it is highly soluble in the solvent to be used, and if it is dissolved by stirring and no foreign matter is confirmed, it is necessary to manufacture by finely dispersing as described above. There is no.
  • the solvent development type or alkali development type coloring composition includes the pigment dispersion, a photopolymerizable monomer and / or a photopolymerization initiator, and, if necessary, a solvent, other dispersion aids, and additives. Can be mixed and adjusted.
  • the photopolymerization initiator may be added at the stage of preparing the colored composition, or may be added later to the prepared colored composition.
  • One embodiment of the coloring composition is a coarse particle having a size of 5 ⁇ m or more, preferably a coarse particle having a size of 1 ⁇ m or more, more preferably a coarse particle having a size of 0.5 ⁇ m or more by means of centrifugation, filtration with a sintered filter or a membrane filter. It is preferable to remove the mixed dust.
  • a coloring composition does not contain a particle
  • a color filter comprises a filter segment formed using one embodiment of a colored composition.
  • Examples of the color filter include those having a red filter segment, a green filter segment, and a blue filter segment.
  • the color filter may further include a magenta filter segment, a cyan filter segment, and a yellow filter segment.
  • One embodiment of the colored composition is preferably used to form a red, green, or yellow filter segment, and particularly preferably used for a green filter segment.
  • the color filter only needs to have at least one filter segment formed from the colored composition of one embodiment of the present invention, and filters of other colors that do not use the colored composition of one embodiment of the present invention.
  • a conventionally well-known thing can be used for the coloring agent used for formation of a segment.
  • Examples of colorants used for the red filter segment include C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 146, 149, 166, 168, 169, 176, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 221, 242, 246, 254, 255, 264, 270, 272, 273, 274 Mention may be made of red pigments such as 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286 or 287.
  • red pigments such as 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286 or 287.
  • red dyes such as xanthene, azo, disazo, and anthraquinone can be used.
  • red dyes such as xanthene, azo, disazo, and anthraquinone
  • C.I. I. Examples thereof include salt-forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338.
  • an orange colorant and / or a yellow colorant can be used in combination with the red filter segment.
  • colorants used for the green filter segment include C.I. I. And green pigments such as CI Pigment Green 7, 36, 37, 58. Blue pigments such as aluminum phthalocyanine pigments can also be used.
  • a yellow colorant can be used in combination with the green filter segment, and specifically includes the yellow colorant described in the description of the red filter segment.
  • colorants used for the blue filter segment include C.I. I. And blue pigments such as CI Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, and the like.
  • a purple pigment can be used in combination.
  • purple pigments that can be used in combination include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 27, 29, 30, 31, 32, Mention may be made of purple pigments such as 37, 39, 40, 42, 44, 47, 49 and 50.
  • a basic dye or a salt-forming compound of an acid dye exhibiting blue or purple can be used. When the dye is used, a triarylmethane dye or a xanthene dye is preferable in terms of lightness.
  • One embodiment of the color filter can be manufactured by a printing method or a photolithography method.
  • the formation of the filter segment by the printing method allows patterning by simply repeating the printing and drying of the coloring composition prepared as a printing ink, and therefore, as a method for producing a color filter, it is low in cost and excellent in mass productivity. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.
  • the colored composition prepared as a solvent developing type or alkali developing type colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. By the method, it is applied so that the dry film thickness is 0.2 to 5 ⁇ m. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.
  • an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used.
  • an antifoamer and surfactant can also be added to a developing solution.
  • a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.
  • the color filter can be manufactured by an electrodeposition method, a transfer method, an ink jet method or the like in addition to the above method.
  • the electrodeposition method is a method for producing a color filter by electrodepositing each color filter segment on a transparent conductive film by electrophoresis of colloidal particles using a transparent conductive film formed on a substrate.
  • the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.
  • a black matrix can be formed in advance before forming each color filter segment on a transparent substrate or a reflective substrate.
  • a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto.
  • a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment may be formed.
  • an overcoat film, a transparent conductive film, or the like is formed on one embodiment of the color filter as necessary.
  • the color filter is bonded to the counter substrate using a sealant, and after injecting liquid crystal from the injection port provided in the seal part, the injection port is sealed, and if necessary, a polarizing film or a retardation film is placed outside the substrate.
  • a liquid crystal display panel is manufactured by bonding.
  • Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convented bend (OCB). It can be used in a liquid crystal display mode in which colorization is performed using a color filter such as the above.
  • an average primary particle diameter and the identification of the compound were performed as follows. ⁇ Average primary particle diameter of colorant> The average primary particle diameter of the colorant was measured by a method of directly measuring the size of primary particles from an electron micrograph using a transmission (TEM) electron microscope. Specifically, the short axis diameter and the long axis diameter of the primary particles of each colorant were measured, and the average was used as the particle diameter of the colorant primary particles.
  • TEM transmission
  • the volume (weight) of each particle was determined by approximating the determined particle size cube, and the volume average particle size was defined as the average primary particle size.
  • the compound was identified by using a MALDI mass spectrometer autoflex III (hereinafter referred to as TOF-MS) manufactured by Bruker Daltonics, Inc., with the coincidence between the molecular ion peak of the obtained mass spectrum and the mass number obtained by calculation. .
  • Embodiment I Before, prior to Examples, a method for producing the pigment derivative (1) and the blue colorant 1 (B-1) used in the colored composition will be described.
  • This slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine (AlPc—Cl). Further, 100 parts of chloroaluminum phthalocyanine was slowly added to 1200 parts of concentrated sulfuric acid at room temperature in a reaction vessel. The mixture was stirred at 40 ° C. for 3 hours, and the sulfuric acid solution was poured into 24000 parts of cold water at 3 ° C. The blue precipitate was filtered, washed with water, and dried to obtain 102 parts of hydroxyaluminum phthalocyanine (AlPc—OH).
  • hydroxyaluminum phthalocyanine (AlPc-OH) 100 parts of hydroxyaluminum phthalocyanine (AlPc-OH), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 6 hours.
  • the kneaded product was poured into 3000 parts of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. all day and night.
  • 98 parts of colorant (B-1) were obtained.
  • the average primary particle size was 31.2 nm.
  • Example 1 (Production of yellow colorant 1 (Y-1)) Compound (1) was obtained according to the synthesis method described in JP-A-2008-81666.
  • Example 2 (Production of yellow colorant 2 (Y-2)) 70 parts of quinophthalone compound (a), C.I. I. 30 parts of Pigment Yellow 138 (“Pariotol Yellow K0960-HD” manufactured by BASF), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours. Next, the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 97 parts of yellow colorant 2 (Y-2) were obtained. The average primary particle size was 30.4 nm.
  • Example 3 (Production of yellow colorant 3 (Y-3)) 70 parts of quinophthalone compound (a) and C.I. I. 30 parts of Pigment Yellow 138 (“Pariotol Yellow K0960-HD” manufactured by BASF) was added to 50 parts of quinophthalone compound (a) and C.I. I. Pigment Yellow 138 (“Pariotol Yellow K0960-HD” manufactured by BASF) was changed in the same manner as in the production of Yellow Colorant 2 (Y-2), except that Yellow Colorant 3 (Y-3) was used. Obtained. The average primary particle size was 29.6 nm.
  • Example 4 (Production of yellow colorant 4 (Y-4)) 70 parts of quinophthalone compound (a) and C.I. I. 30 parts of Pigment Yellow 138 (“Pariotole Yellow K0960-HD” manufactured by BASF) was added to 20 parts of Cinophthalone Compound (a) and C.I. I. Pigment Yellow 138 (“Pariotol Yellow K0960-HD” manufactured by BASF) was changed to 80 parts except that Yellow Colorant 2 (Y-2) was produced. Obtained. The average primary particle size was 31.8 nm.
  • Example 5 (Production of yellow colorant 5 (Y-5)) Except for changing 70 parts of 2,3-naphthalenedicarboxylic anhydride to a mixture of 42 parts of 2,3-naphthalenedicarboxylic anhydride and 60 parts of tetrachlorophthalic anhydride, the yellow colorant (Y-1) In the same manner as in the production, yellow colorant 5 (Y-5) comprising a mixture of quinophthalone compound (a) and Pigment Yellow 138 was obtained. The average primary particle size was 28.0 nm. As a result of TOF-MS measurement, the composition ratio of the quinophthalone compound (a) and pigment yellow 138 in the yellow colorant 5 was 5: 5.
  • Example 6 (Production of yellow colorant 6 (Y-6)) To 200 parts of methyl benzoate, 35 parts of 8-aminoquinaldine, 33 parts of 2,3-naphthalenedicarboxylic anhydride, 47 parts of tetrachlorophthalic anhydride and 154 parts of benzoic acid are added, heated to 180 ° C., 2 Stir for hours. Subsequently, 95 parts of tetrachlorophthalic anhydride and 50 parts of benzoic acid were added and stirred at 180 ° C. for 3 hours. Furthermore, after cooling to room temperature, the reaction mixture was added to 6140 parts of acetone and stirred at room temperature for 1 hour.
  • the product was filtered off, washed with methanol, and dried to obtain 125 parts of a quinophthalone compound.
  • the yellow colorant 6 was composed mainly of a composition ratio of about 5: 5 between the quinophthalone compound (a) and Pigment Yellow 138. Further, a very small amount of molecular ion peak corresponding to the mass number of the quinophthalone compound (c) was observed, suggesting that a very small amount of the quinophthalone compound (c) was contained.
  • Example 7 (Production of yellow colorant 7 (Y-7)) To 200 parts of methyl benzoate, 40 parts of 8-aminoquinaldine, 150 parts of 2,3-naphthalenedicarboxylic anhydride and 154 parts of benzoic acid were added, heated to 180 ° C., and stirred for 4 hours. Further, after cooling to room temperature, the reaction mixture was added to 5440 parts of acetone and stirred at room temperature for 1 hour. The product was separated by filtration, washed with methanol, and dried to obtain 116 parts of quinophthalone compound (c). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (c).
  • quinophthalone compound (c) 100 parts of the obtained quinophthalone compound (c), 1200 parts of sodium chloride and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • Y-7 yellow colorant 7
  • Example 8 (Production of yellow colorant 8 (Y-8)) Using the quinophthalone compound (c) as a raw material, the compound (2) was obtained by the same method as the synthesis of the compound (1) according to the synthesis method described in JP-A-2008-81666.
  • quinophthalone compound (b) 100 parts of the obtained quinophthalone compound (b), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • 98 parts of yellow colorant 8 (Y-8) were obtained.
  • the average primary particle size was 31.1 nm.
  • Example 9 (Production of yellow colorant 9 (Y-9)) Yellow colorant 9 (Y-9) was obtained in the same manner as in the production of yellow colorant 3 (Y-3), except that 50 parts of quinophthalone compound (a) was changed to 50 parts of quinophthalone compound (b). .
  • the average primary particle size was 30.2 nm.
  • Example 10 (Production of yellow colorant 10 (Y-10)) Except that 70 parts of 2,3-naphthalenedicarboxylic anhydride was changed to 70 parts of 1,2-naphthalenedicarboxylic anhydride, the same procedure as in the production of yellow colorant 1 (Y-1) was carried out, and the quinophthalone compound (d Yellow colorant 10 (Y-10) was obtained.
  • the average primary particle size was 31.6 nm.
  • Example 11 (Production of yellow colorant 11 (Y-11)) To 300 parts of methyl benzoate, 100 parts of compound (2), 176 parts of tetrabromophthalic anhydride, and 143 parts of benzoic acid were added, heated to 180 ° C., and reacted for 6 hours. The formation of the quinophthalone compound (h) and the disappearance of the starting compound (2) were confirmed by TOF-MS. Furthermore, after cooling to room temperature, the reaction mixture was added to 7190 parts of acetone and stirred at room temperature for 1 hour. The product was filtered off, washed with methanol, and dried to obtain 138 parts of quinophthalone compound (h). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (h).
  • quinophthalone compound (h) 100 parts of the obtained quinophthalone compound (h), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • 97 parts of yellow colorant 11 (Y-11) were obtained.
  • the average primary particle size was 28.3 nm.
  • Example 12 (Production of yellow colorant 12 (Y-12)) 52 parts of the quinophthalone compound (a) was dissolved in 428 parts of 98% sulfuric acid and 472 parts of 25% fuming sulfuric acid and stirred at 85 ° C. for 2 hours to carry out sulfonation reaction. Next, this reaction solution was dropped into 6000 parts of ice water, and the precipitated quinophthalone compound was separated and washed with water to obtain a paste. The obtained paste was redispersed in 8000 parts of water and stirred at room temperature for 1 hour. After filtering off and washing with water, it was dried overnight at 80 ° C. to obtain 54 parts of a quinophthalone compound (k). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (k).
  • Example 13 (Production of yellow colorant 13 (Y-13)) 44 parts of the quinophthalone compound (b) were dissolved in 540 parts of 95% sulfuric acid, 38 parts of N-hydroxymethylphthalimide was added thereto, and the mixture was stirred at 85 ° C. for 7 hours. After cooling, the reaction solution was dropped into 3600 parts of ice water, and the precipitated quinophthalone compound was separated and washed with water to obtain a paste. The obtained paste was redispersed in 5000 parts of water and stirred at room temperature for 1 hour. After filtering off and washing with water, it was dried overnight at 80 ° C. to obtain 53 parts of a quinophthalone compound (r). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (r).
  • Example 14 (Production of yellow colorant 14 (Y-14)) C. I. 50 parts of Pigment Yellow 138 (“Pariotol Yellow K0960-HD” manufactured by BASF Corporation) I. A yellow colorant 14 (Y-14) was obtained in the same manner as in the production of yellow colorant 3 (Y-3), except that it was changed to 50 parts of Pigment Yellow 150 (“E4GN” manufactured by LANXESS). The average primary particle size was 36.5 nm.
  • an acrylic resin solution 2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • the weight average molecular weight of the acrylic resin is a polystyrene equivalent weight average molecular weight measured by GPC (gel permeation chromatography).
  • Example 15 (Preparation of Yellow Coloring Composition 1 (YP-1)) After stirring and mixing a mixture of the following components uniformly, using a zirconia bead having a diameter of 0.5 mm, an Eiger Mill (manufactured by Eiger Japan, “Mini” Model M-250 MKII ”) was dispersed for 5 hours, and then filtered through a 5 ⁇ m filter to produce yellow colored composition 1 (YP-1).
  • Eiger Mill manufactured by Eiger Japan, “Mini” Model M-250 MKII
  • Yellow colorant 1 (Y-1) 9.5 parts
  • Dye derivative (1) 0.5 part Resin type dispersant (“PB821” manufactured by Ajinomoto Fine Techno Co.) 1.0 part
  • Acrylic resin solution 1 45.0 parts Propylene glycol Monomethyl ether acetate 44.0 parts
  • Example 29 (Preparation of yellow coloring composition 15 (YP-15)) After stirring and mixing the mixture consisting of the following components uniformly, using a zirconia bead having a diameter of 0.5 mm, the mixture was dispersed for 5 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan). A yellow colored composition 15 (YP-15) was produced by filtration through a 5 ⁇ m filter.
  • Yellow colorant 1 (Y-1) 10.0 parts Resin type dispersant (“PB821” manufactured by Ajinomoto Fine Techno Co., Ltd.) 2.0 parts Acrylic resin solution 1 40.0 parts Propylene glycol monomethyl ether acetate 40.0 parts
  • the yellow colored composition was evaluated by preparing a coating film using the yellow colored composition and measuring the brightness, film thickness, and contrast ratio. The evaluation method is shown below.
  • the lightness (Y) of the obtained coating film was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.) and judged according to the following criteria.
  • the light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate.
  • the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate.
  • the light polarized by the polarizing plate passes through the coating film of the colored composition, scattering or the like occurs by the colorant particles, and when a part of the polarization plane is displaced, the polarizing plate is transmitted in parallel.
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate.
  • NPF-G1220DUN manufactured by Nitto Denko Corporation
  • the measurement was performed through a black mask having a 1 cm square hole in the measurement portion. Using the same coating film as the one subjected to lightness evaluation, the determination was made according to the following criteria.
  • Example 15 and Example 29, Example 16 and Example 30, Example 17 and Example 31, Example 18 and Example 32, Example 23 and Example 33 were compared, respectively, a yellow colored composition was obtained. It was revealed that when the pigment derivative (1) is contained, both the brightness and the contrast ratio are improved.
  • Preparation of green and blue coloring composition (Preparation of green coloring composition 1 (GP-1)) After stirring and mixing the mixture consisting of the following components uniformly, using a zirconia bead having a diameter of 0.5 mm, the mixture was dispersed for 5 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan). A green colored composition 1 (GP-1) was produced by filtration through a 5 ⁇ m filter.
  • Green colorant 1 (CI Pigment Green 58) 10.0 parts Resin type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin solution 1 45.0 parts Propylene glycol monomethyl ether acetate 44. 0 copies
  • Blue colorant 1 (B-1) 10.0 parts Resin type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin solution 1 45.0 parts Propylene glycol monomethyl ether acetate 44.0 parts
  • Yellow coloring composition 1 (YP-1) 18.4 parts Green coloring composition 1 (GP-1) 26.6 parts Acrylic resin solution 2 4.5 parts Photopolymerizable monomer (“Aronix M402 manufactured by Toagosei Co., Ltd.) ] 3.6 parts Photopolymerization initiator (“Irgacure 907" manufactured by Ciba Japan) 1.3 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Ethylene glycol monomethyl ether Acetate 45.4 parts
  • the photosensitive coloring composition is applied onto a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate by spin coating, then dried at 70 ° C. for 20 minutes, and ultraviolet rays are used at 300 mJ / cm 2 using an ultrahigh pressure mercury lamp. It exposed and developed with the alkaline developing solution of 23 degreeC.
  • an alkaline developer sodium carbonate 1.5% by weight, sodium bicarbonate 0.5% by weight, an anionic surfactant (“Perilox NBL” manufactured by Kao Corporation) 8.0% by weight, and water 90% by weight The thing which consists of was used. Furthermore, the coating film was obtained by heating at 230 degreeC for 30 minutes.
  • the brightness (Y) of the obtained coating film was measured and judged according to the following criteria.
  • the produced coating film was made to become the chromaticity (C light source) shown in Table 3 after the heat treatment at 230 ° C.
  • the contrast ratio of the coating film was measured by the same method as the contrast ratio measurement of the yellow colored compositions of Examples 15 to 33 and Reference Examples 4 to 9. The contrast ratio was calculated using the same coating film that was evaluated for brightness, and judged according to the following criteria.
  • Table 3 shows the evaluation results of the photosensitive coloring compositions prepared in Examples and Reference Examples.
  • Red Colorant 1 (C.I. Pigment Red 254) 8.5 parts Red Colorant 2 (C.I. Pigment Red 177) 3.5 parts Resin Type Dispersant ("EFKA4300" manufactured by Ciba Japan) 0 parts Acrylic resin solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • Red coloring composition 1 42.0 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 39.6 parts ethylene glycol monomethyl ether acetate
  • a colored coating was formed.
  • the coating was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • BR-1 blue photosensitive coloring composition 1
  • PGMAC propylene glycol monomethyl ether acetate
  • Weight average molecular weight of resin (Mw) The weight average molecular weight (Mw) of the resin was measured using HLC-8220GPC (manufactured by Tosoh Corporation) as an apparatus, TSK-GEL SUPER HZM-N connected in series as a column, and THF as a solvent. The molecular weight in terms of polystyrene.
  • an acrylic resin solution 2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • quinophthalone compound (a) represented by the following formula (50) and the disappearance of the starting compound (1) were confirmed by TOF-MS. Further, after cooling to room temperature, the reaction mixture was added to 3130 parts of acetone and stirred at room temperature for 1 hour. The product was filtered off, washed with methanol and dried to obtain 120 parts of quinophthalone compound (a). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (a).
  • the obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of yellow colorant 2 (PY-2) were obtained.
  • the average primary particle size was 31.3 nm.
  • quinophthalone compound (b) C.I. I. 60 parts of Pigment Yellow 138 (BASF “Pariol Yellow K0960-HD”), 1200 parts of sodium chloride and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours. .
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • 97 parts of yellow colorant 3 (PY-3) were obtained.
  • the average primary particle size was 36.8 nm.
  • This slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine. Further, 100 parts of chloroaluminum phthalocyanine was slowly added to 1200 parts of concentrated sulfuric acid at room temperature in a reaction vessel. The mixture was stirred at 40 ° C. for 3 hours, and the sulfuric acid solution was poured into 24000 parts of cold water at 3 ° C. The blue precipitate was filtered, washed with water and dried to obtain 102 parts of an aluminum phthalocyanine pigment represented by the following formula (53).
  • a blue colorant (PB-2) was obtained from the obtained aluminum phthalocyanine pigment represented by the formula (54) by the same salt milling method as that for the blue colorant (PB-1).
  • the average primary particle size was 31.2 nm.
  • a blue colorant (PB-4) was obtained from the obtained aluminum phthalocyanine pigment represented by formula (56) by the same salt milling method as that for the blue colorant (PB-1).
  • the average primary particle size was 33.0 nm.
  • a yellow colored composition (DY-2) was prepared in the same manner as in the preparation of the yellow colored composition (DY-1), except that the yellow colorant (PY-1) was changed to a yellow colorant (PY-2). Produced.
  • a yellow colored composition (DY-3) was prepared in the same manner except that the yellow colorant (PY-1) was changed to a yellow colorant (PY-3) in the preparation of the yellow colored composition (DY-1). Produced.
  • a yellow colored composition (DY-4) was prepared in the same manner except that the yellow colorant (PY-1) was changed to a yellow colorant (PY-4) in the production of the yellow colored composition (DY-1). Produced.
  • a yellow colored composition (DY-5) was prepared in the same manner as in the preparation of the yellow colored composition (DY-1) except that the yellow colorant (PY-1) was changed to a yellow colorant (PY-5). Produced.
  • the blue colored composition (DB-2) was prepared in the same manner except that the blue colorant (PB-1) was changed to the blue colorant (PB-2) in the production of the blue colored composition (DB-1). Produced.
  • the blue colored composition (DB-3) was prepared in the same manner except that the blue colorant (PB-1) was changed to the blue colorant (PB-3) in the production of the blue colored composition (DB-1). Produced.
  • the blue colored composition (DB-4) was prepared in the same manner except that the blue colorant (PB-1) was changed to the blue colorant (PB-4) in the production of the blue colored composition (DB-1). Produced.
  • a blue colored composition (DB-5) was prepared in the same manner except that the blue colorant (PB-1) was changed to the blue colorant (PB-5) in the production of the blue colored composition (DB-1). Produced.
  • Green coloring composition (DG-1) Using the yellow coloring composition (DY-1) and the blue coloring composition (DB-1), the green coloring composition (DG-1) was prepared by stirring and mixing with the following composition.
  • Yellow coloring composition (DY-1) 81.0 parts Blue coloring composition (DB-1) 19.0 parts
  • the obtained green coloring composition (DG-1) was applied onto a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater, dried at 70 ° C. for 20 minutes, and then at 230 ° C.
  • a coated substrate was prepared by heating and cooling for 1 hour.
  • Viscosity evaluation The viscosity of the coloring composition was measured at a rotation speed of 20 rpm using an E type viscometer (“ELD type viscometer” manufactured by Toki Sangyo Co., Ltd.) at 25 ° C. on the adjustment day. The results were judged according to the following criteria. ⁇ : Less than 10.0 [mPa ⁇ s] ⁇ : 10.0 or more and less than 13.0 [mPa ⁇ s] ⁇ : 13.0 or more [mPa ⁇ s]
  • the coloring power was evaluated by measuring the film thickness of the coating film.
  • the film thickness of the obtained coating film was measured using a surface shape measuring device “Dektak 8 (manufactured by Veeco)”. The results were judged according to the following criteria. It can be said that the smaller the film thickness that gives the desired chromaticity, the greater the coloring power, and the better.
  • Green photosensitive coloring composition (RG-1) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 1 ⁇ m filter to prepare a photosensitive green coloring composition (RG-1).
  • Green coloring composition (DG-1) 45.0 parts Acrylic resin solution 2 4.5 parts Photopolymerizable monomer 3.6 parts ("Aronix M402" manufactured by Toa Gosei Co., Ltd.) Photoinitiator (“Irgacure 907” manufactured by Ciba Japan) 1.3 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 45.4 parts
  • the green photosensitive coloring composition (RG-1 to 22) was applied onto a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, dried at 70 ° C. for 20 minutes, and an ultrahigh pressure mercury lamp was applied. Then, ultraviolet exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Subsequently, the coating-film board
  • the brightness: Y (c) was measured.
  • the light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate.
  • the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate.
  • the light polarized by the polarizing plate passes through the coating film of the colored composition, scattering or the like occurs by the colorant particles, and when a part of the polarization plane is displaced, the polarizing plate is transmitted in parallel.
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate.
  • NPF-G1220DUN manufactured by Nitto Denko Corporation
  • the measurement was performed through a black mask having a 1 cm square hole in the measurement portion.
  • the determination was made according to the following criteria. ⁇ : 4000 or more ⁇ : 3500 or more and less than 4000 ⁇ : less than 3500
  • the coloring power was evaluated by measuring the film thickness of the coating film using the same coating film as that for which the brightness was evaluated.
  • the film thickness of the obtained coating film was measured using a surface shape measuring device “Dektak 8 (manufactured by Veeco)”. The results were judged according to the following criteria. It can be said that the smaller the film thickness that gives the desired chromaticity, the greater the coloring power, and the better.
  • red photosensitive coloring composition (RR-1)) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a red colored composition (DR-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Red pigment (CI Pigment Red 254) 9.6 parts Red Pigment (CI Pigment Red 177) 2.4 parts
  • Resin-type dispersant (“EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • red photosensitive coloring composition (RR-1).
  • Red coloring composition (DR-1) 42.0 parts Acrylic resin solution 2 13.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts
  • Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured) 2.0 parts
  • Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a blue photosensitive coloring composition (RB-1).
  • Blue coloring composition (DB-6) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907", manufactured by 2.0) Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 part 45.1 parts ethylene glycol monomethyl ether acetate
  • a black matrix was patterned on a glass substrate, and a red photosensitive coloring composition (RR-1) was applied onto the substrate with a spin coater to form a colored coating.
  • the film was irradiated with ultraviolet rays of 150 mJ / cm 2 through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water, and the substrate was heated at 220 ° C. for 20 minutes.
  • the photosensitive coloring composition (RG-6) By using the photosensitive coloring composition (RG-6), it was possible to produce a color filter having high brightness, high contrast, and excellent coloring power.
  • the weight average molecular weight (Mw) is a polystyrene-equivalent molecular weight when using TSKgel column (manufactured by Tosoh Corporation) and GPC (manufactured by Tosoh Corporation, HLC-8320GPC) using DMF as a developing solvent. .
  • quinophthalone compound (c) 100 parts of the obtained quinophthalone compound (c), 1200 parts of sodium chloride and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • Y-6 yellow colorant 6
  • quinophthalone compound (b) 100 parts of the obtained quinophthalone compound (b), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • 98 parts of yellow colorant 7 (Y-7) were obtained.
  • the average primary particle size was 31.1 nm.
  • quinophthalone compound (h) 100 parts of the obtained quinophthalone compound (h), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded product is put into warm water, stirred for 1 hour while being heated to about 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight.
  • 97 parts of yellow colorant 9 (Y-9) were obtained.
  • the average primary particle size was 28.3 nm.
  • a reaction vessel 2 equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 6.08 parts of iminobispropylamine and 156.3 parts of propylene glycol monomethyl ether acetate and heated to 60 ° C.
  • the said prepolymer solution was dripped there over 30 minutes, and also, after reacting for 30 minutes, it cooled to room temperature and complete
  • propylene glycol monomethyl ether acetate was added to obtain a 30% non-volatile solution of the pigment dispersant (B-1).
  • the weight average molecular weight was about 10,000, and the theoretical amine value was 47 mg KOH / g.
  • IPDI isophorone diisocyanate
  • HDI hexamethylene diisocyanate
  • DBTDL dibutyltin dilaurate
  • IBPA iminobispropylamine [also known as N, N-bis (3-aminopropyl) amine]
  • MIBPA methyliminobispropylamine [also known as N, N-bis ( 3-aminopropyl) methylamine]
  • Comparative pigment dispersant B'-5 A cationic comb-shaped graft polymer having a basic group equivalent of 48 mgKOH / g in which the backbone polymer part is dimethylaminomethylated glycidyl methacrylate-methacrylate esterified glycidyl methacrylate copolymer and the branched polymer part is polymethylmethacrylate.
  • Non-volatile content 40% propylene glycol monomethyl ether acetate solution (Japanese Patent Laid-Open No. 9-176511: pigment dispersant described in Example 6)
  • ⁇ Preparation of binder resin> (Manufacture of binder resin (C-1)) 98.4 parts of propylene glycol monomethyl ether acetate is put in a reaction vessel, heated to 110 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 12.3 parts of methacrylic acid, 20 parts of butyl acrylate, 29.2 of benzyl methacrylate. 24.2 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M-110” manufactured by Toagosei Co., Ltd.) and 14.3 parts of 4-hydroxybutyl acrylate and 1.65 parts of AIBN were added dropwise over 2 hours. The polymerization reaction was carried out.
  • the binder resin had a weight average molecular weight of about 30,000 and a theoretical Tg of 2.1 ° C.
  • binder resins (C-2) to (C-4) The synthesis was performed in the same manner as the binder resin (C-1) except that the raw materials and the charge amounts shown in Table 4 were used, and propylene glycol monomethyl ether acetate was added to add binder resins (C-2) to (C-4). A 20% nonvolatile solution.
  • MMA methyl methacrylate nBA: butyl acrylate
  • BzMA benzyl methacrylate M-110: manufactured by Toagosei Co., Ltd.
  • Paracumylphenol ethylene oxide modified acrylate 4HBA 4-hydroxybutyl acrylate
  • HEMA 2-hydroxyethyl methacrylate
  • PME-400 Nippon Oil & Fats ( Methoxypolyethylene glycol methacrylate AIBN: 2,2'-azobis (isobutyronitrile)
  • Example 1 Preparation of yellow coloring composition 1 (YP-1)) After stirring and mixing the mixture consisting of the following components uniformly, using a zirconia bead having a diameter of 0.5 mm, the mixture was dispersed for 5 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan). The mixture was filtered through a 5 ⁇ m filter to produce yellow colored composition 1 (YP-1). Yellow colorant 1 (Y-1) 9.5 parts Dye derivative (1) 0.5 part Pigment dispersant (B-1) 6.7 parts Binder resin (C-1) 40.0 parts Propylene glycol monomethyl ether acetate 43.3 parts
  • the obtained yellow coloring composition (YP-1 to 43) was measured for viscosity characteristics, brightness and contrast ratio by the following methods. The evaluation results are shown in Table 5.
  • Viscosity characteristics Using the E-type viscometer (“ELD viscometer” manufactured by Toki Sangyo Co., Ltd.), the viscosity of the next day after preparing the yellow coloring composition (YP-1 to 43) (hereinafter referred to as initial viscosity) (hereinafter referred to as initial viscosity) (hereinafter referred to as initial viscosity) The measurement was performed at 25 ° C. under the condition of a rotation speed of 20 rpm. Moreover, the viscosity accelerated with time at 40 ° C. for 1 week (hereinafter referred to as viscosity with time) was measured, the rate of change in viscosity with time was calculated according to the following formula, and the stability with time was evaluated in the following four stages.
  • ELD viscometer E-type viscometer manufactured by Toki Sangyo Co., Ltd.
  • a yellow colored composition (YP-1 to 43) was applied onto a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater and heated at 230 ° C. for 20 minutes to obtain a coating film.
  • the coating conditions spin coater rotation speed and time
  • the lightness (Y) of the obtained coating film was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.) and judged according to the following criteria.
  • the light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate. At this time, if the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate.
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate.
  • NPF-G1220DUN manufactured by Nitto Denko Corporation
  • this embodiment is composed of a vinyl polymer containing a quinophthalone pigment and an ethylenically unsaturated monomer having at least one of an ethylene oxide chain or a propylene oxide chain in a copolymer composition.
  • the colored compositions of Examples 1 to 33 using the pigment dispersant had a low initial viscosity and a low rate of change in viscosity with time, and exhibited good stability. In addition, both of them resulted in high brightness and high contrast, indicating that they are excellent as coloring compositions for color filters.
  • the colored compositions of Reference Examples 1 to 3 and 6 to 8 using a pigment dispersant made of a vinyl polymer having no ethylene oxide chain or propylene oxide chain have an initial viscosity of Reference Example 1. Although it was low, the rate of change in viscosity with time was high, and it was low brightness and low contrast. In Reference Examples 2, 3, and 6 to 8, both the initial viscosity and the rate of change with time were high, and the brightness was low and the contrast was low. The same was applied to Reference Examples 4 and 5 using pigment dispersants having different structures.
  • Coloring compositions of Reference Examples 9 and 10 using a non-quinophthalone pigment and a pigment dispersant comprising a vinyl polymer containing an ethylenically unsaturated monomer having at least one of an ethylene oxide chain or a propylene oxide chain in a copolymer composition The product was satisfactory in contrast, but the brightness was inferior to the colored composition part of the example.
  • Yellow coloring composition 1 (YP-1) 18.4 parts
  • Green coloring composition (GP-1) 26.6 parts
  • Binder resin (C-4) 4.5 parts Photopolymerizable monomer (manufactured by Toagosei Co., Ltd.
  • the photosensitive coloring composition (GR1 to 43) was applied onto a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, dried at 70 ° C. for 20 minutes, and an ultrahigh pressure mercury lamp was applied. Then, ultraviolet exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Subsequently, it heated at 220 degreeC for 30 minute (s), and the coating-film board
  • the coating conditions spin coater rotation speed, time
  • y 0.600 in the C light source.
  • the lightness (Y) of the obtained coating film was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.) and judged according to the following criteria. ⁇ : 59.5 or more ⁇ : 58.0 or more to less than 59.5 ⁇ : less than 58.0
  • this embodiment is composed of a vinyl polymer containing a quinophthalone pigment and an ethylenically unsaturated monomer having at least one of an ethylene oxide chain or a propylene oxide chain in a copolymer composition.
  • the photosensitive coloring compositions of Examples 34 to 66 to which a yellow coloring agent using a pigment dispersant was added gave good results in brightness and contrast, and were shown to be excellent as a coloring composition for a color filter. It was.
  • the photosensitive coloring compositions of Reference Examples 11 to 20 using a pigment dispersant made of a vinyl polymer having no ethylene oxide chain or propylene oxide chain have both lightness and / or contrast. In result, it was inferior to the photosensitive coloring composition of Example. *
  • the red photosensitive coloring composition and the blue photosensitive coloring composition used for the color filter of this embodiment will be described.
  • the photosensitive coloring composition 1 (GR-1) of this embodiment was used.
  • Red coloring composition (Preparation of red coloring composition (RP-1)) A mixture of the following composition is uniformly stirred and mixed, and dispersed for 5 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then a 5 ⁇ m filter. And a red colored composition (RP-1) was produced.
  • Red coloring agent (CI Pigment Red 254) 8.5 parts Red coloring agent (CI Pigment Red 177) 3.5 parts
  • Resin type dispersant (“EFKA4300” manufactured by Ciba Japan) 1.0 part
  • Binder resin (C-4) 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • red photosensitive coloring composition (RR-1)) A mixture having the following composition was stirred and mixed to be uniform, and then filtered through a 1 ⁇ m filter to prepare a red photosensitive coloring composition (RR-1).
  • Red coloring composition (RP-1) 42.0 parts Binder resin (C-4) 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba ⁇ "Irgacure 907" manufactured by Japan Co., Ltd.) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 39.6 parts ethylene glycol monomethyl ether acetate
  • BR-1 blue photosensitive coloring composition
  • Blue coloring composition (BP-1) 34.0 parts Binder resin (C-4) 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba ⁇ "Irgacure 907" manufactured by Japan Co., Ltd.) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • a colored coating was formed.
  • the coating was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% aqueous sodium carbonate solution to remove the unexposed portion, and then the substrate was washed with ion-exchanged water. Formed.
  • Embodiment IV The measurement method of the weight average molecular weight (Mw) of the resin is as follows.
  • the weight average molecular weight (Mw) of the resin was measured in terms of polystyrene measured using TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent. It is a weight average molecular weight (Mw).
  • an acrylic resin solution 2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • quinophthalone compound (1) was obtained according to the synthesis method described in JP-A-2008-81666. As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (1).
  • the quinophthalone compound (2) is obtained by the same method as the synthesis of the quinophthalone compound (1) according to the synthesis method described in JP-A-2008-81666. It was. As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (2).
  • This slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine. Further, 100 parts of chloroaluminum phthalocyanine was slowly added to 1200 parts of concentrated sulfuric acid at room temperature in a reaction vessel. The mixture was stirred at 40 ° C. for 3 hours, and the sulfuric acid solution was poured into 24000 parts of cold water at 3 ° C. The blue precipitate was filtered, washed with water and dried to obtain 102 parts of aluminum phthalocyanine (1).
  • a salt milling process was performed. 100 parts of aluminum phthalocyanine (2), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. The kneaded product is put into warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. After repeated filtration and washing to remove sodium chloride and diethylene glycol, the mixture is dried at 80 ° C. for a whole day and night. BC-1) 98 parts were obtained. The average primary particle size was 31.2 nm.
  • ⁇ Method for producing green and blue coloring composition> (Preparation of green coloring composition (DG-1)) After stirring and mixing the mixture having the following composition to be uniform, using a zirconia bead having a diameter of 0.5 mm, using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After dispersing for 5 hours, the mixture was filtered with a 5 ⁇ m filter to prepare a green coloring composition (DG-1).
  • Green colorant (GC-1) 10.0 parts
  • Resin-type dispersant (“EFKA4300” manufactured by Ciba Japan) 2.0 parts
  • Acrylic resin solution 1 40.0 parts Propylene glycol monomethyl ether acetate 48.0 parts
  • Example 1 The manufacturing method of a yellow coloring composition> [Example 1] (Preparation of yellow coloring composition (DY-1)) After stirring and mixing the mixture having the following composition to be uniform, using a zirconia bead having a diameter of 0.5 mm, using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After dispersing for 5 hours, the mixture was filtered through a 5 ⁇ m filter to produce a yellow colored composition (DY-1).
  • the yellow coloring composition (DY-1 to 38) was applied on a glass substrate having a thickness of 100 mm ⁇ 100 mm and a thickness of 1.1 mm using a spin coater, then dried at 70 ° C. for 20 minutes, and then at 220 ° C. for 20 minutes.
  • a coated substrate was prepared by heating and cooling for a minute. The prepared coated substrate was subjected to heat treatment at 220 ° C. so that the transmittance at 450 nm became 5%, and a spectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.) was used for spectroscopic analysis at 500 nm and 550 nm. The transmittance was measured.
  • the spectral transmittances at 500 nm and 550 nm were determined according to the following criteria. ⁇ : 99% or more ⁇ : 97 or more, less than 99% ⁇ : less than 97%
  • the light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate.
  • the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate.
  • the light polarized by the polarizing plate passes through the coating film of the colored composition, scattering or the like occurs by the colorant particles, and when a part of the polarization plane is displaced, the polarizing plate is transmitted in parallel.
  • the contrast ratio was determined according to the following criteria. ⁇ : 3000 or more ⁇ : 2000 or more and less than 3000 ⁇ : less than 2000
  • the yellow coloring composition (DY-1 to 38) was applied on a glass substrate having a thickness of 100 mm ⁇ 100 mm and a thickness of 1.1 mm using a spin coater, then dried at 70 ° C. for 20 minutes, and then at 220 ° C. for 20 minutes.
  • a coated substrate was prepared by heating and cooling for a minute.
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.).
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 ) ⁇ : ⁇ Eab * is less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more and less than 10.0 ⁇ : ⁇ Eab * is 10.0 or more
  • a coated substrate is prepared in the same manner as in the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) with a C light source is measured with a microspectrophotometer ( Measurement was performed using “OSP-SP100” manufactured by Olympus Optical Co., Ltd.
  • an ultraviolet cut filter (“COLORED OPTICAL GLASS L38” manufactured by Hoya Co., Ltd.) is attached on the substrate, and irradiated with ultraviolet rays using a 470 W / m 2 xenon lamp for 100 hours, and then the chromaticity ([ L * (2), a * (2), b * (2)]) were measured, and the color difference ⁇ Eab * was determined by the above formula and evaluated according to the same criteria as for heat resistance.
  • the coloring composition was excellent in spectral transmittance, contrast ratio, and coloring power, and the heat resistance and light resistance of the coating film were satisfactory.
  • the yellow coloring compositions (DY-34 to 36) of Reference Examples 1 to 3 had low brightness.
  • the yellow coloring compositions (DY-37, 38) of Reference Examples 4 and 5 used in combination with I. Pigment Yellow 138 had good brightness but a low contrast ratio.
  • the yellow coloring composition (DY-34) of Reference Example 1 using I. Pigment Yellow 138 alone had a problem of low coloring power in addition to low brightness.
  • the yellow coloring compositions (DY-35, 36) of Reference Examples 2 and 3 using Disperse Yellow 64 had poor contrast ratio, heat resistance and light resistance.
  • Green photosensitive coloring composition (RG-1) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 1.0 ⁇ m filter to obtain a green photosensitive coloring composition (RG-1).
  • Green coloring composition (DG-1) 23.5 parts Yellow coloring composition (DY-1) 21.5 parts Acrylic resin solution 2 2.0 parts
  • Photopolymerizable monomer (“Aronix M402” manufactured by Toagosei Co., Ltd.)
  • Photopolymerization initiator (“Irgacure OXE02" manufactured by Ciba Japan) 1.2 parts Cyclohexanone 20.0 parts Propylene glycol monomethyl ether acetate 27.4 parts
  • the green photosensitive coloring composition (RG-1 to 47) was applied onto a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, and then dried at 70 ° C. for 20 minutes to obtain ultrahigh pressure mercury. Using a lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Then, after heating at 220 ° C. for 20 minutes and allowing to cool, the brightness Y (C) of the obtained coated substrate was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.).
  • OSP-SP100 microspectrophotometer
  • an alkali developer sodium carbonate 1.5% by weight, sodium hydrogen carbonate 0.5% by weight, an anionic surface active agent (“Perex NBL” manufactured by Kao Corporation) 8.0% by weight and water 90% by weight was used.
  • the brightness value was determined according to the following criteria. ⁇ : 60.5 or more ⁇ : 58.5 or more, less than 60.5 ⁇ : less than 58.5
  • Contra ratio evaluation About the measuring method of the contrast ratio of a coating film, it measured by the method similar to the contrast ratio measurement of a yellow coloring composition. The contrast ratio was calculated using the same coating film that was evaluated for brightness, and judged according to the following criteria. ⁇ : 3500 or more ⁇ : 3000 or more and less than 3500 ⁇ : less than 3000
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 230 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ⁇ Eab * was determined and evaluated in the following three stages.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 ) ⁇ : ⁇ Eab * is less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more and less than 10.0 ⁇ : ⁇ Eab * is 10.0 or more
  • a coated substrate is prepared in the same manner as in the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) with a C light source is measured with a microspectrophotometer ( Measurement was performed using “OSP-SP100” manufactured by Olympus Optical Co., Ltd.
  • an ultraviolet cut filter (“COLORED OPTICAL GLASS L38” manufactured by Hoya Co., Ltd.) is attached on the substrate, and irradiated with ultraviolet rays using a 470 W / m 2 xenon lamp for 100 hours, and then the chromaticity ([ L * (2), a * (2), b * (2)]) were measured, and the color difference ⁇ Eab * was determined by the above formula and evaluated according to the same criteria as for heat resistance.
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 220 ° C. for 20 minutes in a clean oven.
  • the pattern film thickness in the 100 ⁇ m photomask portion of the filter segment formed by the above method was measured, and the minimum exposure amount that was 90% or more with respect to the film thickness after coating was determined according to the following criteria. It can be said that the smaller the minimum exposure, the higher the sensitivity and the better the photosensitive coloring composition. ⁇ : Less than 50 mJ / cm 2 ⁇ : 50 mJ / cm 2 or more, less than 100 mJ / cm 2 ⁇ : 100 mJ / cm 2 or more
  • the green color of the example containing the quinophthalone pigment represented by the general formula (1) and the quinophthalone dye represented by the general formula (6) as the colorant that is a feature of the present embodiment was excellent in lightness, contrast ratio, and coloring power, and the heat resistance and light resistance of the coating film were satisfactory. Furthermore, despite the fact that it contains a dye, the sensitivity was also good.
  • the green photosensitive coloring compositions (RG-38 and 43) of Reference Examples 6 and 11 using I. Pigment Yellow 138 alone had low coloring power.
  • the green photosensitive coloring compositions (RG-41, 42, 46, and 47) of Reference Examples 9, 10, 14, and 15 used in combination with I. Pigment Yellow 138 have good brightness but low contrast ratios. The result was poor sensitivity.
  • C.I. which is not a quinophthalone dye [B].
  • the green photosensitive coloring compositions of Reference Examples 7, 8, 12, and 13 (RG-39, 40, 44, and 45) using Disperse Yellow 64 had bad results in all properties.
  • red photosensitive coloring composition (RR-1)) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a red colored composition (DR-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Red pigment (CI Pigment Red 254) 9.6 parts Red Pigment (CI Pigment Red 177) 2.4 parts
  • Resin-type dispersant (“EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • red photosensitive coloring composition (RR-1).
  • Red coloring composition (DR-1) 42.0 parts Acrylic resin solution 2 13.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts
  • Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured) 2.0 parts
  • Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a blue photosensitive coloring composition (RB-1).
  • Blue coloring composition (DB-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907", manufactured by 2.0) Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 part 45.1 parts ethylene glycol monomethyl ether acetate
  • a black matrix was patterned on a glass substrate, and a red photosensitive coloring composition (RR-1) was applied onto the substrate with a spin coater to form a colored coating.
  • the film was irradiated with ultraviolet rays of 150 mJ / cm 2 through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 220 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • a blue photosensitive coloring composition RB-1
  • quinophthalone dye 15 parts are mixed with 20 parts of N, N-dimethylacetamide, 0.3 parts of sodium hydroxide and 1.8 parts of 2-ethylhexyl 4-bromobutyric acid are further mixed and stirred at 90 ° C. for 1 hour did.
  • 100 parts of methanol and 100 parts of water were added and stirred for 1 hour.
  • the precipitated solid was collected by suction filtration. Further, the solid was put into 100 parts of methanol, stirred for 1 hour, and then collected by suction filtration. Drying overnight in a vacuum dryer (40 ° C.) gave 1.6 parts of product. The yield was 51%.
  • quinophthalone dye 15 parts are mixed with 20 parts of N, N-dimethylacetamide, 0.3 parts of sodium hydroxide, 2- (2- (2-ethylhexyloxy) ethoxy) ethyl-5-bromopentanoate 2 .5 parts were further mixed and stirred at 100 ° C. for 2 hours. After allowing to cool, the reaction solution was added to 50 parts of water, and further 100 parts of chloroform was added to extract the organic layer. Magnesium sulfate was added to the organic layer, dried, filtered and concentrated under reduced pressure.
  • quinophthalone dye 15 ⁇ ⁇ 2.0 parts of quinophthalone dye 15 ⁇ ⁇ is mixed with 20 parts of N, N-dimethylacetamide, 0.3 parts of sodium hydroxide, bis (2-ethylhexyl) 7-oxabicyclo [4,1,0] heptane-3,4 -9.7 parts of diloxylate were further mixed and stirred at 150 ° C for 10 hours. After allowing to cool, the reaction solution was added to 50 parts of water, and further 100 parts of chloroform was added to extract the organic layer. Magnesium sulfate was added to the organic layer, dried, filtered and concentrated under reduced pressure.
  • Disperse Yellow 54 was used.
  • Disperse Yellow 64 was used.
  • the polymerization average molecular weight (Mw) of the acrylic resin was measured using a TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent.
  • the weight average molecular weight (Mw) in terms of polystyrene was measured using a TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent.
  • Phthalocyanine blue pigment C.I. I. Pigment Blue 15: 6 (“LIONOL BLUE ES” manufactured by Toyo Ink Manufacturing Co., Ltd.) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. did. Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of blue pigment 1 were obtained. The average primary particle diameter of the obtained pigment was 79 nm.
  • Phthalocyanine green pigment C.I. I. Pigment Green 58 (“FASTGEN GREEN A110” manufactured by DIC Corporation) was used as it was on the market.
  • the average primary particle diameter of the green pigment 1 was 22 nm.
  • red pigment 1 Anthraquinone red pigment C.I. I. 200 parts of Pigment Red 177 (“Chromophthalred A2B” manufactured by Ciba Japan), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of red pigment 1 were obtained. The average primary particle diameter of the obtained pigment was 54 nm.
  • colored compositions Q-2 to 24 were prepared in the same manner as colored composition Q-1, except that quinophthalone dye 1 was replaced with the quinophthalone dye shown in Table 2.
  • colored compositions DP-2 to 8 were produced in the same manner as the colored composition DP-1, except that the blue pigment 1 was replaced with the pigment shown in Table 3.
  • Examples 1 to 20, Reference Examples 1 to 7 ⁇ Coating foreign matter test of colored compositions Q-1 to 24 and DP-5 to 7> The evaluation was performed by preparing a test substrate and counting the number of particles. The coloring composition was applied onto the transparent substrate so that the dried coating film was about 2.0 ⁇ m, and heated in an oven at 230 ° C. for 20 minutes to obtain a test substrate. The evaluation was carried out using a Olympus system metal microscope “BX60”). The magnification is 500 times, and the number of particles that can be observed in any five fields of view through transmission is counted.
  • Examples 1 to 20 gave good results with few coating film foreign matters. In addition, Examples 1 to 20 were the results of excellent spectral characteristics, and showed spectral shapes with high brightness. Reference Examples 2 to 6 showed spectral shapes in which the transmittance at 550 nm was relatively good, but the transmittance at 500 nm was low and no improvement in brightness was expected.
  • Reference Examples 1 to 4 using a dye having a hydroxyl group in the quinoline ring are compared with the spectral shapes of Examples 1 to 20 using a dye having no hydroxyl group (for example, Example 5 in FIG. 1, Reference Examples 1 and 3).
  • the dye having a low transmittance at 500 nm and having a hydroxyl group in the quinoline ring is a dye that cannot be expected to improve brightness.
  • Example 21 ⁇ Adjustment of resist material G-1> The following mixture was stirred and mixed to be uniform and then filtered through a 1.0 ⁇ m filter to obtain a green resist material (G-1). Colored composition (DP-3): 18.0 parts Colored composition (Q-1): 42.0 parts previously prepared acrylic resin solution: 11.0 parts Trimethylolpropane triacrylate: 4.2 parts (new Nakamura Chemical Co., Ltd.
  • NK ESTER ATMPT Photopolymerization initiator
  • Senitizer EAB-F
  • PGMAC propylene glycol monomethyl ether acetate
  • ⁇ Coating foreign matter test> A resist material was applied on the transparent substrate so that the dried coating film became about 2.5 ⁇ m, and the whole surface was exposed to ultraviolet light, and then heated in an oven at 230 ° C. for 20 minutes and allowed to cool to obtain an evaluation substrate. The evaluation was performed by observing the surface using a metal microscope “BX60” manufactured by Olympus System. The magnification is 500 times, and the number of particles that can be confirmed in any five visual fields through transmission is counted. In the following evaluation results, ⁇ and ⁇ are good, ⁇ is a level that does not cause a problem in use although there are many foreign matters, and ⁇ indicates coating unevenness due to the foreign matters. ⁇ ⁇ : Less than 5 ⁇ : 5 or more, less than 20 ⁇ : 20 or more, less than 100 ⁇ : 100 or less, Table 7 shows the results.
  • ⁇ Film heat resistance test> A resist material is applied on a transparent substrate so that the dry coating thickness is about 2.5 ⁇ m, and after UV exposure through a mask having a predetermined pattern, an alkali developer is sprayed to remove uncured parts. Thus, a desired pattern was formed. Then, after heating in an oven at 230 ° C. for 20 minutes and allowing to cool, the chromaticity 1 (L * (1), a * (1), b * (1)) of the obtained coating film with a C light source is microspectrophotometric. Measurement was performed using a meter (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.). Further, as a heat resistance test, the sample was heated in an oven at 230 ° C.
  • OSP-SP200 manufactured by Olympus Optical Co., Ltd.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2+ (a * (2)-a * (1)) 2+ (b * (2)-b * (1)) 2) :: ⁇ Eab * is less than 1.5 ⁇ : ⁇ Eab * is 1.5 or more and less than 3.0 ⁇ : ⁇ Eab * is 3.0 or more and less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more, Table 7 The results are shown in.
  • ⁇ Film resistance test> A test substrate was prepared in the same procedure as the coating heat resistance test, and the chromaticity 1 (L * (1), a * (1), b * (1)) with a C light source was measured with a microspectrophotometer (Olympus Optics). Measurement was performed using “OSP-SP200” manufactured by the company. Thereafter, the substrate was immersed in N-methylpyrrolidone for 30 minutes. After removing the substrate, measure chromaticity 2 (L * (2), a * (2), b * (2)) with a C light source, and calculate the color difference ⁇ Eab * in the same manner as the coating film heat resistance test. Then, the solvent resistance of the coating film was evaluated according to the same criteria as the coating film heat resistance test. Moreover, if evaluation is more than (triangle
  • the resist materials (G-1 to 20, G-22 to 41, R-1 to 3, Y-1 to 3) of Examples 21 to 66 have brightness (Y), coating film foreign matter, heat resistance, light resistance, Good results in solvent resistance were shown.
  • the resist materials (G-44 and G-45) of Reference Examples 11 and 12 are difficult to actually use because of their poor heat resistance and light resistance.
  • the resist materials (G-21, G-43 to 46, R-4, Y-4) of Reference Examples 8 to 15 had lower brightness (Y) than the examples.
  • a transparent ITO electrode layer was formed on the obtained RGB color filter, and a polyimide alignment layer was formed thereon.
  • a color display device was produced on the other surface of this glass substrate in combination with a three-wavelength CCFL light source of a polarizing plate. Formed.
  • a TFT array and a pixel electrode were formed on one surface of another (second) glass substrate, and a polarizing plate was formed on the other surface.
  • the two glass substrates prepared in this way are arranged facing each other so that the electrode layers face each other, and are aligned using spacer beads while keeping the distance between the two substrates constant, and an opening for injecting a liquid crystal composition
  • the periphery was sealed with a sealant so as to leave After injecting the liquid crystal composition from the opening, the opening was sealed.
  • a liquid crystal display device thus produced was combined with a three-wavelength CCFL light source of a backlight unit to produce a color display device.
  • Example 68 to 71, Reference Examples 16 and 17 (Color filter (CF-2 to 7)) Thereafter, the color filters (CF-2 to 65) of Examples 68 to 71 and Reference Examples 16 and 17 were combined in the same manner as in the production of the color filter (CF-1) by combining the resist material shown in Table 8 with a three-wavelength CCFL light source. 7) and a color display device were produced.
  • the color filter formed using the quinophthalone dye of this embodiment has at least one filter segment (green or red) as compared with the filter segment using the conventional pigment.
  • the color filter (CF-2, 3) using the quinophthalone dye of this embodiment the brightness was improved. As a result, the brightness of the white display increased, and the improvement of the performance as a color filter was confirmed.
  • the color filter formed using the quinophthalone dye of this embodiment has at least one filter segment (yellow) as compared with a filter segment containing a conventionally used pigment.
  • the brightness of the color filter (CF-6) containing the quinophthalone dye of this embodiment also improved, and as a result, the brightness of white display increased, and the improvement of the performance as a color filter was confirmed.
  • Example 70 when all of the green, red, and yellow colors of Example 70 contain the color filter dye of this embodiment (CF-5), it was confirmed that the brightness was further improved, and as a result, the brightness of white display was increased. .
  • Embodiment VI The weight average molecular weight (Mw) of the resin is as follows.
  • the polymerization average molecular weight (Mw) of the resin was measured in terms of polystyrene measured using TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent. It is a weight average molecular weight (Mw).
  • an acrylic resin solution 2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • This slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine. Further, 100 parts of chloroaluminum phthalocyanine was slowly added to 1200 parts of concentrated sulfuric acid at room temperature in a reaction vessel. The mixture was stirred at 40 ° C. for 3 hours, and the sulfuric acid solution was poured into 24000 parts of cold water at 3 ° C. The blue precipitate was filtered, washed with water, and dried to obtain 102 parts of hydroxyaluminum phthalocyanine 1 represented by the following formula (3).
  • hydroxyaluminum phthalocyanine 2 represented by the following formula (4) was obtained by the same production method except that 250 parts of 4-methylphthalodinitrile was used instead of phthalodinitrile. .
  • hydroxyaluminum phthalocyanine 3 represented by the following formula (5) was obtained by the same production method except that the amount was changed to 285 parts of 4-chlorophthalodinitrile instead of phthalodinitrile. .
  • TOF-MS mass spectrometer
  • the green coloring composition (DG-1-34) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater, then dried at 70 ° C. for 20 minutes, and then at 220 ° C. for 30 minutes.
  • a coated substrate was prepared by heating and cooling for a minute.
  • the brightness Y (C) of the obtained coating film was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.).
  • brightness Y (C) it can be said that there is a clear difference if it is 0.2 points or more.
  • the green coloring composition (DG-1-34) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater, then dried at 70 ° C. for 20 minutes, and then at 220 ° C. for 30 minutes.
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 230 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ⁇ Eab * was determined and evaluated in the following three stages.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 ) ⁇ : ⁇ Eab * is less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more and less than 10.0 ⁇ : ⁇ Eab * is 10.0 or more
  • a coated substrate is prepared in the same manner as in the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) with a C light source is measured with a microspectrophotometer ( Measurement was performed using “OSP-SP100” manufactured by Olympus Optical Co., Ltd.
  • an ultraviolet cut filter (“COLORED OPTICAL GLASS L38” manufactured by Hoya Co., Ltd.) is attached on the substrate, and irradiated with ultraviolet rays using a 470 W / m 2 xenon lamp for 100 hours, and then the chromaticity ([ L * (2), a * (2), b * (2)]) were measured, and the color difference ⁇ Eab * was determined by the above formula and evaluated according to the same criteria as for heat resistance.
  • the colorant which is a feature of the embodiment includes a phthalocyanine dye represented by the general formula (8A) and a quinophthalone dye represented by the general formula (6). It was excellent in lightness, and the heat resistance and light resistance of the coating film were satisfactory.
  • the green coloring compositions (DG-25 to 30, 33, and 34) of Reference Examples 1 to 6, 9, and 10 had low brightness and had problems with heat resistance and light resistance.
  • the green coloring compositions (DG-31 and 32) of Reference Examples 7 and 8 had no problem in heat resistance and light resistance, but the brightness was lower than that in Examples.
  • Green photosensitive coloring composition (RG-1) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 1.0 ⁇ m filter to obtain a green photosensitive coloring composition (RG-1).
  • Green coloring composition (DG-1) 55.0 parts Acrylic resin solution 2 9.8 parts Photopolymerizable monomer ("Aronix M402" manufactured by Toagosei Co., Ltd.) 4.6 parts Photopolymerization initiator (Ciba Japan Co., Ltd.) "Irgacure OXE02”) 0.8 parts Propylene glycol monomethyl ether acetate 19.8 parts Cyclohexanone 10.0 parts
  • Green photosensitive coloring composition (RG-2-34) Green photosensitive coloring compositions (RG-2 to RG34) were obtained in the same manner as in Example 25 except that the green coloring composition (DG-1) was changed to the green coloring composition shown in Table 2.
  • the green photosensitive coloring composition (RG-1 to 34) was applied onto a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, and then dried at 70 ° C. for 20 minutes to obtain ultrahigh pressure mercury. Using a lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Then, after heating at 220 ° C. for 30 minutes and allowing to cool, the brightness Y (C) of the obtained coated substrate was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.).
  • OSP-SP100 microspectrophotometer
  • a C light source a C light source
  • sodium carbonate 1.5% by weight, sodium hydrogen carbonate 0.5% by weight, an anionic surface active agent (“Perex NBL” manufactured by Kao Corporation) 8.0% by weight and water 90% by weight was used.
  • brightness Y (C) it can be said that there is a clear difference if it is 0.2 points or more.
  • the green photosensitive coloring composition (RG-1 to 34) was applied onto a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, and then dried at 70 ° C. for 20 minutes to obtain ultrahigh pressure mercury. Using a lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. Subsequently, it heated at 220 degreeC for 30 minute (s), and after standing to cool, the coating-film board
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 230 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ⁇ Eab * was determined and evaluated in the following three stages.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 ) ⁇ : ⁇ Eab * is less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more and less than 10.0 ⁇ : ⁇ Eab * is 10.0 or more
  • a coated substrate is prepared in the same manner as in the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) with a C light source is measured with a microspectrophotometer ( Measurement was performed using “OSP-SP100” manufactured by Olympus Optical Co., Ltd.
  • an ultraviolet cut filter (“COLORED OPTICAL GLASS L38” manufactured by Hoya Co., Ltd.) is attached on the substrate, and irradiated with ultraviolet rays using a 470 W / m 2 xenon lamp for 100 hours, and then the chromaticity ([ L * (2), a * (2), b * (2)]) were measured, and the color difference ⁇ Eab * was determined by the above formula and evaluated according to the same criteria as for heat resistance.
  • the green photosensitive coloring composition (RG-1 to 34) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater so that the dry film thickness was 2.0 ⁇ m.
  • the film was exposed to ultraviolet light with an integrated light quantity of 50 mJ / cm 2 and developed with an alkaline developer at 23 ° C. to obtain a coated substrate.
  • 0.05 parts of the coating film was scraped off from the obtained coated substrate, and then immersed in 1.5 parts of liquid crystal (MLC-2041 manufactured by Merck Co., Ltd.) After aging at 120 ° C. for 1 hour and centrifugation at 4000 rpm for 15 minutes, the supernatant liquid was collected to prepare a coating film extraction liquid crystal sample liquid.
  • two glass substrates having an ITO transparent electrode with an effective electrode size of 10 mm ⁇ 10 mm are arranged facing each other so that the ITO transparent electrode surfaces face each other, and a small cell is produced using a sealing agent so that the cell gap is 9 ⁇ m. did.
  • a resist extraction liquid crystal sample solution is injected into the small cell between the cell gaps, a voltage of 5 V is applied at 60 ° C. for 60 ⁇ sec, and the cell voltage [V1] after the passage of 16.67 msec after the voltage is released Measured with a VHR-1S manufactured by Technica. The measurement was repeated 5 times, and the measured cell voltages were averaged.
  • Voltage holding ratio (%) ([V1] / 5) ⁇ 100 ⁇ : 95% or more ⁇ : 90% or more and less than 95% ⁇ : less than 90%
  • the colorant which is a feature of the present embodiment includes a green photosensitive coloring containing a phthalocyanine dye represented by the general formula (8A) and a quinophthalone dye represented by the general formula (6).
  • the composition had excellent brightness and showed good results in heat resistance, light resistance, and voltage holding ratio.
  • the green photosensitive coloring compositions (RG-25 to 30, 33, and 34) of Reference Examples 11 to 16, 19, and 20 had low lightness and poor heat resistance and light resistance. Further, in Reference Examples 15 to 18 using CI Pigment Green 58, the voltage holding ratio was lower than that in Examples.
  • red photosensitive coloring composition (RR-1)) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a red colored composition (DR-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Red pigment (CI Pigment Red 254) 9.6 parts Red Pigment (CI Pigment Red 177) 2.4 parts
  • Resin-type dispersant (“EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • red photosensitive coloring composition (RR-1).
  • Red coloring composition (DR-1) 42.0 parts Acrylic resin solution 2 13.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts
  • Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured) 2.0 parts
  • Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a blue photosensitive coloring composition (RB-1).
  • Blue coloring composition (DB-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907", manufactured by 2.0) Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 part 45.1 parts ethylene glycol monomethyl ether acetate
  • a black matrix was patterned on a glass substrate, and a red photosensitive coloring composition (RR-1) was applied onto the substrate with a spin coater to form a colored coating.
  • the film was irradiated with ultraviolet rays of 150 mJ / cm 2 through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 220 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • a blue photosensitive coloring composition RB-1
  • PGMAC propylene glycol monomethyl ether acetate.
  • Mw weight average molecular weight
  • the weight average molecular weight (Mw) of resin was measured using HLC-8220GPC (manufactured by Tosoh Corporation) as an apparatus, TSK-GEL SUPER HZM-N connected in series as a column, and THF as a solvent.
  • the molecular weight in terms of polystyrene.
  • ⁇ Contrast ratio> The light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate. At this time, if the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the colored composition, scattering or the like occurs by the colorant particles, and when a part of the polarization plane is displaced, the polarizing plate is transmitted in parallel.
  • a method for producing quinophthalone dye [A1] and quinophthalone dye [A2], binder resin solution, resin-type dispersant solution, quinophthalone pigment [B], and aluminum phthalocyanine pigment used in Examples and Reference Examples, and fine pigments The method for producing, the method for producing the green coloring composition and the red coloring composition, and the method for producing the green photosensitive coloring composition and the red photosensitive coloring composition will be described.
  • quinophthalone dye (A1-3-14) The corresponding 2-methylquinolines and naphthalenecarboxylic anhydride were reacted in the same manner as for quinophthalone dye (A1-1) to obtain quinophthalone dyes (A1-3 to 14).
  • the product was identified as a target product by identifying the compound with a mass spectrometer (TOF-MS: autoflex II manufactured by Bruker Daltonics).
  • a reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device was charged with 196 parts of cyclohexanone, heated to 80 ° C., and purged with nitrogen in the reaction vessel.
  • Resin Dispersant Solution 1 A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 80 parts of n-butyl methacrylate and 120 parts of benzyl methacrylate and replaced with nitrogen gas. The inside of the reaction vessel was heated to 80 ° C., and a solution in which 0.1 part of 2,2′-azobisisobutyronitrile was dissolved in 12 parts of 3-mercapto-1,2-propanediol was added. Reacted for hours. It was confirmed that 95% had reacted by solid content measurement.
  • Resin Dispersant Solution 2 A resin-type dispersant (“BYK-LPN6919” manufactured by Big Chemie) was diluted with PGMAC to prepare a resin-type dispersant solution 2 (dispersant 2) having a nonvolatile content of 20% by weight.
  • compound (2) was obtained by the same method as the synthesis of compound (1) according to the synthesis method described in JP-A-2008-81666 using quinophthalone pigment (B-1) as a raw material.
  • This slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine. Further, 100 parts of chloroaluminum phthalocyanine was slowly added to 1200 parts of concentrated sulfuric acid at room temperature in a reaction vessel. The mixture was stirred at 40 ° C. for 3 hours, and the sulfuric acid solution was poured into 24000 parts of cold water at 3 ° C. The blue precipitate was filtered, washed with water and dried to obtain 102 parts of an aluminum phthalocyanine pigment (C-1) represented by the following formula (53).
  • C-1 aluminum phthalocyanine pigment represented by the following formula (53).
  • Aligninum phthalocyanine pigment (C-2) In a reaction vessel, add 100 parts of aluminum phthalocyanine pigment (C-1) represented by formula (53) and 49.5 parts of diphenyl phosphate to 1000 parts of methanol, heat to 40 ° C., and react for 8 hours. I let you. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain 114 parts of an aluminum phthalocyanine pigment (C-2) represented by the following formula (54).
  • Aligninum phthalocyanine pigment (C-3) In a reaction vessel, add 1000 parts of methanol, 100 parts of aluminum phthalocyanine pigment (C-1) represented by formula (53) and 43.2 parts of diphenylphosphinic acid, and heat to 40 ° C. for 8 hours. Reacted. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain 112 parts of an aluminum phthalocyanine pigment (C-3) represented by the following formula (55).
  • ⁇ Pigment refinement method> (Yellow colorant (PY-1)) 100 parts of quinophthalone pigment (B-1), 1200 parts of sodium chloride and 120 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), kneaded at 60 ° C. for 6 hours, and subjected to salt milling. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of a yellow colorant (PY-1) were obtained. The average primary particle size was 31.3 nm.

Landscapes

  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal (AREA)

Abstract

L'invention concerne une composition colorée pour filtres de couleurs qui comprend un colorant représenté par la formule générale, une résine de liant, et un solvant. Dans ladite formule, R1 à R13 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, un alkyle, un alcoxy, un aryle, un groupe acide ou un sel de ceux-ci avec soit un métal, soit un alkylammonium, phtalimidométhyl, soit sulfamoyle, et une paire de groupes contigus de R1 à R4, ou R10 à R13 est combinée pour former un noyau aromatique qui peut être substitué.
PCT/JP2012/056945 2011-03-18 2012-03-16 Composition colorée pour filtres de couleurs, et filtres de couleurs Ceased WO2012128233A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020137027447A KR101550427B1 (ko) 2011-03-18 2012-03-16 칼라 필터용 착색 조성물 및 칼라 필터
CN201280013839.8A CN103460086B (zh) 2011-03-18 2012-03-16 滤色器用着色组合物及滤色器

Applications Claiming Priority (20)

Application Number Priority Date Filing Date Title
JP2011060734 2011-03-18
JP2011-060734 2011-03-18
JP2011093515A JP4993026B1 (ja) 2011-04-19 2011-04-19 カラーフィルタ用着色剤、着色組成物、およびカラーフィルタ
JP2011-093515 2011-04-19
JP2011-093705 2011-04-20
JP2011093705 2011-04-20
JP2011-118726 2011-05-27
JP2011118726A JP5782834B2 (ja) 2011-05-27 2011-05-27 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2011-143658 2011-06-29
JP2011143658 2011-06-29
JP2011150514 2011-07-07
JP2011-150514 2011-07-07
JP2011-156970 2011-07-15
JP2011156970A JP5982657B2 (ja) 2011-07-15 2011-07-15 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2011-174656 2011-08-10
JP2011174656 2011-08-10
JP2011181111 2011-08-23
JP2011-181111 2011-08-23
JP2011286172 2011-12-27
JP2011-286172 2011-12-27

Publications (1)

Publication Number Publication Date
WO2012128233A1 true WO2012128233A1 (fr) 2012-09-27

Family

ID=46879380

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/056945 Ceased WO2012128233A1 (fr) 2011-03-18 2012-03-16 Composition colorée pour filtres de couleurs, et filtres de couleurs

Country Status (4)

Country Link
KR (1) KR101550427B1 (fr)
CN (1) CN103460086B (fr)
TW (1) TWI466954B (fr)
WO (1) WO2012128233A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013032486A (ja) * 2011-03-18 2013-02-14 Toyo Ink Sc Holdings Co Ltd キノフタロン色素、およびその用途
JP2014085562A (ja) * 2012-10-25 2014-05-12 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用着色組成物
JP2018017856A (ja) * 2016-07-27 2018-02-01 東洋インキＳｃホールディングス株式会社 固体撮像素子用緑色着色組成物および固体撮像素子用カラーフィルタ
JP2019113676A (ja) * 2017-12-22 2019-07-11 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
EP3206816B1 (fr) 2014-11-21 2020-04-01 Siemens Aktiengesellschaft Procédé de fabrication d'un élément et élément
CN113747149A (zh) * 2021-08-26 2021-12-03 浙江大华技术股份有限公司 滤光片的异常检测方法、装置、电子装置和存储介质

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI745284B (zh) * 2015-01-22 2021-11-11 南韓商艾瑞多斯公司 化合物、彼之製法、及含彼之著色劑
KR102029354B1 (ko) * 2015-02-03 2019-10-07 토요잉크Sc홀딩스주식회사 프탈로시아닌 안료, 착색 조성물 및 칼라필터
KR102222403B1 (ko) * 2015-03-19 2021-03-03 동우 화인켐 주식회사 녹색 화소용 착색 감광성 수지 조성물
KR102280402B1 (ko) * 2015-03-19 2021-07-22 동우 화인켐 주식회사 녹색 화소용 착색 감광성 수지 조성물
KR102222404B1 (ko) * 2015-03-19 2021-03-03 동우 화인켐 주식회사 적색 또는 녹색 화소용 착색 감광성 수지 조성물
KR102222401B1 (ko) * 2015-03-20 2021-03-03 동우 화인켐 주식회사 적색, 녹색 화소용 착색 감광성 수지 조성물
KR102241499B1 (ko) * 2015-03-25 2021-04-16 동우 화인켐 주식회사 적색, 녹색 화소용 착색 감광성 수지 조성물
KR102241497B1 (ko) * 2015-03-25 2021-04-16 동우 화인켐 주식회사 적색 화소용 착색 감광성 수지 조성물
KR102241498B1 (ko) * 2015-03-25 2021-04-16 동우 화인켐 주식회사 적색, 녹색 화소용 착색 감광성 수지 조성물
KR102241496B1 (ko) * 2015-03-26 2021-04-16 동우 화인켐 주식회사 적색 화소용 착색 감광성 수지 조성물
TWI761230B (zh) 2015-12-08 2022-04-11 日商富士軟片股份有限公司 感放射線性樹脂組成物、硬化膜、圖案形成方法、固體攝影元件及影像顯示裝置
JP2017197685A (ja) * 2016-04-28 2017-11-02 東洋インキＳｃホールディングス株式会社 フタロシアニン顔料、着色組成物およびカラーフィルタ
KR102067858B1 (ko) * 2016-05-24 2020-01-17 주식회사 엘지화학 화합물 및 이를 포함하는 색재 조성물 및 이를 포함하는 수지 조성물
KR102679526B1 (ko) * 2016-09-01 2024-06-28 엘지디스플레이 주식회사 컬러필터용 적색 착색 조성물, 컬러필터 및 이를 포함하는 액정표시장치
KR102713657B1 (ko) * 2016-09-30 2024-10-04 엘지디스플레이 주식회사 착색제, 이를 포함하는 착색 수지 조성물 및 컬러필터
JP6501050B2 (ja) * 2017-03-01 2019-04-17 Dic株式会社 キノフタロン化合物
JP6680402B2 (ja) * 2017-05-26 2020-04-15 Dic株式会社 液晶表示装置
TWI694932B (zh) * 2017-11-01 2020-06-01 中北塗料企業股份有限公司 提供塗料ｄｉｙ調色的方法及設備
KR102613881B1 (ko) * 2017-12-22 2023-12-15 토요잉크Sc홀딩스주식회사 컬러 필터용 착색조성물 및 컬러 필터
KR102607184B1 (ko) 2018-08-31 2023-11-29 주식회사 이엔에프테크놀로지 착색 감광성 수지 조성물
TWI851660B (zh) * 2019-02-18 2024-08-11 日商住友化學股份有限公司 著色組成物、化合物、彩色濾光片及顯示裝置
JPWO2021149596A1 (fr) * 2020-01-21 2021-07-29
JP7441134B2 (ja) * 2020-07-16 2024-02-29 住友化学株式会社 着色硬化性樹脂組成物、カラーフィルタ及び表示装置

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51147544A (en) * 1975-06-13 1976-12-17 Teijin Ltd Coloring method for polymeric materials
JPS52150438A (en) * 1976-06-08 1977-12-14 Teijin Ltd Quinoline derivative
JPS53121822A (en) * 1977-04-01 1978-10-24 Teijin Ltd Colored organic compounds and their manufacture
JPS5461936A (en) * 1977-10-26 1979-05-18 Ricoh Co Ltd Photoreceptor for electrophotography
JPH0680744A (ja) * 1992-03-31 1994-03-22 Mitsui Toatsu Chem Inc カラーフィルター用光硬化型樹脂組成物、及び該組成物を用いるカラーフィルターの製造法
JP2003221520A (ja) * 2001-11-27 2003-08-08 Bayer Ag 架橋ペリノン／キノフタロン
JP2006208986A (ja) * 2005-01-31 2006-08-10 Ricoh Co Ltd 電子写真捺染用イエロー現像剤及びその捺染方法
JP2008074985A (ja) * 2006-09-22 2008-04-03 Toyo Ink Mfg Co Ltd 顔料、顔料組成物及び顔料分散体
JP2010039433A (ja) * 2008-08-08 2010-02-18 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物及びカラーフィルタ
JP2010079247A (ja) * 2008-08-29 2010-04-08 Toyo Ink Mfg Co Ltd カラーフィルタ用着色剤、それを用いたカラーフィルタ用着色組成物、及びカラーフィルタ

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1520944A (en) * 1975-06-12 1978-08-09 Teijin Ltd Quinoline derivatives for use als colouring agents
DE69317316T2 (de) * 1992-03-31 1998-10-08 Mitsui Chemicals Inc Verfahren zur Herstellung eines Farbfilters und fotohärtbare Harzzusammensetzung für dieses Verfahren
TW416011B (en) * 1998-08-28 2000-12-21 Toray Industries Colored polymer film, color filter and liquid crystal display device
JP2001335711A (ja) 2000-05-29 2001-12-04 Fuji Photo Film Co Ltd キノフタロン系化合物、それを含む顔料分散剤、顔料分散組成物及び着色感光性組成物
JP2008074945A (ja) 2006-09-21 2008-04-03 Aica Kogyo Co Ltd 防眩ハードコート剤及び防眩フィルム
US8277697B2 (en) * 2008-10-29 2012-10-02 Global Oled Technology Llc Color filter element with improved colorant dispersion

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51147544A (en) * 1975-06-13 1976-12-17 Teijin Ltd Coloring method for polymeric materials
JPS52150438A (en) * 1976-06-08 1977-12-14 Teijin Ltd Quinoline derivative
JPS53121822A (en) * 1977-04-01 1978-10-24 Teijin Ltd Colored organic compounds and their manufacture
JPS5461936A (en) * 1977-10-26 1979-05-18 Ricoh Co Ltd Photoreceptor for electrophotography
JPH0680744A (ja) * 1992-03-31 1994-03-22 Mitsui Toatsu Chem Inc カラーフィルター用光硬化型樹脂組成物、及び該組成物を用いるカラーフィルターの製造法
JP2003221520A (ja) * 2001-11-27 2003-08-08 Bayer Ag 架橋ペリノン／キノフタロン
JP2006208986A (ja) * 2005-01-31 2006-08-10 Ricoh Co Ltd 電子写真捺染用イエロー現像剤及びその捺染方法
JP2008074985A (ja) * 2006-09-22 2008-04-03 Toyo Ink Mfg Co Ltd 顔料、顔料組成物及び顔料分散体
JP2010039433A (ja) * 2008-08-08 2010-02-18 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物及びカラーフィルタ
JP2010079247A (ja) * 2008-08-29 2010-04-08 Toyo Ink Mfg Co Ltd カラーフィルタ用着色剤、それを用いたカラーフィルタ用着色組成物、及びカラーフィルタ

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013032486A (ja) * 2011-03-18 2013-02-14 Toyo Ink Sc Holdings Co Ltd キノフタロン色素、およびその用途
JP2014085562A (ja) * 2012-10-25 2014-05-12 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用着色組成物
EP3206816B1 (fr) 2014-11-21 2020-04-01 Siemens Aktiengesellschaft Procédé de fabrication d'un élément et élément
JP2018017856A (ja) * 2016-07-27 2018-02-01 東洋インキＳｃホールディングス株式会社 固体撮像素子用緑色着色組成物および固体撮像素子用カラーフィルタ
JP2019113676A (ja) * 2017-12-22 2019-07-11 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
CN113747149A (zh) * 2021-08-26 2021-12-03 浙江大华技术股份有限公司 滤光片的异常检测方法、装置、电子装置和存储介质
CN113747149B (zh) * 2021-08-26 2024-04-16 浙江大华技术股份有限公司 滤光片的异常检测方法、装置、电子装置和存储介质

Also Published As

Publication number Publication date
KR20130137028A (ko) 2013-12-13
KR101550427B1 (ko) 2015-09-04
TW201241099A (en) 2012-10-16
TWI466954B (zh) 2015-01-01
CN103460086B (zh) 2016-05-18
CN103460086A (zh) 2013-12-18

Similar Documents

Publication Publication Date Title
WO2012128233A1 (fr) Composition colorée pour filtres de couleurs, et filtres de couleurs
KR101904761B1 (ko) 컬러 필터용 적색 착색 조성물 및 컬러 필터
JP5789847B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6031826B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP5817028B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6217067B2 (ja) カラーフィルタ用着色組成物およびカラーフィルタ
JP5880157B2 (ja) キノフタロン色素、およびその用途
CN103370642A (zh) 彩色滤光片用着色组合物以及彩色滤光片
JP6264135B2 (ja) 着色剤とその製造方法およびそれを用いた着色組成物、カラーフィルタ
JP2012068559A (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP5783086B2 (ja) カラーフィルタ用緑色着色組成物、およびカラーフィルタ
JP2013041145A (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP5982657B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP2011039307A (ja) カラーフィルタ用着色組成物、及びカラーフィルタ
JP5880196B2 (ja) カラーフィルタ用赤色着色組成物及びカラーフィルタ
JP2019109487A (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP2017156652A (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP2012212055A (ja) カラーフィルタ用着色組成物およびカラーフィルタ
JP7694133B2 (ja) カラーフィルタ用着色組成物、カラーフィルタ、液晶表示装置、および固体撮像素子
JP2013125265A (ja) カラーフィルタ用赤色着色組成物及びカラーフィルタ
JP2015172652A (ja) トリアリールメタン色素、およびその用途
JP2015175927A (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP2012013866A (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP2020086424A (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP5888083B2 (ja) カラーフィルタ用緑色着色組成物、およびカラーフィルタ

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12760075

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20137027447

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 12760075

Country of ref document: EP

Kind code of ref document: A1