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WO2018135370A1 - Liquide de dispersion de matière colorée pour filtre coloré, composition de résine colorée pour filtre coloré, filtre coloré, et dispositif d'affichage - Google Patents

Liquide de dispersion de matière colorée pour filtre coloré, composition de résine colorée pour filtre coloré, filtre coloré, et dispositif d'affichage Download PDF

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Publication number
WO2018135370A1
WO2018135370A1 PCT/JP2018/000470 JP2018000470W WO2018135370A1 WO 2018135370 A1 WO2018135370 A1 WO 2018135370A1 JP 2018000470 W JP2018000470 W JP 2018000470W WO 2018135370 A1 WO2018135370 A1 WO 2018135370A1
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Prior art keywords
color material
mass
color
group
resin composition
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PCT/JP2018/000470
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English (en)
Japanese (ja)
Inventor
中村　和彦
健朗 長井
慶輝 呉
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DNP Fine Chemicals Co Ltd
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DNP Fine Chemicals Co Ltd
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Priority to CN201880005469.0A priority Critical patent/CN110114702B/zh
Priority to JP2018541447A priority patent/JP6494875B2/ja
Publication of WO2018135370A1 publication Critical patent/WO2018135370A1/fr
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • 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
    • C09B63/00—Lakes
    • 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
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • the present invention relates to a color filter color material dispersion, a color filter colored resin composition, a color filter, and a display device.
  • Color filters are used in these liquid crystal display devices and organic light emitting display devices.
  • the light passing through the color filter is colored as it is into the color of each pixel constituting the color filter, and the light of those colors is synthesized to form a color image.
  • an organic light emitting element emitting white light or an inorganic light emitting element emitting white light may be used.
  • a color filter is used for color adjustment. For this reason, there is a growing demand for color filters with higher brightness, higher contrast, and improved color reproducibility.
  • a region connecting three points of red, green, and blue pixels is a limit of colors that can be reproduced.
  • a color filter having a larger triangle formed by three points of red, green, and blue pixels has a wider range of colors that the display device can reproduce on the screen. Therefore, in order to achieve a color space having a wide color gamut, it is required to achieve high color density chromaticity in each color pixel.
  • Patent Document 1 as a color filter used in a liquid crystal display device of a white LED light source having a color gamut that satisfies the NTSC standard, the transmittance at 550 nm that transmits blue pixels in the color filter is 1% or less, and A color filter having a maximum transmittance wavelength of visible light transmitting through the color filter in the range of 470 nm to 500 nm is disclosed, and the blue coloring composition forming the blue pixel is C.I. I. Pigment Blue 15: 6 or C.I. I. Pigment® Blue 15: 3, C.I. I. Pigment Green7, C.I. I. Pigment Green 36 and C.I. I. Pigment® Green 58 contains at least one green pigment.
  • the solidified material on the die lip is partly peeled off and easily adheres to the colored layer of the color filter, causing a foreign matter defect.
  • the solvent re-solubility is likely to be insufficient, and the yield is reduced due to the occurrence of the foreign matter in the color filter manufacturing process.
  • the blue color material used for the blue pixel of the color filter is generally caused by the tendency that the solvent resolubility tends to be very poor.
  • the colored resin composition according to the technique of Patent Document 1 has a problem that the solvent re-solubility is poor.
  • the present invention provides a color material dispersion for a color filter that is excellent in color material dispersion stability, has improved solvent resolubility, and can form a colored resin composition that expands the blue reproduction range, and the color material dispersion for the color filter.
  • a color resin composition for a color filter that can form a colored layer with improved solvent resolubility and an expanded blue reproduction range, and color reproducibility using the color resin composition for color filter.
  • An object is to provide a color filter that is excellent in productivity and a display device that is excellent in color reproducibility and improved in productivity by using the color filter.
  • a color material dispersion for a color filter according to the present invention is a color material dispersion containing a color material, a dispersant, and a solvent,
  • the color material is a blue color material, a purple color material, and C.I. I. Including Pigment Green 59
  • the dispersing agent is a color material dispersion for a color filter, which is a polymer having a structural unit represented by the following general formula (I).
  • the colored resin composition for a color filter according to the present invention is a colored resin composition for a color filter containing a coloring material, a dispersant, a binder component, and a solvent,
  • the color material is a blue color material, a purple color material, and C.I. I. Including Pigment Green 59
  • the dispersant is a colored resin composition for a color filter, which is a polymer having a structural unit represented by the following general formula (I).
  • R 1 is a hydrogen atom or a methyl group
  • A is a divalent linking group
  • R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon that may contain a hetero atom. Represents a group, and R 2 and R 3 may combine with each other to form a ring structure.
  • the color filter according to the present invention is a color filter comprising at least a substrate and a colored layer provided on the substrate, wherein at least one of the colored layers is a colored resin composition for a color filter according to the present invention. It is the coloring layer which is a hardened
  • the present invention provides a display device comprising the color filter according to the present invention.
  • the color material dispersion liquid for color filters which can form the colored resin composition which is excellent in color material dispersion stability, improves solvent re-dissolution property, and expands a blue reproduction range
  • the said color for color filters Color reproducibility using a colored dispersion composition for a color filter that can form a colored layer with improved solvent resolubility and an expanded blue reproduction range, using the material dispersion, and the color resin composition for color filter
  • a display device that is excellent in color reproducibility and improved in productivity can be provided.
  • FIG. 1 is a schematic view showing an example of the color filter of the present invention.
  • FIG. 2 is a schematic view showing an example of the display device of the present invention.
  • FIG. 3 is a schematic view showing another example of the display device of the present invention.
  • light includes electromagnetic waves having wavelengths in the visible and invisible regions, and further includes radiation, and the radiation includes, for example, microwaves and electron beams. Specifically, it means an electromagnetic wave having a wavelength of 5 ⁇ m or less and an electron beam.
  • (meth) acryl represents each of acryl and methacryl
  • (meth) acrylate represents each of acrylate and methacrylate.
  • C.I. I. Pigment Blue “PB”, C.I. I. Pigment Violet “PV”, C.I. I. Pigment Green is abbreviated as “PG” where appropriate.
  • a color material dispersion for a color filter according to the present invention is a color material dispersion containing a color material, a dispersant, and a solvent,
  • the color material is a blue color material, a purple color material, and C.I. I. Including Pigment Green 59,
  • the dispersant is a polymer having a structural unit represented by the following general formula (I).
  • R 1 is a hydrogen atom or a methyl group
  • A is a divalent linking group
  • R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon that may contain a hetero atom. Represents a group, and R 2 and R 3 may combine with each other to form a ring structure.
  • the color material dispersion of the present invention is used in combination with the specific color material and a polymer having a structural unit represented by the general formula (I) as a dispersant, the color material dispersion stability is improved. It is possible to form a colored resin composition that is excellent, has improved solvent resolubility, and expands the blue reproduction range. Although the cause of the blue color material is not yet known, the solvent resolubility tends to be poor, and when the colorant concentration is increased, the solvent resolubility tends to be very poor. Further, even if the color material concentration is increased by using a blue color material, there is a limit to the expansion of the blue reproduction range, which is insufficient.
  • I. Pigment Green 59 (hereinafter sometimes abbreviated as PG59) has a single color and a bluish green color, has a relatively strong coloring power, and has a high luminance. If a violet color material is further combined with such a combination of PG59 and a blue color material, the P / V ratio ((the total color material in the composition can be reduced) even if the content of the blue color material in the color material is suppressed. It was found that even when the ratio of (mass) / (total mass of solids other than coloring materials in the composition) ratio) was suppressed, a blue pixel contained in the blue chromaticity region of the high color density could be produced. Therefore, it is suitably used as a blue color material dispersion.
  • the luminance tends to be higher than when a blue pixel is produced using PG58.
  • the polymer having the structural unit represented by the general formula (I) is combined as a dispersant with the combination of the specific color materials, the specific color material is represented by the general formula (I), respectively. It is presumed that the specific color material that is firmly adsorbed to the nitrogen site contained in the structural unit and is well dispersed and surrounded by the dispersant is likely to flow while adsorbed to the re-dissolvable solvent.
  • a colored resin composition for producing a blue pixel included in a blue chromaticity region having a high color density is prepared by suppressing the content of the blue color material in the color material and suppressing the P / V ratio. And also has the function of the specific dispersant.
  • the colored resin composition with improved solvent re-solubility can be formed.
  • the content of the binder component is relatively Since it can be increased, the plate-making property is improved, and development chipping is easily suppressed. On the other hand, development residue is easily suppressed, and adhesion to the substrate is improved.
  • the color material dispersion of the present invention contains at least a color material, a dispersant, and a solvent, and may further contain other components as long as the effects of the present invention are not impaired. .
  • each component of the color material dispersion of the present invention will be described in detail in order.
  • the color material is a blue color material, a purple color material, and C.I. I. Pigment Green 59 is included.
  • C. I. Pigment Green 59 (PG59) is a zinc phthalocyanine pigment.
  • the PG 59 is characterized in that it can display an xy chromaticity coordinate area surrounded by the following equations 1, 2 and 3 in the XYZ color system of JIS Z8701 measured by using a C light source alone.
  • Equation 2 0.133 ⁇ x ⁇ 0.310
  • y 1189.500 ⁇ x 6 + 1817.000 ⁇ x 5 ⁇ 3011.300 ⁇ x 4 + 1447.800 ⁇ x 3 ⁇ 307.420 ⁇ x 2 + 27.628 ⁇ x ⁇ 0.285
  • Equation 3 0.121 ⁇ x ⁇ 0.310
  • PG59 used in the present invention has a wavelength (Tmax) at which the transmittance of the spectral transmittance spectrum in the range of 400 nm to 700 nm is 505 nm to 535 nm when the transmittance at 450 nm is 5%. Furthermore, the transmittance at the wavelength (Tmax) is 70% or more. Further, PG59 used in the present invention has a transmittance of the spectral transmittance spectrum at 435 nm of 15% or less, and further a transmittance of the spectral transmittance spectrum at 575 nm of 5% or less.
  • a coating solution by blending PG59 with an appropriate dispersant, binder component and solvent, apply it on a transparent substrate and dry it. It may be cured accordingly.
  • a binder component a non-curable thermoplastic resin composition may be used as long as a transparent coating film capable of performing colorimetry can be formed, or a photo-curable (photosensitive) or thermosetting resin composition. May be used.
  • a coating film containing only PG59 as a color material can be formed and colorimetry can be performed.
  • solid components other than the coloring material used in the resin composition of Example 1 described later can be used as the binder component.
  • the film thickness is 2.0 ⁇ m
  • the transmittance of the spectral transmittance spectrum at 380 nm to 780 nm is 95% or more.
  • the spectral transmittance spectrum can be measured using a spectroscopic measurement device (for example, an Olympus microspectrophotometer OSP-SP200).
  • PG59 has a single color and bluish green, has a relatively strong coloring power, and has a high luminance. Furthermore, PG59 tends to have better dispersibility than PG7, which is a conventional green pigment, and tends to improve contrast, and tends to have good re-dissolvability.
  • the blue color material used in the colored resin composition for a color filter of the present invention is not particularly limited, and a known blue organic pigment, a blue dye, and a blue lake color material that is a salt-forming compound of a blue dye are used. Can do.
  • the blue organic pigment is excellent in various resistances such as heat resistance and light resistance compared to the dye and the lake color material, and the blue dye is soluble and therefore has a higher transmittance than the organic pigment.
  • the lake color material is derived from a dye, it has a higher transmittance than a normal pigment and can achieve the demand for higher brightness.
  • blue organic pigment examples include C.I. I. Pigment blue 15, C.I. I. Pigment blue 15: 3, C.I. I. Pigment blue 15: 4, C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 16, C.I. I. And CI Pigment Blue 60.
  • a copper phthalocyanine-based blue pigment is preferable from the viewpoint of relatively excellent luminance.
  • blue dye examples include methine dyes, anthraquinone dyes, azo dyes, triarylmethane dyes, and phthalocyanine dyes.
  • the counter ion differs depending on the kind of the dye, the counter ion of the acidic dye is a cation, and the counter ion of the basic dye is an anion.
  • the counter cation of the acid dye include an ammonium cation, a metal cation, and an inorganic polymer.
  • a rake agent that generates ammonium ions for example, primary amine compounds, secondary amine compounds, tertiary amine compounds, and the like are preferable. Among them, secondary amines are preferred because of their excellent heat resistance and light resistance. It is preferable to use an amine compound or a tertiary amine compound.
  • the counter cation of the acid dye can be used alone or in combination of two or more.
  • the counter anion of the basic dye may be an organic anion or an inorganic anion.
  • the organic anion include organic compounds having an anionic group as a substituent.
  • the lake color material is an acid dye and a basic dye present as an ion pair.
  • rake agents that generate these organic anions include alkali metal salts and alkaline earth metal salts of the above organic anions.
  • the inorganic anion for example, an anion of oxo acid (phosphate ion, sulfate ion, chromate ion, tungstate ion (WO 4 2 ⁇ ), molybdate ion (MoO 4 2 ⁇ ), etc.) Mention may be made of inorganic anions such as polyacid anions condensed with oxo acids and mixtures thereof.
  • the polyacid may be an isopolyacid anion (M m O n ) c- or a heteropoly acid anion (X l M m O n ) c- .
  • M represents a poly atom
  • X represents a hetero atom
  • m represents a composition ratio of poly atoms
  • n represents a composition ratio of oxygen atoms.
  • the poly atom M include Mo, W, V, Ti, and Nb.
  • the hetero atom X include Si, P, As, S, Fe, and Co.
  • a polyacid anion containing at least one of molybdenum (Mo) and tungsten (W) is preferable, and a c-valent polyacid anion containing at least tungsten is more preferable.
  • rake agents that generate inorganic anions include alkali salts and alkali metal salts of the above inorganic anions.
  • the counter anion of the basic dye in the lake color material can be used alone or in combination of two or more.
  • Examples of the dark blue rake color material include C.I. I. Pigment blue 1, C.I. I. Pigment blue 1: 2, C.I. I. Pigment blue 2, C.I. I. Pigment blue 3, C.I. I. Pigment blue 8, C.I. I. Pigment blue 9, C.I. I. Pigment blue 10, C.I. I. Pigment blue 12, C.I. I. Pigment blue 14, C.I. I. Pigment blue 17: 1, C.I. I. Pigment blue 18, C.I. I. Pigment blue 19, C.I. I. Pigment blue 24, C.I. I. Pigment blue 24: 1, C.I. I. Pigment blue 53, C.I. I. Pigment blue 56, C.I. I.
  • Pigment blue 56 1, C.I. I. Pigment blue 61, C.I. I. Pigment blue 61: 1, C.I. I. Pigment blue 62, C.I. I. Pigment blue 63, C.I. I. And CI Pigment Blue 78.
  • the blue dye and the blue lake color material are not particularly limited, but among them, a triarylmethane color material containing triarylmethane as a basic skeleton is preferable from the viewpoint of improving the brightness and contrast of the colored layer.
  • a triarylmethane blue color material include a triarylmethane dye having a triarylmethane skeleton represented by the following general formula (1) and a triarylmethane lake color material.
  • R i to R vi each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent, and R i and R ii , R iii and R iv , R v and R vi may combine to form a ring structure, and Ar i represents a divalent aromatic group which may have a substituent.
  • i to R vi and Ar i may be the same or different.
  • the alkyl group in R i to R vi is not particularly limited, and examples thereof include linear or branched alkyl groups having 1 to 20 carbon atoms. It is preferably a linear or branched alkyl group having 8 carbon atoms, more preferably a linear or branched alkyl group having 1 to 5 carbon atoms from the viewpoint of ease of production and raw material procurement. Groups and methyl groups are preferred.
  • the substituent that the alkyl group may have is not particularly limited, and examples thereof include an aryl group, a halogen atom, and a hydroxyl group, and examples of the substituted alkyl group include a benzyl group.
  • the aryl group in R i to R vi is not particularly limited, and examples thereof include an aryl group having 6 to 12 carbon atoms, and specific examples include a phenyl group and a naphthyl group. Examples of the substituent that the aryl group may have include an alkyl group and a halogen atom.
  • R i and R ii , R iii and R iv , R v and R vi are bonded to form a ring structure.
  • R i and R ii , R iii and R iv , R v and R vi are nitrogen A ring structure is formed through an atom.
  • the ring structure is not particularly limited, and examples thereof include a pyrrolidine ring, a piperidine ring, and a morpholine ring.
  • Divalent aromatic group in Ar i is not particularly limited, other aromatic hydrocarbon radical consisting of carbon ring may be a heterocyclic group.
  • aromatic hydrocarbon in the aromatic hydrocarbon group in addition to a benzene ring, condensed polycyclic aromatic hydrocarbons such as naphthalene ring, tetralin ring, indene ring, fluorene ring, anthracene ring, phenanthrene ring; biphenyl, terphenyl, Examples thereof include chain polycyclic hydrocarbons such as diphenylmethane, triphenylmethane, and stilbene.
  • the chain polycyclic hydrocarbon may have O, S, and N in the chain skeleton such as diphenyl ether.
  • the heterocyclic ring in the heterocyclic group includes 5-membered heterocycles such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole and pyrazole; 6-membered heterocycles such as pyran, pyrone, pyridine, pyrone, pyridazine, pyrimidine and pyrazine. And condensed polycyclic heterocycles such as benzofuran, thionaphthene, indole, carbazole, coumarin, benzo-pyrone, quinoline, isoquinoline, acridine, phthalazine, quinazoline, quinoxaline and the like.
  • 5-membered heterocycles such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole and pyrazole
  • 6-membered heterocycles such as pyran, pyrone, pyridine, pyrone,
  • aromatic groups may have a substituent.
  • substituent that the aromatic group may have include an alkyl group having 1 to 5 carbon atoms and a halogen atom.
  • Ar i is preferably an aromatic group having 6 to 20 carbon atoms, more preferably an aromatic group composed of a condensed polycyclic carbocycle having 10 to 14 carbon atoms, particularly a phenylene group or a naphthylene group. It is preferable.
  • a plurality of R i to R vi and Ar i in one molecule may be the same or different.
  • triarylmethane dye represented by the general formula (1) include, for example, basic blue 7, basic blue 26 and the like.
  • the triarylmethane-based lake color material one or a plurality of elements selected from molybdenum, tungsten, silicon, and phosphorus of the basic triarylmethane-based dye represented by the general formula (1)
  • the rake color material which consists of an anion containing oxygen as an essential element is used suitably from the point which achieves the high brightness
  • the anion is preferably a heteropolyacid or isopolyacid anion containing at least one of molybdenum and tungsten as an essential element.
  • one or more selected from the group consisting of phosphotungstic acid, silicotungstic acid, phosphotungstomolybdic acid, and cytungstomolybdic acid is preferably used.
  • rake color materials can be prepared with reference to, for example, International Publication No. 2012/039416 and International Publication No. 2012/039417.
  • triarylmethane-based lake color material those represented by the following general formula (2) are also preferably used from the viewpoint of achieving high brightness of the colored layer.
  • A is an a-valent organic group in which the carbon atom directly bonded to N does not have a ⁇ bond, and the organic group is saturated aliphatic carbonized at least at the terminal directly bonded to N.
  • B c- represents a c-valent anion
  • R XI to R XV each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group, R XII , R XIII , R XIV and good .
  • Ar 1 be R XV combine to form a ring structure represents a divalent aromatic group which may have a substituent.
  • R XI ⁇ R XV and Ar 1 each identical It may or may not be.
  • a and c represent an integer of 2 or more
  • b and d represent an integer of 1 or more.
  • e is 0 or 1, and when e is 0, there is no bond.
  • a plurality of e may be the same or different.
  • a in the general formula (2) is an a-valent organic group in which the carbon atom directly bonded to N (nitrogen atom) does not have a ⁇ bond, and the organic group is saturated at least at the terminal directly bonded to N.
  • an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at the terminal directly bonded to N is linear, branched or cyclic unless the terminal carbon atom directly bonded to N has a ⁇ bond.
  • the carbon atom other than the terminal may have an unsaturated bond, may have a substituent, and the carbon chain contains O, S, and N. Also good.
  • a carbonyl group, a carboxy group, an oxycarbonyl group, an amide group or the like may be contained, and a hydrogen atom may be further substituted with a halogen atom or the like.
  • the aromatic group having an aliphatic hydrocarbon group in A is a monocyclic or polycyclic aromatic group having an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at the terminal directly bonded to N. And may have a substituent, and may be a heterocyclic ring containing O, S, and N. Especially, it is preferable that A contains a cyclic
  • the cyclic aliphatic hydrocarbon groups a bridged alicyclic hydrocarbon group is preferable from the viewpoint of skeleton fastness.
  • the bridged alicyclic hydrocarbon group means a polycyclic aliphatic hydrocarbon group having a bridged structure in the aliphatic ring and having a polycyclic structure, for example, norbornane, bicyclo [2,2,2]. Examples include octane and adamantane.
  • norbornane is preferable.
  • the group containing a benzene ring and a naphthalene ring is mentioned, for example, Among these, the group containing a benzene ring is preferable.
  • A is a divalent organic group, a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms, or an aromatic group substituted with two alkylene groups having 1 to 20 carbon atoms such as a xylylene group Etc.
  • the valence a in A is the number of chromogenic cation sites constituting the cation, and a is an integer of 2 or more.
  • the cation valence a is preferably 3 or more.
  • the upper limit of a is not particularly limited, but a is preferably 4 or less, and more preferably 3 or less, from the viewpoint of ease of production.
  • Ar 1 and R XI to R XV in the general formula (2) include those described in International Publication No. 2012/144520 pamphlet.
  • the anion portion (B c ⁇ ) is not particularly limited, and may be an organic anion or an inorganic anion.
  • the organic anion represents an anion containing at least one carbon atom.
  • an inorganic anion represents the anion which does not contain a carbon atom.
  • B c- is an inorganic anion from the viewpoint of high luminance and excellent heat resistance.
  • Specific examples of the organic anion and the inorganic anion include those described in International Publication No. 2012/144520 pamphlet.
  • luminance is a sort of tungsten (W) and molybdenum
  • b represents the number of cations
  • d represents the number of anions in the molecular aggregate
  • b and d represent an integer of 1 or more.
  • a plurality of cations in the molecular aggregate may be one kind alone, or two or more kinds may be combined.
  • the anion present in the molecular aggregate may be a single anion or a combination of two or more, and an organic anion and an inorganic anion may be used in combination. .
  • E in the general formula (2) is an integer of 0 or 1.
  • a plurality of e may be the same or different.
  • those containing at least a triarylmethane skeleton are preferably used.
  • a rake color material represented by General formula (2) it can prepare with reference to international publication 2012/144520 pamphlet, for example.
  • blue color material examples include C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 15: 3, C.I. I. It is preferable from the point of hue that it is 1 or more types selected from the group which consists of pigment blue 15: 4 and a triarylmethane type
  • the blue color material examples include C.I. I. Pigment Blue 16 is preferable from the viewpoint of expanding the hue, particularly the color reproduction range.
  • the purple color material used in the present invention includes a red purple color material to which the name of a red dye is attached. In addition, it can perform like the above-mentioned PG59 to make a purple color material into a coating film, and to measure a color.
  • the purple color material used in the colored resin composition for a color filter of the present invention is not particularly limited, and known purple organic pigments, purple dyes, purple lake color materials, and the like can be used.
  • Examples of the purple organic pigment include C.I. I. Pigment violet 1, 14, 15, 19, 23, 29, 32, 33, 36, 37, 38 and the like.
  • Pigment Violet 23 is preferable from the viewpoint of relatively excellent coloring power.
  • Examples of the purple dye include C.I. I. Acid Violet 29, 31, 33, 34, 36, 36: 1, 39, 41, 42, 43, 47, 51, 63, 76, 103, 118, 126 and other anthraquinone acid dyes, C.I. I. Cyanine acid dyes such as Basic Red 12; triarylmethane acid dyes such as Acid Violet 15, 16, 17, 19, 21, 23, 24, 25, 38, 49, 72; I. Acid Red 289, C.I. I. Acid Violet 9, C.I. I. Rhodamine acid dyes such as Acid Violet 30; I. Triarylmethane basic dyes such as basic violet 1, 3, and 14; I. And xanthene-based basic dyes such as Basic Violet 11.
  • C.I. I. Acid Violet 29, 31, 33, 34, 36, 36: 1, 39, 41, 42, 43, 47, 51, 63, 76, 103, 118, 126 and other anthraquinone acid dyes C.I. I. Cyanine acid dyes such
  • Examples of the purple lake color material include those obtained by rakeizing the above purple dye with a lake agent.
  • the counter ion differs depending on the kind of the dye, the counter ion of the acidic dye is a cation, and the counter ion of the basic dye is an anion.
  • the counter cation of the acid dye and the counter anion of the basic dye may be the same as those mentioned as the blue dye.
  • the purple lake color material is preferably at least one selected from the group consisting of an anthraquinone color material, a cyanine color material, and a xanthene color material.
  • a xanthene color material containing xanthene as a basic skeleton and including a rhodamine color material is preferable from the viewpoint of improving the luminance and contrast of the colored layer.
  • the xanthene acid dye in the lake color material it is preferable to have a compound represented by the following general formula (3), that is, a rhodamine acid dye.
  • R a to R d each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R a and R b , R c and R d are bonded to each other.
  • R a and R b , R c and R d are bonded to each other.
  • .R e to form a ring structure an acidic group
  • X is, .m represents a halogen atom is an integer of 0-5.
  • formula (3) are those having at least one acidic group , N is an integer of 0 or more.
  • the alkyl group for R a to R d is not particularly limited. Examples thereof include a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent. Among them, a linear or branched alkyl group having 1 to 8 carbon atoms is preferable. More preferably, it is a linear or branched alkyl group having 1 to 5 carbon atoms.
  • the substituent that the alkyl group may have is not particularly limited, and examples thereof include an aryl group, a halogen atom, a hydroxyl group, and the like, and the substituted alkyl group includes a benzyl group, and further, a substituent. May have a halogen atom or an acidic group.
  • the aryl group in R a to R d is not particularly limited.
  • an aryl group which may have a substituent having 6 to 20 carbon atoms is exemplified, and among them, a group having a phenyl group, a naphthyl group or the like is preferable.
  • Heteroaryl groups in R a ⁇ R d is, include heteroaryl groups which may have a substituent group having 5 to 20 carbon atoms, as a hetero atom, a nitrogen atom, an oxygen atom, those containing a sulfur atom is preferable .
  • Examples of the substituent that the aryl group or heteroaryl group may have include an alkyl group having 1 to 5 carbon atoms, a halogen atom, an acidic group, a hydroxyl group, an alkoxy group, a carbamoyl group, and a carboxylic acid ester group. .
  • R a to R d may be the same or different.
  • the acidic group or a salt thereof include a carboxy group (—COOH), a carboxylate group (—COO ⁇ ), a carboxylate group (—COOM, where M represents a metal atom), a sulfonate group (—SOO). 3 -), a sulfo group (-SO 3 H), sulfonate (-SO 3 M, wherein M represents a metal atom), and among them, a sulfonato group (-SO 3 -.), a sulfo group It is preferable to have at least one of (—SO 3 H) or a sulfonate group (—SO 3 M).
  • the metal atom M include a sodium atom and a potassium atom.
  • Acid Red 289, Acid Violet 9, Acid Violet 30 and the like are preferable from the viewpoint of increasing luminance.
  • the method for producing the compound represented by the general formula (3) is not particularly limited, and can be obtained by referring to, for example, JP-A 2010-211198.
  • a metal lake color material is preferably used as the rake color material of the xanthene acid dye.
  • a metal lake color material containing a metal atom is used as a rake agent.
  • the heat resistance of the coloring material is increased.
  • a rake agent a rake agent containing a metal atom that becomes a divalent or higher valent metal cation is preferable.
  • a blue color material, a purple color material, and PG59 are used in combination as color materials, but other color materials as exemplified in the colored resin composition described below are combined. It may be used.
  • the other color material for example, a red color material, an orange color material, a green color material, and the like are preferably used. Among them, a red color material, a green color, and the like exemplified in the colored resin composition described later from the viewpoint of hue. A material is preferably used.
  • each content ratio of the blue color material, the purple color material, and PG59, and the content ratio when other color materials are used are the same content ratios as those of the colored resin composition described later. It is preferable to do.
  • two or more colorant dispersions can be appropriately mixed and used to produce a colored resin composition, so that the colorant dispersion is preferably used even if the content ratio is not the same as that of the later-described colored resin composition.
  • the average primary particle size of the color material used in the present invention is not particularly limited as long as it can produce a desired color when it is used as a color layer of a color filter, and varies depending on the type of color material used. Is preferably in the range of 10 nm to 100 nm, more preferably 15 nm to 60 nm. When the average primary particle diameter of the color material is in the above range, a display device including a color filter manufactured using the color material dispersion of the present invention can be made with high contrast and high quality. .
  • the average dispersed particle diameter of the color material in the color material dispersion varies depending on the type of the color material used, it is preferably in the range of 10 nm to 100 nm, and preferably in the range of 15 nm to 60 nm. More preferred.
  • the average dispersed particle size of the color material in the color material dispersion is the dispersed particle size of the color material particles dispersed in a dispersion medium containing at least a solvent, and is measured by a laser light scattering particle size distribution meter. It is.
  • the color material dispersion is appropriately diluted to a concentration that can be measured with a laser light scattering particle size distribution meter (for example, 1000 times). Etc.) and can be measured at 23 ° C. by a dynamic light scattering method using a laser light scattering particle size distribution meter (for example, Nanotrack particle size distribution measuring device UPA-EX150 manufactured by Nikkiso Co., Ltd.).
  • the average distribution particle size here is a volume average particle size.
  • the content of the color material is not particularly limited.
  • the content of the color material is 5 parts by mass or more and 80 parts by mass or less, more preferably 8 parts by mass or more and 70 parts by mass with respect to 100 parts by mass of the total solid content in the color material dispersion from the viewpoint of dispersibility and dispersion stability. It is preferable to mix
  • it is 30 parts by mass or more and 80 parts by mass or less, more preferably 40 parts by mass or more with respect to 100 parts by mass of the total solid content in the color material dispersion. It is preferable to mix at a ratio of 75 parts by mass or less.
  • a polymer having a structural unit represented by the general formula (I) is used as a dispersant.
  • the structural unit represented by the general formula (I) has basicity and functions as an adsorption site for a coloring material.
  • the color material dispersion of the present invention improves the adsorption performance to the color material, and improves the dispersibility and dispersion stability of the color material. To do.
  • A is a divalent linking group.
  • the divalent linking group in A include an alkylene group having 1 to 10 carbon atoms, an arylene group, a —CONH— group, a —COO— group, and an ether group having a carbon atom number of 1 to 10 (—R ′).
  • R ′ and R ′′ are each independently an alkylene group) and combinations thereof.
  • a in the general formula (I) is preferably a divalent linking group containing a —CONH— group or a —COO— group.
  • Examples of the hydrocarbon group in the hydrocarbon group that may include a hetero atom in R 2 and R 3 include an alkyl group, an aralkyl group, and an aryl group.
  • Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, a tert-butyl group, a 2-ethylhexyl group, a cyclopentyl group, a cyclohexyl group, and the like. It is preferably 1 or more and 18 or less, and more preferably a methyl group or an ethyl group.
  • Examples of the aralkyl group include a benzyl group, a phenethyl group, a naphthylmethyl group, and a biphenylmethyl group.
  • the number of carbon atoms in the aralkyl group is preferably 7 or more and 20 or less, and more preferably 7 or more and 14 or less.
  • Examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, and a xylyl group.
  • the number of carbon atoms of the aryl group is preferably 6 or more and 24 or less, and more preferably 6 or more and 12 or less.
  • the preferred number of carbon atoms does not include the number of carbon atoms of the substituent.
  • the hydrocarbon group containing a hetero atom has a structure in which a carbon atom in the hydrocarbon group is replaced with a hetero atom.
  • the hetero atom that the hydrocarbon group may contain include an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom.
  • the hydrogen atom in the hydrocarbon group may be substituted with a halogen atom such as an alkyl group having 1 to 5 carbon atoms, a fluorine atom, a chlorine atom, or a bromine atom.
  • R 2 and R 3 are bonded to each other to form a ring structure” means that R 2 and R 3 form a ring structure through a nitrogen atom.
  • the ring structure formed by R 2 and R 3 may contain a hetero atom.
  • the ring structure is not particularly limited, and examples thereof include a pyrrolidine ring, a piperidine ring, and a morpholine ring.
  • R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group, or R 2 and R 3 are bonded to form a pyrrolidine ring.
  • a piperidine ring and a morpholine ring are preferable, and among them, at least one of R 2 and R 3 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, or R 2 and R 3.
  • Examples of the structural unit represented by the general formula (I) include dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, diethylaminopropyl (meth) acrylate, and other alkyl group-substituted amino groups.
  • Examples include group-containing (meth) acrylates, alkyl group-substituted amino group-containing (meth) acrylamides such as dimethylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, and the like.
  • dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, and dimethylaminopropyl (meth) acrylamide can be preferably used in terms of improving dispersibility and dispersion stability.
  • the structural unit represented by the general formula (I) may be composed of one type or may include two or more types of structural units.
  • the polymer having the structural unit represented by the general formula (I) preferably further includes a portion having solvent affinity from the viewpoint of improving dispersibility.
  • a monomer having an ethylenically unsaturated bond that can be polymerized with a monomer that derives the structural unit represented by the general formula (I) is selected depending on the solvent so as to have solvent affinity. It is preferable to select and use as appropriate. As a standard, it is preferable to introduce a solvent-affinity site so that the solubility of the polymer at 23 ° C. is 50 (g / 100 g solvent) or more with respect to the solvent used in combination.
  • a block copolymer can be formed from the viewpoint that the dispersibility and dispersion stability of the coloring material and the heat resistance of the resin composition can be improved and a colored layer having high brightness and high contrast can be formed.
  • a graft copolymer is preferable and a block copolymer is particularly preferable.
  • particularly preferred block copolymers will be described in detail.
  • Block copolymer When the block containing the structural unit represented by the general formula (I) is an A block, the structural unit represented by the general formula (I) is basic and the A block has an adsorption site for a coloring material. Function as. On the other hand, the B block not containing the structural unit represented by the general formula (I) functions as a block having solvent affinity.
  • the arrangement of each block of the block copolymer is not particularly limited, and for example, an AB block copolymer, an ABA block copolymer, a BAB block copolymer, and the like can be used. Among these, an AB block copolymer or an ABA block copolymer is preferable in terms of excellent dispersibility.
  • Examples of the structural unit constituting the B block include a monomer having an unsaturated double bond copolymerizable with the monomer that derives the structural unit represented by the general formula (I).
  • the structural unit represented by (II) is preferred.
  • a ′ is a direct bond or a divalent linking group
  • R 4 is a hydrogen atom or a methyl group
  • R 5 is a hydrocarbon group, — [CH (R 6 ) —CH (R 7 ) —O] x —R 8 or — [(CH 2 ) y —O] z —R 8.
  • R 6 and R 7 is independently a hydrogen atom or a methyl group.
  • R 8 is a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO, or —CH 2 COOR 9
  • R 9 is a hydrogen atom or a carbon atom number of 1 or more and 5 or less. It is an alkyl group.
  • the hydrocarbon group may have a substituent.
  • x represents an integer of 1 to 30, y represents an integer of 1 to 5, and z represents an integer of 1 to 18.
  • the divalent linking group A ′ in the general formula (II) can be the same as A in the general formula (I).
  • a ′ is preferably a divalent linking group containing a direct bond, —CONH— group, or —COO— group from the viewpoint of solubility in an organic solvent.
  • solubility in propylene glycol monomethyl ether acetate (PGMEA) suitably used as a solvent, and a relatively inexpensive material
  • a ′ may be a —COO— group. preferable.
  • the hydrocarbon group for R 5 is preferably an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, or an aryl group.
  • the alkyl group having 1 to 18 carbon atoms may be linear, branched or cyclic.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group examples include 2-ethylhexyl group, 2-ethoxyethyl group, cyclopentyl group, cyclohexyl group, bornyl group, isobornyl group, dicyclopentanyl group, dicyclopentenyl group, adamantyl group, and lower alkyl group-substituted adamantyl group.
  • the alkenyl group having 2 to 18 carbon atoms may be linear, branched or cyclic.
  • Examples of such an alkenyl group include a vinyl group, an allyl group, and a propenyl group.
  • the position of the double bond of the alkenyl group is not limited, but from the viewpoint of the reactivity of the polymer obtained, it is preferable that there is a double bond at the terminal of the alkenyl group.
  • Examples of the aliphatic hydrocarbon substituent such as an alkyl group or an alkenyl group include a nitro group and a halogen atom.
  • aryl group examples include a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, and a xylyl group, and may further have a substituent.
  • the number of carbon atoms of the aryl group is preferably 6 or more and 24 or less, and more preferably 6 or more and 12 or less.
  • aralkyl group a benzyl group, a phenethyl group, a naphthylmethyl group, a biphenylmethyl group, etc. are mentioned, Furthermore, you may have a substituent.
  • the number of carbon atoms in the aralkyl group is preferably 7 or more and 20 or less, and more preferably 7 or more and 14 or less.
  • substituent on the aromatic ring such as an aryl group and an aralkyl group include straight chain and branched alkyl groups having 1 to 4 carbon atoms, alkenyl groups, nitro groups, and halogen atoms.
  • the preferred number of carbon atoms does not include the number of carbon atoms of the substituent.
  • x is an integer of 1 or more and 30 or less, preferably an integer of 1 or more and 26 or less, more preferably an integer of 1 or more and 18 or less, still more preferably 1 or more and 4 or less, particularly preferably 1 or more and 2 Y is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 4 or less, more preferably 2 or 3.
  • z is an integer of 1 or more and 18 or less, preferably an integer of 1 or more and 4 or less, more preferably an integer of 1 or more and 2 or less.
  • the hydrocarbon group for R 8 can be the same as that shown for R 5 .
  • the hydrocarbon group for R 8 is preferably an alkyl group having 1 to 18 carbon atoms from the viewpoint of excellent developability.
  • R 9 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and may be linear, branched or cyclic.
  • R 5 in the structural unit represented by the general formula (II) may be the same or different from each other.
  • the R 5 is preferably selected so as to be excellent in compatibility with a solvent described later.
  • the solvent is generally used as a solvent for a colored resin composition for a color filter.
  • a commonly used solvent such as glycol ether acetate, ether or ester is used, a methyl group, an ethyl group, an isobutyl group, an n-butyl group, a 2-ethylhexyl group, a benzyl group or the like is preferable.
  • R 5 In the structural unit constituting the B block, as R 5 , — [CH (R 6 ) —CH (R 7 ) —O] x —R 8 or — [(CH 2 ) y —O] z — It contains what is R 8 is, excellent developability, from the viewpoint of excellent suppression of development residue.
  • R 5 may be substituted with a substituent such as an alkoxy group, a hydroxyl group, an epoxy group, or an isocyanate group as long as the dispersion performance of the block copolymer is not hindered.
  • the substituent may be added by reacting with the compound having the substituent.
  • the glass transition temperature (Tg) of the solvent-compatible block part of the block copolymer may be appropriately selected.
  • the glass transition temperature (Tg) of the solvent-compatible block part is preferably 80 ° C. or higher, and more preferably 100 ° C. or higher.
  • the glass transition temperature (Tg) of the solvent-affinity block part in the present invention can be calculated by the following formula.
  • Tgi is the glass transition temperature (absolute temperature) of the homopolymer of the i-th monomer.
  • the homopolymer glass transition temperature value (Tgi) of each monomer may adopt the value of Polymer Handbook (3rd Edition) (by J. Brandrup, EH Immergut (Wiley-Interscience, 1989)). it can.
  • the number of structural units constituting the solvent affinity block may be appropriately adjusted within a range where the colorant dispersibility is improved.
  • the number of structural units constituting the solvent-affinity block part is 10 or more and 200 or less from the viewpoint that the solvent-affinity part and the colorant affinity part act effectively and improve the dispersibility of the colorant.
  • it is 10 or more and 100 or less, more preferably 10 or more and 70 or less.
  • the solvent-affinity block part may be selected so as to function as a solvent-affinity site, and the repeating unit constituting the solvent-affinity block part may be composed of one kind, or two or more kinds.
  • the repeating unit may be included.
  • the dispersant is a polymer having a structure represented by the general formula (II) and having an amine value of 40 mgKOH / g to 120 mgKOH / g. It is preferable from the viewpoint of improving luminance and contrast without depositing foreign matters.
  • the amine value is within the above range, the viscosity is excellent in stability over time and heat resistance, and is also excellent in alkali developability and solvent resolubility.
  • the amine value of the dispersant is preferably 60 mgKOH / g or more, more preferably 90 mgKOH / g or more, from the viewpoint of dispersibility and dispersion stability.
  • the amine value of the dispersant is preferably 115 mgKOH / g or less, and more preferably 105 mgKOH / g or less.
  • the amine value refers to the number of mg of potassium hydroxide equivalent to perchloric acid required to neutralize the amine component contained in 1 g of a sample, and can be measured by the method defined in JIS-K7237. When measured by this method, even if it is an amino group that forms a salt with the organic acid compound in the dispersant, the organic acid compound usually dissociates, so that the block copolymer itself used as the dispersant is itself The amine value of can be measured.
  • the acid value of the dispersant used in the present invention is preferably 1 mgKOH / g or more as a lower limit from the viewpoint of the effect of suppressing development residue.
  • the acid value of the dispersant is more preferably 2 mgKOH / g or more from the viewpoint of more excellent development residue suppression effect.
  • the acid value of the dispersant may be less than 1 mgKOH / g, preferably 0 mgKOH / g, from the viewpoint of dispersibility and dispersion stability.
  • the acid value of the dispersant used in the present invention is 18 mgKOH / g or less as the upper limit of the acid value of the dispersant from the viewpoint of preventing deterioration in development adhesion and solvent resolubility. preferable.
  • the acid value of the dispersant is more preferably 12 mgKOH / g or less, and even more preferably 8 mgKOH / g or less, from the viewpoint that the development adhesion and the solvent re-solubility are improved.
  • the acid value of the block copolymer before salt formation is preferably 1 mgKOH / g or more, and more preferably 2 mgKOH / g or more.
  • the acid value of the block copolymer before salt formation may be less than 1 mgKOH / g, preferably 0 mgKOH / g, from the viewpoint of dispersibility and dispersion stability.
  • the upper limit of the acid value of the block copolymer before salt formation is preferably 18 mgKOH / g or less, more preferably 12 mgKOH / g or less, and even more preferably 8 mgKOH / g or less. . This is because the development adhesiveness and the solvent resolubility are improved.
  • the glass transition temperature of a dispersing agent is 30 degreeC or more from the point which image development adhesiveness improves. That is, whether the dispersant is a block copolymer before salt formation or a salt block copolymer, the glass transition temperature is preferably 30 ° C. or higher.
  • the glass transition temperature of the dispersant is low, it is particularly close to the developer temperature (usually about 23 ° C.), and the development adhesion may be lowered. This is presumably because when the glass transition temperature is close to the developer temperature, the movement of the dispersant increases during development, resulting in poor development adhesion.
  • the glass transition temperature is 30 ° C.
  • the glass transition temperature of the dispersant is preferably 32 ° C. or higher, more preferably 35 ° C. or higher, from the viewpoint of development adhesion. On the other hand, the temperature is preferably 200 ° C. or lower from the viewpoint of operability during use, such as easy precision weighing.
  • the glass transition temperature of the dispersant in the present invention can be determined by measuring by differential scanning calorimetry (DSC) according to JIS K7121.
  • the amount of the binder is relatively decreased, so that the colored resin layer is easily peeled off from the base substrate during development.
  • the dispersant contains a B block containing a structural unit derived from a carboxy group-containing monomer and has the specific acid value and glass transition temperature, the development adhesion is improved. If the acid value is too high, the developability is excellent, but it is presumed that the polarity is too high and peeling easily occurs during development.
  • the dispersant is a polymer having a structure represented by the general formula (I) and having an amine value of 40 mgKOH / g or more and 120 mgKOH / g or less, and an acid value.
  • 1 mgKOH / g or more and 18 mgKOH / g or less and a glass transition temperature of 30 ° C. or more is excellent in colorant dispersion stability, improves contrast, and suppresses generation of development residue when a colored resin composition is obtained.
  • the carboxy group-containing monomer a monomer that can be copolymerized with a monomer having a structural unit represented by the general formula (I) and contains an unsaturated double bond and a carboxy group can be used.
  • monomers include (meth) acrylic acid, vinyl benzoic acid, maleic acid, maleic acid monoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, acrylic acid dimer, and the like.
  • an addition reaction product of a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate and a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride, ⁇ -carboxy-polycaprolactone Mono (meth) acrylates can also be used.
  • a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride, ⁇ -carboxy-polycaprolactone Mono (meth) acrylates
  • acid anhydride group containing monomers such as maleic anhydride, itaconic anhydride, and citraconic anhydride, as a precursor of a carboxy group.
  • (meth) acrylic acid is particularly preferable from the viewpoints of copolymerizability, cost, solubility, glass transition temperature, and the like.
  • the content ratio of the structural unit derived from the carboxy group-containing monomer may be appropriately set so that the acid value of the block copolymer is within the range of the specific acid value.
  • it is preferable that it is 0.05 mass% or more and 4.5 mass% or less with respect to the total mass of all the structural units of a block copolymer, and is 0.07 mass% or more and 3.7 mass% or less. More preferably.
  • the structural unit derived from the carboxy group-containing monomer Since the content ratio of the structural unit derived from the carboxy group-containing monomer is not less than the lower limit value, the effect of suppressing the development residue is expressed, and since it is not more than the upper limit value, the development adhesiveness is deteriorated and the solvent resolubility is reduced. Deterioration can be prevented.
  • the structural unit derived from a carboxy group containing monomer should just become said specific acid value, may consist of 1 type, and may contain 2 or more types of structural units.
  • the monomer whose glass transition temperature (Tgi) of the homopolymer of the monomer is 10 ° C. or higher from the viewpoint that the glass transition temperature of the dispersant used in the present invention is a specific value or higher and development adhesion is improved.
  • Tgi glass transition temperature of the homopolymer of the monomer
  • the ratio m / n of the unit number m of the structural unit of the A block and the unit number n of the structural unit of the B block is in the range of 0.05 to 1.5. In view of the dispersibility and dispersion stability of the coloring material, it is more preferably within the range of 0.1 to 1.0.
  • the weight average molecular weight Mw of the block copolymer is not particularly limited, but is preferably 1000 or more and 20000 or less, and preferably 2000 or more and 15000 or less, from the viewpoint of improving the colorant dispersibility and dispersion stability. More preferably, it is more preferably 3000 or more and 12000 or less.
  • the weight average molecular weight (Mw) is determined as a standard polystyrene equivalent value by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the method for producing the block copolymer is not particularly limited. Although a block copolymer can be produced by a known method, it is preferable to produce it by a living polymerization method. This is because chain transfer and deactivation are unlikely to occur, a copolymer having a uniform molecular weight can be produced, and dispersibility and the like can be improved.
  • the living polymerization method include a living anionic polymerization method such as a living radical polymerization method and a group transfer polymerization method, and a living cation polymerization method.
  • a copolymer can be produced by sequentially polymerizing monomers by these methods.
  • a block copolymer can be produced by first producing the A block and polymerizing the structural units constituting the B block into the A block.
  • the order of polymerization of the A block and the B block can be reversed.
  • the A block and the B block can be manufactured separately, and then the A block and the B block can be coupled.
  • block copolymer having a block part containing the structural unit represented by the general formula (I) and a block part having a solvent affinity include, for example, those described in Japanese Patent No. 4911253 A block copolymer can be mentioned as a suitable thing.
  • the polymer containing the structural unit represented by the general formula (I) an organic acid compound
  • a salt formed with a halogenated hydrocarbon as a dispersant
  • the polymer containing a repeating unit having a tertiary amine is a block copolymer
  • the organic acid compound is an acidic organic phosphorus compound such as phenylphosphonic acid or phenylphosphinic acid. And preferred from the viewpoint of excellent dispersion stability.
  • organic acid compound used for such a dispersant examples include, for example, organic acid compounds described in JP 2012-236882 A and the like.
  • the halogenated hydrocarbon is preferably at least one of allyl halides such as allyl bromide and benzyl chloride and aralkyl halides from the viewpoint of excellent dispersibility and dispersion stability of the coloring material.
  • the dispersant at least one polymer having the structural unit represented by the general formula (I) is used, and the content thereof is the type of the color material to be used, and further described below. It is appropriately selected according to the solid content concentration in the colored resin composition for color filter to be performed.
  • the content of the dispersant is 3 parts by mass or more and 45 parts by mass or less, more preferably 5 parts by mass or more and 35 parts by mass with respect to 100 parts by mass of the total solid content in the colorant dispersion from the viewpoint of dispersibility and dispersion stability. It is preferable to mix
  • the content of the dispersant is 3 parts by mass or more and 25 parts by mass or less with respect to 100 parts by mass of the total solid content in the color material dispersion. More preferably, it is blended at a ratio of 5 parts by mass or more and 20 parts by mass or less.
  • the solid content is everything except the above-mentioned solvent, and includes monomers dissolved in the solvent.
  • the solvent used in the present invention is not particularly limited as long as it is an organic solvent that does not react with each component in the colorant dispersion and can dissolve or disperse them.
  • a solvent can be used individually or in combination of 2 or more types.
  • Specific examples of the solvent include, for example, alcohol solvents such as methyl alcohol, ethyl alcohol, i-propyl alcohol and methoxy alcohol; carbitol solvents such as methoxyethoxyethanol and ethoxyethoxyethanol; ethyl acetate, butyl acetate and methoxypropion Ester solvents such as methyl acid, ethyl methoxypropionate, ethyl ethoxypropionate, ethyl lactate, methyl hydroxypropionate, ethyl hydroxypropionate, n-butyl acetate, isobutyl acetate, n-butyl butyrate, clohexanol acetate; acetone, Ke
  • the solvent used in the present invention includes propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, 2-methoxyethyl acetate, propylene glycol monomethyl ether, diethylene glycol ethyl methyl ether, butyl carbitol acetate (BCA), 3-methoxy It should be at least one selected from the group consisting of -3-methyl-1-butyl acetate, ethyl lactate, methyl 2-hydroxypropionate, and 3-methoxybutyl acetate. It is preferable from the point of aptitude.
  • the glycol ether acetate described above is used as the first solvent because of its high safety; moderate volatility; good dispersibility due to moderate solubility; It is preferable to use a system solvent.
  • a system solvent 2-methoxyethyl acetate or propylene glycol monomethyl ether acetate having a boiling point (boiling point at atmospheric pressure; the same shall apply hereinafter) of less than 150 ° C. is more preferable, and propylene glycol monomethyl ether acetate (PGMEA) is particularly preferable. preferable.
  • a solvent having an alcoholic hydroxyl group or a solvent having a boiling point of 150 ° C. or higher is preferable.
  • a 2nd solvent may be used individually by 1 type, and 2 or more types may be mixed and used for it.
  • the dispersibility is improved and the solvent resolubility is likely to be improved.
  • the solvent having an alcoholic hydroxyl group include the alcohol solvent, the carbitol solvent, and the glycol ether solvent. Specific examples include propylene glycol monomethyl ether (boiling point 121 ° C.), 3-methoxy- Examples include 3-methyl-1-butanol (boiling point 174 ° C.).
  • the content of the solvent having an alcoholic hydroxyl group is preferably 10% by mass or less, more preferably 5% by mass or less, and still more preferably 2% by mass or less in the total solvent. Moreover, 0.1 mass% or more is preferable, 0.3 mass% or more is more preferable, and 1 mass% or more is still more preferable. Within the above range, the solubility of the dispersant tends to be good, and since the dissolution of the dispersant in the first solvent is not hindered, the dispersion stability tends to be good.
  • the first solvent is a solvent having a boiling point of less than 150 ° C.
  • use of a solvent having a boiling point of 150 ° C. or more as the second solvent makes it difficult for drying unevenness to occur, hardly causes foreign matter, and tends to improve the solvent resolubility.
  • diethylene glycol ethyl methyl ether (boiling point 179 ° C.), 3-methoxy-3-methyl-1-butyl acetate (boiling point 188 ° C.), diethylene glycol ethyl methyl ether (boiling point 179 ° C.), 3 -Methoxybutyl acetate (boiling point 172 ° C.) and the like.
  • the content of the solvent having a boiling point of 150 ° C. or higher is preferably 40% by mass or less, more preferably 30% by mass or less in the total solvent. Moreover, 3 mass% or more is preferable, 5 mass% or more is more preferable, and 10 mass% or more is still more preferable. Within the above range, drying unevenness is unlikely to occur, and the drying time does not become too long and the productivity tends to be good.
  • the boiling point of the above “solvent having a boiling point of 150 ° C. or higher” is preferably 240 ° C. or lower, particularly preferably 200 ° C. or lower, from the viewpoint that the drying time does not become too long.
  • the solvent as described above is usually preferably in the range of 55% by mass to 95% by mass with respect to the total amount of the color material dispersion containing the solvent. It is preferably in the range of not less than mass% and not more than 90 mass%, more preferably in the range of not less than 70 mass% and not more than 88 mass%. Within the above range, dispersibility is improved, viscosity stability is obtained, and a target chromaticity coordinate can be achieved.
  • dispersion auxiliary resin examples include alkali-soluble resins exemplified by a colored resin composition for a color filter described later.
  • the steric hindrance of the alkali-soluble resin makes it difficult for the colorant particles to come into contact with each other, and may have the effect of stabilizing the dispersion or reducing the dispersant due to the dispersion stabilizing effect.
  • Other components include, for example, surfactants for improving wettability, silane coupling agents for improving adhesion, antifoaming agents, repellency inhibitors, antioxidants, anti-aggregation agents, and UV absorbers. Etc.
  • the color material dispersion of the present invention is used as a preliminary preparation for preparing a colored resin composition for a color filter described later. That is, the color material dispersion is P / V (total color material mass in the composition) / (color material in the composition), which is preliminarily prepared in a stage before preparing a colored resin composition for a color filter described later.
  • the method for producing the color material dispersion is not particularly limited as long as the color material is a method for obtaining a color material dispersion dispersed in a solvent with the dispersant. Especially, it is preferable to set it as either of the following two manufacturing methods from the point which is excellent in the dispersibility and dispersion stability of a coloring material.
  • the first method for producing a colorant dispersion according to the present invention includes a step of preparing the dispersant and a step of dispersing the colorant in the presence of the dispersant in a solvent. .
  • Two or more kinds of color materials may be co-dispersed in the presence of the dispersant in a solvent, or one or more kinds of color materials are dispersed or co-dispersed, and then two or more kinds of color material dispersions are mixed. By doing so, the colorant dispersion of the present invention may be obtained.
  • the second method for producing the colorant dispersion according to the present invention includes a solvent, the block copolymer, the organic acid compound, and halogenated carbonization. While mixing hydrogen and a coloring material, salt formation of at least a part of the terminal nitrogen moiety of the structural unit represented by the general formula (I) with the organic acid compound or the halogenated hydrocarbon is performed. And a step of dispersing the coloring material. Even when the color material is dispersed while forming such a salt, two or more kinds of color materials may be co-dispersed, or after one or more kinds of color materials are dispersed or co-dispersed, two or more kinds of colors are dispersed.
  • the color material dispersion of the present invention may be obtained by mixing the material dispersion.
  • the color material can be dispersed using a conventionally known disperser.
  • the dispersing machine include roll mills such as two rolls and three rolls, ball mills such as a ball mill and a vibration ball mill, bead mills such as a paint conditioner, a continuous disk type bead mill, and a continuous annular type bead mill.
  • the bead diameter to be used is preferably 0.03 mm or more and 3.0 mm or less, more preferably 0.05 or more and 2.0 mm or less.
  • the colored resin composition for a color filter according to the present invention is a colored resin composition for a color filter containing a coloring material, a dispersant, a binder component, and a solvent,
  • the color material is a blue color material, a purple color material, and C.I. I. Including Pigment Green 59
  • the dispersant is a polymer having a structural unit represented by the general formula (I).
  • the colored resin composition for a color filter of the present invention is excellent in color material dispersion stability like the color material dispersion of the present invention, and as described in the section of the color material dispersion of the present invention, A colored layer having improved solubility and an expanded blue reproduction range can be formed.
  • the colored resin composition for a color filter of the present invention contains at least a colorant, a dispersant, a binder component, and a solvent, and further contains other components as long as the effects of the present invention are not impaired. You may do it.
  • each component contained in the colored resin composition for a color filter of the present invention will be described.
  • the blue color material, purple color material, PG59, dispersant, and solvent, which are essential components among the color materials, are described above. Since it is the same as that described in the color material dispersion of the invention, description thereof is omitted here.
  • the color material in the colored resin composition for a color filter of the present invention includes, as essential components, a blue color material, a purple color material, and C.I. I. Pigment Green 59 is included, but other color materials may be used in combination in order to adjust the color tone. It is not particularly limited as long as it can form a desired color when forming the color layer of the color filter, and various organic pigments, inorganic pigments, dispersible dyes may be used alone or in combination of two or more. Can be used. Among these, organic pigments are preferably used because they have high color developability and high heat resistance.
  • the organic pigment examples include compounds classified as pigments in the Color Index (CI; issued by The Society of Dyers and Colorists), specifically, the following color index (C.I. .) Can be listed with numbers.
  • the dispersible dyes include dyes that are dispersible by imparting various substituents to the dyes or insolubilizing in a solvent by using a known lake (chlorination) technique, and low solubility. Examples thereof include dyes that can be dispersed by using in combination with a solvent. By using such a dispersible dye in combination with the dispersant, the dispersibility and dispersion stability of the dye can be improved.
  • the dispersible dye can be appropriately selected from conventionally known dyes.
  • dyes examples include azo dyes, metal complex salt azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, and phthalocyanine dyes.
  • azo dyes metal complex salt azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, and phthalocyanine dyes.
  • red color materials C.I. I. Pigment Red 177, 168, 254, etc.
  • green color material C.I. I. Pigment Green 7, 36, 58, etc.
  • the content ratio of the blue color material to the entire color material is not particularly limited as long as it is appropriately adjusted according to the desired chromaticity. Among them, it is preferable to contain 15% by mass or more and 98% by mass or less of the blue color material with respect to the total amount of the color material from the viewpoint of improving the solvent resolubility and forming a colored layer with an expanded blue reproduction range.
  • the blue color material is more preferably contained in an amount of 20% by mass or more and 90% by mass or less, still more preferably 25% by mass or more and 80% by mass or less, and particularly preferably 27% by mass or more and 70% by mass or less. .
  • the content ratio of the purple color material to the blue color material may be appropriately adjusted according to the desired chromaticity, and is not particularly limited.
  • the blue color material is contained in an amount of 3 parts by mass to 100 parts by mass with respect to 100 parts by mass. It is preferable to contain 5 parts by weight or more and 80 parts by weight or less.
  • the purple color material is preferably contained in an amount of 1% by mass to 45% by mass, more preferably 3% by mass to 40% by mass, and more preferably 5% by mass to 40% by mass with respect to the total amount of the color material. It is more preferable to contain, and it is still more preferable to contain 10 mass% or more and 40 mass% or less.
  • the content ratio of PG59 with respect to the blue color material is not particularly limited as long as it is appropriately adjusted according to the desired chromaticity.
  • the blue colorant is contained in an amount of 2 parts by mass or more and 250 parts by mass or less with respect to 100 parts by mass. It is preferable to contain 5 parts by mass or more and 200 parts by mass or less.
  • PG59 1 mass% or more and 65 mass% or less with respect to coloring material whole quantity, It is more preferable to contain 2 mass% or more and 60 mass% or less, It contains 10 mass% or more and 50 mass% or less. It is even more preferable.
  • the content ratio of the purple color material with respect to PG59 may be appropriately adjusted according to the desired chromaticity, and is not particularly limited. Among them, from the point that a solvent re-solubility is improved and a colored layer with an expanded blue reproduction range can be formed, PG59 is contained in an amount of 0.03 parts by mass to 20 parts by mass with respect to 1 part by mass. It is preferable to contain 0.05 mass part or more and 10 mass parts or less, and it is still more preferable to contain 0.1 mass part or more and 7 mass parts or less.
  • the blue colorant is preferably 15% by mass or more and 98% by mass with respect to the total amount of the colorant as a suitable blending ratio or combination.
  • the purple color material is preferably 1% by mass to 45% by mass
  • PG59 is preferably 1% by mass to 65% by mass
  • the blue color material is 20% by mass to 90% by mass
  • the purple color material is 1% by mass.
  • PG59 is more preferably 1% to 65% by mass, blue color material is 25% to 80% by mass, purple color material is 3% to 40% by mass, More preferably, PG59 is 2 mass% or more and 60 mass% or less, blue color material is 27 mass% or more and 70 mass% or less, purple color material is 10 mass% or more and 40 mass% or less, and PG59 is 10 mass% or more. 50% by mass or less It is particularly preferred.
  • the content rate of the green color material containing PG59 with respect to the whole color material is match
  • the content ratio of the green color material including PG59 with respect to the entire color material, the content ratio of the purple color material with respect to the green color material including PG59 are the content ratio of PG59 with respect to the entire color material, and the content ratio of the purple color material with respect to PG59, respectively. It is preferable that it is the same.
  • the yellow color material is 0.1% by mass or less with respect to the total amount of the color material because a colored layer with an expanded blue reproduction range can be formed. It is preferable that it is less than 0.01% by mass.
  • the photosensitive coloring resin composition for color filters of this invention in the range which does not impair the effect of this invention, other color materials other than a blue color material, a purple color material, and PG59 are further included in a color material.
  • the total content of the blue color material, the purple color material, and PG59 is more preferably 70% by mass or more and 100% by mass or less, and 80% by mass or more and 100% by mass with respect to the total color material. % Or less is even more preferable.
  • the colored resin composition for a color filter of the present invention contains a binder component in order to impart film formability and adhesion to the surface to be coated.
  • a curable binder component in order to impart film formability and adhesion to the surface to be coated.
  • the curable binder component used in forming the coloring layer of a conventionally well-known color filter can be used suitably.
  • the curable binder component include a photocurable binder component containing a photocurable resin that can be polymerized and cured by visible light, ultraviolet light, electron beam, and the like, and a thermosetting resin that can be polymerized and cured by heating. What contains the thermosetting binder component to contain can be used.
  • the photosensitive binder component which has alkali developability is used suitably.
  • the photosensitive binder component include a positive photosensitive binder component and a negative photosensitive binder component.
  • the positive photosensitive binder component include a system containing an alkali-soluble resin and an o-quinonediazide group-containing compound as a photosensitizing component.
  • the negative photosensitive binder component a system containing at least an alkali-soluble resin, a polyfunctional monomer, and a photoinitiator is preferably used.
  • a negative photosensitive binder component is preferable because a pattern can be easily formed by an existing process by a photolithography method.
  • a blue color material and a green color material such as PG58, PG7, or PG36 are combined with a negative photosensitive binder component to produce a photosensitive material for a blue colored layer.
  • the photosensitive colored resin composition absorbs around 300 nm, which is the absorption wavelength (radical generation wavelength) of the photoinitiator, so that insufficient curing inside the colored layer occurs during exposure. , Chipping at the time of development, and accompanying development, chipping and peeling easily occur.
  • the color unevenness due to irregular reflection of light when the colored layer is viewed from an oblique direction occurs.
  • the application of the next colored layer, overcoat layer, etc. causes the resin composition to flow into the gap and the coating liquid is interrupted, causing uneven coating. there were.
  • the two types of purple color material and PG59 are mixed with the blue color material, so that the combination of the two types of purple color material and PG59 hardly absorbs the wavelength around 300 nm.
  • the alkali-soluble resin, the polyfunctional monomer, and the photoinitiator constituting the negative photosensitive binder component will be specifically described.
  • the alkali-soluble resin in the present invention has an acidic group, and can be appropriately selected from those that act as a binder resin and are soluble in an alkali developer used for pattern formation.
  • the alkali-soluble resin can be based on an acid value of 40 mgKOH / g or more.
  • a preferred alkali-soluble resin in the present invention is a resin having an acidic group, usually a carboxy group, and specifically, acrylic resins such as an acrylic copolymer having a carboxy group and a styrene-acrylic copolymer having a carboxy group. And epoxy (meth) acrylate resins having a carboxy group.
  • acrylic resins such as acrylic copolymers and styrene-acrylic copolymers, and epoxy acrylate resins may be used in combination.
  • An acrylic resin such as an acrylic copolymer having a structural unit having a carboxyl group and a styrene-acrylic copolymer having a carboxyl group includes, for example, a carboxyl group-containing ethylenically unsaturated monomer and, if necessary, a copolymer. It is a (co) polymer obtained by (co) polymerizing other polymerizable monomers by a known method.
  • carboxyl group-containing ethylenically unsaturated monomer examples include (meth) acrylic acid, vinyl benzoic acid, maleic acid, maleic acid monoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, and acrylic acid dimer. It is done. Also, an addition reaction product of a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate and a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride, ⁇ -carboxy-polycaprolactone Mono (meth) acrylates can also be used.
  • anhydride containing monomers such as maleic anhydride, itaconic anhydride, and citraconic anhydride, as a precursor of a carboxyl group.
  • (meth) acrylic acid is particularly preferable from the viewpoints of copolymerizability, cost, solubility, glass transition temperature, and the like.
  • the alkali-soluble resin preferably further has a hydrocarbon ring from the viewpoint of excellent adhesion of the colored layer.
  • a hydrocarbon ring that is a bulky group in the alkali-soluble resin shrinkage during curing is suppressed, peeling from the substrate is eased, and substrate adhesion is improved.
  • the present inventors have found that the use of an alkali-soluble resin having a hydrocarbon ring suppresses the solvent resistance of the obtained colored layer, particularly the swelling of the colored layer. Although the action is unclear, the bulky hydrocarbon ring in the colored layer suppresses the movement of molecules in the colored layer, resulting in an increase in the strength of the coating and suppression of swelling by the solvent. It is estimated that.
  • hydrocarbon rings examples include aliphatic hydrocarbon rings that may have a substituent, aromatic hydrocarbon rings that may have a substituent, and combinations thereof. May have a substituent such as an alkyl group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amide group, a hydroxyl group, a nitro group, an amino group, or a halogen atom.
  • the hydrocarbon ring may be contained as a monovalent group or a divalent or higher group.
  • hydrocarbon ring examples include aliphatic hydrocarbons such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornane, tricyclo [5.2.1.0 (2,6)] decane (dicyclopentane), and adamantane.
  • Ring aromatic hydrocarbon ring such as benzene, naphthalene, anthracene, phenanthrene, fluorene, etc .; chain polycycle such as biphenyl, terphenyl, diphenylmethane, triphenylmethane, stilbene, cardo structure (9,9-diarylfluorene), etc. Is mentioned.
  • the hydrocarbon ring When an aliphatic hydrocarbon ring is included as the hydrocarbon ring, it is preferable from the viewpoint of improving the heat resistance and adhesion of the colored layer and improving the luminance of the obtained colored layer. Moreover, when the said cardo structure is included, the sclerosis
  • the alkali-soluble resin preferably has a bridged cyclic hydrocarbon ring, which is an aliphatic hydrocarbon ring having a structure in which two or more rings share two or more atoms.
  • Specific examples of the bridged cyclic hydrocarbon ring include norbornane, isobornane, adamantane, tricyclo [5.2.1.0 (2,6)] decane, tricyclo [5.2.1.0 (2,6)].
  • Decene, tricyclopentene, tricyclopentane, tricyclopentadiene, dicyclopentadiene; groups in which a part of these groups are substituted with a substituent are mentioned.
  • substituents examples include an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, a hydroxyl group, a carbonyl group, a nitro group, an amino group, and a halogen atom.
  • the lower limit of the number of carbon atoms in the crosslinked cyclic hydrocarbon ring is preferably 5 or more, and particularly preferably 7 or more, from the viewpoint of compatibility with other materials and solubility in an alkali developer.
  • the upper limit is preferably 12 or less, and particularly preferably 10 or less.
  • the alkali-soluble resin preferably has a maleimide structure represented by the following general formula (III).
  • R M represents an optionally substituted hydrocarbon ring.
  • the alkali-soluble resin has a maleimide structure represented by the general formula (III), it has a nitrogen atom in the hydrocarbon ring, and therefore is a basic polymer that has a structural unit represented by the general formula (I).
  • the compatibility with the dispersant is very good, the development speed is high, and the effect of suppressing development residue is improved.
  • R M of the general formula (III) specific examples of the optionally substituted hydrocarbon ring, those similar to the specific example of the hydrocarbon ring.
  • an aliphatic hydrocarbon ring such as cyclopentyl group, cyclohexyl group, cyclooctyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group, diethylphenyl group, methoxyphenyl group, benzyl group, hydroxyphenyl group
  • An aromatic hydrocarbon ring such as a naphthyl group, and a group in which a part of these groups is substituted with a substituent are exemplified.
  • the alkali-soluble resin used in the present invention it is easy to adjust the amount of each constituent unit by using an acrylic copolymer having a constituent unit having a hydrocarbon ring separately from the constituent unit having a carboxy group. This is preferable because the amount of the structural unit having a hydrocarbon ring is increased to easily improve the function of the structural unit.
  • the acrylic copolymer having a structural unit having a carboxy group and the hydrocarbon ring is prepared by using an ethylenically unsaturated monomer having a hydrocarbon ring as the above-mentioned “other monomer capable of copolymerization”. be able to.
  • Examples of the ethylenically unsaturated monomer having a hydrocarbon ring include cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, adamantyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, and phenoxyethyl. (Meth) acrylate, styrene, etc. are mentioned.
  • cyclohexyl (meth) acrylate dicyclopentanyl (meth) acrylate, adamantyl
  • the alkali-soluble resin used in the present invention preferably has an ethylenic double bond in the side chain.
  • the alkali-soluble resins, or the alkali-soluble resin and the polyfunctional monomer can form a cross-linked bond in the curing step of the resin composition at the time of producing the color filter.
  • the film strength of the cured film is further improved and the development resistance is improved, and the thermal contraction of the cured film is suppressed and the adhesiveness with the substrate is excellent.
  • the method for introducing an ethylenic double bond into the alkali-soluble resin may be appropriately selected from conventionally known methods.
  • a method of introducing an ethylenic double bond into a side chain by adding a compound having both an epoxy group and an ethylenic double bond in the molecule, such as glycidyl (meth) acrylate, to the carboxyl group of the alkali-soluble resin Or by introducing a structural unit having a hydroxyl group into a copolymer, adding a compound having an isocyanate group and an ethylenic double bond in the molecule, and introducing an ethylenic double bond into the side chain.
  • a compound having both an epoxy group and an ethylenic double bond in the molecule such as glycidyl (meth) acrylate
  • the alkali-soluble resin of the present invention may further contain other structural units such as a structural unit having an ester group such as methyl (meth) acrylate and ethyl (meth) acrylate.
  • the structural unit having an ester group not only functions as a component that suppresses alkali solubility of the colored resin composition for a color filter, but also functions as a component that improves the solubility in a solvent and further the solvent resolubility.
  • the alkali-soluble resin in the present invention is preferably an acrylic resin such as an acrylic copolymer and a styrene-acrylic copolymer having a structural unit having a carboxyl group and a structural unit having a hydrocarbon ring, It is an acrylic resin such as an acrylic copolymer and a styrene-acrylic copolymer having a structural unit having a carboxyl group, a structural unit having a hydrocarbon ring, and a structural unit having an ethylenic double bond. Is more preferable.
  • the alkali-soluble resin can be made into an alkali-soluble resin having desired performance by appropriately adjusting the charged amount of each structural unit.
  • the charged amount of the carboxyl group-containing ethylenically unsaturated monomer is preferably 5% by mass or more and more preferably 10% by mass or more with respect to the total amount of the monomer from the viewpoint of obtaining a good pattern.
  • the amount of the carboxyl group-containing ethylenically unsaturated monomer is preferably 50% by mass or less, and 40% by mass or less with respect to the total amount of monomers. More preferably.
  • the coating film obtained has sufficient solubility in an alkaline developer, and the proportion of the carboxyl group-containing ethylenically unsaturated monomer is the upper limit.
  • the proportion of the carboxyl group-containing ethylenically unsaturated monomer is the upper limit.
  • an acrylic resin such as an acrylic copolymer having a structural unit having an ethylenic double bond and a styrene-acrylic copolymer, which is more preferably used as an alkali-soluble resin
  • an epoxy group and an ethylenic double bond are used.
  • the amount of the compound having a bond is preferably 10% by mass or more and 95% by mass or less, and more preferably 15% by mass or more and 90% by mass or less with respect to the charged amount of the carboxyl group-containing ethylenically unsaturated monomer.
  • the preferred weight average molecular weight (Mw) of the carboxy group-containing copolymer is preferably in the range of 1,000 to 50,000, more preferably 3,000 to 20,000. If it is less than 1,000, the binder function after curing may be remarkably lowered. If it exceeds 50,000, pattern formation may be difficult during development with an alkali developer.
  • the weight average molecular weight (Mw) of the carboxy group-containing copolymer can be measured by a Shodex GPC System-21H using polystyrene as a standard substance and THF as an eluent.
  • Epoxy (meth) acrylate resin which has a carboxy group Epoxy (meth) obtained by making the reaction product of an epoxy compound and unsaturated group containing monocarboxylic acid react with an acid anhydride. Acrylate compounds are suitable.
  • the epoxy compound, unsaturated group-containing monocarboxylic acid, and acid anhydride can be appropriately selected from known ones.
  • the epoxy (meth) acrylate resin having a carboxy group may be used alone or in combination of two or more.
  • the alkali-soluble resin is preferably selected from those having an acid value of 50 mgKOH / g or more from the viewpoint of developability (solubility) with respect to an alkaline aqueous solution used for the developer.
  • the alkali-soluble resin preferably has an acid value of 70 mgKOH / g or more and 300 mgKOH / g or less from the viewpoint of developability (solubility) with respect to an aqueous alkali solution used for the developer and adhesion to the substrate. It is preferable that it is 80 mgKOH / g or more and 280 mgKOH / g or less.
  • the acid value can be measured according to JIS K 0070.
  • the ethylenically unsaturated bond equivalent in the case where the side chain of the alkali-soluble resin has an ethylenically unsaturated group improves the film strength of the cured film, improves the development resistance, and obtains the effect of excellent adhesion to the substrate. From the viewpoint, it is preferably in the range of 100 to 2000, and particularly preferably in the range of 140 to 1500. When the ethylenically unsaturated bond equivalent is 2000 or less, the development resistance and adhesion are excellent. Moreover, since the ratio of other structural units, such as the structural unit which has the said carboxy group, and the structural unit which has a hydrocarbon ring, can be relatively increased if it is 100 or more, it is excellent in developability and heat resistance. Yes.
  • the ethylenically unsaturated bond equivalent is a weight average molecular weight per mole of the ethylenically unsaturated bond in the alkali-soluble resin, and is represented by the following formula (1).
  • Ethylenically unsaturated bond equivalent (g / mol) W (g) / M (mol) (In Formula (1), W represents the mass (g) of the alkali-soluble resin, and M represents the number of moles (mol) of the ethylenic double bond contained in the alkali-soluble resin W (g).)
  • the ethylenically unsaturated bond equivalent is determined, for example, by measuring the number of ethylenic double bonds contained in 1 g of the alkali-soluble resin in accordance with the test method for the iodine value described in JIS K 0070: 1992. It may be calculated.
  • the alkali-soluble resin used in the colored resin composition for color filters may be used alone or in combination of two or more, and the content is not particularly limited, but for color filters.
  • the alkali-soluble resin is preferably 5% by mass or more and 60% by mass or less, more preferably 10% by mass or more and 40% by mass or less, based on the total solid content of the colored resin composition.
  • the content of the alkali-soluble resin is not less than the above lower limit, sufficient alkali developability can be easily obtained, and when the content of the alkali-soluble resin is not more than the above upper limit, film roughness or lack of pattern can be caused during development. It is easy to suppress.
  • the polyfunctional monomer used in the colored resin composition for a color filter is not particularly limited as long as it can be polymerized by the photoinitiator, and a compound having two or more ethylenically unsaturated double bonds is usually used.
  • a polyfunctional (meth) acrylate is preferably used, and particularly has two or more acryloyl groups or methacryloyl groups.
  • Such polyfunctional (meth) acrylate may be appropriately selected from conventionally known ones. Specific examples include those described in JP2013-029832A.
  • polyfunctional (meth) acrylates may be used alone or in combination of two or more. Moreover, when the photocurability (high sensitivity) is requested
  • a polyfunctional monomer is 5 mass% or more and 60 with respect to the solid content whole quantity of the colored resin composition for color filters. It is within the range of 10% by mass or less and more preferably 40% by mass or less.
  • the content of the polyfunctional monomer is not less than the above lower limit, photocuring proceeds sufficiently, and the exposed portion can suppress elution during development, and when the content of the polyfunctional monomer is not more than the above upper limit, alkali development Sex is enough.
  • Photoinitiator There is no restriction
  • the initiator include aromatic ketones such as benzophenone, 4,4′-bisdiethylaminobenzophenone and 4-methoxy-4′-dimethylaminobenzophenone, benzoin ethers such as benzoin methyl ether, and benzoin such as ethylbenzoin.
  • Biimidazoles such as 2- (o-chlorophenyl) -4,5-phenylimidazole dimer, halo such as 2-trichloromethyl-5- (p-methoxystyryl) -1,3,4-oxadiazole Methyloxadiazole compounds, halomethyl-S-triazine compounds such as 2- (4-butoxy-naphth-1-yl) -4,6-bis-trichloromethyl-S-triazine, 2,2-dimethoxy-1, 2-diphenylethane-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2 Morpholinopropanone, 1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,1-hydroxy-cyclohexyl-phenyl ketone, benzyl, benzoylbenzoic acid, methyl benzoylbenzoate, 4 -Benzoyl
  • 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -1- Butanone, 4,4′-bis (diethylamino) benzophenone, and diethylthioxanthone are preferably used.
  • a sensitivity is obtained by combining an ⁇ -aminoacetophenone initiator such as 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one with a thioxanthone initiator such as diethylthioxanthone.
  • the total content of ⁇ -aminoacetophenone initiator and thioxanthone initiator is preferably 5% by mass or more and 15% by mass or less based on the total solid content of the colored resin composition.
  • the amount of the initiator is 15% by mass or less, sublimates during the production process are reduced, which is preferable.
  • the amount of the initiator is 5% by mass or more, development resistance such as water stain is improved.
  • the initiator preferably contains an oxime ester photoinitiator from the viewpoint of improving sensitivity.
  • an oxime ester photoinitiator By using an oxime ester photoinitiator, in-plane line width variations are easily suppressed when forming a fine line pattern. Furthermore, by using an oxime ester photoinitiator, the development resistance is improved, and the effect of suppressing the occurrence of water stain tends to be increased.
  • water stain means that, when a component that enhances alkali developability is used, a trace of water stain is generated after rinsing with pure water after alkali development. Such a water stain disappears after post-baking, so there is no problem as a product. Arise.
  • the inspection sensitivity of the inspection apparatus is lowered in the appearance inspection, the yield of the final color filter product is lowered as a result, which becomes a problem.
  • the oxime ester-based photoinitiator those having an aromatic ring are preferable from the viewpoint of reducing contamination of the colored resin composition for color filters and degradation of the apparatus due to decomposition products, and having condensed rings including aromatic rings. More preferred are those having a condensed ring containing a benzene ring and a heterocycle.
  • oxime ester photoinitiators examples include 1,2-octadion-1- [4- (phenylthio)-, 2- (o-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2-methyl) Benzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime), JP 2000-80068 A, JP 2001-233842 A, Special Table 2010-527339, Special Table 2010-527338, It can be appropriately selected from oxime ester photoinitiators described in JP2013-041153A.
  • Irgacure OXE-02 having a carbazole skeleton (manufactured by BASF), Adeka Arcles NCI-831 (manufactured by ADEKA), TR-PBG-304 (manufactured by Changzhou Power Electronics Co., Ltd.), ADEKA having a diphenyl sulfide skeleton Arcles NCI-930 (manufactured by ADEKA), TR-PBG-345, TR-PBG-3057 (manufactured by Changzhou Power Electronics New Materials Co., Ltd.), Irgacure OXE-01 (manufactured by BASF), TR-PBG having a fluorene skeleton -365 (manufactured by Changzhou Powerful Electronic New Materials Co., Ltd.) may be used.
  • an oxime ester photoinitiator having a diphenyl sulfide skeleton or a fluorene skeleton from the viewpoint of luminance. It is preferable to use an oxime ester photoinitiator having a carbazole skeleton from the viewpoint of high sensitivity. Moreover, it is preferable to use two or more kinds of oxime ester photoinitiators in terms of easily improving development resistance and luminance, and having a high effect of suppressing the occurrence of water stain.
  • the combined use of two types of oxime ester photoinitiators having a diphenyl sulfide skeleton, or the combined use of an oxime ester photoinitiator having a diphenyl sulfide skeleton and an oxime ester photoinitiator having a fluorene skeleton is high in luminance and heat resistance. It is preferable from the point of high property.
  • an oxime ester-based photoinitiator having a carbazole skeleton and an oxime ester-based photoinitiator having a fluorene skeleton or an oxime ester-based photoinitiator having a diphenyl sulfide is excellent in sensitivity and water stain generation suppression effect. Is preferable.
  • a photoinitiator having a tertiary amine structure in combination with an oxime ester photoinitiator from the viewpoint of suppressing water stain and improving sensitivity. Since the photoinitiator having a tertiary amine structure has a tertiary amine structure that is an oxygen quencher in the molecule, radicals generated from the initiator are hardly deactivated by oxygen, and sensitivity can be improved. is there.
  • Examples of commercially available photoinitiators having the tertiary amine structure include 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (for example, Irgacure 907, manufactured by BASF), 2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -1-butanone (eg Irgacure 369, manufactured by BASF), 4,4′-bis (diethylamino) benzophenone (eg Hycure ABP, Kawaguchi Pharmaceutical).
  • 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one for example, Irgacure 907, manufactured by BASF
  • 2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -1-butanone eg Irgacure 369, manufactured by BASF
  • combining an oxime ester photoinitiator with a thioxanthone initiator is preferable from the viewpoint of adjusting sensitivity, suppressing water stain, and improving development resistance.
  • Two or more oxime ester photoinitiators and a thioxanthone photoinitiator are preferable.
  • a combination of initiators is preferable in that brightness and development resistance are improved, sensitivity adjustment is easy, water stain generation suppression effect is high, and development resistance is improved.
  • the content of the photoinitiator used in the colored resin composition for a color filter of the present invention is usually about 0.01 parts by mass or more and 100 parts by mass or less, preferably 5 parts by mass with respect to 100 parts by mass of the polyfunctional monomer.
  • the amount is 60 parts by mass or less. If this content is not less than the above lower limit, the photocuring is sufficiently advanced and the exposed portion is prevented from being eluted during development, while if it is not more than the above upper limit, the yellowing of the resulting colored layer is weakened and the luminance is reduced. It can suppress that it falls.
  • the total content of two or more oxime ester photoinitiators is based on the total solid content of the colored resin composition for color filters. 0.1% by mass or more and 12.0% by mass or less, more preferably 1.0% by mass or more and 8.0% by mass or less in the range of sufficiently exhibiting the combined effect of these photoinitiators. To preferred.
  • the binder component used in the colored resin composition for a color filter of the present invention preferably has a total content of 35% by mass to 97% by mass with respect to the total solid content of the colored resin composition for a color filter. It is more preferable to blend in a proportion of not less than mass% and not more than 96 mass%. If it is more than the said lower limit, the colored layer excellent in hardness and the adhesiveness with a board
  • the colored resin composition for a color filter may contain various additives as necessary.
  • additives include, in addition to antioxidants, mercapto compounds, polymerization terminators, chain transfer agents, leveling agents, plasticizers, surfactants, antifoaming agents, silane coupling agents, ultraviolet absorbers, adhesion promoters. Etc.
  • the colored resin composition for a color filter of the present invention further contains an antioxidant because heat resistance is improved, fading of the coloring material is suppressed, and luminance is improved.
  • the antioxidant may be appropriately selected from conventionally known antioxidants. Specific examples of antioxidants include, for example, hindered phenol antioxidants, amine antioxidants, phosphorus antioxidants, sulfur antioxidants, hydrazine antioxidants, and the like. From the viewpoint, it is preferable to use a hindered phenol-based antioxidant.
  • the hindered phenol antioxidant contains at least one phenol structure, and has a structure in which a substituent having 4 or more carbon atoms is substituted on at least one of the 2-position and 6-position of the hydroxyl group of the phenol structure. Means an antioxidant.
  • hindered phenol antioxidant examples include, for example, dibutylhydroxytoluene (BHT), pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: Irganox 1010, manufactured by BASF), 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate (trade name: Irganox 3114, manufactured by BASF), 2,4,6 Tris (4-hydroxy-3,5-di-tert-butylbenzyl) mesitylene (trade name: Irganox 1330, manufactured by BASF), 6- (4-hydroxy-3,5-di-tert-butylanilino) -2 , 4-Bis (octylthio) -1,3,5-triazine (trade name: Irganox 565) BASF), 2,2′-thiodiethylbis [
  • oligomer-type and polymer-type compounds having a hindered phenol structure can also be used.
  • pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: trade name: IRGANOX1010, manufactured by BASF) is preferable from the viewpoint of heat resistance and light resistance.
  • a hindered phenol antioxidant having a molecular weight of 1000 or less and a molecular weight per phenolic hydroxyl group of 280 equivalents or less, and further a molecular weight of 500 or less and a molecular weight per phenolic hydroxyl group of 200 equivalents or less.
  • Such an antioxidant has high fluidity and many active points per weight, so that radical trapping suppresses color material aggregation due to rapid curing shrinkage during exposure and post-baking, It is presumed that the above effect is easily obtained due to suppression of yellowing.
  • examples of such an antioxidant include 6,6′-di-tert-butyl-4,4′-butylidene di-m-cresol (trade name: ADK STAB AO-40, manufactured by ADEKA).
  • the latent antioxidant is a compound having a protecting group that can be removed by heating, and exhibiting an antioxidant function when the protecting group is eliminated. Among them, those which are easy to remove the protecting group by heating at 150 ° C. or higher are preferable.
  • the latent antioxidant as described in international publication 2014/021023 is mentioned.
  • latent antioxidants examples include latent hindered phenol antioxidants in which the phenolic hydroxyl group of the hindered phenol antioxidant is protected with a protecting group that can be removed by heating.
  • latent hindered phenolic antioxidants phenolic hydroxyl groups of hindered phenolic antioxidants, acid anhydrides, acid chlorides, Boc reagents, alkyl halide compounds, silyl chloride compounds, allyl ether compounds, etc. And the reaction product.
  • a structure in which the hydrogen of the phenol group of the hindered phenol antioxidant is substituted with a carbamate protecting group such as a t-butoxycarbonyl group is preferably used. Examples include, but are not limited to, the following chemical formulas (a) to (c).
  • the method for producing the latent antioxidant is not particularly limited.
  • the colored resin composition for a color filter according to the present invention contains, as a photosensitive colored resin composition, a combination of the oxime ester photoinitiator and an antioxidant in a synergistic effect, and the outer portion of the mask opening. Curing with weak light penetrating into the surface is suppressed, resulting in chipping during development, and subsequent development of chipping and peeling, and color unevenness due to irregular reflection of light when the colored layer is viewed from an oblique direction. Furthermore, it is preferable from the point of being difficult to generate.
  • antioxidant is 0.05 mass part or more and 10.00 mass part or less with respect to 100 mass parts of total solids in a colored resin composition, 0.10 More preferably, it is at least part by mass and no more than 5.00 parts by mass. If it is more than the said lower limit, it is excellent in heat resistance and light resistance. On the other hand, if it is below the said upper limit, the colored resin composition of this invention can be made into a highly sensitive photosensitive resin composition.
  • the content of the antioxidant is 1 part by mass of the antioxidant with respect to 100 parts by mass of the total amount of the oxime ester photoinitiator. It is preferably 250 parts by mass or less, more preferably 3 parts by mass or more and 80 parts by mass or less, and still more preferably 5 parts by mass or more and 45 parts by mass or less. If it is in the said range, it is excellent in the effect of the said combination.
  • the colored resin composition for a color filter of the present invention further contains a mercapto compound from the viewpoint of improving the effect of suppressing the occurrence of water stain.
  • the colored resin composition for a color filter of the present invention contains a combination of the oxime ester photoinitiator and a mercapto compound as a photosensitive colored resin composition, which improves development resistance and generates water stains. This is preferable because the suppression effect is further improved, and when forming a fine line pattern, the linearity is further improved, and the ability to form a fine line pattern as designed for the mask line width is improved.
  • oxime ester photoinitiator and the mercapto compound are contained in combination, a synergistic effect makes it more difficult to cause erosion during development, and accompanying development, chipping or peeling, and a colored layer is formed from an oblique direction. This is preferable from the viewpoint that color unevenness due to irregular reflection of light when viewed is further less likely to occur.
  • “Improved linearity” means that the end of the colored layer formed in the development step after applying the colored composition has few irregularities and is linear or substantially linear.
  • the mercapto compound can function as a chain transfer agent, and has the property of receiving radicals from slowly reacting radicals to accelerate the reaction and improve curability.
  • Examples of mercapto compounds include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2-mercapto-5-methoxybenzothiazole, 2-mercapto-5-methoxybenzimidazole, and 3-mercaptopropionic acid.
  • the mercapto compound one or a combination of two or more may be used. Among them, one or more selected from the group consisting of polyfunctional mercapto compounds having two or more mercapto groups in one molecule may be used. It is preferable from the viewpoint that the crosslink density is increased and the effect of suppressing water stain is improved.
  • a secondary mercapto compound having a secondary mercapto group in which the carbon atom to which the mercapto group is bonded is a secondary carbon atom is preferable from the viewpoint that even when stored for a long period of time, a good water stain suppression effect is easily maintained. Further, a polyfunctional secondary mercapto compound having two or more secondary mercapto groups in one molecule is more preferable.
  • the content of the mercapto compound used in the colored resin composition for color filter is not particularly limited, but the mercapto compound is 0.2% by mass or more and 7% by mass with respect to the total solid content of the colored resin composition for color filter. % Or less, and more preferably in the range of 0.5% by mass or more and 5% by mass or less from the viewpoint of sufficiently exhibiting the above effects.
  • the colored resin composition for a color filter of the present invention further contains an ultraviolet absorber from the viewpoint that a colored layer with improved contrast can be formed.
  • an ultraviolet absorber suitably from a conventionally well-known thing.
  • Specific examples of the ultraviolet absorber include benzotriazole compounds, benzophenone compounds, triazine compounds, and the like. Among them, it is preferable to use a benzotriazole-based compound from the viewpoint that a colored layer with improved contrast can be formed.
  • benzotriazole compounds examples include 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- (2-hydroxy-5-tert-butylphenyl) -2H-benzotriazole, octyl-3 [3- t-Butyl-4-hydroxy-5- (5-chloro-2H-benzotriazol-2-yl) phenyl] propionate and 2-ethylhexyl-3- [3-t-butyl-4-hydroxy-5- (5- Chloro-2H-benzotriazol-2-yl) phenyl] propionate, 2- [2-hydroxy-3,5-bis ( ⁇ , ⁇ -dimethylbenzyl) phenyl] -2H-benzotriazole, 2- (3- t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3,5-di-t-amyl-2- Droxyphenyl) benzotriazole, 2- (2′-hydroxy-5′-
  • Examples of commercially available products include “TINUVIN P”, “TINUVIN PS”, “TINUVIN 109”, “TINUVIN 234”, “TINUVIN 326”, “TINUVIN 328”, “TINUVIN 329”, and “TINUVIN 384-2” manufactured by BASF. ”,“ TINUVIN 900 ”,“ TINUVIN 928 ”,“ TINUVIN 99-2 ”,“ TINUVIN 1130 ”, and the like.
  • benzotriazole-based compound a benzotriazole-based compound represented by the following general formula (IV) is preferable because a colored layer with improved contrast can be formed.
  • R 11 and R 12 are each independently an alkyl group having 1 to 20 carbon atoms which may be substituted with a hydrogen atom or a phenyl group, and X represents a hydrogen atom or a chlorine atom. .
  • R 12 is preferably a methyl group, a t-butyl group, a t-amyl group, a t-octyl group, or an ⁇ , ⁇ -dimethylbenzyl group
  • R 11 is a hydrogen atom
  • An atom, a t-butyl group, a t-amyl group, or an ⁇ , ⁇ -dimethylbenzyl group is preferable.
  • an ultraviolet absorber is 0.05 mass part or more with respect to 100 mass parts of total solids in a colored resin composition. It is preferably 10.00 parts by mass or less, and more preferably 0.10 parts by mass or more and 5.00 parts by mass or less. If it is more than the said lower limit, it is excellent in heat resistance and light resistance. On the other hand, if it is below the said upper limit, the colored resin composition of this invention can be made into a highly sensitive photosensitive resin composition.
  • the colored resin composition for a color filter of the present invention contains a combination of the oxime ester photoinitiator and an ultraviolet absorber as a colored resin composition, and has a synergistic effect. It is preferable in that it is less likely to cause chipping and peeling, and color unevenness due to irregular reflection of light when the colored layer is viewed from an oblique direction is further less likely to occur.
  • the content of the ultraviolet absorber is 1 part by mass with respect to 100 parts by mass of the total amount of the oxime ester photoinitiator.
  • the amount is preferably 250 parts by mass or less, more preferably 3 parts by mass or more and 80 parts by mass or less, and still more preferably 5 parts by mass or more and 45 parts by mass or less. If it is in the said range, it is excellent in the effect of the said combination.
  • surfactant and the plasticizer include those described in JP 2013-029832 A, for example.
  • the colored resin composition for a color filter of the present invention further contains a silane coupling agent from the viewpoint of improving peeling prevention of the coating film.
  • the silane coupling agent include KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-903, KBE-903, KBM573, KBM-403, KBE-402, KBE-403, Examples thereof include KBM-303, KBM-802, KBM-803, KBE-9007, X-12-967C (manufactured by Shin-Etsu Silicone).
  • KBM-502, KBM-503, KBE-502, KBE-503, and KBM-5103 having a methacrylic group and an acrylic group are preferable from the viewpoint of adhesion of the SiN substrate.
  • the content of the silane coupling agent is preferably 0.05 parts by mass or more and 10.0 parts by mass or less with respect to 100 parts by mass of the total solid content in the colored resin composition. More preferably, it is 1 part by mass or more and 5.0 parts by mass or less. If it is more than the said lower limit and below the said upper limit, it is excellent in the peeling suppression of a coating film.
  • the total content of the color material is 3% by mass or more and 65% by mass or less, more preferably 4% by mass or more and 60% by mass or less, based on the total solid content of the colored resin composition for color filters. Is preferred. If it is more than the said lower limit, the colored layer at the time of apply
  • the content of the color material is 15% by mass or more and 65% by mass or less, more preferably 25% by mass with respect to the total solid content of the color resin composition for color filters. It is preferable to mix
  • the content of the dispersant is not particularly limited as long as it can uniformly disperse the coloring material.
  • the content of the dispersant is 1 with respect to the total solid content of the colored resin composition for a color filter. It can be used in the range of mass% to 40 mass%.
  • blend in the ratio of 2 mass% or more and 30 mass% or less with respect to solid content whole quantity of the colored resin composition for color filters, and it is preferable to mix
  • the content of the dispersing agent is 2% by mass or more and 25% by mass or less, more preferably 3%, based on the total solid content of the colored resin composition for color filters. It is preferable to mix in a proportion of not less than 20% by mass and not more than 20% by mass. Moreover, what is necessary is just to set content of a solvent suitably in the range which can form a colored layer accurately. Usually, it is preferably in the range of 55% by mass to 95% by mass with respect to the total amount of the colored resin composition for a color filter containing the solvent, and in particular, in the range of 65% by mass to 88% by mass. More preferably. When the content of the solvent is within the above range, the coating property can be excellent.
  • the blue color material in the color material, purple color is used from the viewpoint of suppressing blurring, peeling, and color unevenness during development.
  • the color material ratio of the color material and PG59 is preferably a color material ratio that satisfies the following average transmittance.
  • a test color material dispersion is prepared so that a predetermined color material ratio is obtained using an appropriate dispersant and solvent, and the test color material dispersion is prepared so that the total content of color materials is 0.001% by mass.
  • the average transmittance in the range of 280 nm to 360 nm is preferably 36% or more, more preferably 39% or more, and still more preferably 40% or more.
  • the spectral transmittance can be measured using an ultraviolet-visible spectrophotometer (for example, an ultraviolet-visible near-infrared spectrophotometer UV-3150 manufactured by Shimadzu Corporation).
  • an ultraviolet-visible spectrophotometer for example, an ultraviolet-visible near-infrared spectrophotometer UV-3150 manufactured by Shimadzu Corporation.
  • the appropriate dispersant and solvent specifically, for example, the dispersant and solvent used in the color material dispersion liquid of Example 1 described later can be used. It can be prepared in the same manner as the colorant dispersion of Example 1.
  • the blue color material in the color material is suppressed in terms of suppressing blurring, peeling, and color unevenness during development.
  • the color material ratio (mass ratio) of the purple color material and PG59 is preferably a color material ratio that satisfies the following average transmittance.
  • the color material ratio of the blue color material, purple color material, and PG59 in the color material is maintained, and 1 / 60,000 of the color material concentration of the cured film (total mass of the color material / total mass of the solid content of the cured film).
  • a diluted test color material dispersion having a color material concentration (total color material mass / total color material dispersion containing solvent) is prepared, and the diluted test color material dispersion is placed in a quartz cell having an optical path length of 10 mm and spectrally transmitted.
  • the average transmittance in the range of 280 nm to 360 nm is preferably 42% or more, more preferably 44% or more, and even more preferably 46% or more.
  • the spectral transmittance can be measured using an ultraviolet-visible spectrophotometer as described above.
  • the dilution test color material dispersion specifically includes, for example, a blue color material, a purple color material, and PG59 at a desired ratio based on the color material ratio in the cured film, and the color of Example 1 described later.
  • a colorant dispersion was prepared in the same manner as in Example 1 using the dispersant and solvent used in the material dispersion, and the colorant concentration of the cured film (total mass of the colorant / total mass of the solid content of the cured film) was 6. It can be prepared by diluting with a solvent such as PGMEA so that the colorant concentration is 1 / 10,000 (total colorant mass / total colorant dispersion containing solvent).
  • the P / V ratio ((total color material mass) / (total solid content other than color material in the composition) ratio) is a blue reproduction range. Is preferably 0.10 or more, more preferably 0.15 or more, and still more preferably 0.20 or more.
  • solvent resolubility, development residue, development From the viewpoint of excellent adhesion, development resistance, development chipping and unevenness generation suppression effect, contrast and the like, it is preferably 0.60 or less, more preferably 0.50 or less, and 0.45 or less. Is still more preferable, and it is especially preferable that it is 0.35 or less.
  • x 0.120 or more and 0.147 or less
  • y 0.038 or more and 0.180 or less are preferably displayed.
  • X 0.122 or more and 0.147 or less
  • the color material is 43% by mass to 93% by mass, more preferably 43% by mass to 90% by mass, the purple color material is 5% by mass to 39% by mass, and PG59 is 1% by mass to 30% by mass. Is preferred.
  • the color material is 35% by mass to 98% by mass, more preferably 35% by mass to 90% by mass, the purple color material is 1% by mass to 23% by mass, and PG59 is 1% by mass to 49% by mass. Is preferred.
  • the color material is 25% by mass or more and 98% by mass or less, more preferably 27% by mass or more and 90% by mass or less, the purple color material is 1% by mass or more and 26% by mass or less, and PG59 is 1% by mass or more and 53% by mass or less.
  • the color material is preferably 27% by mass or more and 89% by mass or less
  • the purple color material is 1% by mass or more and 26% by mass or less
  • PG59 is preferably 10% by mass or more and 60% by mass or less.
  • the color material is preferably 26% by mass to 73% by mass
  • the purple color material is preferably 1% by mass to 13% by mass
  • PG59 is preferably 21% by mass to 65% by mass.
  • the film thickness of the cured film is a film after applying the colored resin composition for color filter, drying, exposing to cure the polyfunctional monomer, and then post-baking in a clean oven at 230 ° C. for 30 minutes. Thickness.
  • the method for producing the colored resin composition for a color filter of the present invention is not particularly limited.
  • the color material dispersion of the present invention includes an alkali-soluble resin, a polyfunctional monomer, a photoinitiator, and as necessary. It can be obtained by adding other components and mixing them using a known mixing means.
  • each color material dispersion liquid is prepared, and each color material dispersion liquid, a binder component, and other components as necessary, using a known mixing means. It can be obtained by mixing.
  • the color filter according to the present invention is a color filter comprising at least a substrate and a colored layer provided on the substrate, and at least one of the colored layers is a colored resin composition for a color filter according to the present invention. It has a colored layer which is a cured product.
  • FIG. 1 is a schematic sectional view showing an example of the color filter of the present invention.
  • the color filter 10 of the present invention has a substrate 1, a light shielding part 2, and a colored layer 3.
  • At least one of the colored layers used in the color filter of the present invention is a cured product of the colored resin composition for a color filter according to the present invention, that is, a colored layer formed by curing the colored resin composition.
  • the colored layer is usually formed in an opening of a light-shielding part on the substrate to be described later, and is usually composed of a colored pattern of three or more colors.
  • the arrangement of the colored layers is not particularly limited, and for example, a general arrangement such as a stripe type, a mosaic type, a triangle type, or a four-pixel arrangement type can be used.
  • variety, area, etc. of a colored layer can be set arbitrarily.
  • the thickness of the colored layer is appropriately controlled by adjusting the coating method, the solid content concentration, the viscosity, and the like of the colored resin composition for a color filter, but is usually preferably in the range of 1 ⁇ m to 5 ⁇ m.
  • the colored layer can be formed by the following method, for example.
  • a coating means such as a spray coating method, a dip coating method, a bar coating method, a roll coating method, a spin coating method, or a die coating method. Apply to form a wet coating.
  • spin coating and die coating can be preferably used.
  • Examples of the light source used for exposure include ultraviolet rays such as a low-pressure mercury lamp, a high-pressure mercury lamp, and a metal halide lamp, and an electron beam.
  • the exposure amount is appropriately adjusted depending on the light source used, the thickness of the coating film, and the like.
  • the heating conditions are appropriately selected depending on the blending ratio of each component in the colored resin composition for the color filter to be used, the thickness of the coating film, and the like.
  • a coating film is formed with a desired pattern by melt
  • a solution in which an alkali is dissolved in water or a water-soluble solvent is usually used.
  • An appropriate amount of a surfactant or the like may be added to the alkaline solution.
  • a general method can be adopted as the developing method.
  • the developer is usually washed and the cured coating film of the colored resin composition for color filters is dried to form a colored layer.
  • the heating conditions are not particularly limited and are appropriately selected depending on the application of the coating film.
  • the light shielding part in the color filter of the present invention is formed in a pattern on a substrate to be described later, and can be the same as that used as a light shielding part in a general color filter.
  • the pattern shape of the light shielding portion is not particularly limited, and examples thereof include a stripe shape and a matrix shape.
  • the light shielding part may be a metal thin film such as chromium by sputtering, vacuum deposition or the like.
  • the light shielding part may be a resin layer in which light shielding particles such as carbon fine particles, metal oxides, inorganic pigments, and organic pigments are contained in a resin binder.
  • the thickness of the light-shielding part is set to about 0.2 ⁇ m to 0.4 ⁇ m in the case of a metal thin film, and about 0.5 ⁇ m to 2 ⁇ m in the case where a black pigment is dispersed or dissolved in a binder resin. Set by.
  • substrate As the substrate, a transparent substrate or a silicon substrate, which will be described later, or an aluminum, silver, or silver / copper / palladium alloy thin film formed on the substrate is used. On these substrates, another color filter layer, a resin layer, a transistor such as a TFT, a circuit, or the like may be formed.
  • the transparent substrate in the color filter of the present invention is not particularly limited as long as it is a base material transparent to visible light, and a transparent substrate used for a general color filter can be used.
  • transparent flexible rigid materials such as quartz glass, alkali-free glass, and synthetic quartz plates, or transparent flexible flexible materials such as transparent resin films, optical resin plates, and flexible glasses. Materials.
  • the thickness of the said transparent substrate is not specifically limited, According to the use of the color filter of this invention, the thing about 100 micrometers or more and 1 mm or less can be used, for example.
  • the color filter of the present invention includes, for example, an overcoat layer, a transparent electrode layer, an alignment film, an alignment protrusion, a columnar spacer, etc., in addition to the substrate, the light shielding portion, and the colored layer. Also good.
  • the display device includes the color filter according to the present invention.
  • the configuration of the display device is not particularly limited, and can be appropriately selected from conventionally known display devices, such as a liquid crystal display device and an organic light emitting display device.
  • display defects such as a liquid crystal orientation disorder caused by the electrical characteristics of the green pixel and a burn-in phenomenon caused by a switching threshold shift are suppressed.
  • the device is preferably selected.
  • the liquid crystal display device of the present invention includes the color filter according to the present invention described above, a counter substrate, and a liquid crystal layer formed between the color filter and the counter substrate.
  • a liquid crystal display device of the present invention will be described with reference to the drawings.
  • FIG. 2 is a schematic diagram illustrating an example of a display device of the present invention, and is a schematic diagram illustrating an example of a liquid crystal display device.
  • the liquid crystal display device 40 of the present invention includes a color filter 10, a counter substrate 20 having a TFT array substrate and the like, and a liquid crystal layer formed between the color filter 10 and the counter substrate 20. 30.
  • the liquid crystal display device of the present invention is not limited to the configuration shown in FIG. 2, but can be a configuration generally known as a liquid crystal display device using a color filter.
  • the driving method of the liquid crystal display device of the present invention is not particularly limited, and a driving method generally used for a liquid crystal display device can be employed. Examples of such a drive method include a TN method, an IPS method, an OCB method, and an MVA method. In the present invention, any of these methods can be preferably used. Further, the counter substrate can be appropriately selected and used according to the driving method of the liquid crystal display device of the present invention.
  • a method for forming a liquid crystal layer a method generally used as a method for producing a liquid crystal cell can be used, and examples thereof include a vacuum injection method and a liquid crystal dropping method.
  • FIG. 3 is a schematic diagram illustrating another example of the display device of the present invention, and is a schematic diagram illustrating an example of an organic light emitting display device.
  • the organic light emitting display device 100 of the present invention includes a color filter 10 and an organic light emitter 80.
  • An organic protective layer 50 and an inorganic oxide film 60 may be provided between the color filter 10 and the organic light emitter 80.
  • the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, and the cathode 76 are sequentially formed on the upper surface of the color filter. Examples thereof include a method and a method in which an organic light emitter 80 formed on another substrate is bonded onto the inorganic oxide film 60.
  • the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, the cathode 76, and other configurations in the organic light emitting body 80 known structures can be appropriately used.
  • the organic light emitting display device 100 manufactured as described above can be applied to, for example, a passive drive type organic EL display or an active drive type organic EL display.
  • the organic light emitting display device of the present invention is not limited to the configuration shown in FIG. 3, and may be a known configuration as an organic light emitting display device that generally uses a color filter.
  • the acid value of the block copolymer before salt formation was calculated
  • the amine value of the block copolymer before salt formation was determined by a method according to the method described in JIS K 7237.
  • the weight average molecular weight (Mw) of the block copolymer before salt formation was determined as a standard polystyrene equivalent value by GPC (gel permeation chromatography) according to the measurement method of the present invention described above.
  • the glass transition temperature (Tg) of the block copolymer before salt formation and after salt formation is determined by differential scanning calorimetry (DSC) (EXSTAR DSC 7020, manufactured by SII Nanotechnology Co., Ltd.) according to the method described in JIS K7121. It measured using.
  • DSC differential scanning calorimetry
  • EEMA 1-ethoxyethyl methacrylate
  • HEMA 2-hydroxyethyl methacrylate
  • EHMA 2-ethylhexyl methacrylate
  • MMA methyl methacrylate
  • the obtained block copolymer PGMEA solution is reprecipitated in hexane, purified by filtration and vacuum drying, and a structural unit derived from a block containing a structural unit represented by the general formula (I) and a carboxy group-containing monomer A block copolymer A-1 (acid value: 12 mgKOH / g, Tg: 44 ° C.) containing a B block having a solvophilic property was contained.
  • the block copolymer A-1 thus obtained was confirmed by GPC (gel permeation chromatography), and the weight average molecular weight Mw was 8100.
  • the amine value was 110 mgKOH / g.
  • 29.35 parts by mass of block copolymer A-1 was dissolved in 29.35 parts by mass of PGMEA in a 100 mL round bottom flask, and 1.59 parts by mass of phenylphosphonic acid (manufactured by Tokyo Chemical Industry) 0.1 mol) was added to 1 mol of the DMMA unit of the combined A-1, and the mixture was stirred at a reaction temperature of 30 ° C. for 20 hours to obtain a salt type block copolymer A-1 (dispersant a) solution.
  • the amine value after salt formation was calculated as follows.
  • the integrated value of the carbon atom peak adjacent to the non-salt-formed nitrogen atom and the carbon atom peak adjacent to the salt-formed nitrogen atom at the terminal nitrogen site (amino group) From the ratio, the ratio of the number of amino groups that are salt-formed to the total number of amino groups is calculated, and is not different from the theoretical salt-forming ratio (the two acidic groups of all phenylphosphonic acids are different from the DMMA of the block copolymer A-1). It was confirmed that a salt was formed with the terminal nitrogen site).
  • the amine value after salt formation was calculated as 88 mgKOH / g by subtracting the amine value (22 mgKOH / g) of 0.20 mol of DMMA unit from the amine value 110 mgKOH / g before salt formation.
  • the acid value of the block copolymer A-1 after salt formation is the same as that of the block copolymer A-1 before salt formation.
  • Table 1 shows the acid value, amine value, and Tg of the block copolymer A-1 before and after salt formation.
  • block copolymer A-5 The solvent was removed under reduced pressure to obtain block copolymer A-5.
  • the weight average molecular weight determined by GPC measurement (NMP LiBr 10 mM) was 8,350, and the amine value was 95 mgKOH / g.
  • NMP LiBr 10 mM The weight average molecular weight determined by GPC measurement (NMP LiBr 10 mM) was 8,350, and the amine value was 95 mgKOH / g.
  • 29.35 parts by mass of block copolymer A-5 was dissolved in 29.35 parts by mass of PGMEA, and 3.17 parts by mass of phenylphosphonic acid (PPA, manufactured by Tokyo Chemical Industry Co., Ltd.) 0.20 mol) is added to 1 mol of DMMA unit of copolymer A-5, and the mixture is stirred at a reaction temperature of 30 ° C.
  • Synthesis Example 6 Preparation of dispersant f
  • Synthesis Example 5 instead of phenylphosphonic acid, 3.80 parts by mass of benzyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (benzyl chloride is 0.3 mol with respect to 1 mol of DMMA unit of block copolymer A-5) is used.
  • a salt type block copolymer A-6 (dispersant f) solution was synthesized in the same manner as in Synthesis Example 5 except for the above.
  • Table 1 shows the acid value, amine value, and Tg of the obtained block copolymer before and after salt formation.
  • the obtained alkali-soluble resin A is a resin in which a side chain having an ethylenic double bond is introduced into the main chain formed by copolymerization of BzMA, MMA, and MAA using GMA, and has a solid content of 42.6 mass. %, Acid value 74 mgKOH / g, and weight average molecular weight 12000.
  • the weight average molecular weight was measured with a Shodex GPC System-21H (polypropylene) using polystyrene as a standard substance and THF as an eluent.
  • the acid value was measured based on JIS K 0070.
  • Synthesis Example 9 Preparation of alkali-soluble resin B solution
  • Synthesis Example 8 was used except that 20 parts by mass of styrene and 20 parts by mass of N-phenylmaleimide (Tokyo Chemical Industry Co., Ltd.) were used.
  • an alkali-soluble resin B solution was obtained.
  • the solid content was 42.6% by mass
  • the acid value was 74 mgKOH / g
  • the weight average molecular weight was 12,000.
  • the prepared polyaluminum chloride aqueous solution was added dropwise to the dye solution at 80 ° C. over 15 minutes, and further stirred at 80 ° C. for 1 hour.
  • the formed precipitate was collected by filtration and washed with water.
  • the obtained cake was dried to obtain 6.30 g (yield 96.2%) of a rhodamine acid dye metal lake color material (purple color material 2).
  • Example 1 (1) Production of Colorant Dispersion B1 6.23 parts by mass of Dispersant a Solution of Synthesis Example 1 as a dispersant and C.I. I. CI Pigment Blue 15: 6 (trade name FASTOGEN BLUE A510 manufactured by DIC Corporation) is 6.42 parts by mass, and C.I. I. Pigment Violet 23 (trade name: Hostaperm Violet RL-NF, manufactured by Clariant) 1.61 parts by mass, C.I. I.
  • CI Pigment Green 59 (PG59, trade name FASTOGEN GREEN C100 manufactured by DIC Corporation) 4.97 parts by mass, 14.59 parts by mass of the alkali-soluble resin A solution obtained in Synthesis Example 8, 66.12 parts by mass of PGMEA, Put 100 parts by mass of 2.0 mm zirconia beads into a mayonnaise bin, shake as a preliminary crushing with a paint shaker (manufactured by Asada Tekko Co., Ltd.) for 1 hour, then take out the 2.0 mm zirconia beads and remove the particles. 200 parts by mass of zirconia beads having a diameter of 0.1 mm was added, and similarly, this dispersion was dispersed for 4 hours with a paint shaker to obtain a colorant dispersion liquid B1.
  • PG59 trade name FASTOGEN GREEN C100 manufactured by DIC Corporation
  • the colored resin composition B1 obtained in (2) above is formed on a glass substrate (“NA35” manufactured by NH Techno Glass Co., Ltd.) having a thickness of 0.7 mm and a size of 100 mm ⁇ 100 mm. After applying using a spin coater, it is dried at 80 ° C. for 3 minutes using a hot plate, irradiated with 60 mJ / cm 2 of ultraviolet light using an ultrahigh pressure mercury lamp, and further post-baked for 30 minutes in a 230 ° C. clean oven. Thus, the colored layer B1 was formed by adjusting the film thickness so that the film thickness after curing was 2.50 ⁇ m.
  • Example 2 to 12 Comparative Examples 1 to 4
  • Example 2 to 6 Comparative Examples 1 to 4
  • the dispersion agent a solution
  • the same manner as in (1) of Example 1 except that the type and amount of dispersant were changed so that the solid content was the same part by mass, and the amount of PGMEA was adjusted so that the total amount was 100 parts by mass.
  • color material dispersions B2 to B6 and color material dispersion CB1 were obtained.
  • Example 7 to 9 the same procedure as (1) in Example 3 was performed except that the type and amount of color material were changed as shown in Table 2 in Example 1 (1).
  • Color material dispersions B7 to B9 were obtained.
  • the type and amount of the dispersant are equal to parts by mass with the same solid content.
  • the color material dispersion CB2 ⁇ CB4 was obtained.
  • Example 10 in the same manner as in Example 3 (2) except that 0.03 part by mass of the antioxidant IRGANOX 1010 (manufactured by BASF) was added in Example 3, for color filters.
  • a colored resin composition B10 was obtained.
  • Example 11 instead of using the alkali-soluble resin A solution in Example 3, the alkali-soluble resin B solution obtained in Synthesis Example 9 was used, and the antioxidant IRGANOX 1010 (manufactured by BASF) 0
  • a colored resin composition B11 for color filters was obtained in the same manner as (2) of Example 3 except that 0.03 parts by mass were added.
  • Example 12 as shown in Table 2 for the photoinitiator in Example 11, instead of 0.04 parts by mass of IRG369, an oxime ester photoinitiator (manufactured by Changzhou Strong Electronic New Materials, A colored resin composition B12 for color filters was obtained in the same manner as (2) of Example 11 except that 0.04 parts by mass of “TR-PBG-365” (PBG365) was used.
  • PBG365 TR-PBG-365
  • a colored resin composition could not be prepared.
  • Pigment Green 58 (trade name: FASTOGEN GREEN A110, manufactured by DIC Corporation)
  • Byk161 trade name Disperbyk-161 (by Big Chemie, urethane dispersant, solid content 30% by mass)
  • Byk2001 trade name Disperbyk-2001 (by Big Chemie, polymer having a structural unit represented by the general formula (I), solid content: 46% by mass)
  • Solvent A Propylene glycol monomethyl ether acetate (PGMEA)
  • Solvent B 3-methoxy-3-methyl-1-butyl acetate
  • Example 13 to 15 (1) Production of Color Material Dispersions B13 to B15 In Examples 13 to 15, the types and blending amounts of the color materials were changed as shown in Table 3 in Example 3 (1), and the total amount Color material dispersions B13 to B15 were obtained in the same manner as (1) of Example 3 except that the amount of PGMEA was adjusted to 100 parts by mass. (2) Production of Colored Resin Compositions for Color Filters B13 to B15 The above color material dispersions B13 to B15 are used in place of the color material dispersion B3 in (2) of Example 12, respectively.
  • PG36 C.I. I. Pigment Green 36 (trade name: FASTOGEN GREEN 2YK-50, manufactured by DIC Corporation)
  • PG7 C.I. I. Pigment Green 7 (trade name: Chromo Fine Green 6428EC, manufactured by Dainichi Seika Kogyo)
  • Example 16 to 33 (1) Production of Color Material Dispersions B16 to B33 In Examples 16 to 33, as shown in Table 4 in Example 3 (1), the types and blending amounts of the color materials were changed, and the total amount Color material dispersions B16 to B33 were obtained in the same manner as (1) of Example 3 except that the amount of PGMEA was adjusted to 100 parts by mass.
  • (2) Production of Colored Resin Compositions B16 to B33 for Color Filter The above color material dispersions B16 to B33 were used in place of the color material dispersion B3 in (2) of Example 12, respectively.
  • PB16 C.I. I. Pigment Blue 16 (Product name: Heliogen Blue D7490 manufactured by BASF)
  • Example 34 (1) Production of colorant dispersion 6.23 parts by mass of the dispersant c solution of Synthesis Example 3 as a dispersant and C.I. I. Pigment Blue 15: 6 (trade name FASTOGEN BLUE A510 manufactured by DIC Corporation) is 13.0 parts by mass, the alkali-soluble resin A solution obtained in Synthesis Example 8 is 14.59 parts by mass, and PGMEA is 66.20 parts by mass.
  • a purple color material dispersion v1 was obtained in the same manner as the blue color material dispersion b1 except that 13.0 parts by mass of Pigment Violet 23 (trade name: Hostaperm Violet RL-NF manufactured by Clariant) was used.
  • Pigment Violet 23 trade name: Hostaperm Violet RL-NF manufactured by Clariant
  • a green color material dispersion g1 was obtained in the same manner as the blue color material dispersion b1 except that 13.0 parts by mass of Pigment Green 59 (PG59, trade name FASTOGEN GREEN C100 DIC Corporation) was used.
  • Example 35 to 40 (1) Production of Colorant Dispersion B39 In Example 39, as shown in Table 5 in Example 1 (1), solid content was obtained by using Dispersant g solution instead of Dispersant a solution. Were changed to have the same mass part, and a colorant dispersion B39 was obtained in the same manner as (1) of Example 1 except that the amount of PGMEA was adjusted so that the total would be 100 parts by mass.
  • a colored resin composition B35 for color filter was obtained in the same manner as (2) of Example 3 except that 0.04 parts by mass of BASF) was used.
  • Example 36 instead of 0.03 part by mass of the antioxidant (trade name IRGANOX 1010 (1010), manufactured by BASF) in Example 10, the antioxidant (trade name ADK STAB AO-40 (AO- 40), manufactured by ADEKA) Except for using 0.03 parts by mass, a colored resin composition B36 for color filters was obtained in the same manner as (2) of Example 10.
  • Example 37 instead of 0.03 part by mass of the antioxidant (trade name IRGANOX 1010 (1010), manufactured by BASF) in Example 10, the latent antioxidant (Compound a) of Synthesis Example 12 was used.
  • a colored resin composition B37 for color filters was obtained in the same manner as (2) of Example 10 except that 0.03 parts by mass were used.
  • Example 38 instead of adding 0.03 part by mass of the antioxidant (trade name IRGANOX 1010 (1010), manufactured by BASF) in Example 10, an ultraviolet absorber (benzotriazole compound, trade name)
  • an ultraviolet absorber (benzotriazole compound, trade name)
  • a colored resin composition for color filter B38 was obtained in the same manner as (2) of Example 10 except that 0.03 part by mass of TINUVIN 329 BASF was added.
  • Example 39 a colored resin composition for a color filter was obtained in the same manner as in (2) of Example 3 except that the color material dispersion B39 was used instead of the color material dispersion B3 in Example 3. B39 was obtained.
  • Example 40 the alkali-soluble resin obtained in Synthesis Example 9 was used in Example 35, except that the color material dispersion B39 was used instead of the color material dispersion B3 and the alkali-soluble resin A solution was used.
  • solution B 0.03 parts by mass of antioxidant (trade name Adeka Stub AO-40 (AO-40), manufactured by ADEKA) and UV absorber (benzotriazole compound, product name: TINUVIN 329 BASF) 0.03
  • a colored resin composition B40 for a color filter was obtained in the same manner as (2) of Example 35 except for adding part by mass.
  • (3) Formation of colored layer In the same manner as (3) of Example 1 except that the colored resin compositions B35 to B40 were used instead of the colored resin composition B1 in (3) of Example 1. Thus, colored layers B35 to B40 were obtained.
  • Viscosity stability evaluation criteria A: Change rate of viscosity before and after storage is less than 10%
  • this is a value when the color material is 13% by mass with respect to the total mass including the solvent of the color material dispersion. Even if the evaluation result is C, the color material dispersion can be used practically. However, if the evaluation result is B, the color material dispersion is better. If the evaluation result is A, the color material dispersion is excellent in dispersion stability. Are better.
  • ⁇ Optical performance evaluation, contrast evaluation> The contrast, chromaticity (x, y), and luminance (Y) of the colored layers obtained in the examples and comparative examples were measured using a spectral characteristic measuring device LCF-1500M manufactured by Otsuka Electronics and a contrast measuring device CT-1B manufactured by Aisaka Electric. Measured. (Contrast evaluation criteria) -Value when C is light source and y is 0.038 to 0.070 AA: over 5000 A: 3500 to 4999 B: 1500-3499 C: less than 1500, value when y is 0.071 to 0.110 with C light source AA: over 6000 A: 4000 to 5999 B: 2000-3999 C: less than 2000.
  • the colored resin compositions for color filters obtained in the examples and comparative examples were respectively applied to a spin coater on a 100 mm ⁇ 100 mm glass substrate (“NA35” manufactured by NH Techno Glass Co., Ltd.) with a thickness of 0.7 mm. After being applied, it was dried at 60 ° C. for 3 minutes using a hot plate to form a colored layer having a thickness of 2.5 ⁇ m. The glass plate on which the colored layer was formed was shower-developed for 60 seconds using a 0.05% by mass aqueous potassium hydroxide solution as an alkaline developer.
  • the glass substrate After observing the unexposed portion (50 mm ⁇ 50 mm) of the glass substrate after the formation of the colored layer by visual observation, the glass substrate is thoroughly wiped with a lens cleaner (trade name Toraysee MK Clean Cloth, manufactured by Toray Industries, Inc.), The coloring degree of the lens cleaner was visually observed.
  • the above evaluation criteria are AA, A, B, or C, it can be used practically, but if the evaluation result is B, further A, and further AA, the effect is more excellent. ing.
  • ⁇ Development chip> Spin the colored resin composition for color filter obtained in each example and each comparative example on a 100 mm ⁇ 100 mm glass substrate (“NA35” manufactured by NH Techno Glass Co., Ltd.) with a thickness of 0.7 mm. After coating using a coater, the number of rotations is adjusted to the film thickness shown in the table after post baking (30 minutes in a 230 ° C clean oven) by drying at 60 ° C for 3 minutes using a hot plate. Then, a colored layer was formed. This colored layer was irradiated with 30 mJ / cm 2 of ultraviolet rays using a super high pressure mercury lamp through a photomask having a mask opening width of 80 ⁇ m and a mask light shielding width of 160 ⁇ m.
  • the glass plate on which the colored layer was formed was shower-developed for 100 seconds using a 0.05% by mass aqueous potassium hydroxide solution as an alkaline developer.
  • the developed substrate was observed with an optical microscope, and the number of chips on the edge portion of the colored layer in the range of 50 mm ⁇ 50 mm was measured.
  • ⁇ Mura> Spin the colored resin composition for color filter obtained in each example and each comparative example on a 100 mm ⁇ 100 mm glass substrate (“NA35” manufactured by NH Techno Glass Co., Ltd.) with a thickness of 0.7 mm. After coating using a coater, drying was performed at 60 ° C. for 3 minutes using a hot plate, thereby adjusting the number of revolutions so that the film thickness described in the table was obtained after post-baking to form a colored layer. The colored layer was irradiated with ultraviolet rays of 60 mJ / cm 2 using a super high pressure mercury lamp through a photomask having a mask opening width of 80 ⁇ m and a mask light shielding width of 160 ⁇ m.
  • the glass plate on which the colored layer was formed was shower-developed for 60 seconds using a 0.05% by mass aqueous potassium hydroxide solution as an alkaline developer.
  • the unevenness of the colored layer is visually observed under a projector on the substrate obtained by post-baking the colored substrate in a clean oven at 230 ° C. for 30 minutes, and the edge portion of the colored layer in the range of 50 mm ⁇ 50 mm is further observed with an optical microscope. The number of voids was measured.
  • the colorant dispersions of Comparative Examples 2 and 5 to 7 in which a conventional green color material is combined with a blue color material use a dispersant that is a polymer having a structural unit represented by the general formula (I).
  • a dispersant that is a polymer having a structural unit represented by the general formula (I).
  • the colored resin composition is a colored resin composition for a color filter that can form a colored layer with improved solvent resolubility and an expanded blue reproduction range. It has also been clarified that the colored layers using the photosensitive colored resin compositions of Examples 1 to 40 each suppress the occurrence of development chipping and unevenness.
  • Comparative Example 1 in which a blue color material, a purple color material, PG59, and a urethane-based dispersant are combined has a solvent re-solubility as compared with an example having the same chromaticity coordinates (x, y). Inferior, contrast, further development residue, development resistance, development chipping and unevenness were inferior.
  • a urethane-based dispersant is combined with the color material combination, the dispersibility and dispersion stability are poor, so the color material is not well surrounded by the dispersant and is adsorbed by the re-dissolvable solvent. It is presumed that the coloring material is hardly washed away.
  • the average in the range of 280 nm to 360 nm The transmittance is 42% or more).
  • the average transmittance in the range of 280 nm to 360 nm was less than 41%.
  • Example 10 in Example 36 using a hindered phenol antioxidant having a molecular weight of 500 or less and a molecular weight per phenolic hydroxyl group of 200 equivalents or less, a colored layer having high contrast was obtained. Further, in Example 37 using the latent antioxidant, a colored resin composition with improved unevenness suppression effect was obtained, and a colored layer with good development adhesion and improved contrast was obtained.
  • Example 38 in which the oxime ester photoinitiator and the ultraviolet absorber were combined, a colored resin composition with improved development chipping and unevenness suppression effect was obtained.
  • the ultraviolet absorber was added, a colored layer with improved contrast was obtained.
  • an alkali-soluble resin containing both a maleimide structure having a hydrocarbon ring and a styrene structure is used, and an oxime ester photoinitiator having a carbazole skeleton and an oxime ester photoinitiator having diphenyl sulfide are used in combination.
  • Example 40 using a combination of a hindered phenolic antioxidant having a molecular weight of 500 or less and a molecular weight per phenolic hydroxyl group of 200 equivalents or less and an ultraviolet absorber, A colored resin composition with improved unevenness suppression and development resistance was obtained, and a colored layer with improved contrast was obtained.

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Abstract

L'invention fournit une composition de résine colorée pour filtre coloré dont les propriétés de nouvelle dissolution dans un solvant sont améliorées, et qui permet de former une couche colorée présentant une zone de reproduction du bleu élargie. Cette composition de résine colorée pour filtre coloré comprend un matériau coloré, un agent de dispersion, un composant liant et un solvant. Ledit matériau coloré contient un matériau coloré bleu, un matériau coloré violet et un pigment vert C.I.59. Ledit agent de dispersion consiste en un polymère possédant une unité constitutive spécifique.
PCT/JP2018/000470 2017-01-17 2018-01-11 Liquide de dispersion de matière colorée pour filtre coloré, composition de résine colorée pour filtre coloré, filtre coloré, et dispositif d'affichage Ceased WO2018135370A1 (fr)

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JP2018541447A JP6494875B2 (ja) 2017-01-17 2018-01-11 カラーフィルタ用色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタ、及び表示装置

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JP2019095558A (ja) * 2017-11-21 2019-06-20 サカタインクス株式会社 カラーフィルター用青色顔料分散組成物
WO2020071437A1 (fr) * 2018-10-03 2020-04-09 日立化成デュポンマイクロシステムズ株式会社 Composition de résine photosensible, procédé de fabrication de produit durci à motifs, produit durci, film isolant intercouche, couche de revêtement de couverture, film de protection de surface et composant électronique
KR20200114448A (ko) * 2019-03-28 2020-10-07 동우 화인켐 주식회사 착색 감광성 수지 조성물, 이를 이용하여 제조된 블랙 매트릭스 및/또는 컬럼 스페이서를 포함하는 컬러필터 및 컬러필터를 포함하는 화상표시장치
KR20200124000A (ko) * 2019-04-23 2020-11-02 인하대학교 산학협력단 온도감응성 고분자 박막을 갖는 광공진기를 포함하는 컬러 필터
JPWO2020241389A1 (fr) * 2019-05-24 2020-12-03
JP2021096360A (ja) * 2019-12-17 2021-06-24 東洋インキＳｃホールディングス株式会社 感光性着色組成物、カラーフィルタ、および液晶表示装置
WO2022215652A1 (fr) * 2021-04-05 2022-10-13 株式会社日本触媒 Copolymère contenant un groupe amino
WO2022270357A1 (fr) * 2021-06-25 2022-12-29 株式会社Ｄｎｐファインケミカル Composition de résine colorée photosensible, produit durci, filtre coloré et dispositif d'affichage
US20230130507A1 (en) * 2020-03-31 2023-04-27 Sumitomo Chemical Company, Limited Negative resist composition
JP2023090171A (ja) * 2021-12-17 2023-06-29 東洋インキＳｃホールディングス株式会社 青色カラーフィルタ用感光性着色組成物、カラーフィルタ、およびそれを用いた固体撮像素子並びに液晶表示装置
WO2023210543A1 (fr) * 2022-04-27 2023-11-02 株式会社日本触媒 Copolymère contenant un groupe amino

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