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WO2020045197A1 - Composition de pigment, composition colorante et filtre coloré - Google Patents

Composition de pigment, composition colorante et filtre coloré Download PDF

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Publication number
WO2020045197A1
WO2020045197A1 PCT/JP2019/032696 JP2019032696W WO2020045197A1 WO 2020045197 A1 WO2020045197 A1 WO 2020045197A1 JP 2019032696 W JP2019032696 W JP 2019032696W WO 2020045197 A1 WO2020045197 A1 WO 2020045197A1
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Prior art keywords
group
substituent
optionally
independently
optionally substituted
Prior art date
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PCT/JP2019/032696
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English (en)
Japanese (ja)
Inventor
龍矢 重廣
近藤　仁
竜史 山崎
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Priority to JP2019569859A priority Critical patent/JP6705571B1/ja
Publication of WO2020045197A1 publication Critical patent/WO2020045197A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B25/00—Quinophthalones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a pigment composition, a coloring composition, and a color filter.
  • coloring compositions are used in various fields. Specific uses of the coloring compositions include printing inks, paints, coloring agents for resins, coloring agents for fibers, coloring materials for IT information recording (color filters). , Toner, and inkjet). Dyes used in the coloring composition are required to have color characteristics (coloring power, sharpness), resistance (weather resistance, light resistance, heat resistance, solvent resistance) and the like. Dyes are mainly classified into pigments and dyes, but pigments are different from dyes that develop color in a molecular state, and develop color in a particle state (aggregates of primary particles). For this reason, pigments are generally superior to dyes in terms of resistance, but are inferior in coloring power and chroma (clearness).
  • Patent Document 1 discloses that a green coloring composition containing a predetermined quinophthalone compound and an aluminum phthalocyanine pigment provides excellent coloring power and dispersibility, as well as high brightness and a high contrast ratio when used in a color filter. It is disclosed.
  • pigments intended for color filters are required to have different properties from those for general-purpose applications. Specifically, for example, “high brightness” for reducing the power consumption of the backlight, “high coloring power” for thinning the color filters and high color reproduction, and the like are required.
  • the coloring composition disclosed in Patent Literature 1 does not always provide sufficient luminance and coloring power when a color filter is used. That is, the coloring composition disclosed in Patent Literature 1 has room for further improvement in terms of increasing luminance and obtaining high color reproducibility even in a thin film.
  • an object of the present invention is to provide a pigment composition and a coloring composition having excellent luminance and coloring power, and a color filter using the same.
  • the present inventors have conducted intensive studies to solve the above problems, and as a result, have found that by combining a compound having a dimerized quinophthalone skeleton and a compound having an aluminum phthalocyanine skeleton, luminance and coloring power are improved. .
  • One aspect of the present invention is a quinophthalone compound represented by the following formula (1), at least one compound selected from the group consisting of a compound represented by the following formula (2A) and a compound represented by the following formula (2B). And an aluminum phthalocyanine compound.
  • X 1 to X 16 are each independently a hydrogen atom or a halogen atom
  • Y 1 and Y 2 are each independently a hydrogen atom or a halogen atom
  • Z is an alkylene group having 1 to 3 carbon atoms. It is.
  • X 51 to X 54 each independently have an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent
  • a heterocyclic group an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted alkylthio group, or an optionally substituted substituent.
  • An arylthio group, Y 51 to Y 54 are each independently a halogen atom, a nitro group, a phthalimidomethyl group optionally having a substituent, or a sulfamoyl group optionally having a substituent
  • L 1 is a hydroxyl group, a chlorine atom
  • —OP ( O) R 1 R 2 or —O—SiR 3 R 4 R 5
  • R 1 to R 5 are each independently a hydrogen atom, a hydroxyl group
  • R 1 and R 2 may combine with each other to form a ring
  • two of R 3 , R 4, and R 5 may combine with each other to form a ring
  • m1 to m4 and n1 to n4 are each independently an integer of 0 to 4,
  • X 55 to X 62 each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, a cycloalkyl group optionally having a substituent, or a substituent
  • a heterocyclic group an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted alkylthio group, or an optionally substituted substituent.
  • An arylthio group, Y 55 to Y 62 are each independently a halogen atom, a nitro group, a phthalimidomethyl group optionally having a substituent, or a sulfamoyl group optionally having a substituent
  • R 12 —O— R 6 to R 12 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group optionally having a substituent, an aryl group optionally having a substituent, an alkoxy group optionally having a substituent, or Aryloxy group which may have a substituent
  • m5 to m12 and n5 to n12 are each independently an integer of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m
  • Another aspect of the present invention provides at least one selected from the group consisting of a quinophthalone compound represented by the above formula (1), a compound represented by the above formula (2A), and a compound represented by the above formula (2B).
  • This is a coloring composition containing a kind of aluminum phthalocyanine compound and a solvent.
  • Another aspect of the present invention provides at least one selected from the group consisting of a quinophthalone compound represented by the above formula (1), a compound represented by the above formula (2A), and a compound represented by the above formula (2B).
  • the present invention it is possible to provide a pigment composition and a coloring composition excellent in luminance and coloring power, and a color filter using them.
  • the pigment composition according to one embodiment contains a quinophthalone compound and an aluminum phthalocyanine compound.
  • the quinophthalone compound is represented by the following formula (1).
  • X 1 to X 16 are each independently a hydrogen atom or a halogen atom
  • Y 1 and Y 2 are each independently a hydrogen atom or a halogen atom
  • Z is an alkylene group having 1 to 3 carbon atoms. It is.
  • the quinophthalone compound exhibits selective absorption and transmission due to dimerization of the quinophthalone skeleton.
  • the quinophthalone skeleton is dimerized using the linking group Z as a spacer, whereby conjugation is cut off and excessive redness is suppressed.
  • dispersibility is improved by introducing an imide structure.
  • the pigment composed of the quinophthalone compound when the pigment composed of the quinophthalone compound is combined with a pigment composed of an aluminum phthalocyanine compound, the pigment composed of the predetermined quinophthalone compound described in Patent Document 1 described above is used. It shows a better luminance and an excellent coloring power exceeding this.
  • the halogen atom in the formula (1) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a chlorine atom.
  • alkylene group having 1 to 3 carbon atoms in the formula (1) include, for example, a methylene group, an ethylene group (1,1-ethanediyl group or 1,2-ethanediyl group), a propylene group (1,1-ethanediyl group).
  • a methylene group a 1,1-ethanediyl group, a 1,1-propanediyl group, , 2-propanediyl group is more preferred, and methylene group is even more preferred.
  • At least one of X 1 to X 16 is preferably a halogen atom, and more preferably two or more are halogen atoms.
  • a halogen atom is introduced into X 1 to X 16 , the dispersibility of the quinophthalone compound is further improved, and the above effects tend to be more remarkably obtained.
  • At least one of X 1 to X 4 is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms.
  • Preferably at least one of X 2 and X 3 is a halogen atom, more preferably X 2 and X 3 are each a halogen atom.
  • At least one of X 5 to X 8 is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. It is preferred that at least one is a halogen atom of X 6 and X 7, and more preferably X 6 and X 7 are each a halogen atom.
  • At least one of X 9 to X 12 is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. It is preferred that at least one is a halogen atom of X 10 and X 11, and more preferably X 10 and X 11 are each a halogen atom.
  • At least one of X 13 to X 16 is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. It is preferred that at least one is a halogen atom of X 14 and X 15, and more preferably X 14 and X 15 are each a halogen atom.
  • Y 1 and Y 2 may be the same or different, but are preferably the same from the viewpoint of facilitating the synthesis of the quinophthalone compound.
  • quinophthalone compound ⁇ Specific examples of the quinophthalone compound are described below, but the quinophthalone compound is not limited thereto.
  • the above quinophthalone compounds may be used alone or in a combination of two or more.
  • the method for producing the quinophthalone compound is not particularly limited, and the quinophthalone compound can be produced by appropriately utilizing a conventionally known method.
  • a method for producing a quinophthalone compound will be described, but the production method is not limited thereto.
  • the quinophthalone compound can be obtained, for example, by a method including the following Step I, Step II, Step III and Step IV.
  • Examples of the strong acid include hydrochloric acid, sulfuric acid, nitric acid and the like.
  • Examples of the oxidizing agent include sodium iodide, p-chloranil, nitrobenzene, and the like.
  • the reaction temperature may be from 80 ° C to 100 ° C, preferably from 90 ° C to 100 ° C, and the reaction time may be from 1 hour to 6 hours, preferably from 3 hours to 6 hours.
  • the compound of the formula (A-2) can be obtained by reacting the obtained compound of the formula (A-1) with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid.
  • Y 1 , Y 2 and Z are as described above.
  • the reaction temperature may be -20 ° C to 70 ° C, preferably 0 ° C to 50 ° C, and the reaction time may be 1 hour to 4 hours, preferably 1 hour to 3 hours.
  • the compound of the formula (A-3) can be obtained by adding 6 to 8 equivalents of reduced iron to 1 equivalent of the obtained compound of the formula (A-2) and reacting.
  • Y 1 , Y 2 and Z are as described above.
  • the reaction temperature may be from 60 ° C to 80 ° C, preferably from 70 ° C to 80 ° C, and the reaction time may be from 1 hour to 3 hours, preferably from 2 hours to 3 hours.
  • Step IV> at least one selected from the group consisting of phthalic anhydride and halogen-substituted phthalic anhydride is used per equivalent of the compound of the formula (A-3) obtained by the method described in JP-A-2013-61622.
  • an acid catalyst examples include benzoic acid and zinc chloride.
  • the reaction temperature may be 180 ° C. to 250 ° C., preferably 210 ° C. to 250 ° C.
  • the reaction time may be 1 hour to 8 hours, preferably 3 hours to 8 hours.
  • the aluminum phthalocyanine compound is at least one selected from the group consisting of a compound represented by the following formula (2A) and a compound represented by the following formula (2B).
  • X 51 to X 54 each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a cycloalkyl group optionally having a substituent.
  • a heterocyclic group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent Is an arylthio group which may have
  • the “substituent” in each of these groups includes a halogen atom, an amino group, a hydroxyl group, a nitro group and the like.
  • alkyl group of the alkyl group which may have a substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, Examples thereof include a linear or branched alkyl group such as an n-octyl group, a stearyl group, and a 2-ethylhexyl group.
  • alkyl group having a substituent examples include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2,2,3,3-tetrafluoropropyl Group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2 , 4-dichlorobenzyl group and the like.
  • Examples of the“ aryl group ”of the optionally substituted aryl group include a phenyl group, a naphthyl group, an anthryl group and the like.
  • “Aryl group having a substituent” includes p-methylphenyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-amino Phenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthra And a quinonyl group.
  • Examples of the “cycloalkyl group” of the optionally substituted cycloalkyl group include a cyclopentyl group, a cyclohexyl group, and an adamantyl group.
  • Examples of the “substituted cycloalkyl group” include a 2,5-dimethylcyclopentyl group, a 4-tert-butylcyclohexyl group, and the like.
  • heterocyclic group having a substituent examples include a 3-methylpyridyl group, an N-methylpiperidyl group, an N-methylpyrrolyl group, and the like.
  • alkoxy group of the alkoxy group which may have a substituent includes a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, Linear or branched alkoxy groups such as 2,3-dimethyl-3-pentyloxy group, n-hexyloxy group, n-octyloxy group, stearyloxy group and 2-ethylhexyloxy group.
  • Examples of the “substituted alkoxy group” include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2-ditrifluoro group.
  • Examples include a methylpropoxy group, a 2-ethoxyethoxy group, a 2-butoxyethoxy group, a 2-nitropropoxy group, and a benzyloxy group.
  • Examples of the“ aryloxy group ”of the optionally substituted aryloxy group include a phenoxy group, a naphthoxy group and an anthryloxy group.
  • the “aryloxy group having a substituent” includes p-methylphenoxy, p-nitrophenoxy, p-methoxyphenoxy, 2,4-dichlorophenoxy, pentafluorophenoxy, 2-methyl-4-chloro Phenoxy groups and the like.
  • Examples of the ⁇ alkylthio group '' of the alkylthio group which may have a substituent include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a decylthio group, a dodecylthio group, and an octadecylthio group.
  • alkylthio group having a substituent examples include a methoxyethylthio group, an aminoethylthio group, a benzylaminoethylthio group, a methylcarbonylaminoethylthio group, a phenylcarbonylaminoethylthio group, and the like.
  • arylthio group having a substituent examples include a chlorophenylthio group, a trifluoromethylphenylthio group, a cyanophenylthio group, a nitrophenylthio group, a 2-aminophenylthio group, a 2-hydroxyphenylthio group, and the like.
  • Y 51 to Y 54 each independently represent a halogen atom, a nitro group, a phthalimidomethyl group optionally having a substituent (C 6 H 4 (CO) 2 N—CH 2 —), Or a sulfamoyl group (H 2 NSO 2 —) which may have a substituent.
  • the phthalimidomethyl group having a substituent is a group in which a hydrogen atom in the phthalimidomethyl group is substituted by a substituent.
  • a sulfamoyl group having a substituent is a group in which a hydrogen atom in a sulfamoyl group is substituted by a substituent.
  • the “substituent” in each of these groups is the same as the substituent described for X 51 to X 54 .
  • Y 51 to Y 54 are preferably a halogen atom.
  • the halogen atom is selected from a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom or a bromine atom, and more preferably a bromine atom.
  • R 1 to R 5 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or An aryloxy group which may have a substituent.
  • R 1 and R 2 may combine with each other to form a ring, and two of R 3 , R 4, and R 5 may combine with each other to form a ring.
  • Examples of the alkyl group for R 1 to R 5 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, an n-octyl group, and a stearyl group. And a straight-chain or branched alkyl group such as 2-ethylhexyl group.
  • alkyl group having a substituent in R 1 to R 5 examples include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2-ethoxyethyl group, -Butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group and the like.
  • Examples of the aryl group for R 1 to R 5 include a phenyl group, a naphthyl group, an anthryl group and the like.
  • Examples of the aryl group having a substituent for R 1 to R 5 include a p-tolyl group, a p-bromophenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a 2,4-dichlorophenyl group, a pentafluorophenyl group, 2-dimethylaminophenyl group, 2-methyl-4-chlorophenyl group, 4-methoxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, etc. Is mentioned.
  • Examples of the alkoxy group for R 1 to R 5 include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group and a 2,3-dimethyl-3- Examples thereof include a linear or branched alkoxy group such as a pentyloxy group, an n-hexyloxy group, an n-octyloxy group, a stearyloxy group, and a 2-ethylhexyloxy group.
  • alkoxy group having a substituent in R 1 and R 2 examples include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, Examples thereof include a 2,2-ditrifluoromethylpropoxy group, a 2-ethoxyethoxy group, a 2-butoxyethoxy group, a 2-nitropropoxy group, and a benzyloxy group.
  • Examples of the aryloxy group for R 1 to R 5 include a phenoxy group, a naphthyloxy group, an anthryloxy group and the like.
  • the aryloxy group having a substituent represented by R 1 to R 5 includes p-methylphenoxy, p-nitrophenoxy, p-methoxyphenoxy, 2,4-dichlorophenoxy, pentafluorophenoxy, 2-methyl -4-chlorophenoxy group and the like.
  • R 1 and R 2 are each independently preferably an aryl group optionally having a substituent or an aryloxy group optionally having a substituent, and more preferably an aryl group or an aryloxy group. And more preferably a phenyl group or a phenoxy group.
  • Both R 1 and R 2 are preferably an aryl group which may have a substituent or an aryloxy group which may have a substituent, and both R 1 and R 2 are an aryl group or an aryloxy group. It is more preferable that both R 1 and R 2 are a phenyl group or a phenoxy group.
  • m1 to m4 and n1 to n4 are each independently an integer of 0 to 4, and m1 + n1, m2 + n2, m3 + n3, and m4 + n4 are each independently an integer of 0 to 4.
  • the sum of m1 to m4 may be, for example, 5 or more, 7 or more, or 9 or more, and may be 15 or less, 13 or less, or 11 or less.
  • all of m1 to m4 may be 0. It is preferable that all of n1 to n4 are 0.
  • X 55 to X 62 each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a cycloalkyl group optionally having a substituent.
  • a heterocyclic group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent Is an arylthio group which may have
  • the “substituent” in each of these groups is the same as the substituent described for X 51 to X 54 . Specific examples of these groups are the same as the specific examples of each group described for X 51 to X 54 .
  • each of Y 55 to Y 62 independently represents a halogen atom, a nitro group, a phthalimidomethyl group which may have a substituent (C 6 H 4 (CO) 2 N—CH 2 —), Or a sulfamoyl group (H 2 NSO 2 —) which may have a substituent.
  • the “substituent” in each of these groups is the same as the substituent described for X 51 to X 54 .
  • Specific examples of these groups are the same as the specific examples of each group described for Y 51 to Y 54 .
  • R 6 to R 12 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group optionally having a substituent, an aryl group optionally having a substituent, an alkoxy group optionally having a substituent, or An aryloxy group which may have a substituent.
  • Specific examples of each group in R 6 to R 12 are the same as the specific examples of each group described for R 1 to R 5 .
  • m5 to m12 and n5 to n12 are each independently an integer of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m8 + n8, m9 + n9, m10 + n10, m11 + n11, and m12 + n12 are each independently 0 to 4 It is an integer.
  • the sum of m5 to m12 may be, for example, 9 or more, 14 or more, or 19 or more, and may be 31 or less, 26 or less, or 21 or less.
  • all of m5 to m12 may be 0. It is preferable that all of n5 to n12 are 0.
  • the above quinophthalone compound can exhibit properties as an organic pigment.
  • the quinophthalone compound may be compounded as a pigment.
  • the above-mentioned aluminum phthalocyanine compound can exhibit properties as an organic pigment, and may be compounded as a pigment.
  • Examples of such aluminum phthalocyanine pigments include C.I. I. Pigment Green 63. That is, the pigment composition according to the present embodiment may contain a pigment composed of the quinophthalone compound (quinophthalone pigment) and a pigment composed of the aluminum phthalocyanine compound (aluminum phthalocyanine pigment).
  • Each of the quinophthalone compound and the aluminum phthalocyanine compound may be formed into a pigment by a known and commonly used method.
  • Each of the quinophthalone pigment and the aluminum phthalocyanine pigment may be finely divided by, for example, a salt milling treatment, or may be subjected to a surface treatment such as a rosin treatment, a surfactant treatment, a solvent treatment, and a resin treatment.
  • the content ratio of the quinophthalone compound (quinophthalone pigment) to the aluminum phthalocyanine compound (aluminum phthalocyanine pigment) in the pigment composition is appropriately determined according to the type of the aluminum phthalocyanine compound and the desired color tone (chromaticity).
  • the content of the quinophthalone compound (quinophthalone pigment) may be, for example, not less than 1 part by mass and 95 parts by mass with respect to 100 parts by mass of the total amount of the quinophthalone compound (quinophthalone pigment) and the aluminum phthalocyanine compound (aluminum phthalocyanine pigment).
  • it is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and preferably 90 parts by mass. Or less, more preferably 85 parts by mass or less.
  • the pigment composition may further contain components other than those described above.
  • the pigment composition may further contain an organic pigment, an organic dye, an organic pigment derivative and the like other than the above.
  • organic pigments include, for example, azo pigments, disazo pigments, azomethine pigments, anthraquinone pigments, quinophthalone pigments other than the above quinophthalone pigments, quinacridone pigments, diketopyrrolopyrrole pigments, dioxazine pigments And benzimidazolone pigments, phthalocyanine pigments other than the above-mentioned aluminum phthalocyanine pigments, isoindoline pigments, isoindolinone pigments, perylene pigments and the like.
  • the organic pigment is preferably an azo pigment, an azomethine pigment, a quinophthalone pigment other than the quinophthalone pigment, a phthalocyanine pigment other than the aluminum phthalocyanine pigment, an isoindoline pigment, and the like.
  • organic dyes examples include xanthene dyes, azo dyes, disazo dyes, anlaquinone dyes, quinophthalone dyes, triarylmethane dyes, methine dyes, phthalocyanine dyes, and rhodamine dyes.
  • the organic dye is preferably a phthalocyanine dye.
  • the organic pigment derivative may be, for example, a derivative in which a part of a known organic pigment is modified (substituted) with a sulfonic acid group, a carboxyl group, an amino group, a phthalimidomethyl group, or the like.
  • a sulfonic acid group for example, Solsperse (registered trademark) 5000, 12000 and 22000 (manufactured by Lubrizol Co., Ltd.) and the like can be mentioned.
  • the content of the organic pigment derivative may be 1 part by mass or more and 20 parts by mass or less based on 100 parts by mass of the total amount of the pigment.
  • the pigment composition may further contain a resin such as a photosensitive resin and a curable resin, rosin, a surfactant, a dispersant, and the like. These components may or may not be treated (so-called surface treatment) on the pigment surface.
  • Methods for treating the pigment surface include dissolving these components in a solvent and then depositing them on the pigment surface, adding these components in a kneader and kneading them together with the pigment, A known method such as a method of adsorbing components may be used.
  • the pigment composition may be in the form of a powder. By dispersing the pigment composition in a solvent, a colored composition that is a pigment dispersion can be formed.
  • the coloring composition contains the above quinophthalone compound, the above aluminum phthalocyanine compound, and a solvent.
  • the embodiments of the quinophthalone compound and the aluminum phthalocyanine compound in the coloring composition and the ratio thereof may be the same as the embodiments of the quinophthalone compound and the aluminum phthalocyanine compound in the pigment composition described above and the ratio thereof, respectively.
  • the solvent is preferably an organic solvent.
  • organic solvent include aromatic solvents such as toluene, xylene, and methoxybenzene; ethyl acetate, butyl acetate; acetate solvents such as propylene glycol monomethyl ether acetate; propylene glycol monoethyl ether acetate; and ethoxyethyl propionate.
  • Propionate solvents alcohol solvents such as methanol and ethanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and fats such as hexane Group hydrocarbon solvents, N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone, aniline Emissions, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as ⁇ - butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate acid.
  • ether solvents such as butyl cellosolve
  • propylene glycol monomethyl ether diethylene glycol ethyl ether
  • the organic solvent is preferably a solvent that is polar and soluble in water, more preferably a propionate-based solvent, an alcohol-based solvent, an ether-based solvent, a ketone-based solvent, a nitrogen compound-based solvent, or a lactone-based solvent. is there.
  • the content of the solvent is 300 parts by mass or more based on 100 parts by mass of the total amount of the quinophthalone compound (quinophthalone pigment) and the aluminum phthalocyanine compound (aluminum phthalocyanine pigment) (hereinafter referred to as “total amount of pigment”). It may be less than 2000 parts by mass.
  • the coloring composition may further contain a dispersant and / or an organic pigment derivative from the viewpoint of suitably dispersing the quinophthalone pigment and the aluminum phthalocyanine pigment in a solvent.
  • dispersing agent examples include ANTI-TERRA (registered trademark) U / U100, 204, DISPERBYK (registered trademark) 106, 108, 109, 112, 130, 140, 142, 145, 161, 162, 163, 164, 167, 168, 180, 182, 183, 184, 185, 2000, 2001, 2008, 2009, 2013, 2022 2025, 2026, 2050, 2055, 2150, 2155, 2163, 2164, 9076, 9077, BYK @ LPN-6919, 21116, 21324, 22102 (manufactured by Big Chemie Co., Ltd.) , EFKA (registered trademark) 46, 47, 4010, 4020, 4320, 43 0, 4330, 4401, 4570, 5054, 7461, 7462, 7476, 7777 (manufactured by BASF), Azispar (registered trademark) PB814, 821, 822, 881 (Ajinomoto Fine
  • the coloring composition may further contain a photosensitive resin.
  • a coloring composition containing a photosensitive resin can also be referred to as a photosensitive coloring composition.
  • the photosensitive resin include thermoplastic resins such as urethane resin, acrylic resin, polyamic acid resin, polyimide resin, styrene maleic acid resin, styrene maleic anhydride resin, and 1,6-hexanediol.
  • Bifunctional monomers such as diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, etc., trimethylolpropane triacrylate, Such as pentaerythritol triacrylate, tris- (2-acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, etc.
  • Examples include photopolymerizable monomers such as functional monomers.
  • the photosensitive coloring composition may further contain a photopolymerization initiator.
  • a photopolymerization initiator include acetophenone, benzophenone, benzyldimethylketanol, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, and 1,3-bis (4 ′).
  • the coloring composition contains a photosensitive resin (further, a photopolymerization initiator)
  • the coloring composition is obtained, for example, by the following method. First, a quinophthalone pigment and an aluminum phthalocyanine pigment are dispersed in a solvent, if necessary, together with a dispersant and / or an organic pigment derivative to obtain a dispersion. Next, a photosensitive resin (further, a photopolymerization initiator) is added to the dispersion, a solvent is further added as necessary, and the mixture is uniformly stirred to obtain a coloring composition.
  • a photosensitive resin further, a photopolymerization initiator
  • the content of the photosensitive resin may be not less than 3 parts by mass and not more than 25 parts by mass with respect to 100 parts by mass of the dispersion.
  • the content of the photopolymerization initiator may be 0.05 parts by mass or more and 3 parts by mass or less based on 1 part by mass of the photosensitive resin.
  • the yellow pigment preferably absorbs light in a wider wavelength range in a blue region where light is not absorbed (transmitted) by the blue pigment or green pigment used in combination.
  • the amount of light absorbed in the blue region by the yellow pigment has been increased by increasing the content of the yellow pigment.
  • problems such as a decrease in luminance and an increase in film thickness.
  • the compound represented by the formula (1) since the compound represented by the formula (1) has a structure in which the quinophthalone skeleton is dimerized, the quinophthalone pigment spreads to a longer wavelength side in the blue region as compared with the conventional yellow pigment. It has an absorption spectrum. Therefore, it is possible to achieve a high color reproduction greenness without increasing the content of the quinophthalone pigment. Therefore, with this green color filter, high luminance can be achieved while realizing high color reproducibility even with a thin film.
  • the coloring composition is suitable as a coloring composition for a color filter (used for forming a color filter), and particularly suitable as a coloring composition used for forming a green color filter (a green pixel portion of a color filter). is there.
  • a color filter having a pixel portion formed from the coloring composition.
  • a color filter according to one embodiment has a pixel portion containing the above quinophthalone compound and the above aluminum phthalocyanine compound.
  • the pixel section is preferably a green pixel section.
  • the pixel portion can be easily formed from the above-described coloring composition (photosensitive coloring composition).
  • a coloring composition photosensitive coloring composition
  • a method for example, a coloring composition (photosensitive coloring composition) is applied on a transparent substrate such as glass by a spin coating method, a roll coating method, an ink jet method, or the like, and then the coating film is applied.
  • a method called photolithography in which after performing pattern exposure with ultraviolet rays through a photomask, an unexposed portion is washed with a solvent or the like to obtain a colored pattern.
  • the method for forming the pixel portion is not particularly limited.
  • a pattern of the pixel portion may be formed by an electrodeposition method, a transfer method, a micellar electrolysis method, or a PVED (Photovoltaic Electrodeposition) method to manufacture a color filter. .
  • the above quinophthalone compound and aluminum phthalocyanine compound are included in one composition, but in another embodiment, the above quinophthalone compound and aluminum phthalocyanine compound May be contained in separate compositions, respectively. That is, another embodiment of the present invention relates to a first pigment composition (coloring composition) containing the above quinophthalone compound and a second pigment composition (coloring composition) containing the above aluminum phthalocyanine compound. ) And a pigment composition set (colored composition set).
  • This pigment composition set (coloring composition set) is also suitably used for forming a color filter, and is particularly suitably used for forming a green color filter (a green pixel portion of a color filter).
  • the temperature was lowered to 80 ° C., and 15.3 g (112 mmol) of zinc chloride was added little by little. Then, 200 ml of THF was added, and the mixture was stirred for 1 hour while maintaining the temperature at 80 ° C. After allowing to cool to room temperature, ocher powder was recovered by vacuum filtration. The obtained ocher powder was washed with 200 ml of THF, and the ocher powder was recovered by vacuum filtration again. Further, the obtained ocher powder was transferred to a flask, 200 ml of water and 40 ml of 28% aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. The powder was recovered by vacuum filtration to obtain 20.3 g of a crude product.
  • the solid was collected, dried by blowing air at 70 ° C., added to a mixed solvent of 100 ml of dimethyl sulfoxide (DMSO) and 100 ml of N, N-dimethylformamide (DMF), and stirred at 90 ° C. for 1 hour.
  • DMSO dimethyl sulfoxide
  • DMF N, N-dimethylformamide
  • the mixture was filtered under reduced pressure on Celite, and the obtained filtrate was added to 1 L of water while stirring.
  • the resulting precipitate was collected by filtration under reduced pressure, and washed with water to obtain 3.80 g (11.6 mmol) of intermediate (9) (yield:> 99%).
  • the average aspect ratio is calculated from the average value of the longer diameter (major axis) and the shorter diameter (minor axis) of 40 primary particles constituting the aggregate on the secondary image, and the average value of the major axis is calculated as the average primary particle. Diameter. The average aspect ratio was less than 3.00. The average primary particle size was 100 nm or less.
  • Pigmentation Example 2 Pigmentation was carried out in the same manner as in Pigmentation Example 1, except that the quinophthalone dimer (10) obtained in Synthesis Example 2 was used instead of the quinophthalone dimer (7) obtained in Synthesis Example 1. Thus, a quinophthalone pigment was obtained.
  • the average aspect ratio of the obtained pigment particles was less than 3.00, and the average primary particle size was 100 nm or less.
  • Pigmentation Example 3 Pigmentation was carried out in the same manner as in Pigmentation Example 1, except that the quinophthalone monomer (15) obtained in Synthesis Example 4 was used instead of the quinophthalone dimer (7) obtained in Synthesis Example 1. Performed to obtain a quinophthalone pigment.
  • the average aspect ratio of the obtained pigment particles was less than 3.00, and the average primary particle size was 100 nm or less.
  • Example 2 A colored composition was obtained in the same manner as in Example 1, except that the yellow toning composition obtained in Production Example 2 was used instead of the yellow toning composition obtained in Production Example 1. .
  • Each of the obtained coloring compositions is applied on a glass substrate by a spin coater, dried, and heated at 230 ° C. for 1 hour to produce an evaluation sample showing a predetermined green chromaticity when a C light source is used. did.
  • the green chromaticity the green chromaticity (0.260, 0.650) in the color standard for high color reproduction used in JP-A-2010-2550 was used.
  • the chromaticity is a value measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation).
  • the luminance Y in the obtained evaluation sample was measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation).
  • the thickness of the colored film formed on the glass substrate was measured by a film thickness meter (VS1330 scanning white interference microscope manufactured by Hitachi High-Tech Science Corporation). It can be said that the thinner the film thickness, the higher the coloring power. Table 1 shows the results.
  • Example 3 The composition for green toning obtained in Production Example 4 was used instead of the composition for blue toning obtained in Production Example 3, and the ratio of quinophthalone pigment: aluminum phthalocyanine pigment (mass ratio) was 27:73.
  • a colored composition was obtained in the same manner as in Example 1, except that a yellow toning composition and a blue toning composition were mixed.
  • Example 4 A colored composition was obtained in the same manner as in Example 3, except that the yellow toning composition obtained in Production Example 2 was used instead of the yellow toning composition obtained in Production Example 1. .
  • a colored composition was obtained in the same manner as in Example 3, except that the composition for yellow toning and the composition for blue toning were mixed.

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

Abstract

Un aspect de la présente invention concerne une composition de pigment contenant : un composé de quinophtalone représenté par la formule (1) ; et au moins un composé de phtalocyanine d'aluminium choisi dans le groupe constitué de composés représentés par la formule (2A) et de composés similaires. X1 à X16 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène et Y1 et Y2 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène et Z représente un groupe alkylène contenant 1 à 3 atomes de carbone. X51 à X54 représentent un groupe alkyle et des groupes similaires, qui peuvent porter un substituant, Y51 à Y54 représentent un atome d'halogène et des groupes similaires, L1 représente un groupe hydroxyle et des groupes similaires, et m1-m4 et n1 à n4 sont des nombres entiers de 0 à 4.
PCT/JP2019/032696 2018-08-31 2019-08-21 Composition de pigment, composition colorante et filtre coloré Ceased WO2020045197A1 (fr)

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WO2022054612A1 (fr) * 2020-09-08 2022-03-17 住友化学株式会社 Composition de résine colorée
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2023234094A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément photodétecteur, capteur d'image et procédé de fabrication d'élément photodétecteur
WO2023234096A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de détection de lumière, capteur d'image et procédé de production d'élément de détection de lumière
WO2023234095A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de photodétection, capteur d'image et procédé de fabrication d'élément de photodétection

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WO2013098836A1 (fr) * 2011-10-24 2013-07-04 Keki Hormusji Gharda Pigmentcomprenant la bis-quinophtalone et son procédé de préparation
WO2018159372A1 (fr) * 2017-03-01 2018-09-07 Dic株式会社 Composé de quinophtalone

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JP5114905B2 (ja) * 2006-09-22 2013-01-09 東洋インキＳｃホールディングス株式会社 顔料、顔料組成物及び顔料分散体
JP5572986B2 (ja) * 2008-08-29 2014-08-20 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色剤、それを用いたカラーフィルタ用着色組成物、及びカラーフィルタ

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JP2012247587A (ja) * 2011-05-27 2012-12-13 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用着色組成物、およびカラーフィルタ
WO2013098836A1 (fr) * 2011-10-24 2013-07-04 Keki Hormusji Gharda Pigmentcomprenant la bis-quinophtalone et son procédé de préparation
WO2018159372A1 (fr) * 2017-03-01 2018-09-07 Dic株式会社 Composé de quinophtalone

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022054612A1 (fr) * 2020-09-08 2022-03-17 住友化学株式会社 Composition de résine colorée
JPWO2022054612A1 (fr) * 2020-09-08 2022-03-17
CN116018382A (zh) * 2020-09-08 2023-04-25 住友化学株式会社 着色树脂组合物
EP4212592A4 (fr) * 2020-09-08 2024-12-25 Sumitomo Chemical Company, Limited Composition de résine colorée
CN116018382B (zh) * 2020-09-08 2025-01-07 住友化学株式会社 着色树脂组合物
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2023234094A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément photodétecteur, capteur d'image et procédé de fabrication d'élément photodétecteur
WO2023234096A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de détection de lumière, capteur d'image et procédé de production d'élément de détection de lumière
WO2023234095A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de photodétection, capteur d'image et procédé de fabrication d'élément de photodétection

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