Photosensitive coloring composition, color filter, and image display device

Abstract

To provide a photosensitive coloring composition which suppresses a water stain of a film after development, and has good residual film rate and pattern shape.SOLUTION: A photosensitive coloring composition contains a photopolymerization initiator (A) represented by the following formula, a binder resin (B), a photopolymerizable compound (C), and a coloring agent (D). The binder resin (B) preferably contains an alkali-soluble resin having a carboxy group and a polymerizable unsaturated group in a side chain which can be obtained by reaction of an epoxy group and a carboxy group.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal display device, a solid-state imaging device, an organic EL display device, a quantum dot display device, and The present invention relates to a photosensitive coloring composition used in the production of color filters for electronic paper and the like. [Background technology]

[0002] Color filters are films made by applying a photosensitive coloring composition onto a transparent substrate such as glass. By photolithography, the filter segments of each color and the black matrix are It is produced by forming a pattern. When the coating is exposed to light and then developed using an alkaline developer, the pattern (coating) There was a problem of discoloration (hereafter referred to as water stains).

[0003] Therefore, Patent Document 1 discloses a photosensitive resin containing a resin-type surfactant having a fluorinated alkyl group. Patent Document 2 discloses a coloring composition. The polyalkylene oxide chain has a side chain having a polymerizable unsaturated group at the end thereof. A photosensitive coloring composition containing a resin is disclosed. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-164965 [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-65865 Summary of the Invention [Problem to be solved by the invention]

[0005] However, conventional photosensitive coloring compositions have been insufficient in suppressing water stains and have difficulty forming good-shaped prints. There was a problem that it was difficult to obtain a turn. Also, the film thickness of the pattern was significantly reduced after post-baking (residual film There were also problems with the rate.

[0006] The present invention suppresses water stains on the coating after development, and produces a good remaining film rate and a good shaped pattern. The present invention aims to provide a photosensitive coloring composition that can be formed. [Means for solving the problem]

[0007] The photosensitive coloring composition of the present invention comprises a photopolymerization initiator (A) represented by the following general formula (1), The composition contains an under resin (B), a photopolymerizable compound (C), and a colorant (D).

[0008] General formula (1) [ka]

[0009] (In the formula, R1 and R2 each independently represent R 11 or COR 11 represents R 11 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R 11 The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may have a branched side chain or may be a cyclic alkyl, R3 represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, and the alkyl portion of the alkyl group, aryl group, arylalkyl group, or heterocyclic group represented by R3 may have a branched side chain or may be a cyclic alkyl, and the hydrogen atom of the aryl group, arylalkyl group, or heterocyclic group represented by R3 may be further 21 , OR21 , C.O.R. 21 , S.R. 21 , N.R. 22 R 23 ,CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , N.R. 22 COR 21 ,OCOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , hydroxyl group, nitro group, CN, halogen atom, or COOR 21 may be substituted with R 21 , R 22 and R 23 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R 21 , R 22 and R 23 The hydrogen atoms of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group, and R 21 , R 22 and R 23 The alkyl group, aryl group, arylalkyl group, or alkylene portion of the heterocyclic group represented by the formula: 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 The oxygen atoms may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-, provided that they are not adjacent to each other; R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R 24The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may have a branched side chain or may be a cyclic alkyl, R4 is hydrogen atoms, represents a hydroxyl group, CN, a nitro group, or a halogen atom, and n represents 0 or 1. [Effects of the Invention]

[0010] According to the present invention, water stains on the coating after development are suppressed, the remaining film rate is good, and the shape is good. A photosensitive coloring composition capable of forming a pattern, a color filter, and an image display device can be provided. Cut. [Brief explanation of the drawings]

[0011] [Figure 1] FIG. 1 is a schematic cross-sectional view of a liquid crystal display device. DETAILED DESCRIPTION OF THE INVENTION

[0012] The terms used in this specification are defined as follows: "(meth)acryloyl", "(meth)acrylic", "( (Meth)acrylic acid," "(meth)acrylate," or "(meth)acrylamide" In these cases, unless otherwise specified, the terms "acryloyl and / or methacryloyl" and "methacryloyl" are used. "acrylic and / or methacrylic acid", "acrylic acid and / or methacrylic acid", "Acrylate and / or methacrylate" or "acrylamide and / or methacrylate" "CI" stands for Color Index (CI). The polymerizable unsaturated groups include vinyl groups and (meth)polymers. The monomer contains an acryloyl group and is a polymerizable unsaturated group-containing monomer.

[0013] The photosensitive coloring composition of the present invention comprises a photopolymerization initiator (A) represented by the following general formula (1), The photosensitive resin of the present invention contains a binder resin (B), a photopolymerizable compound (C), and a colorant (D). The photosensitive coloring composition can be applied to a substrate to form a coating film. By using a photolithography method, a pattern of a desired shape can be formed. It is preferable to cure the coating film formed from the photosensitive coloring composition of the present invention by coating. It is preferable to use it for the filter segments that make up the color filter and the black matrix. It's nice. The photosensitive coloring composition of the present invention contains a photopolymerization initiator (A) represented by the following general formula (1): The improved photocurability of the composition surprisingly prevents water spots on the coating. Efficient photo-curing allows for good film retention and formation of well-shaped patterns. can.

[0014] <Photopolymerization initiator (A)> The photosensitive coloring composition contains a photopolymerization initiator (A) represented by general formula (1).

[0015] General formula (1) [ka]

[0016] (In the formula, R1 and R2 each independently represent R 11 or COR 11 represents R 11 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R 11 The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may have a branched side chain or may be a cyclic alkyl, R3 represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, and the alkyl portion of the alkyl group, aryl group, arylalkyl group, or heterocyclic group represented by R3 may have a branched side chain or may be a cyclic alkyl, and the hydrogen atom of the aryl group, arylalkyl group, or heterocyclic group represented by R3 may be further 21 , OR 21 , C.O.R. 21 , S.R. 21 , N.R. 22 R 23 ,CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , N.R. 22 COR 21 ,OCOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , hydroxyl group, nitro group, CN, halogen atom, or COOR 21 may be substituted with R 21 , R 22 and R 23 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R 21 , R 22 and R 23 The hydrogen atoms of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group, and R 21 , R 22 and R 23 The alkyl group, aryl group, arylalkyl group, or alkylene portion of the heterocyclic group represented by the formula: 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR24 The oxygen atoms may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-, provided that they are not adjacent to each other; R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R 24 The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may have a branched side chain or may be a cyclic alkyl, R4 is hydrogen atoms, represents a hydroxyl group, CN, a nitro group, or a halogen atom, and n represents 0 or 1.

[0017] In the above general formula (1), R3, R 11 , R 21 , R 22 , R 23 and R 24 is expressed as Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, and isopropyl. , butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl, xyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl Isononyl, Decyl, Isodecyl, Undecyl, Dodecyl, Tetradecyl, Hexadecanol Cyl, octadecyl, icosyl, cyclopentyl, cyclopentylmethyl, cyclopentyl ethyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl, etc. do.

[0018] In the above general formula (1), R3, R 11 , R 21 , R 22 , R 23 and R 24 is expressed as Examples of the aryl group having 6 to 30 carbon atoms include phenyl, tolyl, xylyl, and ethylphenyl. phenyl, naphthyl, anthryl, phenanthrenyl, and alkyl groups substituted with one or more of the above alkyl groups Examples thereof include phenyl, biphenylyl, naphthyl, and anthryl.

[0019] In the above general formula (1), R3, R 11 , R 21 , R 22 , R 23 and R 24 is expressed as Examples of the arylalkyl group having 7 to 30 carbon atoms include benzyl, α-methylbenzyl, Examples include α,α-dimethylbenzyl, phenylethyl, and the like.

[0020] In the above general formula (1), R3, R 11 , R 21 , R 22 , R 23 and R 24 is expressed as Examples of the heterocyclic group having 2 to 20 carbon atoms include pyridyl, pyrimidyl, furyl, thienyl, Tetrahydrofuryl, dioxolanyl, benzoxazol-2-yl, tetrahydro Imidazolidyl, pyrazolidyl, thiazolidyl, isothiazolidyl oxazolidyl, isoxazolidyl, piperidyl, piperazyl, morpholinyl, etc. Examples of the heterocyclic ring include 5- to 7-membered heterocyclic rings.

[0021] The photopolymerization initiator (A) represented by the above general formula (1) can be, for example, the following compounds Nos. 1 to N: o.8. However, the present invention is not limited to the following compounds.

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] The photopolymerization initiator (A) represented by general formula (1) (hereinafter referred to as photopolymerization initiator (A)) is High sensitivity, particularly high residual film rate, and suppression of water stains after development. In this way, a photosensitive coloring composition capable of forming a color filter of good quality can be obtained. The photosensitive coloring composition containing the polymerization initiator has excellent heat resistance, pattern shape, development resistance, and chemical resistance. High quality filter segments and black matrices can be formed.

[0026] The content of the photopolymerization initiator (A) is 1 to 100 parts by mass relative to 100 parts by mass of the colorant (D). If the amount is less than 100 parts by mass, it is difficult to form a pattern. When the amount is 1 part by mass or more, water spots can be suppressed more effectively. do.

[0027] <Other photopolymerization initiators (Y)> The photosensitive coloring composition contains a photopolymerization initiator (A) and another photopolymerization initiator (Y) in combination. This allows for better pattern formation.

[0028] Other examples of the photopolymerization initiator (Y) include 4-phenoxydichloroacetophenone, 4- t-Butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropyl (2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl)- 2-methyl-1-[4-(methylthio)phenyl]-2-methyl-hexyl phenyl ketone Morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholino )phenyl]-2-(phenylmethyl)-1-butanone, or 2-(dimethylamino)- 2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]- Acetophenone compounds such as 1-butanone; benzoin, benzoin methyl ether, benzoin methyl ether, Benzoin ethyl ether, benzoin isopropyl ether, or benzyl dimethyl ether Benzoin compounds such as benzoyl benzoates; benzophenone, benzoyl benzoic acid, benzoyl benzoin Methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone phenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3',4, Benzophenones such as 4'-tetra(t-butylperoxycarbonyl)benzophenone Compounds: Thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isothioxanthone Propylthioxanthone, 2,4-diisopropylthioxanthone, or 2,4-diethylthioxanthone Thioxanthone compounds such as thioxanthone; 2,4,6-trichloro-s-triazinone; 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methyl)-4,6-bis(trichloromethyl)-s-triazine (p-tolylphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6 -Bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6 -Styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl) 2-(4-methoxy-naphth-1-yl)-4,6-bis(triazinyl) (trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6- Triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine Triazine compounds such as 1,2-octanedione, 1-[4-(phenylthio)furan] phenyl-, 2-(O-benzoyloxime)], or ethanone, 1-[9-ethyl-6- (2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetylbenzoyl) Oxime ester compounds such as bis(2,4,6-trimethylbenzoyl) fluoride; Phenylphosphine oxide, or diphenyl-2,4,6-trimethylbenzoylphosphine Phosphine compounds such as phenoxide; 9,10-phenanthrenequinone, camphor Quinone compounds such as quinone and ethylanthraquinone; borate compounds; carbazole imidazole-based compounds; or titanocene-based compounds. Among these, acetophenone compounds, phosphine compounds, imidazole compounds and and oxime ester compounds. Of these, oxime ester compounds are more preferred.

[0029] The content of the other photopolymerization initiator (Y) is 0.5 to 100 parts by mass of the colorant (D). The amount is preferably 200 parts by mass, and more preferably 1 to 100 parts by mass. The content of other photopolymerization initiator (Y) is based on 100 parts by mass of photopolymerization initiator (A). The content is preferably 1 to 3,000 parts by mass, and more preferably 5 to 2,000 parts by mass. This further improves the pattern shape.

[0030] The photopolymerization initiators can be used alone or in combination of two or more.

[0031] <Sensitizer (E)> The photosensitive coloring composition can contain a sensitizer (E). The content of the sensitizer (E) is determined by the photopolymerization initiator. The amount is preferably 1 to 200 parts by mass relative to 100 parts by mass of the initiator (A).

[0032] The sensitizer (E) is, for example, an unsaturated hydroxyl group represented by chalcone derivatives and dibenzalacetone. Ketones, 1,2-diketone derivatives such as benzil and camphorquinone, benzo quinone derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives Thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin Derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives Polymethine dyes such as acridine derivatives, azine derivatives, thiazine derivatives, oxazine Derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives compounds, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives compounds, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine anine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalylporphyrazine derivatives Conductors, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyridin Lilium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spiro Oxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, Among these, thioxanthone derivatives, Michler's ketone derivatives, etc. Ketone derivatives and carbazole derivatives are preferred. Specifically, 2,4-diethylthioxane thioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropyl Isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythio Xanthone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diphenyl) 4,4'-bis(ethylmethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzo yl-N-ethylcarbazole and the like.

[0033] The sensitizer (E) can be used alone or in combination of two or more kinds.

[0034] <Binder resin (B)> When a coating film having a thickness of 2 μm is formed, the binder resin (B) has a total area of ​​400 to 700 nm. The resin has a transmittance of 80% or more in the wavelength range. The transmittance is preferably 95% or more. The binder resin (B) is preferably an alkali-soluble resin. The coating formed from the photosensitive coloring composition can be patterned by photolithography. The binder resin (B) may have a thermosetting group. The thermosetting group may be, for example, For example, an epoxy group, an oxetanyl group, etc. may be mentioned.

[0035] <Alkali-soluble resin> The alkali-soluble resin may be any known resin, and may be selected from the following (I) and (II): an alkali-soluble resin having a carboxyl group and a polymerizable unsaturated group in a side chain selected from the group consisting of This is preferable, as it improves the photo-curing properties of the coating. (I) Reaction product of epoxy groups in a polymer having epoxy groups with a carboxyl group-containing monomer The alkali-soluble resin (hereinafter referred to as "alkali") is obtained by reacting a polybasic acid or a polybasic acid anhydride with the This is called soluble resin (I). (II) Reaction of a carboxy group in a polymer having a carboxy group with an epoxy group-containing monomer The reactant is an alkali-soluble resin (hereinafter referred to as alkali-soluble resin (II)).

[0036] [Alkali-soluble resin (I)] First, a polymer of an epoxy group-containing monomer and other monomers is synthesized. Monocarboxyl group-containing monomers are added to the epoxy groups of the polymer, and the resulting hydroxyl groups are reacted with polycarboxyl groups. A method of obtaining an alkali-soluble photosensitive resin by reacting a basic acid anhydride is also exemplified. The monocarboxyl group-containing monomer is a monomer having one carboxyl group.

[0037] [Alkali-soluble resin (II)] First, a polymer of a carboxyl group-containing monomer and other monomers is synthesized. Add an epoxy group-containing monomer to the carboxy group of the polymer in an amount less than the carboxy group. One method is to

[0038] Examples of the epoxy group-containing monomer include glycidyl (meth)acrylate and methyl glycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxy Epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate Among these, glycidyl (meth)acrylate is the most popular from the viewpoint of reactivity. is preferred

[0039] Monocarboxyl group-containing monomers include, for example, (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, (meth)acrylic acid α-position haloalkyl, alkoxyl, halo Examples include monocarboxylic acids such as halogen, nitro, and cyano substituted monocarboxylic acids.

[0040] Examples of polybasic acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, Aromatic and alicyclic acid anhydrides such as phthalic anhydride; fatty acids such as succinic anhydride and maleic anhydride Acid anhydrides, phosphoric acid anhydrides, sulfonic acid anhydrides. It may have a carboxyl group that does not form an acid anhydride.

[0041] Other monomers include, for example, methyl (meth)acrylate and ethyl (meth)acrylate. , n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (Meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate , stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofuran Furyl (meth)acrylate, isobornyl (meth)acrylate, phenyl (meth)acrylate Acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, Phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol ethoxy polyethylene glycol (meth)acrylate, or ethoxy polyethylene glycol (meth)acrylate (Meth)acrylates such as Alternatively, (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N -Diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, Dia (Meth)acrylamides such as acetone (meth)acrylamide or acryloylmorpholine Styrene, α-methylstyrene, ethyl vinyl ether, n-propanol propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or Vinyl ethers such as isobutyl vinyl ether, vinyl acetate, or vinyl propionate and the like.

[0042] Also, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide Imide, 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 3-maleimido Dopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimidocoumarin, 4 ,4'-Bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimide) (midophenyl)methane, N,N'-1,3-phenylenedimaleimide, N,N'-1,4 -phenylenedimaleimide, N-(1-pyrenyl)maleimide, N-(2,4,6-triphenyl)maleimide N-(4-chlorophenyl)maleimide, N-(4-aminophenyl)maleimide, N-(4-nitrophenyl)maleimide (triphenyl)maleimide, N-benzylmaleimide, N-bromomethyl-2,3-dichloro N-succinimidyl-3-maleimidobenzoate, N-succinimidyl N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate N-succinimidyl-6-maleimidohexanoate, N-[4-(2-benzoyl) N-substituted maleimides such as [(midazolyl)phenyl]maleimide and 9-maleimidoacridine EO modified cresol acrylate, n-nonylphenoxy polyethylene glycol Acrylate, Phenoxyethyl Acrylate, Ethoxylated Phenyl Acrylate, Phenoxy Ethylene oxide (EO) modified (meth)acrylate of paracumylphenol EO or propylene oxide (PO) modified (meth)acrylate, nonylphenol EO modified (meth)acrylate, PO modified (meth)acrylate of nonylphenol, etc. Examples include:

[0043] [Other alkali-soluble resins] The binder resin (B) is a mixture of an alkali-soluble resin (I) and an alkali-soluble resin (II). In addition to the above, an alkali-soluble resin having a polymerizable unsaturated group in the side chain can be contained. For example, a hydroxyl group-containing monomer, a carboxyl group-containing monomer, and other monomers are polymerized. Then, a polymer is prepared by adding an isocyanate group-containing monomer to the hydroxyl group of the polymer. An example of such a method is to synthesize an alkali-soluble photosensitive resin by reacting an isocyanate group.

[0044] The hydroxyl group-containing monomer is, for example, 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2- or 3- or 4-hydroxypropyl hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, or cyclohexyl Hydroxyalkyl methacrylates such as hexanedimethanol mono(meth)acrylate In addition, hydroxyalkyl (meth)acrylates and ethylene oxides are also suitable. Polyethers obtained by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide, etc. Mono(meth)acrylate, polyγ-valerolactone, polyε-caprolactone, and Polyester mono(meth)acrylic acid and / or poly(12-hydroxystearic acid) Among these, 2-hydroxyethyl methacrylate, glycerin, Glycerol mono(meth)acrylate is preferred, and glycerol mono(meth)acrylate is preferred. More preferable.

[0045] The isocyanate group-containing monomer is, for example, 2-(meth)acryloylethyl isocyanate. acrylate, 2-(meth)acryloyloxyethyl isocyanate, or 1,1-bis[meth acryloyloxy]ethyl isocyanate, and the like.

[0046] The other monomers include, in addition to the other monomers exemplified above, phosphate ester group-containing monomers, etc. The phosphate ester group-containing monomer may be, for example, a hydroxyl group-containing monomer having the following structure attached to the hydroxyl group: It is a compound that is reacted with a phosphate esterifying agent such as phosphorus pentoxide or polyphosphoric acid.

[0047] The raw materials for the alkali-soluble resin can be used alone or in combination of two or more kinds.

[0048] The alkali-soluble resin having no photosensitivity is, for example, an acrylic resin having an acidic group, an α- Olefin / maleic anhydride copolymer, styrene / styrene sulfonic acid copolymer, olefin Styrene / (meth)acrylic acid copolymer, or isobutylene / (maleic anhydride) copolymer Among these, those having an acidic group are preferred in terms of improving developability, heat resistance, and transparency. Acrylic resin and styrene / styrene sulfonic acid copolymer are preferred. A thermoplastic resin that is not soluble in water can be used in combination.

[0049] The binder resin (B) can be used alone or in combination of two or more kinds.

[0050] The content of the binder resin (B) is 1 to 400 parts by mass relative to 100 parts by mass of the colorant (D). The amount is preferably 1 to 300 parts by mass, and more preferably 1 to 300 parts by mass.

[0051] <Photopolymerizable compound (C)> The photopolymerizable compound (C) is a compound having a polymerizable unsaturated group. ) is a monomer and oligomer that hardens when exposed to ultraviolet light or heat to produce a transparent resin. The photopolymerizable compound (C) includes an acid group-containing polymerizable compound and a urethane bond-containing polymerizable compound. and other polymerizable compounds.

[0052] (Acid group-containing polymerizable compound) The acid group of the acid group-containing polymerizable compound may be, for example, a sulfonic acid group, a carboxyl group, a phosphoric acid group, etc. Examples include: The acid group-containing polymerizable compound is, for example, a free hydroxyl group of a polyhydric alcohol and (meth)acrylic acid. Esterification products of group-containing poly(meth)acrylates and dicarboxylic acids; polycarboxylic acids Examples include esters of acids and monohydroxyalkyl (meth)acrylates. Specific examples include trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, acrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate Dipentaerythritol pentaacrylate, Dipentaerythritol pentamethacrylate Monohydroxy oligoacrylates such as methacrylate or monohydroxy oligomethacrylates Free carbonyl compounds of esters and dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, and phthalic acid Carboxyl group-containing monoesters; Propane-1,2,3-tricarboxylic acid (tricarboxylic acid Valicic acid), butane-1,2,4-tricarboxylic acid, benzene-1,2,3-tricarbo carboxylic acid, benzene-1,3,4-tricarboxylic acid, benzene-1,3,5-tricarboxylic acid Tricarboxylic acids such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methyl acrylate, acrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate Monohydroxymonoacrylates or monohydroxymonomethacrylates such as acrylates and free carboxyl group-containing oligoesters of the above.

[0053] (Urethane bond-containing polymerizable compound) The urethane bond-containing polymerizable compound contains a urethane bond. The compound is, for example, a compound obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate. Polyfunctional urethane acrylate obtained by reacting alcohol with polyfunctional isocyanate and then reacted with a (meth)acrylate having a hydroxyl group to form a multifunctional urethane acrylate. Examples include tethers.

[0054] (Meth)acrylates with hydroxyl groups are 2-hydroxyethyl (meth)acrylates , 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate Acrylate, Pentaerythritol tri(meth)acrylate, Ditrimethylolpropane Tri(meth)acrylate, Dipentaerythritol Penta(meth)acrylate, Dipentaerythritol Pentaerythritol ethylene oxide modified penta(meth)acrylate, dipentaerythritol Thuritol propylene oxide modified penta(meth)acrylate, dipentaerythritol Caprolactone modified penta(meth)acrylate, glycerol acrylate methacrylate Acrylate, Glycerol Dimethacrylate, 2-Hydroxy-3-Acryloylpropyl Methacrylate, reaction product of epoxy group-containing compound and carboxy(meth)acrylate, water Examples thereof include acid group-containing polyol polyacrylates.

[0055] Polyfunctional isocyanates include tolylene diisocyanate and hexamethylene diisocyanate. Diphenylmethylene diisocyanate, isophorone diisocyanate, polyisocyanate Nate and others.

[0056] Other polymerizable compounds include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate Acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate Acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol Triethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene Pyrene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexa Ethylene glycol (meth)acrylate, trimethylolpropane PO modified tri(meth)acrylate ) acrylate, trimethylolpropane EO modified tri(meth)acrylate, isocyanate Nuric acid EO modified di(meth)acrylate, isocyanuric acid EO modified tri(meth)acrylate acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol Pentaerythritol tetra(meth)acrylate, 1,6- Hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglyceride Glycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether Dipentaerythritol di(meth)acrylate, Dipentaerythritol hexa(meth)acrylate, Dipentaerythritol Pentaerythritol penta(meth)acrylate, tricyclodecanyl(meth)acrylate esters of methylol melamine (meth)acrylates, epoxy (meth)acrylates acrylates, urethane acrylates, and various acrylic and methacrylic esters, Meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene Glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylic acid acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, Examples include acrylonitrile.

[0057] The photopolymerizable compound (C) can be used alone or in combination of two or more kinds.

[0058] The content of the photopolymerizable compound (C) is 5 to 300 parts by mass relative to 100 parts by mass of the colorant (D). The amount is preferably 10 to 200 parts by mass, and more preferably 10 to 200 parts by mass.

[0059] Mass of photopolymerization initiator (A) [I a ] to the mass [M] of the photopolymerizable compound (C) [ I a / M) is preferably from 0.01 to 3.00, more preferably from 0.15 to 2.00. In addition, when the photosensitive coloring composition contains a sensitizer (E) or other photopolymerization initiator (Y), The total mass of the photopolymerization initiator (A), the sensitizer (E), and other photopolymerization initiators (Y) (I b ) The mass ratio [I b / M) is 0.01 to 3.00 It is preferable that the mass ratio is 0.15 to 2.00, and more preferable that the mass ratio is 0.15 to 2.00. a / M] This allows for better balance of improvements in development resistance, chemical resistance, pattern shape, linearity, and resolution.

[0060] <Colorant (D)> The colorant (D) may be an organic or inorganic pigment. The pigment has high color development and durability. A pigment with high heat resistance is preferred, and an organic pigment is usually preferred. A dye may be contained within a range that does not decrease the

[0061] Specific examples of organic pigments are shown below by color index numbers. Red pigments include, for example, CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 4 7, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50 :1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 5 7:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 8 1, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101 :1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123 , 144, 146, 147, 149, 151, 166, 168, 169, 170, 172 , 173, 174, 175, 176, 177, 178, 179, 181, 184, 185 , 187, 188, 190, 193, 194, 200, 202, 206, 207, 208 , 209, 210, 214, 216, 220, 221, 224, 230, 231, 232 , 233, 235, 236, 237, 238, 239, 242, 243, 245, 247 , 249, 250, 251, 253, 254, 255, 256, 257, 258, 259 , 260, 262, 263, 264, 265, 266, 267, 268, 269, 270 , 271, 272, 273, 274, 275, 276, 277, 278, 279, 280 , 281, 282, 283, 284, 285, 286, 287, 291, 295, 296 , pigments described in JP 2014-134712 A, and pigments described in JP 6368844 A Among these, the heat resistance and light resistance of the filter segment are From the viewpoint of transmittance, CI Pigment Red 48:1, 122, 17 7, 224, 242, 269, 254, 291, 295, 296, JP 2014-134 712 and the pigments described in Japanese Patent No. 6368844. More preferably, CI Pigment Red 177, 254, 291, 295, 296, especially Pigments described in Patent Publication No. 2014-134712 and Patent Publication No. 6368844 It is a pigment that has been

[0062] Red pigments include CI Pigment Orange 36, 38, 43, 51, 55, 59, Orange pigments or yellow pigments such as 61, 71, or 73 may also be used in combination.

[0063] Blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, and 15:1. , 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 2 9, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 6 7, 68, 71, 72, 73, 74, 75, 76, 78, 79, etc. Among these, from the viewpoint of heat resistance, light resistance, and transmittance of the filter segment, C. I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6 More preferably, it is CI Pigment Blue 15:6. Also, a purple pigment may be used in combination. can.

[0064] Purple pigments include, for example, CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3 :1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50, etc. From the viewpoint of heat resistance, light resistance, and transmittance of the filter segment, CI pigment is preferable. CI Pigment Violet 19 or 23, more preferably CI Pigment Violet No. 23.

[0065] Green pigments include, for example, CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 1 4, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55 , 58, 59, 62, 63, and the pigments described in JP-A-2017-111398. Among these, CI Pigment Green 36, 58, and 5 Pigments described in JP-A-2017-111398 and JP-A-2017-111398 are preferred.

[0066] Yellow pigments include, for example, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 1 2, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, 233 and the pigments described in JP-A-2012-226110. CI Pigment Yellow 138, 139, 150, 185, 231, 233, JP This is a pigment described in Publication No. 2012-226110.

[0067] Cyan coloring compositions include, for example, CI Pigment Blue 15:1, 15:2, 15: Examples of blue pigments include blue pigments such as 15:4, 15:3, 15:6, 16, and 81.

[0068] Magenta coloring compositions include, for example, CI Pigment Violet 1, 19, CI Examples of the pigments include purple pigments and red pigments such as Pigment Red 144, 146, 177, 169, and 81. The magenta composition can be used in combination with a yellow pigment.

[0069] Examples of inorganic pigments include titanium oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, Bengara (red iron (III) oxide), cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green , umber, synthetic iron black, etc.

[0070] The black photosensitive coloring composition for forming the black matrix is, for example, a carbon black. Contains lac, aniline black, anthraquinone-based black pigments, and perylene-based black pigments Specifically, CI Pigment Black 1, 6, 7, 12, 20, and 31 are preferred. The black photosensitive coloring composition may contain a red pigment, a blue pigment, and a green pigment. Among these, carbon black is preferred in terms of its low cost and light-shielding properties. Carbon black may be surface treated with resin or the like. Therefore, a blue pigment or a purple pigment can be used in combination with the black photosensitive coloring composition.

[0071] The dyes include, for example, acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, and disperse dyes. Examples include reactive dyes, mordant dyes, vat dyes, and sulfur dyes. Lake pigments obtained by lake-forming dyes are also included.

[0072] The dye may be an acid dye having an acid group such as a sulfonic acid or carboxylic acid group, or an acid dye and a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, or Salt-forming compounds with primary amine compounds; salt-forming compounds with resin components containing these amino groups and acid dyes, etc. Compounds that form salts from acid dyes and compounds that have an onium base also have good fastness. The compound having an onium salt group is preferably a compound having a cationic group on the side chain. Resins having the above structure are preferred.

[0073] Basic dyes include organic acids, perchloric acid, or salt-forming compounds with these metal salts. Among the salt-forming compounds, salt-forming compounds of basic dyes have various resistances and compatibility with pigments. Preferred because it is superior.

[0074] The chemical structure of dyes can be, for example, azo dyes, disazo dyes, azomethine dyes (India) Aniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes ( Benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, anthrapyridone dyes dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes) , xanthene dyes, acridine dyes, etc.), quinoneimine dyes (oxazine dyes , thiazine dyes, etc.), azine dyes, polymethine dyes (oxonol dyes, mero dyes, etc. Cyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squaryliu chromium-based dyes, croconium-based dyes, quinophthalone-based dyes, phthalocyanine-based dyes, phthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quino dyes Examples include phosphorus dyes, nitro dyes, nitroso dyes, and rhodamine dyes. Among them, azo dyes and xanthene dyes are the most popular from the viewpoint of color characteristics such as hue, color separation, and color uniformity. Dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethyl dyes dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, subfluororesin dyes, Phthalocyanine dyes are preferred, and xanthene dyes, cyanine dyes, triphenylmethan dyes, More preferred are quinone dyes, anthraquinone dyes, dipyrromethene dyes and phthalocyanine dyes. The specific structure of dyes is given in "New Edition Dye Handbook" (Edited by the Society of Organic Synthetic Chemistry; Maruzen, 1970) ), "Color Index" (The Society of Dyers and colorists), "Pigment Handbook" (edited by Okawara et al.; Kodansha, 1986), etc. It is written.

[0075] The colorant (D) can be used alone or in combination of two or more kinds.

[0076] The content of the colorant (D) is 5 to 70 mass % based on 100 mass % of the nonvolatile content of the photosensitive coloring composition. %, and more preferably 10 to 60 mass %. When the content is 70% by mass or less, the sensitivity and pattern formability are further improved. do.

[0077] <Pigment miniaturization> When using an organic pigment as colorant (D), it must be mixed with other raw materials after being subjected to a micronization treatment. The method of the pulverization treatment is preferably, for example, wet grinding, dry grinding, dissolution precipitation, etc. Among these, salt milling using the kneader method, which is a type of wet grinding, is The average primary particle size of the organic pigment after the micronization treatment is preferably 10 to 80 nm. The appropriate particle size improves dispersibility and the coating composition. The average primary particle size was measured by magnification of a TEM (transmission electron microscope). This is the average value of about 20 particles randomly selected from the large image. If there is a length, use the vertical axis length.

[0078] The salt milling process is a process in which a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent is mixed with, for example, , kneader, two-roll mill, three-roll mill, ball mill, attritor, sand mill The mixture is mixed mechanically while being heated using a batch or continuous mixer such as a planetary mixer. After mixing, the water-soluble inorganic salts and water-soluble organic solvents are removed by washing with water. Inorganic salts act as grinding aids, and the high hardness of inorganic salts is utilized during salt milling. By optimizing the conditions for salt milling the pigment, The primary particle size is extremely fine, and the distribution width is narrow and sharp. A pigment can be obtained.

[0079] Examples of water-soluble inorganic salts include sodium chloride, potassium chloride, and sodium sulfate. Among these, sodium chloride (table salt) is preferred from the viewpoint of price. The amount used should be 50 to 2000 parts by mass per 100 parts by mass of pigment, taking into consideration both processing efficiency and production efficiency. The amount is preferably 100 to 1500 parts by mass, and more preferably 300 to 1000 parts by mass.

[0080] The water-soluble organic solvent wets the pigment and the water-soluble inorganic salt. The water-soluble organic solvent is a compound that is miscible with water and does not substantially dissolve water-soluble inorganic salts. A high boiling point solvent with a boiling point of 120°C or higher is preferred as it is less likely to volatilize due to the temperature rise during milling. The soluble organic solvents are, for example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopropyl alcohol), 2-(hexyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol diethylene glycol monoethyl ether, diethylene glycol monobutyl ether ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene Triethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene Examples of the liquid include polyethylene glycol monoethyl ether and liquid polypropylene glycol. The amount of the water-soluble organic solvent used is preferably 5 to 1,000 parts by mass relative to 100 parts by mass of the pigment, A more preferable range is 50 to 500 parts by mass.

[0081] During the salt milling treatment, a resin can be added as needed. The resin may be, for example, a natural resin. Examples of resins include modified natural resins, synthetic resins, and synthetic resins modified with natural resins. It is preferably solid at room temperature, insoluble in water, and more preferably partially soluble in a water-soluble organic solvent. The amount of resin used is preferably 5 to 200 parts by mass relative to 100 parts by mass of the pigment.

[0082] <Dispersant> Dispersants are used to disperse pigments uniformly in the dispersion medium and to maintain this state stably. Generally, pigment derivatives and resin-type dispersants are used.

[0083] <Dye derivatives> The dye derivatives are adsorbed onto the surface of the organic pigment, which makes the surface of the organic pigment polar and biocompatible. The dispersibility of organic pigments improves by increasing the affinity with the binder resin (B) and the resin-type dispersant (described later). The dye derivative is a chemical compound having an acidic group, a basic group, a neutral group, etc. in the organic dye residue. The dye derivatives are compounds having an acid group such as a sulfo group, a carboxy group, or a phosphate group. Compounds having carboxylic acid substituents, and their amine salts, sulfonamide groups, or terminal Compounds with basic substituents such as tertiary amino groups, phenyl groups, and phthalimidoalkyl groups Examples of compounds include compounds having neutral substituents such as the above. Examples of organic pigments include diketopyrrolopyrrole pigments, anthraquinone pigments, and quinacridone pigments. Pigments based on dioxazine, perinone, perylene, thiazine indigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole Pigments based on benzoyls, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthyl pigments, Thorol pigments, threne pigments, metal complex pigments, azo pigments such as azo, disazo, polyazo, etc. Fees, etc.

[0084] The dye derivatives can be used alone or in combination of two or more kinds.

[0085] The content of the dye derivative is preferably 1 to 100 parts by mass relative to 100 parts by mass of the colorant (D). The amount is preferably 3 to 70 parts by mass, and more preferably 5 to 50 parts by mass.

[0086] Adding a dye derivative to a pigment, for example, acid pasting, acid slurry, By using micronization processes such as ly milling, salt milling, and solvent salt milling, The pigment derivative is adsorbed onto the pigment surface, and the primary particles of the pigment are smaller than when the pigment derivative is not added. can be made finer.

[0087] <Resin-type dispersant> The resin-type dispersant has a colorant affinity site that adsorbs to the colorant (D) and an affinity site for components other than the colorant. It has high compatibility and relaxation sites that cause steric repulsion between dispersed particles. Resin-type dispersants include, for example, urethane-based dispersants such as polyurethane, polyacrylic Polycarboxylic acid esters such as acrylates, unsaturated polyamides, polycarboxylic acids, polycarbonates Phosphate (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine Salt, polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester esters, their modified products, poly(lower alkyleneimines) and poly(lower alkyleneimines) having free carboxyl groups. Oil-based dispersants such as amides and their salts formed by reaction with polyesters containing (meth)acrylic acid Acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylic acid ester copolymer , styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Water-soluble resins, water-soluble polymer compounds, polyesters, modified polyacrylates, ethylene oxides oxide / propylene oxide adducts, phosphate esters, etc.

[0088] In terms of functional group type, resin-type dispersants include acidic functional group-containing resin-type dispersants, basic functional group-containing resin-type dispersants, and Examples of the dispersant include a group-containing resin type dispersant. The acidic functional group-containing resin-type dispersant is, for example, a resin-type dispersant having an aromatic carboxylic acid structure. Preferred are those described in, for example, WO2008 / 007776 and JP2008-029901A. JP 2009-155406 A, JP 2010-185934 A, JP 2010-185934 A JP 011-157416 A, JP 2009-251481 A, JP 2007-23 No. 195, Japanese Patent Laid-Open No. 1996-143651, etc.

[0089] The basic functional group-containing resin-type dispersant is, for example, a nitrogen atom-containing graft copolymer or a polymer having a basic functional group-containing resin-type dispersant in a side chain. Nitrogen atoms with functional groups including tertiary amino groups, quaternary ammonium bases, and nitrogen-containing heterocycles. Examples of the dispersing agent include a copolymer containing acrylic acid and a urethane polymer dispersing agent. An acidic functional group-containing resin-type dispersant and a basic functional group-containing resin-type dispersant can also be used in combination.

[0090] The dispersants can be used alone or in combination of two or more.

[0091] The content of the dispersant is preferably 3 to 200 parts by mass relative to 100 parts by mass of the colorant (D). , and more preferably 5 to 100 parts by mass.

[0092] <Multifunctional thiol (F)> The photosensitive coloring composition may contain a polyfunctional thiol (F). The polyfunctional thiol (F) is A compound having two or more thiol (SH) groups. Multifunctional thiol (F) is a compound that can be used for photopolymerization. When used in combination with initiator (A), it acts as a chain transfer agent in the radical polymerization process after light irradiation. It works by generating thiyl radicals that are not easily inhibited by oxygen, resulting in high sensitivity. In particular, polyfunctional aliphatic thiols in which an SH group is bonded to an aliphatic group such as a methylene group or an ethylene group are preferred. stomach.

[0093] The polyfunctional thiol (F) is, for example, hexanedithiol, decanedithiol, 1,4- Butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate , ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate Trimethylolpropane tristhioglycolate, trimethylolpropane tristhiolate propionate, trimethylolpropane tris(3-mercaptobutyrate), pen Pentaerythritol tetrakisthioglycolate, Pentaerythritol tetrakisthiop propionate, trimercaptopropionate tris(2-hydroxyethyl) isocyanate ester, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-tri Azine, 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine, etc. Among these, ethylene glycol bisthiopropionate and trimethylol are preferred. Propane tristhiopropionate, Pentaerythritol tetrakisthiopropionate Examples include:

[0094] The polyfunctional thiol (F) can be used alone or in combination of two or more kinds.

[0095] The content of the polyfunctional thiol (F) is 0.05 to 10 parts by mass relative to 100 parts by mass of the colorant (D). The amount of the polyfunctional thiol (F) is preferably 0 parts by mass, and more preferably 1.0 to 50.0 parts by mass. When 0.05 parts by mass or more is used, crosslinking of the coating after light irradiation is promoted, and in addition to improving development resistance, It can further reduce water stains.

[0096] <Thermosetting compound (G)> The photosensitive coloring composition may contain a thermosetting compound (G). During this process, the thermosetting compound (G) is thermally cured, increasing the crosslink density of the coating and improving the heat resistance. This suppresses aggregation of the colorant (D) during the post-baking process, improving the contrast ratio. The reactive compound (G) may be a low molecular weight compound or a high molecular weight compound such as a resin.

[0097] The thermosetting compound (G) may be, for example, an epoxy compound, an oxetane compound, a benzoguanidine compound, or the like. amine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds , urea compounds, and phenol compounds. Among these, epoxy compounds, Oxetane compounds are preferred

[0098] <Antioxidant (H)> The photosensitive coloring composition may contain an antioxidant (H). The coating formed from the color composition is oxidized by the thermal process of thermal curing and ITO annealing. It is possible to prevent yellowing and suppress a decrease in the transmittance of the coating. In this case, the content of the polymerizable compound is relatively reduced, so the amount of the photopolymerization initiator is increased and the amount of the heat curing agent is reduced. Therefore, by adding an antioxidant, the coating can be easily yellowed. It prevents yellowing due to oxidation during the thermal process and suppresses a decrease in the transmittance of the coating.

[0099] Antioxidants are compounds that have a radical scavenging function or a peroxide decomposition function. The inhibitor may be a hindered phenol compound, a hindered amine compound, a phosphorus compound, Examples of antioxidants include sulfur compounds and hydroxylamine compounds. Among these, compounds that do not contain halogen atoms are preferred, as they are those that can improve the transmittance and sensitivity of the coating. From the viewpoint of compatibility between the degree of purity and the amount of fluorine, hindered phenol compounds, hindered amine compounds, phosphorus compounds, Compounds containing fluorine and sulfur are preferred.

[0100] The antioxidant (H) can be used alone or in combination of two or more kinds.

[0101] The content of the antioxidant (H) is 0.5 to 100% by mass of the nonvolatile content of the photosensitive coloring composition. 5.0% by mass is preferred.

[0102] <Ultraviolet absorber (I), polymerization inhibitor (J)> The photosensitive coloring composition may contain an ultraviolet absorber (I) and a polymerization inhibitor (J). The inclusion of a collector and polymerization inhibitor (J) improves the pattern shape and resolution. Among the absorbents, benzotriazole compounds are, for example, 2-(5-methyl-2-hydroxybenzotriazole) Phenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2 H-Benzotriazole, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl )phenyl]-2H-benzotriazole, 2-(3-t-butyl-5-methyl-2-hydro 2-(2'-hydroxy-5'-t-octyl)-5-chlorobenzotriazole, (ethylphenyl)benzotriazole, 5 parts of 2-methoxy-1-methylethyl acetate and 95 parts of benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1, 1-Dimethylethyl)-4-hydroxy, C7-9 mixed branched and straight chain alkyl esters 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenyl)- phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1- Methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol Methyl 3-(3-(2H-benzotriazol-2-yl)-5-t-butyl-4 -hydroxyphenyl)propionate / polyethylene glycol 300 reaction products, 2-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutane) 2,2'-methylenebis[6-(2H-benzotriazole-2-yl]phenol 2-(2H-benzo[b]phenyl)-4-(1,1,3,3-tetramethylbutyl)phenol], Triazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazo 2-(3,5-di-t-alanyl-2-yl)-6-t-butyl-4-methylphenol 2-[2-hydroxy-5-[2 -(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, octyl -3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazole Azol-2-yl)phenyl]propionate, 2-ethylhexyl-3-[3-te rt-Butyl-4-hydroxy-5-(5-chloro-2H-benzotriazole-2-yl) phenyl]propionate.

[0103] The triazine compounds include, for example, 2,4-bis(2,4-dimethylphenyl)-6-( 2-hydroxy-4-n-octyloxyphenyl)-1,3,5-triazine, 2-[ 4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5 -[3-(dodecyloxy)-2-hydroxypropoxy]phenol, 2-(2,4- Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-trimethylphenyl Reaction product of riazine with (2-ethylhexyl)-glycidic acid ester, 2,4-bis 2-hydroxy-4-butoxyphenyl-6-(2,4-dibutoxyphenyl)-1, 3,5-Triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl) -5-(Hexyloxy)phenol, 2-(4,6-diphenyl-1,3,5-triphenyl)- (2-ethylhexanoyl)-5-[2-(2-ethylhexanoyloxy)ethoxy]phenol , 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)- 1,3,5-triazine and the like.

[0104] Benzophenone compounds include, for example, 2,4-dihydroxybenzophenone, 2-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone -5-sulfonic acid-3H2O, 2-hydroxy-4-n-octoxybenzophenone, 2, 2'-Dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4 '-Dimethoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2 -Hydroxy-4-octadecyloxybenzophenone, 2,2'dihydroxy-4,4' -dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone and the like.

[0105] Examples of salicylate ester compounds include phenyl salicylate and p-octyl salicylate. salicylate, p-tert-butylphenyl salicylate, and the like.

[0106] The polymerization inhibitor may be, for example, catechol, resorcinol, 1,4-hydroquinone, 2 -Methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol catechol, 3-ethylcatechol, 4-ethylcatechol, 2-propylcatechol, 3-propylcatechol propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol 4-n-butylcatechol, 2-tert-butylcatechol, 3-tert-butylcatechol rt-Butylcatechol, 4-tert-butylcatechol, 3,5-di-tert-butylcatechol Alkylcatechol compounds such as ethylcatechol, 2-methylresorcinol, 4-methyl Resorcinol, 2-ethylresorcinol, 4-ethylresorcinol, 2-propyl Resorcinol, 4-propylresorcinol, 2-n-butylresorcinol, 4- n-Butylresorcinol, 2-tert-butylresorcinol, 4-tert-butyl Alkylresorcinol compounds such as methylhydroquinone, ethyl hydroxybenzoate, Hydroquinone, propylhydroquinone, tert-butylhydroquinone, 2,5-di-te Alkylhydroquinone compounds such as rt-butylhydroquinone, tributylphosphine, Trioctylphosphine, tricyclohexylphosphine, triphenylphosphine, Phosphine compounds such as benzylphosphine, trioctylphosphine oxide, tri Phosphine oxide compounds such as phenylphosphine oxide, triphenylphosphine phosphite, trisnonylphenyl phosphite and other phosphite compounds, pyrogallol, These may be used alone or in combination of two or more.

[0107] The content of the ultraviolet absorber (I) and polymerization inhibitor (J) is based on 100 mass of colorant (D). The amount is preferably 0.01 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, relative to the total mass of the hydroxybenzoates. Using the appropriate amount will improve resolution.

[0108] <Solvent> The photosensitive coloring composition may contain a solvent. The solvent may be, for example, 1,2,3-trichloropropane. propane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol Cole diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanol Pandiol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5- Trimethylcyclohexanone, Ethyl 3-ethoxypropionate, 3-methyl-1,3- Butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methyl butyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-methoxybutyl Butanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylbenzene Acetamide, N,N-dimethylformamide, n-butyl alcohol, n-butyl Benzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chloro Toluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-di Ethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone ton, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene Ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene Ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate , ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl Ether, Ethylene Glycol Monobutyl Ether Acetate, Ethylene Glycol Mono Propyl ether, ethylene glycol monohexyl ether, ethylene glycol mono Methyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone diethylene glycol diethyl ether, diethylene glycol dimethyl ether, Diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether Diethylene glycol monobutyl ether, diethylene glycol mono Butyl ether acetate, diethylene glycol monomethyl ether, cyclohexano cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethicone Dipropylene Glycol Methyl Ether, Dipropylene Glycol Methyl Ether Acetate, Dipropylene Glycol dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol Lithium monopropyl ether, dipropylene glycol monomethyl ether, diacetone Toluene alcohol, triacetin, tripropylene glycol monobutyl ether, tripeptide Propylene glycol monomethyl ether, propylene glycol diacetate, propylene Glycol phenyl ether, propylene glycol monoethyl ether, propylene Glycol monoethyl ether acetate, propylene glycol monobutyl ether, Propylene glycol monopropyl ether, propylene glycol monomethyl ether , propylene glycol monomethyl ether acetate, propylene glycol monomethyl Ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexyl Dihexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, Examples include propyl acetate and dibasic acid esters.

[0109] The solvents can be used alone or in combination of two or more.

[0110] The content of the solvent is preferably 100 to 10,000 parts by mass relative to 100 parts by mass of the colorant (D). The content is preferably 500 to 5000 parts by mass, and more preferably 500 to 5000 parts by mass.

[0111] <Silane coupling agent (K)> The photosensitive coloring composition may contain a silane coupling agent, which improves adhesion to the substrate. Sexuality improves. The silane coupling agent (K) is, for example, vinyltris(β-methoxyethoxy)silane. vinyl silanes such as vinylethoxysilane and vinyltrimethoxysilane, γ-methacrylsilane, (Meth)acrylic silanes such as aryloxypropyltrimethoxysilane, β-(3,4-ethylenediamine) β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, Silyl)methyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltri Ethoxysilane, β-(3,4-epoxycyclohexyl)methyltriethoxysilane, γ-Glycidoxypropyltrimethoxysilane, γ-Glycidoxypropyltriethoxy Silanes and other epoxy silanes, N-β(aminoethyl)γ-aminopropyltrimethoxy Silane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(amino (Noethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane methoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyl silane, N-phenyl-γ-aminopropyltriethoxysilane, etc. Silanes, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane Examples include thiosilanes such as ethoxysilane.

[0112] The content of the silane coupling agent (K) is 0.0 with respect to 100 parts by mass of the colorant (D). The amount is preferably 1 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass.

[0113] In addition, the photosensitive coloring composition contains an amine compound that reduces dissolved oxygen. The amine compound may include, for example, triethanolamine, methyldiethanolamine, amine, triisopropanolamine, methyl 4-dimethylaminobenzoate, 4-dimethyl Ethyl aminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethyl benzoate Aminoethyl, 4-dimethylaminobenzoate 2-ethylhexyl, N,N-dimethyl para Toluidine and the like.

[0114] <Leveling Agent (L)> The photosensitive coloring composition may contain a leveling agent (L). The wettability to the light substrate and the drying property of the coating are further improved. Polyionic surfactants, fluorosurfactants, nonionic surfactants, cationic surfactants These may be used alone or in combination of two or more. Use.

[0115] The content of the leveling agent (L) is 0.0% by mass based on 100% by mass of the nonvolatile content of the photosensitive coloring composition. The content is preferably 0.01 to 2.0 mass %, and more preferably 0.005 to 1.0 mass %. The photosensitive coloring composition has a high level of balance among coatability, pattern adhesion, and transmittance.

[0116] <Other ingredients> <Storage stabilizer> The photosensitive coloring composition may contain a storage stabilizer. By containing the storage stabilizer, the composition The storage stabilizer can stabilize the viscosity over time. pentaerythritol-tetrakis[3-(3,5-di-t -butyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octyl Thio)-6-(4-hydroxy-3,5-di-t-butylanilino)1,3,5-triazol- hindered phenols such as phosphine, tetraethylphosphine, triphenylphosphine, Organic phosphines such as tetraphenylphosphine, zinc dimethyldithiophosphate, dipropyl Phosphites such as zinc dibutyldithiophosphate and molybdenum dibutyldithiophosphate, dodecyl sulfide, benzothiophene and other sulfur-based compounds, benzyltrimethylchloride, diethyl Quaternary ammonium chlorides such as hydroxylamine, organic acids such as lactic acid and oxalic acid, and These may be used alone or in combination of two or more. .

[0117] The content of the storage stabilizer is 0.01 to 20 parts by mass relative to 100 parts by mass of the colorant (D). It is preferable that the content is 0.05 to 10 parts by mass, and more preferable that the content is 0.05 to 10 parts by mass. When an appropriate amount is contained, the stability over time is improved. .

[0118] <Method for producing photosensitive coloring composition> The photosensitive coloring composition is prepared by dispersing a colorant (D), a dispersant, a solvent, etc. In addition, when the colorant (D) has high solubility in the solvent, the dispersion process When two or more types of colorant (D) are used in combination, A colorant dispersion can be prepared by mixing the colorant (D) in the same manner as above. The colorant dispersion can be prepared by the above steps. Next, the colorant dispersion is mixed with a photopolymerization initiator (A), a binder resin (B), and a photopolymerizable compound. (C) is blended and mixed to obtain a photosensitive coloring composition. It goes without saying that the timing is arbitrary.

[0119] The dispersion treatment can be carried out using, for example, a kneader, a two-roll mill, a three-roll mill, a ball mill, Dispersion by horizontal sand mill, vertical sand mill, annular bead mill, or attritor The device can be used.

[0120] <Removal of large particles> The photosensitive coloring composition is centrifuged at a gravitational acceleration of 3,000 to 25,000 G, and is then filtered using a sintered filter or By means of filtration using a membrane filter, coarse particles of 5 μm or more, preferably 1 μm Coarse particles of 0.5 μm or more, more preferably coarse particles of 0.5 μm or more, and mixed dust are removed. In this way, it is preferable that the coloring composition does not substantially contain particles of 0.5 μm or more. It is more preferable that the thickness is 0.3 μm or less.

[0121] <Color filter> The color filter of the present specification comprises a substrate and a filter formed from a photosensitive coloring composition. The color filter segment (hereinafter also referred to as the filter segment) is provided. By appropriately selecting the type of colorant (D) to be used, a red filter segment, a green It is preferable that the color filter segment has a blue filter segment and a blue filter segment. The color filter is a color filter segment, and the magenta color filter segment is The filter segment may have a cyan color filter segment and a yellow color filter segment. The substrate is preferably a transparent substrate or a reflective substrate. The transparent substrate may be, for example, a glass substrate. Reflective substrates include, for example, substrates that use aluminum electrodes or thin metal films as their reflective surfaces. can be done.

[0122] <Color filter manufacturing method> The color filter is formed by first forming a black matrix on the substrate, then forming a filter segment. It is preferable to form a thin film transistor (TFT) on the substrate. The black matrix can be formed after the insulating layer is formed. The black matrix may be made of, for example, chromium, chromium / chromium oxide multilayer, or titanium nitride. and resin films in which a light-blocking agent is dispersed.

[0123] The photolithography method involves, for example, applying a photosensitive coloring composition containing a colorant of a certain color tone to a photosensitive layer. The resulting solution is applied onto the substrate to form a film having a dry thickness of about 0.2 to 5 μm. The resulting coating (hereinafter referred to as the first coating) is exposed to light (light) through a mask having a predetermined pattern. Then, the film is immersed in a solvent or alkaline developer or is sprayed with The developer is then sprayed onto the film to develop it, and the uncured portions are removed to obtain the desired pattern. The same procedure is carried out using photosensitive coloring compositions having colorants of other colors to obtain filters of each color. A color filter having a photosensitive layer can be produced by adding a photosensitive layer to the first coating before exposure. A second coating (oxygen barrier film) is formed using polyvinyl alcohol or water-soluble acrylic resin. This prevents the first coating from coming into contact with oxygen, further improving the exposure sensitivity. The color filter is formed by curing the uncured photopolymerizable compound in the filter segment. Heating can be carried out.

[0124] The coating device may be, for example, a spray coater, a spin coater, a slit coater, or a roll coater. A drying step can be carried out during the coating process. The drying device may be, for example, a hot air dryer. Examples include ovens and infrared heaters.

[0125] The developer is an alkaline developer, such as sodium carbonate or sodium hydroxide. inorganic alkalis such as dimethylbenzylamine, triethanolamine, and other organic alkalis; In addition, a defoaming agent or a surfactant can be added to the developer.

[0126] In this specification, the color filter is formed by attaching a filter segment to an opposing substrate using a sealant. The liquid crystal is injected through the injection port provided in the seal, and the injection port is then sealed. If necessary, a polarizing film or a retardation film is attached to the outside of the substrate to create a liquid crystal display device. This liquid crystal display device can be manufactured using, for example, twisted nematic (TN), super - Twisted Nematic (STN), In-Plane Switching (IPS) , Vertical Alignment (VA), Optically Convenient Bend (OCB) and others.

[0127] In this specification, the color filter is applicable to solid-state imaging devices, organic EL display devices, as well as liquid crystal display devices. Can be used for quantum dot displays, electronic paper, head-mounted displays, etc. .

[0128] <Image display device> The image display device of this specification includes a color filter. The image display device further includes a light source. A liquid crystal display device will be described as an example of an image display device. The liquid crystal display device includes a color filter and a light source. The light source may be, for example, a cold cathode fluorescent lamp (CFL). CFL), white LED, but in this invention, the red reproduction range is widened It is preferable to use a white LED. 1 is a schematic cross-sectional view of a liquid crystal display device 10. The device 10 shown in FIG. It comprises a pair of transparent substrates 11 and 21, between which liquid crystal LC is sealed.

[0129] Liquid crystal displays (LC) are classified into TN (Twisted Nematic), STN (Super Twisted Nematic), and IPS ( In-Plane switching), VA(Vertical Alignment), OCB(Optically Compensated) The first transparent substrate 11 has an inner surface on which a liquid crystal layer is formed, and the liquid crystal layer is aligned in accordance with a driving mode such as birefringence. A TFT (thin film transistor) array 12 is formed on which, for example, ITO or On the transparent electrode layer 13, an alignment layer 14 is provided. In addition, a polarizing plate 15 is formed on the outer surface of the transparent substrate 11.

[0130] On the other hand, the color filter 22 of the present invention is formed on the inner surface of the second transparent substrate 21. The red, green, and blue filter segments that make up the color filter 22 are black. They are separated by a matrix (not shown).

[0131] A transparent protective film (not shown) is formed to cover the color filter 22 as needed. A transparent electrode layer 23 made of, for example, ITO is formed thereon, and a An alignment layer 24 is provided.

[0132] A polarizing plate 25 is formed on the outer surface of the transparent substrate 21. A backlight unit 30 is provided on the other side.

[0133] White LED light sources include blue LEDs with a fluorescent filter on the surface, and blue LEDs. There are some EDs that contain phosphor in the resin package, and they emit light in the range of 430nm to 485nm. It has a wavelength (λ3) where the emission intensity is maximum within the range of 530 nm to 580 nm. It has a wavelength (λ4) at which the intensity is maximum, and the emission intensity is extremely high within the range of 600 nm to 650 nm. The wavelength (λ5) at which the emission intensity is greatest is λ3, and the emission intensity I3 at wavelength λ4 is The ratio of light intensity I4 (I4 / I3) is 0.2 or more and 0.4 or less, and the light emission intensity at wavelength λ3 is The ratio of the intensity I3 to the emission intensity I5 at wavelength λ5 (I5 / I3) is 0.1 or more and 1.3 or less. A white LED light source (LED1) with spectral characteristics of 430nm to 485nm is used. The second light emitting diode has a wavelength (λ1) at which the light intensity is maximum and is within the range of 530 nm to 580 nm. The emission intensity I1 at wavelength λ1 and the emission intensity I2 at wavelength λ2 are White LED with spectral characteristics where the ratio of light intensity I2 (I2 / I1) is between 0.2 and 0.7 A light source (LED2) is preferred.

[0134] Specifically, LED1 is NSSW306D-HG-V1 (manufactured by Nichia Chemical Co., Ltd.), NS Examples include SW304D-HG-V1 (manufactured by Nichia Chemical Industries, Ltd.).

[0135] Specifically, LED2 is NSSW440 (manufactured by Nichia Corporation), NSSW304D ( (manufactured by Nichia Chemical Co., Ltd.)

[0136] The image display device in this specification includes not only a liquid crystal display device but also a solid-state image pickup device, an organic EL display device, a It can be used for applications such as dot display devices, electronic paper, and head-mounted displays. [Example]

[0137] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. In addition, "parts" means parts by mass, and "%" means % by mass.

[0138] PGMAc stands for propylene glycol monomethyl ether acetate.

[0139] Prior to the examples, the average molecular weight of the resin, as well as the acid value, amine value, and ammonia value of the resin were measured. We will explain how to calculate the sodium salt value.

[0140] (average molecular weight of resin) The number average molecular weight (Mn) and weight average molecular weight (Mw) of the resin were measured using a gel with an RI detector. Measurement was performed by gel permeation chromatography (GPC). Two separation columns were connected in series using 0GPC (manufactured by Tosoh Corporation), and both columns contained Using two TSK-GEL SUPER HZM-N ovens in series, oven temperature was set at 4°C. The measurement was performed at 0°C, using a THF solution as the eluent, and at a flow rate of 0.35 ml / min. was dissolved in a solvent consisting of 1 wt% of the above eluent, and 20 microliters was injected. All values ​​are polystyrene equivalent values.

[0141] (resin acid value) Add 80 ml of acetone and 10 ml of water to 0.5 to 1 g of resin solution and stir to dissolve evenly. The titration solution was 0.1 mol / L KOH solution, and the titration was carried out with an automatic titrator (COM-5 The acid value (mgKOH / g) of the resin solution was measured by titration using a titrator (Hiranuma Sangyo Co., Ltd.). Then, calculate the acid value per nonvolatile content of the resin from the acid value of the resin solution and the concentration of nonvolatile content of the resin solution. I put it out.

[0142] (Amine value of basic resin type dispersant) The amine value of the basic resin-type dispersant was measured in accordance with the method of ASTM D 2074. This is the total amine value (mgKOH / g) converted into non-volatile content.

[0143] (Ammonium salt value of resin having cationic groups on the side chain) The ammonium salt value of resins with cationic groups on the side chains is determined by a 5% potassium chromate aqueous solution. is used as an indicator and titrated with 0.1N silver nitrate solution, and then the equivalent amount of potassium hydroxide is calculated. This is a converted value and indicates the ammonium salt value of the non-volatile matter.

[0144] <Production of finely divided pigments> (Fine Pigment (PB-1)) Copper phthalocyanine blue pigment CI Pigment Blue 15:6 (Toyocolor 100 parts of "Lionol Blue ES" manufactured by SANYO Co., Ltd., 1000 parts of crushed table salt, and 100 parts of ethylene glycol was charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.). The mixture was poured into 3,000 parts of hot water and heated to about 70°C. The mixture was stirred for about an hour in a high-speed mixer while stirring to form a slurry, which was then filtered and washed with water. After removing the salt and solvent, the mixture was dried at 80°C for 24 hours to obtain the finely divided pigment (PB-1). Got it.

[0145] (Fine Pigment (PB-2)) Copper phthalocyanine blue pigment CI Pigment Bl, a finely divided pigment (PB-1) ue15:6 is a copper phthalocyanine blue pigment, CI Pigment Blue 15 (Zhuhai Oriental Technology Co., Ltd.) The only pigments used were micronized pigments (PB-1 ) to obtain a finely divided pigment (PB-2).

[0146] (Micronized pigment (PV-1)) Dioxazine-based purple pigment CI Pigment Violet 23 (Toyo Color Co., Ltd.) 200 parts of "LIONOGEN VIOLET RL" manufactured by the company, 1400 parts of sodium chloride 360 parts of diethylene glycol were mixed in a stainless steel 1-gallon kneader (Inoue Seisakusho) The mixture was then placed in a mixing chamber (manufactured by Epson Corporation) and kneaded at 80°C for 6 hours. The mixture was heated to 80°C and stirred for 2 hours to form a slurry, which was then filtered and washed with water repeatedly to obtain sodium chloride. After removing thorium and diethylene glycol, the mixture is dried at 85°C for one day to produce a finely divided purple pigment. (PV-1) was obtained.

[0147] (Micronized pigment (PG-1)) In a reaction vessel, 1250 parts of n-amyl alcohol, 225 parts of phthalodinitrile, and 225 parts of ammonium chloride were added. 78 parts of aluminum anhydride was added and stirred. 266 parts of cyclo[5.4.0]undec-7-ene) was added, and the mixture was heated to 136°C. The reaction solution was refluxed for 5 hours, and cooled to 30°C while stirring. The resulting mixture was poured into a mixed solvent of 10,000 parts of water with stirring to obtain a blue slurry. The mixture was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to give a 135 100g of chloroaluminum phthalocyanine was obtained. 100 parts of phthalocyanine was slowly added to 1200 parts of concentrated sulfuric acid at room temperature. After stirring for 1 hour, the sulfuric acid solution was poured into 24,000 parts of cold water at 3°C. The blue precipitate was filtered and After washing and drying, 102 parts of aluminum phthalocyanine pigment represented by the following formula (2) was obtained. .

[0148] Formula (2) [ka]

[0149] In a reaction vessel, 1000 parts of methanol is added to the aluminum phthalocyanine compound represented by formula (2). 100 parts of acrylic pigment and 49.5 parts of diphenyl phosphate were added, heated to 40°C, and reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and then dried. 114 parts of an aluminum phthalocyanine pigment represented by the following formula (3) was obtained. 100 parts of the obtained aluminum phthalocyanine pigment represented by formula (3) and sodium chloride 1200 parts of ethanol and 120 parts of diethylene glycol were mixed in a stainless steel 1-gallon kneader ( The mixture was placed in a mixing machine (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 70°C for 6 hours. The mixture is heated to 70°C and stirred for 1 hour to form a slurry, which is then filtered and washed with water repeatedly. After removing sodium chloride and diethylene glycol, the mixture is dried at 80°C for 24 hours and then pulverized. A pigment (PG-1) was obtained. The volume average primary particle diameter was 31.2 nm.

[0150] Formula (3) [ka]

[0151] (Micronized pigment (PG-2)) In a reaction vessel, 1000 parts of methanol is added to the aluminum phthalocyanine compound represented by formula (2). Add 100 parts of the pigment and 43.2 parts of diphenylphosphinic acid, heat to 40°C, The reaction was carried out for 8 hours, and after cooling to room temperature, the product was filtered, washed with methanol, and then dried. This gave 112 parts of an aluminum phthalocyanine pigment represented by the following formula (4). The aluminum phthalocyanine pigment represented by formula (4) thus obtained was used as a finely divided pigment (PG- The same treatment as in 1) was carried out to obtain a finely divided pigment (PG-2). The volume average primary particle diameter was 29.5n It was m.

[0152] Formula (4) [ka]

[0153] (Micronized pigment (PG-3)) According to the synthesis method described in JP-A-2010-79247, An aluminum phthalocyanine pigment was obtained. The aluminum phthalocyanine pigment represented by formula (5) thus obtained was used as a finely divided pigment (PG-1 The volume average primary particle diameter was 33.0 nm. It was.

[0154] Formula (5) [ka]

[0155] (Micronized pigment (PG-4)) Into a three-neck flask, 500 parts of 98% sulfuric acid and 5 parts of phthalocyanine pigment represented by the following formula (6) were added. 0 parts, 1,2-dibromo-5,5-dimethylhydantoin (DBDMH) 104.4 parts The mixture was stirred and reacted at 20°C for 4 hours. Then, the reaction mixture was added to 5000 parts of ice water at 3°C. The precipitated solid was collected by filtration and washed with water. 500 parts of the solution and the filtered residue were added, and the mixture was stirred at 80°C for 1 hour. The pigment was collected, washed with water, and dried to obtain a pigment in which an average of 8.0 bromine atoms were substituted on the phthalocyanine ring. Ta.

[0156] Next, 500 parts of N-methylpyrrolidone was added to a three-necked flask. 50 parts of a pigment substituted with an average of 8.0 bromine atoms and 18.2 parts of diphenyl phosphate The mixture was heated to 90°C and reacted for 8 hours. After cooling to room temperature, the product was filtered and After washing with ethanol, the mixture was dried to obtain a finely divided pigment (PG-4) represented by the following formula (7). The volume average primary particle diameter of the resulting colorant was 27 nm.

[0157] [ka]

[0158] (Micronized pigment (PG-5)) In a three-neck flask, 500 parts of N-methylpyrrolidone and 50 parts of a pigment in which an average of 8.0 bromine atoms were substituted on the phthalocyanine ring prepared by 13.8 parts of diphenylphosphinic acid was added, heated to 90°C, and reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain the compound represented by the following formula (8): The resulting colorant had a volume average primary particle diameter of 31n It was m.

[0159] Formula (8) [ka]

[0160] (Micronized pigment (PG-6)) In a three-neck flask, 500 parts of N-methylpyrrolidone and 50 parts of a pigment in which an average of 8.0 bromine atoms were substituted on the phthalocyanine ring prepared by 21.5 parts of bis(4-nitrophenyl)phosphate was added, heated to 90°C, and reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, dried, and then subjected to the following procedure. A finely divided pigment (PG-6) represented by formula (9) was obtained. The volume average primary particle size of the obtained colorant was The diameter was 32 nm.

[0161] Formula (9) [ka]

[0162] (Micronized pigment (PG-7)) In a three-necked flask, 500 parts of 98% sulfuric acid and 50 parts of the phthalocyanine pigment represented by formula (6) Add 129.3 parts of 1,2-dibromo-5,5-dimethylhydantoin (DBDMH) and stir. The mixture was stirred and reacted at 20° C. for 6 hours. Thereafter, the reaction mixture was poured into 5000 parts of ice water at 3° C. The precipitated solid was collected by filtration and washed with water. 500 parts of the filtered residue was added, and the mixture was stirred at 80°C for 1 hour. After washing with water and drying, a pigment was obtained in which an average of 10.1 bromine atoms had been substituted on the phthalocyanine ring. .

[0163] Next, 500 parts of N-methylpyrrolidone was added to a three-necked flask. 50 parts of pigment substituted with an average of 10.1 bromine atoms and 13.9 parts of diphenyl phosphate The mixture was heated to 90°C and reacted for 8 hours. After cooling to room temperature, the product was filtered. After washing with methanol, the mixture was dried to obtain a finely divided pigment (PG-7) represented by the following formula (10): The volume average primary particle diameter of the obtained colorant was 27 nm.

[0164] Formula (10) [ka]

[0165] (Micronized pigment (PG-8)) Melt 203 parts of aluminum bromide, 47 parts of sodium bromide, and 5 parts of ferric bromide by heating. Then, 50 parts of the phthalocyanine pigment represented by formula (6) was added at 140°C. The mixture was reacted at 160°C for 7 hours while 215.4 parts of bromine was blown into the mixture. The reaction mixture was poured into 500 parts of the mixture, and the precipitated solid was collected by filtration and washed with water. Wash in this order with water, warm water, 1% sodium hydroxide solution, and warm water, then dry and remove the odor. 98 parts of brominated aluminum phthalocyanine was obtained. Cyanine was dissolved in 980 parts of concentrated sulfuric acid and stirred at 50°C for 3 hours. The above sulfuric acid solution was poured into 00 parts of the mixture, and the precipitated solid was collected by filtration, washed with water, and dried. 500 parts of 2.5% aqueous sodium hydroxide solution and the filtered residue were added to the car, and the mixture was heated at 80°C for 1 hour. After that, the mixture was filtered, washed with water, and dried to remove the bromine atom from the phthalocyanine ring. The pigment obtained had an average of 15.0 substitutions.

[0166] Next, 500 parts of N-methylpyrrolidone was added to a three-necked flask. 50 parts of a pigment substituted with an average of 11.9 bromine atoms and 10.8 parts of diphenyl phosphate The mixture was heated to 90°C and reacted for 8 hours. After cooling to room temperature, the product was filtered. After washing with methanol, the mixture was dried to obtain a finely divided pigment (PG-8) represented by the following formula (11): The volume average primary particle diameter of the obtained colorant was 31 nm.

[0167] Formula (11) [ka]

[0168] (Micronized pigment (PG-9)) In a three-neck flask, add 250 parts of aluminum chloride, 60 parts of sodium chloride, and 2.25 parts of iodine. The mixture was added and stirred at 150°C for 30 minutes. 50 parts of anine pigment was added, and the mixture was stirred at 155°C for 30 minutes to dissolve the pigment. 58.5 parts of cyanuric acid was added, and the mixture was stirred at 190°C for 5 hours. The reaction mixture was poured into a beaker, and the precipitated solid was collected by filtration and washed with water. 500 parts of an aqueous sodium chloride solution and the filtered residue were added, and the mixture was stirred at 80°C for 1 hour. The mixture was filtered, washed with water, and dried to obtain a phthalocyanine compound with an average of 8.1 chlorine atoms substituted on the phthalocyanine ring. The pigment was obtained.

[0169] Next, 500 parts of N-methylpyrrolidone and the obtained phthalocyanine ring were added to a three-necked flask. 50 parts of a pigment with an average of 11.9 bromine atoms substituted on the The mixture was heated to 90°C and reacted for 8 hours. After cooling to room temperature, the product was filtered. After washing with methanol, the mixture was dried to obtain a finely divided pigment (PG-9) represented by the following formula (12): The volume average primary particle diameter of the obtained colorant was 29 nm.

[0170] Formula (12) [ka]

[0171] (Finely divided pigments (PY-1 to 3)) According to the examples of JP 2012-226110 A, quinolone compounds having the following formulas (13) to (15) were prepared. We created finely divided Talon pigments (PY-1 to 3), the structures of which are shown below.

[0172] [ka]

[0173] (Fine Pigment (PY-4)) CI Pigment Yellow 138 (PY138) (BASF Japan "Palioto" 100 parts of "Color Yellow K0960-HD", 700 parts of sodium chloride, and diethylene 180 parts of glycol was placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded for 8 minutes. The mixture was mixed at 80°C for 6 hours. The mixture was added to 2000 parts of warm water and mixed for 1 hour while heating to 80°C. The mixture was stirred for 8 hours to form a slurry, and then filtered and washed with water repeatedly to remove salt and solvent. After drying at 0°C for one day and night, a finely divided pigment (PY-4) was obtained.

[0174] (Fine Pigment (PY-5)) Isoindoline yellow pigment CI Pigment Yellow 139 (BASF 100 parts of "Irgaphor Yellow 2R-CF" manufactured by Japan Co., Ltd., 1600g of sodium chloride 190 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader and kneaded for 60 minutes. The mixture was then mixed at 80°C for 10 hours. Then, the mixture was poured into 3 liters of hot water and heated to about 80°C. The mixture was stirred for about an hour in a high-speed mixer while stirring to form a slurry, which was then filtered and washed with water. After removing the sodium chloride and solvent, the mixture was dried at 80°C for one day and night to obtain the finely divided pigment (PY- 5) was obtained.

[0175] (Fine Pigment (PY-6)) Yellow pigment CI Pigment Yellow 185 (BASF Japan "Paris" Otol Yellow D1155): 500 parts, sodium chloride: 500 parts, and diethylene 250 parts of glycol were placed in a stainless steel 1-gallon kneader and mixed at 120°C for 8 hours. Next, the kneaded mixture was poured into 5 liters of warm water and stirred for 1 hour while heating to 70°C. The slurry is filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol. After removing the residue, the mixture was dried at 80°C for 24 hours to obtain a finely divided pigment (PY-6).

[0176] (Fine Pigment (PY-7)) Metal complex yellow pigment (CI Pigment Yellow 150, manufactured by LANXESS) 100 parts of "Yellow Pigment E4GN", 1600 parts of sodium chloride 190 parts of diethylene glycol were mixed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.). ) and kneaded for 10 hours at 60°C. Next, this mixture was poured into 3 liters of warm water. The mixture was heated to about 80°C and stirred in a high-speed mixer for about 1 hour to form a slurry, which was then filtered. After removing the sodium chloride and solvent by repeated filtration and washing with water, the product was dried at 80°C for one day and night. A finely divided pigment (PY-7) was obtained.

[0177] <Dye manufacturing method> (Resin 1 having cationic groups on the side chains) Methyl ethyl ether was placed in a four-neck separable flask equipped with a thermometer, a stirrer, a distillation tube, and a condenser. 67.3 parts of methyl methacrylate were charged and heated to 75°C under a nitrogen stream. 34.0 parts of n-butyl methacrylate, 28.0 parts of 2-ethylhexyl methacrylate 28.0 parts of dimethylaminoethyl methacrylate, 10.0 parts of 2,2'-azobisulfite 6.5 parts of 2,4-dimethylvaleronitrile, and 25.1 parts of methyl ethyl ketone After homogenizing the mixture, place it in a dropping funnel, attach it to a four-neck separable flask, and let it soak for 2 hours. Two hours after the completion of the dropwise addition, the polymerization yield was 98% or more based on the nonvolatile content, and the weight average The average molecular weight (Mw) was confirmed to be 6830, and the mixture was cooled to 50°C. 3.2 parts of ethanol and 22.0 parts of ethanol were added, and the mixture was reacted at 50°C for 2 hours. The mixture was heated to 80°C and allowed to react for a further 2 hours. Resin 1 having a cationic group on the side chain having an ammonium group was obtained. The ammonium salt value was 34 mg KOH / g.

[0178] (Dye (RD-1)) The following procedure was used to prepare CI Acid Red 52 and Resin 1, which has a cationic group on the side chain. A dye (RD-1) was produced, which is a salt-forming compound consisting of the following: 30 parts of resin 1 having a cationic group on the side chain in terms of nonvolatile matter was added to 2000 parts of water, After thorough stirring and mixing, the mixture was heated to 60°C. Meanwhile, 10 parts of CI Al were added to 90 parts of water. An aqueous solution of Cid Red 52 was prepared and added dropwise to the resin solution. After the dropwise addition, the mixture was stirred at 60°C for 120 minutes to allow the reaction to proceed satisfactorily. The reaction solution was dropped onto paper, and the point at which no bleeding occurred was the end point, indicating that the salt-forming compound had been obtained. After cooling to room temperature while stirring, the mixture was filtered by suction, washed with water, and then placed on filter paper. The remaining salt-forming compound was dried in a dryer to remove moisture, and then mixed with 32 parts of CI Acid Red. A dye (RD-1) which is a salt-forming compound of resin 52 and resin 1 having a cationic group on the side chain was used. At this time, the effective pigment derived from CI Acid Red 52 in the dye (RD-1) was The content of the component was 25% by mass.

[0179] <Dye derivatives>

[0180] [ka]

[0181] (Resin-type dispersant (a2-1) solution) Into a reaction vessel equipped with a gas inlet tube, a thermostat, a condenser, and a stirrer, 10 parts of methacrylic acid, methacrylic acid, 100 parts of i-butyl methacrylate, 70 parts of benzyl methacrylate 20 parts of methyl parathion and 50 parts of PGMAc were charged, and the contents of the reaction vessel were replaced with nitrogen gas. The inside of the reaction vessel was heated to 50°C. The mixture was stirred, and 12 parts of 3-mercapto-1,2-propanediol was added. The temperature was raised to 90°C. A solution of 0.1 parts of 2,2'-azobisisobutyronitrile in 90 parts of PGMAc was added. The reaction was continued for 7 hours while adding the pyrophosphate. Measurement of the non-volatile content confirmed that 95% of the pyrophosphate had reacted. Mellitic anhydride 19 parts, PGMAc 50 parts, cyclohexanone 50 parts, 1, Add 0.4 parts of 8-diazabicyclo-[5.4.0]-7-undecene and heat at 100°C for 7 minutes. The reaction was continued for 1 hour. Measurement of the acid value confirmed that 98% or more of the acid anhydride was half-esterified. After confirming this, the reaction was terminated, and the solution was diluted with PGMAc to a non-volatile content of 30%. A resin-type dispersant (a2-1) solution having a weight average molecular weight of 8,500 and a viscosity of 1000 gKOH / g was obtained.

[0182] (Resin-type dispersant (a2-2) solution) A reactor equipped with a gas inlet tube, a condenser, a stirring blade, and a thermometer was charged with methyl methacrylate. 30 parts of n-butyl methacrylate, 30 parts of n-butyl methacrylate, 2 parts of hydroxyethyl methacrylate 13.2 parts of tetramethylethylenediamine were charged, and the mixture was heated to 50°C for 1 minute while flowing nitrogen. The mixture was stirred for 1 hour, and the atmosphere in the system was replaced with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate, 5 parts of cuprous chloride, 0.6 parts of PGMAc and 133 parts of PGMAc were charged, and the temperature was raised to 110°C under a nitrogen stream. After 4 hours of polymerization, the polymerization solution was sampled and the non-volatile The polymerization conversion rate was confirmed to be 98% or more based on the nonvolatile content. Next, 61 parts of PGMAc, 2 parts of 2-block (A block) monomer, 20 parts of 1,2,2,6,6-pentamethylpiperidyl methacrylate (Hitachi Chemical Co., Ltd.) (Fancryl FA-711MM, manufactured by FANCRIL) was added and the temperature was maintained at 110°C under a nitrogen atmosphere. The reaction was continued with stirring. 1,2,2,6,6-Pentamethylpiperidyl methacrylate Two hours after addition, the polymerization solution is sampled and the non-volatile content is measured, and the calculation is performed from the non-volatile content. It was confirmed that the polymerization conversion rate of the second block (A block) was 98% or more, and the reaction solution The solution was cooled to room temperature to terminate the polymerization. Then, PGMAc was added to the solution to make the non-volatile content 30%. The amine value per nonvolatile matter was 57 mg KOH / g and the number average molecular weight was 4,500. A solution of a resin-type dispersant (a2-2) having a piperidyl skeleton of (Mn) was obtained.

[0183] (Resin-type dispersant (a2-3) solution) The method for producing the pigment dispersant (1) described in Production Example 1 of Japanese Patent No. 5513691, -(N,N-dimethylamino)propylacrylamide / methoxypolyethyleneglycol Quaternized methacrylate copolymer (23 / 77% by mass; quaternization rate 27% by mol)] was synthesized and diluted with PGMAc to a non-volatile content of 30%, and a resin-type dispersant (a2- 3) A solution was prepared.

[0184] <Production of alkali-soluble resin> (Preparation of Alkali-Soluble Resin (B-1)) A thermometer, a condenser, a nitrogen gas inlet tube, a dropping tube, and a stirring device were attached to a separable four-neck flask. 196 parts of cyclohexanone was charged into the attached reaction vessel, and the temperature was raised to 80°C. After replacing with nitrogen, 20.0 parts of benzyl methacrylate and n-butyl methacrylate were added through the dropping tube. 17.2 parts of 2-hydroxyethyl methacrylate, 12.9 parts of methacrylic acid 0.0 parts, paracumylphenol ethylene oxide modified acrylate (manufactured by Toagosei Co., Ltd.) 20.7 parts of RONIX M110) and 1.1 parts of 2,2'-azobisisobutyronitrile The mixture was added dropwise over 2 hours. After the addition was completed, the reaction was continued for another 3 hours to obtain a resin solution. Ta. After cooling to room temperature, PGMAc was added to the mixture to adjust the non-volatile content to 20% by mass. A solution of soluble resin (B-1) was prepared. The weight average molecular weight (Mw) was 26,000. The non-volatile acid value was 91 mg KOH / g.

[0185] (Preparation of Alkali-Soluble Resin (B-2)) Attach a thermometer, a condenser, a nitrogen gas inlet tube, a dropping tube and a stirring device to a separable four-neck flask. 207 parts of cyclohexanone was charged into a reaction vessel equipped with a nitrogen gas. The temperature was raised to 80°C. After substitution, 20 parts of methacrylic acid, 20 parts of benzyl methacrylate, Cumylphenol ethylene oxide modified acrylate (Aronix M1 manufactured by Toagosei Co., Ltd.) 10) 20 parts, methyl methacrylate 25 parts, 2-hydroxyethyl methacrylate 8.5 A mixture of 1.33 parts of 2,2'-azobisisobutyronitrile and 1.33 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After the dropwise addition was completed, the reaction was continued for another 3 hours to obtain a copolymer resin solution. After stopping the nitrogen gas and injecting dry air into the entire polymer solution for 1 hour, the solution was stirred. After cooling to room temperature, 2-methacryloyloxyethyl isocyanate (Showa Denko Karenz MOI 6.5 parts, dibutyltin laurate 0.08 parts, cyclohexanone 26 The mixture from part 1 was added dropwise at 70°C over 3 hours. After the addition was completed, the reaction was continued for another hour. Add cyclohexanone to the fat solution so that the nonvolatile content becomes 20% by mass, and then add alkali. A soluble resin (B-2) solution was prepared. The weight average molecular weight (Mw) was 18,000. The non-volatile acid value was 130 mg KOH / g.

[0186] (Preparation of Alkali-Soluble Resin (B-3) (Alkali-Soluble Resin (I))) A separable four-neck flask equipped with a thermometer, a condenser, a nitrogen gas inlet tube, and a stirrer 100 parts of PGMAc was placed in a container, and heated to 120°C while injecting nitrogen gas into the container. At the same temperature, 5.2 parts of styrene, 35.5 parts of glycidyl methacrylate, and dicyclohexyl methylpropional were added from the dropping tube. A mixture of 41.0 parts of pentanyl methacrylate and 1.0 part of azobisisobutyronitrile The polymerization reaction was carried out by dropwise addition over 2.5 hours. Next, the inside of the flask was purged with air, and 17.0 parts of acrylic acid was added to tris(dimethylaminomethyl)phenyl. 0.3 parts of alcohol and 0.3 parts of hydroquinone were added, and the reaction was continued at 120°C for 5 hours. The reaction was terminated when the volatile acid value reached 0.8, and the weight average molecular weight reached approximately 12,000 ( A resin solution of 30.4 parts of tetrahydrophthalic anhydride was obtained. 0.5 parts of triethylamine was added and the reaction was completed at 120°C for 4 hours. PGMAc was added so that the alkali-soluble resin (B-3) solution was prepared. The partial acid value was 88 mg KOH / g.

[0187] (Preparation of Alkali-Soluble Resin (B-4) (Alkali-Soluble Resin (II))) A flask equipped with a stirrer, thermometer, reflux condenser, dropping funnel, and nitrogen inlet tube was charged with PGM After introducing 182g of Ac and changing the atmosphere in the flask from air to nitrogen, the temperature was raised to 100°C. Benzyl methacrylate 70.5 g (0.40 mol), methacrylic acid 43.0 g (0.5 mol), tricyclodecane-based monomethacrylate (FA-513M manufactured by Hitachi Chemical Co., Ltd.) A mixture of 2.0 g (0.10 mol) of HCl and 136 g of PGMAc was added to the A solution containing 3.6 g of nitrile was added dropwise to the flask from the dropping funnel over 2 hours, and then The mixture was stirred at 100°C for 5 hours. Then, the atmosphere in the flask was changed from nitrogen to air, and the glycerol 35.5 g (0.25 moles) of dimethacrylate (carbonyl methacrylate of the methacrylic acid used in this reaction) 50 mol%) relative to the hydroxyl group], 0.9 g of trisdimethylaminomethylphenol, and 0.145 g of hydroquinone was added to the flask, and the reaction was continued at 110°C for 6 hours. Cyclohexanone was added so that the nonvolatile content was 20% by mass, and the alkali-soluble A resin (B-4) solution was obtained. The weight average molecular weight was 13,000, and the molecular weight distribution (Mw / Mn ) was 2.1, and the non-volatile acid value was 79 mg KOH / g.

[0188] <Method for producing pigment dispersion>

[0189] [Preparation of blue pigment dispersion (M-B1)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a blue pigment dispersion (M-B1). Finely divided pigment (PB-1) 9.05 parts Micronized pigment (PV-1) 0.31 parts Dye (RD-1) 4.16 parts Dye derivative (a1-1) 1.04 parts Resin-type dispersant (a2-1) solution 3.47 parts Alkali-soluble resin (B-1) solution 2.00 parts PGMAc 79.97 parts

[0190] [Preparation of blue pigment dispersion (M-B2)] Blue pigment dispersion except that the micronized pigment (PB-1) was replaced with the micronized pigment (PB-2) A blue pigment dispersion (M-B2) was prepared in the same manner as (M-B1).

[0191] [Preparation of green pigment dispersion (M-G1)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a green pigment dispersion (M-G1). CI Pigment Green 58 (DIC "FASTOGEN GREEN A110" ”) 7.68 copies A mixture of equal amounts of finely divided pigments (PY-1), (PY-2), (PY-3), and (PY-4) 1.92 copies Resin-type dispersant (a2-1) solution 3.20 parts 3.20 parts of an equal mixture of resin-type dispersant (a2-2) solution and (a2-3) solution Alkali-soluble resin (B-1) solution 22.40 parts PGMAc 61.60 parts

[0192] [Preparation of green pigment dispersion (M-G2)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a green pigment dispersion (M-G2). Micronized pigments (PG-4), (PG-5), (PG-6), (PG-7), (PG-8), 5.76 parts of an equal mixture of (PG-9) A mixture of equal amounts of finely divided pigments (PY-1), (PY-2), (PY-3), and (PY-4) 3.84 copies Resin-type dispersant (a2-1) solution 3.20 parts 3.20 parts of an equal mixture of resin-type dispersant (a2-2) solution and (a2-3) solution Alkali-soluble resin (B-1) solution 22.40 parts PGMAc 61.60 parts

[0193] [Preparation of green pigment dispersion (M-G3)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a green pigment dispersion (M-G3). 7.68 parts of an equal mixture of finely divided pigments (PG-1), (PG-2), and (PG-3) CI Pigment Green 1.92 parts of 58 (DIC "FASTOGEN GREEN A110") Resin-type dispersant (a2-1) solution 3.20 parts 3.20 parts of an equal mixture of resin-type dispersant (a2-2) solution and (a2-3) solution Alkali-soluble resin (B-1) solution 22.40 parts PGMAc 61.60 parts

[0194] [Preparation of Yellow Pigment Dispersion (M-Y1)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a yellow pigment dispersion (M-Y1). Micronized pigment (PY-7) 9.60 parts Dye derivative (a1-2) 0.96 parts Resin-type dispersant (a2-1) solution 3.20 parts 22.40 parts of an equal mixture of alkali-soluble resin (B-1) solution and (B-2) solution PGMAc 63.84 parts

[0195] [Preparation of Yellow Pigment Dispersion (M-Y2)] The fine pigment (PY-7) is a mixture of equal amounts of the fine pigment (PY-5) and the fine pigment (PY-6). A yellow pigment dispersion (M-Y1) was prepared in the same manner as the yellow pigment dispersion (M-Y1), except that the yellow pigment dispersion (M-Y2) was replaced with a yellow pigment dispersion (M-Y3). -Y2) was produced.

[0196] [Preparation of red pigment dispersion (M-R1)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a red pigment dispersion (M-R1). CI Pigment Red 254 (BASF Japan "Irgafor Red B-CF" ) 8.96 copies CI Pigment Red 177 (BASF Japan "Cromophtal Red A2B") ”) 2.24 copies Dye derivative (a1-3) 1.12 parts Resin-type dispersant (a2-1) solution 3.73 parts 12.80 parts of an equal mixture of alkali-soluble resin (B-1) solution and (B-2) solution PGMAc 71.15 parts

[0197] [Preparation of black pigment dispersion (M-BK1)] After mixing the mixture of the following composition uniformly, it was mixed with zirconia beads of 1 mm in diameter. , 5 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") After dispersion, the mixture was filtered through a 5 μm filter to prepare a black pigment dispersion (M-BK1). Carbon black (Mitsubishi Chemical "MA77") 11.20 parts Dye derivative (a1-2) 1.12 parts Resin-type dispersant (a2-1) solution 3.73 parts 12.80 parts of an equal mixture of alkali-soluble resin (B-1) solution and (B-2) solution PGMAc 71.15 parts

[0198] Other materials used in the photosensitive coloring composition of this study are listed below. <Photopolymerization initiator (A)> (A1): Compound No. 3 mentioned above (A2): Compound No. 5 mentioned above (A3): Compound No. 6 mentioned above (A4): Compound No. 8 mentioned above (A5): A mixture of equal amounts of (A1) to (A4)

[0199] <Photopolymerization initiator (Y)> (Y-1): 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanol Pan-1-one [Omnirad 907 (IGM Resins)] and 2-benzo 2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 [Omni rad 369 (IGM Resins) (Y-2): 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide [Omnirad TPO (manufactured by IGM Resins)] (Y-3): 2,2'-bis(o-chlorophenyl)-4,5,4',5'-tetraphenyl Nyl-1,2'-biimidazole [biimidazole (Kurokane Chemicals)] (Y-4): 1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2 -(O-benzoyloxime) [Irgacure OXE01 (BASF Japan)] Ethan-1-one, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazo] 1-(O-acetyloxime) [Irgacure OXE02 (BASF A mixture of equal parts of [manufactured by Japan Co., Ltd.].

[0200] <Sensitizer (E)> 2,4-Diethylthioxanthone [Kayacure DETX-S (Nippon Kayaku)] and 4,4 '-Bis(diethylamino)benzophenone [CHEMARK DEABP(CHEMA A mixture of equal parts of RK Chemical Co., Ltd.

[0201] <Photopolymerizable compound (C)> C1 prepared as follows: Aronix M310 manufactured by Toagosei Co., Ltd., Aronix M310 manufactured by Toagosei Co., Ltd. A mixture of equal amounts of M520 manufactured by Nippon Kayaku Co., Ltd. and KAYARAD DPCA-30 manufactured by Nippon Kayaku Co., Ltd. (Production of Photopolymerizable Monomer (C1)) In a 2 L four-neck flask, 801 parts of dipentaerythritol pentaacrylate, hexane 128 parts of methylethylene diisocyanate, 1.0 parts of N,N-dimethylbenzylamine, 4- 1.0 part of methoxyphenol was added and reacted at 70°C for 8 hours. , the disappearance of the isocyanate absorption was confirmed. After cooling to room temperature, 70.3 parts of mercaptopropionic acid was added and the temperature was raised to 50-60°C. The reaction was carried out for 6 hours at this temperature to obtain a photopolymerizable monomer (C1). The photopolymerizable monomer (C1) has an acid value of 43, a urethane group number of 1.53 mmol / g, and a double bond. The number of binding groups was 6.88 mmol / g.

[0202] <Multifunctional thiol (F)> Trimethylolpropane tris(3-mercaptobutyrate) [TPMB (Showa Denko K.K.)] )] and pentaerythritol tetrakis(3-mercaptopropionate) [PEMP( A mixture of equal parts of [manufactured by Sakai Chemical Industry Co., Ltd.].

[0203] <Thermosetting compound solution> 1,2-epoxy-4-(2-) of 2,2'-bis(hydroxymethyl)-1-butanol Oxiranyl)cyclohexane adduct [EHPE-3150 (Daicel)] and Sorbic acid Glycidyl etherified epoxy compound of tungsten [Denacol EX611 (Nagase Chemtech)] A mixture of equal amounts of 30 parts by mass of PEG-400 (manufactured by PEG-400 Co., Ltd.) was dissolved in 70 parts by mass of PGMAc.

[0204] <Antioxidant (H)> BASF Japan IRGANOX1010, ADEKA Adeka Stab LA-52 , ADEKA ADK STAB PEP-36, ADEKA ADK STAB AO-412 An equal mixture of S.

[0205] <Ultraviolet absorber (I)> BASF Japan TINUVIN P, BASF Japan TINUVIN 405 and an equal mixture of KEMISORB 10 manufactured by Chemipro Chemicals.

[0206] <Polymerization inhibitor (J)> Equal mixture of 3-methylcatechol, methylhydroquinone, and tert-butylhydroquinone thing.

[0207] <Silane coupling agent (K)> 3-Glycidoxypropyltriethoxysilane, 3-Methacryloxypropyltriethoxysilane Silane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-methyl A mixture of equal parts of propylcaptopropyltrimethoxysilane.

[0208] <Leveling Agent (L)> 1 copy of BYK-330 manufactured by BYK-Chemie, 0 copies of Megafac F-551 manufactured by DIC A mixed solution of 0.5 parts of Kao's "Emulgen 103" and 0.5 parts of PGMAc was dissolved in 98 parts. liquid.

[0209] <Organic solvents> PGMAc, cyclohexanone, ethyl 3-ethoxypropionate, 1,3-butylene glycol Lithium diacetate and 3-methoxy-1-butanol in a mass ratio of 3:1:1:1: Mixture of 1.

[0210] [Examples 1 to 25 and Comparative Examples 1 to 3] (Preparation of Photosensitive Coloring Compositions (R-B1 to 20, R-G1 to 4, R-R1 to 3, R-BK1) The materials were mixed and stirred in the formulation ratios shown in Tables 1 to 4, and then filtered through a 1 μm filter to obtain photosensitive coloring compositions of the respective colors. In this specification, Examples 1 to 10 and 15 to 19 are reference examples.

[0211] [Table 1]

[0212] [Table 2]

[0213] [Table 3]

[0214] [Table 4]

[0215] The photosensitive coloring compositions obtained were evaluated by the following methods. The results are shown in Tables 5 and 8. The meaning of the evaluation rank is as follows: ◎: extremely good, ◯: good, △: practical, × :Not suitable for practical use [Pattern formation] The obtained photosensitive coloring composition was applied by spin coating to a 100mm x 100mm x 0. After coating on a 7 mm thick glass substrate (Corning Eagle 2000), The solvent was removed by heating in a flask at 70°C for 15 minutes, and a coating film of approximately 2 μm was obtained. After cooling the plate to room temperature, a high-pressure mercury lamp was used to illuminate the plate with 100 μm width (pitch 200 μm) and 10 μ 20 mW / cm illuminance through a photomask with a stripe pattern of 20 μm width (pitch 20 μm) 2 , 50 mJ / cm 2The substrate was then exposed to light at 23°C using a nonionic surfactant solution. After spray development using an aqueous developer containing 0.12% potassium hydroxide and 0.04% potassium hydroxide, The sample was washed with ion-exchanged water, air-dried, and then heated in a clean oven at 230°C for 30 minutes. - Development is possible for the coating of each photosensitive coloring composition, with no residual development residue. The development time was determined as the shortest possible time. The thickness of the coating was measured using Dektak 3030 (manufactured by Japan Vacuum Engineering Co., Ltd.). [Linearity evaluation] The pattern formed by the above method was measured using a Nikon ECLIPSE LV100 Observation and evaluation were carried out using a POL Model optical microscope. The evaluation criteria were as follows: do. ◎: The difference between the maximum and minimum line widths is less than 1 μm ○: The difference between the maximum and minimum line widths is 1 μm or more and less than 2 μm △: The difference between the maximum and minimum line widths is 2 μm or more and less than 3 μm ×: The difference between the maximum and minimum line widths is 3 μm or more

[0216] [Resolution evaluation] The pattern formed by the above method was analyzed using Nikon ECLIPSE LV100 Observation and evaluation were carried out using a POL Model optical microscope. The evaluation criteria were as follows: Poor resolution means that adjacent stripe patterns are connected or missing. The evaluation criteria are as follows: ◎: No connected or missing parts in the pattern ○: Patterns are connected or missing in less than 5% of the total area △: Patterns are connected or missing in 5% to less than 20% of the total area ×: The pattern is connected or missing in 20% or more of the whole.

[0217] [Remaining film rate evaluation] In the above pattern formation, the film thickness was measured after spray development, washing with ion-exchanged water, and air drying. This film thickness was used as the film thickness after development. After that, the film was heated in a clean oven at 230°C for 30 minutes. The film thickness was measured at the same location as the film thickness before development. This film thickness was used as the film thickness after baking. The remaining film thickness was calculated from the two film thicknesses using the following formula and was evaluated as follows: Formula: Residual film rate (%) = film thickness after baking ÷ film thickness after development × 100 ◎:Remaining film rate 90% or more ○: Remaining film rate is 85% or more but less than 90% △: Remaining film rate is 80% or more but less than 85% ×: Remaining film rate is less than 80%

[0218] [Water stain evaluation] The obtained photosensitive coloring composition was applied to a 100 mm long x 100 mm wide, 0.7 mm thick glass The solution was applied to a substrate (Corning Eagle 2000) and placed on a hot plate (As One " Pre-baked at 95°C for 2 minutes using EC-1200N (trade name), resulting in a film thickness of 3.4 μm. Then, the film was sprayed with high-pressure water through a mask having a stripe pattern of 100 μm width. Illumination intensity 20mW / cm using a silver lamp 2 , 40 mJ / cm 2 UV exposure was carried out under the conditions Then, an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide was added. The pattern was developed by immersing the substrate in the developing solution at 23°C for 40 seconds, and then washed with pure water. The observation was carried out using an optical microscope, ECLIPSE LV100POL Model manufactured by N Co., Ltd. The pricing standards are as follows: ◎: There were no water stains. ○: Water stains were less than 10% of the solid area. △: Water stains were 10% or more but less than 30% of the solid area. ×: Water stains were present in 30% or more of the solid area.

[0219] [Table 5]

[0220] [Table 6]

[0221] [Table 7]

[0222] [Table 8]

[0223] From the results in the above table, it can be seen that the photosensitive coloring compositions of Examples 1 to 25 are practically usable in all evaluations. The results were above the performance level. [Explanation of symbols]

[0224] 10 LCD display device 11 Transparent substrate 12 TFT array 13 Transparent electrode layer 14 Alignment layer 15 Polarizing plate 21 Transparent substrate 22 Color Filter 23 Transparent electrode layer 24 Alignment layer 25 Polarizing Plate 30 Backlight unit 31 White LED light source LC liquid crystal

Claims

1. The composition contains a photopolymerization initiator (A) represented by the following general formula (1), another photopolymerization initiator (Y), a binder resin (B), a photopolymerizable compound (C), and a colorant (D), the photopolymerization initiator (Y) contains one or more compounds selected from the group consisting of oxime ester compounds, acetophenone compounds, phosphine compounds, and imidazole compounds; the content of the photopolymerization initiator (A) represented by the general formula (1) is 1 to 13 parts by mass relative to 100 parts by mass of the colorant (D); The content of the other photopolymerization initiator (Y) is 0.5 to 200 parts by mass relative to 100 parts by mass of the colorant (D), The content of the colorant (D) is 5 to 70 mass% in 100 mass% of the nonvolatile content of the photosensitive coloring composition. General formula (1) 【Chemical 1】 (In the formula, R １ and R ２ are each independently R １１ or COR １１ represents R １１ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R １１ The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may have a branched side chain or may be a cyclic alkyl, R ３ represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R ３ The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by R ３ The hydrogen atoms of the aryl group, arylalkyl group or heterocyclic group represented by ２１ , OR ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -NCOR ２２ -OCOR ２３ , N.R. ２２ COR ２１ , O.C.O.R. ２１ , SCOR ２１ , OCSR ２１ , COSR ２１ , CSOR ２１ , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR ２１ may be substituted with R ２１ , R ２２ and R ２３ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R ２１ , R ２２ and R ２３ The hydrogen atoms of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by R may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group. ２１ , R ２２ and R ２３ The alkyl group, aryl group, arylalkyl group, or alkylene portion of the heterocyclic group represented by the formula: ２４ -, -NR ２４ CO-, -NR ２４ COO-,-OCONR ２４ the oxygen atoms may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-, provided that they are not adjacent to each other; R ２４ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; R ２４ The alkyl moiety of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by the formula (I) may have a branched side chain or may be a cyclic alkyl, R ４ represents a hydrogen atom, a hydroxyl group, CN, a nitro group, or a halogen atom, and n represents 0 or 1.

2. 2. The photosensitive coloring composition according to claim 1, wherein the binder resin (B) comprises an alkali-soluble resin having a carboxy group and a polymerizable unsaturated group in a side chain selected from the following (I) and (II): (I) An alkali-soluble resin obtained by reacting a reaction product of an epoxy group in a polymer having an epoxy group with a carboxyl group-containing monomer with a polybasic acid or a polybasic acid anhydride. (II) Alkali-soluble resins which are reaction products of carboxy groups in a polymer having carboxy groups with epoxy group-containing monomers.

3. The photosensitive coloring composition according to claim 1 or 2, further comprising a polyfunctional thiol (F).

4. A color filter comprising a substrate and filter segments or a black matrix formed from the photosensitive coloring composition according to any one of claims 1 to 3.

5. An image display device comprising the color filter according to claim 4.

Images