Photosensitive Coloring Composition, Color Filter, and Image Display Device

Abstract

An object of the present invention is to provide a photosensitive coloring composition that can suppress watermarks on a film after development, has a good residual film rate, and can form a pattern with a good shape, a color filter formed using the photosensitive coloring composition, and an image display device including the color filter. The photosensitive coloring composition includes a photopolymerization initiator (A), a binder resin (B), a photopolymerizable compound (C), and a colorant (D) represented by the following general formula (1). General formula (1).

Description

Technical Field

[0001] The present invention relates to a photosensitive coloring composition for manufacturing a color filter used in a liquid crystal display device, a solid-state imaging device, an organic electroluminescence (EL) display device, a quantum dot display device, an electronic paper, etc., a color filter formed using the photosensitive coloring composition, and an image display device including the color filter. Background Art

[0002] A color filter is formed by arranging two or more fine strip-shaped filter segments having different hues in parallel (in a stripe shape) or crossing each other on a transparent substrate such as a glass substrate, or by arranging two or more fine filter segments having different hues in an orderly manner in each of the longitudinal and transverse directions. The filter segments have small sizes of several micrometers to several hundred micrometers and are arranged neatly for each hue.

[0003] Currently, as a method for manufacturing a color filter, a filter segment pattern of a first color is obtained through the following steps: a step of coating a photosensitive coloring composition on a transparent substrate such as glass and removing the solvent from the coating film by drying; a step of irradiating the coating film with radiation through a photomask having a desired pattern shape to harden it (hereinafter referred to as exposure); then, a step of cleaning and removing the unexposed portion of the coating film (hereinafter referred to as development); and thereafter, a heat treatment step (hereinafter referred to as post-baking) is performed as needed to sufficiently harden the hardened film. Moreover, filter segment patterns of other colors are formed by performing the same operations, and the color filter is completed by combining these.

[0004] In the development step, an alkaline developer is used as the developer, and the unexposed portion is cleaned and removed. At this time, there are problems that the exposed portion is missing or peeled off, resulting in defects in the pattern shape. In addition, there is also a problem that when the coating film is exposed to the alkaline developer, a phenomenon of color change of the coating film (hereinafter referred to as watermark) occurs. Therefore, a photosensitive coloring composition that does not cause defects in the pattern shape and watermarks in the development step is required. Furthermore, there is a problem that the film thickness of the coating film changes due to the dissolution and vaporization of unreacted substances, etc. during the development step and the post-baking step (hereinafter, the ratio of the change in the film thickness is referred to as the residual film rate).

[0005] Therefore, Patent Document 1 discloses a photosensitive coloring composition containing a resin-type surfactant having a fluorinated alkyl group. In addition, Patent Document 2 discloses a photosensitive coloring composition containing a resin having a side chain with a polymerizable unsaturated group at the end of a polyalkylene oxide chain containing a poly(perfluoroalkylene ether) chain.

[0006] In addition, as a measure for improving watermarks, Patent Document 3 discloses a colored photosensitive resin composition containing a base-soluble resin having a specific structure and an oxime ester fluorene derivative compound as a photopolymerization initiator. In addition, Patent Document 4 discloses a resist composition containing a fluorine-based surfactant having a specific structure.

[0007] [Prior Art Documents]

[0008] [Patent Documents]

[0009] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-164965

[0010] [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-65865

[0011] [Patent Document 3] Japanese Patent Application Laid-Open No. 2017-173787

[0012] [Patent Document 4] Japanese Patent Application Laid-Open No. 2016-102212 Summary of the Invention

[0013] [Problems to be Solved by the Invention]

[0014] However, existing photosensitive coloring compositions have problems such as insufficient suppression of watermarks and difficulty in obtaining a pattern with a good shape. In addition, there is also a problem of a large reduction in the pattern shape and the film thickness of the pattern after post-baking (low residual film ratio).

[0015] An object of the present invention is to provide a photosensitive coloring composition that can suppress watermarks on the film after development, has a good residual film ratio, and can form a pattern with a good shape.

[0016] [Technical Means for Solving the Problems]

[0017] One embodiment of the present invention relates to a photosensitive coloring composition containing a first photopolymerization initiator represented by the following general formula (1), a binder resin, a photopolymerizable compound, and a colorant.

[0018] General formula (1)

[0019]

[0020] In the formula, R1 and R2 each independently represent R 11 or COR 11 , 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. The alkyl part of the alkyl group, aryl group, arylalkyl group or heterocyclic group represented by R 11 may be a branched side chain or a cyclic alkyl group. 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. R4 represents a hydrogen atom, a hydroxyl group, a cyano group (-CN), a nitro group or a halogen atom, and n represents 0 or 1.

[0021] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein the binder resin contains a base-soluble resin selected from the group consisting of the following (I), (II) and (III) and having a carboxyl group and a polymerizable unsaturated group in the side chain.

[0022] (I) A base-soluble resin obtained by reacting a polybasic acid or polybasic anhydride and a reaction product of an epoxy group in a polymer having an epoxy group with a carboxyl group-containing monomer, and further containing a polycyclic alicyclic monomer unit.

[0023] (II) A base-soluble resin which is a reaction product of a carboxyl group in a polymer having a carboxyl group and a monomer containing an epoxy group, and further contains a polycyclic alicyclic monomer unit.

[0024] (III) A base-soluble resin which is a reaction product of a hydroxyl group in a polymer having a hydroxyl group and a carboxyl group and a monomer containing an isocyanate group.

[0025] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, further comprising a polyfunctional thiol.

[0026] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, further comprising a second photoinitiator different from the first photoinitiator.

[0027] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein the second photoinitiator contains one or more compounds selected from the group consisting of oxime ester compounds, acetophenone compounds, phosphine compounds and imidazole compounds.

[0028] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein the second photoinitiator contains a third photoinitiator represented by the following general formula (2), and the first photoinitiator contains a fourth photoinitiator represented by the following general formula (3).

[0029] General formula (2)

[0030]

[0031] In the formula, R1 represents an alkyl group having 4 to 20 carbon atoms with an alicyclic hydrocarbon group. R2 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. R3 represents a hydrogen atom, a nitro group, a group having an ether bond, or an aromatic group.

[0032] General formula (3)

[0033]

[0034] In the formula, R4 and R5 each independently represent 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.

[0035] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein, based on 100 parts by mass of the total content of the third photopolymerization initiator and the fourth photopolymerization initiator, the content of the third photopolymerization initiator is 5 parts by mass to 95 parts by mass.

[0036] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, further comprising a fifth photopolymerization initiator different from the first photopolymerization initiator and the second photopolymerization initiator.

[0037] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein the second photopolymerization initiator contains the third photopolymerization initiator represented by the general formula (2), and the first photopolymerization initiator contains the fourth photopolymerization initiator represented by the general formula (3).

[0038] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein, based on 100 parts by mass of the total content of the photopolymerization initiators contained in the photosensitive coloring composition, the total content of the third photopolymerization initiator and the fourth photopolymerization initiator is 30 parts by mass or more.

[0039] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein the polymerizable compound contains a polymerizable compound having a structure derived from ε-caprolactone.

[0040] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, wherein the polymerizable compound contains a polymerizable compound having an acidic group.

[0041] Another embodiment of the present invention relates to the photosensitive coloring composition as described above, and further includes a sensitizer.

[0042] Another embodiment of the present invention relates to a color filter including a substrate and a filter segment formed using the photosensitive coloring composition.

[0043] Another embodiment of the present invention relates to an image display device including the color filter.

[0044] [Effects of the Invention]

[0045] According to an embodiment of the present invention, there can be provided a photosensitive coloring composition capable of suppressing watermarks on the film after development, having a good residual film rate, and forming a pattern with a good shape, a color filter including the photosensitive coloring composition, and an image display device including the color filter. Description of the Drawings

[0046] Figure 1 It is a schematic cross-sectional view of a liquid crystal display device.

[0047] Description of Reference Numerals

[0048] 10: Liquid crystal display device

[0049] 11, 21: Transparent substrate

[0050] 12: TFT array

[0051] 13, 23: Transparent electrode layer

[0052] 14, 24: Alignment layer

[0053] 15, 25: Polarizing plate

[0054] 22: Color filter

[0055] 30: Backlight unit

[0056] 31: White LED light source

[0057] LC: Liquid crystal Detailed Description of the Embodiments

[0058] In this specification, unless otherwise specified, “(meth)acryloyl”, “(meth)acrylic group”, “(meth)acrylic acid”, “(meth)acrylate” or “(meth)acrylamide” respectively mean “acryloyl and / or methacryloyl”, “acrylic group and / or methacrylic group”, “acrylic acid and / or methacrylic acid”, “acrylate and / or methacrylate”, or “acrylamide and / or methacrylamide”. “C.I.” means Colour Index (C.I.; published by The Society of Dyers and Colourists). The colorant may include a pigment and a dye. The monomer and the polymerizable unsaturated group may include a vinyl group and a (meth)acryloyl group. The monomer is a monomer containing a polymerizable unsaturated group.

[0059] <Photopolymerizable Coloring Composition>

[0060] The photopolymerizable coloring composition of this embodiment contains: a photopolymerization initiator (A) represented by the following general formula (1), a binder resin (B), a photopolymerizable compound (C), and a colorant (D). The photopolymerizable coloring composition can be applied to a substrate to form a film, for example. The film can form a pattern with a desired shape by photolithography. The pattern is preferably post-baked to be hardened. The film formed from the photopolymerizable coloring composition is preferably used in a color filter segment and a black matrix constituting a color filter.

[0061] The photopolymerizable coloring composition of this embodiment contains the photopolymerization initiator (A) represented by the following general formula (1), and the photocuring property of the composition is improved, whereby the watermark of the film can be surprisingly suppressed. In addition, through efficient photocuring, the residual film rate is good, and a pattern with a good shape can be formed.

[0062] [Photopolymerization Initiator (A)]

[0063] The photopolymerizable coloring composition contains the photopolymerization initiator (A) represented by the general formula (1).

[0064] General formula (1)

[0065]

[0066] In the formula, R1 and R2 each independently represent R 11 or COR 11 , 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 11The alkyl moiety of the represented alkyl, aryl, arylalkyl or heterocyclic group may be a branched side chain or a cyclic alkyl group. 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. R4 represents a hydrogen atom, a hydroxyl group, a cyano group (-CN), a nitro group or a halogen atom. n represents 0 or 1.

[0067] In addition, the alkyl, aryl, arylalkyl or heterocyclic group represented by R3 may have a substituent. The substituent may be, for example, an alkyl group. When the alkyl, aryl, arylalkyl or heterocyclic group represented by R3 has an alkyl group as a substituent, the alkyl moiety may be a branched side chain or a cyclic alkyl group. The hydrogen atom of the aryl, arylalkyl or heterocyclic group represented by R3 may be further substituted by R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , NR 22 COR 21 , OCOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, a cyano group (-CN), a halogen atom or COOR 21 substituted, 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. The hydrogen atom of the alkyl, aryl, arylalkyl or heterocyclic group represented by R 21 , R 22 and R 23 may be further substituted by a hydroxyl group, a nitro group, a cyano group (-CN), a halogen atom, or a carboxyl group. In the alkyl moiety or the alkylene moiety of the alkyl, aryl, arylalkyl or heterocyclic group represented by R 21 , R 22 and R 23 , -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR24 -SCO-, -COS-, -OCS- or -CSO- may contain 1 to 5 under the condition that oxygen atoms are not adjacent (peroxy group is not formed);

[0068] 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. The alkyl group, aryl group, arylalkyl group, or alkyl moiety of the heterocyclic group represented by R 24 may be a branched side chain or a cyclic alkyl group.

[0069] R3, R 11 、R 21 、R 22 、R 23 and R 24 Examples of the alkyl group having 1 to 20 carbon atoms represented by R include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, tert-pentyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, tert-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, cyclopentyl, cyclopentylmethyl, cyclopentylethyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl, etc.

[0070] R3, R 11 、R 21 、R 22 、R 23 and R 24 Examples of the aryl group having 6 to 30 carbon atoms represented by R include: phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, phenanthryl, and the above alkyl groups substituted with one or more of phenyl, biphenyl, naphthyl, anthryl, etc.

[0071] R3, R 11 、R 21 、R 22 、R 23 and R 24 Examples of the arylalkyl group having 7 to 30 carbon atoms represented by R include: benzyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl, etc.

[0072] R3, R 11 、R 21 、R 22 、R 23 and R 24Examples of the heterocyclic group having 2 to 20 carbon atoms represented include 5- to 7-membered heterocycles such as pyridyl, pyrimidinyl, furyl, thienyl, tetrahydrofuryl, dioxolanyl, benzoxazol-2-yl, tetrahydropyranyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isoxazolidinyl, piperidinyl, piperazinyl, and morpholinyl.

[0073] As the photopolymerization initiator (A) represented by the general formula (1), for example, it may contain a photopolymerization initiator (A') represented by the following general formula (3).

[0074] General formula (3)

[0075]

[0076] In the formula, R4 and R5 each independently represent 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.

[0077] Examples of the alkyl group having 1 to 20 carbon atoms in R4 and R5 may be linear, branched, cyclic, or a group formed by bonding them, and include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, hexadecyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, etc.

[0078] Examples of the aryl group having 6 to 30 carbon atoms in R4 and R5 include phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, etc.

[0079] Examples of the arylalkyl group having 7 to 30 carbon atoms in R4 and R5 include benzyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl, etc.

[0080] Examples of the heterocyclic group having 2 to 20 carbon atoms in R4 and R5 include pyridyl, pyrimidinyl, furyl, tetrahydrofuryl, dioxolanyl, imidazolidinyl, oxazolidinyl, piperidinyl, morpholinyl, etc. Among them, from the viewpoint of suppressing watermarks on the film, R4 is preferably an alkyl group having 1 to 12 carbon atoms or an arylalkyl group having 7 to 15 carbon atoms, and more preferably an alkyl group having 3 to 8 carbon atoms. From the viewpoint of reactivity, R5 is preferably methyl, ethyl, or phenyl, and more preferably methyl or ethyl.

[0081] The photopolymerization initiator (A') can be used alone or in combination of two or more.

[0082] The method for producing the photopolymerization initiator (A') is not particularly limited, and existing methods can be used.

[0083] As specific compounds of the photopolymerization initiator (A), for example, the following Compound No. 1 to Compound No. 8, and the following Structural Formulas (1) to (4) can be cited. In addition, the present embodiment is not limited by any of these.

[0084]

[0085]

[0086]

[0087] The photopolymerization initiator (A) has high sensitivity, and in particular, it can suppress the watermark of the film after development while obtaining a film with a high residual film rate, so a photosensitive coloring composition capable of forming a color filter with good quality can be obtained. In addition, the photosensitive coloring composition containing the photopolymerization initiator can form a filter section and a black matrix with excellent heat resistance, pattern shape, developability, and chemical resistance.

[0088] From the viewpoints of suppressing the watermark of the film and the pattern shape, the content of the photopolymerization initiator (A) is preferably 1 to 100 parts by mass, more preferably 1 to 50 parts by mass, still more preferably 1 to 30 parts by mass, and particularly preferably 2 to 15 parts by mass with respect to 100 parts by mass of the colorant (D). When it is 100 parts by mass or less, the linearity and resolution during pattern formation are further improved. When it is 1 part by mass or more, the watermark of the film can be further suppressed.

[0089] [Photopolymerization initiator (Y)]

[0090] In the photosensitive coloring composition, in addition to using the photopolymerization initiator (A), a photopolymerization initiator (Y) different from the photopolymerization initiator (A) can be used in combination. Thereby, a better pattern can be formed.

[0091] As the photopolymerization initiator (Y), for example, a photopolymerization initiator (Y') represented by the following general formula (2) can be included.

[0092] General formula (2)

[0093]

[0094] In the formula, R1 represents an alkyl group having an alicyclic hydrocarbon group and having 4 to 20 carbon atoms. R2 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. R3 represents a hydrogen atom, a nitro group, a group having an ether bond, or an aromatic group.

[0095] Examples of the alicyclic hydrocarbon group in R1 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. Among them, from the perspective of reactivity, cyclopentyl and cyclohexyl are preferred, and from the perspective of suppressing watermarks, cyclohexyl is more preferred.

[0096] The alkyl group having 1 to 20 carbon atoms in R2 can be linear, branched, cyclic, or a group formed by bonding them. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, hexadecyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, etc.

[0097] Examples of the aryl group having 6 to 30 carbon atoms in R2 include phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, etc.

[0098] Examples of the arylalkyl group having 7 to 30 carbon atoms in R2 include benzyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl, etc.

[0099] Examples of the heterocyclic group having 2 to 20 carbon atoms in R2 include pyridyl, pyrimidinyl, furyl, tetrahydrofuryl, dioxolanyl, imidazolidinyl, oxazolidinyl, piperidyl, morpholinyl, etc.

[0100] Among them, from the perspective of reactivity, methyl, ethyl, or phenyl is preferred, and methyl or ethyl is more preferred.

[0101] When R3 is a group showing aromaticity, the aromatic ring part can be a monocyclic ring or a condensed ring. In addition, it can be a hydrocarbon ring or a heterocyclic ring. Particularly preferably, it has a structure in which R3 has a carbonyl group and the rings are bonded to each other via the carbonyl group. Examples of the group showing aromaticity include groups having a benzene ring, furan ring, thiophene ring, naphthalene ring, benzofuran ring, benzothiophene ring, indole ring, etc. From the perspective of reactivity, R3 is preferably a hydrogen atom or a nitro group, and more preferably a hydrogen atom.

[0102] The photoinitiator (Y') can be used alone or in combination of two or more.

[0103] The production method of the photoinitiator (Y') is not particularly limited, and existing methods can be used. For example, the method described in Japanese Patent Application Laid-Open No. 2012-526185 can be used.

[0104] Specific compounds as the photoinitiator (Y') include, for example, the following structural formulas (5) to (10). In addition, the present embodiment is not limited to any of these.

[0105]

[0106]

[0107] Structural formula (9)

[0108]

[0109] Structural formula (10)

[0110]

[0111] In addition, examples of the photoinitiator (Y) include: acetophenone-based compounds such as 4-phenoxydichloroacetophenone, 4-tert-butyldichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-2-(benzyl)-1-butanone, or 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone; benzoin-based compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzil dimethyl ketal; benzophenone-based compounds such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone; thioxanthone-based compounds such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, or 2,4-diethylthioxanthone; triazine-based compounds such as 2,4,6-trichlorotriazine, 2-phenyl-4,6-bis(trichloromethyl)triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)triazine, 2-piperonyl-4,6-bis(trichloromethyl)triazine, 2,4-bis(trichloromethyl)-6-styryl triazine, 2-(naphthalen-1-yl)-4,6-bis(trichloromethyl)triazine, 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine; oxime ester-based compounds such as 1,2-octanedione, 1-[4-(phenylthio)phenyl]-,2-(O-benzoyl oxime), or ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(O-acetyl oxime); phosphine-based compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, or diphenyl-2,4,6-trimethylbenzoylphosphine oxide; quinone-based compounds such as 9,10-phenanthrenequinone, camphorquinone, or ethyl anthraquinone; borate-based compounds; carbazole-based compounds;2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(o-bromophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(o,p-dichlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetra(m-methoxyphenyl)benzimidazole, 2,2'-bis(o,o'-dichlorophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(o-nitrophenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(o-methylphenyl)-4,4',5,5'-tetraphenylbenzimidazole, 2,2'-bis(o-trifluorophenyl)-4,4',5,5'-tetraphenylbenzimidazole and other imidazole compounds; or titanocene compounds and the like. Among these, at least one compound selected from the group consisting of acetophenone compounds, phosphine compounds, imidazole compounds and oxime ester compounds is preferred, and oxime ester compounds are more preferred.

[0112] With respect to 100 parts by mass of the colorant (D), the content of the photopolymerization initiator (Y) is preferably 0.5 part by mass to 200 parts by mass, more preferably 1 part by mass to 100 parts by mass.

[0113] In addition, with respect to 100 parts by mass of the photopolymerization initiator (A), the content of the photopolymerization initiator (Y) is preferably 1 part by mass to 3000 parts by mass, more preferably 5 parts by mass to 2000 parts by mass. When contained in an appropriate amount, the pattern shape is further improved.

[0114] The photopolymerization initiator (Y) can be used alone or in combination of two or more.

[0115] In addition, when the photosensitive coloring composition contains the photopolymerization initiator (A') and the photopolymerization initiator (Y'), from the viewpoints of suppressing watermarks, pattern shape and residual film rate, with respect to 100 parts by mass of the total content of the photopolymerization initiator (A') and the photopolymerization initiator (Y'), the content of the photopolymerization initiator (Y') is preferably 5 parts by mass to 95 parts by mass, more preferably 25 parts by mass to 85 parts by mass.

[0116] From the viewpoints of suppressing watermarks, pattern shape and residual film rate of the film, with respect to 100 parts by mass of the photopolymerization initiator contained in the photosensitive coloring composition, the total content of the photopolymerization initiator (A') and the photopolymerization initiator (Y') is preferably 30 parts by mass or more, more preferably 30 parts by mass to 90 parts by mass, and particularly preferably 50 parts by mass to 80 parts by mass.

[0117] From the viewpoint of pattern shape, the photosensitive coloring composition preferably further contains a photopolymerization initiator (Z) different from the photopolymerization initiator (A') and the photopolymerization initiator (Y').

[0118] The photoinitiator (Z) is not particularly limited, and existing photoinitiators can be used. Specifically, examples include: acetophenone-based compounds exemplified by the photoinitiator (Y); benzophenone-based compounds; triazine-based compounds; acylphosphine oxide-based compounds; imidazole-based compounds, etc. Among these compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, and imidazole-based compounds are preferred, and from the viewpoint of the pattern shape, acetophenone-based compounds are more preferred.

[0119] As commercially available products of acetophenone-based compounds, examples include: "Omnirad 907" (2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one), "Omnirad 369" (2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-2-(benzyl)-1-butanone), "Omnirad 379EG" (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone) manufactured by IGM Resins; as commercially available products of acylphosphine oxide-based compounds, examples include: "Omnirad 819" (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide), "Omnirad TPO" (diphenyl-2,4,6-trimethylbenzoylphosphine oxide), etc. manufactured by IGM Resins.

[0120] The photoinitiator (Z) can be used alone or in combination of two or more.

[0121] [Binder resin (B)]

[0122] The binder resin (B) is a resin having a transmittance of 80% or more in the entire wavelength region of 400 nm to 700 nm when forming a film with a thickness of 2 μm. In addition, the transmittance is preferably 95% or more. The binder resin (B) is preferably an alkali-soluble resin. Thereby, the film formed from the photosensitive coloring composition can be patterned by photolithography. In addition, the binder resin (B) may have a thermosetting group. Examples of the thermosetting group include an epoxy group, an oxetanyl group, etc.

[0123] (Alkali-soluble resin)

[0124] Existing resins can be used as the alkali-soluble resin. For example, an alkali-soluble resin selected from the following (I), (II), and (III) and having a carboxyl group and a polymerizable unsaturated group in the side chain is preferred. Thereby, the photocurability of the film is improved.

[0125] (I) It is formed by reacting a polybasic acid or polybasic anhydride, and the reaction product of the epoxy group in the polymer having an epoxy group with a monomer having a carboxyl group, and further contains a base-soluble resin having a polycyclic alicyclic monomer unit (hereinafter referred to as base-soluble resin (I)).

[0126] (II) It is the reaction product of the carboxyl group in the polymer having a carboxyl group with a monomer having an epoxy group, and further contains a base-soluble resin having a polycyclic alicyclic monomer unit (hereinafter referred to as base-soluble resin (II)).

[0127] (III) It is a base-soluble resin which is the reaction product of the hydroxyl group in the polymer having a hydroxyl group and a carboxyl group with a monomer having an isocyanate group (hereinafter referred to as base-soluble resin (III)).

[0128] [Base-soluble resin (I)]

[0129] As an example of the production method of base-soluble resin (I), first, a polymer of a monomer having an epoxy group and other monomers is synthesized. In addition, the other monomers contain one or more polycyclic alicyclic monomers. Then, a monomer having a single carboxyl group is added to the epoxy group of the polymer, and the polybasic anhydride is reacted with the generated hydroxyl group to obtain a base-soluble photosensitive resin. In addition, the monomer having a single carboxyl group is a monomer having one carboxyl group.

[0130] [Base-soluble resin (II)]

[0131] As an example of the production method of base-soluble resin (II), first, a polymer of a monomer having a carboxyl group and other monomers is synthesized. In addition, the other monomers contain one or more polycyclic alicyclic monomers. Then, by adding a monomer having an epoxy group in an amount less than the amount of the carboxyl group to the carboxyl group of the polymer, a base-soluble photosensitive resin can be obtained.

[0132] Examples of the monomer having an epoxy group include glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidyloxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate. Among these, from the viewpoint of reactivity, glycidyl (meth)acrylate is preferred.

[0133] Examples of the monomer having a single carboxyl group include monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, α-haloalkyl, alkoxy, halogen, nitro, and cyano substituents of (meth)acrylic acid.

[0134] Examples of the polybasic acid anhydride include aromatic and alicyclic acid anhydrides such as tetrahydrophthalic anhydride, phthalic anhydride, and hexahydrophthalic anhydride; fatty acid anhydrides such as succinic anhydride and maleic anhydride; phosphoric anhydride, sulfonic anhydride, and the like. In addition, the polybasic acid anhydride may have a carboxyl group that does not form an acid anhydride.

[0135] Examples of other monomers include (meth)acrylic acid esters such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenoxyethyl (meth)acrylate, 1-adamantyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, or ethoxypolyethylene glycol (meth)acrylate; (meth)acrylamides such as (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, or acryloylmorpholine; styrenes such as styrene or α-methylstyrene; vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether; and fatty acid vinyl esters such as vinyl acetate or vinyl propionate.

[0136] Among them, polycyclic alicyclic monomers are preferred, and monomers containing the following formula (a) and / or formula (b) are more preferred.

[0137]

[0138]

[0139] In addition, the following can be enumerated: cyclohexyl maleimide, phenyl maleimide, methyl maleimide, ethyl maleimide, 1,2-bismaleimide ethane, 1,6-bismaleimide hexane, 3-maleimide propionic acid, 6,7-methylenedioxy-4-methyl-3-maleimide coumarin, 4,4'-bismaleimide diphenyl methane, bis(3-ethyl-5-methyl-4-maleimide phenyl) methane, N,N'-1,3-phenylene bismaleimide, N,N'-1,4-phenylene bismaleimide, N-(1-pyrenyl) maleimide, N-(2,4,6-trichlorophenyl) maleimide, N-(4-aminophenyl) maleimide, N-(4-nitrophenyl) maleimide, N-benzyl maleimide, N-bromomethyl-2,3-dichloromaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-3-maleimide propionate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide hexanoate, N-[4-(2-benzimidazolyl)phenyl] maleimide, 9-maleimide acridine and other N-substituted maleimide compounds; ethylene oxide (EO) modified cresol acrylate, n-nonylphenoxy polyethylene glycol acrylate, phenoxyethyl acrylate, ethoxylated phenyl acrylate, ethylene oxide (EO) modified (meth)acrylate of phenol, EO or propylene oxide (PO) modified (meth)acrylate of p-cumylphenol, EO modified (meth)acrylate of nonylphenol, PO modified (meth)acrylate of nonylphenol, etc.

[0140] [Alkali-soluble resin (III)]

[0141] As an example of the method for manufacturing the alkali-soluble resin (III), first, a monomer containing a hydroxyl group, a monomer containing a carboxyl group, and other monomers are polymerized to synthesize a polymer. Then, by reacting the isocyanate group of the monomer containing an isocyanate group with the hydroxyl group of the polymer, an alkali-soluble photosensitive resin can be obtained.

[0142] Examples of the hydroxyl group-containing monomer include: 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate or 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, or 4-hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, or cyclohexanedimethanol mono(meth)acrylate and other hydroxyalkyl methacrylates. In addition, examples include polyether mono(meth)acrylate formed by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide to (meth)acrylic acid hydroxyalkyl ester, polyester mono(meth)acrylate formed by addition polymerization of γ-valerolactone, ε-caprolactone, and / or 12-hydroxystearic acid, etc. Among these, 2-hydroxyethyl methacrylate and glycerol mono(meth)acrylate are preferred, and glycerol mono(meth)acrylate is more preferred.

[0143] Examples of the isocyanate group-containing monomer include: 2-(meth)acryloylethyl isocyanate, 2-(meth)acryloyloxyethyl isocyanate, or 1,1-bis〔methacryloyloxy〕ethyl isocyanate, etc.

[0144] In addition to the other monomers exemplified above, other monomers may also include monomers containing a phosphate group, etc. The monomer containing a phosphate group is, for example, a compound formed by reacting a phosphating agent such as phosphorus pentoxide or polyphosphoric acid with the hydroxyl group of a hydroxyl group-containing monomer.

[0145]

[0146] The binder resin (B) may contain an alkali-soluble resin (IV) other than the alkali-soluble resin (I), alkali-soluble resin (II), and alkali-soluble resin (III).

[0147] The alkali-soluble resin (IV) can be used alone or in combination of two or more.

[0148] Examples of the non-photosensitive alkali-soluble resin include: polyhydroxystyrene resin, polysiloxane resin, (meth)acrylic acid copolymer resin, styrene / maleic acid copolymer resin, α-olefin / (anhydrous) maleic acid copolymer resin, acrylamide resin, (meth)acrylic acid / acrylamide copolymer, etc., which have a group that promotes alkali dissolution in the resin. Among them, a copolymer with an ethylenically unsaturated monomer capable of copolymerizing with (meth)acrylic acid and styrene / styrene sulfonic acid copolymer are preferred. Specific examples of the group that promotes alkali dissolution include: carboxyl group, phosphate group, sulfonic acid group, hydroxyl group, phenolic hydroxyl group, etc., and the carboxyl group is preferred. These groups can be used alone or in combination of two or more.

[0149] ​From the viewpoint of developability, the weight average molecular weight (Mw) of the alkali-soluble resin is 2,000 to 40,000, preferably 3,000 to 30,000, more preferably 4,000 to 20,000. In addition, the value of Mw / Mn is preferably 10 or less. When the weight average molecular weight (Mw) is 2,000 or more, a decrease in adhesion to the substrate and difficulty in remaining the exposed pattern can be suppressed. When it is 40,000 or less, a decrease in alkali developability, generation of residues, and deterioration of the linearity of the pattern can be suppressed.

[0150] From the viewpoint of developability, the acid value of the alkali-soluble resin is preferably 50 (KOHmg / g) to 200 (KOHmg / g), more preferably 60 to 180, particularly preferably 70 to 170. When the acid value is 50 or more, a decrease in alkali developability, generation of residues, and deterioration of the linearity of the pattern can be suppressed. When it is 200 or less, a decrease in adhesion to the substrate and difficulty in remaining the exposed pattern can be suppressed.

[0151] The binder resin (B) can be used alone or in combination of two or more.

[0152] With respect to 100 parts by mass of the colorant (D), the content of the binder resin (B) is preferably 1 part by mass to 400 parts by mass, more preferably 1 part by mass to 300 parts by mass.

[0153] [Photopolymerizable compound (C)]

[0154] The photopolymerizable compound (C) is a compound having a polymerizable unsaturated group. The photopolymerizable compound (C) includes monomers and oligomers that are hardened by ultraviolet rays, heat, etc. to form a transparent resin. Examples of the photopolymerizable compound (C) include: polymerizable compounds having a structure derived from caprolactone, polymerizable compounds containing an acid group, polymerizable compounds containing a urethane bond, and other polymerizable compounds.

[0155] (Polymerizable compound (C-1) having a structure derived from caprolactone)

[0156] From the viewpoint of suppressing watermarks on the film, the photosensitive coloring composition preferably contains a polymerizable compound (C-1) having a caprolactone structure as the polymerizable compound (C).

[0157] The polymerizable compound (C-1) having a structure derived from caprolactone is not particularly limited as long as it has a structure derived from caprolactone in the molecule, and can be obtained by esterifying a polyol such as trimethylolethane, di-trimethylolethane, trimethylolpropane, di-trimethylolpropane, pentaerythritol, tripentaerythritol, glycerin, diglycerin, trimethylolmelamine, etc. with (meth)acrylic acid and ε-caprolactone. Among them, the compound represented by the following general formula (4) is preferred.

[0158] General formula (4)

[0159]

[0160] In the formula, all 6 Rs are groups represented by the following general formula (5), or 1 to 5 of the 6 Rs are groups represented by the following general formula (5), and the rest are groups represented by the following general formula (6).

[0161] General formula (5)

[0162]

[0163] In the formula, R 1 represents a hydrogen atom or a methyl group, m is a number of 1 or 2, and * is a bonding bond.

[0164] General formula (6)

[0165]

[0166] In the formula, R 1 represents a hydrogen atom or a methyl group, and * is a bonding bond.

[0167] Polymerizable compounds (C-1) having a structure derived from ε-caprolactone are commercially available, for example, as the KAYARAD DPCA series manufactured by Nippon Kayaku Co., Ltd., and examples include: DPCA-20 (in the general formulas (4) to (6), m = 1, the number of groups represented by the general formula (5) = 2, and all Rs 1 are hydrogen atoms), DPCA-30 (in the general formulas (4) to (6), m = 1, the number of groups represented by the general formula (5) = 3, and all Rs 1 are hydrogen atoms), DPCA-60 (in the general formulas (4) to (6), m = 1, the number of groups represented by the general formula (5) = 6, and all Rs 1 are hydrogen atoms), DPCA-120 (in the general formulas (4) to (6), m = 2, the number of groups represented by the general formula (5) = 6, and all Rs 1 are hydrogen atoms), etc.

[0168] From the viewpoint of suppressing watermarks on the film, the polymerizable compound (C-1) having a structure derived from ε-caprolactone is preferably a compound in which, in the general formulas (4) to (6), m = 1, the number of groups represented by the general formula (5) = 2 to 6, and all Rs 1 are hydrogen atoms, and more preferably a compound in which, in the general formulas (4) to (6), m = 1, the number of groups represented by the general formula (5) = 2 or 3, and all Rs 1 are hydrogen atoms.

[0169] In terms of suppressing the watermark of the film, with respect to 100 parts by mass of the polymeric compound (C), the content of the polymeric compound (C-1) having a structure of a source own lactone is preferably 5 to 80 parts by mass, more preferably 10 to 70 parts by mass, and particularly preferably 20 to 60 parts by mass.

[0170] (Polymeric compound (C-2) containing an acid group)

[0171] In terms of the pattern shape, the photosensitive coloring composition preferably contains a polymeric compound (C-2) containing an acid group. Examples of the acid group of the polymeric compound (C-2) containing an acid group include a sulfonic acid group, a carboxyl group, a phosphoric acid group, etc.

[0172] Examples of the polymeric compound (C-2) containing an acid group include: esters of polyols and (meth)acrylic acid poly(hydroxyalkyl)(meth)acrylates having free hydroxyl groups and dicarboxylic acids; esters of polycarboxylic acids and (meth)acrylic acid monohydroxyalkyl esters, etc. As specific examples, there can be mentioned: monohydroxyoligopolyacrylates or monohydroxyoligopoly(meth)acrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, etc. and monoesters having free carboxyl groups of dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, phthalic acid, etc.; oligomeric polyester compounds having free carboxyl groups of tricarboxylic acids such as propane-1,2,3-tricarboxylic acid (tricarballylic acid), butane-1,2,4-tricarboxylic acid, benzene-1,2,3-tricarboxylic acid, benzene-1,3,4-tricarboxylic acid, benzene-1,3,5-tricarboxylic acid, etc. and monohydroxy monoacrylates or monohydroxy monomethacrylates such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, etc.

[0173] Examples of commercially available products of the polymeric compound (C-2) containing an acid group include Viscoat #2500P manufactured by Osaka Organic Chemical Industry Co., Ltd., Aronix M-5300, Aronix M-5400, Aronix M-5700, Aronix M-510, Aronix M-520, Aronix M-521, etc. manufactured by Toagosei Co., Ltd.

[0174] In terms of the pattern shape, the content of the polymerizable compound (C-2) containing an acid group is preferably 20 to 80 parts by mass, more preferably 25 to 75 parts by mass, and still more preferably 35 to 70 parts by mass, relative to 100 parts by mass of the polymerizable compound (C).

[0175] (Polymerizable compound containing a urethane bond)

[0176] The polymerizable compound containing a urethane bond contains a urethane bond. Examples of the polymerizable compound containing a urethane bond include: polyfunctional urethane acrylate obtained by reacting a polyfunctional isocyanate with a (meth)acrylate having a hydroxyl group, polyfunctional urethane acrylate obtained by reacting a polyfunctional isocyanate with an alcohol and then reacting a (meth)acrylate having a hydroxyl group, and the like.

[0177] Examples of the (meth)acrylate having a hydroxyl group include: 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, di-trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene oxide-modified penta(meth)acrylate, dipentaerythritol propylene oxide-modified penta(meth)acrylate, dipentaerythritol caprolactone-modified penta(meth)acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, reaction product of an epoxy group-containing compound and a carboxy (meth)acrylate, polyol polyacrylate containing a hydroxyl group, and the like.

[0178] Examples of the polyfunctional isocyanate include: tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, isophorone diisocyanate, polyisocyanate, and the like.

[0179] (Other polymerizable compound (C-3))

[0180] Other polymerizable compounds include, for example: methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, phenoxy tetraethylene glycol (meth)acrylate, phenoxy hexaethylene glycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate, isocyanuric acid EO-modified tri(meth)acrylate, di-trimethylolpropane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecyl (meth)acrylate, (meth)acrylate of hydroxymethylated melamine, epoxy (meth)acrylate, urethane acrylate and other various acrylates and methacrylates, (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, acrylonitrile, etc.

[0181] Examples of commercially available products of these include: KAYARAD R-128H, KAYARAD R526, KAYARAD PEG400DA, KAYARAD MAND, KAYARAD NPGDA, KAYARAD R-167, KAYARAD HX-220, KAYARAD R-551, KAYARAD R712, KAYARAD R-604, KAYARAD R-684, KAYARAD GPO-303, KAYARAD TMPTA, KAYARAD DPHA, KAYARAD DPEA-12, KAYARAD DPHA-2C, KAYARAD D-310, KAYARAD D-330, manufactured by Nippon Kayaku Co., Ltd.; Aronix M-303, Aronix M-306, Aronix M-309, Aronix M-310, Aronix M-321, Aronix M-325, Aronix M-350, Aronix M-360, Aronix M-313, Aronix M-315, Aronix M-400, Aronix M-402, Aronix M-403, Aronix M-404, Aronix M-405, Aronix M-406, Aronix M-450, Aronix M-452, Aronix M-408, Aronix M-211B, Aronix M-101A, manufactured by Toagosei Co., Ltd.; Viscoat #310HP, Viscoat #335HP, Viscoat #700, Viscoat #295, Viscoat #330, Viscoat #360, Viscoat #GPT, Viscoat #400, Viscoat #405, Viscoat UV-4108F, Viscoat UV-4117F, manufactured by Osaka Organic Chemical Industry Ltd.; NK Ester A-9300, NK Ester UA-160TM, manufactured by Shin-Nakamura Chemical Co., Ltd.AH-600, AT-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G, DAUA-167, etc. manufactured by Kyoeisha Chemical Co., Ltd.

[0182] The photopolymerizable compound (C) can be used alone or in combination of two or more.

[0183] With respect to 100 parts by mass of the colorant (D), the content of the photopolymerizable compound (C) is preferably 5 to 300 parts by mass, more preferably 10 to 200 parts by mass.

[0184] The mass ratio [Ia / M] of the mass [Ia] of the photopolymerization initiator (A) to the mass [M] of the photopolymerizable compound (C) is preferably 0.01 to 3.00, more preferably 0.15 to 2.00.

[0185] In addition, when the photosensitive coloring composition contains a sensitizer (E) or a photopolymerization initiator (Y), the mass ratio [Ib / M] of the total mass [Ib] of the photopolymerization initiator (A), the sensitizer (E) and the photopolymerization initiator (Y) to the mass [M] of the photopolymerizable compound (C) is preferably 0.01 to 3.00, more preferably 0.15 to 2.00. By an appropriate mass ratio [Ia / M], the developability resistance, chemical resistance, pattern shape, linearity and resolution can be improved in a balanced manner.

[0186] [Colorant (D)]

[0187] Examples of the colorant (D) include organic pigments and inorganic pigments. The pigment is preferably a pigment with high color development and high heat resistance, and usually an organic pigment is preferred. In addition, the colorant (D) may contain a dye within the range that does not reduce the heat resistance.

[0188] (Pigment)

[0189] Hereinafter, specific examples of organic pigments are represented by color index numbers. As red pigments, for example, the following can be cited: C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 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, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 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, the pigments described in Japanese Patent Laid-Open No. 2014-134712, the pigments described in Japanese Patent No. 6368844, etc. Among these, from the viewpoints of heat resistance, light resistance, and transmittance in the filter section, C.I. Pigment Red 48:1, 122, 177, 224, 242, 269, 254, 291, 295, 296, the pigments described in Japanese Patent Laid-Open No. 2014-134712, and the pigments described in Japanese Patent No. 6368844 are preferred, and C.I. Pigment Red 177, 254, 291, 295, 296, the pigments described in Japanese Patent Laid-Open No. 2014-134712, and the pigments described in Japanese Patent No. 6368844 are more preferred.

[0190] In addition, as the red pigment, C.I. Pigment Orange 36, 38, 43, 51, 55, 59, 61, 64, 71, 73 or other orange pigments or yellow pigments may also be used in combination.

[0191] Examples of the blue pigment include C.I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like. Among these, from the viewpoints of heat resistance, light resistance and transmittance in the light filtering section, C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4 or 15:6 is preferred, and C.I. Pigment Blue 15:6 is more preferred. In addition, a purple pigment may be used in combination with the blue pigment.

[0192] Examples of the purple pigment include C.I. 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 and the like. Among these, from the viewpoints of heat resistance, light resistance and transmittance in the light filtering section, C.I. Pigment Violet 19 or 23 is preferred, and C.I. Pigment Violet 23 is more preferred.

[0193] Examples of the green pigment include C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, 63, the pigment described in Japanese Patent Laid-Open No. 2017-111398 and the like. Among these, from the viewpoint of transmittance, C.I. Pigment Green 36, 58, 59, 62, 63, the pigment described in Japanese Patent Laid-Open No. 2017-111398 is preferred.

[0194] As yellow pigments, for example, the following can be mentioned: C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, 233, pigments described in Japanese Patent Laid-Open No. 2012-226110, etc. Preferably, C.I. Pigment Yellow 138, 139, 150, 185, 231, 233, and pigments described in Japanese Patent Laid-Open No. 2012-226110 are used.

[0195] As cyan coloring compositions, for example, the following can be mentioned: blue pigments such as C.I. Pigment Blue 15:1, 15:2, 15:4, 15:3, 15:6, 16, 81, etc.

[0196] As magenta coloring compositions, for example, the following can be mentioned: purple pigments and red pigments such as C.I. Pigment Violet 1, 19, C.I. Pigment Red 144, 146, 177, 169, 81, etc. The magenta composition can be used in combination with yellow pigments.

[0197] As inorganic pigments, for example, the following can be mentioned: titanium oxide, barium sulfate, zinc white, lead sulfate, chrome yellow, zinc yellow, iron oxide red (red iron(III) oxide), cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green, umber, synthetic iron black, etc.

[0198] The black photosensitive coloring composition for forming a black matrix is preferably, for example, one containing carbon black, aniline black, anthraquinone-based black pigments, perylene-based black pigments, and specifically, examples thereof include C.I. Pigment Black 1, 6, 7, 12, 20, 31, etc. In addition, the black photosensitive coloring composition may be mixed with red pigments, blue pigments, and green pigments. From the viewpoints of low cost and light-shielding property, carbon black is preferred. Carbon black may also be surface-treated with a resin or the like. In addition, in order to adjust the hue, a blue pigment and a purple pigment may be used in combination in the black photosensitive coloring composition.

[0199] (Dye)

[0200] Examples of dyes include: acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, sulfur dyes, etc. In addition, derivatives of dyes, or lake pigments obtained by lake-forming dyes, etc. may also be used.

[0201] In addition, examples of dyes include: acid dyes having acidic groups such as sulfonic acid groups or carboxylic acid groups, or inorganic salts of acid dyes and salt-forming compounds of quaternary ammonium salt compounds, tertiary amine compounds, secondary amine compounds, or primary amine compounds; salt-forming compounds of resin components having these amino groups and acid dyes, etc. Salt-forming compounds of acid dyes and compounds having an onium group are also preferred because of their excellent fastness. In addition, as the compound having an onium group, a resin having a cationic group in the side chain is preferred.

[0202] Examples of basic dyes include salt-forming compounds with organic acids, or perchloric acid, or metal salts thereof. Among them, salt-forming compounds of basic dyes are preferred because of their excellent resistance and compatibility with pigments. Furthermore, it is more preferably to use salt-forming compounds obtained by forming salts of basic dyes and counter components that act as counter ions, namely, organic sulfonic acids, organic sulfuric acids, fluorine-containing phosphorus anion compounds, fluorine-containing boron anion compounds, cyano-containing nitrogen anion compounds, anion compounds containing the conjugate base of an organic acid having a halogenated hydrocarbon group, or acid dyes.

[0203] In addition, when a polymerizable unsaturated group is present in the pigment skeleton, a dye with excellent resistance can be obtained, so it is preferred.

[0204] Examples of the chemical structure of the dye include azo dyes, bisazo dyes, azomethine dyes (such as indoaniline dyes and indophenol dyes), dipyrromethene dyes, quinone dyes (such as benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, and anthrapyridone dyes), carbonium dyes (such as diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, and acridine dyes), quinoneimine dyes (such as oxazine dyes and thiazine dyes), azine dyes, polymethine dyes (such as oxacarbocyanine dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, and croconium dyes), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, etc. Among these, from the viewpoints of color characteristics such as hue, color separation property, and color unevenness, azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes are preferred, and xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are more preferred. Specific structures of the dyes are described in "New Edition Dye Handbook" (edited by the Organic Synthetic Chemistry Association; Maruzen, 1970), "Colour Index" (The Society of Dyers and Colourists), "Pigment Handbook" (edited by Ohkawara et al.; Kodansha, 1986), etc.

[0205] The colorant (D) can be used alone or in combination of two or more.

[0206] In 100% by mass of the non-volatile components of the photosensitive coloring composition, the content of the colorant (D) is preferably 5% to 70% by mass, more preferably 10% to 60% by mass. When the content of the colorant (D) is 5% by mass or more, the color reproducibility in the use of color filters is improved, and when it is 70% by mass or less, the sensitivity or pattern formability is further improved.

[0207] (Micronization of pigments)

[0208] In the case of using an organic pigment in the colorant (D), it is preferably mixed with other raw materials after being subjected to a micronization treatment. As methods of the micronization treatment, for example, wet grinding, dry grinding, dissolution precipitation method, etc. can be cited. Among these, a salt milling treatment using a kneader method which is a kind of wet grinding is preferably used. The average primary particle diameter of the organic pigment after the micronization treatment is preferably 5 nm to 90 nm, more preferably 10 nm to 80 nm, still more preferably 10 nm to 70 nm, and particularly preferably 15 nm to 70 nm. With an appropriate particle diameter, the dispersibility is further improved and the contrast ratio of the film is further improved. In addition, the average primary particle diameter is the average value of about 20 particles arbitrarily selected from the magnified image of a transmission electron microscope (TEM). In addition, in the case where there are the longitudinal axis length and the transverse axis length of the particle, the longitudinal axis length is used.

[0209] The so-called salt milling treatment refers to the following treatment: using a batch or continuous mixer such as a kneader, a two-rod roll mill, a three-rod roll mill, a ball mill, an attritor, a sand mill, a planetary mixer, etc., while heating a mixture of a pigment, a water-soluble inorganic salt and a water-soluble organic solvent, mechanically kneading it, and then removing the water-soluble inorganic salt and the water-soluble organic solvent by water washing. The water-soluble inorganic salt functions as a crushing aid, and the pigment is crushed by utilizing the high hardness of the inorganic salt during salt milling. By optimizing the conditions for the salt milling treatment of the pigment, a pigment with a very fine primary particle diameter, a narrow distribution range and a sharp particle size distribution can be obtained.

[0210] Examples of the water-soluble inorganic salt include sodium chloride, potassium chloride, sodium sulfate, etc. Among these, from the viewpoint of price, sodium chloride (table salt) is preferably used. From the viewpoints of treatment efficiency and production efficiency, the usage amount of the water-soluble inorganic salt is preferably 50 parts by mass to 2000 parts by mass, more preferably 300 parts by mass to 1000 parts by mass with respect to 100 parts by mass of the pigment.

[0211] The water-soluble organic solvent wets the pigment and the water-soluble inorganic salt. The water-soluble organic solvent is a compound that dissolves (mixes) in water and substantially does not dissolve the water-soluble inorganic salt. From the viewpoint of being less likely to volatilize due to the temperature rise during salt milling, the water-soluble organic solvent is preferably a high-boiling solvent having a boiling point of 120 °C or higher. Examples of the water-soluble organic solvent include 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. The amount of the water-soluble organic solvent used is preferably 5 to 1000 parts by mass, more preferably 50 to 500 parts by mass, relative to 100 parts by mass of the pigment.

[0212] When performing salt milling treatment, a resin may be added as needed. Examples of the resin include natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, etc. The resin is preferably solid at room temperature and water-insoluble, and more preferably partially soluble in the water-soluble organic solvent. The amount of the resin used is preferably 5 to 200 parts by mass relative to 100 parts by mass of the pigment.

[0213] (Dispersant)

[0214] The dispersant is used to uniformly disperse the pigment in the dispersion medium and stably maintain its state, and generally a pigment derivative or a resin-type dispersant, etc. is used.

[0215] [Pigment derivative]

[0216] The pigment derivative adsorbs on the surface of the organic pigment, making the surface of the organic pigment polar, so that it is easy to be affinity with the binder resin (B) and the resin-type dispersant described later, etc., thereby further improving the dispersibility of the organic pigment. The pigment derivative is a compound having an acidic group, a basic group, a neutral group, etc. in the organic pigment residue. Examples of the pigment derivative include compounds having acidic substituents such as a sulfo group, a carboxyl group, or a phosphoric acid group and amine salts thereof; compounds having basic substituents such as a sulfonamide group or a tertiary amino group at the end; compounds having neutral substituents such as a phenyl group or a phthalimidoalkyl group. Examples of the organic pigment include diketopyrrolopyrrole-based pigments, anthraquinone-based pigments, quinacridone-based pigments, dioxazine-based pigments, perinone-based pigments, perylene-based pigments, thiazine indigo-based pigments, triazine-based pigments, benzimidazolone-based pigments, indole-based pigments such as benzisoindole; isoindoline-based pigments, isoindolinone-based pigments, quinophthalone-based pigments, naphthol-based pigments, vat-based pigments, metal complex-based pigments, azo-based pigments such as azo, bisazo, and polyazo, etc.

[0217] Specifically, the following existing pigment derivatives described in the following gazettes, etc. can be cited. As diketopyrrolopyrrole-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 2001-220520, International Publication No. 2009 / 081930, International Publication No. 2011 / 052617, International Publication No. 2012 / 102399, Japanese Patent Laid-Open No. 2017-156397; as phthalocyanine-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 2007-226161, International Publication No. 2016 / 163351, Japanese Patent Laid-Open No. 2017-165820, Japanese Patent No. 5753266; as anthraquinone-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 63-264674, Japanese Patent Laid-Open No. 09-272812, Japanese Patent Laid-Open No. 10-245501, Japanese Patent Laid-Open No. 10-265697, Japanese Patent Laid-Open No. 2007-079094, International Publication No. 2009 / 025325; as quinacridone-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 48-54128, Japanese Patent Laid-Open No. 03-9961, Japanese Patent Laid-Open No. 2000-273383; as dioxazine-based pigment derivatives, Japanese Patent Laid-Open No. 2011-162662 can be cited; as thiazine indigo-based pigment derivatives, Japanese Patent Laid-Open No. 2007-314785 can be cited; as triazine-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 61-246261, Japanese Patent Laid-Open No. 11-199796, Japanese Patent Laid-Open No. 2003-165922, Japanese Patent Laid-Open No. 2003-168208, Japanese Patent Laid-Open No. 2004-217842, Japanese Patent Laid-Open No. 2007-314681; as benzisoindole-based pigment derivatives, Japanese Patent Laid-Open No. 2009-57478 can be cited; as quinophthalone-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 2003-167112, Japanese Patent Laid-Open No. 2006-291194, Japanese Patent Laid-Open No. 2008-31281, Japanese Patent Laid-Open No. 2012-226110; as naphthol-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 2012-208329, Japanese Patent Laid-Open No. 2014-5439; as azo-based pigment derivatives, the following can be cited: Japanese Patent Laid-Open No. 2001-172520, Japanese Patent Laid-Open No. 2012-172092; as acidic substituents, Japanese Patent Laid-Open No. 2004-307854 can be cited;Examples of the basic substituent include Japanese Patent Laid-Open No. 2002-201377, Japanese Patent Laid-Open No. 2003-171594, Japanese Patent Laid-Open No. 2005-181383, and Japanese Patent Laid-Open No. 2005-213404. In addition, in these documents, the pigment derivative is sometimes described as a derivative, a pigment derivative, a dispersant, a pigment dispersant, or simply as a compound, etc. However, a compound having a substituent such as an acidic group, a basic group, or a neutral group in the organic pigment residue described above has the same meaning as the pigment derivative.;

[0218] The pigment derivative can be used alone or in combination of two or more.

[0219] With respect to 100 parts by mass of the colorant (D), the content of the pigment derivative is preferably 1 part by mass to 100 parts by mass, more preferably 3 parts by mass to 70 parts by mass, still more preferably 5 parts by mass to 50 parts by mass. For example, it can be 1 part by mass to 15 parts by mass or 2 parts by mass to 10 parts by mass.

[0220] By adding a pigment derivative to a pigment and performing, for example, micronization treatments such as acid pasting, acid slurry, dry grinding, salt grinding, and solvent salt grinding, the pigment derivative is adsorbed on the surface of the pigment. Compared with the case where no pigment derivative is added, the primary particles of the pigment can be made finer.

[0221] [Resin-type dispersant]

[0222] The resin-type dispersant has: a colorant affinity site that adsorbs to the colorant (D); and a site that has a high affinity for components other than the colorant and alleviates the steric repulsion between dispersed particles. There is no particular limitation on the resin-type dispersant, and existing resin-type dispersants can be used. Examples of the resin-type dispersant in terms of resin type include: urethane-based dispersants such as polyurethane; polycarboxylic esters such as polyacrylate, unsaturated polyamides, polycarboxylic acids, (partial) amine salts of polycarboxylic acids, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl-containing polycarboxylic esters, and modified products thereof; oil-based dispersants such as amides and their salts formed by the reaction of poly(lower alkyleneimine) and a polyester having a free carboxyl group; water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, and polyvinylpyrrolidone; polyester-based, modified polyacrylate-based, ethylene oxide / propylene oxide adduct compounds, phosphate ester-based, etc.

[0223] From the viewpoint of dispersion stability, it is preferably a base (hereinafter referred to as an adsorption base) adsorbed on the colorant. As the adsorption base, a resin having a cationic group and / or an anionic group is preferred.

[0224] There is no particular limitation on the resin having a cationic group, and existing resins can be used. Specifically, as the cationic group, groups containing a nitrogen atom such as a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium salt group, and a nitrogen-containing heterocycle can be cited.

[0225] There is no particular limitation on the resin having an anionic group, and existing resins can be used. Specifically, as the anionic group, a carboxyl group, a phosphoric acid group, a sulfonic acid group, etc. can be cited. Among them, from the viewpoint of the adsorption property to the colorant, a carboxyl group and a phosphoric acid group are preferred.

[0226] Regarding the structure of the resin-type dispersant, there is no particular limitation, and a random structure, a block structure, a graft structure, a comb structure, a star structure, etc. can be cited. Among them, from the viewpoint of dispersion stability, a block structure or a comb structure is preferred.

[0227] As resin dispersants that can be used in photosensitive coloring compositions, specifically, the following can be cited: Disperbyk-101, Disperbyk-103, Disperbyk-107, Disperbyk-108, Disperbyk-110, Disperbyk-111, Disperbyk-116, Disperbyk-130, Disperbyk-140, Disperbyk-154, Disperbyk-161, Disperbyk-162, Disperbyk-163, Disperbyk-164, Disperbyk-165, Disperbyk-166, Disperbyk-167, Disperbyk-168, Disperbyk-170, Disperbyk-171, Disperbyk-174, Disperbyk-180, Disperbyk-181, Disperbyk-182, Disperbyk-183, Disperbyk-184, Disperbyk-185, Disperbyk-190, Disperbyk-2000, Disperbyk-2001, Disperbyk-2009, Disperbyk-2010, Disperbyk-2020, Disperbyk-2025, Disperbyk-2050, Disperbyk-2070, Disperbyk-2095, Disperbyk-2150, Disperbyk-2155, Disperbyk-2163, Disperbyk-2164, manufactured by BYK-Chemie Japan; or Anti-Terra-U203, Anti-Terra-U204; or BYK-P104, BYK-P104S,BYK-220S, Lactimon, Lactimon-WS, Bykumen, etc., SOLSPERSE-3000, SOLSPERSE-9000, SOLSPERSE-13000, SOLSPERSE-13240, SOLSPERSE-13650, SOLSPERSE-13940, SOLSPERSE-16000, SOLSPERSE-17000, SOLSPERSE-18000, SOLSPERSE-20000, SOLSPERSE-21000, SOLSPERSE-24000, SOLSPERSE-26000, SOLSPERSE-27000, SOLSPERSE-28000, SOLSPERSE-31845, SOLSPERSE-32000, SOLSPERSE-32500, SOLSPERSE-32550, SOLSPERSE-33500, SOLSPERSE-32600, SOLSPERSE-34750, SOLSPERSE-35100, SOLSPERSE-36600, SOLSPERSE-38500, SOLSPERSE-41000, SOLSPERSE-41090, SOLSPERSE-53095, SOLSPERSE-55000, SOLSPERSE-56000, SOLSPERSE-76500, etc., manufactured by Lubrizol Corporation in Japan; EFKA-46, EFKA-47, EFKA-48, EFKA-452, EFKA-4008, EFKA-4009, EFKA-4010, EFKA-4015, EFKA-4020, EFKA-4047, EFKA-4050, EFKA-4055, EFKA-4060, EFKA-4080, EFKA-4400, manufactured by BASF CorporationEfka - 4401, Efka - 4402, Efka - 4403, Efka - 4406, Efka - 4408, Efka - 4300, Efka - 4310, Efka - 4320, Efka - 4330, Efka - 4340, Efka - 450, Efka - 451, Efka - 453, Efka - 4540, Efka - 4550, Efka - 4560, Efka - 4800, Efka - 5010, Efka - 5065, Efka - 5066, Efka - 5070, Efka - 7500, Efka - 7554, Efka - 1101, Efka - 120, Efka - 150, Efka - 1501, Efka - 1502, Efka - 1503, etc., Ajisper PA111, Ajisper PB711, Ajisper PB821, Ajisper PB822, Ajisper PB824, etc. manufactured by Ajinomoto Fine - Techno Co., Ltd., and resin - type dispersants described in Japanese Patent Laid - Open No. 2008 - 029901, Japanese Patent Laid - Open No. 2009 - 155406, Japanese Patent Laid - Open No. 2010 - 185934, Japanese Patent Laid - Open No. 2011 - 157416, etc. These resin - type dispersants can be used alone or in combination of two or more.

[0228] In addition, in terms of the types of functional groups, resin - type dispersants include resin - type dispersants containing acidic functional groups and resin - type dispersants containing basic functional groups. The resin - type dispersants containing acidic functional groups are preferably, for example, resin - type dispersants having an aromatic carboxylic acid structure, such as those described in International Publication No. 2008 / 007776, Japanese Patent Laid - Open No. 2008 - 029901, Japanese Patent Laid - Open No. 2009 - 155406, Japanese Patent Laid - Open No. 2010 - 185934, Japanese Patent Laid - Open No. 2011 - 157416, Japanese Patent Laid - Open No. 2009 - 251481, Japanese Patent Laid - Open No. 2007 - 23195, Japanese Patent Laid - Open No. 1996 - 143651, etc.

[0229] Examples of the resin-type dispersant containing an alkaline functional group include: a graft copolymer containing a nitrogen atom, and an acrylic block copolymer and a urethane-based polymer dispersant containing a nitrogen atom, which have a functional group such as a tertiary amino group, a quaternary ammonium salt group, and a nitrogen-containing heterocycle in the side chain. In addition, a resin-type dispersant containing an acidic functional group and a resin-type dispersant containing an alkaline functional group may be used in combination.

[0230] The dispersant may be used alone or in combination of two or more.

[0231] With respect to 100 parts by mass of the colorant (D), the content of the dispersant is preferably 3 parts by mass to 200 parts by mass, more preferably 5 parts by mass to 100 parts by mass.

[0232] [Sensitizer (E)]

[0233] From the viewpoints of reactivity and pattern shape, the photosensitive coloring composition preferably contains a sensitizer (E). The sensitizer (E) is more preferably used in combination with the polymerization initiator (C-3). The sensitizer (E) is not particularly limited, and existing sensitizers can be used.

[0234] Examples of the sensitizer (E) include: unsaturated ketones represented by chalcone derivatives or dibenzalacetone; 1,2-diketone derivatives represented by benzil and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalinoporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyranylium derivatives, thiopyrylium derivatives, tetraphyrin derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, Michler's ketone derivatives, benzophenone derivatives and the like. Among these, thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives are preferred. Specific examples of the sensitizer (E) include: 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, α-acyloxy esters, acylphosphine oxides, methyl benzoylformate, benzil, 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4'-diethyl isophthalophenone, 3,3'-tetra(tert-butylperoxycarbonyl)benzophenone or 4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, 2-aminobenzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzoyl-N-ethylcarbazole and the like. Among these, from the viewpoint of the pattern shape, thioxanthone derivatives and benzophenone derivatives are preferred.

[0235] The sensitizer (E) can be used alone or in combination of two or more.

[0236] From the viewpoint of achieving both suppression of watermark and pattern shape, the content of the sensitizer (E) is preferably 1 to 200 parts by mass, 3 to 60 parts by mass, or 5 to 50 parts by mass, based on 100 parts by mass of the photopolymerization initiator (A).

[0237] [Multifunctional thiol (F)]

[0238] The photosensitive coloring composition may contain a polyfunctional thiol (F). The polyfunctional thiol (F) is a compound having two or more thiol (SH) groups, more preferably having four or more SH groups. When the number of functional groups increases, light curing from the surface of the film to the deepest part becomes easier. The polyfunctional thiol (F) acts as a chain transfer agent in the free radical polymerization process after light irradiation by being used in combination with a photopolymerization initiator (A), and produces thiyl radicals (thiyl radicals) that are not easily hindered by polymerization caused by oxygen, so it becomes highly sensitive. Particularly preferred are polyfunctional aliphatic thiols in which the SH group is bonded to an aliphatic group such as a methylene group or an ethylene group.

[0239] Examples of the polyfunctional thiol (F) include hexane dithiol, decanedithiol, 1,4-butanediol dithiopropionate, 1,4-butanediol dithioglycolate, ethylene glycol dithioglycolate, ethylene glycol dithiopropionate, trimethylolpropane trithioglycolate, trimethylolpropane trithiopropionate, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrathioglycolate, pentaerythritol tetrathiopropionate, trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, and 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine. Preferred examples include ethylene glycol dithiopropionate, trimethylolpropane trithiopropionate, and pentaerythritol tetrathiopropionate.

[0240] The polyfunctional thiol (F) can be used alone or in combination of two or more.

[0241] The content of the polyfunctional thiol (F) is preferably 0.05 to 100 parts by mass, more preferably 1.0 to 50.0 parts by mass, relative to 100 parts by mass of the colorant (D). When the content of the polyfunctional thiol (F) is 0.05 parts by mass or more, crosslinking of the film after light irradiation is promoted, and in addition to improving the development resistance, watermarks of the film can be further suppressed.

[0242] The content of the polyfunctional thiol (F) is preferably 1 to 10% by mass, more preferably 2 to 8% by mass, relative to 100% by mass of the nonvolatile components of the photosensitive coloring composition. When an appropriate amount is contained, the photosensitivity is improved and wrinkles are less likely to occur on the film surface.

[0243] [Thermosetting compound (G)]

[0244] The photosensitive coloring composition may contain a thermosetting compound (G). Thereby, the thermosetting compound (G) is thermoset in the post-baking process to increase the crosslinking density of the film and improve the heat resistance. In addition, aggregation of the colorant (D) in the post-baking process is suppressed, and the contrast ratio is improved. The thermosetting compound (G) may be a low-molecular compound or a high-molecular compound such as a resin.

[0245] Examples of the thermosetting compound (G) include: epoxy compounds, oxetane compounds, benzoguanamine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds, urea compounds, and phenol compounds. Among these, epoxy compounds and oxetane compounds are preferred.

[0246] (Epoxy compound)

[0247] The epoxy compound may be a low-molecular compound or a high-molecular compound such as a resin. Examples of the epoxy compound include: bisphenols (bisphenol A, bisphenol F, bisphenol S, bisphenol, bisphenol AD, etc.), phenols (phenol, alkyl-substituted phenols, aromatic-substituted phenols, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) and condensates with various aldehydes (formaldehyde, acetaldehyde, alkyl aldehydes, benzaldehyde, alkyl-substituted benzaldehydes, hydroxybenzaldehydes, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.); polymers of phenols and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.); condensates of phenols and ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.); condensates of phenols and aromatic dimethyl alcohols (xylene glycol, α,α,α',α'-xylene glycol, biphenyl dimethanol, α,α,α',α'-biphenyl dimethanol, etc.); condensates of phenols and aromatic dichloromethyl compounds (α,α'-dichloroxylene, dichloromethyl biphenyl, etc.); condensates of bisphenols and various aldehydes; glycidyl ether-based epoxy resins, alicyclic epoxy resins, heterocyclic epoxy resins, aliphatic epoxy resins, glycidylamine-based epoxy resins, glycidyl ester-based epoxy resins, etc. obtained by glycidylating alcohols, etc.

[0248] Examples of commercially available products include: EPICOAT 807, EPICOAT 815, EPICOAT 825, EPICOAT 827, EPICOAT 828, EPICOAT 190P, EPICOAT 191P (the above are product names; manufactured by Yuka Shell Epoxy Co., Ltd.), EPICOAT 1004, EPICOAT 1256 (the above are product names; manufactured by Nippon Epoxy Resins Co., Ltd.), TECHMORE VG3101L (product name; manufactured by Mitsui Chemicals, Inc.), EPPN-501H, EPPN-502H (product names; manufactured by Nippon Kayaku Co., Ltd.), JER 1032H60 (product name; manufactured by Nippon Epoxy Resins Co., Ltd.), JER 157S65, JER 157S70 (product names; manufactured by Nippon Epoxy Resins Co., Ltd.), EPPN-201 (product name; manufactured by Nippon Kayaku Co., Ltd.), JER152, JER154 (the above are product names; manufactured by Nippon Epoxy Resins Co., Ltd.), EOCN-102S, EOCN-103S, EOCN-104S, EOCN-1020 (the above are product names; manufactured by Nippon Kayaku Co., Ltd.), CELLOXIDE 2021, EHPE-3150 (the above are product names; manufactured by Daicel Chemical Industries, Ltd.), DENACOL EX-211, DENACOL EX-212, DENACOL EX-252, DENACOL EX-313, DENACOL EX-314, DENACOL EX-321, DENACOL EX-411, DENACOL EX-421, DENACOL EX-512, DENACOL EX-521, DENACOL EX-611, DENACOL EX-612, DENACOL EX-614, DENACOL EX-614B, DENACOL EX-622, DENACOL EX-711, DENACOL EX-721 (the above are product names; manufactured by Nagase ChemteX Corporation), TEPIC-L, TEPIC-H, TEPIC-S (manufactured by Nissan Chemical Industries, Ltd.), etc.

[0249] With respect to 100 parts by mass of the colorant (A), the content of the epoxy compound is preferably from 0.5 part by mass to 300 parts by mass, more preferably from 1.0 part by mass to 50 parts by mass. When appropriately formulated, the contrast ratio and heat resistance are improved.

[0250] (oxetane compound)

[0251] The oxetane compound is an existing compound having an oxetanyl group. Examples of the oxetane compound include monofunctional oxetane compounds, difunctional oxetane compounds, and oxetane compounds having trifunctional or more.

[0252] Examples of the monofunctional oxetane compound include: (3-ethyloxetan-3-yl)methyl acrylate, (3-ethyloxetan-3-yl)methyl methacrylate, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 3-ethyl-3-(2-methacryloyloxymethyl)oxetane, 3-ethyl-3-{[3-(triethoxysilyl)propoxy]methyl}oxetane, and the like.

[0253] As specific examples, OXE-10 and OXE-30 manufactured by Osaka Organic Chemical Industry Co., Ltd., OXT-101 and OXT-212 manufactured by Toagosei Co., Ltd., and the like can be cited.

[0254] Examples of the difunctional oxetane compound include: 4,4'-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl, 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 1,4-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}benzene, bis[1-ethyl(3-oxetanyl)]methyl ether, bis[1-ethyl(3-oxetanyl)]methyl ether-3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(2-phenoxymethyl)oxetane, 3,7-bis(3-oxetanyl)-5-oxa-nonane, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, dicyclopentenyl bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis(3-ethyl-3-oxetanylmethoxy)butane, 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, polyethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, ethylene oxide (EO)-modified bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, propylene oxide (PO)-modified bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, EO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, PO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, EO-modified bisphenol F (3-ethyl-3-oxetanylmethyl)ether, etc.

[0255] As specific examples, there may be mentioned OXBP and OXTP manufactured by Ube Industries, Ltd., and OXT-121 and OXT-221 manufactured by Toagosei Co., Ltd.

[0256] Examples of trifunctional or higher oxetane compounds include: pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol hexa(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol penta(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetra(3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol hexa(3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol penta(3-ethyl-3-oxetanylmethyl) ether, di-trimethylolpropane tetra(3-ethyl-3-oxetanylmethyl) ether, and polymers obtained by radical polymerization of a resin containing an oxetanyl group (e.g., an oxetane-modified phenol novolak resin described in Japanese Patent No. 3783462) or a (meth)acrylic monomer such as the OXE-30.

[0257] With respect to 100 parts by mass of the non-volatile components of the photosensitive coloring composition, the content of the oxetane compound is preferably 0.5 parts by mass to 50 parts by mass, more preferably 1 part by mass to 40 parts by mass. When the content of the oxetane compound is within the above range, an excellent coating film with good watermark and high chemical resistance can be obtained, so it is preferred.

[0258] The melamine compound refers to a compound having a melamine ring structure. The melamine compound can be a low-molecular compound or a high-molecular compound such as a resin. In the present invention, a hydroxymethyl type or an ether type, and a melamine compound having an average of 5.0 or more hydroxymethyl groups and / or ether groups per melamine ring are preferred. If the average number of hydroxymethyl groups and / or ether groups per melamine ring is less than 5.0, the number of reaction points is small, and the crosslinked structure during hardening cannot be sufficiently dense. Therefore, the effect of suppressing the decrease in the contrast ratio or improving the N-methylpyrrolidone resistance by the heat treatment step sometimes becomes small.

[0259] Examples of commercially available products include: NIKALAC MW-30HM, NIKALAC MW-390, NIKALAC MW-100LM, NIKALAC MX-750LM, NIKALAC MW-30M, NIKALAC MW-30, NIKALAC MW-22, NIKALAC MS-21, NIKALAC MS-11, NIKALAC MW-24X, NIKALAC MS-001, NIKALAC MX-002, NIKALAC MX-730, NIKALAC MX-750, NIKALAC MX-708, NIKALAC MX-706, NIKALAC MX-042, NIKALAC MX-45, NIKALAC MX-500, NIKALAC MX-520, NIKALAC MX-43, NIKALAC MX-417, NIKALAC MX-410 (manufactured by Sanwa Chemical Co., Ltd.), CYMEL 232, CYMEL 235, CYMEL 236, CYMEL 238, CYMEL 285, CYMEL 300, CYMEL 301, CYMEL 303, CYMEL 350, CYMEL 370 (manufactured by Japan Cytec Industries Co., Ltd.), etc.

[0260] Among these, NIKALAC MW-30HM, NIKALAC MW-390, NIKALAC MW-100LM, NIKALAC MX-750LM, NIKALAC MW-30M, NIKALAC MW-30, NIKALAC MW-22, NIKALAC MS-21, NIKALAC MS-11, NIKALAC MW-24X, NIKALAC MW-45 (manufactured by Sanwa Chemical Co., Ltd.), CYMEL 232, CYMEL 235, CYMEL 236, CYMEL 238, CYMEL 300, CYMEL 301, CYMEL 303, CYMEL 350 (manufactured by Japan Cytec Industries Co., Ltd.), etc., in which the average number of hydroxymethyl and / or ether groups in each melamine ring is 5.0 or more, are preferred in terms of increasing the crosslinking density.

[0261] The thermosetting compound (G) can be used alone or in combination of two or more.

[0262] [Hardener]

[0263] In order to assist the curing of the thermosetting compound, a hardener (curing accelerator) can be used in combination in the photosensitive coloring composition as needed. Examples of the hardener include amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds, etc. Examples of the curing accelerator include amine compounds (such as dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N,N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (such as triethylbenzylammonium chloride, etc.), block isocyanate compounds (such as dimethylamine, etc.), imidazole derivatives, bicyclic amidine compounds and their salts (such as imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, etc.), phosphorus compounds (such as triphenylphosphine, etc.), S-triazine derivatives (such as 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine / isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine / isocyanuric acid adduct, etc.).

[0264] One type of hardener may be used alone, or two or more types may be used in combination.

[0265] With respect to 100 parts by mass of the thermosetting compound (G), the content of the hardener is preferably from 0.01 part by mass to 15 parts by mass.

[0266] [Antioxidant (H)]

[0267] The photosensitive coloring composition may contain an antioxidant (H). The antioxidant (H) can prevent the film formed from the photosensitive coloring composition from yellowing due to oxidation caused by heat curing or the heat process during annealing of indium tin oxide (ITO), and inhibit the decrease in the transmittance of the film. In particular, when the concentration of the colorant in the photosensitive coloring composition is high, the content of the polymerizable compound relatively decreases. Therefore, when adjusted by increasing the amount of the photoinitiator or formulating a thermosetting compound, the film is liable to yellow. Accordingly, by including the antioxidant (H), yellowing due to oxidation during the heating process can be prevented, and the decrease in the transmittance of the film can be inhibited.

[0268] The antioxidant (H) is a compound having a free radical scavenging function or a peroxide decomposing function. Examples of the antioxidant (H) include hindered phenol compounds, hindered amine compounds, phosphorus compounds, sulfur compounds, and hydroxylamine compounds. In addition, the antioxidant (H) is preferably a compound not containing a halogen atom. Among these, from the viewpoint of achieving both the transmittance and sensitivity of the film, hindered phenol compounds, hindered amine compounds, phosphorus compounds, and sulfur compounds are preferred.

[0269] Examples of hindered phenol antioxidants include: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,3-tris(2'-methyl-4'-hydroxy-5'-tert-butylphenyl)butane, 4,4'-butylidene-bis(2-tert-butyl-5-methylphenol), stearyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 3,9-bis[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-thiodiethyl bis(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, N,N-hexamethylenebis(3,5-di-tert-butyl-4-hydroxyhydroxycinnamamide), isooctyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 4,6-bis(dodecylthiomethyl)-o-cresol, calcium salt of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid monoethyl ester, 4,6-bis(octylthiomethyl)-o-cresol, bis[3-(3-(methyl-4-hydroxy-5-tert-butylphenyl)propionic]ethylenedioxydiethylene ester, 1,6-hexanediol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,4-bis(n-octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine, 2,2'-thio-bis(6-tert-butyl-4-methylphenol), 2,5-di-tertamylhydroquinone, 2,6-di-tert-butyl-4-nonylphenol, 2,2'-isobutylidene-bis(4,6-dimethylphenol), 2,2'-methylenebis(6-(1-methylcyclohexyl)-p-cresol), 2,4-dimethyl-6-(1-methylcyclohexyl)phenol, etc.

[0270] Examples of commercially available products include: Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-60, Adekastab AO-80, Adekastab AO-330 manufactured by ADEKA Corporation; KEMINOX 101, KEMINOX 179, KEMINOX 76, KEMINOX 9425 manufactured by Chemipro Corporation; IRGANOX 1010, IRGANOX 1035, IRGANOX 1076, IRGANOX 1098, IRGANOX 1135, IRGANOX 1330, IRGANOX 1726, IRGANOX 1425WL, IRGANOX 1520L, IRGANOX 245, IRGANOX 259, IRGANOX 3114, IRGANOX 5057, IRGANOX 565 manufactured by BASF Japan Ltd.; CYANOX CY-1790, CYANOX CY-2777, etc. manufactured by Sun Chemical Corporation.

[0271] Examples of hindered amine antioxidants include: tetra(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, tetra(2,2,6,6-tetramethyl-4-piperidyl)1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(1-undecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) carbonate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, the condensate of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], the ester of 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol and 3,5,5-trimethylhexanoic acid, N,N'-4,7-tetra[4,6-bis{N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino}-1,3,5-triazine-2-yl]-4,7-diazadecane-1,10-diamine, the reaction product of bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidyl) sebacate and 1,1-dimethylethyl hydroperoxide with octane, bis(1,2,2,6,6-pentamethyl-4-piperidyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate, methyl 1,2,2,6,6-pentamethyl-4-piperidyl sebacate, poly[[6-morpholino-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], 2,2,6,6-tetramethyl-4-piperidyl-C12-21 and C18 unsaturated fatty acid esters, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propanamide, etc.

[0272] Examples of commercially available products include: Adekastab LA-52, Adekastab LA-57, Adekastab LA-63P, Adekastab LA-68, Adekastab LA-72, Adekastab LA-77Y, Adekastab LA-77G, Adekastab LA-81, Adekastab LA-82, Adekastab LA-87, Adekastab LA-402F, Adekastab LA-502XP, manufactured by ADEKA Corporation; KAMISTAB 29, KAMISTAB 62, KAMISTAB 77, KAMISTAB 94, manufactured by Chemipro Kasei Co., Ltd.; Tinuvin 249, Tinuvin 111FDL, Tinuvin 123, Tinuvin 144, Tinuvin 292, Tinuvin 5100, manufactured by BASF Japan Ltd.; CYASORB UV-3346, CYASORB UV-3529, CYASORB UV-3853, manufactured by Sun Chemical Corporation, etc.

[0273] Phosphorus-based antioxidants include, for example: bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, 2,2'-methylenebis(4,6-di-tert-butylphenyl) 2-ethylhexyl phosphite, tris(2,4-di-tert-butylphenyl) phosphite, tris(nonylphenyl) phosphite, tetra(C12-C15 alkyl)-4,4'-isopropylidenediphenyl diphosphite, diphenyl mono(2-ethylhexyl) phosphite, diphenyl isodecyl phosphite, tris(isodecyl) phosphite, triphenyl phosphite, tetra(2,4-di-tert-butylphenyl)-4,4-biphenyldiphosphonate, tris(tridecyl) phosphite, phenyl isooctyl phosphite, phenyl isodecyl phosphite, phenyl bis(tridecyl) phosphite, diphenyl isooctyl phosphite, diphenyl tridecyl phosphite, 4,4'-isopropylidenediphenol alkylene phosphite, trisnonylphenyl phosphite, tris-dinonylphenyl phosphite, tris(biphenyl) phosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite, phenyl bisphenol A pentaerythritol diphosphite, tetra-tridecyl 4,4'-butylidenebis(3-methyl-6-tert-butylphenol) diphosphite, hexa-tridecyl 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane triphosphite, 3,5-di-tert-butyl-4-hydroxybenzyl phosphite diethyl ester, sodium bis(4-tert-butylphenyl) phosphite, 2,2-methylenebis(4,6-di-tert-butylphenyl)-sodium phosphite, 1,3-bis(diphenoxyphosphoryloxy)-benzene, ethyl bis(2,4-di-tert-butyl-6-methylphenyl) phosphite, etc.

[0274] Commercially available products include: Adekastab PEP-36, Adekastab PEP-8, Adekastab HP-10, Adekastab 2112, Adekastab 1178, Adekastab 1500, Adekastab C, Adekastab 135A, Adekastab 3010, Adekastab TPP, manufactured by ADEKA Corporation; IRGAFOS 168, manufactured by BASF Japan Ltd.; Hostanox P-EPQ, manufactured by Clariant chemicals, etc.

[0275] Examples of the sulfur-based antioxidant include: 2,2-bis{[3-(dodecylthio)-1-oxopropoxy]methyl}propane-1,3-diyl bis[3-(dodecylthio)propionate], di-tridecyl 3,3'-thiodipropionate, 2,2'-thio-diethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]o-cresol, 2,4-bis[(laurylthio)methyl]o-cresol, etc.

[0276] Examples of the commercially available products include Adekastab AO-412S and Adekastab AO-503 manufactured by ADEKA Corporation, and KEMINOX PLS manufactured by Chemipro Kasei Co., Ltd.

[0277] The antioxidant (H) can be used alone or in combination of two or more.

[0278] With respect to 100% by mass of the non-volatile components of the photosensitive coloring composition, the content of the antioxidant (H) is preferably 0.5% by mass to 5.0% by mass. When contained in an appropriate amount, the transmittance, spectral characteristics, and sensitivity are improved.

[0279] [Ultraviolet absorber (I), polymerization inhibitor (J)]

[0280] The photosensitive coloring composition may contain an ultraviolet absorber (I) and a polymerization inhibitor (J). By containing the ultraviolet absorber (I) and the polymerization inhibitor (J), the shape and resolution of the pattern are improved. As the benzotriazole compound that can be used as the ultraviolet absorber (I), for example, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, a mixture of 5 parts of 2-methoxy-1-methylethyl acetate and 95 parts of phenylpropionic acid and 3-(2H-benzotriazol-2-yl)-(1,1-dimethylethyl)-4-hydroxy and C7-9 side chain and straight-chain alkyl ester, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol, the reaction product of methyl 3-(3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl)propionate / polyethylene glycol 300, 2-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-tert-butyl-4-methylphenol, 2-(3,5-ditert-amyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, octyl 3[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, 2-ethylhexyl 3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate can be cited.

[0281] Examples of commercially available products include: TINUVIN P, TINUVIN PS, TINUVIN 234, TINUVIN 326, TINUVIN 329, TINUVIN 384-2, TINUVIN 900, TINUVIN 928, TINUVIN 99-2, TINUVIN 1130, manufactured by BASF Japan Ltd.; Adekastab LA-29, Adekastab LA-31RG, Adekastab LA-32, Adekastab LA-36, manufactured by ADEKA Corporation; KEMISORB 71, KEMISORB 73, KEMISORB 74, KEMISORB 79, KEMISORB 279, manufactured by Chemipro Kasei Co., Ltd.; RUNA-93, manufactured by Otsuka Chemical Co., Ltd., etc.

[0282] Examples of triazine compounds that can be used as the ultraviolet absorber (I) include: 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; the reaction product of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl)-glycidate; 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-triazin-2-yl)-5-[2-(2-ethylhexanoyloxy)ethoxy]phenol; 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-1,3,5-triazine, etc.

[0283] Examples of commercially available products include: KEMISORB 102 manufactured by Chemipro Kasei Co., Ltd.; TINUVIN 400, TINUVIN 405, TINUVIN 460, TINUVIN 477, TINUVIN 479, TINUVIN 1577ED manufactured by BASF Japan Ltd.; Adekastab LA-46, Adekastab LA-F70 manufactured by ADEKA Corporation; CYASORB UV-1164 manufactured by Sun Chemical Corporation, etc.

[0284] Examples of benzophenone compounds that can be used as the ultraviolet absorber (I) include: 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2-hydroxy-4-n-octyloxybenzophenone, 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, etc.

[0285] Examples of commercially available products include: KEMISORB 10, KEMISORB 11, KEMISORB 11S, KEMISORB 12, KEMISORB 111 manufactured by Chemipro Kasei Co., Ltd.; SEESORB 101, SEESORB 107 manufactured by Shipro Kasei Co., Ltd.; Adekastab 1413 manufactured by ADEKA Corporation; UV-12 manufactured by Sun Chemical Corporation, etc.

[0286] Examples of salicylate compounds that can be used as the ultraviolet absorber (I) include: phenyl salicylate, p-octylphenyl salicylate, p-tert-butylphenyl salicylate, etc.

[0287] In addition, examples of the polymerization inhibitor (J) include: catechol, resorcinol, 1,4-hydroquinone, 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol, 3-ethylcatechol, 4-ethylcatechol, 2-propylcatechol, 3-propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol, 4-n-butylcatechol, 2-t-butylcatechol, 3-t-butylcatechol, 4-t-butylcatechol, 3,5-di-t-butylcatechol and other alkylcatechol compounds; 2-methylresorcinol, 4-methylresorcinol, 2-ethylresorcinol, 4-ethylresorcinol, 2-propylresorcinol, 4-propylresorcinol, 2-n-butylresorcinol, 4-n-butylresorcinol, 2-t-butylresorcinol, 4-t-butylresorcinol and other alkylresorcinol compounds; methylhydroquinone, ethylhydroquinone, propylhydroquinone, tert-butylhydroquinone, 2,5-di-t-butylhydroquinone and other alkylhydroquinone compounds; phosphine compounds such as tributylphosphine, trioctylphosphine, tricyclohexylphosphine, triphenylphosphine, tribenzylphosphine; phosphine oxide compounds such as trioctylphosphine oxide, triphenylphosphine oxide; phosphite compounds such as triphenyl phosphite, tris(nonylphenyl) phosphite; pyrogallol, phloroglucin, etc.

[0288] The ultraviolet absorber (I) and the polymerization inhibitor (J) can be used alone or in combination of two or more.

[0289] With respect to 100 parts by mass of the colorant (D), the contents of the ultraviolet absorber (I) and the polymerization inhibitor (J) are each preferably 0.01 part by mass to 20 parts by mass, more preferably 0.05 part by mass to 10 parts by mass. The resolution is improved by using an appropriate amount.

[0290] With respect to 100% by mass of the total of the photoinitiator and the ultraviolet absorber, the content of the ultraviolet absorber (I) is preferably 5% by mass to 70% by mass. When contained in an appropriate amount, a good pattern shape is easily obtained.

[0291] With respect to 100% by mass of the non-volatile components of the photosensitive color composition, the content of the polymerization inhibitor (J) is preferably 0.01% by mass to 0.4% by mass. When contained in an appropriate amount, a good pattern shape is easily obtained.

[0292] [Solvent]

[0293] The photosensitive coloring composition may contain a solvent. Examples of the solvent include: 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanediol, 1,3-butylene glycol, 1,3-butanediol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 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-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monoter t-butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene 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, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, diesters of dibasic acids, etc. Among these, from the viewpoints of the dispersibility of the colorant and the solubility of the binder resin, glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether acetate; alcohols such as benzyl alcohol and diacetone alcohol; or ketones such as cyclohexanone are preferred.

[0294] The solvent may be used alone or in combination of two or more.

[0295] With respect to 100 parts by mass of the colorant (D), the content of the solvent is preferably 100 parts by mass to 10,000 parts by mass, more preferably 500 parts by mass to 5,000 parts by mass.

[0296] [Silane Coupling Agent (K)]

[0297] The photosensitive coloring composition may contain a silane coupling agent (K). Thereby, the adhesion to the substrate is improved.

[0298] Examples of the silane coupling agent (K) include: vinyl silanes such as vinyltris(β-methoxyethoxy)silane, vinyl ethoxysilane, and vinyltrimethoxysilane; (meth)acrylic group silanes such as γ-methacryloxypropyltrimethoxysilane; epoxy silanes such as β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)methyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and γ-glycidoxypropyltriethoxysilane; amino silanes such as N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, and N-phenyl-γ-aminopropyltriethoxysilane; thiosilane such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane, etc.

[0299] With respect to 100 parts by mass of the colorant (D), the content of the silane coupling agent (K) is preferably 0.01 part by mass to 10 parts by mass, more preferably 0.05 part by mass to 5 parts by mass.

[0300] In addition, the photosensitive coloring composition may contain an amine compound having a function of reducing the dissolved oxygen. Examples of the amine compound include: triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-(dimethylamino)ethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, etc.

[0301] [Leveling Agent (L)]

[0302] The photosensitive coloring composition may contain a leveling agent (L). Thereby, the wettability to the transparent substrate and the drying property of the film during film formation are further improved. Examples of the leveling agent (L) include: silicone surfactants, fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, etc.

[0303] Examples of silicone surfactants include linear polymers containing siloxane bonds and modified silicone polymers with organic groups introduced into the side chains or terminals.

[0304] Examples of commercially available products include BYK-300, BYK-306, BYK-310, BYK-313, BYK-315N, BYK-320, BYK-322, BYK-323, BYK-330, BYK-331, BYK-333, BYK-342, BYK-345, BYK-346, BYK-347, BYK-348, BYK-349, BYK-370, BYK-377, BYK-378, BYK-3455, BYK-UV3510, BYK-UV3570 manufactured by BYK-Chemie; FZ-7002, FZ-2110, FZ-2122, FZ-2123, FZ-2191, FZ-5609 manufactured by Toray Dow Corning; X-22-4952, X-22-4272, X-22-6266, KF-351A, KF-354L, KF-355A, KF-945, KF-640, KF-642, KF-643, X-22-4515, KF-6004, KP-341 manufactured by Shin-Etsu Chemical Co., Ltd.

[0305] Examples of fluorine-based surfactants include surfactants or leveling agents having fluorocarbon chains.

[0306] Examples of commercially available products include: Surflon S-242, Surflon S-243, Surflon S-420, Surflon S-611, Surflon S-651, Surflon S-386 manufactured by AGC Seimi Chemical Co., Ltd.; Megafac F-253, Megafac F-477, Megafac F-551, Megafac F-552, Megafac F-555, Megafac F-558, Megafac F-560, Megafac F-570, Megafac F-575, Megafac F-576, Megafac R-40-LM, Megafac R-41, Megafac RS-72-K, Megafac DS-21 manufactured by DIC Corporation; FC-4430, FC-4432 manufactured by Sumitomo 3M Limited; EF-PP31N09, EF-PP33G1, EF-PP32C1 manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.; Ftergent 602A manufactured by NEOS Corporation, etc.

[0307] Examples of nonionic surfactants include: polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene alkyl ether, polyoxyethylene myristyl ether, polyoxyethylene octyldodecyl ether, polyoxyalkylene alkyl ether, polyoxyphenylene stilbenized phenyl ether, polyoxyethylene tribenzylphenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyalkylene alkenyl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan distearate, sorbitan tristearate, sorbitan monooleate, sorbitan trioleate, sorbitan sesquioleate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan anhydride monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan triisostearate, polyoxyethylene sorbitol tetraoleate, glyceryl monostearate, glyceryl monooleate, polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene glycol monooleate, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, alkyl alkanolamide, alkyl imidazoline, etc.

[0308] Examples of commercially available products include: Emulgen 103, Emulgen 104P, Emulgen 106, Emulgen 108, Emulgen 109P, Emulgen 120, Emulgen 123P, Emulgen 130K, Emulgen 147, Emulgen 150, Emulgen 210P, Emulgen 220, Emulgen 306P, Emulgen 320P, Emulgen 350, Emulgen 404, Emulgen 408, Emulgen 409PV, Emulgen 420, Emulgen 430, Emulgen 705, Emulgen 707, Emulgen 709, Emulgen 1108, Emulgen 1118S-70, Emulgen 1135S-70, Emulgen 1150S-60, Emulgen 2020G-HA, Emulgen 2025G, Emulgen LS-106, Emulgen LS-110, Emulgen LS-114, Emulgen MS-110, Emulgen A-60, Emulgen A-90, Emulgen B-66, Emulgen PP-290, Latemul PD-420, Latemul PD-430, Latemul PD-430S, Latemul PD-450, Rheodol SP-L10, Rheodol SP-P10, Rheodol SP-S10V, Rheodol SP-S20, Rheodol SP-S30V, Rheodol SP-O10V, Rheodol SP-O30V, Rheodol SuperSuper) SP-L10, Rheodol AS-10V, Rheodol AO-10V, Rheodol AO-15V, Rheodol TW-L120, Rheodol TW-L106, Rheodol TW-P120, Rheodol TW-S120V, Rheodol TW-S320V, Rheodol TW-O120V, Rheodol TW-O106V, Rheodol TW-IS399C, Rheodol Super TW-L120, Rheodol 430V, Rheodol 440V, Rheodol 460V, Rheodol MS-50, Rheodol MS-60, Rheodol MO-60, Rheodol MS-165V, Emanon 1112, Emanon 3199V, Emanon 3299V, Emanon 3299RV, Emanon 4110, Emanon CH-25, Emanon CH-40, Emanon CH-60(K), Amiet 102, Amiet 105, Amiet 105A, Amiet 302, Amiet 320, Aminon PK-02S, Aminon L-02, Homogenol L-95, Adeka Pluronic L-23, Adeka Pluronic L-31, Adeka Pluronic L-44, Adeka Pluronic L-61, Adeka Pluronic L-62, Adeka Pluronic L-64, Adeka Pluronic L-71, Adeka Pluronic L-72, Adeka Pluronic L-101, Adeka Pluronic L-121, Adeka Pluronic (AdekaPluronic) TR-701, Adeka Pluronic) TR-702, Adeka Pluronic) TR-704, Adeka Pluronic) TR-913R, (meth)acrylic (co)polymers Polyflow No. 75, Polyflow No. 90, Polyflow No. 95, etc. manufactured by Kyoeisha Chemical Co., Ltd.

[0309] Examples of cationic surfactants include: alkylamine salts or alkyl quaternary ammonium salts such as lauryl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, or ethylene oxide adducts thereof.

[0310] Examples of commercially available products include Acetamin 24, Quartamin 24P, Quartamin 60W, Quartamin 86P CONC, etc. manufactured by Kao Corporation.

[0311] Examples of anionic surfactants include: polyoxyethylene alkyl ether sulfates, sodium dodecylbenzenesulfonate, alkali salts of styrene - acrylic acid copolymers, sodium alkylnaphthalenesulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine styrene - acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, etc.

[0312] Examples of commercially available products include Ftergent 100, Ftergent 150 manufactured by NEOS Corporation, ADEKA HOPE YES - 25, ADEKA COL TS - 230E, ADEKA COL PS - 440E, ADEKA COL EC - 8600, etc. manufactured by ADEKA Corporation.

[0313] Examples of amphoteric surfactants include: alkyl betaines such as lauric acid amide propyl betaine, lauryl betaine, coconut oil amide propyl betaine, stearyl betaine, alkyl dimethyl aminoacetic acid betaine; alkyl amine oxides such as lauryl dimethyl amine oxide, etc.

[0314] Examples of commercially available products include Amphitol 20AB, Amphitol 20BS, Amphitol 24B, Amphitol 55AB, Amphitol 86B, Amphitol 20Y - B, Amphitol 20N, etc., manufactured by Kao Corporation.

[0315] The leveling agent (L) can be used alone or in combination of two or more.

[0316] With respect to 100% by mass of the non - volatile components of the photosensitive coloring composition, the content of the leveling agent (L) is preferably 0.001% by mass to 2.0% by mass, more preferably 0.005% by mass to 1.0% by mass. Thus, the coatability, pattern adhesion, and transmittance of the photosensitive coloring composition can be improved in a balanced manner.

[0317] [Other components]

[0318] (Storage stabilizer)

[0319] The photosensitive coloring composition may contain a storage stabilizer. By containing a storage stabilizer, the viscosity of the composition over time can be stabilized. Examples of storage stabilizers include hindered phenols such as 2,6 - bis(1,1 - dimethylethyl) - 4 - methylphenol, pentaerythritol tetra[3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate], 2,4 - bis(n - octylthio) - 6 - (4 - hydroxy - 3,5 - di - tert - butylaniline) - 1,3,5 - triazine; organic phosphines such as tert - butylcatechol, tetraethylphosphine, triphenylphosphine, tetraphenylphosphine; phosphites such as zinc dimethyldithiophosphate, zinc dipropyldithiophosphate, molybdenum dibutyldithiophosphate; sulfur - based compounds such as dodecyl sulfide, benzothiophene; quaternary ammonium chlorides such as benzyltrimethyl chloride, diethylhydroxylamine; organic acids such as lactic acid, oxalic acid and their methyl ethers.

[0320] The storage stabilizer can be used alone or in combination of two or more.

[0321] With respect to 100 parts by mass of the colorant (D), the content of the storage stabilizer is preferably 0.01 part by mass to 20 parts by mass, more preferably 0.05 part by mass to 10 parts by mass, and still more preferably 0.1 part by mass to 10 parts by mass. When contained in an appropriate amount, the stability over time is improved.

[0322] (Adhesion improver)

[0323] The photosensitive coloring composition may contain an adhesion improver. Thereby, the adhesion between the film and the substrate is further improved. In addition, it is easy to form a narrow - width pattern by photolithography.

[0324] Examples of the adhesion improver include silane coupling agents. Specific examples include vinyl silanes such as vinyltrimethoxysilane and vinyltriethoxysilane; (meth)acrylic group silanes such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane; epoxy silanes such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; amino silanes such as N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and hydrochloride of N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; mercapto group silanes such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; styryl group silanes such as p-styryltrimethoxysilane; ureido group silanes such as 3-ureidopropyltriethoxysilane; thioether group silanes such as bis(triethoxysilylpropyl)tetrasulfide; and isocyanate group silanes such as 3-isocyanatopropyltriethoxysilane, etc.

[0325] The adhesion improver may be used alone or in combination of two or more.

[0326] With respect to 100 parts by mass of the colorant (D), the content of the adhesion improver is preferably from 0.01 part by mass to 10 parts by mass, more preferably from 0.05 part by mass to 5 parts by mass. When contained in an appropriate amount, the photosensitivity of the photosensitive coloring composition is improved, and the adhesion of the film is further improved, thereby obtaining a good pattern shape.

[0327] <Manufacturing method of the photosensitive coloring composition>

[0328] The method for producing the photosensitive coloring composition is not particularly limited, and existing methods can be used. As an example of the method for producing the photosensitive coloring composition, for example, first, a dispersion treatment is performed using a colorant (D), a dispersant, a solvent, etc. to produce a colorant dispersion. In addition, when the solubility of the colorant (D) in the solvent is high, the dispersion treatment may not be required. When two or more colorants (D) are used in combination, colorant dispersions can be produced for each colorant (D) and then mixed. Alternatively, a colorant dispersion can also be produced using multiple colorants (D) together. Next, a photoinitiator (A), a binder resin (B), and a photopolymerizable compound (C) are formulated in the colorant dispersion and mixed to obtain a photosensitive coloring composition. In addition, the timing of formulating each material is of course arbitrary.

[0329] For the dispersion treatment, dispersion devices such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular type bead mill, or a grinder can be used.

[0330] The average dispersed particle diameter (secondary particle diameter) of the colorant (D) in the dispersion is preferably 30 nm to 200 nm, more preferably 40 nm to 200 nm. If it is within this range, a photosensitive coloring composition with high dispersion stability can be obtained, and when a color filter is produced using it, a high-quality color filter is obtained.

[0331] Examples of the method for measuring the average dispersed particle diameter (secondary particle diameter) include the following method: Using the Microtrack UPA-EX150 of Nikkiso Co., Ltd. that adopts the dynamic light scattering method (fast Fourier transform (FFT) power spectrum method), setting the particle transmittance to the absorption mode, setting the particle shape to non-spherical, and setting D50 to the average diameter. The dilution solvent for measurement uses the organic solvent used in the dispersion respectively. When measuring the sample that has been treated with ultrasonic waves immediately after sample adjustment, it is easy to obtain results with small deviations and is preferred.

[0332] [Removal of Coarse Particles]

[0333] Regarding the photosensitive coloring composition, it is preferably to remove coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more, and mixed dust by means such as centrifugal separation with a gravitational acceleration of 3000G to 25000G, filtration using a sintered filter or a membrane filter. Thus, the photosensitive coloring composition preferably substantially does not contain particles of 0.5 μm or more. More preferably, it is 0.3 μm or less.

[0334] <Color Filter>

[0335] The color filter includes a substrate and filter segments formed from the photosensitive coloring composition. The color filter segments (hereinafter also referred to as filter segments) can have red filter segments, green filter segments, and blue filter segments by appropriately selecting the type of coloring agent (D) used. In addition, the color filter may also have magenta filter segments, cyan filter segments, and yellow filter segments as color filter segments. Furthermore, the substrate is preferably a transparent substrate and a reflective substrate. Examples of the transparent substrate include a glass substrate. Examples of the reflective substrate include a substrate using an aluminum electrode or a metal thin film as a reflective surface.

[0336] <Method for manufacturing a color filter>

[0337] As an example of the method for manufacturing a color filter, for example, it can be obtained through the following steps: a step of coating a photosensitive coloring composition on a substrate to form a coloring layer, a step of exposing the coloring layer through a mask to form a pattern, and a step of developing and removing the unexposed portion to form a coloring pattern.

[0338] Furthermore, a step of drying the coloring layer (pre-baking step) and a step of thermally hardening the coloring pattern (post-baking) can also be provided as needed.

[0339] Hereinafter, the method for manufacturing the color filter of the present invention will be described in detail.

[0340] (Step of forming a coloring layer)

[0341] Regarding the step of forming a coloring layer, first, a black matrix is formed on the substrate, and then filter segments are formed. In addition, a thin film transistor (TFT) can be formed on the substrate in advance and then a black matrix can be formed. Examples of the black matrix include inorganic films such as chromium, a multilayer film of chromium / chromium oxide, titanium nitride, or a resin film in which a light-shielding agent is dispersed.

[0342] Next, for example, by using photolithography, a photosensitive coloring composition containing a coloring agent of a certain hue is coated on the substrate by a coating method such as spin coating, roll coating, slit coating, casting coating, or inkjet coating so that the dry film thickness becomes about 0.2 μm to 5 μm, thereby forming a film. As needed, an oven, a hot plate, etc. are used to dry (pre-bake) at a temperature of 50°C to 120°C for 10 seconds to 120 seconds.

[0343] (Step of exposing to form a pattern)

[0344] In the exposure step, for example, an exposure device such as a stepper is used to expose a specific pattern to the first film formed in the step of forming a coloring layer through a mask. Thereby, a hardened film is obtained.

[0345] The radiation that can be used for exposure is preferably ultraviolet rays such as g-rays, h-rays, and i-rays.

[0346] The film thickness of the hardened film is preferably 1.0 μm or less, more preferably 0.2 μm to 0.8 μm, and particularly preferably 0.2 μm to 0.6 μm.

[0347] (Development process)

[0348] By performing alkali development treatment, the colored layer in the unexposed part in the exposure process is eluted into the alkaline aqueous solution, and only the hardened part remains.

[0349] As the developer, an existing developer can be used without particular limitation. Specifically, examples include alkaline aqueous solutions in which alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, and 1,8-diazabicyclo-[5.4.0]-7-undecene are dissolved at a concentration of 0.001% by mass to 10% by mass, preferably 0.01% by mass to 1% by mass. In addition, an antifoaming agent or a surfactant can be added to the developer.

[0350] The alkali developer is preferably an alkaline aqueous solution in which the alkali concentration is adjusted to preferably pH 11 to pH 13, and more preferably pH 11.5 to pH 12.5. When the alkali concentration is within the above range, the roughness or peeling of the pattern can be more effectively suppressed, the residual film rate can be further increased, and the decrease in the development rate or the generation of development residues can be more effectively suppressed.

[0351] Existing methods can be used for the development method. For example, there are dipping methods, spraying methods, liquid covering methods, etc., and the temperature is preferably 15°C to 40°C. After alkali development, it is preferably washed with pure water.

[0352] Next, after drying is carried out, in order to fully harden the hardened film, a heat treatment (post-baking) is preferably performed. The heating temperature for post-baking is preferably 100°C to 300°C, and more preferably 150°C to 250°C. In addition, the heating time is preferably about 2 minutes to 1 hour, and more preferably about 3 minutes to 30 minutes.

[0353] In addition, polyvinyl alcohol or a water-soluble acrylic resin can be further used on the film before exposure to form a second film (oxygen barrier film). As a result, the first film does not come into contact with oxygen, so the exposure sensitivity is further improved. In addition, the color filter can be heated to harden the unhardened photopolymerizable compound in the filter section.

[0354] <Image display device>

[0355] The image display device includes a color filter. The image display device preferably further includes a light source. A liquid crystal display device will be described as an example of the image display device. The liquid crystal display device includes a color filter and a light source. As the light source, for example, a cold cathode tube (Cold Cathode Fluorescent Lamp, CCFL), a white Light-Emitting Diode (LED) can be cited. In the present embodiment, in terms of a wide reproduction area of red, it is preferable to use a white LED. Figure 1 FIG. is a schematic cross-sectional view of a liquid crystal display device 10 including a color filter. Figure 1 The device 10 shown in FIG. includes a pair of transparent substrates 11 and 21 that are spaced apart and arranged facing each other, and a liquid crystal LC is sealed between them.

[0356] The liquid crystal LC is oriented according to driving modes such as the Twisted Nematic (TN) mode, the Super Twisted Nematic (STN) mode, the In-Plane Switching (IPS) mode, the Vertical Alignment (VA) mode, the Optically Compensated Birefringence (OCB) mode, etc.

[0357] On the inner surface of the first transparent substrate 11, a TFT (Thin Film Transistor) array 12 is formed, and a transparent electrode layer 13 including, for example, ITO is formed thereon. An alignment layer 14 is provided on the transparent electrode layer 13. In addition, a polarizing plate 15 is formed on the outer surface of the transparent substrate 11.

[0358] On the other hand, a color filter 22 is formed on the inner surface of the second transparent substrate 21. The red, green, and blue filter segments constituting the color filter 22 are separated by a black matrix (not shown).

[0359] A transparent protective film (not shown) is formed to cover the color filter 22 as needed, and then a transparent electrode layer 23 including, for example, ITO is formed thereon, and an alignment layer 24 is provided to cover the transparent electrode layer 23.

[0360] In addition, a polarizing plate 25 is formed on the outer surface of the transparent substrate 21. Further, a backlight unit 30 is provided below the polarizing plate 15.

[0361] As the white LED light source 31, there are those in which a fluorescent filter is formed on the surface of a blue LED, or those in which a phosphor is contained in the resin encapsulation of a blue LED, and preferably the following white LED light sources (LED 1) and white LED light sources (LED 2). The white LED light source (LED 1) has the following spectral characteristics: it has a wavelength (λ3) at which the luminous intensity becomes maximum in the range of 430 nm to 485 nm, a wavelength (λ4) at which the luminous intensity becomes maximum in the range of 530 nm to 580 nm, and a wavelength (λ5) at which the luminous intensity becomes maximum in the range of 600 nm to 650 nm, and the ratio (I4 / I3) of the luminous intensity I3 at wavelength λ3 to the luminous intensity I4 at wavelength λ4 is 0.2 or more and 0.4 or less, and the ratio (I5 / I3) of the luminous intensity I3 at wavelength λ3 to the luminous intensity I5 at wavelength λ5 is 0.1 or more and 1.3 or less; the white LED light source (LED 2) has the following spectral characteristics: it has a wavelength (λ1) at which the luminous intensity becomes maximum in the range of 430 nm to 485 nm, and a peak wavelength (λ2) of the second luminous intensity in the range of 530 nm to 580 nm, and the ratio (I2 / I1) of the luminous intensity I1 at wavelength λ1 to the luminous intensity I2 at wavelength λ2 is 0.2 or more and 0.7 or less.

[0362] As LED 1, specifically, NSSW306D-HG-V1 (manufactured by Nichia Chemical Industries, Ltd.), NSSW304D-HG-V1 (manufactured by Nichia Chemical Industries, Ltd.), etc. can be cited.

[0363] As LED 2, specifically, NSSW440 (manufactured by Nichia Chemical Industries, Ltd.), NSSW304D (manufactured by Nichia Chemical Industries, Ltd.), etc. can be cited.

[0364] As an example of a method for manufacturing a liquid crystal display device, for example, first after forming the filter section, the color filter is bonded to the opposing substrate using a sealant, after injecting liquid crystal from the injection port provided in the sealing portion, the injection port is sealed, and if necessary, a polarizing film and a retardation film are bonded to the outside of the substrate. Thus, a liquid crystal display device can be manufactured.

[0365] The image display device can be used not only for liquid crystal display devices but also for applications such as solid-state imaging elements, organic EL display devices, quantum dot display devices, electronic paper, head-mounted displays, etc.

[0366] <Examples of Embodiments>

[0367] Examples of embodiments of the present invention are listed below. The embodiments of the present invention are not limited to the following examples.

[0368] [1]A photosensitive coloring composition contains a first photoinitiator represented by the following general formula (1), a binder resin, a photopolymerizable compound, and a colorant.

[0369] General formula (1)

[0370]

[0371] (In the formula, R1 and R2 each independently represent R 11 or COR 11 , 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. The alkyl part of the alkyl group, aryl group, arylalkyl group, or heterocyclic group represented by R 11 can be a branched side chain or a cyclic alkyl group. 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. The alkyl part of the alkyl group, aryl group, arylalkyl group, or heterocyclic group represented by R3 can be a branched side chain or a cyclic alkyl group. The hydrogen atom of the aryl group, arylalkyl group, or heterocyclic group represented by R3 can be further substituted by R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , NR 22 COR 21 , OCOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, a cyano group (-CN), a halogen atom, or COOR 21 . R 21 , R 22 and R 23 each independently represent 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 23The hydrogen atom of the represented alkyl, aryl, arylalkyl or heterocyclic group may further be substituted by a hydroxyl group, nitro group, cyano group (-CN), halogen atom, or carboxyl group. In R 21 , R 22 , and R 23 , in the alkylene moiety of the represented alkyl, aryl, arylalkyl or heterocyclic group, -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS-, or -CSO- may contain 1 to 5 under the condition that oxygen atoms are not adjacent to each other.

[0372] 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. The alkyl moiety of the alkyl, aryl, arylalkyl, or heterocyclic group represented by R 24 may be a branched side chain or a cyclic alkyl group. R4 represents a hydrogen atom, a hydroxyl group, a cyano group (-CN), a nitro group, or a halogen atom, and n represents 0 or 1).

[0373] [2] The photosensitive coloring composition as described above, wherein the binder resin (B) comprises an alkali-soluble resin selected from the following (I) and (II) and having a carboxyl group and a polymerizable unsaturated group in the side chain.

[0374] (I) An alkali-soluble resin obtained by reacting a reaction product of an epoxy group in a polyacid or polyacid anhydride and a polymer having an epoxy group with a carboxyl group-containing monomer.

[0375] (II) An alkali-soluble resin which is a reaction product of a carboxyl group in a polymer having a carboxyl group and a monomer containing an epoxy group.

[0376] [3] The photosensitive coloring composition as described above, further comprising a polyfunctional thiol (F).

[0377] [4] The photosensitive coloring composition as described above, further comprising a photopolymerization initiator (Y).

[0378] [5] The photosensitive coloring composition as described above, wherein the photopolymerization initiator (Y) comprises one or more compounds selected from the group consisting of oxime ester compounds, acetophenone compounds, phosphine compounds, and imidazole compounds.

[0379] [6] A color filter, comprising a substrate, and a filter segment or a black matrix formed from the photosensitive coloring composition as described above.

[0380] [7]An image display device includes the color filter as described above.

[0381] [8]A photosensitive coloring composition contains a colorant (D), an alkali-soluble resin, a photopolymerizable compound (C), and a photopolymerization initiator (A), wherein the photopolymerization initiator (A) contains a photopolymerization initiator (Y') represented by the following general formula (2) and a photopolymerization initiator (A') represented by the following general formula (3).

[0382] General formula (2)

[0383]

[0384] (In the formula, R1 represents an alkyl group having an alicyclic hydrocarbon group and having 4 to 20 carbon atoms, R2 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, and R3 represents a hydrogen atom, a nitro group, a group having an ether bond, or an aromatic group)

[0385] General formula (3)

[0386]

[0387] (In the formula, R4 and R5 each independently represent 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)

[0388] [9]The photosensitive coloring composition as described above, wherein, based on 100 parts by mass of the total content of the photopolymerization initiator (A') and the photopolymerization initiator (Y'), the content of the photopolymerization initiator (Y') is 5 to 95 parts by mass.

[0389]

[10] The photosensitive coloring composition as described above, wherein the photopolymerization initiator (A) further contains a photopolymerization initiator (Z) other than the photopolymerization initiator (A') and the photopolymerization initiator (Y').

[0390]

[11] The photosensitive coloring composition as described above, wherein the photopolymerization initiator (Z) is at least one selected from the group consisting of acetophenone-based compounds, acylphosphine oxide-based compounds, and imidazole-based compounds.

[0391]

[12] The photosensitive coloring composition as described above, wherein, based on 100 parts by mass of the content of the photopolymerization initiator (A) contained in the photosensitive coloring composition, the total content of the photopolymerization initiator (A') and the photopolymerization initiator (Y') is 30 parts by mass or more.

[0392]

[13] The photosensitive coloring composition as described above, wherein the photopolymerizable compound (C) includes a polymerizable compound (C-1) having a structure derived from a lactone.

[0393]

[14] The photosensitive coloring composition as described above, wherein the photopolymerizable compound (C) includes a polymerizable compound (C-2) having an acidic group.

[0394]

[15] The photosensitive coloring composition as described above, further comprising a sensitizer (E).

[0395]

[16] A color filter, comprising a substrate and a filter segment formed using the photosensitive coloring composition as described above.

[0396]

[17] An image display device, comprising the color filter as described above.

[0397] The present invention relates to the subject matter of Japanese Patent Application No. 2020-077121 filed on April 24, 2020 and the subject matter of Japanese Patent Application No. 2020-115897 filed on July 3, 2020, and the entire disclosure thereof is incorporated herein by reference.

[0398] [Examples]

[0399] Hereinafter, an embodiment of the present invention will be specifically described by way of examples, but the present invention is not limited to the examples. In addition, hereinafter, "parts" refers to parts by mass, and "%" refers to mass%.

[0400] Hereinafter, PGMAc represents propylene glycol monomethyl ether acetate.

[0401] The calculation methods for the average molecular weight of the resin, and the acid value, amine value, and ammonium salt value of the resin will be described.

[0402] (Average molecular weight of the resin)

[0403] The number average molecular weight (Mn) and weight average molecular weight (Mw) of the resin were measured by gel permeation chromatography (GPC) equipped with a refractive index (RI) detector. As the apparatus, HLC-8220GPC (manufactured by Tosoh Corporation) was used, and two separation columns were connected in series. Two "TSK gel super HZM-N (TSK-GEL SUPER HZM-N)" were connected and used as the packing materials in both columns. The measurement was carried out at an oven temperature of 40 °C, using a THF solution as the eluent, and at a flow rate of 0.35 ml / min. The sample was dissolved in a solvent containing 1 wt% of the eluent, and 20 μl was injected. The molecular weights were all in terms of polystyrene conversion values.

[0404] (Acid value of the resin)

[0405] 80 ml of acetone and 10 ml of water were added to 0.5 g to 1 g of the resin solution and stirred to dissolve it uniformly. A 0.1 mol / L aqueous potassium hydroxide (KOH) solution was used as the titrant, and an automatic titrator ("COM-555" manufactured by Hiranuma Sangyo Co., Ltd.) was used for titration to measure the acid value (mgKOH / g) of the resin solution. Moreover, the acid value per unit non-volatile component of the resin was calculated based on the acid value of the resin solution and the concentration of the non-volatile component in the resin solution.

[0406] (Amine value of the basic resin type dispersant)

[0407] The amine value of the basic resin type dispersant is the value obtained by converting the measured total amine value (mgKOH / g) according to the method of American Society for Testing Material (ASTM) D 2074 into non-volatile component terms.

[0408] (Ammonium salt value of the resin having a cationic group in the side chain)

[0409] The ammonium salt value of the resin having a cationic group in the side chain was obtained by titration with 0.1 N aqueous silver nitrate solution using 5% aqueous potassium chromate solution as an indicator, and then converted into the equivalent of potassium hydroxide, representing the ammonium salt value of the non-volatile component.

[0410] (Experimental Example 1)

[0411] <Method for manufacturing a micronized pigment>

[0412] (Micronized pigment (PB-1))

[0413] 100 parts of copper phthalocyanine-based blue pigment C.I. Pigment Blue 15:6 (“LIONOL BLUE ES” manufactured by Toyocolor Co., Ltd.), 1000 parts of crushed salt, and 100 parts of diethylene glycol were charged into a 1-gallon stainless-steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 50 °C for 12 hours. The mixture was poured into 3000 parts of warm water, stirred with a high-speed mixer for about 1 hour while heating to about 70 °C to make a slurry, and filtered and washed repeatedly to remove salt and solvent. Then, it was dried at 80 °C for 24 hours to obtain a micronized pigment (PB-1).

[0414] (Micronized pigment (PB-2))

[0415] Except that the copper phthalocyanine-based blue pigment C.I. Pigment Blue 15:6 of the micronized pigment (PB-1) was changed to copper phthalocyanine-based blue pigment C.I. Pigment Blue 15 (“COSMOSBLUE ASF” manufactured by Zhuhai Toyo Kemi Co., Ltd.), the micronized pigment (PB-2) was obtained in the same manner as the micronized pigment (PB-1).

[0416] (Micronized pigment (PV-1))

[0417] 200 parts of dioxazine-based purple pigment C.I. Pigment Violet 23 (“LIONOGEN VIOLET RL” manufactured by Toyocolor Co., Ltd.), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1-gallon stainless-steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80 °C for 6 hours. Then, the kneaded product was poured into 8000 parts of warm water, stirred for 2 hours while heating to 80 °C to make a slurry, and filtered and washed repeatedly to remove sodium chloride and diethylene glycol. Then, it was dried at 85 °C for a whole day and night to obtain a micronized pigment (PV-1).

[0418] (Micronized pigment (PG-1))

[0419] In a reaction vessel, 225 parts of phthalodinitrile, 78 parts of aluminum chloride anhydride were added to 1250 parts of n-pentanol, and the mixture was stirred. 266 parts of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) were added thereto, and the temperature was raised, and the mixture was refluxed at 136 °C for 5 hours. While maintaining stirring, the reaction solution cooled to 30 °C was injected into a mixed solvent of 5000 parts of methanol and 10000 parts of water under stirring to obtain a blue slurry. The slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of phthalocyanine aluminum chloride. Further, in a reaction vessel, 100 parts of chloroaluminum phthalocyanine were slowly added to 1200 parts of concentrated sulfuric acid at room temperature. The mixture was stirred at 40 °C for 3 hours, and the sulfuric acid solution was injected into 24000 parts of cold water at 3 °C. The blue precipitate was filtered, washed with water, and dried to obtain 102 parts of the aluminum phthalocyanine pigment represented by the following structural formula (11).

[0420] Structural formula (11)

[0421]

[0422] In a reaction vessel, 100 parts of the aluminum phthalocyanine pigment represented by the structural formula (11) and 49.5 parts of diphenyl phosphate were added to 1000 parts of methanol, heated to 40 °C and reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain 114 parts of the aluminum phthalocyanine pigment represented by the following structural formula (12). 100 parts of the obtained aluminum phthalocyanine pigment represented by the structural formula (12), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 70 °C for 6 hours. The kneaded product was put into 3000 parts of warm water, heated to 70 °C while stirring for 1 hour to form a slurry, and repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 °C for a whole day and night to obtain a micronized pigment (PG-1). The volume average primary particle size was 31.2 nm.

[0423] Structural formula (12)

[0424]

[0425] (Micronized pigment (PG-2))

[0426] In a reaction vessel, 100 parts of an aluminum phthalocyanine pigment represented by the structural formula (11) and 43.2 parts of diphenylphosphinic acid were added to 1000 parts of methanol, and the mixture was heated to 40 °C and reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain 112 parts of an aluminum phthalocyanine pigment represented by the following structural formula (13).

[0427] The obtained aluminum phthalocyanine pigment represented by the structural formula (13) was treated in the same manner as the micronized pigment (PG-1) to obtain a micronized pigment (PG-2). The volume-average primary particle diameter was 29.5 nm.

[0428] Structural formula (13)

[0429]

[0430] (Micronized pigment (PG-3))

[0431] According to the synthesis method described in Japanese Patent Laid-Open No. 2010-79247, an aluminum phthalocyanine pigment represented by the following structural formula (14) was obtained. The obtained aluminum phthalocyanine pigment represented by the structural formula (14) was treated in the same manner as the micronized pigment (PG-1) to obtain a micronized pigment (PG-3). The volume-average primary particle diameter was 33.0 nm.

[0432] Structural formula (14)

[0433]

[0434] (Micronized pigment (PG-4))

[0435] 500 parts of 98% sulfuric acid, 50 parts of a phthalocyanine pigment represented by the following structural formula (15), and 104.4 parts of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) were added to a three-necked flask and stirred, and the mixture was reacted at 20 °C for 4 hours. Then, the reaction mixture was poured into 5000 parts of ice water at 3 °C, and the precipitated solid was filtered off and washed with water. 500 parts of a 2.5% aqueous sodium hydroxide solution and the residue separated by filtration were added to a beaker and stirred at 80 °C for 1 hour. Then, the mixture was filtered, washed with water, and dried to obtain a pigment in which an average of 8.0 bromine atoms were substituted in the phthalocyanine ring.

[0436] Next, 500 parts of N-methylpyrrolidone, 50 parts of the obtained pigment with an average of 8.0 bromine atoms substituted on the phthalocyanine ring, and 18.2 parts of diphenyl phosphate were added to a three-necked flask, 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 a micronized pigment (PG-4) represented by the following structural formula (16). The volume-average primary particle size of the obtained colorant was 27 nm.

[0437] Structural formula (15)

[0438]

[0439] Structural formula (16)

[0440]

[0441] (Micronized pigment (PG-5))

[0442] 500 parts of N-methylpyrrolidone, 50 parts of the pigment with an average of 8.0 bromine atoms substituted on the phthalocyanine ring prepared in the production of the micronized pigment (PG-4), and 13.8 parts of diphenylphosphinic acid were added to a three-necked flask, 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 a micronized pigment (PG-5) represented by the following structural formula (17). The volume-average primary particle size of the obtained colorant was 31 nm.

[0443] Structural formula (17)

[0444]

[0445] (Micronized pigment (PG-6))

[0446] 500 parts of N-methylpyrrolidone, 50 parts of the pigment with an average of 8.0 bromine atoms substituted on the phthalocyanine ring prepared in the production of the micronized pigment (PG-4), and 21.5 parts of bis(4-nitrophenyl) phosphate were added to a three-necked flask, 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 a micronized pigment (PG-6) represented by the following structural formula (18). The volume-average primary particle size of the obtained colorant was 32 nm.

[0447] Structural formula (18)

[0448]

[0449] (Micronized pigment (PG-7))

[0450] Add 500 parts of 98% sulfuric acid, 50 parts of the phthalocyanine pigment represented by structural formula (15), and 129.3 parts of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) into a three-necked flask and stir, and make it react at 20 °C for 6 hours. Then, pour the reaction mixture into 5000 parts of ice water at 3 °C, filter and separate the precipitated solid and wash it with water. Add 500 parts of 2.5% sodium hydroxide aqueous solution and the residue separated by filtration into a beaker, and stir at 80 °C for 1 hour. Then, filter and separate, wash with water, and dry the mixture to obtain a pigment with an average of 10.1 bromine atoms substituted on the phthalocyanine ring.

[0451] Next, add 500 parts of N-methylpyrrolidone, 50 parts of the obtained pigment with an average of 10.1 bromine atoms substituted on the phthalocyanine ring, and 13.9 parts of diphenyl phosphate into a three-necked flask, heat to 90 °C, and make it react for 8 hours. After cooling it to room temperature, filter the product, wash it with methanol, and then dry it to obtain the micronized pigment (PG-7) represented by the following structural formula (19). The volume average primary particle size of the obtained colorant is 27 nm.

[0452] Structural formula (19)

[0453]

[0454] (Micronized pigment (PG-8))

[0455] Heat 203 parts of aluminum bromide, 47 parts of sodium bromide, and 5 parts of ferrous bromide to melt, and add 50 parts of the phthalocyanine pigment represented by structural formula (15) at 140 °C. Raise the temperature to 160 °C, and while blowing in 215.4 parts of bromine, react at 160 °C for 7 hours. Pour the reaction mixture into 2500 parts of ice water at 3 °C, filter and separate the precipitated solid and wash it with water. Wash the residue in the order of 1% hydrochloric acid aqueous solution, warm water, 1% sodium hydroxide aqueous solution, and warm water, and then dry it to obtain 98 parts of aluminum bromide phthalocyanine. Dissolve the obtained crude aluminum bromide phthalocyanine in 980 parts of concentrated sulfuric acid, and stir at 50 °C for 3 hours. Then, pour the sulfuric acid solution into 9800 parts of ice water at 3 °C, filter and separate the precipitated solid, wash it with water, and dry it. Next, add 500 parts of 2.5% sodium hydroxide aqueous solution and the residue separated by filtration into a beaker, and stir at 80 °C for 1 hour. Then, filter and separate, wash with water, and dry the mixture to obtain a pigment with an average of 15.0 bromine atoms substituted on the phthalocyanine ring.

[0456] Next, 500 parts of N-methylpyrrolidone, 50 parts of the obtained pigment with an average of 11.9 bromine atoms substituted on the phthalocyanine ring, and 10.8 parts of diphenyl phosphate were added to a three-necked flask, heated to 90 °C, and allowed to react for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain a micronized pigment (PG-8) represented by the following structural formula (20). The volume-average primary particle diameter of the obtained colorant was 31 nm.

[0457] Structural formula (20)

[0458]

[0459] (Micronized pigment (PG-9))

[0460] 250 parts of aluminum chloride, 60 parts of sodium chloride, and 2.25 parts of iodine were added to a three-necked flask and stirred at 150 °C for 30 minutes. 50 parts of an aluminum phthalocyanine pigment represented by structural formula (11) was added thereto, and the mixture was stirred at 155 °C for 30 minutes to dissolve it. Further, 58.5 parts of trichloroisocyanuric acid was added, and the mixture was stirred at 190 °C for 5 hours. Then, the reaction mixture was poured into 5000 parts of ice water at 3 °C, and the precipitated solid was filtered off and washed with water. 500 parts of a 2.5% aqueous sodium hydroxide solution and the residue separated by filtration were added to a beaker and stirred at 80 °C for 1 hour. Then, the mixture was filtered, washed with water, and dried to obtain a pigment with an average of 8.1 chlorine atoms substituted on the phthalocyanine ring.

[0461] Next, 500 parts of N-methylpyrrolidone, 50 parts of the obtained pigment with an average of 11.9 bromine atoms substituted on the phthalocyanine ring, and 22.6 parts of diphenyl phosphate were added to a three-necked flask, heated to 90 °C, and allowed to react for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain a micronized pigment (PG-9) represented by the following structural formula (21). The volume-average primary particle diameter of the obtained colorant was 29 nm.

[0462] Structural formula (21)

[0463]

[0464] (Micronized pigments (PY-1 to PY-3))

[0465] Micronized pigments (PY-1 to PY-3) of quinophthalone pigments represented by the following structural formulas (22) to (24) were produced according to the examples of Japanese Patent Application Laid-Open No. 2012-226110. The structures thereof are shown below.

[0466] (Micro-fined Pigment (PY-1))(Micro-fined Pigment (PY-2))(Micro-fined Pigment (PY-3))

[0467]

[0468]

[0469] (Micro-fined Pigment (PY-4))

[0470] Put 100 parts of C.I. Pigment Yellow 138 (PY138) (“Paliotol Yellow K0960-HD” manufactured by BASF Japan Co., Ltd.), 700 parts of sodium chloride, and 180 parts of diethylene glycol into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.), and knead at 80 °C for 6 hours. Put the mixture into 2000 parts of warm water, stir for 1 hour while heating to 80 °C to make it into a slurry state, repeatedly filter and wash with water to remove salt and solvent, and then dry at 80 °C for one day and night to obtain Micro-fined Pigment (PY-4).

[0471] (Micro-fined Pigment (PY-5))

[0472] Put 100 parts of isoindoline-based yellow pigment C.I. Pigment Yellow 139 (“IRGAPHOR Yellow 2R-CF” manufactured by BASF Japan Co., Ltd.), 1600 parts of sodium chloride, and 190 parts of diethylene glycol into a 1-gallon stainless steel kneader, and knead at 60 °C for 10 hours. Then, put the mixture into 3 liters of warm water, stir with a high-speed mixer for about 1 hour while heating to about 80 °C to make it into a slurry state, repeatedly filter and wash with water to remove sodium chloride and solvent, and then dry at 80 °C for 1 day and night to obtain Micro-fined Pigment (PY-5).

[0473] (Micro-fined Pigment (PY-6))

[0474] Put 500 parts of yellow pigment C.I. Pigment Yellow 185 (“Paliotol Yellow D1155” manufactured by BASF Japan Co., Ltd.), 500 parts of sodium chloride, and 250 parts of diethylene glycol into a 1-gallon stainless steel kneader, and knead at 120 °C for 8 hours. Then put the kneaded product into 5 liters of warm water, stir for 1 hour while heating to 70 °C to make it into a slurry state, repeatedly filter and wash with water to remove sodium chloride and diethylene glycol, and then dry at 80 °C for one day and night to obtain Micro-fined Pigment (PY-6).

[0475] (Micro-fine pigment (PY-7))

[0476] Charge 150 parts of a metal complex-based yellow pigment (C.I. Pigment Yellow), 100 parts of "Yellow Pigment E4GN" manufactured by LANXESS, 1600 parts of sodium chloride, and 190 parts of diethylene glycol into a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.), and knead at 60 °C for 10 hours. Next, put the mixture into 3 liters of warm water, heat to about 80 °C while stirring with a high-speed mixer for about 1 hour to make a slurry, repeatedly filter and wash with water to remove sodium chloride and the solvent, and then dry at 80 °C for 1 day and night to obtain a micro-fine pigment (PY-7).

[0477] <Manufacturing method of dye>

[0478] (Resin 1 having a cationic group in the side chain)

[0479] Charge 67.3 parts of methyl ethyl ketone into a four-neck separable flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and heat to 75 °C under a nitrogen gas stream. In addition, make 34.0 parts of methyl methacrylate, 28.0 parts of n-butyl methacrylate, 28.0 parts of 2-ethylhexyl methacrylate, 10.0 parts of dimethylaminoethyl methacrylate, 6.5 parts of 2,2'-azobis(2,4-dimethylvaleronitrile), and 25.1 parts of methyl ethyl ketone uniform and then charge them into a dropping funnel, and install the dropping funnel on the four-neck separable flask, and carry out dropping over 2 hours. 2 hours after the completion of dropping, confirm that the polymerization yield is 98% or more and the weight average molecular weight (Mw) is 6830 based on the non-volatile components, and cool to 50 °C. Add 3.2 parts of chloromethane and 22.0 parts of ethanol thereto, react at 50 °C for 2 hours, then heat to 80 °C over 1 hour, and further react for 2 hours. Thus, resin 1 having a cationic group in the side chain having an ammonium group with a resin content of 47% by mass is obtained. The ammonium salt value of the obtained resin is 34 mgKOH / g.

[0480] (Dye (RD-1))

[0481] Manufacture a salt-forming compound, i.e., dye (RD-1), including C.I. Acid Red 52 and resin 1 having a cationic group in the side chain in the following order.

[0482] To 2000 parts of water, 30 parts of a resin 1 having a cationic group in the side chain, calculated as non-volatile components, was added. After thorough stirring and mixing, the mixture was heated to 60 °C. On the other hand, an aqueous solution was prepared by dissolving 10 parts of C.I. Acid Red 52 in 90 parts of water, and this was added dropwise little by little to the above resin solution. After the dropwise addition, the mixture was stirred at 60 °C for 120 minutes to allow sufficient reaction. As the confirmation of the reaction endpoint, the reaction solution was dropped onto a filter paper, and the endpoint was judged when the exudation disappeared, and it was determined that a salt-forming compound was obtained. After allowing to cool to room temperature with stirring, suction filtration and washing with water were carried out. For the salt-forming compound remaining on the filter paper, moisture was removed and dried using a dryer to obtain 32 parts of a salt-forming compound of C.I. Acid Red 52 and resin 1 having a cationic group in the side chain, namely dye (RD-1). At this time, the content of the effective pigment component derived from C.I. Acid Red 52 in the dye (RD-1) was 25% by mass.

[0483] <Pigment derivative>

[0484] Regarding the pigment derivative used in the photosensitive coloring composition in this example, it is shown in the following structural formulas (a1-1) to (a1-3).

[0485] Pigment derivative (a1-1)

[0486]

[0487] Pc represents a phthalocyanine skeleton.

[0488] Pigment derivative (a1-2)

[0489]

[0490] Pigment derivative (a1-3)

[0491]

[0492] (Resin type dispersant (a2-1) solution)

[0493] In a reaction vessel including a gas inlet tube, a thermometer, a condenser, and a stirrer, 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of isobutyl methacrylate, 20 parts of benzyl methacrylate, and 50 parts of PGMAc were charged, and the vessel was purged with nitrogen. The reaction vessel was heated and stirred to 50 °C, and 12 parts of 3-mercapto-1,2-propanediol were added. The temperature was raised to 90 °C, and a solution prepared by adding 0.1 part of 2,2′-azobisisobutyronitrile to 90 parts of PGMAc was added while reacting for 7 hours. By measuring the non-volatile content, it was confirmed that 95% of the reaction occurred. 19 parts of pyromellitic dianhydride, 50 parts of PGMAc, 50 parts of cyclohexanone, and 0.4 part of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the reaction was carried out at 100 °C for 7 hours. By measuring the acid value, it was confirmed that more than 98% of the acid anhydride was semi-esterified, and the reaction was terminated. PGMAc was added to dilute the solution so that the non-volatile content became 30%, thereby obtaining a resinous dispersant (a2-1) solution with an acid value of 70 mgKOH / g and a weight-average molecular weight of 8500.

[0494] (Resinous dispersant (a2-2) solution)

[0495] In a reaction apparatus equipped with a gas inlet tube, a condenser, stirring blades, and a thermometer, 30 parts of methyl methacrylate, 30 parts of n-butyl methacrylate, 20 parts of 2-hydroxyethyl methacrylate, and 13.2 parts of tetramethylethylenediamine were charged, and the mixture was stirred at 50 °C for 1 hour while flowing nitrogen to purge the system with nitrogen. Subsequently, 9.3 parts of ethyl 2-bromoisobutyrate, 5.6 parts of cuprous chloride, and 133 parts of PGMAc were charged, and the temperature was raised to 110 °C under a nitrogen stream to initiate the polymerization of the first block (B block). After 4 hours of polymerization, a sample of the polymerization solution was taken and the non-volatile content was measured. Based on the non-volatile content conversion, it was confirmed that the polymerization conversion rate was 98% or more.

[0496] Next, 61 parts of PGMAc and 20 parts of 1,2,2,6,6-pentamethylpiperidinyl methacrylate (manufactured by Hitachi Chemical Co., Ltd., not FANCRYL FA-711MM), which is used as the second block (A block) monomer, were introduced into the reaction apparatus, and stirring was carried out while maintaining a state of 110 °C and a nitrogen atmosphere to continue the reaction. Two hours after the introduction of 1,2,2,6,6-pentamethylpiperidinyl methacrylate, a sample of the polymerization solution was taken for non-volatile content measurement, and based on the non-volatile content conversion, it was confirmed that the polymerization conversion rate of the second block (A block) was 98% or more, and the reaction solution was cooled to room temperature to stop the polymerization. Then, PGMAc was added for dilution to make the non-volatile content 30%, thereby obtaining a solution of a resin-type dispersant (a2-2) having an amine value of 57 mgKOH / g per unit non-volatile content and a number-average molecular weight of 4,500 (Mn).

[0497] (Solution of resin-type dispersant (a2-3))

[0498] Using the production method of the pigment dispersant (1) described in Production Example 1 of Japanese Patent No. 5513691, [(3-(N,N-dimethylamino)propylacrylamide / methoxypolyethylene glycol methacrylate copolymer (23 / 77 mass%)) quaternary compound; quaternization rate 27 mol%] was synthesized, and PGMAc was added for dilution to make the non-volatile content 30%, thereby preparing a solution of a resin-type dispersant (a2-3).

[0499] <Manufacturing method of alkali-soluble resin>

[0500] (Preparation of alkali-soluble resin (B-1))

[0501] 196 parts of cyclohexanone was charged into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, a dropping tube, and a stirring device in a separable four-necked flask, and the temperature was raised to 80 °C. After replacing the inside of the reaction vessel with nitrogen, a mixture of 20.0 parts of benzyl methacrylate, 17.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, 20.7 parts of p-cumylphenol ethylene oxide-modified acrylate ("Aronix M110" manufactured by Toagosei Co., Ltd.), and 1.1 parts of 2,2'-azobisisobutyronitrile was dropped from the dropping tube over 2 hours. After the dropping was completed, the reaction was further continued for 3 hours to obtain a solution of the resin.

[0502] After cooling to room temperature, PGMAc was added to make the non-volatile content 20% by mass to prepare a solution of alkali-soluble resin (B-1). The weight-average molecular weight (Mw) was 26,000, and the non-volatile content acid value was 91 mgKOH / g.

[0503] (Preparation of alkali-soluble resin (B-2) (alkali-soluble resin (III)))

[0504] Charge 207 parts of cyclohexanone into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, a dropping tube and a stirring device in a separable four-necked flask, heat up to 80 °C, after purging the inside of the reaction vessel with nitrogen, dropwise add a mixture of 20 parts of methacrylic acid, 20 parts of benzyl methacrylate, 20 parts of p-cumylphenol ethylene oxide-modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 25 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate and 1.33 parts of 2,2'-azobisisobutyronitrile from the dropping tube over 2 hours. After the dropping is completed, continue the reaction for another 3 hours to obtain a copolymer resin solution. Then, with respect to the total amount of the obtained copolymer solution, while stopping the nitrogen and injecting drying gas for 1 hour while stirring, after cooling to room temperature, dropwise add a mixture of 6.5 parts of 2-methacryloyloxyethyl isocyanate (Karenz MOI manufactured by Showa Denko KK), 0.08 part of dibutyltin dilaurate and 26 parts of cyclohexanone at 70 °C over 3 hours. After the dropping is completed, continue the reaction for another 1 hour to obtain a solution of the resin. Add cyclohexanone to make the non-volatile content 20% by mass, thereby preparing an alkali-soluble resin (B-2) solution. The weight average molecular weight (Mw) is 18,000, and the acid value of the non-volatile content is 130 mgKOH / g.

[0505] (Preparation of alkali-soluble resin (B-3) (alkali-soluble resin (I)))

[0506] Put 100 parts of PGMAc into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube and a stirring device in a separable four-necked flask, heat up to 120 °C while injecting nitrogen into the vessel, and dropwise add a mixture of 5.2 parts of styrene, 35.5 parts of glycidyl methacrylate, 41.0 parts of dicyclopentanyl methacrylate and 1.0 part of azobisisobutyronitrile from the dropping tube at the above temperature over 2.5 hours to carry out a polymerization reaction. Then, replace the air inside the flask, put 0.3 part of tris-dimethylaminomethylphenol and 0.3 part of hydroquinone into 17.0 parts of acrylic acid, and continue the reaction at 120 °C for 5 hours, and end the reaction when the acid value of the non-volatile content = 0.8, thereby obtaining a resin solution with a weight average molecular weight of about 12,000 (measured by GPC). Then add 30.4 parts of tetrahydrophthalic anhydride and 0.5 part of triethylamine, and end the reaction after reacting at 120 °C for 4 hours. Add PGMAc to make the non-volatile content 20%, thereby preparing an alkali-soluble resin (B-3) solution. The acid value of the non-volatile content is 88 mgKOH / g.

[0507] (Preparation of alkali-soluble resin (B-4) (alkali-soluble resin (II)))

[0508] 182 g of PGMAc was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen inlet tube. After setting the internal environment of the flask from air to nitrogen, the temperature was raised to 100 °C. Then, a solution prepared by adding 3.6 g of azobisisobutyronitrile to a mixture containing 70.5 g (0.40 mol) of benzyl methacrylate, 43.0 g (0.5 mol) of methacrylic acid, 22.0 g (0.10 mol) of monomethacrylate with a tricyclodecane skeleton (FA-513M manufactured by Hitachi Chemical Co., Ltd.), and 136 g of PGMAc was added dropwise from the dropping funnel to the flask over 2 hours. Furthermore, stirring was continued at 100 °C for 5 hours. Next, the internal environment of the flask was set from nitrogen to air, and 35.5 g [0.25 mol, (50 mol% relative to the carboxyl group of methacrylic acid used in this reaction)] of glycidyl methacrylate, 0.9 g of tri-dimethylaminomethylphenol, and 0.145 g of hydroquinone were added to the flask. After reacting continuously at 110 °C for 6 hours, the reaction was terminated. Cyclohexanone was added to make the non-volatile content 20% by mass, thereby obtaining an alkali-soluble resin (B-4) solution. The weight-average molecular weight was 13,000, the molecular weight distribution (Mw / Mn) was 2.1, and the non-volatile content acid value was 79 mg KOH / g.

[0509] (Preparation of alkali-soluble resin (B-5) (alkali-soluble resin (I)))

[0510] 100 parts of PGMAc was placed in a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, and a stirring device in a separable four-necked flask. While injecting nitrogen into the vessel, the temperature was raised to 120 °C. At this temperature, a mixture of 7.6 parts of styrene, 35.7 parts of glycidyl methacrylate, 42.4 parts of dicyclopentenyl oxyethyl methacrylate, and 0.6 part of azobisisobutyronitrile was added dropwise from the dropping tube over 2.5 hours to carry out a polymerization reaction.

[0511] Next, the inside of the flask was purged with air. 0.3 part of tri-dimethylaminomethylphenol and 0.3 part of hydroquinone were added to 17.2 parts of acrylic acid, and the reaction was continued at 120 °C for 5 hours. The reaction was terminated when the non-volatile content acid value = 0.8, thereby obtaining a resin solution with a weight-average molecular weight of approximately 20,000 (measured by GPC). Furthermore, 22.7 parts of succinic acid and 0.6 part of triethylamine were added, and the reaction was terminated after reacting at 120 °C for 4 hours. PGMAc was added to make the non-volatile content 20%, thereby preparing an alkali-soluble resin (B-5) solution. The non-volatile content acid value was 98 mg KOH / g.

[0512] (Preparation of alkali-soluble resin (B-6) (alkali-soluble resin (I)))

[0513] Put 100 parts of PGMAc into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, and a stirring device in a separable four-necked flask. While injecting nitrogen into the vessel, heat it to 120 °C. At this temperature, a mixture of 8.1 parts of styrene, 30.1 parts of glycidyl methacrylate, 41.0 parts of isobornyl acrylate, and 1.3 parts of azobisisobutyronitrile was added dropwise from a dropping tube over 2.5 hours to carry out a polymerization reaction.

[0514] Next, the air in the flask was replaced. 0.3 part of tris-dimethylaminomethylphenol and 0.3 part of hydroquinone were added to 14.4 parts of acrylic acid, and the reaction was continued at 120 °C for 5 hours. The reaction was terminated when the acid value of the non-volatile component was 0.8, thereby obtaining a resin solution with a weight-average molecular weight of about 9,000 (measured by GPC). Further, 22.1 parts of tetrahydrophthalic anhydride and 0.4 part of triethylamine were added, and the reaction was terminated after reacting at 120 °C for 4 hours. PGMAc was added to make the non-volatile component 20%, thereby preparing an alkali-soluble resin (B-6) solution. The acid value of the non-volatile component was 68 mgKOH / g.

[0515] (Preparation of alkali-soluble resin (B-7) (alkali-soluble resin (I)))

[0516] Put 100 parts of PGMAc into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, and a stirring device in a separable four-necked flask. While injecting nitrogen into the vessel, heat it to 120 °C. At this temperature, a mixture of 3.0 parts of styrene, 46.1 parts of glycidyl methacrylate, 29.3 parts of 1-adamantyl methacrylate, and 0.9 part of azobisisobutyronitrile was added dropwise from a dropping tube over 2.5 hours to carry out a polymerization reaction.

[0517] Next, the air in the flask was replaced. 0.4 part of tris-dimethylaminomethylphenol and 0.4 part of hydroquinone were added to 22.6 parts of acrylic acid, and the reaction was continued at 120 °C for 5 hours. The reaction was terminated when the acid value of the non-volatile component was 0.8, thereby obtaining a resin solution with a weight-average molecular weight of about 14,000 (measured by GPC). Further, 45.7 parts of tetrahydrophthalic anhydride and 0.8 part of triethylamine were added, and the reaction was terminated after reacting at 120 °C for 4 hours. PGMAc was added to make the non-volatile component 20%, thereby preparing an alkali-soluble resin (B-7) solution. The acid value of the non-volatile component was 112 mgKOH / g.

[0518] (Preparation of alkali-soluble resin (B-8))

[0519] Into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, and a stirring device in a separable four-necked flask, 100 parts of PGMAc was placed. While injecting nitrogen into the vessel, it was heated to 120 °C. At this temperature, a mixture of 4.6 parts of styrene, 31.9 parts of glycidyl methacrylate, 36.7 parts of dicyclopentanyl methacrylate, and 0.9 part of azobisisobutyronitrile was added dropwise from a dropping funnel over 2.5 hours to carry out a polymerization reaction.

[0520] Next, the inside of the flask was purged with air. 0.3 part of tris-dimethylaminomethylphenol and 0.3 part of hydroquinone were added to 15.2 parts of acrylic acid, and the reaction was continued at 120 °C for 5 hours. The reaction was terminated when the acid value of the non-volatile components was 0.8, thereby obtaining a resin solution having a weight average molecular weight of about 12,000 (measured by GPC). Further, 45.7 parts of tetrahydrophthalic anhydride and 0.8 part of triethylamine were added, and the reaction was terminated after 4 hours at 120 °C. PGMAc was added to make the non-volatile components 20%, thereby preparing a solution of an alkali-soluble resin (B-7). The acid value of the non-volatile components was 112 mgKOH / g.

[0521] (Preparation of alkali-soluble resin (B-9) (alkali-soluble resin (II)))

[0522] 182 g of PGMAc was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen inlet tube. After setting the inside of the flask from air to nitrogen, the temperature was raised to 100 °C. Then, a solution prepared by adding 3.3 g of azobisisobutyronitrile to a mixture containing 20.5 g of benzyl methacrylate, 89.5 g of methacrylic acid, 24.6 g of dicyclopentenoxyethyl methacrylate, and 136 g of PGMAc was added dropwise from the dropping funnel into the flask over 2 hours. Further, stirring was continued at 100 °C for 5 hours. Next, the inside of the flask was set from nitrogen to air, 70.0 g of glycidyl methacrylate, 1.8 g of tris-dimethylaminomethylphenol, and 0.3 g of hydroquinone were added to the inside of the flask, and the reaction was continued at 110 °C for 6 hours and then terminated. Cyclohexanone was added to make the non-volatile components 20% by mass, thereby obtaining a solution of an alkali-soluble resin (B-4). The weight average molecular weight was 14,000, the molecular weight distribution (Mw / Mn) was 2.1, and the acid value of the non-volatile components was 148 mgKOH / g.

[0523] (Preparation of alkali-soluble resin (B-10))

[0524] 182 g of PGMAc was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen inlet tube. After setting the internal environment of the flask from air to nitrogen, the temperature was raised to 100 °C. Then, a solution prepared by adding 3.6 g of azobisisobutyronitrile to a mixture containing 71.8 g of benzyl methacrylate, 43.8 g of methacrylic acid, 22.4 g of cyclohexyl methacrylate, and 136 g of PGMAc was added dropwise from the dropping funnel to the flask over 2 hours. Furthermore, stirring was continued at 100 °C for 5 hours. Subsequently, the internal environment of the flask was set from nitrogen to air, 36.1 g of glycidyl methacrylate, 0.9 g of tris-dimethylaminomethylphenol, and 0.2 g of hydroquinone were added to the flask, and the reaction was continued at 110 °C for 6 hours and then terminated. Cyclohexanone was added to make the non-volatile content 20% by mass, thereby obtaining a solution of an alkali-soluble resin (B-4). The weight-average molecular weight was 13,000, the molecular weight distribution (Mw / Mn) was 2.1, and the acid value of the non-volatile content was 79 mg KOH / g.

[0525] <Method for producing pigment dispersion>

[0526] [Preparation of blue pigment dispersion (M-B1)]

[0527] After uniformly stirring and mixing the mixture having the following composition, it was dispersed for 5 hours using zirconia beads with a diameter of 1 mm and an eiger mill (manufactured by Eiger Japan Co., Ltd., "mini model M-250MKII"), and then filtered through a 5-μm filter to prepare a blue pigment dispersion (M-B1).

[0528]

[0529] [Preparation of blue pigment dispersion (M-B2)]

[0530] A blue pigment dispersion (M-B2) was prepared in the same manner as the blue pigment dispersion (M-B1), except that the micronized pigment (PB-1) was replaced with the micronized pigment (PB-2).

[0531] [Preparation of green pigment dispersion (M-G1)]

[0532] After uniformly stirring and mixing the mixture having the following composition, it was dispersed for 5 hours using zirconia beads with a diameter of 1 mm and an eiger mill (manufactured by Eiger Japan Co., Ltd., "mini model M-250MKII"), and then filtered through a 5-μm filter to prepare a green pigment dispersion (M-G1).

[0533]

[0534] [Preparation of Green Pigment Dispersion (M-G2)]

[0535] After uniformly stirring and mixing the mixture with the following composition, zirconia beads with a diameter of 1 mm were used and dispersed for 5 hours using an Eiger mill (the "Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5-μm filter to produce the green pigment dispersion (M-G2).

[0536]

[0537]

[0538] [Preparation of Green Pigment Dispersion (M-G3)]

[0539] After uniformly stirring and mixing the mixture with the following composition, zirconia beads with a diameter of 1 mm were used and dispersed for 5 hours using an Eiger mill (the "Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5-μm filter to produce the green pigment dispersion (M-G3).

[0540]

[0541] [Preparation of Yellow Pigment Dispersion (M-Y1)]

[0542] After uniformly stirring and mixing the mixture with the following composition, zirconia beads with a diameter of 1 mm were used and dispersed for 5 hours using an Eiger mill (the "Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5-μm filter to produce the yellow pigment dispersion (M-Y1).

[0543]

[0544] [Preparation of Yellow Pigment Dispersion (M-Y2)]

[0545] The yellow pigment dispersion (M-Y2) was prepared in the same manner as the yellow pigment dispersion (M-Y1), except that the micronized pigment (PY-7) was replaced with an equal amount mixture of the micronized pigment (PY-5) and the micronized pigment (PY-6).

[0546] [Preparation of Red Pigment Dispersion (M-R1)]

[0547] After uniformly stirring and mixing the following mixture, zirconia beads with a diameter of 1 mm were used and dispersed for 5 hours using an Eiger mill (the "Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5-μm filter to produce a red pigment dispersion (M-R1).

[0548]

[0549]

[0550] [Preparation of Black Pigment Dispersion (M-BK1)]

[0551] After uniformly stirring and mixing the following mixture, zirconia beads with a diameter of 1 mm were used and dispersed for 5 hours using an Eiger mill (the "Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5-μm filter to produce a black pigment dispersion (M-BK1).

[0552]

[0553] Regarding other materials used in the photosensitive coloring composition in this example, they are shown below.

[0554] [Photoinitiator (A)]

[0555] (A1): Compound No. 3

[0556] (A2): Compound No. 5

[0557] (A3): Compound No. 6

[0558] (A4): Compound No. 8

[0559] (A5): An equimolar mixture of (A1) to (A4)

[0560] [Photoinitiator (Y)]

[0561] (Y-1): An equimolar mixture of 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one [Omnirad 907 (manufactured by IGM Resins)] and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one [Omnirad 369 (manufactured by IGM Resins)]

[0562] (Y-2): 2,4,6-Trimethylbenzoyl-diphenyl-phosphine oxide [Omnirad TPO (manufactured by IGM Resins)]

[0563] (Y-3): 2,2'-Bis(o-chlorophenyl)-4,5,4',5'-tetraphenyl-1,2'-biimidazole [Biimidazole (manufactured by Kuroishi Kasei Co., Ltd.)]

[0564] (Y-4): An equimolar mixture of 1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2-(O-benzoyloxime) [Irgacure OXE01 (manufactured by BASF Japan Ltd.)] and ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetoxime) [Irgacure OXE02 (manufactured by BASF Japan Ltd.)].

[0565] [Photopolymerizable compound (C)]

[0566] An equimolar mixture of C1, Aronix M310 manufactured by Toagosei Co., Ltd., Aronix M520 manufactured by Toagosei Co., Ltd., and KAYARAD DPCA-30 manufactured by Nippon Kayaku Co., Ltd., prepared as follows.

[0567] (Manufacture of photopolymerizable monomer (C1))

[0568] Charge 801 parts of dipentaerythritol pentaacrylate, 128 parts of hexamethylene diisocyanate, 1.0 part of N,N-dimethylbenzylamine, and 1.0 part of 4-methoxyphenol into a 2 L four-necked flask, react at 70 °C for 8 hours, and confirm the disappearance of the absorption of isocyanate by IR analysis. After cooling to room temperature, charge 70.3 parts of mercaptopropionic acid and react at 50 °C to 60 °C for 6 hours to obtain a photopolymerizable monomer (C1). The acid value of the photopolymerizable monomer (C1) is 43, the urethane group number is 1.53 mmol / g, and the double bond group number is 6.88 mmol / g.

[0569] [Sensitizer (E)]

[0570] An equimolar mixture of 2,4-diethylthioxanthone [KAYACURE DETX-S (manufactured by Nippon Kayaku Co., Ltd.)] and 4,4'-bis(diethylamino)benzophenone [CHEMARK DEABP (manufactured by Chemark Chemical Co., Ltd.)].

[0571] [Polyfunctional mercaptan (F)]

[0572] An equimolar mixture of trimethylolpropane tris(3-mercaptobutyrate) [TPMB (manufactured by Showa Denko K.K.)] and pentaerythritol tetra(3-mercaptopropionate) [PEMP (manufactured by Sakai Chemical Industry Co., Ltd.)].

[0573] [Thermosetting compound solution]

[0574] Dissolve 30 parts by mass of an equimolar mixture of 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2'-bis(hydroxymethyl)-1-butanol [EHPE-3150 (manufactured by Daicel Corporation)] and glycidyl etherified epoxy compound of sorbitol [DENACOL EX611 (manufactured by Nagase ChemteX Corporation)] in 70 parts by mass of PGMAc.

[0575] [Antioxidant (H)]

[0576] An equimolar mixture of Irganox 1010 manufactured by BASF Japan Ltd., Adekastab LA-52 manufactured by ADEKA Corporation, Adekastab PEP-36 manufactured by ADEKA Corporation, and Adekastab AO-412S manufactured by ADEKA Corporation.

[0577] [Ultraviolet absorber (I)]

[0578] An equimolar mixture of Tinuvin P manufactured by BASF Japan Ltd., Tinuvin 405 manufactured by BASF Japan Ltd., and KEMISORB 10 manufactured by Chemipro Kasei Co., Ltd.

[0579] [Polymerization inhibitor (J)]

[0580] An equimolar mixture of 3-methylcatechol, methylhydroquinone, and tert-butylhydroquinone.

[0581] [Silane coupling agent (K)]

[0582] An equimolar mixture of 3-glycidoxypropyltriethoxysilane, 3-methacryloxypropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane.

[0583] [Leveling agent (L)]

[0584] A mixed solution prepared by dissolving 1 part of "BYK-330" manufactured by BYK-Chemie, 0.5 part of "Megafac F-551" manufactured by DIC, and 0.5 part of "Emulgen 103" manufactured by Kao Corporation in 98 parts of PGMAc.

[0585] [Organic solvent]

[0586] A mixed solution with a mass ratio of PGMAc, cyclohexanone, ethyl 3-ethoxypropionate, 1,3-butanediol diacetate, and 3-methoxy-1-butanol of 3:1:1:1:1.

[0587] [Examples 1 to 32 and Comparative Examples 1 to 3] (Preparation of photosensitive coloring compositions (R-B1 to R-B27, R-G1 to R-G4, R-R1 to R-R3, R-BK1))

[0588] Mix and stir each material according to the formulation ratios shown in Tables 1 to 5, and filter through a 1-μm filter to obtain photosensitive coloring compositions of various colors.

[0589] [Table 1]

[0590]

[0591] [Table 2]

[0592]

[0593] [Table 3]

[0594]

[0595] [Table 4]

[0596]

[0597] [Table 5]

[0598]

[0599] The obtained photosensitive coloring compositions were evaluated by the following method. The results are shown in Tables 6 to 10. The meanings of the evaluation grades are as follows.

[0600] 4: Extremely good;

[0601] 3: Good;

[0602] 2: Practically applicable;

[0603] 1: Not suitable for practical use

[0604] [Pattern formation]

[0605] The obtained photosensitive coloring composition was applied onto a glass substrate (EAGLE 2000 manufactured by Corning Inc.) measuring 100 mm in length × 100 mm in width and 0.7 mm in thickness by spin coating. After that, it was heated in a clean oven at 70 °C for 15 minutes to remove the solvent, thereby obtaining a film of approximately 2 μm. Then, after cooling the substrate to room temperature, using a high-pressure mercury lamp, through a photomask with stripe patterns of 100 μm in width (pitch 200 μm) and 10 μm in width (pitch 20 μm), with an illuminance of 20 mW / cm 2 , 50 mJ / cm 2 exposure was carried out. Then, after spray-developing the substrate using an aqueous developer at 23 °C containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide, it was washed with ion-exchanged water and air-dried, and then heated in a clean oven at 230 °C for 30 minutes. Spray development was carried out for the film in each photosensitive coloring composition within the shortest time capable of forming a pattern without development residue, and this was regarded as the appropriate development time.

[0606] The film thickness of the film was measured using a Dektak 3030 (manufactured by Japan Vacuum Technology Co., Ltd.).

[0607] [Linearity evaluation]

[0608] The pattern formed by the above method was observed and evaluated using an ECLIPSE LV100POL model optical microscope manufactured by Nikon Corporation. The evaluation criteria are as follows.

[0609] 4: The difference between the maximum and minimum line widths is less than 1 μm

[0610] 3: The difference between the maximum and minimum line widths is 1 μm or more and less than 2 μm

[0611] 2: The difference between the maximum and minimum line widths is 2 μm or more and less than 3 μm

[0612] 1: The difference between the maximum and minimum line widths is 3 μm or more

[0613] [Resolution evaluation]

[0614] The pattern formed by the above method was observed and evaluated using an ECLIPSE LV100POL model optical microscope manufactured by Nikon Corporation. The evaluation criteria are as follows. Poor resolution means that adjacent stripe patterns are connected or there are missing parts. The evaluation criteria are as follows.

[0615] 4: Portions where there are no connected patterns or missing parts

[0616] 3: Portions where the connected or missing patterns are less than 5% of the whole

[0617] 2: Portions where the connected or missing patterns are more than 5% and less than 20% of the whole

[0618] 1: Portions where the connected or missing patterns are 20% or more of the whole

[0619] [Residual film rate evaluation]

[0620] In the formation of the pattern, spray development and cleaning with ion-exchanged water are carried out, and the film thickness after air drying is measured. The film thickness is set as the film thickness after development. Then, it is heated at 230 °C for 30 minutes in a clean oven, and the film thickness at the same location where the film thickness before development is measured is measured. The film thickness is taken as the film thickness after baking. The residual film rate is calculated by the following mathematical formula based on the two film thicknesses. The evaluation is carried out as follows.

[0621] Mathematical formula: Residual film rate (%) = Film thickness after baking ÷ Film thickness after development × 100

[0622] 4: Residual film rate is 90% or more

[0623] 3: Residual film rate is more than 85% and less than 90%

[0624] 2: Residual film rate is more than 80% and less than 85%

[0625] 1: Residual film rate is less than 80%

[0626] [Watermark evaluation]

[0627] For the obtained photosensitive coloring composition, it is coated on a glass substrate (EAGLE 2000 manufactured by Corning) with a length of 100 mm × width of 100 mm and a thickness of 0.7 mm, and pre-baked at 95 °C for 2 minutes using a hot plate ("EC-1200N (trade name)" manufactured by ASONE) to obtain a film with a film thickness of 3.4 μm. Then, through a mask with a stripe pattern having a width of 100 μm, ultraviolet exposure is carried out under the conditions of an illuminance of 20 mW / cm 2 , 40 mJ / cm 2 The conditions are for ultraviolet exposure. Then, it is developed by dipping in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 °C for 40 seconds, cleaned with pure water, and the obtained pattern is observed using an optical microscope of the ECLIPSE LV100POL model manufactured by Nikon Corporation. In addition, the evaluation criteria are as follows.

[0628] 4: Without watermark.

[0629] 3: The watermark covers less than 10% of the entire surface.

[0630] 2: The watermark covers more than 10% but less than 30% of the entire surface.

[0631] 1: The watermark covers 30% or more of the entire surface.

[0632] [Table 6]

[0633]

[0634] [Table 7]

[0635]

[0636] [Table 8]

[0637]

[0638] [Table 9]

[0639]

[0640] [Table 10]

[0641]

[0642] Based on the results of the said table, the photosensitive coloring compositions of Examples 1 to 32 are all at a practical level or above in all evaluations.

[0643] (Experimental Example 2)

[0644] <Colorant (D)>

[0645] (Fine - sized blue pigment (D - 1))

[0646] As the fine - sized blue pigment (D - 1), the fine - sized pigment (PB - 1) of Experimental Example 1 was used.

[0647] (Fine - sized purple pigment (D - 2))

[0648] As the fine - sized purple pigment (D - 2), the fine - sized pigment (PV - 1) of Experimental Example 1 was used.

[0649] (Dye (D - 3))

[0650] As the dye (D - 3), the dye (RD - 1) of Experimental Example 1 was used.

[0651] <Manufacturing Example of Resin - type Dispersant>

[0652] (Resin-type dispersant solution)

[0653] As the resin-type dispersant solution, the resin-type dispersant (a2-1) of Experimental Example 1 was used.

[0654] <Manufacturing Example of Alkali-Soluble Resin (B’)>

[0655] (Alkali-soluble resin (B’-1) solution)

[0656] 196 parts of cyclohexanone was charged into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, a dropping tube and a stirring device in a separable four-necked flask, and the temperature was raised to 80°C. After replacing the inside of the reaction vessel with nitrogen, a mixture of 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, 20.7 parts of p-cumylphenol ethylene oxide-modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.), and 1.1 parts of 2,2'-azobisisobutyronitrile was dropped from the dropping tube over 2 hours. After the dropping was completed, the reaction was continued for 3 hours to obtain a solution of an acrylic resin. After cooling to room temperature, about 2 parts of the resin solution was sampled, heated and dried at 180°C for 20 minutes, and the nonvolatile content was measured. PGMAc was added to the previously synthesized resin solution to make the nonvolatile content 20%, thereby preparing an alkali-soluble resin (B’-1) solution. The weight average molecular weight (Mw) was 26,000.

[0657] (Alkali-soluble resin (B’-2) solution)

[0658] Into a reaction vessel equipped with a thermometer, a condenser, a nitrogen inlet tube, a dropping funnel, and a stirring device in a separable four-necked flask, 207 parts of cyclohexanone was charged. The temperature was raised to 80 °C. After purging the inside of the reaction vessel with nitrogen, a mixture of 20 parts of methacrylic acid, 20 parts of p-cumylphenol ethylene oxide-modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 1.33 parts of 2,2'-azobisisobutyronitrile was added dropwise from the dropping funnel over 2 hours. After completion of the dropwise addition, the reaction was continued for an additional 3 hours to obtain a copolymer resin solution. Next, with respect to the total amount of the copolymer solution obtained, while stopping the nitrogen and injecting dry air for 1 hour with stirring, after cooling to room temperature, a mixture of 6.5 parts of 2-methacryloyloxyethyl isocyanate (Karenz MOI manufactured by Showa Denko K.K.), 0.08 part of dibutyltin dilaurate, and 26 parts of cyclohexanone was added dropwise at 70 °C over 3 hours. After completion of the dropwise addition, the reaction was continued for an additional 1 hour to obtain a solution of an acrylic resin. After cooling to room temperature, about 2 parts of the resin solution was sampled, heated and dried at 180 °C for 20 minutes, and the nonvolatile content was measured. Cyclohexanone was added to the previously synthesized resin solution to make the nonvolatile content 20%, thereby preparing a solution of an alkali-soluble resin (B’-2). The weight average molecular weight (Mw) was 18,000.

[0659] (Solution of alkali-soluble resin (B’-3))

[0660] 370 parts of cyclohexanone were placed in a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen inlet tube, a dropping tube, and a stirring device, and the temperature was raised to 80°C. After nitrogen substitution in the flask, a mixture of 18 parts of p-cumylphenol ethylene oxide-modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 10 parts of benzyl methacrylate, 18.2 parts of glycidyl methacrylate, 25 parts of methyl methacrylate, and 2.0 parts of 2,2'-azobisisobutyronitrile was dropped from the dropping tube over 2 hours. After the dropwise addition, the mixture was further reacted at 100°C for 3 hours, and then 1.0 parts of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was continued at 100°C for 1 hour. Next, the container was replaced with air, 0.5 parts of tri-dimethylaminophenol and 0.1 parts of hydroquinone were added to 9.3 parts of acrylic acid (100% of glycidyl groups) in the container, and the reaction was continued at 120°C for 6 hours. The reaction was terminated when the acid value of the non-volatile component reached 0.5, thereby obtaining a solution of acrylic resin. Furthermore, 19.5 parts of tetrahydrophthalic anhydride (100% of the generated hydroxyl groups) and 0.5 parts of triethylamine were added, and the reaction was continued at 120°C for 3.5 hours to obtain a solution of acrylic resin. After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180°C for 20 minutes, and the non-volatile component was measured. PGMAc was added to the previously synthesized resin solution so that the non-volatile component became 20% by mass, thereby preparing an alkali-soluble resin (B'-3) solution. The weight average molecular weight (Mw) was 19,000.

[0661] (Alkali-soluble resin (B'-4) solution)

[0662] A separable flask with a cooling tube was prepared as a reaction vessel, and on the other hand, as a monomer dropping vessel, 40 parts of dimethyl-2,2'-[oxybis(methylene)]bis-2-propionate, 40 parts of methacrylic acid, 120 parts of methyl methacrylate, 4 parts of tert-butylperoxy-2-ethylhexanoate ("PERBUTYL O" manufactured by NOF Corporation), and 40 parts of PGMAc were prepared by sufficiently stirring and mixing. As a chain transfer agent dropping vessel, 8 parts of n-dodecyl mercaptan and 32 parts of PGMAc were prepared by sufficiently stirring and mixing.

[0663] 395 parts of PGMAc was charged into the reaction tank. After purging with nitrogen, it was heated with an oil bath while stirring to raise the temperature of the reaction tank to 90 °C. After the temperature of the reaction tank stabilized at 90 °C, dropping began from the monomer dropping tank and the chain transfer agent dropping tank. The dropping was carried out while maintaining the temperature at 90 °C for 135 minutes respectively. Sixty minutes after the dropping ended, the temperature was raised to make the reaction tank reach 110 °C. After maintaining 110 °C for 3 hours, a gas inlet tube was installed on a separable flask, and bubbling of an oxygen / nitrogen = 5 / 95 (volume ratio) mixed gas was started. Then, 70 parts of glycidyl methacrylate, 0.4 part of 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and 0.8 part of triethylamine were charged into the reaction tank, and the reaction was carried out at 110 °C for 12 hours while maintaining this state. Then, 150 parts of PGMAc was added and cooled to room temperature. About 2 g of the resin solution was sampled, heated and dried at 180 °C for 20 minutes, and the non-volatile content was measured. PGMAc was added to the previously synthesized resin solution to make the non-volatile content 20 mass%, thereby obtaining a solution of an alkali-soluble resin (B’-4). The weight-average molecular weight of the resin was 18,000, and the acid value per unit non-volatile content was 2 mgKOH / g.

[0664] <Manufacture of Dispersion>

[0665] (Dispersion 1)

[0666] After the following raw materials were stirred and mixed to be uniform, zirconia beads with a diameter of 0.5 mm were used and dispersed for 3 hours with an eiger mill (the "mini model M-250MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a filter with a pore size of 1.0 μm to produce Dispersion 1.

[0667]

[0668] <Manufacturing Method of Photosensitive Coloring Composition>

[0669] [Example 1]

[0670] (Photosensitive Coloring Composition 1)

[0671] The following raw materials were mixed and stirred, and filtered through a filter with a pore size of 1.0 μm to obtain Photosensitive Coloring Composition 1.

[0672]

[0673]

[0674] [Examples 2 to 33, Comparative Examples 1 to 5] (Photosensitive Coloring Compositions 2 to 38)

[0675] Except for changing the photosensitive coloring composition 1 of Example 1 to the raw materials and amounts described in Tables 11 to 14, photosensitive coloring compositions 2 to 38 were prepared in the same manner as in Example 1.

[0676] [Table 11]

[0677]

[0678] [Table 12]

[0679]

[0680] [Table 13]

[0681]

[0682] [Table 14]

[0683]

[0684] In addition, regarding each raw material, it is as described below.

[0685] [Alkali-Soluble Resin (B’) Solution]

[0686] The alkali-soluble resin (B’) solution was prepared by mixing the solutions of alkali-soluble resins (B’-2) to (B’-4) in the same amount respectively.

[0687] [Photopolymerizable Compound (C)]

[0688] (Polymerizable Compound (C-1) having a structure derived from ε-caprolactone)

[0689] C-1-1: KAYARAD DPCA-20 (manufactured by Nippon Kayaku Co., Ltd.)

[0690] C-1-2: KAYARAD DPCA-30 (manufactured by Nippon Kayaku Co., Ltd.)

[0691] C-1-3: KAYARAD DPCA-60 (manufactured by Nippon Kayaku Co., Ltd.)

[0692] (Polymerizable Compound (C-2) having an acid group)

[0693] C-2-1: Aronix M-520 (manufactured by Toagosei Co., Ltd.)

[0694] (Other Polymerizable Compound (C-3))

[0695] C-3-1: Aronix M-402 (manufactured by Toagosei Co., Ltd.)

[0696] [Photoinitiator (A)]

[0697] (Photoinitiator (A-1))

[0698] A-1-1: The compound of the formula (1)

[0699] A-1-2: The compound of the formula (2)

[0700] A-1-3: The compound of the formula (3)

[0701] A-1-4: The compound of the formula (4)

[0702] A-1-5: The compound of the formula (5)

[0703] A-1-6: The compound of the formula (6)

[0704] (Photoinitiator (A-2))

[0705] A-2-1: The compound of the formula (7)

[0706] A-2-2: The compound of the formula (8)

[0707] A-2-3: The compound of the formula (9)

[0708] A-2-4: The compound of the formula (10)

[0709] A-2-5: The compound of the formula (11)

[0710] (Photoinitiator (A-3))

[0711] A-3-1: "Omnirad 369" (manufactured by IGM Resins, acetophenone-based compound)

[0712] A-3-2: "Omnirad TPO" (manufactured by IGM Resins, acylphosphine oxide-based compound)

[0713] A-3-3: 2,2'-Bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (imidazole-based compound)

[0714] A-3-4: IRGACURE OXE01 (manufactured by BASF Japan, oxime-based compound)

[0715] A-3-5: IRGACURE OXE02 (manufactured by BASF Japan Ltd., an oxime-based compound)

[0716] A-3-6: IRGACURE OXE04 (manufactured by BASF Japan Ltd., an oxime-based compound)

[0717] [Sensitizer (E)]

[0718] E-1-1: KAYACURE DETX-S (manufactured by Nippon Kayaku Co., Ltd., a thioxanthone-based compound)

[0719] E-2-1: CHEMARK DEABP (manufactured by Chemark Chemical Co., Ltd., a benzophenone-based compound)

[0720] (Antioxidant (H))

[0721] H-1: IRGANOX 1010 (manufactured by BASF Japan Ltd., a hindered phenol-based antioxidant)

[0722] H-2: Adekastab 2112 (manufactured by ADEKA Co., Ltd., a phosphorus-based antioxidant)

[0723] Above, antioxidant (L) is prepared by mixing antioxidant (H-1) and antioxidant (H-2) in the same amount respectively.

[0724] (Leveling agent (L))

[0725] A solution prepared by dissolving 2 parts of "BYK-330" manufactured by BYK-Chemie GmbH in 98 parts of PGMAc.

[0726] (Adhesion improver)

[0727] 1: Silane coupling agent KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd.)

[0728] 2: Silane coupling agent KBE-503 (manufactured by Shin-Etsu Chemical Co., Ltd.)

[0729] Above, the adhesion improver is prepared by mixing adhesion improver (1) and adhesion improver (2) in the same amount respectively.

[0730] [Evaluation of photosensitive coloring composition]

[0731] For the obtained photosensitive coloring composition, the following methods are used for linearity evaluation, cross-sectional shape evaluation, and residual film rate evaluation for watermark evaluation and pattern shape evaluation. The evaluation results are shown in Tables 11 to 14.

[0732] [Pattern formation]

[0733] Patterns are formed under the same conditions as in Experimental Example 1.

[0734] (Pattern shape evaluation 1: Linearity evaluation)

[0735] For the patterns formed by the above method, using an ECLIPSE LV100POL model optical microscope manufactured by Nikon Corporation, measure the maximum and minimum widths of 10 stripe patterns and calculate their average to conduct the evaluation. A value of 3 or more is considered practical.

[0736] 5: The difference between the maximum and minimum line widths is less than 0.5 μm

[0737] 4: The difference between the maximum and minimum line widths is 0.5 μm or more and less than 1.5 μm

[0738] 3: The difference between the maximum and minimum line widths is 1.5 μm or more and less than 2.5 μm

[0739] 2: The difference between the maximum and minimum line widths is 2.5 μm or more and less than 3.5 μm

[0740] 1: The difference between the maximum and minimum line widths is 3.5 μm or more

[0741] (Pattern shape evaluation 2: Cross-sectional shape evaluation)

[0742] For the patterns formed by the above method, use a scanning electron microscope ("S-3000H" manufactured by Hitachi High-Technologies Corporation) to confirm the pattern shape. The evaluation is conducted by taking an SEM image of the cross-section of a 100-μm-wide stripe pattern and measuring the taper angle between the substrate and the end of the pattern cross-section for cross-sectional shape evaluation. A value of 3 or more is considered practical.

[0743] 5: The taper angle is 30 degrees or more and less than 50 degrees

[0744] 4: The taper angle is 50 degrees or more and less than 60 degrees

[0745] 3: The taper angle is less than 30 degrees or 60 degrees or more and less than 70 degrees

[0746] 2: The taper angle is 70 degrees or more and less than 90 degrees

[0747] 1: The taper angle is 90 degrees or more

[0748] (Evaluation of residual film rate)

[0749] The residual film rate was calculated under the same conditions as in Experimental Example 1. A value of 3 or more was considered practical. In addition, the film thickness was measured using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).

[0750] Mathematical formula: Residual film rate (%) = Film thickness after baking ÷ Film thickness after development × 100

[0751] 5: Residual film rate is 90% or more

[0752] 4: Residual film rate is 85% or more and less than 90%

[0753] 3: Residual film rate is 80% or more and less than 85%

[0754] 2: Residual film rate is 75% or more and less than 80%

[0755] 1: Residual film rate is less than 70%

[0756] (Watermark evaluation)

[0757] The surface of the pattern was observed under the same conditions as in Experimental Example 1, and the degree of the discolored part was evaluated. A value of 3 or more was considered practical.

[0758] 5: No watermark

[0759] 4: Watermark is less than 10% of the whole

[0760] 3: Watermark is 10% or more and less than 20% of the whole

[0761] 2: Watermark is 20% or more and less than 30% of the whole

[0762] 1: Watermark is 30% or more of the whole

[0763] Based on the results in the above table, the photosensitive coloring compositions of Examples 1 to 33 all had results above the practical level in all evaluations.

Claims

1. A photosensitive coloring composition comprising: a first photoinitiator represented by the following general formula (1), a second photoinitiator different from the first photoinitiator, a binder resin, a photopolymerizable compound, and a colorant. The second photoinitiator includes a third photoinitiator represented by the following general formula (2). The first photoinitiator includes a fourth photoinitiator represented by the following general formula (3). General formula (1) In general formula (1), R1 and R2 each independently represent R 11 or COR 11 , 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. The alkyl portion of the alkyl group, aryl group, arylalkyl group, or heterocyclic group represented by R 11 may be a branched side chain or a cyclic alkyl group. 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. R4 represents a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, or a halogen atom, and n represents 0 or 1. General formula (2) In general formula (2), R1 represents an alkyl group having 4 to 20 carbon atoms with an alicyclic hydrocarbon group. R2 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. R3 represents a hydrogen atom, a nitro group, a group having an ether bond, or an aromatic group. General formula (3) In general formula (3), R4 and R5 each independently represent 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.

2. The photosensitive coloring composition according to claim 1, wherein The binder resin contains an alkali-soluble resin selected from the group consisting of the following (I), (II), and (III), and having a carboxyl group and a polymerizable unsaturated group in a side chain. (I) An alkali-soluble resin obtained by reacting a polybasic acid or polybasic anhydride and a reaction product of an epoxy group in a polymer having an epoxy group with a carboxyl group-containing monomer, and further containing a polycyclic alicyclic monomer unit. (II) An alkali-soluble resin which is a reaction product of a carboxyl group in a polymer having a carboxyl group and a monomer containing an epoxy group, and further contains a polycyclic alicyclic monomer unit. (III) An alkali-soluble resin which is a reaction product of a hydroxyl group in a polymer having a hydroxyl group and a carboxyl group and a monomer containing an isocyanate group.

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

4. The photosensitive coloring composition according to claim 1 or 2, wherein, The second photopolymerization initiator further contains one or more compounds selected from the group consisting of oxime ester compounds, acetophenone compounds, phosphine compounds, and imidazole compounds. The compound is different from the third photopolymerization initiator represented by the general formula (2).

5. The photosensitive coloring composition according to claim 1 or 2, wherein, With respect to 100 parts by mass of the total content of the third photopolymerization initiator and the fourth photopolymerization initiator, the content of the third photopolymerization initiator is 5 parts by mass to 95 parts by mass.

6. The photosensitive coloring composition according to claim 1 or 2, further comprising a fifth photoinitiator different from the first photoinitiator and the second photoinitiator.

7. The photosensitive coloring composition according to claim 1 or 2, wherein, With respect to 100 parts by mass of the total content of the photopolymerization initiators contained in the photosensitive coloring composition, the total content of the third photopolymerization initiator and the fourth photopolymerization initiator is 30 parts by mass or more.

8. The photosensitive coloring composition according to claim 1 or 2, wherein, The polymerizable compound contains a polymerizable compound having a structure derived from a lactone.

9. The photosensitive coloring composition according to claim 1 or 2, wherein, The polymerizable compound contains a polymerizable compound having an acidic group.

10. The photosensitive coloring composition according to claim 1 or 2, further comprising a sensitizer.

11. A color filter, comprising: A substrate; And a light filtering section formed using the photosensitive coloring composition according to any one of claims 1 to 10.

12. An image display device, comprising the color filter according to claim 11.

Images