JP6912237B2 - Color curable resin composition, color filter and display device containing it - Google Patents

Description

The present invention relates to a color curable resin composition, a color filter, and a display device including the same.

A color curable composition containing a colorant dispersion, a polymerizable compound, and a polymerization initiator obtained by dispersing a colorant containing a dye and a pigment, an extender pigment, and a dispersant in a solvent containing propylene glycol monomethyl ether acetate. Is known (Patent Document 1).

JP-A-2015-98590

However, in the colored curable resin composition described in Patent Document 1, there is still room for improvement in solvent resistance and heat resistance.

An object of the present invention is to obtain a color curable resin composition capable of forming a color filter having improved solvent resistance and heat resistance, a color filter formed from the color curable resin composition, and the color filter. To provide a display device including.

The present invention provides the following colored curable resin compositions, color filters and display devices.
[1] Contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and an extender pigment (P).
A color-curable resin composition in which the colorant (A) contains a lake pigment.
[2] The rake pigment comprises a compound (Aa) composed of an anion of a compound containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen, and a cation having a pigment skeleton. The colored curable resin composition according to [1], which comprises.
[3] The colored curable resin composition according to [2], wherein the compound (Aa) is a compound represented by the formula (AI).

[In the formula (AI), X ⁺ represents a cation represented by the formula (AIX). ]

[[Y] ^m- represents an m-valent anion containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus.
m represents an arbitrary natural number.
In the formula (AIX ^{), R 41 to R 44} are monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms and having 2 to 20 carbon atoms, which may have substituents independently of each other. It is an alkyl group and has a group in which an oxygen atom is inserted between methylene groups constituting the alkyl group (however, a plurality of oxygen atoms are not inserted adjacent to each other) and a substituent. It represents a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms, an aralkyl group having 7 to 11 carbon atoms which may have a substituent, or a hydrogen atom.
R ⁴¹ and R ⁴² may be bonded to form a ring with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may be bonded to form a ring with the nitrogen atom to which they are bonded.
R ^{47 to} R ⁵⁴ independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or an alkyl group having 1 to 8 carbon atoms, and when the number of carbon atoms is 2 or more, constitutes the alkyl group. An oxygen atom may be inserted between the methylene groups (however, a plurality of oxygen atoms are not inserted adjacent to each other). R ⁴⁸ and R ⁵² may be combined with each other to form -NH-, -O-, -S- or -SO _2- .
T ¹ represents a monovalent aromatic heterocyclic group which may have a substituent.
When m is a natural number of 2 or more, the plurality of X ⁺ may have the same structure or different structures. ]
[4] The color-curable resin composition according to any one of [1] to [3], wherein the extender pigment (P) is at least one selected from the group consisting of zinc oxide, titanium oxide, silica and zirconia. thing.
[5] A color filter formed from the colored curable resin composition according to any one of [1] to [4].
[6] A display device including the color filter according to [5].

According to the colored curable resin composition according to the present invention, it is possible to provide a color filter having improved solvent resistance and heat resistance, and a display device including the color filter.

<Coloring curable resin composition>
The color-curable resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and an extender pigment (P), and contains a colorant (A). ) Contains a lake pigment.
According to the color curable resin composition of the present invention containing the colorant (A) containing a lake pigment and the extender pigment (P), the solvent resistance and heat resistance of the cured film (color filter, etc.) are improved. Can be done.

Unless otherwise specified, the compounds exemplified as each component in the present specification may be used alone or in combination of two or more.

[1] Colorant (A)
[1-1] Lake Pigment Colorant (A) contains a lake pigment. As used herein, the term rake pigment refers to a pigment in which a dye soluble in water or an organic solvent is insoluble with a rake agent. The pigment has, for example, a solubility (23 ° C.) in propylene glycol monomethyl ether acetate or propylene glycol monomethyl ether of 1% by mass or less.

Examples of dyes that can form rake pigments include acidic dyes, basic dyes, direct dyes, and compounds classified as having hues other than pigments in the Color Index (published by The Society of Dyers and Colorists). , Known dyes described in Dyeing Note (Color Dyeing Co., Ltd.) can be used.

Specific examples of acid dyes include C.I. I. Acid Red 1, 3, 4, 6, 8, 11, 12, 14, 18, 26, 27, 33, 37, 50, 51, 51: 1, 52, 53, 57, 82, 87, 88, 91, 92, 93, 94, 95, 98, 101, 103, 106, 108, 111, 114, 131, 137, 138, 151, 154, 158, 159, 173, 184, 186, 215, 257, 266, 289, 296, 337; C.I. I. Acid Orange 7, 10, 11, 12, 15, 19, 20, 22, 28, 30, 52, 56, 74, 127; C.I. I. Acid Violet 9, 11, 15, 16, 17, 19, 21, 23, 24, 25, 30, 38, 41, 42, 43, 49, 50, 56, 58, 72; C.I. I. Acid Yellow 1, 3, 17, 18, 23, 25, 36, 38, 42, 44, 54, 59, 72, 78, 151; C.I. I. Acid Brown 2, 4, 13, 19, 248; C.I. I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 14, 15, 17, 18, 19, 20, 22, 24, 25, 34, 38, 40, 45, 48, 59, 61, 74, 75, 78, 80, 83, 86, 88, 90, 91, 92, 93, 93: 1, 97, 98, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 121, 123, 126, 127: 1, 129, 142, 145, 147, 167, 213, 230, 269; C.I. I. Acid greens 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 25, 27 and the like can be mentioned.

Specific examples of basic dyes include C.I. I. Basic Red 1, 1: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 14, 15, 17, 22, 23, 25, 27, 29, 30, 32, 34, 37, 38, 39, 46, 46: 1, 51, 52, 53, 54, 55, 62, 64, 76, 82, 90, 94, 118; C.I. I. Basic Orange 1, 2, 4, 5, 14, 15, 16, 17, 18, 21, 22, 23, 24, 25, 29, 30, 33, 54, 69; C.I. I. Basic Violet 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 11: 1, 12, 13, 14, 15, 16, 18, 20, 21, 22, 23, 28, 36, 39; C.I. I. Basic Yellow 1, 2, 3, 5, 6, 7, 9, 11, 11: 1, 13, 14, 15, 19, 20, 21, 23, 24, 25, 28, 29, 32, 36, 37, 38, 39, 40, 41, 45, 49, 51, 52, 53, 57, 62, 73, 80, 90; C.I. I. Basic Brown 1, 16, 17, 18; C.I. I. Basic Blue 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 22, 23, 24, 25, 26, 35, 41, 44, 45, 47, 53, 54, 55, 64, 65, 66, 67, 72, 74, 81, 99, 129; C.I. I. Basic greens 1, 4, 5 and the like can be mentioned.

Specific examples of direct dyes include C.I. I. Direct Blue 41, 77, 86, 87, 106, 107, 108, 109, 189, 190, 199, 264; C.I. I. Direct violet 54 and the like can be mentioned.

Specific examples of the rake agent include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, catanol, tamol, and heteropolyacids (phosphotungstic acid, phosphomolybdic acid, lintangustomolybdate, kei. Examples thereof include tungstic acid, molybdic acid, molybdate molybdic acid, etc.) and isopolyacids (tungstic acid, molybdic acid, etc.).

Specific rake pigments include, for example, C.I. I. Pigment Blue 1, 1: 2, 2, 3, 8, 9, 10, 11, 12, 14, 17: 1, 18, 19, 24, 24: 1, 53, 56, 61, 62, 63, 78; C. I. Pigment Violet 1, 2, 2: 2, 3, 3: 1, 3: 3, 3: 4, 4, 5, 5: 1, 6: 1, 7: 1, 9, 12, 20, 26, 27, 39; C.I. I. Pigment Green 1, 2, 3, 4, 8, 9, 10, 12, 45; C.I. I. Pigment Red 48: 1, 48: 2, 48: 3, 48: 4, 48: 5, 49, 49: 1, 49: 2, 49: 3, 50, 50: 1, 51, 52: 1, 52: 2, 53, 53: 1, 53: 3, 57: 1, 58, 58: 1, 58: 2, 58: 3, 58: 4, 60: 1, 63, 63: 1, 63: 2, 63: 3, 64: 1, 68, 81, 81: 1, 81: 2, 81: 3, 81: 4, 82, 83, 84, 90, 90: 1, 151, 169, 172, 173, 174, 191 193, 200, 237, 239, 247; C.I. I. Pigment Orange 17, 18, 19, 46; C.I. I. Pigment Yellow 18, 61, 61: 1, 62, 100, 104, 115, 133, 168, 169, 183, 191 and 209, 209: 1, 212 and the like.

The lake pigment in the present invention may have a cation derived from the above dye, or may have an anion derived from the above dye. The lake pigment preferably has a cation derived from the above dye.
Examples of the cation derived from the above dye include a cation derived from a triarylmethane dye, a rhodamine dye, and a xanthene dye. The cation derived from the above dye is preferably a triarylmethane dye, more preferably a triarylmethane dye which may have a heterocycle such as a thiazole group.
When the rake pigment has a cation derived from the dye, it usually has an anion having a transition metal atom, a silicon atom, an aluminum atom, a boron atom, a sulfur atom, a halogen atom and the like.
The anions in lake pigment, isopolyacid ion _{(M m1} O ^{n) c-,} heteropoly acid ion ^{_{(X l M m1 O n)}} c- in addition, include the following anions.
(In each formula, M is a poly atom, X is a hetero atom, l is a hetero atom composition ratio, m1 is a poly atom composition ratio, and n is an oxygen atom composition ratio. C is an integer of 1 to 8. show.)

[In the formula, M represents a boron atom or an aluminum atom. R ⁶¹ , R ⁶² , R ⁶³ and R ⁶⁴ each independently represent a hydroxy group, a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or a reactive group. However, ^{at least one of R 61} , R ⁶² , R ⁶³ and R ⁶⁴ is a reactive group. ]

[In the formula (6), W ³ and W ⁴ independently represent a fluorine atom or an alkyl fluoride group having 1 to 4 carbon atoms, or W ³ and W ⁴ are bonded to each other and have 1 carbon atom. Form ~ 4 alkanediyl fluoride groups. ]

[In formula (7), W ⁵ , W ⁶ and W ⁷ represent a fluorine atom or an alkyl fluoride group having 1 to 4 carbon atoms independently of each other. ]

[In formula (8), Y ¹ represents an alkanediyl fluoride group having 1 to 4 carbon atoms. ]

[In formula (9), Y ² represents an alkyl fluoride group having 1 to 4 carbon atoms. ]

From the viewpoint of solvent resistance and heat resistance, rake pigments include tungsten (W), molybdenum (Mo), vanadium (V), titanium (Ti), niobium (Nb), silicon (Si), phosphorus (P), etc. A compound consisting of an anion of a compound containing oxygen and at least one element selected from the group consisting of arsenic (As), sulfur (S), iron (Fe) and cobalt (Co), and a cation having a pigment skeleton. (AA) is preferable, and the compound (Aa) is composed of an anion of a compound containing at least one element selected from the group consisting of W, Mo, Si and P and oxygen, and a cation having a pigment skeleton. Is more preferable.

The rake pigment in the present invention is more preferably a rake pigment of a basic dye (triarylmethane dye, rhodamine dye, etc.) and a polyacid.
Polyacid, an acid in which a plurality of oxoacids are condensed, it may be a isopolyacid ion _{(M m1} O ^{n) c-,} heteropoly acid ion _{(X l} M _m1 O ⁿ⁾ be a ^c- good.
(In the formula, M is a poly atom, X is a hetero atom, l is a hetero atom composition ratio, m1 is a poly atom composition ratio, n is an oxygen atom composition ratio, and c is an integer of 1 to 8.)
Examples of the poly atom M include W, Mo, V, Ti and Nb. Examples of the heteroatom X include Si, P, As, S, Fe and Co.

Specific examples of preferable polyacids from the viewpoint of solvent resistance and heat resistance include _{isopolyacids such as tungstate ion [W 10} O ₃₂ ] ^4- and molybdenum acid ion [Mo ₆ O ₁₉ ] ^2- ; phosphotung acid. Ion [PW ₁₂ O ₄₀ ] ^3- , Heterometalate ion [SiW ₁₂ O ₄₀ ] ^4- , _{Phosmolybdenum acid ion [PMo 12} O ₄₀ ] ^3- , Lintangsto molybdenate ion [PW _12-x Mo _x O _40] ] ^3- , H ₃ [PW _2-x Mo _x O ₇ ] ^{4- and} other heteropolyacids, more specifically, preferably lintangst molybdenate ion [PW ₁₀ Mo ₂ O ₄₀ ] ^3- , [ Examples thereof include _{PW 11} Mo ₁ O ₄₀ ] ^3- and phosphotungstate ion [PW ₁₂ O ₄₀ ] ^3-.

Above all, from the viewpoint of solvent resistance, heat resistance and the like, the compound (Aa) is preferably a compound represented by the formula (AI).

[In formula (AI), [Y] ^m- represents an m-valent anion containing oxygen and at least one element selected from the group consisting of W, Mo, Si, and P. m represents an arbitrary natural number.
X ⁺ represents a cation represented by the formula (AIX). ]

[In the formula (AIX ^{), R 41 to R 44} are monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms and 2 to 20 carbon atoms, which may have substituents independently of each other. An alkyl group of the above, in which an oxygen atom is inserted between the methylene groups constituting the alkyl group (however, a plurality of oxygen atoms are not inserted adjacent to each other), and has a substituent. It represents a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms, an aralkyl group having 7 to 11 carbon atoms which may have a substituent, or a hydrogen atom. R ⁴¹ and R ⁴² may be bonded to form a ring with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may be bonded to form a ring with the nitrogen atom to which they are bonded.
R ^{47 to} R ⁵⁴ independently represent a hydrogen atom, a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a nitro group, a hydroxy group, or an alkyl group having 1 to 8 carbon atoms, and has 1 to 8 carbon atoms. When is 2 or more, oxygen atoms may be inserted between the methylene groups constituting the alkyl group (however, a plurality of oxygen atoms are not inserted adjacent to each other).
R ⁴⁸ and R ⁵² may be combined with each other to form -NH-, -O-, -S- or -SO _2- .
T ¹ represents a monovalent aromatic heterocyclic group which may have a substituent.
When m is a natural number of 2 or more, the plurality of X ⁺ may have the same structure or different structures. ]

The ^{monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 41 to} R ⁴⁴ includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group and a decyl group. A linear alkyl group having 1 to 20 carbon atoms such as a group, a dodecyl group, a hexadecyl group and an icosyl group; an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group and a 2-ethylhexyl group. Such as a branched chain alkyl group having 3 to 20 carbon atoms; an alicyclic saturated hydrocarbon having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecyl group. Examples thereof include a linear or branched alkyl group having 1 to 12 carbon atoms, more preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and further. Preferred are linear or branched alkyl groups having 1 to 6 carbon atoms.

The substituents that a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms can have include a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a cyano group, a nitro group, a hydroxy group, a substituent or no substituent. Substituted phenyl groups, substituted or unsubstituted amino groups and the like can be mentioned.

Alkyl groups having 2 to 20 carbon atoms in R ^{41 to} R ^44, in which an oxygen atom is inserted between the methylene groups constituting the alkyl group, include -CH _2- O-CH ₃ groups and-. CH _{2 -O-CH 2} -CH _{3 group,} such as _{-CH 2 -CH 2 -O-CH 2} -CH 3 group and the like.
Examples of the alkyl group having 2 to 20 carbon atoms include ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group and icosyl group. 2 to 20 linear alkyl groups; branched chain alkyl groups having 3 to 20 carbon atoms such as isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group and 2-ethylhexyl group. , Preferably a linear or branched alkyl group having 2 to 12 carbon atoms, more preferably a linear or branched alkyl group having 2 to 8 carbon atoms, and even more preferably. Examples thereof include linear or branched alkyl groups having 2 to 6 carbon atoms.

Examples of the monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms in R ^{41 to} R ⁴⁴ include a phenyl group, a toluyl group, a xsilyl group, a mesityl group, a propylphenyl group, a butylphenyl group, and a naphthyl group.
The substituents that the monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms can have include a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a cyano group, a nitro group, a hydroxy group and an alkoxy group. , Alkyl group having 1 to 8 carbon atoms, substituted or unsubstituted phenyl group, substituted or unsubstituted amino group and the like.

The aralkyl groups having 7 to 11 carbon atoms in R ^{41 to} R ⁴⁴ include a benzyl group, a phenylethyl group, a phenylpropyl group, a 2-methylphenylmethyl group, a 3-methylphenylmethyl group, a 4-methylphenylmethyl group, and 2 , 3-Dimethylphenylmethyl group, 2,4-dimethylphenylmethyl group, 2,5-dimethylphenylmethyl group, 2,6-dimethylphenylmethyl group, 3,4-dimethylphenylmethyl group, naphthylmethyl group and the like. Be done.

The substituents that the aralkyl group having 7 to 11 carbon atoms can have are halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), cyano group, nitro group, hydroxy group, alkoxy group, substituted or unsubstituted. Amino groups and the like can be mentioned.

Rings that can be formed by combining R ⁴¹ and R ⁴² with a nitrogen atom to which they are bonded, ^{and rings that can be formed by combining R 43} and R ⁴⁴ with a nitrogen atom to which they are bonded include a pyrrole ring and a pyrrolidine. Examples thereof include a ring, a piperidine ring, an imidazole ring, an indole ring, a purine ring, an ethyleneimine ring, a 1H-azirin ring, an azacyclobutane ring, a hexamethyleneimine ring, an azatropylidene ring, an imidazoline ring, a morpholin ring, a thiazine ring, and a carbazole ring. ..

Among them, R ^{41 to} R ⁴⁴ are preferably hydrogen atoms, alkyl groups having 1 to 6 carbon atoms, or phenyl groups independently of each other.

The alkyl groups having 1 to 8 carbon atoms in R ^{47 to} R ⁵⁴ include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group and octyl group; isopropyl group. , Isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, 2-ethylhexyl group and other branched chain alkyl groups, preferably alkyl groups having 1 to 6 carbon atoms, and more. Preferred examples thereof include a methyl group, an ethyl group, a propyl group and a butyl group.

The alkyl group in which an oxygen atom is inserted between the methylene groups constituting the alkyl group in R ^{47 to} R ⁵⁴ is an alkyl group having 2 to 8 carbon atoms, and oxygen is formed between the methylene groups constituting the alkyl group. are those atoms are _inserted, -CH 2 -O-CH _{3 group, -CH 2 -O-CH 2 -CH} 3 _{group, -CH 2 -CH 2 -O-CH} 2 -CH 3 group and the like Be done.

Among them, R ^{47 to} R ⁵⁴ are preferably hydrogen atoms or alkyl groups having 1 to 6 carbon atoms independently of each other.

Aromatic heterocyclic ring constituting the monovalent aromatic heterocyclic group in T ¹ is monocyclic may be either polycyclic, pyrrole, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, Examples thereof include thiazole, isothiazole, pyridine, pyrimidine, pyridazine, pyrazine, 1,2,3-triazine, quinoline, isoquinoline, quinazoline, indol, benzimidazole, benzofuran, purine, aclysine, phenoxazine and phenothiazine.

The substituents that the aromatic heterocyclic group can have include a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a cyano group, a nitro group, a hydroxy group, an alkoxy group having 1 to 8 carbon atoms, and a carbon number of carbon atoms. Examples include 1 to 8 alkyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted amino groups and the like.

[Y] ^m- represents an m-valent anion containing oxygen and at least one element selected from the group consisting of W, Mo, Si, and P. m represents an arbitrary natural number. From the viewpoint of solvent resistance, heat resistance and the like, the anion is preferably the above-mentioned polyacid, and preferred specific examples thereof are as described above. m is preferably a natural number of 1 to 10, and more preferably a natural number of 1 to 6.

[1-2] Dye The colorant (A) can further contain a dye in addition to the lake pigment. The dye is not particularly limited, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified in the Color Index (published by The Society of Dyers and Colorists) as having hues other than pigments, and known dyes described in dyeing notes (Dyeing Co., Ltd.). Be done. According to the chemical structure, azo dye, cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acrydin dye, styryl dye, coumarin. Examples include dyes, quinoline dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

Specifically, C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;
C. I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like. I. Solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176,182,183,195,198,206,211,215,216,217,227,228,249,252,257,258,260,261,266,268,270, 274,277,280,281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;
C. I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C. I. Acid Blue 1,3,5,7,9,11,13,15,17,18,22,23,24,25,26,27,29,34,38,40,41,42,43,45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93, 93: 1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;
C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50: 1, 58, 63, 65, 80, C.I., 104, 105, 106, 109, etc. I. Acid dye,
C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and the like. I. Direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. Disperse Blue 1, 14, 56, 60, etc. I. Disperse dye,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C. I. Basic Violet 2;
C. I. Basic Red 9;
C. I. Basic Green 1 etc. C.I. I. Basic dye,
C. I. Reactive Yellow 2,76,116;
C. I. Reactive Orange 16;
C. I. C. of Reactive Red 36 etc. I. Reactive dye,
C. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C. I. Modant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Modern Violet 1, 1: 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Modant Blue 1,2,3,7,8,9,12,13,15,16,19,20,21,22,23,24,26,30,31,32,39,40,41,43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. I. Mordant dye, C.I. I. Bat Green 1 etc. C.I. I. Vat dyes and the like can be mentioned.

These dyes may be appropriately selected according to the spectral spectrum of the desired color filter.

Above all, when a dye is used, the dye preferably contains a xanthene dye from the viewpoint of solvent resistance, heat resistance and the like, and from the viewpoint of obtaining good brightness. A xanthene dye is a dye containing a compound having a xanthene skeleton in the molecule. Examples of the xanthene dye include C.I. I. Acid Red 51, 52, 87, 92, 94, 289, 388, C.I. I. Acid Violet 9, 30, 102, C.I. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, C.I. I. Basic Red 10, 11, C.I. I. Basic Violet 10 (Rhodamine B), 11, C.I. I. Solvent Red 218, C.I. I. Modant Red 27, C.I. I. Examples thereof include reactive red 36 (rose bengal B), sulforhodamine G, xanthene dyes described in JP-A-2010-32999, and xanthene dyes described in Japanese Patent No. 4492760. Of these, those that dissolve in an organic solvent are preferable.

Among these, as the xanthene dye, a dye containing a compound represented by the formula (1a) (hereinafter, may be referred to as “compound (1a)”) is preferable. Compound (1a) may be a tautomer thereof. When the xanthene dye is further contained as the colorant (A), the content of the compound (1a) in the xanthene dye is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 90% by mass or more. .. In particular, it is preferable to use only the compound (1a) as the xanthene dye.

[In the formula (1a), R ^{1 to} R ⁴ have a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms and a substituent, which may have a hydrogen atom and a substituent, independently of each other. It represents a monovalent aromatic hydrocarbon group having 7 to 20 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and the saturated hydrocarbon group and the aralkyl group. _-CH 2 contained in - is, -O -, - CO- or ^{-NR 11} - may be replaced by. R ¹ and R ² may be combined to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom.
R ^{5 _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO ₂ N (R ⁹ ) Represents ^{R 10.}
R ⁶ and R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
m represents an integer from 0 to 5. when m is 2 or more, plural R ⁵ may be the same or different.
a represents an integer of 0 or 1.
X represents a halogen atom.
Z ^{+ _{is, + N (R 11) 4}} , represents Na ⁺ or ^{K +,} 4 one ^{R 11} may be the same or different.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
R ⁹ and R ¹⁰ represent monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon group-. CH ₂ - is, -O -, - CO -, - NH- or -N ^{(R 8)} - may be had I placed conversion in, ^{R 9} and ^{R 10,} including the nitrogen atom bonded with each other 3 It may form a heterocycle of 10-membered rings.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. In formula (1a), -SO ₃ ^- if there is, the number is one. ]

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ^{1 to} R ⁴ include a phenyl group, a toluyl group, a xsilyl group, a mesityl group, a propylphenyl group and a butylphenyl group.

The aromatic hydrocarbon group substituent which may have a halogen _{^{atom, -R 8, -OH, -OR 8}} , -SO 3 -, -SO 3 H, -SO 3 - Z +, - Examples thereof include CO ₂ H, -CO ₂ R ⁸ , -SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ⁸ or -SO ₂ N (R ⁹ ) R ^10. Among them, as the _{^{substituent, -SO 3 -, -SO 3 H}} , -SO 3 - Z + and _{^{-SO 2 N (R 9) R}} 10 is preferably, _-SO ³ - ^{Z +} and _-SO 2 N (R ⁹ ) R ¹⁰ is more preferable. In this case, as −SO ₃ ⁻ Z ⁺ , −SO ₃ ^{− +} N (R ¹¹ ) ₄ is preferable. When R ^{1 to} R ⁴ are these groups, the color curable resin composition of the present invention containing the compound (1a) forms a color filter that generates less foreign matter and is superior in solvent resistance and heat resistance. can.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ^{1 to} R ⁴ and R ^{8 to} R ¹¹ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and a heptyl group. , Octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group, icosyl group and other linear alkyl groups; isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group and other branched chain alkyl groups; Examples thereof include an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecyl group.

The ^{hydrogen atom contained in the saturated hydrocarbon group in R 1 to} R ⁴ may be substituted with, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom.

The ^{hydrogen atom contained in the saturated hydrocarbon group in R 9} and R ¹⁰ may be substituted with, for example, a hydroxy group or a halogen atom.

Examples of the ring formed by R ¹ and R ² together and the ring formed by R ³ and R ^{4 together include the following.}

Examples of −OR ⁸ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group and an icosyloxy group.

Examples of -CO ₂ R ⁸ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, an icosyloxycarbonyl group and the like.

Examples of -SR ¹ include methylsulfanil group, ethylsulfanil group, butylsulfanil group, hexylsulfanil group, decylsulfanil group, icosylsulfanil group and the like.

Examples of -SO ₂ R ⁸ include a methyl sulfonyl group, an ethyl sulfonyl group, a butyl sulfonyl group, a hexyl sulfonyl group, a decyl sulfonyl group and an icosyl sulfonyl group.

Examples of the -SO ₃ R ⁸ include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group and an icosyloxysulfonyl group.

-SO ₂ N (R ⁹ ) R ¹⁰ includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butyl sulfamoyl group, N-tert-butyl sulfamoyl group, N-pentyl sulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3) -Methylbutyl) sulfamoyl group, N-cyclopentyl sulfamoyl group, N-hexyl sulfamoyl group, N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N- Heptyl sulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N-octyl sulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- N-1-substituted sulfamoyl groups such as (1,5-dimethyl) hexyl sulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group;
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfa Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl Examples thereof include N, N-2 substituted sulfamoyl groups such as groups.

R ^{5 _{is, -CO 2 H, -CO 2 -}} Z +, -CO 2 R 8, -SO 3 -, -SO 3 - Z +, -SO 3 H or _SO 2 NHR ⁹ are preferred, SO ₃ ^-, -SO ₃ ^- Z ⁺ , -SO ₃ H or SO ₂ NHR ⁹ are more preferred.
m is preferably 1 to 4, more preferably 1 or 2.

Examples of the alkyl group having 1 to 6 carbon atoms in R ⁶ and R ⁷ include those having 1 to 6 carbon atoms among the alkyl groups listed above.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ include a benzyl group, a phenylethyl group, a phenylbutyl group and the like.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹¹ ) ₄ .
The ⁺ a N ^(R _{11) 4,} of the four ^{R 11,} it is preferred that at least two of a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. The total number of carbon atoms of the four ^{R 11} is preferably 20 to 80, 20 to 60 is more preferable. ^{When +} N (R ¹¹ ) ₄ is present in the compound (1a), ^{if R 11} is these groups, the color filter containing the compound (1a) and having less foreign matter can be obtained from the color curable resin composition of the present invention. Can be formed.

As the compound (1a), a compound represented by the formula (2a) (hereinafter, may be referred to as “compound (2a)”) is preferable. Compound (2a) may be a tautomer thereof.

[In formula (2a), R ^{21 to} R ²⁴ represent monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a ^{hydrogen atom, -R 26} or a substituent independently of each other. ..
R ²¹ and R ²² may be combined to form a ring containing a nitrogen atom, and R ²³ and R ²⁴ may be combined to form a ring containing a nitrogen atom.
R ²⁵ _is, ^-SO 3 _- represents a Z1 ⁺ or ^{_{-SO 2 NHR 26 -, -SO 3}} H, -SO 3.
m1 represents an integer from 0 to 5. When m1 is 2 or more, the plurality of R ^25s may be the same or different.
a1 represents an integer of 0 or 1.
X1 represents a halogen atom.
R ²⁶ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
Z1 ⁺ represents ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , and the four R ^27s may be the same or different.
R ²⁷ represents a monovalent saturated hydrocarbon group or benzyl group having 1 to 20 carbon atoms. ]

In the formula (2a), as the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in ^{R 21 to} R ^24, the same group as the group mentioned as the aromatic hydrocarbon group of ^{R 1 to} R ^{4 is used.} Can be mentioned. The hydrogen atom contained in the aromatic hydrocarbon group may be substituted with _{−SO 3} ⁻ , _{− SO 3} H, − SO ₃ ⁻ Z1 ⁺ , − SO ₃ R ²⁶ or − SO ₂ NHR ^26.

In the formula (2a), as a combination of ^{R 21 to} R ^{24 , R 21} and R ²³ are hydrogen atoms, and R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms. , hydrogen atoms contained in the aromatic hydrocarbon _{^{group, -SO 3 -, -SO 3 H}} , -SO 3 - Z1 +, a group is substituted with -SO ^{3 R 26} or _-SO 2 ^{NHR 26} preferably , R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon groups are −. Groups substituted with SO ₃ ^- Z1 ⁺ or -SO ₂ NHR ²⁶ are even more preferred.
When R ^{21 to} R ²⁴ are these groups, a color filter having better solvent resistance and heat resistance can be formed from the color curable resin composition of the present invention containing the compound (2a).

As ^{a ring containing a nitrogen atom formed by R 21} and R ²² together and a ring containing a nitrogen atom formed by R ²³ and R ²⁴ together, R ¹ and R ² are combined. A ring similar to the ring to be formed can be mentioned, preferably an aliphatic heterocycle. Examples of the aliphatic heterocycle include the following rings.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ²⁶ and R ²⁷ include the same group as the group mentioned as ^{the saturated hydrocarbon group in R 8 to} R ^11.

When R ^{21 to} R ²⁴ are -R ^26, it is preferable that -R ²⁶ is a methyl group or an ethyl group independently of each other. _As the ^{R 26} in -SO ^{3 R 26} and _-SO 2 ^{NHR 26,} preferably branched alkyl group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 6 to 12 carbon atoms, 2-Ethylhexyl groups are more preferred.
When R ²⁶ is these groups, a color filter having excellent solvent resistance and heat resistance can be formed from the colored curable resin composition of the present invention containing the compound (2a).

Z1 ⁺ is ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ²⁷ ) ₄ .
The ⁺ a N ^(R _{27) 4,} among the four ^{R 27,} it is preferred that at least two of a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. The total number of carbon atoms of the four ^{R 27} is preferably 20 to 80, 20 to 60 is more preferable.
^{When +} N (R ²⁷ ) ₄ is present in the compound (2a), ^{if R 27} is these groups, the color curable resin composition of the present invention containing the compound (2a) shows solvent resistance and heat resistance. A color filter having excellent properties can be formed.

m1 is preferably 1 to 4, more preferably 1 or 2.

Further, as the compound (1a), a compound represented by the formula (3a) (hereinafter, may be referred to as “compound (3a)”) is also preferable. Compound (3a) may be a tautomer thereof.

[In the formula (3a), R ³¹ and R ³² independently represent a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and the saturated hydrocarbon group and the same. The hydrogen atom contained in the aralkyl group may be substituted with a halogen atom, respectively, and the hydrogen atom contained in the aromatic hydrocarbon group of the aralkyl group is substituted with an alkoxy group having 1 to 3 carbon atoms. may, _-CH 2 contained in the saturated hydrocarbon group and the aralkyl group - is, -O -, - CO- or ^{-NR 11} - may be replaced by.
R ³³ and R ³⁴ independently represent an alkyl group having 1 to 4 carbon atoms, an alkyl sulfanyl group having 1 to 4 carbon atoms, or an alkylsulfonyl group having 1 to 4 carbon atoms.
R ³¹ and R ³³ may be combined to form a ring containing a nitrogen atom, and R ³² and R ³⁴ may be combined to form a ring containing a nitrogen atom.
p and q represent integers 0 to 5 independently of each other. When p is 2 or more, the plurality of R ^33s may be the same or different, and when q is 2 or more, the plurality of R ^34s may be the same or different.
R ¹¹ has the same meaning as described above. ]

The ^{monovalent saturated hydrocarbon group having 1 to 10 carbon atoms in R 31} and R ³² is a linear chain such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group. Alkyl group; branched chain alkyl group such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like having 3 to 3 carbon atoms. Examples thereof include 10 alicyclic saturated hydrocarbon groups.
Examples of the aralkyl group in R ³¹ and R ³² include a phenylene group and the like.

The aromatic hydrocarbon group having 6 to 10 carbon atoms that may have a substituent group, include the same groups as in R ^1.

Examples of the alkoxy group having 1 to 3 carbon atoms include a methoxy group, an ethoxy group, a propoxy group and the like.

R ³¹ and R ³² are preferably hydrogen atoms or monovalent saturated hydrocarbon groups having 1 to 3 carbon atoms independently of each other.

Examples of the alkyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group and the like.

Examples of the alkylsulfanyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl sulfanyl group, an ethyl sulfanyl group, a propyl sulfanyl group, a butyl sulfanyl group, an isopropyl sulfanyl group and the like.

Examples of the alkylsulfonyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl sulfonyl group, an ethyl sulfonyl group, a propyl sulfonyl group, a butyl sulfonyl group and an isopropyl sulfonyl group.

R ³³ and R ³⁴ are preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
p and q are preferably integers of 0 to 2, preferably 0 or 1.

Examples of the compound (1a) include compounds represented by the formulas (1-1) to (1-43). In the formula, R ⁴⁰ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched chain alkyl group having 6 to 12 carbon atoms, and more preferably a 2-ethylhexyl group.

Among the above compounds, the compounds represented by the formulas (1-1) to (1-23) or the formulas (1-37) to (1-43) correspond to the compound (2a) and are represented by the formula (1-37). 24) The compound represented by any of the formulas (1-36) corresponds to the compound (3a).

Among these, C.I. I. Sulfonamides of Acid Red 289, C.I. I. Acid Red 289 Quaternary Ammonium Salt, C.I. I. Sulfonamides of acid violet 102 or C.I. I. A quaternary ammonium salt of Acid Violet 102 is preferred. Examples of such a compound include compounds represented by formulas (1-1) to (1-8), formulas (1-11) or formulas (1-12).

Further, a compound represented by any of the formulas (1-24) to (1-33) is also preferable because of its excellent solubility in an organic solvent.

As the xanthene dye, a commercially available xanthene dye (for example, "Chugai Aminol Fast Pink R-H / C" manufactured by Chugai Pharmaceutical Co., Ltd., "Rhodamin 6G" manufactured by Taoka Chemical Industry Co., Ltd.) can be used. Further, it is also possible to synthesize using a commercially available xanthene dye as a starting material with reference to Japanese Patent Application Laid-Open No. 2010-32999.

[1-3] Coloring Pigment The colorant (A) can further contain a coloring pigment (however, different from the lake pigment) in addition to the lake pigment. As the coloring pigment, a known coloring pigment can be used without particular limitation, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists).

Examples of the coloring pigment include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58 and other green pigments;
C. I. Pigment brown 23, 25 and other brown pigments;
C. I. Examples thereof include black pigments such as Pigment Blacks 1 and 7.

Examples of the coloring pigment include C.I. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments are preferred. I. Pigment Blue 15: 3, 15: 6 and C.I. I. Pigment Violet 23 is more preferred, C.I. I. Pigment Blue 15: 6 is even more preferred. By including the above-mentioned coloring pigment, it is easy to optimize the transmission spectrum, and the light resistance and solvent resistance of the color filter are improved.

Color pigments are fine particles, if necessary, such as rosin treatment, surface treatment using a pigment derivative having an acidic group or a basic group introduced, graft treatment on the pigment surface with a polymer compound, or the like using a sulfuric acid atomization method. It may be subjected to a chemical treatment, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment of ionic impurities by an ion exchange method, or the like.

The color pigment preferably has a uniform particle size. By carrying out the dispersion treatment by adding a pigment dispersant, it is possible to obtain a pigment dispersion liquid in which the colored pigments are uniformly dispersed in the solution.

Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Pigment dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by CIBA), and Ajinomoto Fine. Examples include Techno Co., Ltd. and Disperbyk (manufactured by Big Chemie).

When a pigment dispersant is used, the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less with respect to the total amount of the coloring pigment. When the amount of the pigment dispersant used is in the above range, a pigment dispersion liquid in a uniformly dispersed state tends to be obtained.

[1-4] Content of Colorant (A) The content of the colorant (A) is preferably 5 to 60% by mass, more preferably 5 to 60% by mass, based on the total solid content of the color-curable resin composition. Is 8 to 55% by mass, more preferably 10 to 50% by mass. When the content of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and the composition contains a required amount of the resin (B) and the polymerizable compound (C). Therefore, it is possible to form a pattern having sufficient mechanical strength. Here, the "total amount of solid content" in the present specification means an amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography or gas chromatography.

From the viewpoint of solvent resistance and heat resistance, the content of the rake pigment in the colorant (A) is preferably 2.5 to 100% by mass, more preferably 10 to 100% by mass, based on 100% by mass of the colorant (A). It is 100% by mass, more preferably 30 to 100% by mass, particularly preferably 45 to 100% by mass, particularly preferably 75 to 100% by mass, and particularly preferably 90 to 100% by mass. ..

When the colorant (A) contains a dye, the content of the dye in the colorant (A) is usually 0.1% by mass or more in 100% by mass of the colorant (A) from the viewpoint of solvent resistance and heat resistance. It is preferably 0.5% by mass or more, usually 100% by mass or less, preferably 98% by mass or less, more preferably 60% by mass or less, and further preferably 50% by mass or less. , Especially preferably 25% by mass or less, and particularly preferably 10% by mass or less.

When the colorant (A) contains a color pigment, the content of the color pigment in the colorant (A) is usually 0.1% by mass in 100% by mass of the colorant (A) from the viewpoint of solvent resistance and heat resistance. % Or more, preferably 0.5% by mass or more, usually 98% by mass or less, preferably 60% by mass or less, more preferably 50% by mass, still more preferably 25% by mass or less. Yes, particularly preferably 10% by mass or less.

When the colorant (A) contains a dye and / or a color pigment, the total content of the dye and the color pigment is 1 to 80 parts by mass with respect to 100 parts by mass of the rake pigment from the viewpoint of solvent resistance and heat resistance. It is preferably 1 to 60 parts by mass, more preferably 1 to 40 parts by mass, and particularly preferably 1 to 20 parts by mass.

[2] Resin (B)
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

Resin [K1]; at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)") and cyclic ethers having 2 to 4 carbon atoms. Copolymer with monomer (b) having a structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");
Resin [K2]; (a) and (b) and monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter "(c)" Copolymer with);
Resin [K3]; copolymer of (a) and (c);
Resin [K4]; Resin obtained by reacting (b) with a copolymer of (a) and (c);
Resin [K5]; Resin obtained by reacting (a) with a copolymer of (b) and (c);
Resin [K6]; A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting with a carboxylic acid anhydride.

Specifically, as (a), unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid, 1,4-cyclohexendicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] Bicyclounsaturated compounds containing a carboxy group such as hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of divalent or higher valent carboxylic acids such as monosuccinate [2- (meth) acryloyloxyethyl] and mono [2- (meth) acryloyloxyethyl] phthalates. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylate.

Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an alkaline aqueous solution.

(B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. say. In (b), a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group is preferable.

In the present specification, "(meth) acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

Examples of (b) include a monomer (b1) having an oxylanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a simple monomer having an oxetanyl group and an ethylenically unsaturated bond. A metric (b2) (hereinafter sometimes referred to as "(b2)"), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)"), etc. Can be mentioned.

As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”). ), Monomers (b1-2) having an alicyclic unsaturated hydrocarbon epoxidized structure (hereinafter, may be referred to as “(b1-2)”).

Examples of (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p. -Vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene , 2,4-Bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene , 2,3,5-tris (glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2,4,6-tris (Glysidyloxymethyl) styrene and the like can be mentioned.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, celloxide 2000; manufactured by Daicel Co., Ltd.), and 3,4-epoxycyclohexylmethyl (meth) acrylate (for example,). Cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Co., Ltd.), a compound represented by the formula (I) and a compound represented by the formula (II). Examples thereof include compounds represented by.

[In formulas (I) and (II), ^Ra and R ^b represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group. You may.
X ^a and ^{X b} is a single ^{bond, -R c -, * - R} c -O -, * - represents the R c -S- or ^* -R c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group and the like.

The alkyl groups in which the hydrogen atom is substituted with hydroxy include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and a 1-hydroxy group. Examples thereof include -1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group and 4-hydroxybutyl group.

Examples of R ^a and R ^b include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

The alkanediyl group includes a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-. Examples include 1,6-diyl group.

Examples of X ^a and X ^b are preferably a single bond, a methylene group, an ethylene group, * -CH _2- O- and * -CH ₂ CH _2- O-, and more preferably a single bond, * -CH ₂ CH _2- O-can be mentioned (* represents a bond with O).

Examples of the compound represented by the formula (I) include compounds represented by any of the formulas (I-1) to (I-15). Among them, formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) or formula (I-11) to formula (I-15). The compound represented by the formula (I-1), the formula (I-7), the formula (I-9) or the compound represented by the formula (I-15) is more preferable.

Examples of the compound represented by the formula (II) include compounds represented by any of the formulas (II-1) to (II-15). Among them, formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) or formula (II-11) to formula (II-15). The compound represented by the formula (II-1), the formula (II-7), the formula (II-9) or the compound represented by the formula (II-15) is more preferable.

The compound represented by the formula (I) and the compound represented by the formula (II) may be used alone or in combination of two or more. When the compound represented by the formula (I) and the compound represented by the formula (II) are used in combination, the content ratio thereof [the compound represented by the formula (I): the compound represented by the formula (II)] is On a molar basis, it is preferably 5:95 to 95: 5, more preferably 20:80 to 80:20.

As (b2), a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable. Examples of (b2) include 3-methyl-3-methacrylloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, and 3-ethyl-3-acryloyloxymethyloxetane. , 3-Methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane and the like.

As (b3), a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

As (b), (b1) is preferable in that the reliability of the obtained color filter such as heat resistance and chemical resistance can be further improved. Further, (b1-2) is more preferable in that the color-curable resin composition is excellent in storage stability.

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0] ^2,6 ] Decane-8-yl (meth) acrylate (in the art, it is commonly referred to as "dicyclopentanyl (meth) acrylate" and also as "tricyclodecyl (meth) acrylate". (In some cases.), Tricyclo [5.2.1.0 ^2,6 ] decene-8-yl (meth) acrylate (in the art, it is commonly referred to as "dicyclopentenyl (meth) acrylate". ), Dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate , (Meta) acrylic acid esters such as benzyl (meth) acrylate;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2] .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] Hept-2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy -5-Methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2] .2.1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-Phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene, 5,6-bis (cyclohexyl) Bicyclounsaturated compounds such as oxycarbonyl) bicyclo [2.2.1] hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylnitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , Isoprene, 2,3-dimethyl-1,3-butadiene and the like.

Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are selected from the viewpoint of copolymerization reactivity and heat resistance. preferable.

In the resin [K1], the ratio of the structural units derived from each is determined in the total structural units constituting the resin [K1].
Structural unit derived from (a); 2-60 mol%
Structural unit derived from (b); 40-98 mol%
Is preferable
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (b); 50-90 mol%
Is more preferable.

When the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the color-curable resin composition, the developability when forming a color pattern, and the solvent resistance of the obtained color filter are excellent. Tend.

Resin [K1] can be used, for example, in the method described in the document "Design of Experiments for Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st edition, published on March 1, 1972). It can be manufactured with reference to the cited references described in.

Specifically, the predetermined amounts of (a) and (b), the polymerization initiator, the solvent and the like are placed in the reaction vessel, and for example, oxygen is replaced with nitrogen to create a deoxidized atmosphere, and the mixture is stirred. Examples thereof include a method of heating and keeping warm. The polymerization initiator, solvent, and the like used here are not particularly limited, and those usually used in the art can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) As the solvent, any solvent may be used as long as it dissolves each monomer, and examples of the solvent (E) of the colored curable resin composition of the present invention include a solvent described later.

As the obtained copolymer, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, or the copolymer is taken out as a solid (powder) by a method such as reprecipitation. You may use the one. In particular, by using the solvent contained in the color curable resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the color curable resin composition of the present invention. Therefore, the manufacturing process of the colored curable resin composition of the present invention can be simplified.

In the resin [K2], the ratio of the structural units derived from each is determined in the total structural units constituting the resin [K2].
Structural unit derived from (a); 2-45 mol%
Structural unit derived from (b); 2-95 mol%
Structural unit derived from (c); 1-65 mol%
Is preferable
Structural unit derived from (a); 5-40 mol%
Structural unit derived from (b); 5-80 mol%
Structural unit derived from (c); 5-60 mol%
Is more preferable.

When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the color-curable resin composition, the developability when forming a color pattern, and the solvent resistance of the obtained color filter, It tends to have excellent heat resistance and mechanical strength.

The resin [K2] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].

In the resin [K3], the ratio of the structural units derived from each is determined in the total structural units constituting the resin [K3].
Structural unit derived from (a); 2-60 mol%
Structural unit derived from (c); 40-98 mol%
Is preferable
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (c); 50-90 mol%
Is more preferable.

The resin [K3] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].

The resin [K4] is a carboxylic acid and / or a carboxylic acid anhydride having the cyclic ether having 2 to 4 carbon atoms of (b) obtained by obtaining a copolymer of (a) and (c). It can be manufactured by adding to.

First, the copolymer of (a) and (c) is produced in the same manner as the method described as the method for producing the resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that mentioned in the resin [K3].

Next, the cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer.

Following the production of the copolymer of (a) and (c), the atmosphere in the flask was replaced with air from nitrogen, and (b), a reaction catalyst of carboxylic acid or carboxylic acid anhydride and cyclic ether (for example, Tris (for example, Tris) Resin [K4] can be produced by putting (dimethylaminomethyl) phenol, etc.) and a polymerization inhibitor (for example, hydroquinone, etc.) in a flask and reacting at 60 to 130 ° C. for 1 to 10 hours, for example. can.

The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, based on 100 mol of (a). Within this range, the storage stability of the color-curable resin composition, the developability when forming a pattern, and the balance between the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern are improved. Tend. Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K4], and (b1-1) is further preferable.

The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c).

The reaction conditions such as the charging method, the reaction temperature and the time can be appropriately adjusted in consideration of the production equipment, the calorific value due to the polymerization and the like. As with the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the calorific value due to the polymerization, and the like.

As the first step, the resin [K5] obtains a copolymer of (b) and (c) in the same manner as in the above-mentioned production method of the resin [K1]. In the same manner as above, the obtained copolymer may be a solution after the reaction as it is, a concentrated or diluted solution may be used, or a solid (powder) may be used by a method such as reprecipitation. You may use the one taken out as.

The ratio of the structural units derived from (b) and (c) is, respectively, with respect to the total number of moles of all the structural units constituting the copolymer.
Structural unit derived from (b); 5 to 95 mol%
Structural unit derived from (c); 5 to 95 mol%
Is preferable
Structural unit derived from (b); 10-90 mol%
Structural unit derived from (c); 10-90 mol%
Is more preferable.

Further, under the same conditions as the method for producing the resin [K4], the carboxylic acid or carboxylic acid anhydride of (a) is added to the cyclic ether derived from (b) of the copolymer of (b) and (c). The resin [K5] can be obtained by reacting an object.

The amount of (a) used to react with the copolymer is preferably 5 to 80 mol with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K5], and (b1-1) is further preferable.

The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride.
The carboxylic acid anhydride is reacted with the hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic acid anhydride.

Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic acid anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride and the like. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mol with respect to 1 mol of the amount used in (a).

The resin (B), specifically, 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymers, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] Resins such as decyl acrylate / (meth) acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) ) Acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decylacrylate / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, 3-methyl-3-( Resin [K2] such as meta) acrylic loyloxymethyloxetane / (meth) acrylic acid / styrene copolymer; benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer Resins such as [K3]; benzyl (meth) acrylate / (meth) acrylic acid copolymer to which glycidyl (meth) acrylate is added, tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid co-weight. Resins with glycidyl (meth) acrylate added to the coalescence, resins such as tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylate copolymer with glycidyl (meth) acrylate added [ K4]; Co-weight of tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate, a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid. Resin such as resin in which (meth) acrylic acid is reacted with coalescence [K5]; Tetrahydro is further added to resin in which (meth) acrylic acid is reacted with a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate. Examples thereof include a resin [K6] such as a resin obtained by reacting an phthalic acid anhydride. Among them, as the resin (B), the resin [K1] and the resin [K2] are preferable.

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the weight average molecular weight (Mw) is within the above range, the hardness of the color filter is improved, the residual film ratio is high, the solubility of the unexposed area in the developing solution is good, and the resolution of the coloring pattern tends to be improved. There is.

The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150, and even more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined by titration using, for example, an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, still more preferably 17 to 55% by mass, based on the total solid content of the color curable resin composition. be. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tend to be improved.

[3] Polymerizable compound (C)
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, which is preferable. Is a (meth) acrylic acid ester compound.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa (). Meta) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl ) Isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, Examples thereof include caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate.

Of these, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 to 1,500 or less.

The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, still more preferably 17 to 55% by mass, based on the total solid content of the colored curable resin composition. %. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the coloring pattern and the solvent resistance of the color filter tend to be improved.

[4] Polymerization initiator (D)
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids and the like by the action of light or heat and initiating polymerization, and a known polymerization initiator can be used.
Examples of the polymerization initiator that generates an active radical include an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound.

The O-acyloxime compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * represents a bond.

Examples of the O-acyloxym compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane. -1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- [9-ethyl-6-] (2-Methylbenzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,, 3-dimethyl-2,) 4-Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole] -3-yl] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3-cyclopentylpropane- 1-on-2-imine and the like can be mentioned. Commercially available products such as Irgacure OXE01 and OXE02 (all manufactured by BASF Corporation) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, the O-acyloxym compounds are N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1. At least one selected from the group consisting of −on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy is preferable. -1- (4-Phenylsulfanylphenyl) octane-1-one-2-imine is more preferred. With these O-acyloxime compounds, a high-brightness color filter tends to be obtained.

The alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3). In these partial structures, the benzene ring may have a substituent. * Represents a bond.

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4). -Morholinophenyl) -2-benzyl butane-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one And so on. Commercially available products such as Irgacure 369, 907, 379 (all manufactured by BASF Limited) may be used.

Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1- [4- (2). -Hydroxyethoxy) phenyl] Propane-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one oligomer, α, α-diethoxy Examples thereof include acetophenone and benzyl dimethyl ketal.

In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by the formula (d2).

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-). Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy) Styryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4 -Bis (trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-) 2-Methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine, etc. Can be mentioned.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) may be used.

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl)-. 4,4', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4 , 4', 5,5'-tetraphenyl biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2-Chlorophenyl) -4,4', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (tri) Alkoxyphenyl) Biimidazole (see, for example, Japanese Patent Application Laid-Open No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.), the phenyl group at the 4,4'5,5'-position is substituted with a carboalkoxy group. Examples thereof include imidazole compounds (see, for example, Japanese Patent Application Laid-Open No. 7-10913).

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, methyl o-benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrene quinone, Kinone compounds such as 2-ethylanthraquinone and campharquinone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methyl phenylglycoxylate, titanosen compounds and the like. These are preferably used in combination with the polymerization initiation aid (D1) (particularly an amine compound) described later.

Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethyl. Onium salts such as benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyltosilates, Examples thereof include benzointosilates.

As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound is preferable, and an O-acyloxy compound is preferable. A polymerization initiator containing a compound compound is more preferable.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Is. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

[5] Polymerization initiation aid (D1)
The colored curable resin composition of the present invention can contain a polymerization initiation aid (D1). The polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by the polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and 4 -Dimethylaminobenzoate 2-ethylhexyl, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis Examples thereof include (ethylmethylamino) benzophenone, and among them, 4,4'-bis (diethylamino) benzophenone is preferable. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-di. Butoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like can be mentioned.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.

Examples of the carboxylic acid compound include phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, and dichlorophenylsulfanyl acetic acid. Examples thereof include N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.

When these polymerization initiators (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is preferably 1 to 20 parts by mass. When the amount of the polymerization initiation aid (D1) is within this range, a coloring pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

[6] Constituent pigment (P)
The colored curable resin composition of the present invention contains an extender pigment (P). According to the color curable resin composition of the present invention containing the colorant (A) containing the rake pigment and the extender pigment (P), the solvent resistance and heat resistance of the cured film (color filter, etc.) are improved. Can be made to.

The extender pigment (P) is not particularly limited, and known extender pigments can be used. Zinc oxide (ZnO), titanium oxide (TiO ₂ ), silica (SiO ₂ ), zirconia (ZrO ₂ ), barium carbonate. Examples thereof include extender pigments such as (BaCO ₃ ), lime carbonate (CaCO ₃ ), basic magnesium carbonate (MgCO ₃ ), aluminum hydroxide (Al (OH) ₃ ), kaolin clay, and neferin cynicite.

Among them, the extender pigment (P) is at least one selected from the group consisting of zinc oxide, titanium oxide, silica, zirconia, barium carbonate, lime carbonate and basic magnesium carbonate from the viewpoint of solvent resistance and heat resistance. It is preferable that it is at least one selected from the group consisting of zinc oxide, titanium oxide, silica and zirconia. Further, among these, those having higher transparency are preferable.
The extender pigment (P) preferably has a primary particle size of 0.1 μm or less, and more preferably 0.05 μm or less in terms of high transparency. The primary particle size of the extender pigment (P) is usually 0.01 μm or more.

The content of the extender pigment (P) is preferably 0.5 to 10% by mass, more preferably 1 to 7% by mass, still more preferably 1.5, based on the total solid content of the color-curable resin composition. ~ 5% by mass. When the content of the extender pigment (P) is within the above range, it is advantageous in improving the solvent resistance and the heat resistance.

[7] Solvent (E)
The colored curable resin composition of the present invention can contain a solvent (E). The solvent (E) is not particularly limited, and a solvent usually used in the art can be used.
Examples of the solvent (E) include an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), an ether solvent (a solvent containing -O- in the molecule and not containing -COO-), and the like. Ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule) , -O-, -CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenyletol and methyl anisol.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene and mesitylene.

Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.

Among the above solvents, an organic solvent having a boiling point of 120 ° C. or higher and 180 ° C. or lower at 1 atm is preferable from the viewpoint of coatability and drying property. The solvent is preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2. -Pentanone and N, N-dimethylformamide are mentioned, and more preferably, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are mentioned.

The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition of the present invention. In other words, the total solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating is good, and the display characteristics tend to be good because the color density is not insufficient when the color filter is formed. ..

[8] Leveling agent (F)
The colored curable resin composition of the present invention can further contain a leveling agent (F). Examples of the leveling agent (F) include a silicone-based surfactant (which does not have a fluorine atom), a fluorine-based surfactant (different from a silicone-based surfactant), and a silicone-based surfactant having a fluorine atom. .. These may have a polymerizable group in the side chain.

Examples of the silicone-based surfactant (which does not have a fluorine atom) include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK), etc. Can be mentioned.

Examples of the fluorine-based surfactant (different from the silicone-based surfactant) include a surfactant having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include MegaFvck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, and more preferably 0.002% by mass or more and 0.1% by mass with respect to the total amount of the colored curable resin composition. % Or less, more preferably 0.01% by mass or more and 0.05% by mass or less. The pigment dispersant is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[9] Other Ingredients The color curable resin composition of the present invention may be further subjected to other technical fields such as other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like, if necessary. May contain additives known in.

<Manufacturing method of colored curable resin composition>
The color curable resin composition of the present invention comprises a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and an extender pigment (P), and a solvent used as necessary. It can be prepared by mixing (E), a leveling agent (F), a polymerization initiator (D1) and other components.

When the colorant (A) contains a color pigment such as a lake pigment, the color pigment is mixed with a part or all of the solvent (E) in advance until the average particle size of the color pigment becomes about 0.2 μm or less. It is preferable to disperse using a bead mill or the like. At this time, if necessary, a part or all of the pigment dispersant and the resin (B) may be blended. When the colorant (A) further contains a color pigment different from the lake pigment, it is preferable to prepare a color pigment dispersion liquid in the same manner as the lake pigment dispersion liquid.
It is preferable that the extender pigment (P) is mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like. The coloring pigment and the extender pigment (P) may be mixed and dispersed together. The desired color-curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid thus obtained so as to have a predetermined concentration.

When the colorant (A) contains a dye, the dye may be dissolved in a part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution with a filter having a pore size of about 0.01 to 1 μm.

It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.01 to 10 μm.

<Manufacturing method of color filter>
The colored curable resin composition of the present invention is suitable as a material for a color filter. A color filter formed from the color curable resin composition of the present invention is also one of the present inventions.
The color filter of the present invention is formed by a method including a step of applying the coloring curable resin composition to a substrate, drying it to form a coloring composition layer, and curing the coloring composition layer by exposure or the like. Can be done. The color filter of the present invention has a colored pattern and a colored coating film.
Specific methods for producing the colored pattern include a photolithography method, an inkjet method, a printing method, and the like, and a photolithography method is preferable. The photolithography method is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film which is a cured product of the coloring composition layer can be formed by not using a photomask at the time of exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

The film thickness of the color filter of the present invention is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, 0.1 to 30 μm, preferably 0.1 to 20 μm, more preferably 0. It is 5 to 6 μm.

The substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate. Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass. Another color filter layer, resin layer, transistor, circuit and the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or conventional device or condition. For example, it can be produced as follows.

First, a colored curable resin composition is applied onto a substrate and dried by heating and drying (prebaking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth colored composition layer.

Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.

The temperature for heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

When drying under reduced pressure, it is preferable to carry out drying under a pressure of 50 to 150 Pa in a temperature range of 20 to 25 ° C.

The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.

The coloring composition layer is then exposed via a photomask to form the desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.

As the light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps and the like.

An exposure device such as a mask aligner and a stepper is used because it is possible to uniformly irradiate the entire exposed surface with parallel rays and accurately align the photomask with the substrate on which the coloring composition layer is formed. Is preferable.

A coloring pattern is formed on the substrate by developing the coloring composition layer after exposure by bringing it into contact with a developing solution. By development, the unexposed portion of the coloring composition layer is dissolved in a developing solution and removed.
As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.

The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to wash with water.

Further, it is preferable to post-bake the obtained coloring pattern. The post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

According to the color curable resin composition of the present invention, a color filter or the like having excellent heat resistance and solvent resistance can be produced. The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image sensor.

Hereinafter, the colored curable resin composition of the present invention will be described in more detail by way of examples.
Unless otherwise specified, "%" and "part" in the example are mass% and parts by mass.

<Production Example 1: Preparation of rake pigment (A1)>
The following reaction was carried out in a nitrogen atmosphere. After adding 15.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 60 parts of N, N-dimethylformamide to a flask equipped with a cooling tube and a stirrer, the obtained mixed solution was ice-cooled. .. After adding 5.7 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) little by little over 30 minutes under ice-cooling, the mixture was stirred for 1 hour while raising the temperature to room temperature. 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little to the reaction solution, and the mixture was stirred at room temperature for 24 hours. After adding the reaction solution to 200 parts of ice water little by little, the mixture was allowed to stand at room temperature for 15 hours, and the water was removed by decantation to obtain a viscous solid as a residue. After adding 60 parts of methanol to this viscous solid, the mixture was stirred at room temperature for 15 hours. The precipitated solid was filtered off and then purified by column chromatography. The purified pale yellow solid was dried under reduced pressure at 60 ° C. to obtain 9.8 parts of the compound represented by the formula (CI-18).

The following reaction was carried out in a nitrogen atmosphere. 8.2 parts of the compound represented by the following formula (BI-7), 10 parts of the compound represented by the above formula (CI-18) and 20 parts of toluene are placed in a flask equipped with a cooling tube and a stirrer. Was added, 12.2 parts of phosphorus oxychloride was added, and the mixture was stirred at 95 to 100 ° C. for 3 hours. The reaction mixture was then cooled to room temperature and then diluted with 170 parts isopropanol. Then, the diluted reaction solution was poured into 300 parts of saturated brine, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. When the stirring was stopped and the mixture was allowed to stand for 30 minutes, it was separated into an organic layer and an aqueous layer. After removing the aqueous layer by a liquid separation operation, the organic layer was washed with 300 parts of saturated brine. An appropriate amount of Glauber's salt was added to the organic layer, and the mixture was stirred for 30 minutes and then filtered to obtain a dried organic layer. The obtained organic layer was distilled off with an evaporator to obtain a bluish-purple solid. Further, the bluish purple solid was dried under reduced pressure at 60 ° C. to obtain 18.4 parts of the compound represented by the formula (A-II-18).

The following reaction was carried out in a nitrogen atmosphere. Eight parts of the compound represented by the above formula (A-II-18) and 396 parts of methanol were put into a flask equipped with a cooling tube and a stirrer, and then stirred at room temperature for 30 minutes to prepare a blue solution. Then, after adding 396 parts of water to this blue solution, the mixture was further stirred at room temperature for 30 minutes to obtain a reaction solution.

53 parts of water was put into a beaker, and 11.8 parts of kegin-type phosphotungstic acid (manufactured by Aldrich) and 53 parts of methanol were put into the water, mixed at room temperature in an air atmosphere, and phosphotungstic acid was added. A solution was prepared. The obtained phosphotungstic acid solution was added dropwise to the previously prepared reaction solution over 1 hour. After further stirring at room temperature for 30 minutes, the mixture was filtered to obtain a blue solid. The obtained blue solid was put into 200 parts of methanol, dispersed for 1 hour, and then filtered, and the operation was repeated twice. The blue solid obtained by the operation was put into 200 parts of water, dispersed for 1 hour, and then filtered, and the operation was repeated twice. The blue solid obtained by the operation was dried under reduced pressure at 60 ° C. to obtain 17.1 parts of the compound represented by the formula (AI-18) [rake pigment (A1)].

<Preparation of dispersion>
14 parts of the compound represented by the formula (AI-18), 2.5 parts of the dispersant (BYK (registered trademark) -LPN6919 (manufactured by Big Chemie Japan)), 6 parts of the resin (B1) (solid content conversion) , 77.5 parts of propylene glycol monomethyl ether acetate and 300 parts of 0.2 mm zirconia beads were mixed and shaken for 6 hours using a paint conditioner (manufactured by Red Devil) to prepare a dispersion liquid (1).

<Production Example 2: Preparation of xanthene dye (A2)>
20 parts of the compound represented by the following formula (1x) and 200 parts of N-propyl-2,6-dimethylaniline (manufactured by Wako Pure Chemical Industries, Ltd.) are mixed under light-shielding conditions, and the obtained solution is 110. The mixture was stirred at ° C. for 6 hours. The obtained reaction solution was cooled to room temperature, added to a mixed solution of 800 parts of water and 50 parts of 35% by mass hydrochloric acid, and stirred at room temperature for 1 hour to precipitate crystals. The precipitated crystals were obtained as a residue of suction filtration and then dried to obtain a compound represented by the formula (1-32) [xanthene dye (A2)].

<Production Example 3: Preparation of resin (B1)>
An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2.6] decane-8 and 3,4-epoxytricyclo [5.2.1.0 ^2.6] decane A mixed solution of 289 parts of a 1: 1 mixture of -9-ylacrylate and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a mixed solution prepared by dissolving 33 parts of 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the resin was kept at the same temperature for 4 hours, cooled to room temperature, and had a B-type viscosity (23 ° C.) of 125 mPas, a solid content of 35.1%, and an acid value of 115 mg-KOH / g in terms of solid content. The solution of B1) was obtained. The weight average molecular weight of the resin (B1) (Mw) is 1.06 × 10 ^4, the degree of dispersion was 2.08.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin were measured by using the GPC method under the following conditions.

Equipment: K2479 (manufactured by Shimadzu Corporation)
Column; SHIMADZU Shima-pack GPC-80M
Column temperature; 40 ° C
Solvent; tetrahydrofuran (THF)
Flow velocity; 1.0 mL / min
Detector; RI
Calibration standard material; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation).

The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above was defined as the degree of dispersion.

<Examples 1 to 4, Comparative Example 1>
(1) Preparation of Color Curable Resin Composition Each component shown in Table 1 was mixed to obtain a color curable resin composition. The unit of the blending amount of each component in Table 1 is "part by mass". As will be described later, the rake pigment (A1) and the extender pigments (P1) to (P4) are premixed with the dispersant, the resin (B1) and the solvent (E1) or (E4), and colored in a state of being a dispersion liquid. Although it was used for preparing the curable resin composition, Table 1 shows the content of each component contained in the finally obtained colored curable resin composition. The numerical values in Table 1 are the solid content (parts by mass) of each component.

Resin (B1): Shows the total content of the resin (B1).
Solvent (E1): Shows the total content of propylene glycol monomethyl ether acetate.

In Table 1, each component represents the following. Further, the resin (B1) showed a mass part in terms of solid content.
[1] Dispersion liquid (A1): Dispersion liquid (1)
[2] Dye (A2): Compound represented by the formula (1-32) obtained in Production Example 2 [3] Resin (B1): Resin (B1) obtained in Production Example 3.
[4] Polymerizable compound (C1): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
[5] Polymerization initiator (D1): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; oxime compound)
[6] Constituent pigment dispersion (P1): Zinc oxide dispersion. In preparing the color curable resin composition, zinc oxide (10 parts), an acrylic pigment dispersant (1.3 parts), and the solvent (E1) (88.7 parts) shown in Table 1 were mixed in advance. The dispersion obtained above was used as a compounding ingredient.
[7] Constituent pigment dispersion (P2): Titanium oxide dispersion. In preparing the color curable resin composition, titanium oxide (10 parts), an acrylic pigment dispersant (3 parts), and the solvent (E1) (87 parts) shown in Table 1 were mixed in advance. The dispersion was used as a compounding ingredient.
[8] Constituent pigment dispersion (P3): Silica dispersion (PGM-AC-0413; manufactured by Nissan Chemical Industries, Ltd.)
[9] Constituent pigment dispersion (P4): Zirconia dispersion (BF-20FS; manufactured by Sakai Chemical Co., Ltd.)
[10] Solvent (E1): Propylene glycol monomethyl ether acetate [11] Solvent (E2): Ethyl lactate [12] Solvent (E3): Propylene glycol diacetate [13] Solvent (E4): Propylene glycol monomethyl ether [14] Leveling agent (F1): Polyether-modified silicone oil (Tore Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.).

<Comparative example 2>
(A) Colorant; C.I. I. Pigment Blue 15: 6 (Pigment) 29.3 parts Acrylic pigment dispersant 10 parts Propylene glycol monomethyl ether acetate 194 parts were mixed and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion liquid.
Then
Total amount of pigment dispersion (A) Colorant; 1-1; Compound represented by formula (1-32) 3 parts (B) Resin; Resin (B-1) (solid content equivalent) 50 parts (C) Polymerization Sex compound; (C-1); Dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator; (D-1); N-benzoyloxy-1- (4) -Phenylsulfanylphenyl) Octane-1-one-2-imine (Irgacure OXE 01; manufactured by BASF; oxime compound) 8 parts (F) Leveling agent; (F-1); Polyether-modified silicone oil (Torre silicone SH8400; Toray Dow Corning Co., Ltd.) 0.2 part (E) solvent; (E-1); propylene glycol monomethyl ether acetate
682 parts (E) solvent; (E-4); 171 parts of propylene glycol monomethyl ether were mixed to obtain a colored curable resin composition.

<Comparative example 3>
(A) Colorant; C.I. I. Pigment Blue 15: 6 (Pigment) 29.5 parts Acrylic pigment dispersant 15 parts Propylene glycol monomethyl ether acetate 198 parts were mixed and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion liquid.
Then
Total amount of the pigment dispersion (A) Dispersion (A1): Dispersion (1) 82 parts (B) Resin; Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound; (C-1) ); Dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator; (D-1); N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- 1-ON-2-imine (Irgacure OXE 01; manufactured by BASF; oxime compound) 14 parts (F) Leveling agent; (F-1); polyether-modified silicone oil (Tore Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) ) 0.1 part (E) solvent; (E-1); propylene glycol monomethyl ether acetate
597 parts (E) solvent; (E-4); 149 parts of propylene glycol monomethyl ether were mixed to obtain a colored curable resin composition.

(2) Preparation of Colored Coating Film A colored curable resin composition was applied onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) by a spin coating method so that the film thickness after post-baking was 2 μm. Then, it was prebaked at 100 ° C. for 3 minutes to form a colored composition layer. After allowing to cool, the colored composition layer was irradiated with light at an exposure amount of ^{150 mJ / cm 2} (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). After light irradiation, post-baking was performed at 230 ° C. for 20 minutes in an oven to obtain a colored coating film.

(3) Evaluation of chromaticity The obtained colored coating film was spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the CIE XYZ table was used using the characteristic function of the C light source. The xy chromaticity coordinates (x, y) and the stimulus value Y in the color system were measured. The larger the value of Y, the higher the brightness. The results are shown in Table 2.

(4) Heat resistance evaluation The obtained colored coating film was heated at 230 ° C. for 2 hours in an oven. The xy chromaticity coordinates (x, y) and Y were measured before and after heating, and the color difference ΔEab * was calculated from the measured values by the method described in JIS Z 8730: 2009 (7. Color difference calculation method). The obtained calculated value was converted into a relative value (%) when ΔEab * of Comparative Example 1 was set to 100%. The results are shown in Table 2.

(5) Solvent resistance evaluation The obtained colored coating film was immersed in a large excess amount of N-methyl-2-pyrrolidone kept constant at 23 ° C. for 40 minutes, and then sufficiently washed with water. The xy chromaticity coordinates (x, y) and Y were measured before and after immersion, and the color difference ΔEab * was calculated from the measured values by the method described in JIS Z 8730: 2009 (7. Color difference calculation method). The obtained calculated value was converted into a relative value (%) when ΔEab * of Comparative Example 1 was set to 100%. The results are shown in Table 2.

According to the color curable resin composition of the present invention, it is possible to produce a color filter having improved solvent resistance and heat resistance, and further a color filter having high brightness.

Claims (4)

It contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and an extender pigment (P).
The colorant (A) contains a lake pigment and
The lake pigment contains a compound (Aa) consisting of an anion of a compound containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen, and a cation having a pigment skeleton.
The extender pigment (P) is zinc oxide, at least one selected from titanium oxide, silica and zirconia A or Ranaru group,
A color curable resin composition containing no silsesquioxane compound. The colored curable resin composition according to claim 1, wherein the compound (Aa) is a compound represented by the formula (AI).

[In the formula (AI), X ⁺ represents a cation represented by the formula (AIX). ]

[[Y] ^m- represents an m-valent anion containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus.
m represents an arbitrary natural number.
In the formula (AIX ^{), R 41 to R 44} are monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms and having 2 to 20 carbon atoms, which may have substituents independently of each other. It is an alkyl group and has a group in which an oxygen atom is inserted between methylene groups constituting the alkyl group (however, a plurality of oxygen atoms are not inserted adjacent to each other) and a substituent. It represents a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms, an aralkyl group having 7 to 11 carbon atoms which may have a substituent, or a hydrogen atom.
R ⁴¹ and R ⁴² may be bonded to form a ring with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may be bonded to form a ring with the nitrogen atom to which they are bonded.
R ^{47 to} R ⁵⁴ independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or an alkyl group having 1 to 8 carbon atoms, and when the number of carbon atoms is 2 or more, constitutes the alkyl group. An oxygen atom may be inserted between the methylene groups (however, a plurality of oxygen atoms are not inserted adjacent to each other). R ⁴⁸ and R ⁵² may be combined with each other to form -NH-, -O-, -S- or -SO _2- .
T ¹ represents a monovalent aromatic heterocyclic group which may have a substituent.
When m is a natural number of 2 or more, the plurality of X ⁺ may have the same structure or different structures. ] A color filter formed from the colored curable resin composition according to claim 1 or 2. A display device including the color filter according to claim 3.