KR102337048B1 - Colored curable resin composition, color filter and display apparatus comprizing the same - Google Patents

Abstract

contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and an extender pigment (P);
Coloring curable resin composition in which a coloring agent (A) contains a lake pigment.

Description

A colored curable resin composition, a color filter, and the display apparatus containing the same TECHNICAL FIELD

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

A coloring agent containing a dye and a pigment, an extender pigment, and a coloring agent dispersion obtained by dispersing the dispersing agent in a solvent containing propylene glycol monomethyl ether acetate, a colored curable composition containing a polymerizable compound and a polymerization initiator are known (Japanese Patent) Application Publication No. 2015-98590).

This invention provides the colored curable resin composition shown below, a color filter, and a display apparatus.

[1] contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and an extender pigment (P);

Coloring curable resin composition in which a coloring agent (A) contains a lake pigment.

[2] The lake pigment is a compound (Aa) consisting of an anion of a compound containing at least one element and oxygen selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and a cation having a pigment skeleton, The colored curable resin composition according to [1].

[3] The compound (Aa) is a formula (A-I):

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

[Y] ^m- represents at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and an m-valent anion containing oxygen.

m represents any natural number.

In the formula (AIX), R ⁴¹ to R ⁴⁴ are each independently a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent or an alkyl group having 2 to 20 carbon atoms, and an oxygen atom between the methylene groups constituting the alkyl group is an inserted group (provided that a plurality of oxygen atoms are not inserted adjacently), a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent, an aralkyl group having 7 to 11 carbon atoms which may have a substituent, or represents a hydrogen atom.

R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may combine to form a ring together 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 hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, and when carbon number is 2 or more, an oxygen atom is inserted between the methylene groups constituting the alkyl group (However, a plurality of oxygen atoms are not inserted adjacently). R ⁴⁸ and R ⁵² may combine 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, a plurality of X ⁺ may have the same structure or different structures.]

The colored curable resin composition according to [2], which is a compound represented by

[4] The colored curable resin composition according to any one of [1] to [3], wherein the extender (P) is at least one selected from the group consisting of zinc oxide, titanium oxide, silica and zirconia.

[5] A color filter formed from the colored curable resin composition according to any one of [1] to [4].

[6] A display device comprising the color filter according to [5].

<Colored Curable Resin Composition>

The colored 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 the colorant (A) contains a lake pigment do.

According to the colored curable resin composition of this invention containing this coloring agent (A) and an extender (P), the solvent resistance and heat resistance of a cured film (color filter etc.) can be improved.

In addition, unless otherwise indicated, the compound illustrated as each component in this specification can be used individually or in combination of multiple types.

[1] Colorant (A)

[1-1] Lake Pigment

The colorant (A) contains a lake pigment.

In the present specification, the lake pigment refers to a pigment made insoluble in water or a dye soluble in an organic solvent by a laking agent. The pigment has, for example, a solubility (23°C) of 1% by mass or less in propylene glycol monomethyl ether acetate or propylene glycol monomethyl ether.

Dyes that can form lake pigments include acid dyes, basic dyes, direct dyes, etc., and compounds classified as having a color other than pigments in the color index (published by The Society of Dyers and Colorists) However, known dyes described in Dyeing Notes (Shikisen) can be used.

Specific examples of the acid dye include CI 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. Acid Orange 7, 10, 11, 12, 15, 19, 20, 22, 28, 30, 52, 56, 74, 127; C. 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. Acid Yellow 1, 3, 17, 18, 23, 25, 36, 38, 42, 44, 54, 59, 72, 78, 151; C. I. Acid Brown 2, 4, 13, 19, 248; CI 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. Acid Green 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 25, 27.

Specific examples of the basic dye include CI 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. Basic Orange 1, 2, 4, 5, 14, 15, 16, 17, 18, 21, 22, 23, 24, 25, 29, 30, 33, 54, 69; CI 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 ; CI 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. Basic Brown 1, 16, 17, 18 ; CI 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. Basic Green 1, 4, 5 are mentioned.

Specific examples of the direct dye include C. I. Direct Blue 41, 77, 86, 87, 106, 107, 108, 109, 189, 190, 199, 264; C. I. Direct Violet 54.

Specific examples of the laking agent include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, tanol, tamol, heteropolyacid (phosphotungstic acid, molybdic phosphomolybdic acid, tungstomolybdic phosphotungstic acid, tungstic silicic acid) , silica molybdic acid, silicon tungstomolybdic acid, etc.), and isopolyacid (tungstic acid, molybdic acid, etc.).

As a specific lake pigment, CI 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; CI 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. Pigment Green 1, 2, 3, 4, 8, 9, 10, 12, 45 ; CI 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. Pigment Orange 17, 18, 19, 46 ; C. I. Pigment Yellow 18, 61, 61: 1, 62, 100, 104, 115, 133, 168, 169, 183, 191, 209, 209: 1, 212 and the like.

The lake pigment in the present invention may have a cation derived from the dye, or may have an anion derived from the dye. The lake pigment preferably has a cation derived from the dye.

Examples of the cation derived from the dye include a cation derived from a triarylmethane dye, a rhodamine dye, and a xanthene dye. The cation derived from the dye is preferably a triarylmethane-based dye, and more preferably a triarylmethane-based dye which may have a heterocyclic ring such as a thiazole group.

The lake pigment, when having a cation derived from the dye, typically 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.

As an anion in the lake pigment, isopolyacid ion (M _m1 O _n ) ^c- , heteropolyacid ion (X _l M _m1 O _n ) ^c- (in each formula, M is a poly atom, X is a hetero atom, l represents the composition ratio of hetero atoms, m1 represents the composition ratio of poly atoms, n represents the composition ratio of oxygen atoms, c represents an integer of 1 to 8), and the following anions.

(Wherein, M represents a boron atom or an aluminum atom. R ⁶¹ , R ⁶² , R ⁶³ and R ⁶⁴ are each independently a hydroxyl group, a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. , or a reactive group, provided ^{that at least one of R 61} , R ⁶² , R ⁶³ and R ⁶⁴ is a reactive group.)

[In formula (6), W ³ and W ⁴ each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W ³ and W ⁴ are combined to form a fluorinated alkanediyl group having 1 to 4 carbon atoms. do]

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

[In formula (8), Y ¹ represents a fluorinated alkanediyl group having 1 to 4 carbon atoms]

[In formula (9), Y ² represents a fluorinated alkyl group having 1 to 4 carbon atoms]

From the viewpoint of solvent resistance and heat resistance, the lake pigment is tungsten (W), molybdenum (Mo), vanadium (V), titanium (Ti), niobium (Nb), silicon (Si), phosphorus (P), arsenic ( Compound (AA) comprising an anion of a compound containing oxygen and at least one element selected from the group consisting of As), sulfur (S), iron (Fe) and cobalt (Co), and a cation having a dye skeleton Preferably, it is more preferably a compound (Aa) comprising 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 dye skeleton. .

The lake pigment in the present invention, more preferably, a basic dye (triarylmethane-based dye, rhodamine-based dye, etc.) and a polyacid lake pigment.

Polyacrylic acid, and the plurality of the oxo acid is condensed acid, isophthalic acid ion may be a poly (M _m1 O _n) ^c-, heteropoly acid ion (X _{l m1} O M _n) may be a ^c-. In the formula, M is a poly atom, X is a hetero atom, l is a composition ratio of a hetero atom, m1 is a composition ratio of a poly atom, n is an oxygen atom composition ratio, and c is an integer of 1 to 8.

As poly atom M, W, Mo, V, Ti, Nb etc. are mentioned, for example.

Examples of the hetero atom X include Si, P, As, S, Fe, Co, and the like.

Specific examples of the polyacid preferable from the viewpoint of solvent resistance and heat resistance include isopolyacids such as _{tungstic acid ion [W 10} O ₃₂ ] ^4- and molybdate ion [Mo ₆ O ₁₉ ] ^2-; Phosphorous tungsten ion [PW ₁₂ O ₄₀ ] ^3- , Silicate tungstate ion [SiW ₁₂ O ₄₀ ] ^4- , Phosphormolybdate ion [PMo ₁₂ O ₄₀ ] ^3- , Phosphostomolybdate ion [PW _12-x Mo _x O ₄₀ ] ^3- , H ₃ [PW _2-x Mo _x O ₇ ] ^4- containing heteropolyacids. More specifically, phosphotungstomolybdate ion [PW ₁₀ Mo ₂ O ₄₀ ] ^3- , [PW ₁₁ Mo ₁ O ₄₀ ] ^3- , and phosphotungstic acid ion [PW ₁₂ O ₄₀ ] ^3- are mentioned.

Among them, from the viewpoint of solvent resistance and heat resistance, the compound (Aa) is a formula (A-I):

It is preferable that it is a compound represented by

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

[Y] ^m- represents at least one element selected from the group consisting of W, Mo, Si and P, and an m-valent anion containing oxygen. m represents any natural number.

In the formula (AIX), R ⁴¹ to R ⁴⁴ are each independently a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent or an alkyl group having 2 to 20 carbon atoms, and an oxygen atom between the methylene groups constituting the alkyl group is an inserted group (provided that a plurality of oxygen atoms are not inserted adjacently), a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent, an aralkyl group having 7 to 11 carbon atoms which may have a substituent, or represents a hydrogen atom. R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may combine to form a ring together with the nitrogen atom to which they are bonded.

R ⁴⁷ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a nitro group, a hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, and having 2 or more carbon atoms An oxygen atom 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 combine 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, a plurality of X ⁺ may have the same structure or different structures.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁴¹ to R ⁴⁴ include 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, a decyl group, a dodecyl group, a C1-C20 linear alkyl group, such as a hexadecyl group and an icosyl group; 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; A C3-C20 alicyclic saturated hydrocarbon group, such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group, etc. are mentioned. Preferably, it is a C1-C12 linear or branched alkyl group, More preferably, it is a C1-C8 linear or branched alkyl group, More preferably, it is a C1-C6 straight-chain alkyl group. a chain or branched chain alkyl group.

Examples of the substituent that the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted amino group, etc. can be heard

Regarding R ⁴¹ to R ⁴⁴ , as an alkyl group having 2 to 20 carbon atoms and an oxygen atom interposed between methylene groups constituting the alkyl group, the group is —CH ₂ —O—CH ₃ , —CH ₂ —O-CH _2- CH ₃ group, -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 an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a hexadecyl group and an icosyl group having 2 to 20 carbon atoms. A linear alkyl group of ; and 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, it is a C2-C12 linear or branched alkyl group, More preferably, it is a C2-C8 linear or branched alkyl group, More preferably, it is a C2-C6 straight-chain alkyl group. a chain or branched chain alkyl group.

Examples of the monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms represented by R ⁴¹ to R ⁴⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, a butylphenyl group, and a naphthyl group. Examples of the substituent that the monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a cyano group, a nitro group, a hydroxyl group, an alkoxy group, and an alkoxy group having 1 to 8 carbon atoms. an alkyl group, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted amino group.

Examples of the aralkyl group having 7 to 11 carbon atoms represented by 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, a 2,3-dimethylphenylmethyl group, 2,4-dimethylphenylmethyl group, 2,5-dimethylphenylmethyl group, 2,6-dimethylphenylmethyl group, 3,4-dimethylphenylmethyl group, naphthylmethyl group, etc. are mentioned.

Examples of the substituent that the aralkyl group having 7 to 11 carbon atoms may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a cyano group, a nitro group, a hydroxyl group, an alkoxy group, and a substituted or unsubstituted amino group. and the like.

Examples of ^{the ring that R 41} and R ⁴² may combine to form together with the nitrogen atom to which they are bonded, and the ring that R ⁴³ and R ⁴⁴ may combine and form together with the nitrogen atom to which they are bonded include a pyrrole ring, p Rollidine ring, piperidine ring, imidazole ring, indole ring, purine ring, ethyleneimine ring, 1H-azirine ring, azacyclobutane ring, hexamethyleneimine ring, azatropylidene ring, imidazoline ring, A morpholine ring, a thiazine ring, a carbazole ring, etc. are mentioned.

Among them, ^{it is preferable that R 41} to R ⁴⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ include a linear alkyl group 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; and branched chain alkyl groups such as isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group and 2-ethylhexyl group. Preferably, it is a C1-C6 alkyl group, More preferably, they are a methyl group, an ethyl group, a propyl group, and a butyl group.

Regarding R ⁴⁷ to R ⁵⁴ , the alkyl group in which an oxygen atom is inserted between the methylene groups constituting the alkyl group is an alkyl group having 2 to 8 carbon atoms, and an oxygen atom is inserted between the methylene groups constituting the alkyl group, —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.

Among them, ^{it is preferable that R 47} to R ⁵⁴ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

Regarding T ¹ , the aromatic heterocycle constituting the monovalent aromatic heterocyclic group may be either monocyclic or polycyclic, pyrrole, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thia Sol, isothiazole, pyridine, pyrimidine, pyridazine, pyrazine, 1,2,3-triazine, quinoline, isoquinoline, quinazoline, indole, benzimidazole, benzofuran, purine, acridine, phenoxazine , and phenothiazine.

Examples of the substituent that the aromatic heterocyclic group may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a cyano group, a nitro group, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, and an alkoxy group having 1 to 8 carbon atoms. An alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted amino group, etc. are mentioned.

[Y] ^m- represents at least one element selected from the group consisting of W, Mo, Si and P, and an m-valent anion containing oxygen. m represents any natural number.

From the viewpoints of solvent resistance and heat resistance, the anion is preferably the above-mentioned polyacid, and its preferred specific example is as described above. m becomes like this. Preferably it is a natural number of 1-10, More preferably, it is a natural number of 1-6.

[1-2] dye

The colorant (A) may further contain a dye in addition to the lake pigment.

The dye is not particularly limited, and a known dye can be used, and a solvent dye, an acid dye, a direct dye, a mordant dye, etc. are mentioned. As a dye, the compound classified as having a color other than a pigment in the color index (published by The Society of Dyers and Colorists), and the well-known dye described in the dyeing notebook (Shikisen Corporation) can be mentioned. Further, 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, a Creidine dye, styryl dye, coumarin dye, quinoline dye, nitro dye, etc. are mentioned. Among these, organic solvent-soluble dyes are preferable.

Specifically, C. 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;

CI 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 dyes such as C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.;

CI 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;

CI 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;

CI 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;

CI 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 , 104, 105, 106, 109, etc. CI acid dyes;

CI 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 ;

CI 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;

CI 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 dyes such as C. I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc.;

C. I. Disperse Yellow 51, 54, 76;

C. I. Disperse Violet 26, 27;

C. I. Disperse dyes such as C. I. Disperse Blue 1, 14, 56, 60;

C. I. Basic Red 1, 10 ;

CI 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 dyes such as C. I. Basic Green 1;

C. I. Reactive Yellow 2, 76, 116;

C. I. Reactive Orange 16 ;

C. I. reactive dyes such as C. I. Reactive Red 36;

C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

CI 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. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

CI Mordant 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;

CI Modern 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. Mordine dyes such as C. I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc.;

C. I. vat dyes, such as C. I. vat green 1, etc. are mentioned.

What is necessary is just to select these dyes suitably according to the spectral spectrum of a desired color filter.

Especially, when using dye, it is preferable that the dye contains a xanthene dye from viewpoints, such as solvent resistance and heat resistance, and a viewpoint of obtaining favorable brightness.

A xanthene dye is a dye containing the compound which has a xanthene skeleton in a molecule|numerator. Xanthene dyes include, for example, CI Acid Red 51, 52, 87, 92, 94, 289, 388, CI Acid Violet 9, 30, 102, CI Basic Red 1 (Rhodamine 6G), 2, 3, 4 , 8, CI Basic Red 10, 11, CI Basic Violet 10 (Rhodamine B), 11, CI Solvent Red 218, CI Modern Red 27, CI Reactive Red 36 (Rose Bengal B), Sulphorodamine G, Japan The xanthene dye of Unexamined-Japanese-Patent No. 2010-32999, the xanthene dye of Unexamined-Japanese-Patent No. 4492760, etc. are mentioned. Especially, what melt|dissolves in the organic solvent is preferable.

Among these, as the xanthene dye, a dye containing a compound represented by the formula (1a) (hereinafter sometimes referred to as “compound (1a)”) is preferable.

Compound (1a) may be a tautomer thereof. When a xanthene dye is further contained as the colorant (A), the content of the compound (1a) in the xanthene dye is preferably 50 mass% or more, more preferably 70 mass% or more, still more preferably 90 mass% or more. . As the xanthene dye, it is preferable to use only compound (1a).

In the formula (1a), R ¹ to R ⁴ are each independently a hydrogen atom, an optionally substituted monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted monovalent aralkyl group having 7 to 20 carbon atoms or a substituent. denotes a monovalent aromatic hydrocarbon group of 6 to 10 carbon atoms which may have, -CH ₂ contained in the saturated hydrocarbon group and the aralkyl group - is -O-, -CO- or -NR ¹¹ - or may be substituted with. R ¹ and R ² may be united to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be united 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 NR ⁹ R ¹⁰ is represented.

R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

m represents the integer of 0-5. When m is 2 or more, some R<^5> may be same or different.

a represents an integer of 0 or 1.

X represents a halogen atom.

Z ⁺ represents ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and four 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 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH ₂ - contained in the saturated aliphatic hydrocarbon group is -O-, -CO-, - It may be substituted with NH- or -NR ^{8 -, and R 9} and R ¹⁰ may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.

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), when -SO ₃ ^- exists, the number is one.

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms for R ¹ to R ⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms optionally substituted with a halogen atom, -OH, -OR ⁸ , -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ R ⁸ , -SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ^{8 ,} or -SO ₂ NR ⁹ R ¹⁰ . Among these, as the _{^{substituents, -SO 3 -, -SO 3 H}} , -SO 3 - Z + and -SO ₂ NR ⁹ R ¹⁰ are preferred, and -SO ₃ ^- Z ⁺ and -SO ₂ NR ⁹ R ¹⁰ is more preferably. Roneun _{^{Z +, -SO 3 - - -SO}} 3 in this case is N ⁺ (R ¹¹⁾ ₄ are preferred. R ¹ ~ R ⁴ is a group of these, from the colored curable composition according to the present invention a composition containing a compound (1a) is less generation of foreign matter, can also be the solvent resistance, and heat resistance to form a more excellent color filter.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms for R ¹ to R ⁴ and R ⁸ to R ¹¹ include, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and a jade group. linear alkyl groups such as a tyl group, a nonyl group, a decyl group, a dodecyl group, a hexadecyl group, and an icosyl group; branched chain alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group and 2-ethylhexyl group; A C3-C20 alicyclic saturated hydrocarbon group, such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group, is mentioned.

Hydrogen atom-containing saturated hydrocarbon groups that in the R ¹ ~ R ⁴ are, for example, or may be substituted with a halogen atom.

Examples of the aralkyl group represented by R ¹ to R ⁴ include the same examples as the aralkyl group represented by ^{R 41} to R ^{44 .}

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

As a ring which R<^1> and R<^2> becomes one and forms, and R<^3> and R<^4> form as one, the following are mentioned, for example.

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, and an icosyloxycarbonyl group.

Examples of -SR ⁸ include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.

Examples of -SO ₂ R ⁸ include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.

Examples of -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.

As -SO ₂ NR ⁹ R ¹⁰ , a sulfamoyl group;

N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulf Pamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl 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-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-(1,3-dimethylbutyl)sulfamoyl group, N-(3,3-dimethylbutyl)sulfamo group Diyl, N-heptylsulfamoyl group, N-(1-methylhexyl)sulfamoyl group, N-(1,4-dimethylpentyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl) N-1 substituted sulfamoyl groups such as a sulfamoyl group, an N-(1,5-dimethyl)hexylsulfamoyl group, and an 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-isopropylmethylsulfamoyl group, N such as N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, N,N-heptylmethylsulfamoyl group, An N-2 substituted sulfamoyl group etc. are mentioned.

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 is more preferable.

1-4 are preferable and, as for m, 1 or 2 is more preferable.

As a C1-C6 alkyl group in R<^6> and R<^7> , Linear alkyl groups, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group; and branched chain alkyl groups such as isopropyl group, isobutyl group, isopentyl group and neopentyl group.

A benzyl group, a phenylethyl group, a phenylbutyl group, etc. are mentioned as a C7-10 aralkyl group in R<^11>.

Z ⁺ is ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ¹¹ ) ₄ .

The N ⁺ (R ¹¹⁾ ₄ roneun, it is of the four R ^11, preferably at least two of the monovalent saturated hydrocarbon group having a carbon number of 5-20. Moreover, 20-80 are preferable and, as for total carbon number of four R<^{11>, 20-60 are more preferable.} When ⁺ N(R ¹¹ ) ₄ is present in the ^{compound (1a) and R 11} is these groups, a color filter with few foreign substances can be formed from the colored curable resin composition of the present invention containing the compound (1a). .

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

In formula (2a), R ²¹ to R ²⁴ each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. R ²¹ and R ²² may be united to form a ring containing a nitrogen atom, and R ²³ and R ²⁴ may be united to form a ring containing a nitrogen atom.

R ²⁵ is -SO ₃ ^- shows the Z1 ⁺ or _{^{-SO 2 NHR 26 -, -SO 3}} H, -SO 3.

m1 represents the integer of 0-5. When m1 is 2 or more, a plurality of R ²⁵ 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 four R ²⁷ may be the same or different.

R ²⁷ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group.

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms for ^{R 21} to R ²⁴ in the formula (2a) include the same groups as those exemplified as the aromatic hydrocarbon group for ^{R 1} to R ^{4 above.}

The hydrogen atom-containing aromatic hydrocarbon groups, -SO ₃ ^- or may be substituted with Z1 ^+, -SO ₃ R ²⁶ or ^{_{-SO 2 NHR 26 -, -SO 3}} H, -SO 3.

In the formula (2a), R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon group are -SO ₃ ^- , - ^{_{SO 3 H, -SO 3 - Z1}} +, -SO 3 R 26 or -SO ₂ NHR ²⁶ group is preferably substituted by which,

More preferably, R ²¹ and R ²³ is a hydrogen atom, R ²² and R ²⁴ is a group 1-valent aromatic hydrocarbon group of 6 to 10 carbon atoms, hydrogen atoms contained in the aromatic hydrocarbon groups, -SO ₃ ^- Z1 ⁺ or - It is a group substituted with _{SO 2} NHR ^{26 .}

R ²¹ ~ R ²⁴ is when these groups, from the colored curable resin composition of the present invention containing a compound (2a), have solvent resistance, and heat resistance to form a more excellent color filter.

The ^{ring containing a nitrogen atom formed by R 21} and R ²² as one and the ring containing a nitrogen atom formed by R ²³ and R ²⁴ as one is the same as the ring formed by ^{R 1} and R ^{2 as one.} ring can be taken. Especially, an aliphatic heterocyclic ring is preferable. Examples of the aliphatic heterocyclic ring include the following rings.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms for R ²¹ to R ²⁴ , R ²⁶ and R ²⁷ include the same groups as those exemplified as the saturated hydrocarbon group for ^{R 8} to R ^{11 .}

It is preferable that the saturated hydrocarbon groups represented by R ²¹ to R ²⁴ are each independently a methyl group or an ethyl group.

A -SO ₃ R ^26, and -SO ₂ NHR ²⁶ R ²⁶ in the is a branched alkyl group having 3 to 20 carbon atoms are preferred, more preferably a branched alkyl group having a carbon number of 6-12, and 2-ethylhexyl The actual machine is more preferable. If R ²⁶ is these groups, a color filter excellent in 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 N ⁺ (R ²⁷⁾ ₄ roneun, it is of the four R ^27, preferably at least two of the monovalent saturated hydrocarbon group having a carbon number of 5-20. The total number of carbon atoms of R 4 is ²⁷ 20 to 80 is preferred, more preferably from 20 to 60. When ⁺ N(R ²⁷ ) ₄ is present in the ^{compound (2a), if R 27} is these groups, a color filter excellent in solvent resistance and heat resistance is formed from the colored curable resin composition of the present invention containing the compound (2a) can do.

1-4 are preferable and, as for m1, 1 or 2 is more preferable.

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

In the formula (3a), R ³¹ and R ³² each independently represent a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, the saturated hydrocarbon group and the hydrogen atom contained in the aralkyl group are , each may be substituted with a halogen atom, the hydrogen atom contained in the aromatic hydrocarbon group of the aralkyl group may be substituted with an alkoxy group having 1 to 3 carbon atoms, and —CH ₂ - may be substituted with -O-, -CO- or -NR ^{11 -.}

R ³³ and R ³⁴ each independently represent an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, or an alkylsulfonyl group having 1 to 4 carbon atoms.

R ³¹ and R ³³ may be united to form a ring containing a nitrogen atom, and R ³² and R ³⁴ may be united to form a ring containing a nitrogen atom.

p and q each independently represent the integer of 0-5. When p is 2 or more, some R ³³ may be same or different, and when q is 2 or more, some R ³⁴ may be same or different.

R ¹¹ has the same meaning as above.

Examples of the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms for R ³¹ and R ³² include a linear alkyl group 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; branched chain alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group and 2-ethylhexyl group; A C3-C10 alicyclic saturated hydrocarbon group, such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group, is mentioned.

R in the aralkyl group in the ³¹ and R ³² there may be mentioned phenylene group.

A methoxy group, an ethoxy group, a propoxy group, etc. are mentioned as a C1-C3 alkoxy group.

It is preferable that R ³¹ and R ³² each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 3 carbon atoms.

Examples of the alkyl group having 1 to 4 carbon atoms for 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, and a tert-butyl group.

Examples of the alkylsulfanyl group having 1 to 4 carbon atoms for R ³³ and R ³⁴ include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group and an isopropylsulfanyl group.

Examples of the alkylsulfonyl group having 1 to 4 carbon atoms for R ³³ and R ³⁴ include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group and an isopropylsulfonyl group.

R ³³ and R ³⁴ are preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group.

The integers of 0-2 are preferable and, as for p and q, 0 or 1 is preferable.

As compound (1a), the compound represented, for example by Formula (1-1) - Formula (1-43) is mentioned. In the formula, R ⁴⁰ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, more preferably a 2-ethylhexyl group.

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

Among these, the sulfonamidide of C.I. Acid Red 289, the quaternary ammonium salt of C.I. Acid Red 289, the sulfonamidide of C.I. Acid Violet 102, or the quaternary ammonium salt of C.I. Acid Violet 102 are preferable. As such a compound, the compound etc. which are represented by Formula (1-1) - Formula (1-8), Formula (1-11), or Formula (1-12) are mentioned, for example.

Moreover, the compound represented by any one of Formula (1-24) - Formula (1-33) is also preferable at the point excellent in solubility with respect to an organic solvent.

As the xanthene dye, a commercially available xanthene dye (for example, “Chugai Aminol Fast Pink RH/C” manufactured by Chugai Chemical Co., Ltd., “Rhodamin 6G” manufactured by Daoka Chemical Industry Co., Ltd.) can be used. . Moreover, it can also be synthesize|combined with reference to Unexamined-Japanese-Patent No. 2010-32999 using commercially available xanthene dye as a starting material.

[1-3] color pigment

The colorant (A), in addition to the lake pigment, may further contain a color pigment (however, it is different from the lake pigment). It does not specifically limit as a color pigment, A well-known color pigment can be used, For example, the pigment classified as a pigment by the color index (The Society of Dyers and Colorists publication) is mentioned.

As a color pigment, CI 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, 147, 148, 150, 153, 154, 166, 173, 194, 214 yellow pigments;

Orange pigments, such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

Reds such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 pigment;

C. I. Blue pigments, such as pigment blue 15, 15:3, 15:4, 15:6, 60;

C. I. Violet pigments, such as pigment violet 1, 19, 23, 29, 32, 36, 38;

Green pigments, such as C.I. Pigment Green 7, 36, 58;

C. I. Brown pigments, such as Pigment Brown 23 and 25;

C.I. Black pigments, such as Pigment Black 1 and 7; and the like.

As a color pigment, Blue pigments, such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments, such as CI pigment violet 1, 19, 23, 29, 32, 36, 38, are preferable, CI pigment blue 15:3, 15:6 and CI pigment violet 23 are more preferable, CI pigment Ment Blue 15:6 is more preferable. By containing said colored pigment, optimization of a transmission spectrum is easy and the light resistance and solvent resistance of a color filter become favorable.

Color pigments, if necessary, rosin treatment, surface treatment using a pigment derivative into which an acidic group or basic group is introduced, graft treatment to the pigment surface with a high molecular compound, etc., atomization treatment by sulfuric acid atomization method, etc., or to remove impurities Washing treatment with an organic solvent, water, etc., removal treatment by an ion exchange method of ionic impurities, etc. may be performed.

It is preferable that a color pigment has a uniform particle diameter. By containing a pigment dispersant and performing a dispersion process, the pigment dispersion liquid of the state in which the color pigment was uniformly disperse|distributed in the solution can be obtained.

As said pigment dispersant, surfactant, such as a cationic type, an anionic type, a nonionic type, an amphoteric type, a polyester type, a polyamine type, an acrylic type, etc. are mentioned. These pigment dispersants may be used individually or in combination of 2 or more type. As the pigment dispersant, as a trade name, KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Florene (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by CIBA), Azispur (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (manufactured by Big Chemi Corporation), and the like.

When using a pigment dispersant, the usage-amount becomes like this with respect to the total amount of a colored pigment. Preferably they are 1 mass % or more and 100 mass % or less, More preferably, they are 5 mass % or more and 50 mass % or less. When the usage-amount of a pigment dispersant exists in said range, there exists a tendency for the pigment dispersion liquid of a uniformly dispersed state to be obtained.

[1-4] Content rate of colorant (A)

To [ the content rate of a coloring agent (A) ] with respect to the total amount of solid content of colored curable resin composition, Preferably it is 5-60 mass %, More preferably, it is 8-55 mass %, More preferably, it is 10-50 mass %. . When the content rate of the coloring agent (A) is within the above range, the color density when a color filter is used is sufficient, and the resin (B) and the polymerizable compound (C) can be contained in a required amount in the composition, so that the mechanical strength is sufficient. pattern can be formed.

Here, the "total amount of solid content" in this specification means the quantity which subtracted content of the solvent from the total amount of colored curable resin composition. The total amount of solid content and the content rate of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography, for example.

From the viewpoint of solvent resistance and heat resistance, the content rate of the lake pigment in the colorant (A) is, in 100 mass% of the colorant (A), preferably 2.5 to 100 mass%, more preferably 45 to 100 mass%, and , More preferably, it is 75-100 mass %, Especially preferably, it is 90-100 mass %.

When the colorant (A) contains a dye, from the viewpoint of solvent resistance and heat resistance, the content rate of the dye in the colorant (A) is usually 0.1 to 98 mass% in 100 mass% of the colorant (A), preferably Preferably it is 0.1-60 mass %, More preferably, it is 0.1-50 mass %, More preferably, it is 0.5-25 mass %, Especially preferably, it is 0.5-10 mass %.

When the colorant (A) contains a color pigment, from the viewpoint of solvent resistance and heat resistance, the content rate of the color pigment in the colorant (A) is usually 0.1 to 98 mass% in 100 mass% of the colorant (A), , Preferably it is 0.1-60 mass %, More preferably, it is 0.1-50 mass %, More preferably, it is 5-25 mass %, Especially preferably, it is 0.5-10 mass %.

[2] Resin (B)

Although resin (B) is not specifically limited, It is preferable that it is alkali-soluble resin. As resin (B), the following resins [K1] - [K6], etc. are mentioned.

resin [K4.8/1281]; At least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (a) (hereinafter sometimes referred to as “(a)”), a cyclic ether structure having 2 to 4 carbon atoms, and ethylenic unsaturated a copolymer of a monomer (b) having a bond (hereinafter sometimes referred to as “(b)”);

resin [K2]; a copolymer of (a) and (b) and a monomer copolymerizable with (a) (c) (however, different from (a) and (b)) (hereinafter sometimes referred to as “(c)”);

resin [K3]; copolymers of (a) and (c);

resin [K4]; Resin in which (b) was made to react with the copolymer of (a) and (c);

resin [K5]; Resin which made (a) react with the copolymer of (b) and (c);

resin [K6]; Resin in which (a) was made to react with the copolymer of (b) and (c), and also carboxylic anhydride was made to react.

As (a), For example, unsaturated monocarboxylic acids, such as acrylic acid, methacrylic acid, a crotonic acid, o-, m-, p-vinyl benzoic 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 and 1, 4- cyclohexene dicarboxylic acid;

Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hepto-2-ene, 5,6-dicarboxybicyclo[2.2.1]hepto-2- ene, 5-carboxy-5-methylbicyclo[2.2.1]hepto-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hepto-2-ene, 5-carboxy-6-methylbi Bicyclo unsaturated compounds containing a carboxyl group, such as cyclo[2.2.1]hepto-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hepto-2-ene;

Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride , unsaturated dicarboxylic acid anhydrides such as dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride;

Unsaturated mono[(meth)acryloyloxyalkyl of divalent or higher polyhydric carboxylic acid, such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl] ]ester;

unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from the point of copolymerization reactivity and the solubility point with respect to the aqueous alkali solution of resin obtained.

(b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond say compound. As for (b), the monomer which has a C2-C4 cyclic ether and a (meth)acryloyloxy group is preferable.

In addition, in this specification, "(meth)acrylic acid" shows at least 1 sort(s) chosen from the group which consists of acrylic acid and methacrylic acid. Notations such as “(meth)acryloyl” and “(meth)acrylate” have the same meaning.

As (b), a monomer (b1) having an oxylanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), a monomer having an oxetanyl group and an ethylenically unsaturated bond (b2) (hereinafter “ (b2)"), a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc. are mentioned.

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

As (b1-1), glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinyl benzyl Glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α -Methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxy) methyl) 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(glycidyloxymethyl)styrene, etc. are mentioned. can

As (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl ( Meth) acrylate (eg, cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, cyclomer M100; manufactured by Daicel Co., Ltd.) , the compound represented by the formula (I), the compound represented by the formula (II), and the like.

[In formulas (I) and (II), R ^a 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 may be substituted with a hydroxyl group.

X ^a and X ^b represent a single bond, -R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.

R ^c represents a C1-C6 alkanediyl group.

* indicates a bond with O.]

A methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group etc. are mentioned as a C1-C4 alkyl group.

Examples of the alkyl group in which a hydrogen atom is substituted with hydroxy include a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1- Hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, etc. are mentioned. .

As R ^a and R ^b , Preferably, a hydrogen atom, a methyl group, a hydroxymethyl group, 1-hydroxyethyl group, and 2-hydroxyethyl group are mentioned, More preferably, a hydrogen atom and a methyl group are mentioned.

Examples of the alkanediyl group include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- 1,6-diyl group etc. are mentioned.

As X ^a and X ^b , Preferably a single bond, a methylene group, an ethylene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O- are mentioned, More preferably, a single bond, *- CH ₂ CH ₂ -O- is mentioned (* represents a bond with O).

As a compound represented by Formula (I), the compound etc. which are represented by any one of Formula (I-1) - Formula (I-15) are mentioned. 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) ) is preferable, and a compound represented by a formula (I-1), a formula (I-7), a formula (I-9) or a formula (I-15) is more preferable.

As a compound represented by Formula (II), the compound etc. which are represented by any one of Formula (II-1) - Formula (II-15) are mentioned. 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) ) is preferable, and a compound represented by Formula (II-1), Formula (II-7), Formula (II-9) or Formula (II-15) is more preferable.

The compound represented by the formula (I) and the compound represented by the formula (II) may be used independently, respectively, or may use 2 or more types together. When the compound represented by the formula (I) and the compound represented by the formula (II) are used together, their content ratio [the compound represented by the formula (I): the compound represented by the formula (II)] is preferably 5 on a molar basis :95 to 95:5, and more preferably 20:80 to 80:20.

As (b2), the monomer which has an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3 -Ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryl Royloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. are mentioned.

As (b3), the monomer which has a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. As (b3), tetrahydrofurfuryl acrylate (For example, Viscot V#150, Osaka Organic Chemical Co., Ltd. product), tetrahydrofurfuryl methacrylate etc. are mentioned specifically,.

As (b), it is preferable that it is (b1) from the point which can make higher reliability, such as heat resistance and chemical-resistance of the color filter obtained. Moreover, (b1-2) is more preferable at the point which is excellent in the storage stability of colored curable resin composition.

As (c), for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 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 ] decan-8-yl (meth) acrylate (in the technical field, as a common name, "dicyclopentanyl (meth) acrylate" Also called "tricyclodecyl (meth) acrylate" in some cases), tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate (in the technical field, a common name as "dicyclopentenyl (meth) acrylate"), dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) (meth)acrylic acid esters such as acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

Hydroxyl group-containing (meth)acrylic acid ester, 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]hepto-2-ene, 5-methylbicyclo[2.2.1]hepto-2-ene, 5-ethylbicyclo[2.2.1]hepto-2-ene, 5-hydroxybi Cyclo[2.2.1]hepto-2-ene, 5-hydroxymethylbicyclo[2.2.1]hepto-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hepto-2 -ene, 5-methoxybicyclo[2.2.1]hepto-2-ene, 5-ethoxybicyclo[2.2.1]hepto-2-ene, 5,6-dihydroxybicyclo[2.2.1]hepto -2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hepto-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hepto- 2-ene, 5,6-dimethoxybicyclo[2.2.1]hepto-2-ene, 5,6-diethoxybicyclo[2.2.1]hepto-2-ene, 5-hydroxy-5-methyl Bicyclo[2.2.1]hepto-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hepto-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1] Hepto-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hepto-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hepto-2-ene, 5-phenoxy Cycarbonylbicyclo[2.2.1]hepto-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hepto-2-ene, 5,6-bis(cyclohexylox Bicyclo unsaturated compounds, such as cycarbonyl)bicyclo[2.2.1]hepto-2-ene;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutylate, N-succinimidyl dicarbonylimide derivatives such as -6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl) maleimide;

Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, acetic acid vinyl, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene; and the like.

Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hepto-2-ene, etc. are preferable from the point of copolymerization reactivity and heat resistance. do.

In the resin [K1], the ratio of the structural units derived from each of the total structural units constituting the resin [K1],

A structural unit derived from (a); 2 to 60 mol%

a structural unit derived from (b); 40 to 98 mol%

It is preferable that

A structural unit derived from (a); 10 to 50 mol%

a structural unit derived from (b); 50 to 90 mol%

It is more preferable that

When the ratio of the structural unit of resin [K1] exists in said range, there exists a tendency excellent in the storage stability of a colored curable resin composition, the developability at the time of forming a colored pattern, and the solvent resistance of the color filter obtained.

Resin [K1] is, for example, the method described in the document "Experimental method of polymer synthesis" (Published by Takayuki Otsu, Co., Ltd. Chemical Dongin 1st Edition 1st Edition March 1, 1972) and citations described in the document It can be prepared with reference to the literature.

Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, for example, by replacing oxygen with nitrogen, a deoxidized atmosphere is created, and heating and keeping warm while stirring how to do it In addition, the polymerization initiator, a solvent, etc. used here are not specifically limited, Those normally used in the said field|area 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.) are mentioned, What is necessary is just to melt|dissolve each monomer as a solvent, The solvent etc. which are mentioned later as a solvent (E) of the colored curable resin composition of this invention are mentioned.

In addition, the obtained copolymer may use the solution after reaction as it is, may use the concentrated or diluted solution, and may use what was taken out as solid (powder) by methods, such as reprecipitation. In particular, by using the solvent contained in the colored 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 colored curable resin composition of the present invention, so the colored curable resin of the present invention The manufacturing process of the composition can be simplified.

In the resin [K2], the ratio of the structural units derived from each of the total structural units constituting the resin [K2],

A structural unit derived from (a); 2 to 45 mol%

a structural unit derived from (b); 2 to 95 mol%

a structural unit derived from (c); 1 to 65 mol%

It is preferable that

A structural unit derived from (a); 5 to 40 mol%

a structural unit derived from (b); 5 to 80 mol%

a structural unit derived from (c); 5 to 60 mol%

It is more preferable that

When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored curable resin composition, the developability at the time of forming a colored pattern, and the tendency for the solvent resistance, heat resistance and mechanical strength of the obtained color filter to be excellent There is this.

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

In the resin [K3], the ratio of the structural units derived from each of the total structural units constituting the resin [K3],

A structural unit derived from (a); 2 to 60 mol%

a structural unit derived from (c); 40 to 98 mol%

It is preferable that

A structural unit derived from (a); 10 to 50 mol%

a structural unit derived from (c); 50 to 90 mol%

It is more preferable that

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

Resin [K4] obtains the copolymer of (a) and (c), and adds the C2-C4 cyclic ether which (b) has to the carboxylic acid and/or carboxylic acid anhydride which (a) has. It can be manufactured by

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

Next, the C2-C4 cyclic ether which (b) has is made to react with a part of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the said copolymer.

Continuing with the preparation of the copolymers of (a) and (c), the atmosphere in the flask is substituted from nitrogen to air, and (b), a reaction catalyst of a carboxylic acid or carboxylic anhydride and a cyclic ether (tris(dimethyl Resin [K4] can be produced by putting aminomethyl) phenol etc.) and polymerization inhibitor (hydroquinone etc.) in a flask, and making it react at 60-130 degreeC for 1 to 10 hours, for example.

As for the usage-amount of (b), 5-80 mol is preferable with respect to (a) 100 mol, More preferably, it is 10-75 mol. By setting it as this range, there exists a tendency for the balance of the storage stability of colored curable resin composition, the developability at the time of forming a pattern, and solvent resistance, heat resistance, mechanical strength, and a sensitivity of the pattern obtained to become favorable. Since the reactivity of cyclic ether is high and unreacted (b) hardly remains, as (b) used for resin [K4], (b1) is preferable and (b1-1) is preferable.

As for the usage-amount of the said reaction catalyst, 0.001-5 mass parts is preferable with respect to 100 mass parts of total amounts of (a), (b), and (c). As for the usage-amount of the said polymerization inhibitor, 0.001-5 mass parts is preferable with respect to 100 mass parts of total amounts of (a), (b), and (c).

Reaction conditions, such as an injection|pouring method, reaction temperature, and time, can be suitably adjusted in consideration of manufacturing equipment, the amount of heat generated by polymerization, and the like. In addition, similarly to the polymerization conditions, the injection method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by polymerization, and the like.

Resin [K5] is a 1st step, it carries out similarly to the manufacturing method of resin [K1] mentioned above, and obtains the copolymer of (b) and (c). As for the copolymer obtained as described above, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, and the obtained copolymer may be used as a solid (powder) taken out by methods such as reprecipitation.

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.

a structural unit derived from (b); 5 to 95 mol%

a structural unit derived from (c); 5 to 95 mol%

It is preferable that

a structural unit derived from (b); 10 to 90 mol%

a structural unit derived from (c); 10 to 90 mol%

It is more preferable that

Further, under the same conditions as in the production method of the resin [K4], the carboxylic acid or carboxylic acid anhydride of (a) was added to the cyclic ether derived from (b) in the copolymers of (b) and (c). By making it react, resin [K5] can be obtained.

As for the usage-amount of (a) made to react with said copolymer, 5-80 mol is preferable with respect to 100 mol of (b). Since the reactivity of cyclic ether is high and unreacted (b) hardly remains, as (b) used for resin [K5], (b1) is preferable and (b1-1) is preferable.

Resin [K6] is resin in which carboxylic anhydride was further made to react with resin [K5]. A hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic acid anhydride is reacted with a carboxylic acid anhydride.

Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3 and 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride. As for the usage-amount of a carboxylic anhydride, 0.5-1 mol is preferable with respect to 1 mol of usage-amounts of (a).

Specifically as the resin (B), 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decylacrylate/(meth) Resin [K1], such as an acrylic acid copolymer; 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} ] Resins such as decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer [K2] ; Resin [K3], such as a benzyl (meth)acrylate/(meth)acrylic acid copolymer and a styrene/(meth)acrylic acid copolymer; A resin obtained by adding glycidyl (meth) acrylate to a benzyl (meth) acrylate/(meth) acrylic acid copolymer, and glycidyl (meth) to a tricyclodecyl (meth) acrylate/styrene/(meth)acrylic acid copolymer ) Resin to which acrylate was added, resin [K4], such as resin which added glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer; A resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate/glycidyl(meth)acrylate, tricyclodecyl(meth)acrylate/styrene/glycidyl(meth)acrylate Resin [K5], such as resin which made the copolymer react with (meth)acrylic acid; and resin [K6] such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid and further reacting with tetrahydrophthalic anhydride. have. Especially, as resin (B), resin [K1] and resin [K2] are preferable.

The weight average molecular weights (Mw) in terms of polystyrene of the resin (B) are preferably 3,000 to 100,000, more preferably 5,000 to 50,000, still more preferably 5,000 to 30,000. When molecular weight exists in said range, the hardness of a color filter improves, the residual film rate is high, the solubility with respect to the developing solution of an unexposed part is favorable, and there exists a tendency for the resolution of a coloring pattern to improve.

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

The acid value of resin (B) becomes like this. Preferably it is 50-170 mg-KOH/g, More preferably, it is 60-150, More preferably, it is 70-135 mg-KOH/g. Here, an acid value is a value measured as the quantity (mg) of potassium hydroxide required in order to neutralize 1 g of resin (B), For example, it can obtain|require by titrating using potassium hydroxide aqueous solution.

To [ the content rate of resin (B) ] with respect to the total amount of solid content of colored curable resin composition, Preferably it is 7-65 mass %, More preferably, it is 13-60 mass %, More preferably, it is 17-55 mass % . If the content rate of resin (B) exists in said range, a coloring pattern can be formed, and there exists a tendency for the resolution and residual film rate of a coloring pattern to improve.

[3] Polymerizable compound (C)

The polymerizable compound (C) is a compound that can be polymerized with an active radical and/or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, etc., preferably Preferably, it is a (meth)acrylic acid ester compound.

Especially, it is preferable that a polymeric compound (C) is a polymeric compound which has 3 or more of ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and di Pentaerythritol hexa (meth) 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, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) Acrylates etc. are mentioned.

Especially, 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, more preferably 250 to 1,500 or less.

It is preferable that the content rate of a polymeric compound (C) is 7-65 mass % with respect to the total amount of solid content of colored curable resin composition, More preferably, it is 13-60 mass %, More preferably, it is 17-55 mass %. % am. When the content rate of a polymeric compound (C) exists in said range, there exists a tendency for the residual film rate at the time of coloring pattern formation and the solvent resistance of a color filter to improve.

[4] polymerization initiator (D)

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

The said O-acyl oxime compound is a compound which has a structure represented by Formula (d1). Hereinafter, * represents a bond.

Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane -1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl -6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3) -Dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methyl) Benzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3 -yl]-3-cyclopentylpropan-1-one-2-imine; and the like. You may use commercial items, such as Irgacure OXE01, OXE02 (above, BASF Corporation make), and N-1919 (made by ADEKA Corporation). Among them, the O-acyloxime compound is N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl) At least one selected from the group consisting of octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferable , N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferable. If it is these O-acyl oxime compounds, there exists a tendency for the color filter of high brightness to be obtained.

The said alkylphenone compound is a compound which has a structure represented by Formula (d2) or a structure represented by Formula (d3). Among these structures, the benzene ring may have a substituent.

Examples of the compound having a structure represented by the formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morph Polynophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1- On and so on. You may use commercial items, such as Irgacure 369, 907, 379 (above, BASF Corporation make).

Examples of the compound having a structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1-[4-(2-hydroxyl). Ethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one oligomer, α,α -diethoxyacetophenone, benzyl dimethyl ketal, etc. are mentioned.

From the viewpoint of sensitivity, the alkylphenone compound is preferably a compound having a structure represented by Formula (d2).

Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 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-methoxystyryl)-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-(furan-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. are mentioned.

2,4,6-trimethylbenzoyl diphenylphosphine oxide etc. are mentioned as said acylphosphine oxide compound. You may use commercial items, such as Irgacure (trademark) 819 (made by BASF).

Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl) )-4,4',5,5'-tetraphenylbiimidazole (see Japanese Patent Application Laid-Open No. 6-75372, Japanese Patent Application Laid-Open No. 6-75373, etc.), 2,2'-bis(2- Chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimi Dazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4, 4',5,5'-tetra(trialkoxyphenyl)biimidazole (refer to Japanese Patent Publication No. 48-38403, Japanese Unexamined Patent Publication No. 62-174204, etc.), 4,4'5,5'-position and imidazole compounds in which the phenyl group of is substituted with a carboalkoxy group (see Japanese Patent Application Laid-Open No. 7-10913, etc.) and the like.

Moreover, as a polymerization initiator (D), Benzoin compounds, such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Benzophenone, o-benzoyl methylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone , benzophenone compounds such as 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compound, etc. are mentioned. It is preferable to use these in combination with the polymerization initiation adjuvant (D1) (particularly an amine compound) mentioned later.

Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4- Acetoxyphenyl methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyl iodine Onium salts, such as nium hexafluoroantimonate, nitrobenzyl tosylate, benzointosylate, etc. are mentioned.

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 O - The polymerization initiator containing an acyl oxime compound is more preferable.

To [ content of a polymerization initiator (D) / 100 mass parts of total amounts of resin (B) and a polymeric compound (C)), Preferably it is 0.1-30 mass parts, More preferably, it is 1-20 mass parts. When content of a polymerization initiator (D) exists in said range, since there exists a tendency for it to become highly sensitive and exposure time to shorten, productivity of a color filter improves.

[5] Auxiliary for polymerization initiation (D1)

The colored curable resin composition of this invention can contain a polymerization initiation adjuvant (D1). A polymerization initiation adjuvant (D1) is a compound used in order to accelerate|stimulate superposition|polymerization of the polymeric compound which superposition|polymerization was started by a polymerization initiator, or a sensitizer. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D). As a polymerization initiation adjuvant (D1), an amine compound, an alkoxyanthracene compound, a thioxanthone compound, a carboxylic acid compound, etc. are mentioned.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- Dimethylaminobenzoic acid 2-ethylhexyl, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4 ,4'-bis(ethylmethylamino)benzophenone etc. are mentioned, Especially, 4,4'-bis(diethylamino)benzophenone is preferable. You may use commercial items, such as EAB-F (made by Hodogaya Chemical Industry Co., Ltd.).

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10 -dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc. are mentioned.

As the thioxanthone compound, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-pro Foxythioxanthone etc. are mentioned.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, and dimethoxyphenylsulfanylacetic acid. , chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

When using these polymerization initiation adjuvants (D1), the content is with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), Preferably it is 0.1-30 mass parts, More preferably, it is 1-30 mass parts. 20 parts by mass. When the amount of the polymerization initiation auxiliary agent (D1) is within this range, a coloring pattern can be formed more highly sensitively and the productivity of the color filter tends to be improved.

[6] Extender Pigment (P)

The colored curable resin composition of this invention contains an extender (P). According to the colored curable resin composition of this invention containing the coloring agent (A) and the extender (P) mentioned above, the solvent resistance and heat resistance of a cured film (color filter etc.) can be improved.

It does not specifically limit as an extender pigment (P), A well-known extender pigment can be used, Zinc oxide (ZnO), titanium oxide (TiO ₂ ), silica (SiO ₂ ), zirconia (ZrO ₂ ), barium carbonate (BaCO _{3 )} ), lime carbonate (CaCO ₃ ), basic magnesium carbonate (MgCO ₃ ), aluminum hydroxide (Al(OH) ₃ ), kaolin clay, and extender pigments such as nephelincinite.

Among them, from the viewpoint of solvent resistance and heat resistance, the extender pigment (P) is preferably at least one selected from the group consisting of zinc oxide, titanium oxide, silica, zirconia, barium carbonate, lime carbonate and basic magnesium carbonate, It is more preferable that it is at least 1 sort(s) chosen from the group which consists of zinc oxide, a titanium oxide, a silica, and a zirconia. Moreover, from the point of obtaining the composition which can manufacture a color filter with high brightness among these, a thing with high transparency is more preferable. Since transparency is high, it is preferable that a primary particle diameter is 0.1 micrometer or less, and, as for an extender pigment (P), it is more preferable that it is 0.05 micrometer or less. The primary particle diameter of an extender pigment (P) is 0.01 micrometer or more normally.

With respect to the total amount of solid content of colored curable resin composition, the content rate of an extender pigment (P) becomes like this. Preferably it is 0.5-10 mass %, More preferably, it is 1-7 mass %, More preferably, it is 1.5-5 mass %. am. When the content rate of an extender pigment (P) exists in said range, when improving solvent resistance and heat resistance, it is advantageous.

[7] Solvent (E)

The colored curable resin composition of this invention can contain the solvent (E). The solvent (E) is not specifically limited, The solvent normally used in this field|area can be used. As the solvent (E), 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-), Ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (containing OH in the molecule and , -O-, -CO- and -COO--free solvent), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. are mentioned.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, 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.

Ether solvents 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, 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 ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol and methylani A brush etc. are mentioned.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3-ethoxypropionic acid Methyl, 3-ethoxy ethyl propionate, 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-methoxy propyl propionate, 2-ethoxy methyl propionate, 2-ethoxy ethyl propionate, 2-methoxy-2 -Methyl propionate, 2-ethoxy-2-methylpropionate ethyl, 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 ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, etc. are mentioned.

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 the like.

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

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, organic solvents having a boiling point of 120°C or more and 180°C or less at 1 atm are preferable from the viewpoint of coating properties and drying properties. As a solvent, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxy ethyl propionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hyde Roxy-4-methyl-2-pentanone and N,N-dimethylformamide are preferable, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are more preferable.

To [ content rate of a solvent (E) ] the total amount of the colored curable resin composition of this invention, Preferably it is 70-95 mass %, More preferably, it is 75-92 mass %. In other words, the total amount of solid content of colored curable resin composition becomes like this. Preferably it is 5-30 mass %, More preferably, it is 8-25 mass %. When the content rate of a solvent (E) exists in said range, since the flatness at the time of application|coating becomes favorable and color density does not run short when a color filter is formed, there exists a tendency for a display characteristic to become favorable.

[8] Leveling agent (F)

The colored curable resin composition of this invention can contain a leveling agent (F). As a leveling agent (F), the silicone type surfactant (which does not have a fluorine atom), the silicone type surfactant which has a fluorine type surfactant, and a fluorine atom, etc. are mentioned. These may have a polymeric group in a 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, and the like. Specifically, Toray silicone DC3PA, copper SH7PA, copper DC11PA, copper SH21PA, copper SH28PA, copper SH29PA, copper SH30PA, copper SH8400 (trade name: Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan joint venture), etc. can be heard

As said fluorochemical surfactant, the surfactant etc. which have a fluorocarbon chain in a molecule|numerator are mentioned. Specifically, Florad (registered trademark) FC430, Dong FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megapac (registered trademark) F142D, Dong F171, Dong F172, Dong F173, Dong F177, Dong F183, Dong F554, Dong R30, RS-718-K (manufactured by DIC Co., Ltd.), FTOP (registered trademark) EF301, EF303, copper EF351, EF352 (manufactured by Mitsubishi Material Electron Chemicals, Ltd.), Surflon (registered trademark) S381 , copper S382, copper SC101, copper SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Institute), and the like.

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 Megapac (registered trademark) R08, Dong BL20, Dong F475, Dong F477, and Dong F443 (manufactured by DIC Corporation).

With respect to the total amount of colored curable resin composition, the content rate of a leveling agent (F) becomes like this. Preferably they are 0.001 mass % or more and 0.2 mass % or less, Preferably they are 0.002 mass % or more and 0.1 mass % or less, More preferably, they are 0.01 mass %. or more and 0.05 mass% or less. In addition, the said pigment dispersant is not contained in this content rate. When the content rate of a leveling agent (F) exists in said range, the flatness of a color filter can be made favorable.

[9] Other ingredients

The colored curable resin composition of this invention may contain well-known additives in this technical field, such as another high molecular compound, an adhesion promoter, antioxidant, an optical stabilizer, and a chain transfer agent, further as needed.

<Method for producing colored curable resin composition>

The colored curable resin composition of this invention is a coloring agent (A), resin (B), a polymeric compound (C), a polymerization initiator (D), and an extender (P), and the solvent (E) used as needed, leveling It can prepare by mixing the agent (F), the polymerization initiation auxiliary agent (D1), and other components.

The lake pigment is preferably mixed with a part or all of the solvent (E) in advance, and dispersed using a bead mill or the like until the average particle diameter of the color pigment is about 0.2 µm or less. At this time, you may mix|blend a part or all of the said pigment dispersant and resin (B) as needed. When the colorant (A) further contains a color pigment, it is preferable to prepare a dispersion liquid of the color pigment in the same manner as the dispersion liquid of the lake pigment.

It is preferable to mix an extender pigment (P) with a part or all of a solvent (E) beforehand, and to disperse|distribute it using a bead mill etc. The color pigment and the extender pigment (P) may be mixed and dispersed together. Thus, by mixing the remaining component with the obtained pigment dispersion liquid so that it may become a predetermined density|concentration, the target colored curable resin composition can be prepared.

The dye in case a coloring agent (A) contains dye may be previously melt|dissolved in one part or all of a solvent (E), respectively, and may prepare a solution. It is preferable to filter the solution through a filter with a pore diameter of about 0.01 to 1 µm.

It is preferable to filter the colored curable resin composition after mixing with a filter with a pore diameter of about 0.01-10 micrometers.

<Method for manufacturing color filter>

The colored curable resin composition of this invention is suitable as a material of a color filter. The color filter formed from the colored curable resin composition of this invention is also one of this invention.

The color filter of this invention can be formed by the method including the process of apply|coating the said colored curable resin composition to a board|substrate, drying, forming a coloring composition layer, and hardening the coloring composition layer by exposure etc. The color filter of this invention has a coloring pattern and a coloring coating film.

A photolithographic method, an inkjet method, a printing method, etc. are mentioned as a specific method of manufacturing a coloring pattern. Especially, the photolithographic method is preferable. The photolithography method is a method of apply|coating the said colored curable resin composition to a board|substrate, drying it, forming a coloring composition layer, exposing the coloring composition layer through a photomask, and developing. The photolithographic method WHEREIN: The colored coating film which is hardened|cured material of the said coloring composition layer can be formed by not using and/or developing a photomask at the time of exposure.

The film thickness of the color filter of this invention is not specifically limited, According to the objective, a use, etc., it can adjust suitably, For example, 0.1-30 micrometers, Preferably it is 0.1-20 micrometers, More preferably, it is 0.5-6 micrometers. am.

As the substrate, a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or soda lime glass coated with silica, a resin plate such as polycarbonate, polymethyl methacrylate or polyethylene terephthalate, silicone, or on the substrate What formed the thin film of aluminum, silver, silver/copper/palladium alloy, etc. is used. On these board|substrates, another color filter layer, a resin layer, a transistor, a circuit, etc. may be formed.

Formation of each color pixel by the photolithographic method can be performed with a well-known or customary apparatus and conditions. For example, it can manufacture as follows.

First, a colored curable resin composition is apply|coated on a board|substrate, volatile components, such as a solvent, are removed and dried by heat-drying (pre-baking) and/or drying under reduced pressure, and a smooth coloring composition layer is obtained.

As a coating method, the spin coating method, the slit coating method, the slit and spin coating method, etc. are mentioned.

30-120 degreeC is preferable and, as for the temperature in the case of heat-drying, 50-110 degreeC is more preferable. Moreover, as heating time, it is preferable that they are for 10 second - 60 minutes, and it is more preferable that they are 30 second - 30 minutes.

When drying under reduced pressure, it is preferable to carry out under the pressure of 50-150 Pa at the temperature range of 20-25 degreeC.

The film thickness of the coloring composition layer is not specifically limited, What is necessary is just to select suitably according to the film thickness of the color filter made into the objective.

Next, the coloring composition layer is exposed through the photomask for forming the target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.

As a light source used for exposure, the light source which generate|occur|produces the light of the wavelength of 250-450 nm is preferable. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, or 365 nm is extracted using a bandpass filter that extracts these wavelength ranges. Thus, it may be selectively taken out. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned.

It is preferable to use exposure apparatuses, such as a mask aligner and a stepper, in order to irradiate a parallel light beam uniformly to the whole exposure surface, and to accurately position a photomask and the board|substrate on which the coloring composition layer was formed.

A coloring pattern is formed on a board|substrate by making a developing solution contact and developing the coloring composition layer after exposure. By image development, the unexposed part of a coloring composition layer melt|dissolves in a developing solution, and is removed. As a developing solution, the aqueous solution of alkaline compounds, such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, and tetramethylammonium hydroxide, is preferable. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01 to 10 mass%, more preferably 0.03 to 5 mass%. Moreover, the developing solution may contain surfactant.

Any of a paddle method, a dipping method, a spray method, etc. may be sufficient as the image development method. Moreover, you may incline a board|substrate at an arbitrary angle at the time of development. After image development, it is preferable to wash with water.

Moreover, it is preferable to post-baking to the obtained coloring pattern. 150-250 degreeC is preferable and, as for post-baking temperature, 160-235 degreeC is more preferable. 1 to 120 minutes are preferable and, as for post-baking time, 10 to 60 minutes are more preferable.

ADVANTAGE OF THE INVENTION According to the colored curable resin composition of this invention, the color filter excellent in heat resistance and solvent resistance can be manufactured. The color filter is useful as a color filter used for a display device (a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor.

Example

Hereinafter, the colored curable resin composition of this invention is demonstrated in detail by an Example. "%" and "part" in an example are mass % and a mass part, unless otherwise indicated.

<Production Example 1: Preparation of lake pigment (A1)>

The following reaction was performed in nitrogen atmosphere. After putting 15.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 60 parts of N,N-dimethylformamide into a flask equipped with a cooling tube and a stirring device, 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 heating to room temperature. 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) was gradually added to the reaction solution, followed by stirring at room temperature for 24 hours. After adding the reaction liquid little by little to 200 parts of ice water, it left still at room temperature for 15 hours, water was removed by decantation, and the viscous solid was obtained as a residue. After adding 60 parts of methanol to this viscous solid, it stirred at room temperature for 15 hours. The precipitated solid was separated by filtration and purified by column chromatography. The purified pale yellow solid was dried at 60°C under reduced pressure to obtain 9.8 parts of a compound represented by the formula (C-I-18).

The following reaction was performed in nitrogen atmosphere. In a flask equipped with a cooling tube and a stirring device, 8.2 parts of the compound represented by the formula (BI-7), 10 parts of the compound represented by the formula (CI-18), and 20 parts of toluene were added, and then 12.2 parts of phosphorus oxychloride was added, It stirred at 95-100 degreeC for 3 hours. The reaction mixture is then cooled to room temperature and then diluted with 170 parts of isopropanol. Next, the diluted reaction solution was poured into 300 parts of saturated brine, and then 100 parts of toluene was added, followed by stirring for 30 minutes. When stirring was stopped and left still for 30 minutes, it wasolate|separated into an organic layer and an aqueous layer. After the aqueous layer was removed by liquid separation, the organic layer was washed with 300 parts of saturated brine. After adding an appropriate amount of red peppercorns to the organic layer and stirring for 30 minutes, filtration was performed to obtain a dried organic layer. The obtained organic layer was solvent-distilled by the evaporator, and the blue-violet solid was obtained. Furthermore, the blue-violet solid was dried at 60 degreeC under reduced pressure, and 18.4 parts of compounds represented by Formula (A-II-18) were obtained.

The following reaction was performed in nitrogen atmosphere. To a flask equipped with a cooling tube and a stirring device, 8 parts of the compound represented by the formula (A-II-18) and 396 parts of methanol were charged, followed by stirring at room temperature for 30 minutes to prepare a blue solution. Next, after throwing in 396 parts of water to this blue solution, it stirred at room temperature for 30 minutes, and obtained the reaction solution.

Into 53 parts of water, 11.8 parts of Kegin type tungstic acid (manufactured by Aldrich) and 53 parts of methanol were put into the beaker, and the mixture was mixed at room temperature in an air atmosphere to prepare a phosphotungstic acid solution. The obtained phosphotungstic acid solution was dripped over 1 hour in the reaction solution prepared previously. Furthermore, after stirring at room temperature for 30 minutes, it filtered and obtained blue solid. After putting the obtained blue solid in 200 parts of methanol and disperse|distributing it for 1 hour, operation of filtering was repeated twice. The blue solid obtained by the operation was thrown into 200 parts of water and dispersed for 1 hour, and then the operation of filtration was repeated twice. The blue solid obtained by the operation was dried at 60°C under reduced pressure to obtain 17.1 parts of a compound [lake pigment (A1)] represented by the formula (A-I-18).

<Preparation of dispersion>

14 parts of the compound represented by the formula (AI-18), 2.5 parts of a dispersant (BYK (registered trademark)-LPN6919 (manufactured by Big Chemie Japan)), 6 parts of Resin (B1) (in terms of solid content), 6 parts of propylene glycol monomethyl ether acetate 77.5 parts and 300 parts of 0.2 mm zirconia beads were mixed, and it shook for 6 hours using the paint conditioner (made by Red Devil), and the dispersion liquid (A1) was prepared.

<Production Example 2: Preparation of xanthene dye (A2)>

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

<Production Example 3: Preparation of Resin (B1)>

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was poured into the flask, replaced with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was put, and the mixture was heated to 80°C while stirring.

Then, 38 parts of acrylic acid, a mixture of ^{3,4-epoxytricyclo[5.2.1.0 2.6} ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2.6]decan-9-ylacrylate 289} and a mixed solution of 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours.

On the other hand, a mixed solution obtained 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 dropwise addition, it was maintained at the same temperature for 4 hours, cooled to room temperature, and a solution of resin (B1) having a B-type viscosity (23°C) of 125 mPas, a solid content of 35.1%, and an acid value in terms of solid content of 115 mg-KOH/g got Resin (B1) had a weight average molecular weight (Mw) of 1.06 × 10 ⁴ and a dispersion degree of 2.08.

The measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) of resin was performed on condition of the following using GPC method.

Device ; K2479 (manufactured by Shimadzu Corporation)

column ; SHIMADZU Shim-pack GPC-80M

column temperature; 40 ℃

solvent; Tetrahydrofuran (THF)

flow rate ; 1.0 ml/min

detector ; RI

standard for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation).

Ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight and number average molecular weight obtained above was made into dispersibility.

<Examples 1 to 4, Comparative Example 1>

(1) Preparation of colored curable resin composition

Each component of Table 1 was mixed, and colored curable resin composition was obtained. The unit of the compounding quantity of each component in Table 1 is "mass part." As will be described later, with respect to the lake pigment (A1) and the extender pigments (P1) to (P4), the dispersant, the resin (B1) and the solvent (E1) or (E4) are mixed in advance with the color curable in a state as a dispersion. Although it used for preparation of a resin composition, in Table 1, content of each component contained in the finally obtained colored curable resin composition is shown. The numerical value of Table 1 is the solid content (mass part) of each component.

Resin (B1): The sum total of resin (B1) content is shown.

Solvent (E1): The sum total of propylene glycol monomethyl ether acetate content is shown.

In addition, in Table 1, each component shows the following. In addition, resin (B1) showed the mass part in conversion of solid content.

[1] Dispersion (A1): Dispersion (1)

[2] Dye (A2): a compound represented by formula (1-32) obtained in Production Example 2

[3] Resin (B1): Resin (B1) obtained in Production Example 3

[4] Polymeric compound (C1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[5] Polymerization initiator (D1): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; oxime compound) )

[6] Extender pigment dispersion (P1): Zinc oxide dispersion. In the preparation of the colored curable resin composition, zinc oxide (10 parts), an acrylic pigment dispersant (1.3 parts) and a solvent (E1) (88.7 parts) shown in Table 1 were mixed in advance, and a dispersion obtained was used as a compounding component.

[7] Extender pigment dispersion (P2): titanium oxide dispersion. In the preparation of the colored curable resin composition, a dispersion obtained by previously mixing titanium oxide (10 parts), an acrylic pigment dispersant (3 parts) and a solvent (E1) (87 parts) shown in Table 1 was used as a compounding component.

[8] Extender pigment dispersion (P3): Silica dispersion (PGM-AC-0413; manufactured by Nissan Chemical Industry Co., Ltd., product containing 30% of extender pigment)

[9] Extender pigment dispersion (P4): Zirconia dispersion (SZR; Sakai Chemical Co., Ltd. product containing 30% of extender pigment)

[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 (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.).

(2) Preparation of colored coating film

On a 5 cm vertical glass substrate (Eagle 2000; manufactured by Corning), the colored curable resin composition is applied by spin coating so that the post-baking film thickness may be 2 µm, and then pre-baked at 100°C for 3 minutes to color. A composition layer was formed. After standing to cool, the coloring composition layer was irradiated with light at an exposure amount of 150 mJ/cm 2 (based on 365 nm) in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). After light irradiation, in oven, it post-baked at 230 degreeC for 20 minutes, and obtained the colored coating film.

(3) Chromaticity evaluation

With respect to the obtained colored coating film, spectroscopy was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and xy chromaticity coordinates (x, y) in the XYZ color system of CIE using the characteristic function of the C light source. ) and the stimulus value Y were measured. It shows that the brightness is so high that the value of Y is large. A result is shown in Table 2.

(4) Heat resistance evaluation

The obtained colored coating film was heated at 230 degreeC in oven for 2 hours. 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. Calculation method of color difference). The calculated value obtained was converted into the relative value (%) when ΔEab* of Comparative Example 1 was 100%. A result is shown in Table 2.

(5) Evaluation of solvent resistance

After making the obtained colored coating film immersed in the N-methyl- 2-pyrrolidone of the large excess maintained constant at 23 degreeC for 40 minutes, it wash|cleaned sufficiently 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. Calculation method of color difference). The calculated value obtained was converted into the relative value (%) when ΔEab* of Comparative Example 1 was 100%. A result is shown in Table 2.

<Comparative Example 2>

(A) a colorant; C. I. Pigment Blue 15:6 (pigment) 29.5 parts

15 parts of acrylic pigment dispersant

198 parts of propylene glycol monomethyl ether acetate

to disperse the pigment sufficiently using a bead mill, and then,

(A) Dispersion (A1): 82 parts of Dispersion (1)

(B) resin; Resin (B-1) (in terms of solid content) 50 parts

(C) polymerizable compound; (C-1) ; Dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

(D) polymerization initiator; (D-1) ; 14 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (irgacure OXE 01; manufactured by BASF; oxime compound)

(F) leveling agent; (F-1) ; Polyether-modified silicone oil (Toray 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

was mixed to obtain a colored curable resin composition.

Moreover, according to the procedure described in said "(2) manufacture of a colored coating film", the colored coating film was created from the obtained colored curable resin composition. About the obtained colored coating film, chromaticity evaluation, heat resistance evaluation, and solvent resistance evaluation were implemented similarly to Examples 1-4 and Comparative Example 1. Each result is shown in Table 2.

ADVANTAGE OF THE INVENTION According to the colored curable resin composition of this invention, the color filter by which solvent resistance and heat resistance were improved can be manufactured.

Claims (6)

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,
The lake pigment is a compound (Aa) consisting of an anion of a compound containing at least one element and oxygen selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and a cation having a dye skeleton,
Said compound (Aa) is, Formula (AI):

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

[Y] ^m- represents at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and an m-valent anion containing oxygen.
m represents any natural number.
In the formula (AIX), R ⁴¹ to R ⁴⁴ are each independently a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alkyl group having 2 to 20 carbon atoms, and an oxygen atom between the methylene groups constituting the alkyl group is an inserted group (provided that a plurality of oxygen atoms are not inserted adjacently), a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent, an aralkyl group having 7 to 11 carbon atoms which may have a substituent, or represents a hydrogen atom.
R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may combine to form a ring together 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 hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, and when carbon number is 2 or more, an oxygen atom is inserted between the methylene groups constituting the alkyl group (However, a plurality of oxygen atoms are not inserted adjacently). R ⁴⁸ and R ⁵² may combine 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, a plurality of X ⁺ may have the same structure or different structures.]
is a compound represented by
The extender pigment (P) is at least one selected from the group consisting of zinc oxide, titanium oxide, silica and zirconia,
The colored curable resin composition which does not contain a silsesquioxane compound. A color filter formed from the colored curable resin composition according to claim 1 . A display device comprising the color filter according to claim 2 . delete delete delete