Colored curable resin composition, color filter and display device comprising the same

Abstract

The present invention provides a colored curable resin composition containing 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. The invention also provides a color filter and a display device.

Description

[0001] The present application is a divisional application of an application filed on March 29, 2017, with application number 201710200811.X, and entitled “Colored curable resin composition, color filter, and display device comprising the same.” Technical Field

[0002] The present invention relates to a colored curable resin composition, a color filter, and a display device including the same. Background Art

[0003] A colored curable composition is known that includes a colorant dispersion in which a colorant including a dye and a pigment, an extender pigment, and a dispersant are dispersed in a solvent containing propylene glycol monomethyl ether acetate, a polymerizable compound, and a polymerization initiator (Japanese Patent Application Publication No. 2015-98590). Summary of the Invention

[0004] The present invention provides the following colored curable resin composition, color filter, and display device.

[0005] [1] A colored curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and an extender pigment (P), and

[0006] The colorant (A) contains a lake pigment.

[0007] [2] The colored curable resin composition according to [1], wherein the lake pigment is a compound (Aa) comprising an anion and a cation, the anion being an anion of a compound containing oxygen and at least one element selected from tungsten, molybdenum, silicon, and phosphorus, and the cation having a pigment skeleton.

[0008] [3] The colored curable resin composition according to [2], wherein the compound (Aa) is a compound represented by formula (A-I),

[0009]

[0010] [In formula (A-I), X + This represents a cation represented by the formula (A-I-X).

[0011]

[0012] [Y] m- represents an m-valent anion containing oxygen and at least one element selected from tungsten, molybdenum, silicon, and phosphorus.

[0013] m represents an arbitrary natural number.

[0014] In the formula (A-I-X), R41 ~R 44 Each of them independently represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; an alkyl group having 2 to 20 carbon atoms in which an oxygen atom is inserted between methylene groups constituting the alkyl group (however, 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 a hydrogen atom.

[0015] R 41 With R 42 can be bonded to form a ring together with the nitrogen atom to which they are bonded, R 43 With R 44 They may bond to form a ring together with the nitrogen atom to which they are bonded.

[0016] R 47 ~R 54 Each independently represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or an alkyl group having 1 to 8 carbon atoms. When the number of carbon atoms is 2 or more, an oxygen atom may be inserted between the methylene groups constituting the alkyl group (however, multiple oxygen atoms may not be inserted adjacently). 48 With R 52 They can bond with each other to form -NH-, -O-, -S- or -SO2-.

[0017] T 1 represents a monovalent aromatic heterocyclic group which may have a substituent.

[0018] When m is a natural number greater than 2, multiple X + It can be the same structure or different structures. ].

[0019] [4] The colored curable resin composition according to any one of [1] to [3], wherein the extender pigment (P) is at least one selected from zinc oxide, titanium oxide, silicon dioxide, and zirconium oxide.

[0020] [5] A color filter formed from the colored curable resin composition according to any one of [1] to [4].

[0021] [6] A display device comprising the color filter described in [5]. DETAILED DESCRIPTION

[0022] <Colored curable resin composition>

[0023] 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), wherein the colorant (A) contains a lake pigment.

[0024] According to the colored curable resin composition of the present invention containing the colorant (A) and extender pigment (P), the solvent resistance and heat resistance of the cured film (such as a color filter) can be improved.

[0025] It should be noted that in this specification, unless otherwise specified, the compounds exemplified as each component can be used alone or in combination of multiple kinds.

[0026] 〔1〕Colorant (A)

[0027] 〔1-1〕Lake pigment

[0028] The colorant (A) contains lake pigments.

[0029] In this specification, the lake pigment refers to a pigment obtained by making a dye soluble in water or an organic solvent insoluble using a lake-forming agent. The solubility of this pigment in propylene glycol monomethyl ether acetate or propylene glycol monomethyl ether (23 °C) is 1% by mass or less, for example.

[0030] Examples of dyes that can form lake pigments include acid dyes, basic dyes, direct dyes, etc. Compounds classified as dyes having a hue other than pigments in The Society of Dyers and Colourists publication (Dye Index), and known dyes described in Dyeing Notes (in Japanese: 染色ノート) (Color Dyeing Society) can be used.

[0031] Specific examples of acid dyes 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; CI Acid Orange 7, 10, 11, 12, 15, 19, 20, 22, 28, 30, 52, 56, 74, 127; CI Acid Violet 9, 11, 15, 16, 17, 19, 21, 23, 24, 25, 30, 38, 41, 42, 43, 49, 50, 56, 58, 72; CI Acid Yellow 1 , 3, 17, 18, 23, 25, 36, 38, 42, 44, 54, 59, 72, 78, 151; CI 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, 9 0, 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; CI Acid Green 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 25, 27.

[0032] Specific examples of basic dyes 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; CI 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; CI Basic Brown 1, 16, 17, 1 8; 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; CI Basic Green 1, 4, 5.

[0033] Specific examples of direct dyes include CI Direct Blue 41, 77, 86, 87, 106, 107, 108, 109, 189, 190, 199, and 264; and CI Direct Violet 54.

[0034] Specific examples of the laking agent include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, cardanol, tamol, heteropoly acids (phosphotungstic acid, phosphomolybdic acid, phosphotungstomolybdic acid, silicotungstic acid, silicomolybdic acid, silicotungstomolybdic acid, etc.), and isopoly acids (tungstic acid, molybdic acid, etc.).

[0035] Specific examples of lake pigments include: 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; CI 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, 5 3, 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; CI Pigment Orange 17, 18, 19, 46; CI Pigment Yellow 18, 61, 61:1, 62, 100, 104, 115, 133, 168, 169, 183, 191, 209, 209:1, 212, etc.

[0036] The lake pigment in the present invention may have a cation derived from the dye or an anion derived from the dye. The lake pigment preferably has a cation derived from the dye.

[0037] Examples of the dye-derived cation include cations derived from triarylmethane dyes, rhodamine dyes, and xanthene dyes. The dye-derived cation is preferably a triarylmethane dye, more preferably a triarylmethane dye which may have a heterocyclic ring such as a thiazolyl group.

[0038] When the lake pigment has a cation derived from the dye, it generally has an anion containing a transition metal atom, a silicon atom, an aluminum atom, a boron atom, a sulfur atom, a halogen atom, or the like.

[0039] As anion in lake pigments, except for isopolyacid ions (M m1 O n ) c- 、Heteropoly acid ions(X l M m1 O n ) c-(In each formula, M represents a polyatom, X represents a heteroatom, l represents the composition ratio of the heteroatom, m1 represents the composition ratio of the polyatom, and n represents the composition ratio of oxygen atoms. c represents an integer of 1 to 8.) In addition, the following anions can be mentioned.

[0040]

[0041] (Wherein, M represents a boron atom or an aluminum atom. R 61 、R 62 、R 63 and R 64 Each independently represents a hydroxyl group, a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or a reactive group. 61 、R 62 、R 63 and R 64 At least one of them is a reactive group.

[0042]

[0043] [In formula (6), W 3 and W 4 Each independently represents a fluorine atom or a fluoroalkyl group having 1 to 4 carbon atoms, or W 3 With W 4 bonded to form a fluoroalkanediyl group having 1 to 4 carbon atoms.]

[0044]

[0045] [In formula (7), W 5 、W 6 and W 7 Each independently represents a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms.]

[0046]

[0047] [In formula (8), Y 1 represents a fluoroalkanediyl group having 1 to 4 carbon atoms.]

[0048]

[0049] [In formula (9), Y 2 represents a fluorinated alkyl group having 1 to 4 carbon atoms.]

[0050] From the viewpoints of solvent resistance and heat resistance, the lake pigment is preferably a compound (AA) comprising an anion of a compound containing oxygen and at least one element selected from tungsten (W), molybdenum (Mo), vanadium (V), titanium (Ti), niobium (Nb), silicon (Si), phosphorus (P), arsenic (As), sulfur (S), iron (Fe), and cobalt (Co), and a cation having a pigment skeleton. More preferably, it is a compound (Aa) comprising an anion of a compound containing oxygen and at least one element selected from W, Mo, Si, and P, and a cation having a pigment skeleton.

[0051] The lake pigment in the present invention is more preferably a lake pigment of a basic dye (triarylmethane dye, rhodamine dye, etc.) and a polyacid.

[0052] Polyacids are acids formed by the condensation of multiple oxygen-containing acids, which can be isopolyacid ions (M m1 O n ) c- , or heteropoly acid ions (X l M m1 O n ) c- In the formula, M represents a polyatom, X represents a heteroatom, l represents the composition ratio of the heteroatom, m1 represents the composition ratio of the polyatom, n represents the composition ratio of oxygen atoms, and c represents an integer of 1 to 8.

[0053] Examples of the polyatom M include W, Mo, V, Ti, and Nb.

[0054] Examples of the heteroatom X include Si, P, As, S, Fe, and Co.

[0055] Specific examples of polybasic acids preferred from the viewpoints of solvent resistance and heat resistance include tungstate ions [W 10 O 32 ] 4- 、Molybdate ion [Mo6O 19 ] 2- Equivalent polyacid; phosphotungstate ion [PW 12 O 40 ] 3- , silicotungstate ion [SiW 12 O 40 ] 4- 、Phosphombohedral ion [PMo 12 O 40 ] 3- 、phosphotungstomolybdate ion [PW 12－x Mo x O 40 ] 3- 、H3[PW 2－x Mo x O7] 4-More specifically, phosphotungstomolybdate ions [PW 10 Mo2O 40 ] 3- 、[PW 11 Mo1O 40 ] 3- , phosphotungstate ion [PW 12 O 40 ] 3- .

[0056] Among them, from the viewpoints of solvent resistance and heat resistance, the compound (Aa) is preferably a compound represented by formula (A-I).

[0057]

[0058] In formula (A-I), X + This represents a cation represented by the formula (A-I-X).

[0059]

[0060] [Y] m- represents an m-valent anion containing oxygen and at least one element selected from W, Mo, Si, and P. m represents an arbitrary natural number.

[0061] In the formula (A-I-X), R 41 ~R 44 Each of them independently represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; an alkyl group having 2 to 20 carbon atoms in which an oxygen atom is inserted between the methylene groups constituting the alkyl group (however, multiple 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 a hydrogen atom. 41 With R 42 can be bonded to form a ring together with the nitrogen atom to which they are bonded, R 43 With R 44 They may bond to form a ring together with the nitrogen atom to which they are bonded.

[0062] R 47 ~R 54 Each independently represents 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. When the alkyl group has 2 or more carbon atoms, an oxygen atom may be inserted between the methylene groups constituting the alkyl group (however, multiple oxygen atoms are not inserted adjacently).

[0063] R 48 With R 52 They can bond with each other to form -NH-, -O-, -S- or -SO2-.

[0064] T 1 represents a monovalent aromatic heterocyclic group which may have a substituent.

[0065] When m is a natural number greater than 2, multiple X + It can be the same structure or different structures.

[0066] As R 41 ~R 44 Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms include linear alkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl; branched alkyl groups having 3 to 20 carbon atoms, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl. Preferably, the linear or branched alkyl group has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, and even more preferably has 1 to 6 carbon atoms.

[0067] Examples of the substituent that the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms may have include a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a cyano group, a nitro group, a hydroxyl group, and a substituted or unsubstituted amino group.

[0068] About R 41 ~R 44 Examples of alkyl groups with 2 to 20 carbon atoms in which an oxygen atom is inserted between the methylene groups constituting the alkyl group include -CH2-O-CH3, -CH2-O-CH2-CH3, and -CH2-CH2-O-CH2-CH3. Examples of alkyl groups with 2 to 20 carbon atoms include linear alkyl groups with 2 to 20 carbon atoms, such as ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl; and branched alkyl groups with 3 to 20 carbon atoms, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl. Preferably, the alkyl group is a linear or branched alkyl group with 2 to 12 carbon atoms, more preferably a linear or branched alkyl group with 2 to 8 carbon atoms, and even more preferably a linear or branched alkyl group with 2 to 6 carbon atoms.

[0069] As R 41 ~R 44Examples of the monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms include phenyl, tolyl, xylyl, mesityl, propylphenyl, butylphenyl, and naphthyl. Examples of substituents that the monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms may have include a halogen atom (fluorine, chlorine, bromine, or iodine), a cyano group, a nitro group, a hydroxyl group, an alkoxy group, an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted amino group.

[0070] As R 41 ~R 44 Examples of the aralkyl group having 7 to 11 carbon atoms include benzyl, phenethyl, phenylpropyl, 2-methylphenylmethyl, 3-methylphenylmethyl, 4-methylphenylmethyl, 2,3-dimethylphenylmethyl, 2,4-dimethylphenylmethyl, 2,5-dimethylphenylmethyl, 2,6-dimethylphenylmethyl, 3,4-dimethylphenylmethyl, and naphthylmethyl.

[0071] 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.

[0072] As R 41 With R 42 can be bonded to form a ring together with the nitrogen atom to which they are bonded, R 43 With R 44 Examples of the ring that can be bonded to form together with the nitrogen atom to which they are bonded include a pyrrole ring, a pyrrolidine ring, a piperidine ring, an imidazole ring, an indole ring, a purine ring, an aziridine ring, a 1H-azirine ring, an azetidine ring, a hexamethyleneimine ring, an azatropilidene ring, an imidazoline ring, a morpholine ring, a thiazine ring, and a carbazole ring.

[0073] Among them, R 41 ~R 44 Preferred are independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

[0074] As R 47 ~R 54 Examples of the alkyl group having 1 to 8 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl. Preferred are alkyl groups having 1 to 6 carbon atoms, and more preferred are methyl, ethyl, propyl, and butyl.

[0075] About R 47 ~R 54The 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 in which an oxygen atom is inserted between the methylene groups constituting the alkyl group, and examples thereof include -CH2-O-CH3 group, -CH2-O-CH2-CH3 group, and -CH2-CH2-O-CH2-CH3 group.

[0076] Among them, R 47 ~R 54 Independently of each other, they are preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0077] About T 1 The aromatic heterocyclic ring constituting the monovalent aromatic heterocyclic group may be either monocyclic or polycyclic, and examples thereof include pyrrole, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, pyridine, pyrimidine, pyridazine, pyrazine, 1,2,3-triazine, quinoline, isoquinoline, quinazoline, indole, benzimidazole, benzofuran, purine, acridine, phenoxazine, and phenothiazine.

[0078] Examples of the substituent that the aromatic heterocyclic group may have include a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a cyano group, a nitro group, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted amino group.

[0079] [Y] m- represents an m-valent anion containing oxygen and at least one element selected from W, Mo, Si, and P. m represents an arbitrary natural number.

[0080] From the viewpoint of solvent resistance and heat resistance, the anion is preferably the above-mentioned polyacid, and preferred specific examples thereof are shown above. m is preferably a natural number of 1 to 10, more preferably a natural number of 1 to 6.

[0081] 〔1-2〕Dyes

[0082] The colorant (A) may further contain a dye other than the lake pigment.

[0083] Dyes that can be used are known dyes without particular limitation, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes having a hue other than pigments in the Dye Index (published by The Society of Dyers and Colourists), and known dyes described in Dyeing Notes (published by Sezensha). Examples of dyes that can be used include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, formaldehyde dyes, azomethine dyes, squaric acid dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes, based on their chemical structure. Among these, organic solvent-soluble dyes are preferred.

[0084] Specifically, CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189 can be mentioned;

[0085] CI 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;

[0086] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0087] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0088] 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;

[0089] CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35,

[0090] 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, 156 7, 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;

[0091] 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;

[0092] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0093] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0094] 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;

[0095] 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 and other CI acid dyes,

[0096] 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;

[0097] 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;

[0098] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0099] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0100] 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 7, 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;

[0101] CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI direct dyes,

[0102] CI Disperse Yellow 51, 54, 76;

[0103] CI Disperse Violet 26, 27;

[0104] CI disperse blue 1, 14, 56, 60 and other CI disperse dyes,

[0105] CI Basic Red 1, 10;

[0106] 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;

[0107] CI Basic Violet 2;

[0108] CI Basic Red 9;

[0109] CI basic dyes such as CI Basic Green 1,

[0110] CI Reactive Yellow 2, 76, 116;

[0111] CI Reactive Orange 16;

[0112] CI reactive dyes such as CI Reactive Red 36,

[0113] CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0114] CI Mordant 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;

[0115] CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0116] 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;

[0117] CI Mordant 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;

[0118] CI mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other CI mordant dyes,

[0119] CI vat dyes such as CI Vat Green 1, etc.

[0120] These dyes may be appropriately selected according to the spectral spectrum of the desired color filter.

[0121] Among these, when a dye is used, the dye preferably includes a xanthene dye from the viewpoints of solvent resistance, heat resistance, and the like, and from the viewpoint of obtaining good brightness.

[0122] Xanthene dyes are dyes containing compounds with a xanthene skeleton within the molecule. Examples of xanthene dyes include CI Acid Red 51, 52, 87, 92, 94, 289, and 388; CI Acid Violet 9, 30, and 102; CI Basic Red 1 (Rhodamine 6G), 2, 3, 4, and 8; CI Basic Red 10 and 11; CI Basic Violet 10 (Rhodamine B) and 11; CI Solvent Red 218; CI Mordant Red 27; CI Reactive Red 36 (Rhodamine B); sulforhodamine G; xanthene dyes described in Japanese Patent Application Laid-Open No. 2010-32999; and xanthene dyes described in Japanese Patent Application No. 4492760. Among these, dyes soluble in organic solvents are preferred.

[0123] Among these, the xanthene dye is preferably a dye containing a compound represented by formula (1a) (hereinafter sometimes referred to as “compound (1a)”).

[0124] Compound (1a) may be a tautomer thereof. When a xanthene dye is further included as the colorant (A), the content of compound (1a) in the xanthene dye is preferably 50% by mass or greater, more preferably 70% by mass or greater, and even more preferably 90% by mass or greater. It is preferred to use only compound (1a) as the xanthene dye.

[0125]

[0126] In formula (1a), R 1 ~R 4 Each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a monovalent aralkyl group having 7 to 20 carbon atoms which may have a substituent, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, wherein the -CH2- group contained in the saturated hydrocarbon group and the aralkyl group may be replaced by -O-, -CO- or -NR 11 - Replacement. R 1 and R 2 can form a ring containing nitrogen atoms, R 3 and R 4 Together they may form a ring containing a nitrogen atom.

[0127] R 5 Indicates -OH, -SO3 - 、-SO3H、-SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 、-SO3R 8 or -SO2NR 9 R 10 .

[0128] R 6 and R 7 Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0129] m represents an integer from 0 to 5. When m is 2 or more, a plurality of R 5 Can be the same or different.

[0130] a represents an integer of 0 or 1.

[0131] X represents a halogen atom.

[0132] Z + express + N (R 11 4. Na + or K + , 4 R 11 Can be the same or different.

[0133] R 8 It represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, wherein hydrogen atoms contained in the saturated hydrocarbon group may be substituted with halogen atoms.

[0134] R 9 and R 10 Each independently represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- contained in the saturated aliphatic hydrocarbon group may be replaced by -O-, -CO-, -NH- or -NR 8 - Replacement, R 9 and R 10 They may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.

[0135] 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), there is -SO3 － In the case of － The quantity is 1.

[0136] As R 1 ~R 4 Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl, tolyl, xylyl, mesityl, propylphenyl, and butylphenyl.

[0137] 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 which may be substituted with a halogen atom, -OH, -OR 8 , -SO3 - 、-SO3H、-SO3 - Z + , -CO2H, -CO2R8 , -SR 8 , -SO2R 8 、-SO3R 8 or -SO2NR 9 R 10 Among them, as a substituent, -SO3 is preferred. - 、-SO3H、-SO3 - Z + and -SO2NR 9 R 10 , more preferably -SO3 - Z + and -SO2NR 9 R 10 As the -SO3 - Z + , preferably -SO3 - + N (R 11 ) 4. If R 1 ~R 4 When the compound (1a) is one of these groups, a color filter having less generation of foreign matter and better solvent resistance and heat resistance can be formed from the colored curable resin composition of the present invention containing the compound (1a).

[0138] As R 1 ~R 4 and R 8 ~R 11 The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in the group may include, for example, straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl; branched-chain alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl.

[0139] R 1 ~R 4 The hydrogen atoms contained in the saturated hydrocarbon group may be substituted with, for example, halogen atoms.

[0140] As R 1 ~R 4 The aralkyl group shown in R 41 ~R 44 The same examples as those shown are for the aralkyl groups.

[0141] R 9 and R 10 The hydrogen atoms contained in the saturated hydrocarbon group may be substituted with, for example, a hydroxyl group or a halogen atom.

[0142] As R 1 and R2 The ring formed together, and R 3 and R 4 Examples of the ring formed together include the following rings.

[0143]

[0144] AS-OR 8 , methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, eicosyloxy and the like can be mentioned.

[0145] As-CO2R 8 , methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexyloxycarbonyl and eicosyloxycarbonyl can be mentioned.

[0146] As a -SR 8 , methylthio, ethylthio, butylthio, hexylthio, decylthio and eicosylthio can be mentioned.

[0147] As-SO2R 8 , methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl and eicosylsulfonyl groups and the like are exemplified.

[0148] AS-SO3R 8 , methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert-butoxysulfonyl, hexyloxysulfonyl and eicosylsulfonyl groups can be mentioned.

[0149] As -SO2NR 9 R 10 , which can be listed as follows:

[0150] sulfamoyl;

[0151] N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N-(1-ethylpropyl)sulfamoyl, N-(1,1-dimethylpropyl)sulfamoyl, N-(1,2-dimethylpropyl)sulfamoyl, N-(2,2-dimethylpropyl)sulfamoyl, N-(1-methylbutyl)sulfamoyl, N-(2-methylbutyl)sulfamoyl, N N-1-substituted sulfamoyl groups such as N-(3-methylbutyl)sulfamoyl, N-cyclopentylsulfamoyl, N-hexylsulfamoyl, N-(1,3-dimethylbutyl)sulfamoyl, N-(3,3-dimethylbutyl)sulfamoyl, N-heptylsulfamoyl, N-(1-methylhexyl)sulfamoyl, N-(1,4-dimethylpentyl)sulfamoyl, N-octylsulfamoyl, N-(2-ethylhexyl)sulfamoyl, N-(1,5-dimethyl)hexylsulfamoyl, and N-(1,1,2,2-tetramethylbutyl)sulfamoyl;

[0152] N,N-2 substituted sulfamoyl groups such as N,N-dimethylsulfamoyl, N,N-methylethylsulfamoyl, N,N-diethylsulfamoyl, N,N-methylpropylsulfamoyl, N,N-methylisopropylsulfamoyl, N,N-methyl-tert-butylsulfamoyl, N,N-ethylbutylsulfamoyl, N,N-bis(1-methylpropyl)sulfamoyl, and N,N-methylheptylsulfamoyl.

[0153] R 5 Preferably -CO2H, -CO2 - Z + , -CO2R 8 , -SO3 - , -SO3 - Z + , -SO3H or SO2NHR 9 , more preferably SO3 - , -SO3 - Z + , -SO3H or SO2NHR 9 .

[0154] m is preferably 1 to 4, more preferably 1 or 2.

[0155] As R 6 and R 7 Examples of the alkyl group having 1 to 6 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, and hexyl; and branched alkyl groups such as isopropyl, isobutyl, isopentyl, and neopentyl.

[0156] As R 11Examples of the aralkyl group having 7 to 10 carbon atoms include benzyl, phenylethyl, and phenylbutyl.

[0157] Z + for + N (R 11 4. Na + or K + , preferably + N (R 11 )4.

[0158] As the above + N (R 11 ) 4, preferably 4 R 11 At least two of them are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. 11 The total number of carbon atoms is preferably 20 to 80, more preferably 20 to 60. When the compound (1a) contains + N (R 11 ) 4, if R 11 When the compound (1a) is one of these groups, a color filter with less foreign matter can be formed from the colored curable resin composition of the present invention containing the compound (1a).

[0159] As compound (1a), a compound represented by formula (2a) (hereinafter sometimes referred to as "compound (2a)") is preferred. Compound (2a) may be a tautomer thereof.

[0160]

[0161] In formula (2a), R 21 ~R 24 R independently represents 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. 21 and R 22 can form a ring containing nitrogen atoms, R 23 and R 24 Together they may form a ring containing a nitrogen atom.

[0162] R 25 Indicates -SO3 - 、-SO3H、-SO3 - Z1 + or -SO2NHR 26 .

[0163] m1 represents an integer from 0 to 5. When m1 is 2 or more, a plurality of R 25 Can be the same or different.

[0164] a1 represents an integer of 0 or 1.

[0165] X1 represents a halogen atom.

[0166] R 26 It represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.

[0167] Z1 + express + N (R 27 4. Na + or K + , 4 R 27 Can be the same or different.

[0168] R 27 It represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group.

[0169] In formula (2a), as R 21 ~R 24 The monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in the present invention includes the following: 1 ~R 4 The same groups as those exemplified for the aromatic hydrocarbon group are included.

[0170] The hydrogen atoms contained in the aromatic hydrocarbon group can be replaced by -SO3 - 、-SO3H、-SO3 - Z1 + 、-SO3R 26 or -SO2NHR 26 replace.

[0171] In formula (2a), R 21 and R 23 is a hydrogen atom, R 22 and R 24 A monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, wherein the hydrogen atoms contained in the aromatic hydrocarbon group are replaced by -SO3 - 、-SO3H、-SO3 - Z1 + 、-SO3R 26 or -SO2NHR 26 replace,

[0172] More preferably R 21 and R 23 is a hydrogen atom, R 22 and R 24 A monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, wherein the hydrogen atoms contained in the aromatic hydrocarbon group are replaced by -SO3 - Z1 + or -SO2NHR 26 replace.

[0173] If R 21 ~R 24When the compound (2a) is one of these groups, a color filter having further excellent solvent resistance and heat resistance can be formed from the colored curable resin composition of the present invention containing the compound (2a).

[0174] As R 21 and R 22 Together, they form a ring containing a nitrogen atom, and R 23 and R 24 The ring containing nitrogen atoms formed together with R 1 and R 2 The ring formed together is the same ring. Among them, an aliphatic heterocycle is preferred. Examples of the aliphatic heterocycle include the following rings.

[0175]

[0176] As R 21 ~R 24 、R 26 and R 27 The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 8 ~R 11 The same groups as those exemplified as the saturated hydrocarbon groups are included.

[0177] R 21 ~R 24 The saturated hydrocarbon groups shown are each independently preferably a methyl group or an ethyl group.

[0178] AS-SO3R 26 and SO2NHR 26 R in 26 , preferably a branched alkyl group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 6 to 12 carbon atoms, and further preferably a 2-ethylhexyl group. 26 When the compound (2a) is one of these groups, a color filter having excellent solvent resistance and heat resistance can be formed from the colored curable resin composition of the present invention containing the compound (2a).

[0179] Z1 + for + N (R 27 4. Na + or K + , preferably + N (R 27 )4.

[0180] As the above + N (R 27 ) 4, preferably 4 R 27 At least two of them are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. 27 The total carbon number of is preferably 20 to 80, more preferably 20 to 60. When the compound (2a) is present+ N (R 27 ) 4, if R 27 When the compound (2a) is one of these groups, a color filter having excellent solvent resistance and heat resistance can be formed from the colored curable resin composition of the present invention containing the compound (2a).

[0181] m1 is preferably 1 to 4, more preferably 1 or 2.

[0182] As compound (1a), a compound represented by formula (3a) (hereinafter sometimes referred to as "compound (3a)") is also preferred. Compound (3a) may be a tautomer thereof.

[0183]

[0184] In formula (3a), R 31 and R 32 Each independently represents a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, wherein the hydrogen atoms contained in the saturated hydrocarbon group and the aralkyl group may be substituted by a halogen atom, the hydrogen atoms contained in the aromatic hydrocarbon group of the aralkyl group may be substituted by an alkoxy group having 1 to 3 carbon atoms, and the -CH2- contained in the above-mentioned saturated hydrocarbon group and the aralkyl group may be replaced by -O-, -CO- or -NR 11 - Replacement.

[0185] R 33 and R 34 Each independently represents an alkyl group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkylsulfonyl group having 1 to 4 carbon atoms.

[0186] R 31 and R 33 can form a ring containing nitrogen atoms, R 32 and R 34 Together they may form a ring containing a nitrogen atom.

[0187] p and q each independently represent an integer of 0 to 5. When p is 2 or greater, a plurality of R 33 They may be the same or different. When q is 2 or more, multiple R 34 Can be the same or different.

[0188] R 11 Means the same as above.

[0189] As R 31 and R 32The monovalent saturated hydrocarbon group having 1 to 10 carbon atoms in the group includes linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; and alicyclic saturated hydrocarbon groups having 3 to 10 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

[0190] As R 31 and R 32 The above-mentioned aralkyl group includes phenylene and the like.

[0191] Examples of the alkoxy group having 1 to 3 carbon atoms include a methoxy group, an ethoxy group, and a propoxy group.

[0192] R 31 and R 32 Each of them is preferably independently a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 3 carbon atoms.

[0193] As R 33 and R 34 Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.

[0194] As R 33 and R 34 Examples of the alkylthio group having 1 to 4 carbon atoms include methylthio, ethylthio, propylthio, butylthio and isopropylthio.

[0195] As R 33 and R 34 Examples of the alkylsulfonyl group having 1 to 4 carbon atoms include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and isopropylsulfonyl.

[0196] R 33 and R 34 An alkyl group having 1 to 4 carbon atoms is preferred, and a methyl group is more preferred.

[0197] p and q are preferably integers of 0 to 2, and more preferably 0 or 1.

[0198] Examples of compound (1a) include compounds represented by formula (1-1) to formula (1-43). 40 It represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, and more preferably a 2-ethylhexyl group.

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] Among the above compounds, the compounds represented by formula (1-1) to formula (1-23) or formula (1-37) to formula (1-43) correspond to compound (2a), and the compound represented by any one of formula (1-24) to formula (1-36) corresponds to compound (3a).

[0208] Among them, preferred are sulfonamides of CI Acid Red 289, quaternary ammonium salts of CI Acid Red 289, sulfonamides of CI Acid Violet 102, and quaternary ammonium salts of CI Acid Violet 102. Examples of such compounds include compounds represented by Formula (1-1) to Formula (1-8), Formula (1-11), and Formula (1-12).

[0209] In addition, a compound represented by any one of Formulae (1-24) to (1-33) is also preferred because of its excellent solubility in organic solvents.

[0210] As the xanthene dye, a commercially available xanthene dye (e.g., "Chugai Aminol FastPink R-H / C" manufactured by Chugai Chemical Co., Ltd., or "Rhodamin 6G" manufactured by Taoka Chemical Industry Co., Ltd.) can be used. Alternatively, a commercially available xanthene dye can be synthesized using a starting material with reference to Japanese Patent Application Laid-Open No. 2010-32999.

[0211] 〔1-3〕Coloring pigments

[0212] The colorant (A) may further contain a coloring pigment other than a lake pigment (but different from a lake pigment). The coloring pigment is not particularly limited, and known coloring pigments can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be mentioned.

[0213] Examples of coloring pigments include:

[0214] 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 and other yellow pigments;

[0215] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;

[0216] 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 and other red pigments;

[0217] CI Pigment Blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments;

[0218] CI Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments;

[0219] Green pigments such as CI Pigment Green 7, 36, 58;

[0220] Brown pigments such as CI Pigment Brown 23 and 25;

[0221] Black pigments such as CI Pigment Black 1, 7, etc.; etc.

[0222] Preferred coloring pigments include blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, and 60, and violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, and 38. More preferred are CI Pigment Blue 15:3, 15:6, and CI Pigment Violet 23, and even more preferred is CI Pigment Blue 15:6. The inclusion of these coloring pigments facilitates optimization of the transmission spectrum, improving the light resistance and solvent resistance of the color filter.

[0223] If necessary, the coloring pigment may be subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, grafting treatment on the pigment surface using a polymer compound, micronization treatment using a sulfuric acid micronization method, or washing treatment using an organic solvent or water for removing impurities, or removal treatment for removing ionic impurities using an ion exchange method.

[0224] The coloring pigment preferably has a uniform particle size. By containing a pigment dispersant and performing a dispersion treatment, a pigment dispersion in which the coloring pigment is uniformly dispersed in a solution can be obtained.

[0225] Examples of the pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of pigment dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (manufactured by Zeneca Corporation), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine Chemicals Co., Ltd.), and Disperbyk (manufactured by BYK Chemical Co., Ltd.).

[0226] When a pigment dispersant is used, its usage amount is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less, relative to the total amount of the coloring pigment. If the usage amount of the pigment dispersant is within the above range, there is a tendency to obtain a pigment dispersion liquid in a uniformly dispersed state.

[0227] 〔1-4〕Content ratio of colorant (A)

[0228] The content of the colorant (A) is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and even more preferably 10 to 50% by mass, relative to the total solids content of the colored curable resin composition. When the content of the colorant (A) is within this range, the color filter produced has sufficient color density, and the composition can contain the desired amounts of the resin (B) and the polymerizable compound (C), thereby enabling the formation of a pattern with sufficient mechanical strength.

[0229] As used herein, the term "total solids content" refers to the total amount of the colored curable resin composition excluding the solvent content. The total solids content and the percentage of each component relative to the total solids content can be measured using known analytical methods such as liquid chromatography or gas chromatography.

[0230] From the viewpoint of solvent resistance and heat resistance, the content of the lake pigment in the colorant (A) is preferably 2.5 to 100 mass %, more preferably 45 to 100 mass %, further preferably 75 to 100 mass %, and particularly preferably 90 to 100 mass %, based on 100 mass % of the colorant (A).

[0231] When the colorant (A) contains a dye, the content of the dye in the colorant (A) is generally 0.1 to 98 mass %, preferably 0.1 to 60 mass %, more preferably 0.1 to 50 mass %, further preferably 0.5 to 25 mass %, and particularly preferably 0.5 to 10 mass % based on 100 mass % of the colorant (A), from the viewpoint of solvent resistance and heat resistance.

[0232] When the colorant (A) contains a color pigment, the content of the color pigment in the colorant (A) is generally 0.1 to 98 mass %, preferably 0.1 to 60 mass %, more preferably 0.1 to 50 mass %, further preferably 5 to 25 mass %, and particularly preferably 0.5 to 10 mass % based on 100 mass % of the colorant (A), from the viewpoint of solvent resistance and heat resistance.

[0233] 〔2〕Resin (B)

[0234] The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

[0235] Resin [K4.8 / 128 1]: A copolymer of at least one (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"), and a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");

[0236] Resin [K2]: a copolymer of (a) and (b) and a monomer (c) copolymerizable with (a) (but different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0237] Resin [K3]: copolymer of (a) and (c);

[0238] Resin [K4]: a resin obtained by reacting a copolymer of (a) and (c) with (b);

[0239] Resin [K5]: a resin obtained by reacting a copolymer of (b) and (c) with (a);

[0240] Resin [K6]: A resin obtained by reacting a copolymer of (b) and (c) with (a), and then reacting the reacted copolymer with a carboxylic anhydride.

[0241] Examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid;

[0242] Unsaturated dicarboxylic acids such as 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, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid;

[0243] Bicyclic unsaturated compounds containing a carboxyl group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]-2-heptene, 5,6-dicarboxybicyclo[2.2.1]-2-heptene, 5-carboxy-5-methylbicyclo[2.2.1]-2-heptene, 5-carboxy-5-ethylbicyclo[2.2.1]-2-heptene, 5-carboxy-6-methylbicyclo[2.2.1]-2-heptene, and 5-carboxy-6-ethylbicyclo[2.2.1]-2-heptene;

[0244] Unsaturated dicarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]-2-heptenoic anhydride;

[0245] Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate;

[0246] Unsaturated acrylic acid esters containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid; etc.

[0247] Among them, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution.

[0248] (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) Preferably, the monomer has a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0249] In this specification, “(meth)acrylic acid” refers to at least one selected from acrylic acid and methacrylic acid. The same applies to “(meth)acryloyl” and “(meth)acrylate”.

[0250] Examples of (b) include a monomer (b1) having an ethylene oxide group and an ethylenically unsaturated bond [hereinafter sometimes referred to as "(b1)"]. A monomer (b2) having an oxetane group and an ethylenically unsaturated bond [hereinafter sometimes referred to as "(b2)"]. A monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond [hereinafter sometimes referred to as "(b3)"].

[0251] Examples of (b1) include monomers (b1-1) having a structure obtained by epoxidizing a linear or branched aliphatic unsaturated hydrocarbon (hereinafter sometimes referred to as “(b1-1)”) and monomers (b1-2) having a structure obtained by epoxidizing an alicyclic unsaturated hydrocarbon (hereinafter sometimes referred to as “(b1-2)”).

[0252] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl 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-vinylbenzyl glycidyl ether, 2,3-bis( styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

[0253] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (I), and compounds represented by formula (II).

[0254]

[0255] [In formula (I) and formula (II), R a and R b It represents 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 by a hydroxy group.

[0256] X a and Xb Represents a single bond, -R c - -R c -O-, -R c -S- or -R c -NH-.

[0257] R c It represents an alkanediyl group having 1 to 6 carbon atoms.

[0258] Indicates a bond with O.]

[0259] Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.

[0260] Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

[0261] As R a and R b , preferably, a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are mentioned, and more preferably, a hydrogen atom and a methyl group are mentioned.

[0262] Examples of the alkanediyl group include methylene, ethylene, 1,2-propylenediyl (propane-1,2-diyl), 1,3-propylenediyl (propane-1,3-diyl), 1,4-butanediyl (butane-1,4-diyl), 1,5-pentanediyl (pentane-1,5-diyl), and 1,6-hexanediyl (hexane-1,6-diyl).

[0263] As X a and X b , preferably a single bond, methylene, ethylene, -CH2-O- and -CH2CH2-O-, more preferably a single bond, -CH2CH2-O-( represents a bond with O).

[0264] Examples of the compound represented by formula (I) include compounds represented by any one of formulas (I-1) to (I-15). Among them, compounds represented by formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9), or formulas (I-11) to (I-15) are preferred, and compounds represented by formula (I-1), formula (I-7), formula (I-9), or formula (I-15) are more preferred.

[0265]

[0266]

[0267] Examples of the compound represented by formula (II) include compounds represented by any one of formulas (II-1) to (II-15). Among them, compounds represented by formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9), or formulas (II-11) to (II-15) are preferred, and compounds represented by formula (II-1), formula (II-7), formula (II-9), or formula (II-15) are more preferred.

[0268]

[0269]

[0270] The compound represented by formula (I) and the compound represented by formula (II) may be used alone or in combination of two or more. When the compound represented by formula (I) and the compound represented by formula (II) are used in combination, the content ratio [compound represented by formula (I):compound represented by formula (II)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20, on a molar basis.

[0271] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 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-methacryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane.

[0272] As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0273] As (b), (b1) is preferred in that the reliability of the obtained color filter, such as heat resistance and chemical resistance, can be further improved. Furthermore, (b1-2) is more preferred in that the storage stability of the colored curable resin composition is excellent.

[0274] Examples of (c) include 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](meth)acrylate. 2,6 ] decyl-8-acrylate [In this technical field, it is commonly called "dicyclopentyl (meth)acrylate". It is also sometimes called "tricyclodecyl (meth)acrylate". ], tricyclo[5.2.1.0 2,6 (Meth)acrylates such as decen-8-yl acrylate (commonly known in the art as "dicyclopentenyl (meth)acrylate"), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0275] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0276] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0277] Bicyclo[2.2.1]-2-heptene, 5-methylbicyclo[2.2.1]-2-heptene, 5-ethylbicyclo[2.2.1]-2-heptene, 5-hydroxybicyclo[2.2.1]-2-heptene, 5-hydroxymethylbicyclo[2.2.1]-2-heptene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]-2-heptene, 5-methoxybicyclo[2.2.1]-2-heptene, 5-ethoxybicyclo[2.2.1]-2-heptene, 5,6-dihydroxybicyclo[2.2.1]-2-heptene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]-2-heptene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]-2-heptene, 5,6-dimethoxybicyclo[2.2.1]-2-heptene Bicyclic unsaturated compounds such as cyclo[2.2.1]-2-heptene, 5,6-diethoxybicyclo[2.2.1]-2-heptene, 5-hydroxy-5-methylbicyclo[2.2.1]-2-heptene, 5-hydroxy-5-ethylbicyclo[2.2.1]-2-heptene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]-2-heptene, 5-tert-butoxycarbonylbicyclo[2.2.1]-2-heptene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]-2-heptene, 5-phenoxycarbonylbicyclo[2.2.1]-2-heptene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]-2-heptene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]-2-heptene;

[0278] Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;

[0279] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene; etc.

[0280] Among them, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]-2-heptene, and the like are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0281] In the resin [K1], the ratio of the structural units derived from each component in all the structural units constituting the resin [K1] is preferably in the following range:

[0282] Structural units derived from (a): 2 to 60 mol%

[0283] Structural units derived from (b): 40 to 98 mol %.

[0284] More preferably, the following range:

[0285] Structural units derived from (a): 10 to 50 mol%

[0286] Structural units derived from (b): 50 to 90 mol %.

[0287] When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be excellent.

[0288] Resin [K1] can be produced by referring to the method described in, for example, "Experimental Methods for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd., Chemical Dojin, 1st edition, 1st printing, published on March 1, 1972) and the cited documents described therein.

[0289] Specifically, the following method can be used: prescribed amounts of (a) and (b), a polymerization initiator, and a solvent are added to a reaction vessel, oxygen is replaced with nitrogen, for example, to create a deoxygenated atmosphere, and the mixture is heated and maintained while stirring. It should be noted that the polymerization initiator and solvent used herein are not particularly limited, and those commonly used in this field can be used. For example, polymerization initiators include azo compounds (such as 2,2'-azobisisobutyronitrile and 2,2'-azobis(2,4-dimethylvaleronitrile)) and organic peroxides (such as benzoyl peroxide). As for the solvent (E) of the colored curable resin composition of the present invention, any solvent that dissolves the monomers can be used, and the solvents described below can be used.

[0290] The resulting copolymer may be used directly as the post-reaction solution, after concentration or dilution, or after extraction as a 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 the solvent for polymerization, the post-reaction solution can be used directly to prepare the colored curable resin composition of the present invention, thereby simplifying the production process of the colored curable resin composition of the present invention.

[0291] In the resin [K2], the ratio of the structural units derived from each component in all the structural units constituting the resin [K2] is preferably in the following range:

[0292] Structural units derived from (a): 2 to 45 mol%

[0293] Structural units derived from (b): 2 to 95 mol%

[0294] Structural unit derived from (c): 1 to 65 mol %.

[0295] More preferably, the following range:

[0296] Structural units derived from (a): 5 to 40 mol%

[0297] Structural units derived from (b): 5 to 80 mol%

[0298] Structural units derived from (c): 5 to 60 mol %.

[0299] 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 when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be excellent.

[0300] The resin [K2] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0301] In the resin [K3], the ratio of the structural units derived from each component in all the structural units constituting the resin [K3] is preferably in the following range:

[0302] Structural units derived from (a): 2 to 60 mol%

[0303] Structural units derived from (c): 40 to 98 mol %.

[0304] More preferably, the following range:

[0305] Structural units derived from (a): 10 to 50 mol%

[0306] Structural units derived from (c): 50 to 90 mol %.

[0307] The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0308] Resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding the C 2-4 cyclic ether contained in (b) to the carboxylic acid and / or carboxylic anhydride contained in (a).

[0309] First, a copolymer of (a) and (c) is produced in the same manner as described as the method for producing resin [K1]. In this case, the ratio of the structural units derived from each component is preferably the same as the ratio listed for resin [K3].

[0310] Next, the C 2-4 cyclic ether contained in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer.

[0311] Immediately after the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, (b), a reaction catalyst (such as tris(dimethylaminomethyl)phenol) for a carboxylic acid or a carboxylic anhydride and a cyclic ether), and a polymerization inhibitor (such as hydroquinone) are added to the flask, and the mixture is reacted at, for example, 60 to 130° C. for 1 to 10 hours to produce a resin [K4].

[0312] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). This range tends to provide a good balance between the storage stability of the colored curable resin composition, the developability during pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Because cyclic ethers have high reactivity and are less likely to leave unreacted (b), (b1) is preferred as the (b) used in resin [K4], and (b1-1) is more preferred.

[0313] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (c).

[0314] The reaction conditions such as the feeding method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the heat generated by polymerization, etc. It should be noted that, like the polymerization conditions, the feeding method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the heat generated by polymerization, etc.

[0315] For resin [K5], as a first step, a copolymer of (b) and (c) is obtained in the same manner as for the production of resin [K1]. As described above, the resulting copolymer may be used directly as the solution after the reaction, or after a concentrated or diluted solution, or after being extracted as a solid (powder) by methods such as reprecipitation.

[0316] The ratios of the structural units derived from (b) and (c) relative to the total number of moles of all structural units constituting the copolymer are preferably in the following ranges:

[0317] Structural units derived from (b): 5 to 95 mol%

[0318] Structural units derived from (c): 5 to 95 mol %.

[0319] More preferably, the following range:

[0320] Structural units derived from (b): 10 to 90 mol%

[0321] Structural units derived from (c): 10 to 90 mol %.

[0322] Furthermore, resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a) under the same conditions as those in the method for producing resin [K4].

[0323] The amount of (a) reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). (b) used in the resin [K5] is preferably (b1), and more preferably (b1-1), because the cyclic ether has high reactivity and is less likely to leave unreacted (b).

[0324] The resin [K6] is obtained by further reacting the resin [K5] with a carboxylic anhydride.

[0325] The hydroxyl group produced by the reaction of the cyclic ether and the carboxylic acid or the carboxylic anhydride is reacted with the carboxylic anhydride.

[0326] Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]-2-heptenoic anhydride. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mol per 1 mol of the amount of (a) used.

[0327] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6 ] decyl ester / (meth) acrylic acid copolymer resins [K1]; (meth) acrylate glycidyl / (meth) acrylate benzyl / (meth) acrylic acid copolymer, (meth) acrylate glycidyl / styrene / (meth) acrylic acid copolymer, acrylic acid-3,4-epoxy tricyclic [5.2.1.0 2.6]decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; resins in which glycidyl (meth)acrylate is added to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to tricyclodecyl (meth)acrylate / (meth)acrylic acid copolymer, [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate, and resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate, and resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate and styrene, and glycidyl (meth)acrylate, and resins obtained by further reacting the obtained resin with tetrahydrophthalic anhydride, and resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate, and resins obtained by further reacting the obtained resin with tetrahydrophthalic anhydride, and the like [K6]. Among these, resin (B) is preferably resin [K1] or resin [K2].

[0328] The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within this range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

[0329] The dispersion degree of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0330] The acid value of resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g. The acid value is measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B) and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0331] The content of resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and even more preferably 17 to 55% by mass, relative to the total solids content of the colored curable resin composition. When the content of resin (B) is within this range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0332] [3] Polymerizable compound (C)

[0333] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated by the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylate compounds.

[0334] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol 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, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0335] Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferred.

[0336] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

[0337] The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and even more preferably 17 to 55% by mass, relative to the total solids content of the colored curable resin composition. When the content of the polymerizable compound (C) is within this range, the residual film rate during colored pattern formation and the solvent resistance of the color filter tend to improve.

[0338] 〔4〕Polymerization initiator (D)

[0339] The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and a known polymerization initiator can be used.

[0340] Examples of the polymerization initiator that generates active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0341] The above-mentioned O-acyl oxime compound is a compound having a structure represented by formula (d1). Indicates a bond.

[0342]

[0343] Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, and N-acetoxy-1-[9

[0015] Examples of the present invention include N-acetyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine. Commercially available products such as Irgacure OXE01, OXE02, and OXE03 (all manufactured by BASF) and N-1919 (manufactured by ADEKA) can also be used. Among these, the O-acyl oxime compound is preferably at least one selected from N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, with N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine being more preferred. These O-acyl oxime compounds tend to produce a high-brightness color filter.

[0344] The alkylphenone compound is a compound having a structure represented by formula (d2) or a structure represented by formula (d3). In these structures, the benzene ring may have a substituent.

[0345]

[0346] Examples of the compound having the structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

[0347] Examples of the compound having a structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0348] In terms of sensitivity, the alkylphenone compound is preferably a compound having a structure represented by formula (d2).

[0349] 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-methoxyphenyl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2- (5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0350] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

[0351] 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 JP-A-6-75372 and JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole. (Alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (see Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.), imidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with alkoxycarbonyl groups (see Japanese Patent Application Laid-Open No. 7-10913, etc.), and the like.

[0352] Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These polymerization initiators are preferably used in combination with the polymerization initiation aid (D1) described below (particularly an amine compound).

[0353] Examples of the acid generator include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl toluenesulfonate, and benzoin toluenesulfonate.

[0354] The polymerization initiator (D) is preferably a polymerization initiator containing at least one compound selected from alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and bisimidazole compounds, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0355] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within this range, the exposure time tends to be shortened due to increased sensitivity, thereby improving the productivity of the color filter.

[0356] 〔5〕Polymerization initiator (D1)

[0357] The colored curable resin composition of the present invention may contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to accelerate the polymerization of a polymerizable compound that is polymerized by a polymerization initiator. When the polymerization initiator (D1) is included, it is typically used in combination with a polymerization initiator (D). Examples of the polymerization initiator (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0358] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Among them, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

[0359] 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, and 2-ethyl-9,10-dibutoxyanthracene.

[0360] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0361] Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthyloxyacetic acid.

[0362] When using these polymerization initiator aids (D1), the content thereof is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiator aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and there is a tendency to improve the productivity of the color filter.

[0363] 〔6〕Extender pigment (P)

[0364] The colored curable resin composition of the present invention contains an extender pigment (P). The colored curable resin composition of the present invention containing the colorant (A) and the extender pigment (P) can improve the solvent resistance and heat resistance of the cured film (color filter, etc.).

[0365] As the extender pigment (P), known extenders can be used without particular limitation, and examples thereof include zinc oxide (ZnO), titanium oxide (TiO2), silicon dioxide (SiO2), zirconium oxide (ZrO2), barium carbonate (BaCO3), lime carbonate (CaCO3), basic magnesium carbonate (MgCO3), aluminum hydroxide (Al(OH)3), kaolin clay, and nepheline syenite.

[0366] From the perspectives of solvent resistance and heat resistance, the extender pigment (P) is preferably at least one selected from zinc oxide, titanium oxide, silicon dioxide, zirconium oxide, barium carbonate, lime carbonate, and basic magnesium carbonate, and more preferably at least one selected from zinc oxide, titanium oxide, silicon dioxide, and zirconium oxide. Furthermore, from the perspective of obtaining a composition capable of producing a color filter with high brightness, an extender pigment with high transparency is preferred. For high transparency, the primary particle size of the extender pigment (P) is preferably 0.1 μm or less, and more preferably 0.05 μm or less. The primary particle size of the extender pigment (P) is typically 0.01 μm or greater.

[0367] The content of the extender pigment (P) is preferably 0.5 to 10% by mass, more preferably 1 to 7% by mass, and even more preferably 1.5 to 5% by mass, relative to the total solids content of the colored curable resin composition. A content of the extender pigment (P) within this range is advantageous in improving solvent resistance and heat resistance.

[0368] 〔7〕Solvent (E)

[0369] The colored curable resin composition of the present invention may contain a solvent (E). The solvent (E) is not particularly limited, and any solvent commonly used in the art can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- and no -O- in the molecule), ether solvents (solvents containing -O- and no -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and no -COO- in the molecule), alcohol solvents (solvents containing OH and no -O-, -CO-, or -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0370] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0371] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, 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, phenethyl ether, and methyl anisole.

[0372] Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0373] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0374] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0375] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0376] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0377] Among the above solvents, organic solvents having a boiling point of 120°C to 180°C at 1 atm are preferred from the perspectives of coating and drying properties. Preferred solvents include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, with propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and ethyl 3-ethoxypropionate being more preferred.

[0378] The content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, relative to the total amount of the colored curable resin composition of the present invention. In other words, the total solid content of the colored curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content of the solvent (E) is within this range, flatness during coating is improved, and color density is not insufficient when forming a color filter, thereby tending to improve display properties.

[0379] 〔8〕Leveling agent (F)

[0380] The colored curable resin composition of the present invention may contain a leveling agent (F). Examples of the leveling agent (F) include silicone surfactants (not containing fluorine atoms), fluorine-based surfactants, and silicone surfactants containing fluorine atoms. These surfactants may have polymerizable groups in their side chains.

[0381] Examples of the silicone surfactant (not having a fluorine atom) include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (trade names: manufactured by Toray-Dow Corning Corporation); KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.).

[0382] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (registered trademark) FC430 and Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.); Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, and Megafac RS-718-K (manufactured by DIC Corporation); FTOP (registered trademark) EF301, FTOP EF303, FTOP EF351, and FTOP EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.); Surflon (registered trademark) S381, Surflon S382, Surflon SC101, and Surflon SC105 (manufactured by Asahi Glass Co., Ltd.); and E5844 (manufactured by Daikin Fine Chemical Co., Ltd.). Research Institute) etc.

[0383] Examples of the silicone surfactant having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, and more specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Corporation).

[0384] The content of the leveling agent (F) relative to the total amount of the colored curable resin composition is preferably 0.001% to 0.2% by mass, more preferably 0.002% to 0.1% by mass, and more preferably 0.01% to 0.05% by mass. This content does not include the pigment dispersant described above. When the content of the leveling agent (F) is within this range, the flatness of the color filter can be improved.

[0385] 〔9〕Other ingredients

[0386] The colored curable resin composition of the present invention may contain additives known in the art, such as other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0387] <Method for producing a colored curable resin composition>

[0388] The colored curable resin composition of the present invention can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and an extender pigment (P), and optionally, a solvent (E), a leveling agent (F), a polymerization initiation aid (D1), and other components.

[0389] The lake pigment is preferably premixed with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size of the pigment reaches approximately 0.2 μm or less. In this process, part or all of the aforementioned pigment dispersant and resin (B) may be added as needed. When the colorant (A) further contains a pigment, the pigment dispersion is preferably prepared in the same manner as for the lake pigment dispersion.

[0390] The extender pigment (P) is preferably pre-mixed with a portion or all of the solvent (E) and then dispersed using a bead mill or the like. Alternatively, the coloring pigment and extender pigment (P) may be dispersed while being mixed. The desired colored curable resin composition can be prepared by mixing the remaining components into the pigment dispersion thus obtained to achieve a desired concentration.

[0391] When the colorant (A) contains a dye, each dye may be dissolved in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0392] The mixed colored curable resin composition is preferably filtered through a filter having a pore size of about 0.1 to 10 μm.

[0393] <Method for Manufacturing Color Filter>

[0394] The colored curable resin composition of the present invention is suitable as a material for a color filter. A color filter formed from the colored curable resin composition of the present invention is also an aspect of the present invention.

[0395] The color filter of the present invention can be formed by a method comprising applying the colored curable resin composition onto a substrate, drying the composition to form a colored composition layer, and curing the colored composition layer by exposure, etc. The color filter of the present invention has a colored pattern or a colored coating film.

[0396] Specific methods for producing colored patterns include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, which is then exposed and developed through a photomask. In photolithography, by not using a photomask and / or not developing during exposure, a colored coating film can be formed as a cured product of the colored composition layer.

[0397] The film thickness of the color filter of the present invention is not particularly limited and can be appropriately adjusted depending on the purpose and application. It is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0398] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass coated with silicon dioxide; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates obtained by forming thin films of aluminum, silver, or silver / copper / palladium alloys on the above substrates. Other color filter layers, resin layers, transistors, circuits, and the like may also be formed on these substrates.

[0399] The formation of each color pixel by photolithography can be performed using known or customary equipment and conditions. For example, the formation can be performed as follows.

[0400] First, a colored curable resin composition is applied onto a substrate, and then dried by heating (prebaking) and / or drying under reduced pressure to remove volatile components such as a solvent and dry the composition to obtain a smooth colored composition layer.

[0401] Examples of the coating method include spin coating, slit coating, and slit and spin coating.

[0402] The temperature during heat drying is preferably 30 to 120° C., more preferably 50 to 110° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0403] When drying under reduced pressure is performed, it is preferably performed at a pressure of 50 to 150 Pa and a temperature range of 20 to 25°C.

[0404] The film thickness of the colored composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the target color filter.

[0405] Next, the colored composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the desired application can be used.

[0406] The light source used for exposure is preferably one that emits light with a wavelength of 250 to 450 nm. For example, a filter that cuts off this wavelength range can be used to cut off light less than 350 nm, or a bandpass filter that cuts off these wavelengths can be used to selectively extract light near 436 nm, 408 nm, and 365 nm. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0407] In order to uniformly irradiate the entire exposure surface with parallel light or to accurately align the photomask and the substrate on which the colored composition layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

[0408] The exposed colored composition layer is brought into contact with a developer and developed to form a colored pattern on the substrate. By developing, the unexposed portion of the colored composition layer is dissolved in the developer and removed.

[0409] The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may further contain a surfactant.

[0410] The development method may be any of a paddle method, an immersion method, and a spray method. The substrate may be tilted at any angle during development. It is preferred that the substrate be rinsed with water after development.

[0411] Furthermore, the obtained colored pattern is preferably post-baked. The post-baking temperature is preferably 150 to 250° C., more preferably 160 to 235° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[0412] The colored curable resin composition of the present invention can be used to produce a color filter having excellent heat resistance and solvent resistance. This color filter is useful as a color filter for use in display devices (such as liquid crystal display devices, organic EL devices, and electronic paper) and solid-state imaging devices.

[0413] Example

[0414] Hereinafter, the colored curable resin composition of the present invention will be described in more detail with reference to Examples. "%" and "parts" in the Examples are % by mass and parts by mass unless otherwise specified.

[0415] <Production Example 1: Preparation of Lake Pigment (A1)>

[0416] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 15.3 parts of N-methylaniline (Tokyo Chemical Industry Co., Ltd.) and 60 parts of N,N-dimethylformamide were placed, and the resulting mixed solution was cooled with ice. Under ice cooling, 5.7 parts of 60% sodium hydride (Tokyo Chemical Industry Co., Ltd.) were added gradually over 30 minutes, and the mixture was stirred at room temperature for 1 hour while warming. 10.4 parts of 4,4'-difluorobenzophenone (Tokyo Chemical Industry Co., Ltd.) were added gradually to the reaction solution, and the mixture was stirred at room temperature for 24 hours. The reaction solution was added gradually to 200 parts of ice water, and the mixture was allowed to stand at room temperature for 15 hours. The water was removed by decantation, yielding a viscous solid as a residue. 60 parts of methanol was added to the viscous solid, and the mixture was stirred at room temperature for 15 hours. The precipitated solid was filtered and purified by column chromatography. The purified light yellow solid was dried at 60° C. under reduced pressure to obtain 9.8 parts of a compound represented by formula (CI-18).

[0417]

[0418] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 8.2 parts of the compound represented by formula (B-I-7), 10 parts of the compound represented by formula (C-I-18), and 20 parts of toluene were placed. Then, 12.2 parts of phosphorus oxychloride was added and stirred at 95-100°C for 3 hours. The reaction mixture was then cooled to room temperature and diluted with 170 parts of isopropyl alcohol. The diluted reaction solution was then poured into 300 parts of saturated brine, followed by the addition of 100 parts of toluene and stirring for 30 minutes. Stirring was stopped and the mixture was allowed to stand for 30 minutes, resulting in separation into an organic layer and an aqueous layer. After removing the aqueous layer by separation, the organic layer was washed with 300 parts of saturated brine. An appropriate amount of sodium sulfate was added to the organic layer, stirred for 30 minutes, and then filtered to obtain a dried organic layer. The resulting organic layer was evaporated to remove the solvent, yielding a bluish-purple solid. The bluish purple solid was then dried at 60° C. under reduced pressure to obtain 18.4 parts of a compound represented by formula (A-II-18).

[0419]

[0420] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 8 parts of the compound represented by the above formula (A-II-18) and 396 parts of methanol were added and stirred at room temperature for 30 minutes to prepare a blue solution. Subsequently, 396 parts of water were added to this blue solution and stirred at room temperature for another 30 minutes to obtain a reaction solution.

[0421] 53 parts of water were added to a beaker. 11.8 parts of Keggin-type phosphotungstic acid (manufactured by Aldrich) and 53 parts of methanol were added to the water and mixed at room temperature under an air atmosphere to prepare a phosphotungstic acid solution. The resulting phosphotungstic acid solution was added dropwise to the previously prepared reaction solution over 1 hour. After further stirring at room temperature for 30 minutes, the mixture was filtered to obtain a blue solid. The resulting blue solid was added to 200 parts of methanol, dispersed for 1 hour, and then filtered twice. The resulting blue solid was added to 200 parts of water, dispersed for 1 hour, and then filtered twice. The resulting blue solid was dried at 60°C under reduced pressure to obtain 17.1 parts of the compound represented by formula (A-I-18) [lake pigment (A1)].

[0422]

[0423] <Preparation of aqueous dispersion>

[0424] 14 parts of the compound represented by formula (AI-18), 2.5 parts of a dispersant (BYK (registered trademark)-LPN6919 (manufactured by BYK Chemicals Japan Ltd.)), 6 parts of a resin (B1) (based on solid content), 77.5 parts of propylene glycol monomethyl ether acetate, and 300 parts of 0.2 mm zirconium oxide beads were mixed and shaken for 6 hours using a paint conditioner (manufactured by Red Devil Co., Ltd.) to prepare a dispersion (A1).

[0425] <Production Example 2: Preparation of Xanthene Dye (A2)>

[0426] 20 parts of the compound represented by formula (1x) and 200 parts of N-propyl-2,6-dimethylaniline (Wako Pure Chemical Industries, Ltd.) were mixed under light-shielding conditions, and the resulting solution was stirred at 110°C for 6 hours. The resulting reaction solution was cooled to room temperature and then added to a mixture of 800 parts of water and 50 parts of 35% by weight hydrochloric acid. The mixture was stirred at room temperature for 1 hour to precipitate crystals. The precipitated crystals were collected as a residue by suction filtration and then dried to obtain the compound represented by formula (1-32) [Xanthene Dye (A2)].

[0427]

[0428] <Production Example 3: Preparation of Resin (B1)>

[0429] An appropriate amount of nitrogen gas was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen gas. 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. while stirring.

[0430] Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2.6 ]decyl-8-yl ester and acrylic acid-3,4-epoxy tricyclic [5.2.1.0 2.6 A mixed solution of 289 parts of a mixture of 9-decyl esters and 125 parts of propylene glycol monomethyl ether acetate.

[0431] On the other hand, a mixed solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain 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 converted to solid content of 115 mg-KOH / g. The weight average molecular weight (Mw) of resin (B1) was 1.06×10 4 , the dispersion is 2.08.

[0432] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using a GPC method under the following conditions.

[0433] Device: K2479 (manufactured by Shimadzu Corporation)

[0434] Chromatographic column: SHIMADZU Shim-pack GPC-80M

[0435] Column temperature: 40°C

[0436] Solvent: Tetrahydrofuran (THF)

[0437] Flow rate: 1.0 mL / min

[0438] Detector: RI

[0439] Calibration standard substances: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation).

[0440] The ratio of the polystyrene-equivalent weight average molecular weight to the number average molecular weight (Mw / Mn) obtained above was defined as the degree of dispersion.

[0441] <Examples 1 to 4, Comparative Example 1>

[0442] (1) Preparation of colored curable resin composition

[0443] The components listed in Table 1 were mixed to obtain a colored curable resin composition. The amounts of each component in Table 1 are expressed in parts by mass. As described below, the lake pigment (A1) and extender pigments (P1) to (P4) were previously mixed with a dispersant, resin (B1), and solvent (E1) or (E4) to prepare the colored curable resin composition as a dispersion. However, Table 1 shows the content of each component in the final colored curable resin composition. The values ​​in Table 1 represent the solid content (parts by mass) of each component.

[0444]

Table 1

[0445]

[0446] Resin (B1): indicates the total amount of resin (B1).

[0447] Solvent (E1): indicates the total amount of propylene glycol monomethyl ether acetate.

[0448] In addition, each component in Table 1 represents the following: Resin (B1) represents parts by mass in terms of solid content.

[0449] [1] Dispersion (A1): Dispersion (1)

[0450] [2] Dye (A2): the compound represented by formula (1-32) obtained in Preparation Example 2

[0451] [3] Resin (B1): Resin (B1) obtained in Production Example 3

[0452] [4] Polymerizable compound (C1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0453] [5] Polymerization initiator (D1): N-benzoyloxy-1-(4-phenylthiophenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; oxime compound)

[0454] [6] Extender Pigment Dispersion (P1): Zinc oxide dispersion. A premixed dispersion of zinc oxide (10 parts), an acrylic pigment dispersant (1.3 parts), and the solvent (E1) (88.7 parts) listed in Table 1 was used as a blending component when preparing the colored curable resin composition.

[0455] [7] Extender Pigment Dispersion (P2): Titanium oxide dispersion. A premixed dispersion of titanium oxide (10 parts), an acrylic pigment dispersant (3 parts), and the solvent (E1) (87 parts) listed in Table 1 was used as a blending component when preparing the colored curable resin composition.

[0456] [8] Extender pigment dispersion (P3): Silica dispersion (PGM-AC-0413; manufactured by Nissan Chemical Industries, Ltd., containing 30% extender pigment)

[0457] [9] Extender pigment dispersion (P4): Zirconia dispersion (SZR; manufactured by Sakai Chemical Co., Ltd., containing 30% extender pigment)

[0458]

[10] Solvent (E1): Propylene glycol monomethyl ether acetate

[0459] 〔11〕Solvent (E2): Ethyl lactate

[0460]

[12] Solvent (E3): Propylene glycol diacetate

[0461] 〔13〕Solvent (E4): Propylene glycol monomethyl ether

[0462]

[14] Leveling agent (F1): polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray-Dow Corning Corporation).

[0463] (2) Preparation of color coating film

[0464] A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) to a film thickness of 2 μm after post-baking. The composition was then pre-baked at 100°C for 3 minutes to form a colored composition layer. After cooling naturally, the composition was exposed to light at 150 mJ / cm² in an air atmosphere using an exposure device (TME-150RSK; manufactured by Topcon Corporation). 2 The colored composition layer was irradiated with light at an exposure dose of 100 nm (based on 365 nm). After the light irradiation, the colored composition layer was post-baked in an oven at 230° C. for 20 minutes to obtain a colored coating film.

[0465] (3) Chromaticity evaluation

[0466] The resulting colored coating film was spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). Using the characteristic function of illuminant C, the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ colorimetric system were measured. A larger Y value indicates higher brightness. The results are shown in Table 2.

[0467] (4) Heat resistance evaluation

[0468] The resulting colored coating film was heated in an oven at 230°C 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 these measured values ​​using the method described in JIS Z 8730:2009 (7. Color difference calculation method). The calculated value was converted into ΔEab of Comparative Example 1. The relative value (%) when the value is set as 100%. The results are shown in Table 2.

[0469] (5) Evaluation of solvent resistance

[0470] The resulting colored coating film was immersed in a large excess of N-methyl-2-pyrrolidone maintained at 23°C for 40 minutes and then thoroughly rinsed with water. The xy chromaticity coordinates (x, y) and Y were measured before and after immersion, and the color difference ΔEab was calculated from these measured values ​​using the method described in JIS Z8730:2009 (7. Color difference calculation method). The calculated value was converted into ΔEab of Comparative Example 1. The relative value (%) when the value is set as 100%. The results are shown in Table 2.

[0471] Comparative Example 2

[0472] Mix the following ingredients and use a bead mill to fully disperse the pigment.

[0473] (A) Colorant: CI Pigment Blue 15:6 (Pigment) 29.5 parts

[0474] 15 parts of acrylic pigment dispersant

[0475] 198 parts of propylene glycol monomethyl ether acetate

[0476] Next, the following components were mixed to obtain a colored curable resin composition.

[0477] (A) Dispersion (A1): Dispersion (1) 82 parts

[0478] (B) Resin; Resin (B-1) (solid content conversion) 50 parts

[0479] (C) polymerizable compound; (C-1); 50 parts of dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0480] (D) Polymerization initiator; (D-1); 14 parts of N-benzoyloxy-1-(4-phenylthiophenyl)octan-1-one-2-imine (Irgacure OXE 01; manufactured by BASF; oxime compound)

[0481] (F) Leveling agent; (F-1): 0.1 part of polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray-Dow Corning Co., Ltd.)

[0482] (E) solvent; (E-1); 597 parts of propylene glycol monomethyl ether acetate

[0483] (E) Solvent; (E-4); 149 parts of propylene glycol monomethyl ether

[0484] Furthermore, a colored coating film was produced from the resulting colored curable resin composition according to the procedure described in "(2) Production of Colored Coating Film" above. The resulting colored coating film was evaluated for chromaticity, heat resistance, and solvent resistance in the same manner as in Examples 1 to 4 and Comparative Example 1. The results are shown in Table 2.

[0485]

Table 2

[0486]

[0487] Industrial applicability

[0488] According to the colored curable resin composition of the present invention, a color filter having improved solvent resistance and heat resistance can be produced.

Claims

1. A colored curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and an extender pigment (P), and Colorants (A) include lake pigments and dyes, Dyes include xanthene dyes, The content of the dye in 100% by mass of the colorant (A) is 0.1 to 50% by mass. The extender pigment (P) is at least one selected from zinc oxide, titanium oxide, silicon dioxide and zirconium oxide. The content of the extender pigment (P) is 0.5% by mass to 10% by mass based on the total amount of the solid content of the colored curable resin composition.

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

3. The colored curable resin composition according to claim 1 or 2, wherein The compound (Aa) is a compound represented by formula (A-I), In formula (A-I), X + represents a cation represented by the formula (A-I-X), [Y] m- represents an m-valent anion containing oxygen and at least one element selected from tungsten, molybdenum, silicon and phosphorus, m represents any natural number, In the formula (A-I-X), R 41 ~R 44 Each independently represents: a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent; an alkyl group having 2 to 20 carbon atoms, wherein an oxygen atom is inserted between methylene groups constituting the alkyl group, but a plurality of oxygen atoms are not inserted adjacent to each other; 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 a hydrogen atom, R 41 With R 42 optionally bonded to form a ring together with the nitrogen atom to which they are bonded, R 43 With R 44 They are optionally bonded to form a ring together with the nitrogen atom to which they are bonded. R 47 ~R 54 Each independently represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group or an alkyl group having 1 to 8 carbon atoms. When the number of carbon atoms is 2 or more, an oxygen atom may be inserted between the methylene groups constituting the alkyl group, but multiple oxygen atoms are not inserted adjacently. 48 With R 52 optionally bonded to each other to form -NH-, -O-, -S- or -SO2-, T 1 represents a monovalent aromatic heterocyclic group which may have a substituent, When m is a natural number greater than 2, multiple X + It can be the same structure or different structures.

4. The colored curable resin composition according to claim 1 or 2, wherein The xanthene dye is a compound represented by formula (1a), In formula (1a), R 1 ~R 4 Each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a monovalent aralkyl group having 7 to 20 carbon atoms which may have a substituent, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, wherein the -CH2- group contained in the saturated hydrocarbon group and the aralkyl group is optionally replaced by -O-, -CO- or -NR 11 - Replacement, R 1 and R 2 Optionally, together they form a ring containing a nitrogen atom, R 3 and R 4 optionally together forming a ring comprising a nitrogen atom, R 5 Indicates -OH, -SO3 - 、-SO3H、-SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 、-SO3R 8 or -SO2NR 9 R 10 , R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, m represents an integer of 0 to 5. When m is 2 or greater, multiple R 5 Optional same or different, a represents an integer of 0 or 1, X represents a halogen atom, Z + express + N (R 11 4. Na + or K + , 4 R 11 Optional same or different, R 8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, wherein the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with halogen atoms, R 9 and R 10 Each independently represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the saturated aliphatic hydrocarbon group may be replaced by -O-, -CO-, -NH- or -NR 8 - Replacement, R 9 and R 10 optionally 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, and in formula (1a) there is -SO3 － In the case of － The quantity is 1.

5. The colored curable resin composition according to claim 4, wherein The content of the compound represented by formula (1a) is 50% by mass or more relative to the xanthene dye. A color filter formed from the colored curable resin composition according to claim 1 . A display device comprising the color filter according to claim 6 .

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