compound

Abstract

To provide a compound enabling improvement of color separation in a resulting color filter, and a colored resin composition containing the compound.SOLUTION: The foregoing problem is solved by a compound represented by formula (I). [In the formula, M1 is Ga or In; R1 is a substituted or unsubstituted C2-20 unsaturated aliphatic hydrocarbon group; R2 is H, a substituted or unsubstituted C1-20 hydrocarbon group, or a single bond linking Z2 and R1; Z1 and Z2 are a single bond or an oxygen atom; X1-X4 are -R3, -OR3, -SR3, a halogen atom, a nitro group, or a substituted or unsubstituted sulfamoyl group; R3 is a substituted or unsubstituted C1-20 hydrocarbon group; n1-n4 are integers from 0 to 4.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound, a colored resin composition, a color filter, and a display device. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored resin compositions. Aluminum phthalocyanine pigments are known as green or cyan colorants for such colored resin compositions. Patent Document 1 discloses an aluminum phthalocyanine pigment having a specific structure as a colorant, and describes that the color difference before and after post-baking can be reduced. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2022 / 024926 Summary of the Invention [Problem to be solved by the invention]

[0004] The colorant of Patent Document 1 exhibits a maximum absorption in the red region (610 to 750 nm) and is used in green or cyan color filters. However, it is preferable that the green or cyan color filter exhibits a large absorption at a wavelength (hereinafter sometimes referred to as a second absorption wavelength) that is approximately 30 to 80 nm shorter than the maximum absorption wavelength (hereinafter sometimes referred to as a first absorption wavelength), which is close to the maximum absorption wavelength. The closer the absorption at the second absorption wavelength is to the absorption at the first absorption wavelength, the more likely it is that color separation (color purity) in the visible region will be improved and the more likely it is that sensor signal noise will be reduced. The present invention has been made in light of the above-mentioned circumstances, and an object of the present invention is to improve the color separation of phthalocyanine colorants (e.g., green or cyan colorants) that exhibit a maximum absorption in the red region (610 to 750 nm). [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] A compound represented by formula (I): [ka] [In formula (I), M 1 represents Ga or In. R 1 represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or Z 2 and R 1 represents a single bond connecting Z 1 and Z 2 each independently represents a single bond or an oxygen atom. X 1 ~X 4 are each independently -R 3 , -OR 3 , -SR 3 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R 3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. n1 to n4 each independently represent an integer of 0 to 4.] [2] A colored resin composition comprising the compound according to [1] and a resin. [3] The colored resin composition according to [2], further comprising a polymerizable compound and a polymerization initiator. [4] A color filter formed from the colored resin composition according to [2] or [3]. [5] A display device comprising the color filter according to [4]. [Effects of the Invention]

[0006] According to the compound of the present invention, it is possible to improve the color separation property in a color filter formed from a colored resin composition containing the compound. DETAILED DESCRIPTION OF THE INVENTION

[0007] <<Compound>> The present invention relates to a compound represented by the following formula (I) (hereinafter referred to as compound (I)). Compound (I) can improve color separation in a color filter formed from a colored resin composition containing the compound, increasing color purity and facilitating reduction in sensor signal noise. It also makes it easier to adjust the color material composition of a green or cyan color filter, facilitating reduction in the amount of yellow colorant added. It is also possible to reduce the color difference before and after post-baking.

[0008] [ka] [In formula (I), M 1 represents Ga or In. R 1 represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or Z 2 and R 1 represents a single bond connecting Z 1 and Z 2 each independently represents a single bond or an oxygen atom. X 1 ~X 4 are each independently -R 3 , -OR 3 , -SR 3 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. n1 to n4 each independently represent an integer of 0 to 4.]

[0009] R 1 The unsaturated aliphatic hydrocarbon group represented by the formula (I) may be linear or cyclic (ie, an unsaturated alicyclic hydrocarbon group). R 1 Examples of the chain unsaturated aliphatic hydrocarbon group represented by the formula: Ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group), alkenyl groups such as 1-(1,1-dimethylethyl)ethenyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, and icocenyl; Ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group (e.g., 2-pentynyl group, 3-pentynyl group, 4-pentynyl group), 1-methyl-3-butynyl group, 1,1-dimethyl-2-propynyl group, hexynyl group (e.g., 2-hexynyl group, 5-hexynyl group), 1-ethyl-3-butynyl group, heptynyl group (e.g., 2-heptynyl group, 6- alkynyl groups such as a 1-octynyl group, a 2-octynyl group, a 7-octynyl group, a 1-octynyl group, a 2-octynyl group, a 7-octynyl group, a 2-octynyl group, a 7-octynyl group, a 2-octynyl group, a 2-octynyl group, a 7-octynyl group, a 2-octynyl group, a 2-octynyl group, a 9-octynyl group, a 2-decynyl group, a 2-decynyl group, a 9-decynyl group, a 2 ... The alkenyl group and the alkynyl group are preferably Z 1 Preferably, the unsaturated bond is at the end not bonded to the alkyl group.

[0010] R 1 Examples of the unsaturated alicyclic hydrocarbon group represented by the formula: cycloalkenyl groups such as a cyclohexenyl group (e.g., a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group; unsaturated polycyclic hydrocarbon groups such as norbornenyl groups; etc.

[0011] R 1 The unsaturated aliphatic hydrocarbon group represented by the formula (I) preferably has 2 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, and even more preferably 3 to 6 carbon atoms.

[0012] R 1The substituents which the unsaturated aliphatic hydrocarbon group represented by the formula (I) may have include an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 and -NR a1 R a2 etc. where R a1 and R a2 R each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. a1 and R a2 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula 2 and R 3 Examples of hydrocarbon groups having 1 to 20 carbon atoms and represented by the following formula are given below. a1 and R a2 are each independently preferably a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 15 carbon atoms.

[0013] R 1 Examples of the aromatic hydrocarbon group constituting the substituent that may be possessed by the unsaturated aliphatic hydrocarbon group represented by the formula: Phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)-4-methylphenyl group, 4-butylphenyl Examples of such groups include a phenyl group, a 4-pentylphenyl group, a 2,6-bis(1-methylethyl)phenyl group, a 2,4,6-tris(1-methylethyl)phenyl group, a 4-cyclohexylphenyl group, a 2,4,6-trimethylphenyl group, a 4-octylphenyl group, a 4-(1,1,3,3-tetramethylbutyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-methyl-2-naphthyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthryl group, a 2-dodecylphenyl group, a 3-dodecylphenyl group, a 4-dodecylphenyl group, a perylenyl group, a chrysenyl group, and a pyrenyl group.

[0014] The aromatic hydrocarbon group preferably has 6 to 10 carbon atoms, and more preferably 6 to 8 carbon atoms.

[0015] The aromatic hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 and -NR a1 R a2 (However, R a1 and R a2 is the same as above).

[0016] R 1 The heterocyclic group constituting the substituent that the unsaturated aliphatic hydrocarbon group represented by the formula (I) may have may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring component. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0017] Examples of heterocycles containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, and piperazine; 5-membered unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole; 6-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, and 1,3,5-triazine; fused bicyclic heterocycles such as indazole, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperidine; and fused tricyclic heterocycles such as carbazole, acridine, and phenazine. Examples of heterocycles containing only oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone; 5-membered unsaturated heterocycles such as furan; 6-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; fused bicyclic heterocycles such as 1-benzofuran, benzopyran, benzodioxole, chroman, and isochroman; and fused tricyclic heterocycles such as xanthene and dibenzofuran. Examples of heterocycles containing only sulfur atoms as heteroatoms include 5-membered saturated heterocycles such as dithiolane; 6-membered saturated heterocycles such as thiane and 1,3-dithiane; 5-membered unsaturated heterocycles such as thiophene; 6-membered unsaturated heterocycles such as 4H-thiopyran; fused bicyclic heterocycles such as benzothiopyrans (e.g., benzotetrahydrothiopyran) and benzothiophene; and fused tricyclic heterocycles such as thianthrene and dibenzothiophene. Examples of heterocycles containing a nitrogen atom and an oxygen atom as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, and 2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; and fused tricyclic heterocycles such as phenoxazine. Examples of heterocycles containing a nitrogen atom or a sulfur atom as a heteroatom include monocyclic heterocycles such as thiazole; fused bicyclic heterocycles such as benzothiazole; and fused tricyclic heterocycles such as phenothiazine.

[0018] The heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and even more preferably 3 to 20 carbon atoms.

[0019] The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 and -NR a1 R a2 (However, R a1 and R a2 is the same as above).

[0020] The bonding position of the heterocycle is the position where any hydrogen atom contained in each ring is eliminated.

[0021] R 1Examples of halogen atoms constituting the substituents that the unsaturated hydrocarbon group represented by the formula (I) may have include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0022] R 2 and R 3 The hydrocarbon group represented by the formula (I) has 1 to 20 carbon atoms, and more preferably 1 to 15 carbon atoms.

[0023] R 2 and R 3 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0024] R 2 and R 3 Examples of the saturated or unsaturated chain hydrocarbon group represented by the formula (I) include straight-chain alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, and an icosyl group; Isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 1,1,2-trimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl branched alkyl groups such as butyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl, and 1-butylhexyl; Ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group), alkenyl groups such as 1-(1,1-dimethylethyl)ethenyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, and icocenyl; Ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group (e.g., 2-pentynyl group, 3-pentynyl group, 4-pentynyl group), 1-methyl-3-butynyl group, 1,1-dimethyl-2-propynyl group, hexynyl group (e.g., 2-hexynyl group, 5-hexynyl group), 1-ethyl-3-butynyl group, heptynyl group (e.g., 2-heptynyl group, 6- alkynyl groups such as a 1-octynyl group, a 2-octynyl group, a 7-octynyl group, a 1-octynyl group, a 2-octynyl group, a 7-octynyl group, a 2-octynyl group, a 7-octynyl group, a 2-octynyl group, a 2-octynyl group, a 7-octynyl group, a 2-octynyl group, a 2-octynyl group, a 9-octynyl group, a 2-decynyl group, a 2-decynyl group, a 9-decynyl group, a 2 ... etc. R 2 and R 3 The saturated chain hydrocarbon group (that is, a straight chain alkyl group, a branched chain alkyl group) represented by the formula (I) preferably has 1 to 10 carbon atoms, more preferably 1 to 7 carbon atoms, and even more preferably 1 to 5 carbon atoms. R 2 and R 3 The unsaturated chain hydrocarbon group (that is, alkenyl group, alkynyl group) represented by the formula (I) preferably has 2 to 10 carbon atoms, more preferably 2 to 7 carbon atoms, and even more preferably 2 to 5 carbon atoms.

[0025] R 2 and R 3 Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by the formula: Cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl cycloalkyl groups such as a cyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, a 4,4-dimethylcyclohexyl group, a cyclooctyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; cycloalkenyl groups such as a cyclohexenyl group (e.g., a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl, and bicyclo[2.2.2]octyl; etc.

[0026] R 2 and R 3 The saturated or unsaturated alicyclic hydrocarbon group represented by the formula (I) preferably has 3 to 10 carbon atoms.

[0027] R 2 and R 3Examples of the aromatic hydrocarbon group represented by the formula (I) include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)-4-methylphenyl group, a 4- aromatic hydrocarbon groups such as a butylphenyl group, a 4-pentylphenyl group, a 2,6-bis(1-methylethyl)phenyl group, a 2,4,6-tris(1-methylethyl)phenyl group, a 4-cyclohexylphenyl group, a 2,4,6-trimethylphenyl group, a 4-octylphenyl group, a 4-(1,1,3,3-tetramethylbutyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-methyl-2-naphthyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthryl group, a 2-dodecylphenyl group, a 3-dodecylphenyl group, a 4-dodecylphenyl group, a perylenyl group, a chrysenyl group, and a pyrenyl group;

[0028] R 2 and R 3 The aromatic hydrocarbon group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, further preferably 6 to 10 carbon atoms, and particularly preferably 6 to 8 carbon atoms.

[0029] R 2 and R 3 The hydrocarbon group represented by the formula (I) may be a group obtained by combining the above-mentioned hydrocarbon groups (for example, an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group), aralkyl groups such as a benzyl group, a (2-methylphenyl)methyl group, a (3-methylphenyl)methyl group, a (4-methylphenyl)methyl group, a (2-ethylphenyl)methyl group, a (3-ethylphenyl)methyl group, a (4-ethylphenyl)methyl group, a (2-(tert-butyl)phenyl)methyl group, a (3-(tert-butyl)phenyl)methyl group, a (4-(tert-butyl)phenyl)methyl group, a (3,5-dimethylphenyl)methyl group, a 1-phenylethyl group, a 1-methyl-1-phenylethyl group, a 1,1-diphenylethyl group, a (1-naphthyl)methyl group, and a (2-naphthyl)methyl group; arylalkenyl groups such as a 1-phenylethenyl group, a 2-phenylethenyl group (phenylvinyl group), a 3-phenyl-2-propenyl group, a 2,2-diphenylethenyl group, and a 2-phenyl-2-(1-naphthyl)ethenyl group; arylalkynyl groups such as a phenylethynyl group, a 3-phenyl-2-propynyl group, and a 4-phenyl-3-butynyl group; a phenyl group to which one or more phenyl groups are bonded, such as a biphenylyl group or a terphenylyl group; Examples include a cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl(phenyl)methyl)phenyl group. These have 20 or less carbon atoms, preferably 7 to 18 carbon atoms, and more preferably 7 to 15 carbon atoms.

[0030] R 2 and R 3 The group represented by the formula (I) may be a group combining the hydrocarbon groups listed above (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group), such as an alkyl group to which one or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a (2-methylcyclohexyl)methyl group, a cyclohexylethyl group, or an adamantylmethyl group. These have 20 or less carbon atoms, preferably 4 to 15 carbon atoms, and more preferably 4 to 10 carbon atoms.

[0031] R2 and R 3 The hydrocarbon group represented by R may have a substituent. 2 and R 3 The substituent of the hydrocarbon group represented by the formula (I) is a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 and -NR a1 R a2 (However, R a1 and R a2 is the same as above).

[0032] R 2 and R 3 The heterocyclic group constituting the substituent that may be possessed by the hydrocarbon group having 1 to 20 carbon atoms, represented by the following formula (1), may be a monocyclic or polycyclic ring, and is preferably a heterocyclic ring containing a heteroatom as a ring component. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom. The heterocycle includes R 1 Examples of heterocyclic groups include the same heterocyclic groups as those used as substituents on the unsaturated aliphatic hydrocarbon groups represented by the following formula: The heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and even more preferably 3 to 20 carbon atoms. The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 and -NR a1 R a2 (However, R a1 and R a2 is the same as above). The bonding position of the heterocycle is the position where any hydrogen atom contained in each ring is eliminated.

[0033] R 2 and R 3 Examples of halogen atoms constituting the substituents that may be possessed by the hydrocarbon group represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0034] R 2 Z 2 and R 1 When R is a single bond connecting 1 Part or all of *-Z 2 -P(=O)-Z 1 -* (* represents a bond) together to form a ring. That is, R 2 Z 2 and R 1 When R is a single bond connecting 1 and Z, an arbitrary carbon atom in the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent represented by 2 The bond formed by sharing a pair of electrons between 2 This corresponds to a single bond represented by the formula:

[0035] R 1 Part or all of *-Z 2 -P(=O)-Z 1 In a ring formed together with -* (* represents a bond), an unsaturated bond may be formed between carbon atoms that are members of the ring, an unsaturated bond may be formed between a carbon atom that is a member of the ring and a carbon atom that is not a member of the ring, or an unsaturated bond may be formed between carbon atoms that are not members of the ring.

[0036] X 1 ~X 4 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom being preferred.

[0037] X 1 ~X 4 The sulfamoyl group represented by the formula is represented by *-SO2-NH2 (* represents a bond). X 1~X 4 The sulfamoyl group represented by the formula X may have a substituent. 1 ~X 4 The substituent of the sulfamoyl group represented by R 1 and specifically, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR a1 , -CO2R a1 , -SR a1 , -SO2R a1 , -SO3R a1 , -SO2NR a1 R a2 and -NR a1 R a2 (However, R a1 and R a2 is the same as above).

[0038] X 1 ~X 4 -R expressed as 3 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, even more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, still more preferably a linear or branched alkyl group having 1 to 5 carbon atoms, and particularly preferably a tert-butyl group.

[0039] In formula (I), R 1 teeth, A chain unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent is preferred, A chain unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent is more preferred, A chain unsaturated aliphatic hydrocarbon group having 2 to 7 carbon atoms which may have a substituent is more preferred, An alkynyl group having 2 to 7 carbon atoms which may have a substituent is even more preferred, An alkynyl group having 4 to 7 carbon atoms which may have a substituent is particularly preferred. R 1When the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by the formula (I) has a substituent, the substituent is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and particularly preferably a phenyl group.

[0040] In formula (I), R 2 teeth, a hydrogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a chain unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent, or Z 2 and R 1 A single bond connecting a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, a chain unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 12 carbon atoms which may have a substituent, an arylalkynyl group having 8 to 12 carbon atoms which may have a substituent, or Z 2 and R 1 A single bond connecting a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, a chain unsaturated aliphatic hydrocarbon group having 2 to 7 carbon atoms which may have a substituent, or Z 2 and R 1 A single bond connecting An alkynyl group having 2 to 7 carbon atoms which may have a substituent is particularly preferred. R 2 When the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by the formula (I) has a substituent, it is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and particularly preferably a phenyl group.

[0041] Z 1 and Z 2 may each independently be a single bond or an oxygen atom, but it is preferable that all of them are oxygen atoms.

[0042] Especially Z 1 and Z 2 If is an oxygen atom, R 1 and R 2 is a chain unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, or R 1 is a chain unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and R 2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent, or Z 2 and R 1 and R 1 and R 2 is a chain unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, or R 1 is a chain unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, and R 2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 12 carbon atoms which may have a substituent, an arylalkynyl group having 8 to 12 carbon atoms which may have a substituent, or Z 2 and R 1 It is more preferable that the bond is a single bond connecting Also Z 1 and Z 2 is a single bond, and Z 1 is an oxygen atom and Z 2 If is a single bond, R 1 is a chain unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and R 2 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent; R 1 is a chain unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, and R 2 is more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Also Z 1 is a single bond and Z 2 If is an oxygen atom, R 1is a chain unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and R 2 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a hydrogen atom, and R 1 is a chain unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms which may have a substituent, and R 2 is more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a hydrogen atom.

[0043] In formula (I), X 1 ~X 4 are each independently -R 3 Alternatively, a halogen atom is preferred, a saturated chain hydrocarbon group having 1 to 4 carbon atoms or a halogen atom is more preferred, and a halogen atom is even more preferred.

[0044] In formula (I), n1 to n4 are each independently preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0045] In formula (I), M 1 may be either Ga or In, but is preferably Ga.

[0046] The compound represented by formula (I) is preferably a compound represented by formula (IA) to formula (IK).

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka] [In formula (IA) ~ formula (IK), R 1 , R 2 , Z 1 and Z 2 is the same as above, and n represents an integer of 1 to 3.

[0058] Examples of the compound represented by formula (IA) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IA) and having a central metal (M 1The compounds in which the central metal (M) is Ga are referred to as Compound (IA-1 Ga) to Compound (IA-272 Ga), respectively, and have groups shown in Nos. 1 to 272 in Formula (IA). 1 The compounds in which IA-1 is In are referred to as compounds (IA-1 In) to (IA-272 In), respectively. Examples of the compound represented by formula (IB) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IB) and having a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IB-1 Ga) to Compound (IB-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in Formula (IB). 1 The compounds in which IB-1 is In are referred to as compound (IB-1 In) to compound (IB-272 In), respectively. Examples of the compound represented by formula (IC) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IC) and having a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IC-1 Ga) to Compound (IC-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in the formula (IC). 1 The compounds in which (IC-1) is In are referred to as compounds (IC-1 In) to (IC-272 In), respectively. Examples of the compound represented by formula (ID) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (ID) and having a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (ID-1 Ga) to Compound (ID-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in the formula (ID). 1 The compounds in which each of the above is In are referred to as Compound (ID-1 In) to Compound (ID-272 In), respectively. Examples of the compound represented by formula (IE) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IE) and having a central metal (M1 The compounds in which the central metal (M) is Ga are referred to as Compound (IE-1 Ga) to Compound (IE-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in the formula (IE). 1 The compounds in which IE-1 is In are referred to as compounds (IE-1 In) to (IE-272 In), respectively. Examples of the compound represented by formula (IF) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IF) and having a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IF-1 Ga) to Compound (IF-272 Ga), respectively. 1 The compounds in which IF-1 is In are referred to as compound (IF-1 In) to compound (IF-272 In), respectively. Examples of the compound represented by formula (IG) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IG) and having a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IG-1 Ga) to Compound (IG-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in the formula (IG). 1 The compounds in which IG-1 is In are referred to as compounds (IG-1 In) to (IG-272 In), respectively. Examples of the compound represented by formula (IH) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IH) and a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IH-1 Ga) to Compound (IH-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in Formula (IH). 1 The compounds in which (IH-1) is In are referred to as compounds (IH-1 In) to (IH-272 In), respectively. Examples of the compound represented by formula (II) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (II) and having a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (II-1 Ga) to Compound (II-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in Formula (II). 1 The compounds in which (II-1) is In are referred to as compound (II-1 In) to compound (II-272 In), respectively. Examples of the compound represented by formula (IJ) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IJ) and a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IJ-1 Ga) to Compound (IJ-272 Ga), respectively, and have the groups shown in Nos. 1 to 272 in Formula (IJ), 1 The compounds in which (IJ-1) is In are referred to as Compound (IJ-272) In, respectively. Examples of the compound represented by formula (IK) include compounds having groups shown in Nos. 1 to 272 in Tables 1 to 5. Hereinafter, compounds having groups shown in Nos. 1 to 272 in formula (IK) and a central metal (M 1 The compounds in which the central metal (M) is Ga are referred to as Compound (IK-1 Ga) to Compound (IK-272 Ga), respectively, and have groups shown in Nos. 1 to 272 in the formula (IK). 1 The compounds in which (IK-1) is In are referred to as compounds (IK-1 In) to (IK-272 In), respectively.

[0059] In addition, "R" in Tables 1 to 3 and Table 5 1 " column and "R 2 " column, i-1 to i-22 and ii-1 to ii-2 correspond to groups represented by formulae (i-1) to (i-22) and formulae (ii-1) to (ii-2), respectively. Also, in Table 4, "R 1 and R 2The groups ca-1 to ca-2 and cb-1 described in the "Group formed by" column correspond to the groups represented by formula (ca-1) to formula (ca-2) and formula (cb-1), respectively. 1 and R 2 The group formed by R 2 Z 2 and R 1 When it is a single bond connecting 2 -P(=O)-Z 1 -* (* represents a bond) represents a group that binds to the bond *. In formula (ca-1) ~ formula (ca-2), R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent. Examples of the substituent that the alkyl group having 1 to 8 carbon atoms may have include R 1 and R 3 Examples of the substituents include the same as those that may be contained in the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by the following formula: Also, in Table 4, "R 8 " cc-1 corresponds to the group represented by formula (cc-1). * represents a bond.

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [Table 1]

[0065] [Table 2]

[0066] [Table 3]

[0067] [Table 4]

[0068] [Table 5]

[0069] Compound (I) has excellent color separation properties, is excellent in terms of ease of adjusting the color material composition of green or cyan color filters, and also has excellent heat resistance. The color separation properties and heat resistance of Compound (I) can be evaluated by forming a color filter (hereinafter referred to as a color filter for evaluation) using Compound (I) alone without combining it with other dyes, and observing the spectrum and heat resistance of this color filter. The color separation of the evaluation color filter was determined by the method described in the Examples below, and Abs(λ max-45 ) / Abs(λ max ) (wherein, Abs(λ max ) indicates the absorbance at the maximum absorption wavelength, and Abs(λ max-45 ) is the maximum absorption wavelength λ max The maximum absorption wavelength (λ max )" means the wavelength with the greatest absorbance when there are two or more maximum absorption wavelengths. The color separation of the evaluation color filter is preferably 0.60 or more, more preferably 0.65 or more, and even more preferably 0.70 or more. The higher the color separation (the closer to 1), the higher the color purity and the reduced signal noise of the sensor, making this a preferable characteristic of the color filter. The upper limit of the color separation is preferably 1.00 or less, and may be 0.99 or less or 0.95 or less.

[0070] In the evaluation color filter, the ease of adjusting the color material composition was determined by the method described in the Examples below, and Abs(λ 450 ) / Abs(λ max ) (where, Abs(λ 450 ) indicates absorbance at a wavelength of 450 nm, and Abs(λ max ) is the maximum absorption wavelength λ max (The absorbance at 1000 kJ / s is shown). When producing a cyan color filter, the short wavelength side absorption intensity ratio of the color filter for evaluation is preferably 0.01 to 0.30, more preferably 0.01 to 0.20, and even more preferably 0.01 to 0.10. Furthermore, when preparing a green color filter, the short wavelength side absorption intensity ratio of the color filter for evaluation is preferably 0.01 or more, more preferably 0.03 or more, and even more preferably 0.05 or more, and the upper limit is not particularly limited, but may be 0.30 or less or 0.20 or less. The larger the short wavelength side absorption intensity ratio, the more the amount of yellow colorant added can be reduced when preparing a green color filter, which is preferable as a spectral characteristic of the color filter.

[0071] The heat resistance of the evaluation color filter is evaluated by the absorbance retention rate at the maximum absorption wavelength before and after heating for 10 minutes at 260° C. The absorbance retention rate of the evaluation color filter is, for example, 85 to 100%, preferably 90 to 100%, more preferably 95 to 100%, and particularly preferably 98 to 100%.

[0072] Furthermore, it is preferable that Compound (I) has a color that is easy to use as a colorant for a green or cyan color filter. For example, it is preferable that Compound (I) has a color that is easy to use as a colorant for a green or cyan color filter. For example, it is preferable that Compound (I) has a maximum absorption wavelength (λ) of 500 nm, 600 nm, or 730 nm in the color filter for evaluation. max ) to the absorbance at (Abs(λ 500 ) / Abs(λ max ), Abs(λ 600 ) / Abs(λ max ), Abs(λ 730 ) / Abs(λ max ) are determined according to the method in the Examples described below, and their values ​​are preferably as follows:

[0073] Abs(λ 500 ) / Abs(λ max ) is, for example, 0.00 to 0.10, preferably 0.00 to 0.05, and more preferably 0.00 to 0.02. 500 ) / Abs(λ max ) is smaller, the compound (I) can be more easily used as a colorant for producing a green or cyan color filter.

[0074] Abs(λ 600 ) / Abs(λ max ) is, for example, 0.00 to 0.60, preferably 0.10 to 0.50, and more preferably 0.15 to 0.45. 600 ) / Abs(λ max When the saturation coefficient (a) of the compound (I) is within this range, the compound (I) can be easily used as a colorant for producing a green or cyan color filter.

[0075] Abs(λ 730 ) / Abs(λ max ) is, for example, 0.00 to 0.95, preferably 0.10 to 0.95, and more preferably 0.20 to 0.95. 730 ) / Abs(λ max When the saturation coefficient (a) of the compound (I) is within this range, the compound (I) can be easily used as a colorant for producing a green or cyan color filter.

[0076] The maximum absorption wavelength (λ max ) (however, when there are two or more maximum absorption wavelengths, it means the wavelength with the greatest absorbance) is, for example, in the range of 650 to 730 nm, preferably in the range of 670 to 720 nm, and more preferably in the range of 680 to 710 nm. max When the saturation coefficient (a) of the compound (I) is within this range, the compound (I) can be easily used as a colorant for producing a green or cyan color filter.

[0077] Compound (I) can be produced, for example, by appropriately reacting a compound represented by formula (III) with a compound represented by formula (IV).

[0078] [ka] [In formula (I), formula (III) and formula (IV), M 1 , R 1 , R 2 , Z 1 , Z 2 , X 1 ~X 4 and n1 to n4 are the same as above.]

[0079] <<Colored resin composition>> The present invention encompasses a colored resin composition containing the above-mentioned compound (I) and a resin (hereinafter, sometimes referred to as resin (B)). The present invention also encompasses a colored resin composition further comprising a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention preferably contains the above-mentioned compound (I) (hereinafter, sometimes referred to as colorant (A1)) as a colorant (hereinafter, sometimes referred to as colorant (A)). The colored resin composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.

[0080] <Colorant (A)> The content of the colorant (A1) is preferably 0.5 to 70 mass%, more preferably 1 to 55 mass%, even more preferably 2 to 50 mass%, still more preferably 8 to 40 mass%, and particularly preferably 10 to 30 mass%, of the total amount of solids in the colored resin composition. In this specification, the term "total amount of solids" refers to the total amount of components excluding the solvent from the colored resin composition of the present invention. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0081] The content of the colorant (A1) may be, for example, 20 to 100% by mass of the total amount of the colorant (A). However, it is preferably contained within a range that does not impair the effect of the colorant (A1) in terms of color separation properties and the ease of adjusting the colorant composition, and is, for example, 40 to 100% by mass, more preferably 70 to 100% by mass, and particularly preferably 90 to 100% by mass.

[0082] The colorant (A) may further contain a colorant (hereinafter, sometimes referred to as colorant (A2)) different from the colorant (A1). The colorant (A2) may be either a dye or a pigment.

[0083] Examples of dyes include compounds classified as compounds having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha).

[0084] Examples of dyes include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, thiazole dyes, oxazine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferred.

[0085] Specific examples of dyes include CI Solvent Yellow 4 (hereinafter, the term CI Solvent Yellow will be omitted and only the numbers will be used. The same applies to the other dyes.), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, and 189; CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 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; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 177, 178, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 23 82, 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; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 , 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid dyes such as 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; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 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 6, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Dyes, such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, 60, etc. CI Basic Red 1, 9, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive dyes, such as CI Reactive Red 36; CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; 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; 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; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI 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; CI Mordant dyes, such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; Examples include CI Vat dyes such as CI Vat Green 1; These dyes may be one type of dye or a plurality of dyes for each color, or dyes of each color may be combined.

[0086] Examples of pigments include those classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 246, 254, 255, 264, 265, 266, 268, 269, 273, 291; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1 and 7; One or more of these pigments may be used for each color, or pigments of each color may be combined.

[0087] The pigment as colorant (A2) and the above-mentioned colorant (A1) may be subjected to, as necessary, rosin treatment, surface treatment using a pigment derivative having an acidic or basic group introduced therein, grafting treatment onto the pigment surface with a polymer compound, atomization treatment using sulfuric acid atomization, washing treatment with an organic solvent or water to remove impurities, or treatment to remove ionic impurities using an ion exchange method. The particle size of the pigment and colorant (A1) is preferably approximately uniform. By adding a pigment dispersant and dispersing the pigment and colorant (A1), a pigment dispersion in which the pigment and colorant (A1) are uniformly dispersed in the pigment dispersant solution can be obtained. The pigment and colorant (A1) may be dispersed individually or in a mixture of two or more types.

[0088] Examples of pigment dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of pigment dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie).

[0089] When a pigment dispersant is used, the amount used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 15 parts by mass or more and 180 parts by mass or less, and even more preferably 20 parts by mass or more and 160 parts by mass or less, relative to 100 parts by mass of the total of the pigment and colorant (A1). When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a more uniformly dispersed state tends to be obtained.

[0090] The content of the yellow colorant (i.e., yellow dye and yellow pigment) as the colorant (A2) in the colorant (A) is, for example, 0 to 50 mass %, preferably 10 to 40 mass %, and more preferably 20 to 35 mass %, of the total amount of the colorant (A).

[0091] The content of colorants other than the yellow colorant as colorant (A2) in the colorant (A) (for example, green colorants such as green dyes and green pigments) is, for example, 0 to 50 mass %, preferably 5 to 40 mass %, and more preferably 10 to 30 mass %, of the total amount of the colorant (A).

[0092] The content of the colorant (A) in the colored resin composition is preferably 0.5 to 80 mass%, more preferably 1 to 70 mass%, even more preferably 2 to 55 mass%, still more preferably 8 to 50 mass%, and particularly preferably 10 to 40 mass%, based on the total amount of solids. When the content of the colorant (A) is within the above range, it becomes easier to obtain the desired spectrum and color density.

[0093] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6], and it is preferably at least one selected from resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added and a structural unit derived from (c), and which contains a structural unit derived from (a) to which (b) has not been added; Resin [K4']: a copolymer having a structural unit derived from (a) to which (b) has been added and a structural unit derived from (c), but not containing a structural unit derived from (a) to which (b) has not been added; Resin [K5]: a copolymer having structural units derived from (b) to which (a) has been added and structural units derived from (c) (which may contain, but preferably does not contain, structural units derived from (b) to which (a) has not been added); Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further adding a carboxylic acid anhydride, and a structural unit derived from the (c).

[0094] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; 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; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; unsaturated dicarboxylic acid 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]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.

[0095] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0096] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0097] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0098] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, 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(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0099] 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 (BI), and compounds represented by formula (BII).

[0100] [ka]

[0101] [In formula (BI) and formula (BII), R e and R f 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 with a hydroxy group. X e and X fis a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0102] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R e and R f Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0103] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X e and X f Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0104] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formula (BI-1), (BI-3), (BII-5), (BI-7), (BI-9) or (BI-11) to (BI-15) are preferred, and compounds represented by formula (BI-1), (BI-7), (BI-9) or (BI-15) are more preferred.

[0105] [ka]

[0106] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formula (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) or (BII-11) to (BII-15) are preferred, and compounds represented by formula (BII-1), (BII-7), (BII-9) or (BII-15) are more preferred.

[0107] [ka]

[0108] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0109] 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, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

[0110] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0111] As (b), (b1) is preferable in that it can further increase the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter. Furthermore, (b1-2) is more preferable in that the storage stability of the colored resin composition is excellent.

[0112] Examples of (c) include (meth)acrylic acid ester monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters, and vinyl monomers having an unsaturated aliphatic hydrocarbon ring, an unsaturated heterocyclic ring, or an aromatic ring. Examples of the (meth)acrylic acid ester monomer include (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, such as 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, and cyclopentyl (meth)acrylate; (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, such as allyl (meth)acrylate and propargyl (meth)acrylate; Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate (commonly known in the technical field as "dicyclopentanyl (meth)acrylate" and sometimes called "tricyclodecyl (meth)acrylate"), isobornyl (meth)acrylate, and adamantyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), and dicyclopentanyloxyethyl (meth)acrylate; (meth)acrylic acid esters having an aromatic ring, such as phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and phenoxybenzyl (meth)acrylate; Examples thereof include hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate. Examples of the unsaturated dicarboxylic acid ester include dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate.

[0113] Among these unsaturated carboxylic acid esters, C esters such as methyl methacrylate and 2-ethylhexyl acrylate are 1-10 Alkyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ] (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate; Tricyclo[5.2.1.0 2,6](meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl(meth)acrylate; Preferred are (meth)acrylic acid esters having an aromatic ring, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate.

[0114] Vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (also called 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxy ethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6- Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 ]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, and other bicyclounsaturated compounds. Examples of vinyl monomers having an unsaturated heterocycle include dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide. Examples of vinyl monomers having an aromatic ring include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene. Other vinyl monomers include nitrile group-containing monomers such as acrylonitrile and methacrylonitrile; Halogen atom-containing monomers such as vinyl chloride and vinylidene chloride; Examples include acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these vinyl monomers, from the viewpoints of copolymerization reactivity and heat resistance, styrene-based monomers such as styrene and vinyltoluene, dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide and N-benzylmaleimide, and bicyclounsaturated compounds such as bicyclo[2.2.1]hept-2-ene (also called 2-norbornene) are preferred.

[0115] The structural unit obtained by adding (b) to a structural unit derived from (a) refers to a unit formed by adding (b) to a structural unit derived from (a) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (b). In this structural unit, (a) may be any of the above-mentioned examples, and (b) may also be any of the above-mentioned examples. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred.

[0116] The structural unit obtained by adding (a) to a structural unit derived from (b) refers to a unit formed by adding (a) to a structural unit derived from (b) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0117] A structural unit obtained by adding (a) to a structural unit derived from (b) and then further adding a carboxylic acid anhydride refers to a structural unit in which (a) is added to a structural unit derived from (b) constituting the main chain of the copolymer, resulting in the formation of a hydroxyl group, to which a carboxylic acid anhydride is attached through half-esterification. This structural unit has a pendant carboxy group derived from the carboxylic acid anhydride and a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. Examples of carboxylic acid anhydrides include saturated aliphatic polycarboxylic acid anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; and alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0118] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: It is also preferable that the structural unit derived from (c) is not substantially contained. The total of the structural units derived from (a) and the structural units derived from (b) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K1]. When the ratio of the structural units of the resin [K1] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

[0119] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0120] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer, such as the solvent described below as the solvent (E) for the colored resin composition of the present invention.

[0121] The obtained copolymer may be used as a solution after the reaction as it is, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) extracted by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for preparing the colored resin composition of the present invention, and therefore the manufacturing process of the colored resin composition of the present invention can be simplified.

[0122] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 1 to 70 mol% Structural units derived from (b): 1 to 60 mol% Structural units derived from (c): 20 to 95 mol% Preferably, Structural units derived from (a): 3 to 50 mol% Structural units derived from (b): 3 to 40 mol% Structural units derived from (c): 30 to 90 mol% It is more preferable that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 30 mol% Structural units derived from (c): 40 to 80 mol% It is even more preferable that: The total of the structural units derived from (a), the structural units derived from (b), and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K2]. When the ratio of the structural units of the resin [K2] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and the obtained color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

[0123] In the resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (b) is preferably a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond, and more preferably a monomer (b1-2) having an epoxidized alicyclic unsaturated hydrocarbon. (c) is preferably a (meth)acrylic acid ester having a cyclic unsaturated aliphatic hydrocarbon group, a (meth)acrylic acid ester having an aromatic ring, or a dicarbonyl imide derivative.

[0124] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0125] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that Structural units derived from (a): 35 to 45 mol% Structural units derived from (c): 55 to 65 mol% It is even more preferable that: It is also preferable that the polymer contains substantially no structural units derived from (b). The total of the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all structural units constituting the resin [K3].

[0126] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid, and (c) is preferably a (meth)acrylic acid ester having an aromatic ring. Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0127] In the resin [K4], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a) (without addition of (b)): 1 to 60 mol% Structural units in which (b) is added to structural units derived from (a): 1 to 50 mol% Structural units derived from (c): 30 to 90 mol% Preferably, Structural units derived from (a) (without addition of (b)): 5 to 50 mol% Structural units in which (b) is added to structural units derived from (a): 5 to 40 mol% Structural units derived from (c): 35 to 80 mol% It is more preferable that Structural units derived from (a) (without addition of (b)): 10 to 40 mol% Structural units in which (b) is added to structural units derived from (a): 10 to 25 mol% Structural units derived from (c): 40 to 75 mol% It is even more preferable that: The total of the structural units derived from (a) (without the addition of (b)), the structural units derived from (a) with the addition of (b), and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4].

[0128] The structural unit derived from (a) (without the addition of (b)) is preferably a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit obtained by adding (b) to a structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, bicyclounsaturated compounds, and styrene-based monomers, more preferably two or more. When (c) has two types of structural units derived from (c), it is preferable that two types are selected from unsaturated carboxylic acid esters such as (meth)acrylic acid esters, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring, and that two or more types are selected from bicyclounsaturated compounds and vinyl monomers such as styrene-based monomers.

[0129] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0130] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0131] In the resin [K4'], the ratio of the structural units derived from each of these is as follows, among all the structural units constituting the resin [K4']: Structural units in which (b) is added to structural units derived from (a): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units obtained by adding (b) to structural units derived from (a): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units obtained by adding (b) to structural units derived from (a): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferable that: Furthermore, structural units derived from (a) to which (b) is not added are not substantially included. The total of the structural units obtained by adding (b) to the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4'].

[0132] The structural unit obtained by adding (b) to a structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more selected from these. The resin [K4'] may be produced by referring to the production method of the resin [K4] described above, and the amount of (b) used is preferably 100 mol per 100 mol of (a).

[0133] In resin [K5], the ratio of structural units derived from each of these is as follows among all structural units constituting resin [K5]: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units in which (a) is added to structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units in which (a) is added to structural units derived from (b): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units in which (a) is added to structural units derived from (b): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferable that: The total of the structural units derived from (b) (without (a) added), the structural units derived from (b) with (a) added, and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K5].

[0134] The structural unit derived from (b) (without (a) added) is preferably a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized. The structural unit in which (a) has been added to a structural unit derived from (b) is preferably a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more selected from these.

[0135] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0136] Furthermore, under the same conditions as in the production method of resin [K4] or resin [K4'], resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 100 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0137] In the resin [K6], the ratio of structural units derived from each of these is as follows: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added): 20 to 85 mol% Structural units obtained by adding (a) to structural units derived from (b) and then adding a carboxylic acid anhydride thereto: 2 to 40 mol% Structural units derived from (c): 10 to 60 mol% Preferably, Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 40 to 80 mol% Structural units obtained by adding (a) to a structural unit derived from (b) and then adding a carboxylic acid anhydride thereto: 3 to 30 mol% Structural units derived from (c): 15 to 50 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 50 to 70 mol% Structural units obtained by adding (a) to structural units derived from (b) and then adding a carboxylic acid anhydride thereto: 5 to 20 mol% Structural units derived from (c): 20 to 40 mol% It is even more preferable that:

[0138] The total of the structural units derived from (b) (to which (a) is not added), the structural units in which (a) is added to the structural units derived from (b) (to which carboxylic acid anhydride is not added), the structural units in which (a) is added to the structural units derived from (b) and then a carboxylic acid anhydride is added, and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K6].

[0139] As the structural unit derived from (b) (without (a) added), a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred. As the structural unit in which (a) has been added to a structural unit derived from (b) (without carboxylic acid anhydride added), a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred. As the structural unit in which (a) has been added to a structural unit derived from (b) and a carboxylic acid anhydride has been further added, a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred, The structural unit derived from (c) is preferably one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and more preferably two or more types.

[0140] Resin [K6] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0141] Furthermore, under the same conditions as in the production of resin [K4], the cyclic ether derived from (b) contained in the copolymer of (b) and (c) is reacted with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0142] The hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic acid anhydride contained in (a) is reacted with the carboxylic acid anhydride. The amount of the carboxylic acid anhydride used is preferably 0.05 to 1 mol, more preferably 0.10 to 0.8 mol, and even more preferably 0.13 to 0.7 mol, per 1 mol of the amount of (a) used (in other words, per 1 mol of the hydroxyl group generated by the use of (a)).

[0143] 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 acrylate / (meth)acrylic acid copolymer and other resins [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / tricyclo[5.2.1.0 2,6 ]decene-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / phenoxybenzyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, and other resins [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; Resins such as a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer [K4]; Resins such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / (meth)acrylic acid with glycidyl (meth)acrylate, and a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid with glycidyl (meth)acrylate [K4']; Resins such as resins obtained by reacting tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymers with (meth)acrylic acid, and resins obtained by reacting tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymers with (meth)acrylic acid [K5]; Examples of such resins include a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with tetrahydrophthalic anhydride, a resin obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate, tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with succinic anhydride, and a resin obtained by reacting a copolymer of methyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with succinic anhydride [K6].

[0144] Resin (B) is preferably a copolymer (resin [K1] or resin [K2]) containing a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and more preferably resin [K2].

[0145] The polystyrene-equivalent weight average molecular weight of 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 the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the colored pattern tends to be improved. The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0146] The acid value of the resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 25 to 150 mg-KOH / g, and even more preferably 30 to 135 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0147] The content of resin (B) is preferably 2 to 65 mass%, more preferably 5 to 60 mass%, and even more preferably 10 to 55 mass%, based on the total amount of solids in the colored resin composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0148] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0149] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

[0150] Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0151] Among these, 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 poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tri(meth)acrylate ... pentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylates (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylates (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated pentaerythritol tri(meth)acrylate), alkoxylated dipentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylates (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol caprolactone-modified pentaerythritol poly(meth)acrylates (for example, caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylates (for example, caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), and the like. Among these, it is preferable to include at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate, and it is more preferable to include at least one selected from the group consisting of trimethylolpropane triacrylate and dipentaerythritol polyacrylate.

[0152] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, even more preferably 100 or more and 3,000 or less, still more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0153] The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 7% by mass or more and 70% by mass or less, and even more preferably 10% by mass or more and 50% by mass or less, relative to the total amount of solids in the colored resin composition.

[0154] <Polymerization initiator (D)> The polymerization initiator (D) may be any compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization.

[0155] Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0156] The O-acyloxime compound is a compound having a partial structure represented by formula (d-1): In the formula, * represents a bond.

[0157] [ka]

[0158] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl)-2-methylbenzoyl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl) ...

[0033] N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and the like. Commercially available products such as Irgacure OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine), Irgacure OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine) (all manufactured by BASF), N-1919 (manufactured by ADEKA), and TR-PBG327 (N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine) (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, the O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, and N-benzoyloxy- At least one selected from the group consisting of 1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferred, with N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine being more preferred. These O-acyloxime compounds tend to produce color filters with high brightness.

[0159] The alkylphenone compound is a compound having a partial structure represented by formula (d-2) or a partial structure represented by formula (d-3). In these partial structures, the benzene ring may have a substituent. In the formula, * represents a bond.

[0160] [ka]

[0161] Examples of compounds having a partial structure represented by formula (d-2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.

[0162] Examples of compounds having a partial structure represented by formula (d-3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d-2).

[0163] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0164] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0165] 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, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, ... Examples of suitable biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913). Among these, compounds represented by the following formula and mixtures thereof are preferred:

[0166] [ka]

[0167] Further 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'-tetra(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 are preferably used in combination with the polymerization initiator aid (D1) (particularly an amine compound) described below.

[0168] Examples of the polymerization initiator that generates an acid 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 tosylates; and benzoin tosylates.

[0169] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, more preferably a polymerization initiator containing an O-acyloxime compound and / or a biimidazole compound, and even more preferably a polymerization initiator containing an O-acyloxime compound.

[0170] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, 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 the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0171] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D). When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0172] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0173] 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, and preferably 4,4'-bis(diethylamino)benzophenone. Alternatively, commercially available amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0174] 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.

[0175] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0176] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0177] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of all resins (B) and polymerizable compounds (C) contained in the colored resin composition.

[0178] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule but not -O-), ether solvents (solvents containing -O- in the molecule but not -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not -COO-), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

[0179] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0180] 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, phenetole, and methylanisole.

[0181] Ether ester solvents 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, and 2-ethoxy-2-methylpropionate. ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0182] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0183] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0184] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0185] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0186] As the solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and cyclohexanone are preferred, and propylene glycol monomethyl ether acetate and propylene glycol monomethyl ether are more preferred.

[0187] When the solvent (E) is contained, the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 97% by mass or less, even more preferably 70% by mass or more and 96% by mass or less, and even more preferably 73% by mass or more and 95% by mass or less, based on the total amount of the colored resin composition. In other words, the total amount of solids in the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 50% by mass or less, even more preferably 4% by mass or more and 30% by mass or less, and even more preferably 5% by mass or more and 27% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and when a color filter is formed, the color density is not insufficient, so the display characteristics tend to be good.

[0188] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain.

[0189] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as polyether-modified silicone oils. Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0190] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0191] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0192] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, relative to the total amount of the colored resin composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0193] <Other ingredients> The colored resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0194] <Method of producing colored resin composition> The colored resin composition can be prepared by mixing the colorant (A), the resin (B), and optionally the polymerizable compound (C), the polymerization initiator (D), the polymerization initiator aid (D1), the solvent (E), the leveling agent (F), and other components. Mixing can be carried out using known or conventional equipment and conditions. The colorant (A) may be mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less, and used as a colorant-containing liquid. In this case, it is preferable to use it as a colorant-containing liquid. In this case, the dispersant and part or all of the resin (B) may be blended as necessary. The remaining components are mixed with the colorant-containing liquid obtained in this manner to achieve the desired concentration, thereby preparing the desired colored resin composition. When a dye is contained as the colorant (A), the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution, which is then preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0195] <Color filter> Methods for producing a colored pattern of a color filter from the colored resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.

[0196] The film thickness of the color filter (cured film) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, still more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, and preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0197] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass; a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate; silicon; or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS may be used.

[0198] Formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored resin composition is applied to a substrate, and then the composition is dried by heating and drying (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents and obtain a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. When drying by heating, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably carried out under a pressure of 50 to 150 Pa and at a temperature of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the desired color filter.

[0199] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 250 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, or 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.

[0200] A colored pattern is formed on the substrate by bringing the exposed composition layer into contact with a developer and developing it. The unexposed portions of the composition layer are dissolved and removed by development. 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 also contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, or the like. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0201] Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-bake time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0202] The colored patterns and colored coating films thus obtained are useful as color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. [Example]

[0203] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and can of course be practiced with appropriate modifications within the scope of the above and below-described aims, all of which are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

[0204] In the following examples, the structures of the compounds were confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.).

[0205] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0206] Compound Synthesis Example 1 (Example) <Synthesis of Compound (III-1)> Under a nitrogen atmosphere, 1.5 parts of gallium chloride (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.9 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 11 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 140°C, and stirred for 16 hours. After the reaction solution was cooled to room temperature, 63 parts of ethyl acetate was added and stirred for 30 minutes. The resulting precipitate was collected as a residue by suction filtration and washed with 120 parts of ethyl acetate. The resulting residue and 63 parts of ion-exchanged water were mixed at room temperature, stirred for 30 minutes, and then washed with 75 parts of ion-exchanged water. The resulting residue was dried under reduced pressure at 60°C to obtain 3.4 parts of a compound represented by formula (III-1) (hereinafter, compound (III-1)).

[0207] [ka]

[0208] <Identification of Compound (III-1)> (mass spectrometry) Ionization mode = MALDI-TOF - : m / z=[M] - 616 Exact Mass: 616

[0209] <Preparation of Compound (IV-1)> A compound represented by the following formula (IV-1) (hereinafter, compound (IV-1)) was obtained in the same manner as in the synthesis of the compound represented by formula (8) described in Example 4 of WO 2022 / 024926.

[0210] [ka]

[0211] <Synthesis of compound (IA-153 Ga)> 1.8 parts of compound (III-1), 1.2 parts of compound (IV-1), and 9.0 parts of propylene glycol monomethyl ether acetate (Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C, and stirred for 9 hours. After the reaction solution was cooled to room temperature, 90 parts of ethyl acetate was added. The resulting precipitate was collected as a residue by suction filtration and washed with ethyl acetate. 90 parts of ethyl acetate was added to the resulting residue and stirred, and then the residue was filtered and washed with ethyl acetate. The resulting residue was dried under reduced pressure while heating at 60°C, to obtain 2.4 parts of a compound represented by formula (IA-153 Ga) (hereinafter, compound (IA-153 Ga)).

[0212] [ka]

[0213] <Identification of compound (IA-153 Ga)> (mass spectrometry) Ionization mode = MALDI-TOF - : m / z=[M] - 782 Exact Mass: 782

[0214] Comparative Compound Synthesis Example 1 A compound represented by formula (IA-153 Al) (hereinafter, compound (IA-153 Al)) was obtained in accordance with the synthesis method described in Example 4 of WO 2022 / 024926.

[0215] [ka]

[0216] Resin synthesis example 1 <Preparation of Resin (B-1)> A suitable amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C with stirring. Next, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 54 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator dissolved in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition of the initiator solution was completed, the mixture was kept at 80°C for 3 hours and then cooled to room temperature. A copolymer (resin (B-1)) solution with a viscosity of 127 mPas measured with a Brookfield viscometer (23°C) and a solids content of 37.0% was obtained. The weight-average molecular weight Mw of the resulting copolymer was 9.4 x 10 3 The resin (B-1) had the following structural units: a polydispersity of 1.89, and an acid value calculated as solid content of 114 mg-KOH / g.

[0217] [ka]

[0218] Dispersion liquid preparation example 1 Five parts of compound (IA-153 Ga), 3 parts of dispersant (BYK BYKLPN-6919) (solids content equivalent), 3 parts of resin (B-1) (solids content equivalent), and 89 parts of propylene glycol monomethyl ether acetate were mixed, to which 300 parts of 0.2 μm zirconia beads were added, and the mixture was shaken for 0.5 hours using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion (A-1).

[0219] Comparative dispersion preparation example 1 A comparative dispersion (Ax) was obtained in the same manner as in Dispersion Preparation Example 1, except that the compound (IA-153 Ga) was changed to the compound (IA-153 Al).

[0220] Colored resin composition preparation example 1 Colored resin composition 1 was obtained by mixing the following components. Dispersion (A-1) 415 parts Resin (B-1) (solid content equivalent) 48 parts Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Trade name A-9550: Manufactured by Shin-Nakamura Chemical Co., Ltd. 20 parts Polymerizable compound (C-2): Trimethylolpropane triacrylate: Trade name A-TMPT: Manufactured by Shin-Nakamura Chemical Co., Ltd. 20 parts Polymerization initiator (D): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine: Trade name PBG-327: O-acyloxime compound; Manufactured by Changzhou Strong Electronic New Materials Co., Ltd. 5 parts Solvent (E): Propylene glycol monomethyl ether acetate 645 parts Leveling agent (F): Polyether-modified silicone oil: Trade name Toray Silicone SH8400: Manufactured by Toray Dow Corning Co., Ltd. 0.1 parts

[0221] Comparative colored resin composition preparation example 1 Comparative colored resin composition 1 was obtained in the same manner as in Colored Resin Composition Preparation Example 1, except that the dispersion (A-1) was changed to the comparative dispersion (Ax).

[0222] Paint film formation example 1, comparative paint film formation example 1 Colored resin composition 1 (in the case of Coating Film Formation Example 1) or comparative colored resin composition 1 (in the case of Comparative Coating Film Formation Example 1) was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated), and then prebaked at 100°C for 2 minutes to obtain a coating film. Thereafter, the prebaked coating film was postbaked at 230°C for 5 minutes. The thickness of the coating film in Coating Film Formation Example 1 was 640 nm, and the thickness of the coating film in Comparative Coating Film Formation Example 1 was 820 nm.

[0223] (1) Heat resistance test (absorbance retention rate) The post-baked coating film was heated in an oven under atmospheric conditions at 260°C for 10 minutes. The absorbance retention rate was measured for each coating film before and after heating using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) in a wavelength range of 380 nm to 780 nm at 1 nm intervals. Here, the absorbance retention rate is a numerical value calculated using the following formula, and a higher absorbance retention rate indicates better heat resistance. Furthermore, if the heat resistance of the coating film is good, it can be said that a color filter made from the same colored resin composition also has excellent heat resistance. The results are shown in Table 6. Absorbance retention rate (%) = (absorbance at the maximum absorption wavelength of the coating film after heating (if there are two or more maximum absorption wavelengths, the wavelength with the greatest absorbance)) / (absorbance at the maximum absorption wavelength of the coating film before heating (if there are two or more maximum absorption wavelengths, the wavelength with the greatest absorbance)) x 100

[0224] [Table 6]

[0225] (2) Spectral evaluation The post-baked coating film was subjected to spectral measurement in the wavelength range of 380 nm to 780 nm at 1 nm intervals using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). The maximum absorption wavelength λ in the obtained spectral data was max The absorbance at the wavelength (when there are two or more maximum absorption wavelengths, the wavelength at which the absorbance is greatest) was normalized to 2.0 to eliminate film thickness dependency.max The λ of the coating film in Comparative Coating Film Formation Example 1 is 690 nm. max was 675 nm.

[0226] (2.1) Color separation Based on the normalized spectral data described above, the absorbance at the maximum absorption wavelength was calculated as Abs(λ max )(=2.0), maximum absorption wavelength λ max The absorbance on the 45 nm short wave side is Abs(λ max-45 ) and calculated the respective values, and the color separation was calculated based on the following formula. Color separation = Abs(λ max-45 ) / Abs(λ max ) The results are shown in Table 7. The closer this value is to 1, the easier it is to improve color separation (color purity) in the visible region, reducing sensor signal noise and providing favorable color filter characteristics.

[0227] [Table 7]

[0228] (2.2) Color characteristics Based on the normalized spectral data described above, the absorbance Abs (λ max (=2.0) and the absorbance at a wavelength of 500 nm (Abs(λ 500 )) and absorbance at a wavelength of 600 nm (Abs(λ 600 )) and absorbance at a wavelength of 730 nm (Abs(λ 730 )) were calculated, and color characteristics 1 to 3 were determined based on the following formulas. Color property 1 = Abs(λ 500 ) / Abs(λ max ) Color property 2 = Abs(λ 600 ) / Abs(λ max ) Color property 3 = Abs(λ 730 ) / Abs(λ max ) In Coating Film Formation Example 1, the results were Color Property 1: 0.01, Color Property 2: 0.24, and Color Property 3: 0.28. Therefore, it is clear that the compound used in Coating Film Formation Example 1 is suitable as a colorant for producing green or cyan color filters.

Claims

1. A compound represented by formula (I): 【Chemical 1】 [In formula (I), M １ represents Ga or In. R １ represents an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, R ２ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or Z ２ and R １ represents a single bond connecting Z １ and Z ２ each independently represents a single bond or an oxygen atom. X １ ~X ４ are each independently -R ３ , -OR ３ , -SR ３ , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R ３ represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. n1 to n4 each independently represent an integer of 0 to 4.]

2. A colored resin composition comprising the compound according to claim 1 and a resin.

3. The colored resin composition according to claim 2, further comprising a polymerizable compound and a polymerization initiator.

4. A color filter formed from the colored resin composition according to claim 2 or 3.

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

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