Compounds, colored resin compositions, color filters, display devices, and solid-state image sensors

Abstract

An object of the present invention is to provide a compound having excellent heat resistance. 【Solution means】The above problem can be solved by a compound represented by the following formula (I). TIFF2026081544000021.tif6595 [In the formula, A 1 ~A 4 each independently represents a cyano group, a nitro group, a C(O)R x group, a C(O)OR x group, a S(O)R x group and the like. R 1 and R 2 each independently represents a substituted / unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a substituted / unsubstituted heterocyclic group.]

Description

[Technical Field]

[0001] The present invention relates to a compound useful as a coloring agent, a colored resin composition containing the compound, a color filter formed from the colored resin composition, and a display device and a solid-state image sensor including the color filter. [Background technology]

[0002] As an example of isoindoline dye, the isoindoline dye disclosed in Patent Document 1 is known. When a coloring agent such as an isoindoline dye is used in a manufacturing process that includes high temperatures (for example, the manufacture of color filters), the coloring agent is required to have good heat resistance. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2018-168362 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, conventional isoindoline dyes, such as those described in Patent Document 1, did not provide satisfactory heat resistance. Therefore, the object of the present invention is to provide a compound with excellent heat resistance. [Means for solving the problem]

[0005] The gist of this invention is as follows: [1] A compound represented by formula (I). [ka] [In formula (I), A 1 ~A 4 These are, independently of each other, a cyano group, a nitro group, and C(O)R xGroup, C(O)OR x Group, S(O)R x Group, S(O)OR x Group, or S(O)2OR x represents a group. R 1 and R 2 each independently represent an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms or an optionally substituted heterocyclic group. R 3 and R 4 each independently represent an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted heterocyclic group, or a hydrogen atom. R a 、R b and R c each independently represent an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted heterocyclic group, a halogen atom, a cyano group, a nitro group, a formyl group, C(O)R x group, C(O)OR x group, C(O)OH group, S(O)R x group, S(O)OR x group, S(O)2R x group, S(O)2OR x group, S(O)2OH group, NR x 2 group, or NHR x group, and when there are a plurality of R a they may be the same or different from each other, and when there are a plurality of R b they may be the same or different from each other, and when there are a plurality of R c they may be the same or different from each other. a, b, and c each independently represent an integer of any one of 0 to 4. R x represents a hydrocarbon group having 1 to 10 carbon atoms, and when there are a plurality of R x they may be the same or different from each other. The wavy line indicates that an E isomer, a Z isomer, or a mixture thereof is included.] [2] A 1 ~A 4 is a cyano group, the compound according to [1]. [3] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains the compound described in [1] or [2]. [4] The colored resin composition according to [3] further comprising a polymerizable compound and a polymerization initiator. A color filter formed from the colored resin composition described in [5] [3] or [4]. A display device including the color filter described in [6] [5]. [7] A solid-state image sensor including the color filter described in [5]. [Effects of the Invention]

[0006] According to the present invention, a compound with excellent heat resistance can be provided. This compound is useful in colored resin compositions, color filters, display devices, etc., and a colored resin composition containing this compound can be used to form a color filter with excellent heat resistance. [Modes for carrying out the invention]

[0007] <Compound (I)> The compound according to the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)). The present invention will be described in detail below using formula (I), but compound (I) also includes tautomers of formula (I). Compound (I) according to the present invention has excellent heat resistance, and according to compound (I), good heat resistance can be achieved in color filters formed from a colored resin composition containing compound (I). Preferably, compound (I) according to the present invention can be suitably used in green color filters.

[0008] [ka] [In formula (I), A 1 ~A 4 These are, independently of each other, a cyano group, a nitro group, and C(O)R x Base, C(O)OR x group, S(O)R x Base, S(O)ORx Base, or S(O)2OR x It represents the base. R 1 and R 2 Each of these independently represents an aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have substituents, or a heterocyclic group, which may have substituents. R 3 and R 4 Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents, a heterocyclic group, which may have substituents, or a hydrogen atom. R a , R b and R c These are, independently of each other, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, a heterocyclic group which may have substituents, a halogen atom, a cyano group, a nitro group, a formyl group, and C(O)R x Base, C(O)OR x group, C(O)OH group, S(O)R x Base, S(O)OR x Base, S(O)2R x group, S(O)2OR x group, S(O)2OH group, NR x 2 units, or NHR x Represents the base, R a If there are multiple, they may be the same or different from each other, R b If there are multiple, they may be the same or different from each other, R c If there are multiple instances, they may be the same or different from one another. a, b, and c represent integers from 0 to 4, independently of each other. R x R represents a hydrocarbon group with 1 to 10 carbon atoms. x If there are multiple instances, they may be the same or different from one another. The wavy line indicates that the E-form, Z-form, or a mixture thereof is included.

[0009] R 3 , R 4 , R a , R b and R cExamples of hydrocarbon groups having 1 to 20 carbon atoms represented by include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups may be saturated or unsaturated, and may be linear or alicyclic.

[0010] The saturated or unsaturated linear hydrocarbon groups include linear alkyl groups such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, and n-icosyl group; isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, and (2-methyl)pentyl group. Examples include branched alkyl groups such as (1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, and (2-ethyl)octyl group; and alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, and 2-pentenyl group.

[0011] Examples of the saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl, and cyclooctenyl groups; and norbornyl, adamantyl, and bicyclo[2.2.2]octyl groups.

[0012] Examples of the aromatic hydrocarbon groups include aryl groups such as phenyl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, and biphenyl group; alkylaryl groups such as 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, 2,4,6-trimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2-methyl-6-isopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, and p-tert-butylphenyl group; and alkenylaryl groups such as 4-vinylphenyl group.

[0013] The aforementioned hydrocarbon groups having 1 to 20 carbon atoms may be groups that combine two or more selected from the group consisting of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 20. Such groups include, for example, aralkyl groups such as benzyl group, phenethyl group, and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, and 3,4-dimethylcyclohexyl group. Examples include alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded, such as 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, and 3,3,5,5-tetramethylcyclohexyl group; alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, and cyclohexylethyl group; and so on.

[0014] R 3 , R 4 , R a , R b and R c The number of carbon atoms in the saturated chain hydrocarbon group (i.e., linear alkyl group, branched alkyl group) represented by is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. R 3 , R 4 , R a , R b and Rc The number of carbon atoms of the unsaturated chain hydrocarbon group (i.e., alkenyl group, alkynyl group) represented by is preferably 2 to 12, more preferably 2 to 8, and still more preferably 2 to 5. R 3 、R 4 、R a 、R b 及びR c The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group represented by is preferably 3 to 10, more preferably 3 to 6. R 3 、R 4 、R a 、R b 及びR c The number of carbon atoms of the aromatic hydrocarbon group represented by is preferably 6 to 15, more preferably 6 to 10, and still more preferably 6 to 8. R 3 、R 4 、R a 、R b 及びR c The number of carbon atoms of the group formed by combining two or more selected from the group consisting of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group represented by is preferably 7 to 18, more preferably 7 to 15.

[0015] R 1 及びR 2 Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a xylyl group (e.g., 3,5-xylyl group, 2,6-xylyl group, etc.), a 4-n-butylphenyl group, a 4-tert-butylphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a phenylphenyl group, a triphenylphenyl group, etc. R 1 及びR 2 The number of carbon atoms of the aromatic hydrocarbon group represented by is preferably 6 to 14, more preferably 6 to 12.

[0016] R 1 、R 2 、R 3 、R 4 、R a, R b and R c Examples of the heterocyclic group represented by b and c include groups obtained by removing one arbitrary hydrogen atom contained in the heterocycle. The heterocycle may be a monocyclic or polycyclic ring, and is preferably a heterocycle containing a heteroatom as a ring component. Examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, etc. The carbon number of the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, still more preferably 3 to 20, even more preferably 3 to 18, and even more preferably 3 to 15.

[0017] Examples of the heterocycle containing only a nitrogen atom as a heteroatom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, piperazine; 5-membered ring unsaturated heterocycles such as pyrrole such as 2,5-dimethylpyrrole, pyrazole such as 2-methylpyrazole, 3-methylpyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole; 6-membered ring unsaturated heterocycles such as pyridine, pyridazine, pyrimidine such as 6-methylpyrimidine, pyrazine, 1,3,5-triazine; condensed bicyclic heterocycles such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline such as 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine; condensed tricyclic heterocycles such as carbazole, acridine, phenazine; etc.

[0018] Heterocycles containing only an oxygen atom as a heteroatom include monocyclic saturated heterocycles such as oxiranes, oxetanes, tetrahydrofurans, tetrahydropyrans, 1,3-dioxanes, 1,4-dioxanes, and 1-cyclopentyldioxolanes; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decanes and 1,4-dioxaspiro[4.5]nonanes; and α-acetolactones, β-propiolactones, and γ-butyrolactones. Examples include lactone heterocycles such as δ-valerolactone; five-membered unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; six-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; condensed bicyclic heterocycles such as benzopyrans such as 1-benzofuran and 4-methylbenzopyran, benzodioxol, chroman, and isochroman; and condensed tricyclic heterocycles such as xanthenes and dibenzofuran.

[0019] Examples of heterocycles containing only a sulfur atom as a heteroatom include five-membered saturated heterocycles such as dithiolanes; six-membered saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl-1,3-dithiane; five-membered unsaturated heterocycles such as thiophenes such as 3-methylthiophene and 2-carboxythiophene, and benzothiopyrans such as 4H-thiopyran and benzotetrahydrothiopyran; condensed bicyclic heterocycles such as benzothiophene; and condensed tricyclic heterocycles such as thiantrene and dibenzothiophene.

[0020] Examples of heterocycles containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, and 2-methyl-2-piperidone; monocyclic unsaturated heterocycles such as oxazoles such as 4-methyloxazole and isoxazoles such as 2-methylisoxazole and 3-methylisoxazole; condensed bicyclic heterocycles such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazoline; and condensed tricyclic heterocycles such as phenoxazine.

[0021] Examples of heterocycles containing nitrogen and sulfur atoms as heteroatoms include monocyclic heterocycles such as thiazoles like 3-methylthiazole and 2,4-dimethylthiazole; condensed bicyclic heterocycles such as benzothiazole; and condensed tricyclic heterocycles such as phenothiazine.

[0022] The heterocyclic group mentioned above may be a group formed by combining the hydrocarbon groups listed above, for example, a tetrahydrofurylmethyl group, a methyltetrahydrofuryl group, and the like.

[0023] R 3 , R 4 , R a , R b and R c A hydrocarbon group represented by R 1 and R 2 Aromatic hydrocarbon groups represented by R 1 , R 2 , R 3 , R 4 , R a , R b and R c The substituents that the heterocyclic group represented by may have include, for example, a halogen atom, a cyano group, a nitro group, a formyl group, OR x group, OH group, C(O)R x Base, C(O)OR x group, C(O)OH group, C(O)NR x 2 units, C(O)NHR x Base, SR x group, S(O)R x Base, S(O)OR x group, S(O)OH group, S(O)2R x group, S(O)2NR x 2 units, S(O)2NHR x group, S(O)2OR x group, S(O)2OH group, NR x 2 units, NHR x group, NH2 group, NR x C(O)R x Examples include the base (however, R x The same applies as above, R x If there are multiple instances, they may be the same or different from one another.

[0024] R x Examples of hydrocarbon groups having 1 to 10 carbon atoms represented by include those groups having 1 to 10 carbon atoms from among the examples of hydrocarbon groups having 1 to 20 carbon atoms mentioned above, with hydrocarbon groups having 1 to 5 carbon atoms being preferred, chain-like hydrocarbon groups having 1 to 5 carbon atoms being more preferred, and saturated chain-like hydrocarbon groups having 1 to 5 carbon atoms being even more preferred.

[0025] R a , R b and R c Examples of halogen atoms represented by and the halogen atoms as substituents include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc., with fluorine atoms, chlorine atoms, and bromine atoms being preferred.

[0026] OR as the substituent mentioned above x Examples of groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, and phenoxy groups.

[0027] A 1 ~A 4 , R a , R b and R c C(O)R represented by x The group, and C(O)R as the substituent mentioned above. x Examples of groups include acetyl groups, propanoyl groups, butanoyl groups, pivaloyl groups, and benzoyl groups.

[0028] A 1 ~A 4 , R a , R b and R c C(O)OR x The group, and the above substituent C(O)OR x Examples of carbonyl groups include methoxycarbonyl groups, ethoxycarbonyl groups, propoxycarbonyl groups, butoxycarbonyl groups, hexyloxycarbonyl groups, and phenoxycarbonyl groups.

[0029] C(O)NR as the substituent mentioned above xExamples of the two groups include N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-bis(1-methylpropyl)carbamoyl group, and N,N-diphenylcarbamoyl group.

[0030] C(O)NHR as the substituent mentioned above x Examples of these groups include N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-butylcarbamoyl group, N-hexylcarbamoyl group, and N-phenylcarbamoyl group.

[0031] SR as the above substituent x Examples of groups include methylsulfanyl group, ethylsulfanyl group, butylsulfanyl group, hexylsulfanyl group, and phenylsulfanyl group.

[0032] A 1 ~A 4 , R a , R b and R c S(O)R represented by x The group, and S(O)R as the substituent mentioned above. x Examples of the groups include methyl sulfinyl group, ethyl sulfinyl group, propyl sulfinyl group, butyl sulfinyl group, and phenyl sulfinyl group.

[0033] A 1 ~A 4 , R a , R b and R c S(O)OR, represented as x The group, and the above substituent S(O)OR x Examples of these groups include methoxysulfinyl groups, ethoxysulfinyl groups, propoxysulfinyl groups, and phenoxysulfinyl groups.

[0034] R a , R b and R c S(O)2R, represented as xThe group, and S(O)2R as the substituent mentioned above. x Examples of these groups include methylsulfonyl groups, ethylsulfonyl groups, propylsulfonyl groups, and phenylsulfonyl groups.

[0035] S(O)2NR as the substituent mentioned above x Examples of the two groups include N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, and N,N-diphenylsulfamoyl group.

[0036] S(O)2NHR as the substituent mentioned above x Examples of these groups include N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-hexylsulfamoyl group, and N-phenylsulfamoyl group.

[0037] A 1 ~A 4 , R a , R b and R c S(O)2OR, represented as x The group, and the above substituent S(O)2OR x Examples of groups include methoxysulfonyl groups, ethoxysulfonyl groups, propoxysulfonyl groups, and phenoxysulfonyl groups.

[0038] R a , R b and R c NR represented by x Two units, and NR as the substituent mentioned above. x Examples of the two groups include dimethylamino group, diethylamino group, dipropylamino group, and diphenylamino group.

[0039] R a , R b and R c NHR represented by x NHR as a group and as a substituent. xExamples of groups include methylamino group, ethylamino group, benzylamino group, and phenylamino group.

[0040] NR as the substituent mentioned above x C(O)R x Examples of the groups include methylcarbonylamino group, ethylcarbonylamino group, propylcarbonylamino group, and phenylcarbonylamino group.

[0041] In terms of being able to form a color filter with good heat resistance and / or color purity, in formula (I), A 1 ~A 4 These are, independently of each other, a cyano group, a nitro group, or C(O)R x The group (the R x Preferably, a hydrocarbon group having 1 to 5 carbon atoms is preferred, a chain hydrocarbon group having 1 to 5 carbon atoms is more preferred, a saturated chain hydrocarbon group having 1 to 5 carbon atoms is even more preferred, an alkyl group having 1 to 3 carbon atoms is even more preferred, a cyano group or a nitro group is more preferred, and a cyano group is even more preferred. R 1 and R 2 Preferably, each of these is an aromatic hydrocarbon group having 6 to 20 carbon atoms that may be substituted, or an aromatic monocyclic heterocyclic group that may be substituted; more preferably, an aromatic hydrocarbon group having 6 to 14 carbon atoms that may be substituted, or an aromatic monocyclic saturated heterocyclic group that may be substituted; even more preferably, an aromatic hydrocarbon group having 6 to 12 carbon atoms that may be substituted; and as the aromatic hydrocarbon group having 6 to 12 carbon atoms, a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 3,5-xylyl group, or a 2,6-xylyl group is preferred, and a phenyl group, an o-tolyl group, an m-tolyl group, or a p-tolyl group is more preferred. R 1 and R 2 The aromatic hydrocarbon group and heterocyclic group represented by are preferably substituents, more preferably 1 to 5 substituents, even more preferably 1 to 3 substituents, even more preferably 1 or 2 substituents, and even more preferably 1 substituent. R1 and R 2 The substituents that the aromatic hydrocarbon group and heterocyclic group represented by may have are preferably an OH group, a C(O)OH group, an S(O)OH group, or an S(O)2OH group, more preferably an OH group or a C(O)OH group, and even more preferably a C(O)OH group. R 3 and R 4 These are preferably hydrocarbon groups having 1 to 20 carbon atoms or hydrogen atoms, which may have substituents; more preferably hydrocarbon groups having 1 to 10 carbon atoms or hydrogen atoms; even more preferably hydrocarbon groups having 1 to 5 carbon atoms or hydrogen atoms; even more preferably saturated chain hydrocarbon groups having 1 to 5 carbon atoms or hydrogen atoms; and even more preferably hydrogen atoms. a, b, and c are preferably integers from 0 to 2, more preferably 0 or 1, and even more preferably 0. R a , R b and R c These are, independently of each other, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, a halogen atom, a cyano group, a nitro group, or C(O)OR x group, C(O)OH group, S(O)2OR x A group or an S(O)2OH group is preferred, and a hydrocarbon group having 1 to 20 carbon atoms, C(O)OR x group, C(O)OH group, S(O)2OR x A group or an S(O)2OH group is more preferred, and a hydrocarbon group having 1 to 10 carbon atoms, a C(O)OH group, or an S(O)2OH group is even more preferred. In formula (I), A 1 ~A 4 , R 1 ~R 4 a~c, and R a ~R c It is preferable that one or more selected from the group consisting of are the above preferred (more preferred, even more preferred, even more preferred, or even more preferred) embodiments, and it is more preferable that four or more are the above preferred (more preferred, even more preferred, even more preferred, or even more preferred) embodiments, and a to c are 0, A 1 ~A 4 and R 1 ~R4 It is even more preferable that the above-mentioned preferred (more preferred, even more preferred, even more preferred, or even more preferred) embodiment is present.

[0042] In formula (I), A 1 and A 4 and are the same base and / or A 2 and A 3 It is preferable that and are the same group, A 1 and A 4 and are the same group, A 2 and A 3 It is more preferable that and are the same group, A 1 ~A 4 It is even more preferable that they are the same group. In formula (I), R 1 and R 2 It is preferable that the two groups are the same. In formula (I), R 3 and R 4 It is preferable that the two groups are the same.

[0043] As for compound (I), in formula (I), A 1 ~A 4 However, cyano group, nitro group, or C(O)R x1 Group(R x1 (represents an alkyl group with 1 to 3 carbon atoms), and R 1 ~R 2 However, R is a phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 3,5-xylyl group, or 2,6-xylyl group having an OH group or C(O)OH group as a substituent, 3 ~R 4 However, a compound in which hydrogen atoms are present and a to c are 0 is preferred. A 1 ~A 4 However, it is a cyano group or a nitro group, R 1 ~R 2 However, R is a phenyl group, o-tolyl group, m-tolyl group, or p-tolyl group having an OH group or a C(O)OH group as a substituent, 3 ~R 4 However, a compound in which hydrogen atoms and a to c are 0 is more preferable. A 1 ~A 4 However, it is a cyano group, R 1 ~R 2 However, R is a phenyl group, o-tolyl group, m-tolyl group, or p-tolyl group having a C(O)OH group as a substituent, 3 ~R 4 However, compounds in which hydrogen atoms are present and a to c are 0 are even more preferred.

[0044] Compound (I) specifically refers to compounds (I-a1) to (I-a44) identified by formula (Ia) below and Table 1. In formula (Ia), the dashed line indicates the presence of the E-isomer, Z-isomer, or mixtures thereof. In Table 1, "aa1" to "aa22" represent the groups represented by formulas (aa1) to (aa22) below, respectively, "CN" represents a cyano group, and "NO2" represents a nitro group.

[0045] [ka]

[0046] [Table 1]

[0047] [ka] [In the formula, * represents a bond.]

[0048] As for compound (I), compounds (I-a1) to (I-a22) are preferred, compounds (I-a1) to (I-a17) are more preferred, compounds (I-a1) to (I-a15) are even more preferred, compounds (I-a1) to (I-a7) are even more preferred, compounds (I-a1) to (I-a5) are even more preferred, and compounds (I-a1) to (I-a3) are even more preferred.

[0049] The method for producing compound (I) is not particularly limited, and it can be produced by appropriately combining known organic synthesis reactions depending on the structure of compound (I). For example, it can be produced by the following method.

[0050] Compound (M-3) is produced by reacting the compound represented by formula (M-1) (hereinafter sometimes referred to as compound (M-1)) with the compound represented by formula (M-2) (hereinafter sometimes referred to as compound (M-2)). Compound (M-4) is produced by reacting the compound represented by formula (M-4) (hereinafter sometimes referred to as compound (M-4)) with the compound represented by formula (M-5) (hereinafter sometimes referred to as compound (M-5)). Compound (M-6) is produced by reacting compound (M-3), compound (M-6), and compound represented by formula (M-7) (hereinafter sometimes referred to as compound (M-7)). Compound (I) can then be produced by reacting compound (M-3), compound (M-6), and compound (M-7) (hereinafter sometimes referred to as compound (M-7)).

[0051] [ka] [In the formula, A 1 ~A 4 , R 1 ~R 4 , R a ~R c a-c have the same meaning as above, and the wavy line indicates that it contains the E-form, Z-form, or a mixture thereof.

[0052] The reaction between compound (M-1) and compound (M-2) is carried out by mixing compound (M-1) and compound (M-2). The amount of compound (M-2) used is typically 0.1 to 10 moles per mole of compound (M-1), with 0.3 to 5 moles being preferred.

[0053] The reaction between compound (M-1) and compound (M-2) may be carried out in the presence of a solvent. The solvent used in the reaction between compound (M-1) and compound (M-2) includes the solvent exemplified as solvent (E) described later, with amide solvents being preferred, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone being more preferred, and N,N-dimethylformamide being even more preferred. The amount of solvent used in the reaction between compound (M-1) and compound (M-2) is usually 0.1 to 1000 parts by mass, preferably 0.5 to 100 parts by mass, per 1 part by mass of compound (M-1).

[0054] The reaction time between compound (M-1) and compound (M-2) is typically 0.01 hours to 100 hours, with 0.5 hours to 80 hours being preferred. The reaction temperature between compound (M-1) and compound (M-2) is typically -100°C to 200°C, preferably 0°C to 100°C, and more preferably 20°C to 90°C.

[0055] The reaction between compound (M-4) and compound (M-5) is carried out by mixing compound (M-4) and compound (M-5). The amount of compound (M-5) used is typically 0.1 to 10 moles per mole of compound (M-4), with 0.3 to 5 moles being preferred.

[0056] The reaction between compound (M-4) and compound (M-5) may be carried out in the presence of a solvent. The solvent used in the reaction between compound (M-4) and compound (M-5) includes the solvent exemplified as solvent (E) described later, with amide solvents being preferred, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone being more preferred, and N,N-dimethylformamide being even more preferred. The amount of solvent used in the reaction between compound (M-4) and compound (M-5) is usually 0.1 to 1000 parts by mass, preferably 0.5 to 100 parts by mass, per 1 part by mass of compound (M-4).

[0057] The reaction time between compound (M-4) and compound (M-5) is typically 0.01 hours to 100 hours, with 0.5 hours to 80 hours being preferred. The reaction temperature between compound (M-4) and compound (M-5) is typically -100°C to 200°C, preferably 0°C to 100°C, and more preferably 20°C to 90°C.

[0058] The reaction between compound (M-3), compound (M-6), and compound (M-7) is carried out by mixing compound (M-3), compound (M-6), and compound (M-7). The ratio (molar ratio) of compound (M-3) to compound (M-6) is preferably 0.1:1 to 1:0.1, and more preferably 0.5:1 to 1:0.5. The amount of compound (M-7) used is typically 0.1 to 10 moles, preferably 0.3 to 5 moles, per 1 mole of the total amount of compound (M-3) and compound (M-7).

[0059] The reaction between compound (M-3), compound (M-6), and compound (M-7) may be carried out in the presence of a solvent. The solvent used in the reaction between compound (M-3), compound (M-6), and compound (M-7) includes the solvent exemplified as solvent (E) described later, with amide solvents being preferred, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone being more preferred, and N,N-dimethylformamide being even more preferred. The amount of solvent used in the reaction between compound (M-3), compound (M-6), and compound (M-7) is usually 0.1 to 1000 parts by mass, preferably 0.5 to 100 parts by mass, per 1 part by mass of the total amount of compound (M-3) and compound (M-7).

[0060] The reaction time between compound (M-3), compound (M-6), and compound (M-7) is typically 0.01 hours to 150 hours, with 0.5 hours to 100 hours being preferred. The reaction temperature between compound (M-3), compound (M-6), and compound (M-7) is typically -100°C to 200°C, preferably 0°C to 100°C, and more preferably 20°C to 90°C.

[0061] After each of the above reactions is complete, the method for extracting the target compound is not particularly limited and can be extracted by various known methods. After extraction, the obtained residue may be purified by washing, column chromatography, or recrystallization. The chemical structure of the obtained compound can be analyzed by known analytical methods and conditions. Such analytical methods are not particularly limited, but examples include mass spectrometry (LC), NMR analysis, and elemental analysis.

[0062] The thermal decomposition initiation temperature of compound (I) is preferably 360°C or higher, more preferably 365°C or higher, even more preferably 370°C or higher, even more preferably 375°C or higher, and even more preferably 380°C or higher. A higher thermal decomposition initiation temperature of compound (I) is preferable, but it may be, for example, 450°C or lower. If the thermal decomposition initiation temperature of compound (I) is within the above range, it is more useful as a coloring agent for color filters that have a heating step in their manufacture. In this specification, the thermal decomposition initiation temperature refers to the 5% weight loss temperature when thermogravimetric differential thermal analysis (TG-DTA) is performed under a nitrogen atmosphere at a heating rate of 10°C / min.

[0063] Compound (I) preferably has a maximum absorption wavelength in the wavelength range of 400 to 780 nm that is between 430 nm and 490 nm, more preferably between 450 nm and 490 nm, and even more preferably between 470 nm and 485 nm. If the maximum absorption wavelength in the wavelength range of 400 to 780 nm is within the above range, compound (I) can be suitably used as a yellow coloring agent for green color filters. The maximum absorption wavelength in the wavelength range of 400 to 780 nm can be measured using a UV-Vis spectrophotometer (e.g., V-650DS; manufactured by JASCO Corporation). The measurement method can be carried out as follows, for example. First, 0.10 g of the compound is added to a volumetric flask, and N,N-dimethylformamide is added to dissolve it to a volume of 0.02 L. 0.002 L of this is added to another volumetric flask and diluted with chloroform to a volume of 0.2 L (concentration: 0.01 g / L) to prepare a dilution for measurement. The diluted solution prepared in this manner is placed in a 1 cm square quartz cell, and the absorption spectrum is measured using a UV-Vis spectrophotometer in the wavelength range of 400 to 780 nm (data sampling interval of 1 nm). The wavelength at which the absorbance in this absorption spectrum is highest is defined as the maximum absorption wavelength λmax.

[0064] Compound (I) preferably has a low average transmittance in the wavelength range of 400 to 490 nm, for example, preferably 20% or less, more preferably 16% or less, even more preferably 14% or less, even more preferably 12% or less, and even more preferably 10% or less. The lower limit is not particularly limited, but may be 0% or more, or 1% or more. The average transmittance refers to the average value of the transmittance for each 1 nm wavelength in the wavelength range of 400 to 490 nm. If the average transmittance in the wavelength range of 400 to 490 nm is within the above range, the transmission of blue light in the backlight can be suppressed, so compound (I) can be suitably used as a yellow coloring agent for green color filters.

[0065] Compound (I) preferably has a low transmittance at a wavelength of 490 nm, for example, preferably 90% or less, more preferably 85% or less, even more preferably 80% or less, and even more preferably 75% or less. The lower limit is not particularly limited, but may be 0% or more, 25% or more, or 50% or more. If the transmittance at a wavelength of 490 nm, where blue light and green light mix, is within the above range, the transmission of blue light in the backlight can be suppressed more effectively, so compound (I) can be more preferably used as a yellow coloring agent for green color filters.

[0066] Compound (I) preferably has a high minimum transmittance in the wavelength range of 510 to 780 nm, for example, 80% or more is preferred, 85% or more is more preferred, 90% or more is even more preferred, 95% or more is even more preferred, and 97% or more is even more preferred. There is no particular upper limit, but it may be 100% or less, or 99.5% or less. If the minimum transmittance in the wavelength range of 510 to 780 nm is within the above range, green light can be transmitted well, so compound (I) can be more preferably used as a yellow coloring agent for green color filters.

[0067] Compound (I) preferably has a difference of 10% or more between its transmittance at a wavelength of 490 nm and its transmittance at a wavelength of 510 nm, more preferably 15% or more, even more preferably 20% or more, and even more preferably 25% or more. If the difference between the transmittance at a wavelength of 490 nm and its transmittance at a wavelength of 510 nm is within the above range, compound (I) can be more preferably used as a yellow coloring agent for green color filters.

[0068] The transmittance of a compound can be determined, for example, as follows: First, the absorption spectrum is measured using the above measurement method to determine the maximum absorption wavelength. This maximum absorption wavelength is then normalized to 2, and converted into a transmission spectrum to obtain the transmittance at each wavelength.

[0069] Compound (I) is preferably one in which the maximum absorption wavelength in the wavelength range of 400 to 780 nm is 430 nm to 490 nm, the average transmittance in the wavelength range of 400 to 490 nm is 20% or less, the transmittance at 490 nm is 90% or less, and the minimum transmittance in the wavelength range of 510 to 780 nm is 80% or more. Particularly preferred is compound (I) in which the maximum absorption wavelength in the wavelength range of 400 to 780 nm is 470 nm to 485 nm, the average transmittance in the wavelength range of 400 to 490 nm is 14% or less, the transmittance at 490 nm is 90% or less, and the minimum transmittance in the wavelength range of 510 to 780 nm is 80% or more.

[0070] <Colored resin composition> A colored resin composition containing the aforementioned compound (I) is also included in the present invention. The colored resin composition of the present invention contains a colorant (hereinafter sometimes referred to as colorant (A)) and a resin (hereinafter also referred to as resin (B)), wherein the colorant (A) contains compound (I). A coloring agent (A) containing the aforementioned compound (I) is also included in the present invention. The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and / or a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), and it is preferable to contain at least one of polymerizable compound (C) and polymerization initiator (D), and more preferable to contain both. The colored resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)) and / or a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In this specification, the compounds exemplified as components may be used individually or in combination unless otherwise specified.

[0071] <Coloring agent (A)> The coloring agent (A) contains the compound (I). By including the compound (I) in the coloring agent (A), a color curable resin composition containing the coloring agent can form a color filter with good heat resistance, and preferably a color filter with good color purity in addition to heat resistance.

[0072] The colorant (A) may further contain a colorant different from compound (I) (hereinafter sometimes referred to as colorant (A1)). Colorant (A1) may be either a dye or a pigment, or may contain both.

[0073] Examples of dyes include compounds classified as having hue other than pigments in the Color Index (published by The Society of Dyers and Colourists), and known dyes listed in the Dyeing Notes (Irozome Co., Ltd.).

[0074] 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.

[0075] Specifically, the dyes used are CI Solvent Yellow 4 (hereafter, the designation "CI Solvent Yellow" will be omitted, and only the numbers will be listed; the same applies to others), 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 Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; and other CI solvent dyes. 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, 1 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 Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; and other CI Acid dyes. 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, 16 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 Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; and other CI Direct dyes. CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 60; and other CI disperse dyes. 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 Green 1; and other CI Basic dyes, CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive Red 36; and other CI reactive dyes, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant 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 Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Modern Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; and other CI Modant dyes. Examples include CI bat green 1 and other CI bat dyes. These dyes may use one or more dyes for each color, or a combination of dyes for each color.

[0076] Examples of pigments include those classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0077] 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; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments; 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, and other red pigments; CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, and other blue pigments; CI Pigment Violet 1, 19, 23, 32, 36, 38, and other violet color pigments; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1 and 7. These pigments may use one or more pigments for each color, or a combination of pigments for each color.

[0078] The pigment may be subjected to rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc., as needed. The particle size of the pigment is preferably substantially uniform.

[0079] The content of colorant (A) in the colored resin composition is preferably 0.5 to 50% by mass, more preferably 1.0 to 40% by mass, even more preferably 2.0 to 30% by mass, even more preferably 3.0 to 25% by mass, and even more preferably 5.0 to 20% by mass, based on the total amount of solids. When the content of colorant (A) is within the above range, it becomes easier to obtain the desired spectral characteristics and color density. In this specification, "total amount of solids" refers to the total amount of components from the composition of the present invention excluding the solvent. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0080] The content of compound (I) in the colored resin composition is preferably 0.5 to 50% by mass, more preferably 1.0 to 40% by mass, even more preferably 2.0 to 30% by mass, even more preferably 3.0 to 25% by mass, and even more preferably 5.0 to 20% by mass, based on the total amount of solids. When the content of compound (I) in the colored resin composition is within the above range, the desired spectral characteristics are more easily obtained, and the reliability of heat resistance and other properties is more easily improved.

[0081] The content of compound (I) is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, even more preferably 40 to 100% by mass, even more preferably 50 to 100% by mass, even more preferably 60 to 100% by mass, and even more preferably 80 to 100% by mass, based on the total amount of coloring agent (A). When the content of compound (I) in coloring agent (A) is within the above range, the desired spectral characteristics are more easily obtained, and the reliability of heat resistance and other properties is more easily improved.

[0082] <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 is preferably at least one selected from the group consisting of resins [K1] to [K6].

[0083] 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 monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]; a copolymer having structural units derived from (a) and structural units derived from (b) and 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 structural units obtained by adding (b) to structural units derived from (a) and structural units derived from (c), wherein the copolymer includes structural units derived from (a) to which (b) is not added; Resin [K4']; a copolymer having structural units obtained by adding (b) to structural units derived from (a) and structural units derived from (c), and not containing structural units derived from (a) to which (b) is not added; Resin [K5]; a copolymer having structural units obtained by adding (a) to structural units derived from (b) and structural units derived from (c) (it may include structural units derived from (b) to which (a) is not added, but it is preferable that it not be included); Resin [K6]; A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c).

[0084] (a) specifically includes, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, 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 carboxyl groups, 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]hepto-2-ene anhydride; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0085] 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" have the same meaning.

[0086] (b) refers to a polymerizable compound having, for example, a cyclic ether structure with 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 with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0087] Examples of (b) include monomers having an oxyranyl group and an ethylenically unsaturated bond (b1) (hereinafter sometimes referred to as "(b1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (b2) (hereinafter sometimes referred to as "(b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)").

[0088] Examples of (b1) include monomers having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized (b1-1) (hereinafter sometimes referred to as "(b1-1)") and monomers having a cyclic unsaturated hydrocarbon structure that has been epoxidized (b1-2) (hereinafter sometimes referred to as "(b1-2)").

[0089] (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyl Examples include oxymethylstyrene, 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.

[0090] (b1-2) includes vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 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), and 3,4-epoxytricyclo[5.2.1.0 2,6 Examples include decyl (meth)acrylates, compounds represented by formula (BI), and compounds represented by formula (BII).

[0091] [ka]

[0092] [In formulas (BI) and (BII), R e and R f This 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 hydroxyl group. X e and X f This is a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g Represents -NH- R g This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0093] Examples of alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with hydroxyl include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group. R e and R f Preferably, the group can be a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0094] Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl. X e and X f Preferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- and *-CH2CH2-O-, and more preferably, single bonds and *-CH2CH2-O- (* represents a bond with O).

[0095] Compounds represented by formula (BI) include those represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BII-5), (BI-7), (BI-9), or (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9), or (BI-15) are more preferred.

[0096] [ka]

[0097] Compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), or (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), or (BII-15) are more preferred.

[0098] [ka]

[0099] The compound represented by formula (BI) and the compound represented by formula (BII) may be used individually 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, their content ratio [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.

[0100] For (b2), monomers having an oxetanyl group and a (meth)acryloyloxy group are more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

[0101] For (b3), monomers having a tetrahydrofurfuryl group and a (meth)acryloyloxy group are more preferred. Specifically for (b3), examples include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0102] (b) is preferable because it allows for greater reliability of the heat resistance, chemical resistance, etc., of the resulting color filter. Furthermore, (b1-2) is more preferable because it provides excellent storage stability for the colored resin composition.

[0103] Examples of (c) include (meth)acrylic acid ester monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters; vinyl monomers such as vinyl monomers having an unsaturated aliphatic hydrocarbon ring or an aromatic ring; maleimides; and so on. Examples of (meth)acrylic acid ester monomers include (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups, 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 linear or branched aliphatic unsaturated hydrocarbon groups, 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 cyclic saturated hydrocarbon groups, such as decane-8-yl(meth)acrylate (commonly referred to as "dicyclopentanyl(meth)acrylate" in the relevant art, and sometimes as "tricyclodecyl(meth)acrylate"), isobornyl(meth)acrylate, and adamantyl(meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having cyclic unsaturated aliphatic hydrocarbon groups, such as decen-8-yl (meth)acrylate (commonly referred to as "dicyclopentenyl (meth)acrylate" in the art) and dicyclopentanyloxyethyl (meth)acrylate; Aromatic ring-containing (meth)acrylic acid esters such as phenyl(meth)acrylate, naphthyl(meth)acrylate, benzyl(meth)acrylate, and phenoxybenzyl(meth)acrylate; Examples include hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate. Examples of unsaturated dicarboxylic acid esters include diethyl maleate, diethyl fumarate, and diethyl itaconate.

[0104] Among these unsaturated carboxylic acid esters, C methacrylate, 2-ethylhexyl acrylate, etc. 1-10 Alkyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having cyclic saturated hydrocarbon groups, such as decane-8-yl(meth)acrylate; Tricyclo[5.2.1.0 2,6(meth)acrylic acid esters having cyclic unsaturated aliphatic hydrocarbon groups, such as decen-8-yl(meth)acrylate; (Meth)acrylic acid esters having aromatic rings, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate; etc. are preferred.

[0105] Examples of vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (also known as 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, and 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 Examples of bicyclounsaturated compounds include 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, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene. Examples of vinyl monomers having aromatic rings 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, 2,3-dimethyl-1,3-butadiene, etc. Among these vinyl monomers, styrene-based monomers such as styrene and vinyltoluene, and bicyclounsaturated compounds such as bicyclo[2.2.1]hepto-2-ene (also known as 2-norbornene) are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0106] Examples of maleimides include N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide. Among these maleimides, maleimides having alicyclic hydrocarbon groups or aromatic hydrocarbon groups, such as N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide, are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0107] A structural unit obtained by adding (b) to a structural unit derived from (a) is a unit formed by the addition of (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 examples above, and (b) may also be any of the examples above. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is more preferred.

[0108] A structural unit obtained by adding (a) to a structural unit derived from (b) is 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 examples above, and (a) may also be any of the examples above. As (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0109] A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride is a structural unit in which a hydroxyl group formed by the bonding of (a) to a structural unit derived from (b) constituting the main chain of the copolymer is bonded to by the carboxylic acid anhydride through half-esterification, and has a pendant carboxyl 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 examples, and (a) may also be any of the above examples. As (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been 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 acid anhydride, succinic acid anhydride, glutaric acid anhydride, and adipic acid anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic acid anhydride, citraconic acid anhydride, and itaconic acid anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic acid anhydride and 4-vinylphthalic acid anhydride; and alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic acid anhydride, 1,2,3,6-tetrahydrophthalic acid anhydride, dimethyltetrahydrophthalic acid anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; and other polycarboxylic acid anhydrides.

[0110] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. Furthermore, it is preferable that the structural units derived from (c) are substantially omitted. The sum of structural units derived from (a) and 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 the total structural units constituting the resin [K1]. When the ratio of structural units of resin [K1] falls within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0111] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0112] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents include those described later as solvent (E) of the colored resin composition of the present invention.

[0113] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored resin composition of the present invention, thereby simplifying the manufacturing process of the colored resin composition of the present invention.

[0114] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 1-70 mol% (b) Structural units derived from (b); 1-60 mol% (c) Structural units derived from (c); 20-95 mol% It is preferable that this be the case. (a) Structural units derived from (a); 3-50 mol% (b) Structural units derived from (b); 3-40 mol% (c) Structural units derived from (c); 30-90 mol% It is more preferable that, (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-30 mol% (c) Structural units derived from (c); 40-80 mol% It is even more preferable that it be so. The sum of structural units derived from (a), (b), and (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 the total structural units constituting the resin [K2]. When the ratio of structural units of resin [K2] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0115] In resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. For (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized is more preferred. For (c), (meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, and dicarbonylimide derivatives are preferred.

[0116] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0117] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from this structure; 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is more preferable that, (a) Structural units derived from (a); 35-45 mol% (c) Structural units derived from (c); 55-65 mol% It is even more preferable that it be so. It is preferably substantially free of the structural unit derived from (b). The total of the structural unit derived from (a) and the structural unit 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% in all the structural units constituting the resin [K3].

[0118] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (c) is preferably (meth)acrylic acid esters having an aromatic ring. The resin [K3] can be produced, for example, in the same manner as the method described as the production method of the resin [K1].

[0119] In the resin [K4], the ratio of the structural unit derived from each is among all the structural units constituting the resin [K4], The structural unit derived from (a) (b is not added); 1 to 60 mol% The structural unit obtained by adding (b) to the structural unit derived from (a); 1 to 50 mol% The structural unit derived from (c); 30 to 90 mol% is preferably, The structural unit derived from (a) (b is not added); 5 to 50 mol% The structural unit obtained by adding (b) to the structural unit derived from (a); 5 to 40 mol% [[ID=2x]] The structural unit derived from (c); 35 to 80 mol% is more preferably, The structural unit derived from (a) (b is not added); 10 to 40 mol% The structural unit obtained by adding (b) to the structural unit derived from (a); 10 to 25 mol% The structural unit derived from (c); 40 to 75 mol% is even more preferably. The sum of structural units derived from (a) (without (b) added), structural units derived from (a) with (b) added, and 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 the total structural units constituting the resin [K4].

[0120] As structural units derived from (a) (without (b) being added), structural units derived from unsaturated monocarboxylic acids such as (meth)acrylic acid are preferred. As structural units obtained by adding (b) to structural units derived from (a), structural units obtained by adding a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid are preferred. As structural units derived from (c), one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups, (meth)acrylic acid esters having cyclic saturated hydrocarbon groups, (meth)acrylic acid esters having aromatic rings, bicyclounsaturated compounds, and styrene monomers are preferred, and two or more are more preferred. When (c) has two constituent units derived from (c), it is preferable to select two 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 to select two or more from bicyclounsaturated compounds and vinyl monomers such as styrene monomers.

[0121] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (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, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0122] Next, a portion 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 that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.), a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.), and another polymerization inhibitor (e.g., hydroquinone, etc.) are added to the flask and reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored resin composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0123] In resin [K4'], the ratio of structural units derived from each is, among all structural units constituting resin [K4'], A structural unit obtained by adding (b) to a structural unit derived from (a); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. A structural unit obtained by adding (b) to a structural unit derived from (a); 15-90 mol% (c) Structural units derived from (c); 10-85 mol% It is more preferable that, A structural unit obtained by adding (b) to a structural unit derived from (a); 20-80 mol% (c) Structural units derived from (c); 20-80 mol% It is even more preferable that it be so. Furthermore, structural units derived from (a) but without (b) attached are not substantially included. The sum of structural units derived from (a) with (b) added, and 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 the total structural units constituting the resin [K4'].

[0124] As a structural unit obtained by adding (b) to a structural unit derived from (a), a preferred structural unit is one obtained by adding a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. As a structural unit derived from (c), one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups and (meth)acrylic acid esters having cyclic saturated hydrocarbon groups are preferred, and two or more are more preferred. The resin [K4'] may be prepared by referring to the above method for producing resin [K4], and the amount of (b) used is preferably 100 moles or more, and more preferably 100 moles, per 100 moles of (a).

[0125] In resin [K5], the ratio of structural units derived from each is, among all structural units constituting resin [K5], (b) Structural units derived from (a) (without addition of (a)); 0-30 mol% Structural units obtained by adding (a) to structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (a) (without addition); 0-10 mol% Structural units obtained by adding (a) to structural units derived from (b); 15-90 mol% (c) Structural units derived from (c); 10-85 mol% It is more preferable that, (b) Structural units derived from (a) (without addition); 0-5 mol% Structural units obtained by adding (a) to structural units derived from (b); 20-80 mol% (c) Structural units derived from (c); 20-80 mol% It is even more preferable that it be so. The sum of structural units derived from (b) (without (a) added), structural units derived from (b) with (a) added, and 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 the total structural units constituting the resin [K5].

[0126] As structural units derived from (b) (without (a) attached), structural units derived from monomers (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure epoxidized are preferred. As structural units obtained by attaching (a) to structural units derived from (b), structural units obtained by attaching an unsaturated monocarboxylic acid such as (meth)acrylic acid to structural units derived from monomers (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure epoxidized are preferred. As structural units derived from (c), one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups and (meth)acrylic acid esters having cyclic saturated hydrocarbon groups are preferred, and two or more are more preferred.

[0127] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. (b) and the ratio of the structural units derived from (c) are, respectively, based on the total number of moles of all the structural units constituting the copolymer, Structural units derived from (b); 5 to 95 mol% Structural units derived from (c); 5 to 95 mol% It is preferably that, Structural units derived from (b); 10 to 90 mol% Structural units derived from (c); 10 to 90 mol% It is more preferably that.

[0128] Furthermore, under the same conditions as the production method of resin [K4] or resin [K4'], by reacting the carboxylic acid or carboxylic anhydride of (a) with the cyclic ether derived from (b) in the copolymer of (b) and (c), resin [K5] can be obtained. The amount of (a) used for reacting with the copolymer is preferably 5 to 100 mol, more preferably 60 to 100 mol, per 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) is unlikely to remain, (b1) is preferably used as (b) for resin [K5], and further preferably (b1-1).

[0129] In resin [K6], the ratio of the structural units derived from each is among all the structural units constituting resin [K6], Structural units derived from (b) (without addition of (a)); 0 to 30 mol% Structural units obtained by adding (a) to the structural units derived from (b) (without addition of carboxylic anhydride); 20 to 85 mol% Structural units obtained by adding (a) to the structural units derived from (b) and further adding carboxylic anhydride; 2 to 40 mol% Structural units derived from (c); 10 to 60 mol% It is preferably that, Structural units derived from (b) (without addition of (a)); 0 to 10 mol% Structural units obtained by adding (a) to the structural units derived from (b) (without addition of carboxylic anhydride); 40 to 80 mol% A structural unit obtained by adding (a) to a structural unit derived from (b), and then adding a carboxylic acid anhydride; 3-30 mol% (c) Structural units derived from (c); 15-50 mol% It is more preferable that, (b) Structural units derived from (a) (without addition); 0-5 mol% (b) is a structural unit to which (a) is added (no carboxylic acid anhydride is added); 50-70 mol% A structural unit obtained by adding (a) to a structural unit derived from (b), and then adding a carboxylic acid anhydride; 5-20 mol% (c) Structural units derived from this structure; 20-40 mol% It is even more preferable that it be so.

[0130] The sum of structural units derived from (b) (without (a) added), structural units obtained by adding (a) to structural units derived from (b) (without carboxylic acid anhydride added), structural units obtained by adding (a) to structural units derived from (b) and further adding carboxylic acid anhydride, and 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 the total structural units constituting the resin [K6].

[0131] As a structural unit derived from (b) (without (a) being added), a structural unit derived from a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is preferred. As a structural unit obtained by adding (a) to a structural unit derived from (b) (without carboxylic acid anhydride being added), a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit derived from a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is preferred. As a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit derived from a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is preferred, and further adding a saturated aliphatic polycarboxylic acid anhydride such as succinic anhydride is preferred. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups and (meth)acrylic acid esters having cyclic saturated hydrocarbon groups, and more preferably two or more.

[0132] As a first step, resin [K6] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0133] Furthermore, under the same conditions as for the production of resin [K4], the cyclic ether derived from (b) in the copolymer of (b) and (c) is reacted with the carboxylic acid or carboxylic acid anhydride of (a). The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0134] The hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic acid anhydride of (a) is reacted with the carboxylic acid anhydride. The amount of carboxylic acid anhydride used is preferably 0.05 to 1 mole, more preferably 0.10 to 0.8 moles, and even more preferably 0.13 to 0.7 moles, relative to 1 mole of (a) used (in other words, 1 mole of hydroxyl group generated by the use of (a)).

[0135] Specifically, resin (B) is 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / tricyclo[5.2.1.0 2,6 ] Decen-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 ] Resins such as decyl acrylate / (meth)acrylic acid / phenoxybenzyl(meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymers and styrene / (meth)acrylic acid copolymers [K3]; Resins such as those obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer [K4]; Resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / (meth)acrylic acid copolymer with glycidyl (meth)acrylate, and resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer with glycidyl (meth)acrylate [K4']; Resins such as resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, and resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; Examples of resins include those obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with tetrahydrophthalic anhydride; resins obtained by reacting a 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with succinic anhydride; and resins obtained by reacting a methyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with succinic anhydride [K6].

[0136] The resins [K1] to [K6] may be one type or a combination of two or more types. In particular, resin (B) preferably contains resin [K1] and / or resin [K2], and more preferably contains resin [K1].

[0137] The weight-average molecular weight of resin (B) in terms of polystyrene 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 color pattern tends to improve.

[0138] The degree of dispersion of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0139] The acid value of resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 30 to 150 mg-KOH / g, and even more preferably 40 to 135 mg-KOH / g, based on solid content. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0140] The content of resin (B) is preferably 2 to 65% by mass, more preferably 10 to 60% by mass, and even more preferably 15 to 55% by mass, of 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 improve. Furthermore, the content of compound (I) per 100 parts by mass of resin (B) is preferably 1 to 150 parts by mass, more preferably 5 to 100 parts by mass, and even more preferably 10 to 80 parts by mass.

[0141] <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 include compounds having polymerizable ethylenically unsaturated bonds, and is preferably a (meth)acrylic acid ester compound.

[0142] In particular, 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 Pentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl) isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated Xylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylate (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol Examples include hexa(meth)acrylate, caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), etc. In particular, it is preferable that it be at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate, and more preferably that it contains at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0143] The weight-average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0144] The content of polymerizable compound (C) is preferably 5 to 80% by mass, more preferably 10 to 60% by mass, and even more preferably 20 to 55% by mass, of the total amount of solids in the colored resin composition. When the content of polymerizable compound (C) is within the above range, the residual film rate when forming the colored pattern and the chemical resistance of the color filter tend to improve.

[0145] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc., upon the action of light or heat and can initiate polymerization; any known polymerization initiator can be used.

[0146] Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0147] The O-acyloxime compound is a compound having a substructure represented by formula (d1). Hereinafter, * represents a bond.

[0148] [ka]

[0149] Examples of the O-acyloxime compounds 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-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N- Examples include acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one. Commercially available products such as Irgacure® OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, O-acyloxime compounds include N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1- At least one selected from the group consisting of on-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-on-2-imine is preferred, and at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-on-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-on-2-imine is more preferred. These O-acyloxime compounds tend to yield high-brightness color filters.

[0150] The alkylphenone compound is a compound having a substructure represented by formula (d2) or formula (d3). In these substructures, the benzene ring may have substituents.

[0151] [ka]

[0152] Examples of compounds having the substructure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure® 369, 907, and 379 (all manufactured by BASF) may also be used.

[0153] Examples of compounds having the substructure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal. In terms of sensitivity, alkylphenone compounds having the substructure represented by formula (d2) are preferred.

[0154] Examples of the aforementioned triazine compounds 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-[ Examples include 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, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0155] Examples of the aforementioned acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0156] Examples of the biimidazole compounds 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, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2- Examples include chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0157] Furthermore, examples of polymerization initiators (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, o-benzoyl methyl benzoate, 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; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) described later.

[0158] Examples of polymerization initiators that generate acids 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, as well as nitrobenzyl tosylates and benzoin tosylates.

[0159] The polymerization initiator (D) is preferably one comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and a polymerization initiator comprising an O-acyloxime compound is more preferred.

[0160] The content of the polymerization initiator (D) is preferably 0.1 to 50 parts by mass, more preferably 1 to 45 parts by mass, and even more preferably 2 to 40 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time is shortened, thus improving the productivity of color filters.

[0161] <Polymerization initiator (D1)> Polymerization initiator (D1) is a compound or sensitizer used to accelerate the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D). Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0162] Examples of the amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0163] Examples of the alkoxyanthracene compounds 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.

[0164] Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0165] Examples of the carboxylic acid compounds 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, naphthoxyacetic acid, and the like.

[0166] When these polymerization initiators (D1) are used, their content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the amount of polymerization initiator (D1) is within this range, it is possible to form a colored pattern with even higher sensitivity, and the productivity of color filters tends to improve.

[0167] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing both -CO- and -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, and the like.

[0168] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0169] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole.

[0170] Examples of 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, 2-ethoxypropionate Examples include ethyl xy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0171] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0172] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0173] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0174] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0175] Of the above solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred from the viewpoint of applicability and drying properties. As the solvent, at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide is preferred, and at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate is more preferred.

[0176] The solvent (E) content is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, relative to the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating is good, and the color density is not insufficient when a color filter is formed, which tends to result in good display characteristics and sensitivity.

[0177] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0178] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0179] Examples of the aforementioned fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc. (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0180] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0181] The content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and even more preferably 0.005 to 0.05% by mass, of the total amount of the colored resin composition. Note that this content does not include the content of the dispersant described later. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0182] <Other ingredients> The colored resin composition may optionally contain additives known in the art, such as dispersants, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.

[0183] <Method for producing colored resin composition> A colored resin composition can be prepared, for example, by mixing a colorant (A) and a resin (B), along with a polymerizable compound (C), polymerization initiator (D), solvent (E), leveling agent (F), polymerization initiator aid (D1), and other components as needed. Mixing can be carried out using known or conventional equipment and conditions. The colored resin composition after mixing may be filtered through a filter with a pore size of approximately 0.01 to 10 μm.

[0184] The coloring agent (A) may be pre-mixed with part or all of the resin (B) and part or all of the solvent (E) to prepare a colored composition (coloring agent-containing liquid). The colored composition may further contain a dispersant. The desired colored resin composition can be prepared by mixing the remaining components into such a colored composition to a predetermined concentration.

[0185] Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specifically, examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants may be used individually or in combination of two or more. Examples of dispersants, as trade names, include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers® (registered trademark) (manufactured by Zeneca K.K.), EFKA® (registered trademark) (manufactured by BASF Ltd.), Adisper® (registered trademark) (manufactured by Ajinomoto Fine Techno Inc.), Disperbyk® (registered trademark), and BYK® (registered trademark) (manufactured by Bic Chemie Inc.).

[0186] The content of coloring agent (A) in the colored composition is preferably 1 to 90% by mass, more preferably 3 to 80% by mass, even more preferably 5 to 70% by mass, and even more preferably 10 to 60% by mass, based on the total amount of solids.

[0187] The solvent (E) content is preferably 40-99% by mass, more preferably 50-97% by mass, and even more preferably 55-95% by mass, relative to the total amount of the colored composition. In other words, the solid content of the colored composition is preferably 1-60% by mass, more preferably 3-50% by mass, and even more preferably 5-45% by mass.

[0188] The amount of dispersant is preferably 1 to 200 parts by mass, more preferably 10 to 150 parts by mass, and even more preferably 20 to 120 parts by mass, per 100 parts by mass of colorant (A) in the colored composition.

[0189] The colored composition may be dispersed using a bead mill or the like until the average particle size of the colorant (A) is approximately 0.2 μm or less. When using a bead mill, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the bead material may be glass, ceramic, metal, etc.

[0190] <How to manufacture color filters> Methods for producing a colored pattern for a color filter from the colored resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed to light through a photomask for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the composition layer, can be formed.

[0191] The film thickness of the color filter (colored coating or colored pattern) is not particularly limited and can be adjusted as appropriate depending on the purpose and application. For example, it is 30 μm or less, preferably 20 μm or less, more preferably 10 μm or less, even more preferably 6 μm or less, and even more preferably 3 μm or less. It is also preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0192] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed can be used. Other color filter layers, resin layers, transistors, circuits, etc., may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS may be used.

[0193] The formation of each color pixel (color filter) by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows: First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying to obtain a smooth composition layer. Application methods include spin coating, slit coating, and slit and spin coating. When performing heat drying, the temperature is preferably 30 to 120°C, and more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited and can be appropriately selected according to the desired film thickness of the color filter.

[0194] Next, the composition layer is exposed via a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. A light source that generates light with a wavelength of 250 to 450 nm is preferred for exposure. For example, light below 250 nm can be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. It is preferable to use a reduction projection exposure apparatus or proximity exposure apparatus such as a mask aligner and stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment of the photomask and the substrate.

[0195] A colored pattern is formed on the substrate by developing the exposed composition layer in contact with a developer. During development, the unexposed parts of the composition layer are dissolved and removed in the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. 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. Furthermore, the developer may also contain a surfactant. The development method may be any of the following: the paddle method, the dipping method, and the spray method. Furthermore, the substrate may be tilted at any angle during development. After developing, it is preferable to wash the film with water.

[0196] Furthermore, it is preferable to perform a post-bake on the obtained coloring pattern. The post-bake temperature is preferably 80 to 250°C, and more preferably 100 to 245°C. The post-bake time is preferably 1 to 120 minutes, and more preferably 2 to 40 minutes.

[0197] The colored patterns and colored coatings obtained in this manner are useful as color filters, and these 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 image sensors, etc. [Examples]

[0198] 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 it is certainly possible to implement it with appropriate modifications within the scope that is consistent with the spirit described above and below, and all such modifications are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "percent mass".

[0199] In the following examples, the structure of the compounds was confirmed by mass spectrometry (LC: Agilent 1200; MASS: Agilent LC / MSD6130; and MALDI-TOF MS: JEOL Ltd. JMS-S3000).

[0200] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, calculated on a polystyrene basis, were measured by GPC (gel permeation chromatography) under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0mL / min Solid content concentration of the analytical sample: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standards: 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 to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0201] (Synthesis Example 1) <Synthesis of compound (B-1)> 97.1 parts of dimethyl terephthalate (manufactured by Tokyo Chemical Industries, Ltd.; compound represented by formula (A-1)) and 757 parts of acetonitrile (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and heated to 60°C. 94.3 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industries, Ltd.) were slowly added, and the mixture was stirred at 60°C for 2 hours. After the reaction was complete, the mixture was cooled to 5°C, and 785 parts of a mixture of 57 parts of pre-prepared concentrated hydrochloric acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 728 parts of deionized water were added dropwise, resulting in the formation of a pale yellow precipitate. The mixture containing this pale yellow precipitate was filtered, and the residue after filtering was washed with 145 parts of deionized water. The resulting residue was dried under reduced pressure at 60°C to obtain 94.4 parts of the compound represented by formula (B-1) (hereinafter sometimes referred to as compound (B-1)) (yield 93%).

[0202] [ka]

[0203] <Identification of compound (B-1)> (Mass Spectrometry) Ionization Mode = ESI + : m / z = 204 [M+H] + Exact Mass: 203

[0204] (Synthesis Example 2) <Synthesis of compound (C-1)> 94.4 parts of compound (B-1) obtained in Synthesis Example 1 and 406 parts of deionized water were mixed and heated to 60°C. 240 parts of 10% by weight aqueous sodium hydroxide solution were added dropwise, and the mixture was stirred at 70°C for 20 minutes. After cooling to 20°C, 750 parts of concentrated hydrochloric acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added dropwise, and a colorless precipitate was formed. The mixture containing this colorless precipitate was filtered, and the residue after filtering was washed with 304 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 88.5 parts of a mixture containing the compound represented by formula (C-1) (hereinafter sometimes referred to as compound (C-1)) and terephthalic acid (E). LC analysis revealed that the mixture contained 77.6 parts (yield 82%) of compound (C-1) and 10.9 parts of terephthalic acid (E).

[0205] [ka]

[0206] <Identification of compound (C-1)> (Mass Spectrometry) Ionization Mode = ESI - : m / z = 188 [MH] - Exact Mass: 189 <Identification of terephthalic acid (E)> (Mass Spectrometry) Ionization Mode = ESI - : m / z = 165 [MH] - Exact Mass: 166

[0207] (Synthesis Example 3) <Synthesis of compound (D-1)> The compound represented by formula (D-1) (hereinafter sometimes referred to as compound (D-1)) was synthesized according to the method described in the Journal of Molecular Structure, 2019, Vol. 1179, pp. 304-314.

[0208] [ka]

[0209] <Identification of compound (D-1)> (Mass Spectrometry) Ionization Mode = ESI + : m / z = 213 [M+H] + Exact Mass: 212

[0210] (Example 1) <Synthesis of compound (I-a1)> 23.0 parts of 1,3-diiminoisoindoline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 150 parts of N,N-dimethylformamide were mixed and heated to 60°C. 34.2 parts (87.7% by weight purity) of the mixture containing compound (C-1) obtained in Synthesis Example 2 were added over 6 hours, and the mixture was stirred at 60°C for 2 hours. 33.7 parts of compound (D-1) obtained in Synthesis Example 3 and 60 parts of N,N-dimethylformamide were added dropwise over 3 hours, and the mixture was stirred at 60°C for 18 hours. The resulting mixture was filtered, and a mixture of 3 parts water and 1000 parts acetic acid was added to 128 parts of the residue, and the mixture was stirred at 80°C for 2 hours. The resulting mixture was filtered, and 3000 parts water was added to 98 parts of the residue, and the mixture was stirred at 80°C for 2 hours. The resulting mixture was filtered, the filtered residue was washed with 3000 parts methanol, and 800 parts N,N-dimethylformamide was added to 95 parts of the residue after washing. The mixture was stirred at 80°C for 2 hours. It was cooled to 0°C and stirred for 2 hours. The resulting mixture was filtered, washed with 600 parts methanol, and the resulting residue was dried under reduced pressure at 60°C to obtain 14.2 parts of the compound represented by formula (I-a1) (hereinafter sometimes referred to as compound (I-a1)) (yield 11%). In the formula, the dashed line indicates that the E-isomer, Z-isomer, or a mixture thereof is included (the same applies hereafter in the examples).

[0211] [ka]

[0212] <Identification of compound (I-a1)> (Mass Spectrometry) Ionization Mode = MALDI-TOF - : m / z = 812 Exact Mass: 812

[0213] (Comparative Example 1) <Synthesis of compound (Ix)> In accordance with the description in paragraph 0200 of Japanese Patent Publication No. 2018-168362, a compound represented by formula (Ix) (hereinafter sometimes referred to as compound (Ix)) was obtained.

[0214] [ka]

[0215] <Identification of compound (Ix)> (Mass Spectrometry) Ionization Mode = ESI - : m / z = 488 [MH] - Exact Mass: 489

[0216] <Thermal decomposition start temperature> The compounds obtained in Example 1 and Comparative Example 1 were used as measurement samples. Under a nitrogen atmosphere, they were heated from 30°C to 550°C at a heating rate of 10°C / min using TG-DTA (manufactured by Rigaku Corporation; TG-DTA8122). The temperature at which a 5% weight loss of the sample was observed was defined as the thermal decomposition initiation temperature. The results are shown in Table 2. As shown in Table 2, the thermal decomposition initiation temperature of compound (I-a1) obtained in Example 1 was 360°C or higher, indicating high heat resistance and confirming its usefulness as a coloring agent for color filters. In contrast, the thermal decomposition initiation temperature of compound (Ix) obtained in Comparative Example 1 was low, below 360°C.

[0217] [Table 2]

[0218] <Absorption and transmission spectra> For the compounds obtained in Example 1 and Comparative Example 1, 0.10 g was added to each volumetric flask, and N,N-dimethylformamide was added to dissolve them, resulting in a volume of 0.02 L. Of this, 0.002 L was added to another volumetric flask and diluted with chloroform to a volume of 0.2 L (concentration: 0.01 g / L). The absorption spectrum of the diluted solution was measured in the wavelength range of 400 to 780 nm using a UV-Vis spectrophotometer (V-650DS; manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm). The maximum absorption wavelength λmax [nm], which is the wavelength at which the absorbance in this absorption spectrum is highest, was determined. Furthermore, the absorbance at λmax was normalized to 2, and the spectrum was converted to a transmission spectrum to calculate the average transmittance in the wavelength range of 400 to 490 nm, the transmittance at 490 nm, and the minimum transmittance in the wavelength range of 510 to 780 nm. The average transmittance mentioned above refers to the average value of the transmittance for each 1 nm wavelength in the wavelength range of 400 to 490 nm. The lower the average transmittance in the wavelength range of 400 to 490 nm, the lower the transmittance at 490 nm (the boundary region between blue and green light), and the higher the minimum transmittance in the wavelength range of 510 to 780 nm, the more suitable the yellow coloring agent for green color filters is. The results obtained are shown in Table 3.

[0219] [Table 3]

[0220] (Synthesis Example 4) A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate were added and heated to 80°C while stirring. Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixture of 289 parts of decane-9-yl acrylate (with a molar ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was complete, the mixture was held at 80°C for 4 hours, then cooled to room temperature to obtain a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s measured with a B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2 × 10⁻⁶. 3 The dispersion was 2.08, and the acid value on a solid content basis was 77 mg-KOH / g. Resin B1 has the following structural units.

[0221] [ka]

[0222] (Example 2) <Preparation of colored resin composition> The components were mixed in the following proportions, and the coloring agent was dispersed using a bead mill. The bead mill was then removed by filtration to obtain colored composition 1. Coloring agent: Compound (I-a1) 100 parts; Dispersant: BYK-LPN6919 (manufactured by Bic Chemie Japan Co., Ltd.: solids content 60%) 167 copies; Resin (B): 229 parts of resin B1 solution; Solvent (E): Propylene glycol monomethyl ether acetate 3105 parts; Diacetone alcohol, 400 parts

[0223] Next, the components were mixed in the following proportions to obtain colored resin composition 1. Coloring composition 1 400 parts; Resin (B): 45 parts of resin B1 solution; Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 25 parts; Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure® OXE-01; manufactured by BASF Ltd.) 15 parts; Solvent (E): Propylene glycol monomethyl ether acetate 86 parts; Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.12 parts

[0224] <Preparation of colored coating film> A colored resin composition 1 was applied by spin coating onto a 5cm square glass substrate (Eagle XG; Corning Corporation) to a post-baking thickness of 2.0 μm. The substrate was then pre-baked at 100°C for 3 minutes to form a colored resin composition layer. After cooling, the colored resin composition layer formed on the substrate was exposed to air at 80 mJ / cm² using an exposure unit (TME-150RSK; Topcon Corporation) in an atmospheric environment. 2 The sample was irradiated with light at the specified exposure level (based on 365 nm). After light irradiation, post-baking was performed in an oven at 230°C for 30 minutes to obtain colored coating film 1.

[0225] <Heat resistance test> The obtained colored coating film 1 was heated in an oven under an atmospheric environment at 230°C for 120 minutes. The absorption spectroscopy of the colored coating film 1 before and after heating was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) to determine the absorbance retention rate. Here, the absorbance retention rate is a value calculated from the following formula, and the closer the absorbance retention rate is to 100%, the better the heat resistance. Absorbance retention rate (%) = (Absorbance at the maximum absorption wavelength of the colored coating after heating) / (Absorbance at the maximum absorption wavelength of the colored coating before heating) × 100 The heat resistance test results showed that the absorbance retention rate of colored coating 1 was 100%. Because compound (I-a1) has a high thermal decomposition initiation temperature, the colored coating film 1 formed from the colored resin composition 1 containing compound (I-a1) as a coloring agent also exhibits high heat resistance, as evidenced by its high absorbance retention rate after the heat resistance test. Furthermore, if the colored coating film has good heat resistance, then an optical filter made from the same colored resin composition can also be said to have excellent heat resistance.

Claims

1. A compound represented by formula (I). 【Chemistry 1】 [In formula (I), A １ ~A ４ These are, independently of each other, a cyano group, a nitro group, and C(O)R. ｘ Base, C(O)OR ｘ group, S(O)R ｘ Base, S(O)OR ｘ Base, or S(O) ２ OR ｘ It represents the basis. R １ and R ２ each independently represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. R ３ and R ４ Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents, a heterocyclic group, which may have substituents, or a hydrogen atom. R ａ , R ｂ and R ｃ These are, independently of each other, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, a heterocyclic group which may have substituents, a halogen atom, a cyano group, a nitro group, a formyl group, and C(O)R. ｘ Base, C(O)OR ｘ group, C(O)OH group, S(O)R ｘ Base, S(O)OR ｘ Group, S(O) ２ R ｘ Group, S(O) ２ OR ｘ Group, S(O) ２ OH group, NR ｘ ２ Base, or NHR ｘ Represents the base, R ａ If there are multiple, they may be the same or different from each other, R ｂ If there are multiple, they may be the same or different from each other, R ｃ If there are multiple instances, they may be the same or different from one another. a, b, and c represent integers from 0 to 4, independently of each other. R ｘ R represents a hydrocarbon group having 1 to 10 carbon atoms. ｘ If there are multiple instances, they may be the same or different from one another. The wavy line indicates the presence of the E-form, Z-form, or a mixture thereof.

2. A １ ~A ４ The compound according to claim 1, wherein the group is a cyano group.

3. A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains the compound described in claim 1 or 2.

4. Furthermore, the colored resin composition according to claim 3 further contains a polymerizable compound and a polymerization initiator.

5. A color filter formed from the colored resin composition described in claim 3.

6. A display device including the color filter described in claim 5.

7. A solid-state image sensor including the color filter described in claim 5.

Images