Colored resin composition, color filter, and display device

Abstract

To provide a colored resin composition which enables formation of a color filter exhibiting a good contrast.SOLUTION: A colored resin composition contains a coloring agent and a resin, wherein the coloring agent contains a compound represented by formula (I), In the formula (I), R1 to R3 are each independently H or a substituted / unsubstituted hydrocarbon group having 1 to 20 carbon atoms; R2 and R3 may form a ring together with N; R4 to R8 are each independently H, -R9 or -O-R9; and R9 is a substituted / unsubstituted hydrocarbon group having 1 to 20 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCD and CMOS sensors, are produced from colored resin compositions. Perylene tetracarboxylic diimide compounds are known as colorants contained in such colored resin compositions (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2020-079397 Summary of the Invention [Problem to be solved by the invention]

[0004] However, color filters formed from conventionally known colored resin compositions using the above-mentioned perylene tetracarboxylic diimide compound as a colorant have sometimes failed to provide a fully satisfactory contrast. Therefore, an object of the present invention is to provide a colored resin composition capable of forming a color filter exhibiting good contrast. [Means for solving the problem]

[0005] The gist of the present invention is as follows. [1] A colored resin composition containing a colorant and a resin, wherein the colorant contains a compound represented by formula (I). [ka] [In formula (I), R 1~R 3 represent, independently of each other, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R 2 and R 3 may be taken together with the nitrogen atom to which they are attached to form a ring which may have a substituent. R 4 ~R 8 are, independently of each other, a hydrogen atom, -R 9 , -OR 9 , -CO-OR 9 , -O-CO-R 9 , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group. R 9 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 9 When there are multiple, they may be the same or different. [2] The colored resin composition according to [1], further comprising a polymerizable compound and a polymerization initiator. [3] A color filter formed from the colored resin composition according to [1] or [2]. [4] A display device comprising the color filter according to [3]. [Effects of the Invention]

[0006] According to the present invention, it is possible to provide a colored resin composition capable of forming a color filter exhibiting good contrast. DETAILED DESCRIPTION OF THE INVENTION

[0007] The colored resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)) and a resin (hereinafter, may be referred to as resin (B)). The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). The colored resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as solvent (E)). The colored resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)). The colored resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.

[0008] <Colorant (A)> The colorant (A) contains a compound represented by formula (I) (hereinafter, may be referred to as compound (I)). Since the colorant (A) contains compound (I), the colored resin composition of the present invention can form a color filter that exhibits good contrast, and preferably can form a color filter that is also excellent in heat resistance and light resistance.

[0009] <<Compound (I)>> [ka] [In formula (I), R 1 ~R 3 represent, independently of each other, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R 2 and R 3 may be taken together with the nitrogen atom to which they are attached to form a ring which may have a substituent. R 4 ~R 8 are, independently of each other, a hydrogen atom, -R 9 , -OR 9 , -CO-OR 9 , -O-CO-R 9 , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group. R 9 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 9 When there are multiple, they may be the same or different.

[0010] R 1 ~R 3 , and R 9 Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0011] R 1 ~R 3 , and R 9Examples of the saturated or unsaturated chain hydrocarbon group represented by the formula (I) include linear alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an icosyl group; an isopropyl group, a (1-ethyl)propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a (3-methyl)butyl group, a (1-methyl)butyl group, a (1-ethyl)butyl group, (2-methyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (3-methyl)pentyl group, (1-ethyl)pentyl group, (2-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, (2-propyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (1-ethyl)hexyl group, (2-ethyl)hexyl group, (1-propyl)hexyl group, (2-propyl)hexyl group, (1-butyl)hexyl group, (2-butyl)hexyl group, (1-pentyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-propyl)heptyl group, (1-butyl)heptyl group, (2-butyl)heptyl group, (1-pentyl)heptyl group, (2-pentyl)heptyl group, (1-hexyl)heptyl group, (2-methyl)octyl group, (2-ethyl)octyl group, (2-propyl)octyl group, (2-butyl)octyl group, (1-pentyl)octyl group, (2 branched alkyl groups such as a (1-pentyl)octyl group, a (1-hexyl)octyl group, a (2-hexyl)octyl group, a (1-heptyl)octyl group, a (2-ethyl)nonyl group, a (2-propyl)nonyl group, a (2-butyl)nonyl group, a (2-pentyl)nonyl group, a (1-hexyl)nonyl group, a (2-hexyl)nonyl group, a (1-heptyl)nonyl group, a (1-octyl)nonyl group, a (2-propyl)decyl group, a (2-butyl)decyl group, a (2-pentyl)decyl group, a (2-hexyl)decyl group, a (1-heptyl)decyl group, and a (2-butyl)undecyl group;Examples of suitable alkenyl groups include vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl. The saturated chain hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 16, and even more preferably 1 to 15. The unsaturated chain hydrocarbon group preferably has 2 to 18 carbon atoms, more preferably 2 to 16, and even more preferably 2 to 15.

[0012] R 1 ~R 3 , and R 9 Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by the formula (I) include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene and cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, and bicyclo[2.2.2]octyl. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16, and even more preferably 3 to 15.

[0013] R 1 ~R 3 , and R 9 Examples of the aromatic hydrocarbon group represented by the formula (I) include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 15 carbon atoms.

[0014] R 1 ~R 3 , and R 9 The hydrocarbon group represented by the formula (I) may be a group in which two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above are combined, as long as the upper limit of the number of carbon atoms is 20 or less. Such a group may be, for example, a group obtained by combining an aromatic hydrocarbon group with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a hydrocarbon group obtained by combining the chain hydrocarbon group, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of combined hydrocarbon groups include aralkyl groups such as benzyl, phenethyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 2-naphthylmethyl, diphenylmethyl, 2,2-diphenylethyl, 3,3-diphenylpropyl, and 4,4-diphenylbutyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, and m-isopropyl. alkylaryl groups such as a p-isopropylphenyl group, a 2,3-diisopropylphenyl group, a 2,4-diisopropylphenyl group, a 2,5-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 3,5-diisopropylphenyl group, a 2,4,6-triisopropylphenyl group, a 4-butylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a 2,6-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)phenyl group, a 3,6-di(tert-butyl)phenyl group, a 4-tert-butyl-2,6-dimethylphenyl group, a 4-pentylphenyl group, a 4-octylphenyl group, a 4-(2,4,4-trimethyl-2-pentyl)phenyl group, a 2-dodecylphenyl group, a 3-dodecylphenyl group, and a 4-dodecylphenyl group;o-Tolylmethyl group, m-tolylmethyl group, p-tolylmethyl group, 2-ethylphenylmethyl group, 3-ethylphenylmethyl group, 4-ethylphenylmethyl group, 2,3-dimethylphenylmethyl group, 2,4-dimethylphenylmethyl group, 2,5-dimethylphenylmethyl group, 2,6-dimethylphenylmethyl group, 3,4-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2,4,6-trimethylphenylmethyl group, 4-vinylphenylmethyl group, o-isopropylphenylmethyl group, m-isopropylphenylmethyl group, p-isopropylphenylmethyl group, 2,3-diisopropylphenylmethyl group, 2,4-diisopropylphenylmethyl group, 2,5-diisopropylphenylmethyl group, 2,6-diisopropylphenylmethyl group, 3,5-di Examples of such alkylarylalkyl groups include an isopropylphenylmethyl group; an aryl group having an alkanediyl group bonded thereto, such as a 2,3-dihydro-4-indenyl group, a 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, an 8-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, or a 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; an aryl group having one or more aryl groups bonded thereto, such as a biphenylyl group or a terphenylyl group; a cyclohexylmethylphenyl group, a benzylphenyl group, or a (dimethyl(phenyl)methyl)phenyl group; The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 2-methylcyclopentyl group, a 3-methylcyclopentyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2-methylcyclopent ...2-methylcyclopentyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 2-methylcyclopentyl group, a 2-methylcyclopentyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2-methylcyclopentyl group, a 2-methylcyclopentyl group, a 3-methylcyclohexyl group cyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 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 cyclopropylmethyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl, 4-cyclohexylcyclohexyl groups; alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, or an adamantylmethyl group; and alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as a 2-methylcyclopropylmethyl group, a 2-methylcyclobutylmethyl group, a 3-methylcyclobutylmethyl group, a 2-methylcyclopentylmethyl group, a 3-methylcyclopentylmethyl group, a 2-methylcyclohexylmethyl group, a 3-methylcyclohexylmethyl group, or a 4-methylcyclohexylmethyl group. The group formed by combining two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups preferably has 4 to 20 carbon atoms, more preferably 5 to 18 carbon atoms, and even more preferably 6 to 16 carbon atoms.

[0015] -OR 9Examples of the aryloxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, a (2-ethyl)hexyloxy group, an icosyloxy group, a 1-phenylethoxy group, a 1-methyl-1-phenylethoxy group, a phenyloxy group, a 2,3-dimethylphenyloxy group, a 2,4-dimethylphenyloxy group, a 2,5-dimethylphenyloxy group, a 2,6-dimethylphenyloxy group, a 3,4-dimethylphenyloxy group, and a 3,5-dimethylphenyloxy group.

[0016] -CO-OR 9 Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a phenyloxycarbonyl group, and an icosyloxycarbonyl group.

[0017] -O-CO-R 9 Examples of the alkoxy group include an acetoxy group, a propanoyloxy group, a butanoyloxy group, a 2,2-dimethylpropanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a (2-ethyl)hexanoyloxy group, a heptanoyloxy group, an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, and a benzoyloxy group.

[0018] R 1 ~R 3 , and R 9Examples of the substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have include: a halogen atom; a group formed by combining a monovalent hydrocarbon group with at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (provided that at least one of -O- or -CO- is contained); a nitrile group; a nitro group; an amino group; an amido group; a sulfonamido group; a hydroxy group; a thiol group; an alkylthio group having 1 to 15 carbon atoms, such as a methylthio group or an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group, or a 2-naphthylthio group; a sulfoxy group; an alkylsulfoxy group having 1 to 15 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group; arylsulfoxy groups having 6 to 20 carbon atoms such as an oxy group, a 1-naphthylsulfoxy group, or a 2-naphthylsulfoxy group; a silyl group; a boryl group; alkylamino groups having 1 to 15 carbon atoms such as a monomethylamino group, a dimethylamino group, a monoethylamino group, or a diethylamino group; arylamino groups having 6 to 20 carbon atoms such as a monophenylamino group or a diphenylamino group; aralkylamino groups having 7 to 20 carbon atoms such as a benzylamino group; alkylaminosulfonyl groups having 1 to 15 carbon atoms such as an N-methylaminosulfonyl group, an N,N-dimethylaminosulfonyl group, or an N-ethylaminosulfonyl group; a carboxy group; a carbamoyl group; and heterocyclic groups having 1 to 20 carbon atoms such as a furyl group, a pyrrolyl group, or a thienyl group.

[0019] Examples of the group formed by combining at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (including at least one of -O- or -CO-) with a monovalent hydrocarbon group include groups represented by the following formula (Sa) and formula (Sb).

[0020] [ka] [In formula (Sa) and formula (Sb), R S represents a hydrocarbon group having 1 to 20 carbon atoms, and the methylene groups contained in the hydrocarbon group may be replaced with -O- and / or -CO-. * represents a bond.]

[0021] R S The hydrocarbon group having 1 to 20 carbon atoms represented by the above R 1 ~R 3 , and R 9 Examples are the same as those of the hydrocarbon group represented by the following formula: R S When a methylene group contained in a hydrocarbon group represented by the formula (I) is replaced with -O- and / or -CO-, the number of methylene groups may be 1 or 2 or more. When a methylene group contained in a hydrocarbon group is replaced with -O- and / or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms in the hydrocarbon group.

[0022] Specific examples of the group represented by formula (Sa) include alkoxy groups having 1 to 15 carbon atoms, such as a methoxy group or an ethoxy group; and aryloxy groups having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group, or a 2-naphthyloxy group. Specific examples of the group represented by formula (Sb) include alkylcarbonyl groups having 2 to 15 carbon atoms, such as an acetyl group or a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthylcarbonyl group, or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 15 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 19 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, or a 2-naphthyloxycarbonyl group.

[0023] R 1 ~R 3 , and R 9 When the hydrocarbon group represented by the formula (I) has a substituent, the number of the substituents may be one or two or more, and the two or more substituents may be independently the same or different.

[0024] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0025] R 1is preferably a methyl group, an ethyl group, or a hydrogen atom, more preferably an ethyl group or a hydrogen atom, and even more preferably a hydrogen atom.

[0026] R 2 and R 3 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined, or a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined; more preferably a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, or a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined; even more preferably a saturated chain hydrocarbon group or a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined; still more preferably a saturated chain hydrocarbon group, a saturated chain hydrocarbon group having 2 to 15 carbon atoms, even more preferably a saturated chain hydrocarbon group having 4 to 12 carbon atoms, and even more preferably a saturated chain hydrocarbon group having 4 to 10 carbon atoms. Also, R 2 and R 3 The hydrocarbon group represented by the formula (I) may have a substituent, but it is preferable that it has no substituent.

[0027] R 2 and R 3 Specifically, the hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent represented by the formula (I), is preferably a group represented by the following formulas (D-1) to (D-69) and (G-1) to (G-31), more preferably a group represented by the formulas (D-1) to (D-69) and (G-1) to (G-19), still more preferably a group represented by the formulas (D-1) to (D-69), still more preferably a group represented by the formulas (D-1) to (D-18) and (D-40) to (D-52), still more preferably a group represented by the formulas (D-1) to (D-18), and still more preferably a group represented by the formulas (D-2) to (D-15). In the formulas, * represents a bond.

[0028] [ka]

[0029] [ka]

[0030] [ka]

[0031] [ka]

[0032] R 2 and R 3 The ring formed by combining these with the nitrogen atom to which they are bonded may be saturated or unsaturated, and may be monocyclic or polycyclic.

[0033] R 2 and R 3 The number of members in the ring formed by each of these together with the nitrogen atom to which they are bonded is preferably 3 to 15, more preferably 4 to 12, even more preferably 5 to 10, and even more preferably 5 to 7.

[0034] R 2 and R 3 Examples of the ring formed by these together with the nitrogen atom to which they are bonded include a pyrrolidine ring, a morpholine ring, a piperidine ring, and a piperazine ring, and rings having only one nitrogen atom as a heteroatom, such as a pyrrolidine ring and a piperidine ring, are preferred.

[0035] R 2 and R 3 Specific examples of the ring formed by these together with the nitrogen atom to which they are bonded include rings represented by the following formulae (J-1) to (J-9), in which * represents a bond.

[0036] [ka]

[0037] R 2 and R 3 and (J-1) together with the nitrogen atom to which they are bonded form a ring preferably represented by the above formulas (J-1) to (J-9), more preferably represented by the formulas (J-1) to (J-7), still more preferably represented by the formulas (J-1) to (J-6), and still more preferably represented by the formulas (J-3) to (J-5).

[0038] R 2 and R 3 and the nitrogen atom to which they are bonded may have a ring, which may have a substituent such as R 1 ~R 3 , and R 9 The same examples of the substituents as those that may be contained in the hydrocarbon group having 1 to 20 carbon atoms represented by R 2 and R 3 When the ring formed by these groups together with the nitrogen atom to which they are bonded has a substituent, the number of substituents may be one or two or more, and the two or more substituents may be independently the same or different.

[0039] R 2 and R 3 It is particularly preferred that one of them is a hydrogen atom and the other is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0040] R 4 ~R 8 is a hydrogen atom or -R 9 is preferred, and a hydrogen atom is more preferred. R 9 The alkyl group is preferably a saturated chain hydrocarbon group which may have a substituent, and more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms.

[0041] Compound (I) is, for example, a compound represented by the following formula (Ii): 1 , R 2 and R 3A compound having a combination of any one of the following in Tables 1 to 4, and a compound represented by the following formula (Iii), 23 (R in formula (I) 2 and R 3 and R form a ring together with the nitrogen atom to which they are attached), and R 1 and the combination is any one of those shown in Table 5. In Tables 1 to 5, H represents a hydrogen atom, Et represents an ethyl group, IBu represents an isobutyl group, D-1 to D-15, D-19 to D-34, D-40 to D-67, G-1 to G-6, G-9 to G-14, and G-20 to G-27 represent groups represented by the above formulae (D-1) to (D-15), (D-19) to (D-34), (D-40) to (D-67), (G-1) to (G-6), (G-9) to (G-14), and (G-20) to (G-27), respectively, and J-1 to J-9 represent rings represented by the above formulae (J-1) to (J-9).

[0042] [ka]

[0043] [Table 1]

[0044] [Table 2]

[0045] [Table 3]

[0046] [Table 4]

[0047] [ka] [In formula (III), R23 is R 2 and R 3 and represent a ring formed together with the nitrogen atom to which they are attached.

[0048] [Table 5]

[0049] As the compound (I), the compounds (Ii-1) to (Ii-15) are preferred, and the compounds (Ii-2) to (Ii-15) are more preferred.

[0050] Compound (I) may be: Compounds (Ii-1) to (Ii-334) are preferred, Compounds (Ii-1) to (Ii-237) and compounds (Ii-317) to (Ii-334) are more preferable, Compounds (Ii-1) to (Ii-15), compounds (Ii-32) to (Ii-71), compounds (Ii-80) to (Ii-94), compounds (Ii-111) to (Ii-150), compounds (Ii-159) to (Ii-173), compounds (Ii-190) to (Ii-229), compounds (Ii-318) to (Ii-322), and compounds (Ii-327) to (Ii-331) are more preferable. Compounds (Ii-2) to (Ii-14), compounds (Ii-32) to (Ii-44), compounds (Ii-60) to (Ii-71), compounds (Ii-81) to (Ii-93), compounds (Ii-111) to (Ii-123), compounds (Ii-139) to (Ii-150), compounds (Ii-160) to (Ii-172), compounds (Ii-190) to (Ii-202), compounds (Ii-319) to (Ii-321), and compounds (Ii-328) to (Ii-330) are even more preferred.

[0051] Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) (hereinafter sometimes referred to as compound (pt1)) with malononitrile in a solvent to produce a compound represented by the following formula (pt2) (hereinafter sometimes referred to as compound (pt2)), by subjecting compound (pt2) to a condensation reaction in a solvent using a catalyst to produce a compound represented by the following formula (pt3) (hereinafter sometimes referred to as compound (pt3)), by treating compound (pt3) with concentrated sulfuric acid to produce a compound represented by the following formula (pt4) (hereinafter sometimes referred to as compound (pt4)), by reacting compound (pt4) with a compound represented by the following formula (MA1) (hereinafter sometimes referred to as compound (MA1)) in a solvent to produce a compound represented by the following formula (pt5) (hereinafter sometimes referred to as compound (pt5)), and further by reacting compound (pt5) with a compound represented by the following formula (MA2) (hereinafter sometimes referred to as compound (MA2)) in a solvent.

[0052] [ka]

[0053] [ka]

[0054] [ka] [In the formula, R 1 ~R 8 is the same as the definition above. A represents a hydrogen atom or a halogen atom, and R B represents a halogen atom or a p-toluenesulfonyl group.

[0055] Examples of the compound (pt1) include acenaphthenequinone.

[0056] R AExamples of the halogen atom represented by R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. A is preferably a hydrogen atom.

[0057] The amount of malononitrile used is usually 0.1 mol or more and 500 mol or less, preferably 0.3 mol or more and 400 mol or less, more preferably 0.5 mol or more and 300 mol or less, and even more preferably 0.8 mol or more and 200 mol or less, relative to 1 mol of compound (pt1).

[0058] As the solvent for the reaction of compound (pt1) with malononitrile, it is preferable to use a solvent (particularly an organic solvent) that has been sufficiently deoxidized and / or dehydrated in order to suppress side reactions, and dehydrated acetonitrile is more preferable.

[0059] The amount of the solvent used in the reaction of compound (pt1) with malononitrile is usually 0.1 to 1000 parts by mass relative to 1 part by mass of compound (pt1).

[0060] The reaction temperature when reacting the compound (pt1) with malononitrile is usually −100° C. or higher and 300° C. or lower. The reaction time when reacting the compound (pt1) with malononitrile is usually 0.5 hours to 300 hours.

[0061] Examples of the compound (pt2) include 2-(2-oxo-2H-acenaphthylen-1-ylidene)-malononitrile.

[0062] Catalysts used in the production of compound (pt3) include palladium compounds such as tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladium(II), palladium(II) (π-cinnamyl) chloride (dimer), allylpalladium(II) chloride (dimer), bis(benzonitrile)palladium(II) dichloride, and bis(acetonitrile)palladium(II) dichloride; triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, and N,N-diisopropyl ether. Examples of suitable bases include organic bases such as propylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]-5-nonene, and 1,8-diazabicyclo[5.4.0]-7-undecene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; and inorganic bases such as sodium acetate, potassium phosphate, lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, and cesium bicarbonate. Preferred bases include cesium carbonate, potassium carbonate, potassium phosphate, triethylamine, 4-(N,N-dimethylamino)pyridine, N,N-diisopropylethylamine, and 1,4-diazabicyclo[2.2.2]octane.

[0063] The amount of the catalyst used may be any catalytic amount, for example, 0.1 to 50 moles, preferably 0.5 to 40 moles, and more preferably 1.0 to 30 moles, relative to 100 moles of compound (pt2).

[0064] Examples of the solvent used in the condensation reaction of compound (pt2) in the presence of a catalyst include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. Water and nitrile solvents are preferred, and water and acetonitrile are more preferred.

[0065] The amount of the solvent used in the condensation reaction of the compound (pt2) in the presence of a catalyst is usually 0.1 to 1000 parts by mass per part by mass of the compound (pt2).

[0066] The reaction temperature in the condensation reaction of compound (pt2) in the presence of a catalyst is usually −100° C. or higher and 300° C. or lower. The reaction time in the condensation reaction of compound (pt2) in the presence of a catalyst is usually 0.5 hours to 300 hours.

[0067] Examples of the compound (pt3) include 1-oxo-1H-phenalene-2,3-dicarbonitrile.

[0068] The reaction temperature when compound (pt3) is treated with concentrated sulfuric acid is usually from 0° C. to 300° C. The reaction time when compound (pt3) is treated with concentrated sulfuric acid is usually from 0.5 hours to 300 hours.

[0069] Examples of the compound (pt4) include 1-oxo-1H-phenalene-2,3-dicarboximide.

[0070] Examples of the compound (MA1) include alkyl halides (specifically, ethyl iodide, etc.), alkyl tosylates, and the like.

[0071] The amount of compound (MA1) used is usually 0.4 to 20 moles, preferably 0.5 to 15 moles, more preferably 0.6 to 10 moles, per mole of compound (pt4).

[0072] Examples of the solvent used in the reaction of compound (pt4) with compound (MA1) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. Water and nitrile solvents are preferred, and water and acetonitrile are more preferred.

[0073] The amount of the solvent used in the reaction of the compound (pt4) with the compound (MA1) is usually 0.1 to 1000 parts by mass relative to 1 part by mass of the compound (pt4).

[0074] The reaction of compound (pt4) with compound (MA1) may be carried out in the presence of an alkali in order to neutralize hydrogen halide or tosylic acid generated by the reaction. Examples of the alkali include sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, and triethylamine.

[0075] When an alkali is used in the reaction of compound (pt4) with compound (MA1), the amount of the alkali used is usually 0.1 mol or more and 50 mol or less, and preferably 0.5 mol or more and 30 mol or less, per 1 mol of compound (pt4).

[0076] Examples of the compound (pt5) include N-ethyl-1-oxo-1H-phenalene-2,3-dicarboximide.

[0077] Examples of the compound (MA2) include 1-hexylamine, n-butylamine, benzylamine, diisobutylamine, and piperidine.

[0078] The amount of compound (MA2) used is usually 0.05 to 20 moles, preferably 0.1 to 15 moles, more preferably 0.2 to 10 moles, per mole of compound (pt5).

[0079] Examples of the solvent used in the reaction of compound (pt5) with compound (MA2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole.

[0080] The amount of the solvent used in the reaction of the compound (pt5) with the compound (MA2) is usually 0.1 to 1000 parts by mass per part by mass of the compound (pt5).

[0081] In the reaction of compound (pt5) with compound (MA2), a base may be present to efficiently proceed with the reaction. The base may be an organic base or an inorganic base, preferably an organic base, and more preferably a tertiary amine such as trimethylamine, triethylamine, tri-n-propylamine, tri-n-butylamine, diisopropylethylamine, tri-n-octylamine, tri-n-decylamine, triphenylamine, N,N-dimethylaniline, N,N,N',N'-tetramethylethylenediamine, N-methylpyrrolidine, or 4-dimethylaminopyridine.

[0082] When a base is used in the reaction of compound (pt5) with compound (MA2), the amount of the base used is usually 0.1 mol or more and 50 mol or less, and preferably 0.5 mol or more and 30 mol or less, per 1 mol of compound (pt5).

[0083] The reaction temperature when reacting the compound (pt5) with the compound (MA2) is usually −100° C. or higher and 300° C. or lower. The reaction time when reacting the compound (pt5) with the compound (MA2) is usually 0.5 hours to 300 hours.

[0084] In addition, R 1 When is a hydrogen atom, compound (I) can be produced by reacting compound (pt4) with compound (MA2) instead of compound (pt5) without reacting compound (pt4) with compound (MA1).

[0085] After completion of each of the above reactions, the method for isolating the target compound is not particularly limited, and various known methods can be used. After isolation, the resulting residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the resulting compound can be analyzed using known analytical techniques and conditions. Examples of such analytical techniques include, but are not limited to, X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystallography can be performed, for example, in accordance with Chemistry of Materials, 2012, Vol. 24, pp. 4647-4652.

[0086] The content of compound (I) may be 100% by mass relative to the total amount of colorant (A), and the lower limit may be, for example, 0.1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 50% by mass or more.

[0087] <<Colorant (A1)>> The colorant (A) of the present invention may contain a dye (hereinafter sometimes referred to as dye (A1-1)) and / or a pigment (hereinafter sometimes referred to as pigment (A1-2)) other than compound (I) (hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more.

[0088] As the dye (A1-1), any known dye can be used as long as it does not contain compound (I), including solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used based on their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, and isoindoline dyes. Among these, organic solvent-soluble dyes are preferred.

[0089] Specifically, dyes with the following Color Index (CI) numbers are included: CI Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 177, 178, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 23 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 , 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166 6, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Dyes, such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, 6; CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive dyes, such as CI Reactive Red 36; CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes, such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; CI Vat Green 1; CI Vat Dyes, etc.

[0090] As the pigment (A1-2), any known pigment can be used as long as it does not contain compound (I), and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0091] Specific examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1, 7, 31, and 32;

[0092] When the colorant (A) contains the colorant (A1), the content of the colorant (A1) in the colorant (A) is, for example, 0.1 mass % or more and 99.9 mass % or less, and preferably 1 mass % or more and 50 mass % or less, relative to the total amount of the colorant (A).

[0093] When the colored resin composition contains a solvent (E), a colored composition containing the colorant (A) and the solvent (E) (hereinafter, sometimes referred to as a colorant-containing liquid) may be prepared in advance, and then the colored resin composition may be prepared using the colored composition. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the colored composition can be prepared by dispersing the colorant (A) in the solvent (E) and mixing them. The colored composition may contain part or all of the solvent (E) contained in the colored resin composition.

[0094] The solid content in the coloring composition is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, still more preferably 1% by mass or more and 90% by mass or less, particularly preferably 1% by mass or more and 80% by mass or less, even more preferably 1% by mass or more and 70% by mass or less, particularly preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less, relative to the total amount of the coloring composition.

[0095] The content of the colorant (A) in the coloring composition is 100% by mass or less, preferably 0.001% by mass or more and 99.999% by mass or less, more preferably 0.01% by mass or more and 99% by mass or less, even more preferably 0.1% by mass or more and 95% by mass or less, still more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1.0% by mass or more and 80% by mass or less, relative to the total amount of solids in the coloring composition.

[0096] The colorant (A) may be subjected, as necessary, to a rosin treatment, a surface treatment using a derivative having an acidic or basic group introduced therein, a graft treatment onto the surface of the colorant (A) using a polymer compound or the like, a micronization treatment using a sulfuric acid atomization method, a salt milling method or the like, a washing treatment using an organic solvent or water to remove impurities, a treatment to remove ionic impurities using an ion exchange method or the like, etc. The particle size of the colorant (A) is preferably approximately uniform.

[0097] The colorant (A) can be dispersed uniformly in the solution by adding a dispersant and carrying out a dispersion treatment. When two or more types of colorant (A) are used in combination, each may be dispersed individually, or multiple types may be mixed and dispersed.

[0098] Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), and BYK (registered trademark) (manufactured by BYK).

[0099] When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 3,000 parts by mass or less, and even more preferably 15 parts by mass or more and 1,000 parts by mass or less, relative to 100 parts by mass of the colorant (A) in the colored composition. When the amount of the dispersant used is within the above range, a colored composition in a more uniformly dispersed state tends to be obtained.

[0100] When a colored composition containing a colorant (A) and a solvent (E) is prepared in advance and then a colored resin composition is prepared using the colored composition, the colored composition may contain in advance a part or all, preferably a part, of the resin (B) contained in the colored resin composition. By preliminarily containing the resin (B), the dispersion stability of the colored composition can be further improved.

[0101] When the coloring composition contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 8,000 parts by mass or less, more preferably 0.01 parts by mass or more and 5,000 parts by mass or less, and even more preferably 0.1 parts by mass or more and 3,000 parts by mass or less, relative to 100 parts by mass of the colorant (A) in the coloring composition.

[0102] The content of colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, even more preferably 1.0% by mass or more and 30% by mass or less, and even more preferably 1.5% by mass or more and 20% by mass or less, based on the total amount of solids in the colored resin composition. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of resin (B) can be contained in the composition, a pattern with sufficient mechanical strength can be formed, which is preferable. Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0103] The content ratio of the colorant (A) to the resin (B) described later in the colored resin composition (resin (B) / colorant (A)) is, for example, preferably 2.0 or more, more preferably 3.0 or more, and even more preferably 4.0 or more, on a mass basis, and is preferably 20 or less, more preferably 15 or less, and even more preferably 13 or less.

[0104] <Resin (B)> Resin (B) is not particularly limited as long as it is different from a thermoplastic resin and can be used to form a photoresist, but is preferably an alkali-soluble resin, and more preferably an alkali-soluble resin having a carboxylic acid.

[0105] Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]: A copolymer having structural units derived from at least one monomer (a) (hereinafter, may be referred to as "(a)" or "monomer (a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter, may be referred to as "(b)" or "monomer (b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, may be referred to as "(c)" or "monomer (c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added and a structural unit derived from (c); Resin [K6]: A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride.

[0106] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids except fumaric acid and mesaconic acid; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl]; Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0107] Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0108] Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(b1)" or "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(b2)" or "monomer (b2)"), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(b3)" or "monomer (b3)").

[0109] Examples of the monomer (b1) include a monomer having a structure in which an unsaturated aliphatic hydrocarbon is epoxidized (hereinafter, may be referred to as "(b1-1)" or "monomer (b1-1)"), and a monomer having a structure in which an unsaturated alicyclic hydrocarbon is epoxidized (hereinafter, may be referred to as "(b1-2)" or "monomer (b1-2)").

[0110] As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred. Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis( glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, and the like.

[0111] Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., CELLOXIDE (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER (registered trademark) M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0112] [ka]

[0113] [In formula (BI) and formula (BII), R a and R b are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X a and X b are, independently of each other, a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c represents -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0114] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.

[0115] Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.

[0116] R a and R b Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0117] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

[0118] X a and X b Preferred examples of the alkyl group include a single bond, a methylene group, an ethylene group, a *-CH2-O- (* represents a bond to O) group, and a *-CH2CH2-O- group, and more preferred examples include a single bond and a *-CH2CH2-O- group (* represents a bond to O).

[0119] Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9) and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferred.

[0120] [ka]

[0121] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), and among these, preferred are compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15), and more preferred are compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15).

[0122] [ka]

[0123] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20, on a molar basis.

[0124] The monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond is preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group. Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0125] The monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond is preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0126] Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0] 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-8-yl(meth)acrylate (commonly known in the art as "dicyclopentenyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters such as decene-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[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 bicyclounsaturated compounds such as 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these, styrene, vinyltoluene, tricyclo[5.2.1.0] and cyclopentyl methyl ether are preferred from the viewpoint of copolymerization reactivity and heat resistance. 2,6 ]Decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decene-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and benzyl(meth)acrylate are preferred.

[0127] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K1] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting optical filter.

[0128] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0129] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer, such as the solvent described below as the solvent (E) for the colored resin composition of the present invention.

[0130] The obtained copolymer may be used as a solution after the reaction as it is, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) extracted by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for preparing the colored resin composition of the present invention, and therefore the manufacturing process of the colored resin composition of the present invention can be simplified.

[0131] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% Preferably, Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 60 mol% It is more preferable that: When the ratio of the structural units of the resin [K2] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance, heat resistance, and mechanical strength of the resulting optical filter.

[0132] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0133] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0134] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0135] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0136] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0137] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0138] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.

[0139] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.02,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, etc. [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, etc. [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Resins such as resins obtained by adding glycidyl (meth)acrylate to a (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid, resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymer with (meth)acrylic acid [K5]; and resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and further reacting tetrahydrophthalic anhydride with the resin [K6].

[0140] The resin (B) is more preferably the resin [K1] or the resin [K2], and particularly preferably the resin [K1].

[0141] The polystyrene-equivalent weight average molecular weight (Mw) of resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, and even more preferably from 3,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed area in a developer is high, and the resulting pattern tends to have high film retention and hardness. The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1.001 or more and 5 or less, and even more preferably 1.01 or more and 4 or less.

[0142] The acid value (solid content equivalent) of resin (B) is preferably 10 mg-KOH / g to 300 mg-KOH / g, more preferably 20 mg-KOH / g to 250 mg-KOH / g, even more preferably 25 mg-KOH / g to 200 mg-KOH / g, still more preferably 30 mg-KOH / g to 150 mg-KOH / g, and particularly preferably 60 mg-KOH / g to 135 mg-KOH / g. The acid value is measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0143] The content of resin (B) is preferably 5 to 98% by mass, more preferably 10 to 95% by mass, and even more preferably 15 to 93% by mass, based on 100% by mass of the solid content of the colored resin composition. When the colored resin composition contains a polymerizable compound (C) and a polymerization initiator (D), the content of resin (B) is preferably 5 to 90% by mass, more preferably 5 to 50% by mass, even more preferably 10 to 40% by mass, and even more preferably 15 to 35% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of resin (B) is within the above range, the solubility of the unexposed area in a developer tends to be high.

[0144] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0145] Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

[0146] Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0147] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylenediaminetetraacetic acid ester ... Examples of the dipentaerythritol tetra(meth)acrylate include ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0148] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, even more preferably 100 or more and 3,000 or less, still more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0149] The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and even more preferably 20% by mass or more and 70% by mass or less, relative to the total amount of solids in the colored resin composition.

[0150] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and known polymerization initiators can be used.

[0151] Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0152] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[ 9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. Furthermore, commercially available products such as Irgacure (registered trademark) OXE01 and OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may also be used as the O-acyloxime compound. Among these, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine.

[0153] Examples of the alkylphenone compound 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 alkylphenone compounds such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may also be used. Alkylphenone compounds also include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0154] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913).

[0155] Examples of 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-[2-(

[0033] 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.

[0156] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0157] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with a polymerization initiation aid (D1) (especially amines) described below.

[0158] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0159] The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of all resins (B) and polymerizable compounds (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0160] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D). When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0161] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0162] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. Alternatively, commercially available amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0163] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

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

[0165] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0166] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of all resins (B) and polymerizable compounds (C) contained in the colored resin composition.

[0167] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule but not -O-), ether solvents (solvents containing -O- in the molecule but not -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not -COO-), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

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

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

[0170] Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, and 2-ethoxy-2-methylpropionate. ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

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

[0172] Examples of alcohol 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 the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0175] As the solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, N-methylpyrrolidone, ethyl lactate and cyclohexanone are preferred.

[0176] When the solvent (E) is contained, the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 97% by mass or less, even more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 95% by mass or less, based on the total amount of the colored resin composition. In other words, the total amount of solids in the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 50% by mass or less, even more preferably 5% by mass or more and 30% by mass or less, and even more preferably 5% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and when a color filter is formed, the color density is not insufficient, so the display characteristics tend to be good.

[0177] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain.

[0178] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0179] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0180] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0181] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, relative to the total amount of the colored resin composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

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

[0183] <Method of producing colored resin composition> The colored resin composition can be prepared by mixing the colorant (A), the resin (B), the polymerizable compound (C) used as needed, the polymerization initiator (D), the solvent (E), the leveling agent (F), and other components. Mixing can be carried out using known or conventional equipment and conditions. The colorant (A) may be mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size becomes approximately 0.2 μm or less; it is preferable to use it in a dispersed state. In this case, the dispersant and part or all of the resin (B) may be blended as necessary. The colorant (A) may also be used in a state where it is dissolved in part or all of the solvent (E) in advance. The remaining components are mixed with the colorant-containing liquid obtained in this manner to achieve a predetermined concentration, thereby preparing the desired colored resin composition.

[0184] <Color filter manufacturing method> A color filter, which may be a color conversion layer, can be formed from the colored resin composition. Methods for forming a colored pattern include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography method involves applying the colored resin composition to a substrate, drying the composition to form a colored resin composition layer, and then exposing and developing the colored resin composition layer through a photomask. In the photolithography method, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and / or not developing the layer. Alternatively, the colored resin composition can be applied to a substrate, dried to form a colored resin composition layer, and then post-baked to form a colored coating film. The colored pattern or colored coating film thus formed is the color filter of the present invention.

[0185] The film thickness of the color filter to be produced is not particularly limited and can be adjusted appropriately depending on the purpose, application, etc., and is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0186] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates.

[0187] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, the colored resin composition is applied onto a substrate, and then dried by heating and drying (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth colored resin composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30° C. or higher and 120° C. or lower, and more preferably 50° C. or higher and 110° C. or lower. The heating time is preferably 10 seconds or higher and 60 minutes or lower, and more preferably 30 seconds or higher and 30 minutes or lower. When drying under reduced pressure is carried out, it is preferable to carry out the drying under a pressure of 50 Pa or more and 150 Pa or less at a temperature of 20°C or more and 25°C or less. The thickness of the colored resin composition layer is not particularly limited, and may be appropriately selected depending on the desired thickness of the color filter.

[0188] Next, the colored resin composition layer is exposed through a photomask to form a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended use is used. In addition, it is preferable to use an exposure device such as a mask aligner or a stepper, because it is possible to uniformly irradiate the entire exposure surface with parallel light and to accurately align the photomask with the substrate on which the colored resin composition layer is formed.

[0189] The light source used for exposure is preferably a light source that emits light with a wavelength of 250 nm or more and 450 nm or less. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0190] A colored pattern is formed on the substrate by contacting the exposed colored resin composition layer with a developer and developing it. The unexposed portions of the colored resin composition layer are dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant. The developing method may be any of a puddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be tilted at any angle during development. After development, the substrate is preferably washed with water.

[0191] Furthermore, the obtained colored pattern is preferably post-baked. The post-baking temperature is preferably 150° C. to 250° C., more preferably 160° C. to 240° C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes.

[0192] <Display device> The color filter is useful as a color filter for use in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, and particularly useful as a color filter for use in organic EL devices. [Example]

[0193] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and can of course be practiced with appropriate modifications within the scope of the above and below-described aims, all of which are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

[0194] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).

[0195] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0196] (Synthesis Example 1) 42 parts of acenaphthenequinone (manufactured by Tokyo Chemical Industry Co., Ltd.), 15 parts of malononitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), and 672 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Inc.) were mixed and stirred at 82°C for 6 hours. When the resulting mixture was cooled to 0°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was washed with 200 parts of acetonitrile and 400 parts of water. The resulting residue was dried under reduced pressure at 60°C to obtain 48 parts of the compound represented by formula (pt2) (yield 90%).

[0197] [ka]

[0198] <Identification of compound (pt2)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] +231 Exact Mass: 230

[0199] (Synthesis Example 2) 25 parts of the compound (pt2) obtained in Synthesis Example 1, 1.5 parts of potassium carbonate (Kanto Chemical Co., Inc.), 312 parts of acetonitrile (Kanto Chemical Co., Inc.), and 2 parts of water were mixed and stirred at 80°C for 5 hours. When the mixture was cooled to 0°C, a brown precipitate was formed. The mixture containing this brown precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 50 parts of acetonitrile. The resulting residue was dried under reduced pressure at 60°C and purified using a silica gel column (solvent: chloroform / ethyl acetate = 10 / 1, vol / vol), yielding 17 parts of a yellow-brown compound represented by formula (pt3) (yield 68%).

[0200] [ka]

[0201] <Identification of compound (pt3)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 231 Exact Mass: 230

[0202] (Synthesis Example 3) To 1.0 part of the compound (pt3) obtained in Synthesis Example 2, 5.6 parts of 98% sulfuric acid (Kanto Chemical Co., Inc.) was added, and the mixture was stirred at 50°C for 10 hours. The reaction solution was added dropwise to ice water, and the resulting residue was filtered. The resulting solid was washed with water, then washed with methanol, and dried under reduced pressure at 60°C to obtain 0.90 parts of the compound represented by formula (pt4) (yield 83%).

[0203] [ka]

[0204] <Identification of compound (pt4)> (Mass spectrometry) Ionization mode = ESI-: m / z = [MH] - 248 Exact Mass: 249

[0205] (Synthesis Example 4) 1.0 part of compound (pt4) obtained in Synthesis Example 3 was dissolved in 50 parts of N,N-dimethylformamide, and 0.5 parts of 1-hexylamine (Tokyo Chemical Industry Co., Ltd.) was added, followed by stirring at room temperature for 5 hours. The reaction solution was added dropwise to a mixed solvent of hexane and chloroform, and the resulting residue was filtered. The resulting solid was purified using an alumina column (solvent: tetrahydrofuran / water = 1 / 1, vol / vol) and dried under reduced pressure at 60°C to obtain 0.20 parts of a compound represented by formula (Ii-6) (hereinafter sometimes referred to as compound (Ii-6)) (yield 16%).

[0206] [ka]

[0207] <Identification of Compound (Ii-6)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 349 Exact Mass: 348

[0208] (Synthesis Example 5) 1.0 part of the compound (pt4) obtained in Synthesis Example 3, 3.1 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.4 parts of potassium carbonate (manufactured by Kanto Chemical Co., Inc.), and 50 parts of acetonitrile were mixed and stirred for 12 hours at 40° C. The reaction liquid was filtered through Celite, the filtrate was concentrated, and the resulting solid was purified on an alumina column (solvent: gradient from chloroform to acetonitrile) and dried under reduced pressure at 60° C. to obtain 0.56 parts of the compound represented by formula (pt5) (yield 47%).

[0209] [ka]

[0210] <Identification of compound (pt5)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] +278 Exact Mass: 277

[0211] (Synthesis Example 6) 0.20 parts of a compound represented by formula (Ii-83) (hereinafter sometimes referred to as compound (Ii-83)) was obtained (yield 18%) in the same manner as in Synthesis Example 4, except that 1.0 parts of compound (pt4) was replaced with 1.1 parts of compound (pt5) obtained in Synthesis Example 5, and 1.0 parts of 1-hexylamine was replaced with 0.9 parts of n-butylamine.

[0212] [ka]

[0213] <Identification of Compound (Ii-83)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 349 Exact Mass: 348

[0214] (Synthesis Example 7) 0.2 parts of a compound represented by formula (Ii-66) (hereinafter sometimes referred to as compound (Ii-66)) was obtained (yield 21%) in the same manner as in Synthesis Example 4, except that 1.0 parts of 1-hexylamine was changed to 1.1 parts of benzylamine.

[0215] [ka]

[0216] <Identification of Compound (Ii-66)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 355 Exact Mass: 354

[0217] (Synthesis Example 8) 0.1 part of a compound represented by formula (Ii-190) (hereinafter sometimes referred to as compound (Ii-190)) was obtained (yield 9%) in the same manner as in Synthesis Example 4, except that 1.0 part of 1-hexylamine was changed to 1.2 parts of diisobutylamine.

[0218] [ka]

[0219] <Identification of Compound (Ii-190)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 377 Exact Mass: 376

[0220] (Synthesis Example 9) Except for changing 1.0 parts of 1-hexylamine to 1.1 parts of piperidine, the same procedure as in Synthesis Example 4 was repeated to obtain 0.3 parts of a compound represented by formula (Ii-320) (hereinafter sometimes referred to as compound (Ii-320)) (yield 28%).

[0221] [ka]

[0222] <Identification of Compound (Ii-320)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 333 Exact Mass: 332

[0223] (Synthesis Example 10) The compound represented by the following formula (x) (hereinafter sometimes referred to as compound (x)) was synthesized in accordance with the description of Synthesis Example 2 in JP 2020-079397 A.

[0224] [ka]

[0225] (Synthesis Example 11) A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with nitrogen to replace the atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, followed by heating to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio) 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 dropwise addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution with a solids content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2×10 3 The resin B1 had a polydispersity of 2.08 and an acid value calculated as solid content of 77 mg-KOH / g.

[0226] [ka]

[0227] Example 1 (1) Preparation of coloring composition The following components were mixed to obtain colored composition 1. (A) Colorant: Compound (Ii-6) 2.6 parts (B) Resin: 54 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate (2) Preparation of colored resin composition Next, the following components were mixed to obtain a colored resin composition 1. Coloring composition 1 478 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts

[0228] (3) Preparation of colored coating film (color filter) The colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; manufactured by Corning Incorporated) so that the film thickness after post-baking would be 2 μm, and 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 80 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 After the light irradiation, the film was post-baked in an oven at 230° C. for 30 minutes to obtain a colored coating film. The thickness of the colored coating film was measured using DEKTAK3 (manufactured by Japan Vacuum Technology Co., Ltd.) The results are shown in Table 6.

[0229] (4) Contrast evaluation The contrast of the obtained colored coating film was measured using a contrast meter (CT-1: manufactured by Tsubosaka Electric Co., Ltd., color difference meter BM-5A: manufactured by Topcon Corporation, light source: F-10, polarizing film: manufactured by Tsubosaka Electric Co., Ltd.). The blank value during measurement was 30,000. If the contrast of the colored coating film is good, it can be said that the contrast of a colored pattern produced from the same colored resin composition is also good. The results are shown in Table 6.

[0230] (5) Heat resistance test The resulting colored coating film was heated in an oven under atmospheric conditions at 230°C for 120 minutes. The color difference ΔE*ab was calculated from the xy chromaticity coordinates (x, y) and Y measured values ​​before and after the test using the method described in JIS Z 8730:2009 (7. Calculation method for color difference). The smaller the color difference ΔE*ab, the smaller the color change. If ΔE*ab is 10 or less, the colored coating film can be considered to have no practical problems as a color filter. Furthermore, if the colored coating film has good heat resistance, it can be considered that a colored pattern made from the same colored resin composition also has good heat resistance. The results are shown in Table 7.

[0231] (6) Light resistance test An ultraviolet-cutting filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light below 380 nm) was placed on the resulting colored coating film, and the film was irradiated with xenon lamp light for 48 hours using a lightfastness tester (SUNTEST CPS+; manufactured by Toyo Seiki Co., Ltd.). The color difference ΔE*ab was calculated from the xy chromaticity coordinates (x, y) and Y measured before and after the test using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). The smaller the color difference ΔE*ab, the smaller the color change. If ΔE*ab is 10 or less, the colored coating film can be considered to be practically satisfactory as a color filter. Furthermore, if the colored coating film has good lightfastness, it can be said that a colored pattern produced from the same colored resin composition also has good lightfastness. The results are shown in Table 7.

[0232] <Comparative Example 1> A colored resin composition was prepared in the same manner as in Example 1, except that compound (Ii-6) in Example 1 was replaced with compound (x), and a colored coating film was produced and evaluated for contrast. The results are shown in Table 6.

[0233] [Table 6]

[0234] [Table 7]

[0235] The colored coating films obtained from the colored resin compositions prepared in the same manner as in Example 1, except that the compound represented by formula (Ii-6) was replaced with a compound represented by formula (Ii-83), formula (Ii-66), formula (Ii-190), or formula (Ii-320), all exhibited high contrast and high heat and light resistance, similar to Example 1.

Claims

1. A colored resin composition comprising a colorant and a resin, wherein the colorant comprises a compound represented by formula (I). 【Chemistry 1】 [In formula (I), R 1 ~R 3 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R 2 and R 3 may be taken together with the nitrogen atom to which they are attached to form a ring which may have a substituent. R 4 ~R 8 are each independently a hydrogen atom, -R 9 , -O-R 9 , -CO-O-R 9 , —O—CO—R 9 , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group. R 9 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R 9 When there are a plurality of groups, they may be the same or different.

2. The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator.

3. A color filter formed from the colored resin composition according to claim 1 or 2.

4. A display device comprising the color filter according to claim 3 .

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