Color-curing resin composition

Abstract

To provide a coloring curable resin composition useful for producing a color filter making contrast excellent.SOLUTION: A coloring curable resin composition that contains a coloring agent (A), a resin (B), a polymerizable compound (C) and a polymerization initiator (D) is such that: the coloring agent (A) contains a squarylium dye; an average ethylenic unsaturated group equivalent number of the polymerizable compound (C), represented by formula (1) is less than 96.0; and a content of the squarylium dye is 3-140 pts.mass based on 100 pts.mass of the polymerization initiator (D).SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are produced from colored curable resin compositions. In the examples of Patent Documents 1 and 2, dipentaerythritol hexaacrylate is mainly used as the polymerizable compound used in the colored curable resin compositions. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2020-055956 [Patent Document 2] Japanese Patent Application Publication No. 2019-163233 Summary of the Invention [Problem to be solved by the invention]

[0004] However, color filters formed from colored curable resin compositions containing dipentaerythritol hexaacrylate sometimes have insufficient contrast.

[0005] An object of the present invention is to provide a colored curable resin composition that is useful for producing a color filter with good contrast. [Means for solving the problem]

[0006] That is, the gist of the present invention is as follows. [1] A composition comprising a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), the colorant (A) comprises a squarylium dye; the polymerizable compound (C) has an average ethylenically unsaturated group equivalent number represented by formula (1) of less than 96.0, The colored curable resin composition has a content of the squarylium dye of 3 to 140 parts by mass relative to 100 parts by mass of the polymerization initiator (D). <Average Ethylenically Unsaturated Group Equivalents> Average ethylenically unsaturated group equivalent number of polymerizable compound (C) = ΣK i m i …(1) [In formula (1), K i : represents the value expressed as (molecular weight / number of ethylenically unsaturated bonds) of component i among all polymerizable compounds (C) contained in the colored curable resin composition. m i : represents the mole fraction of component i.] [2] The colored curable resin composition according to [1], wherein the squarylium dye comprises at least one selected from the group consisting of compounds represented by formula (I) and compounds represented by formula (III): [ka] [In formula (I), R 1 ~R 8 each independently represents a hydrogen atom, a halogen atom, a hydroxy group, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent. R 9 and R 10 each independently represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and a methylene group contained in the aliphatic hydrocarbon group may be replaced with -O-. R 11 and R 12 each independently represents a hydrocarbon group having 6 to 20 carbon atoms and an aromatic hydrocarbon ring, the hydrocarbon group may have a substituent, and a methylene group contained in the hydrocarbon group may be replaced with -O-. R 13represents a hydrogen atom or a saturated hydrocarbon group having 1 to 8 carbon atoms.] [ka] [In formula (III), R 31 ~R 38 each independently represents a hydrogen atom, a hydroxy group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms. R 39 ~R 42 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 39 ~R 42 At least one of R is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent, and R 39 ~R 42 At least one of the groups is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and a methylene group contained in the aliphatic hydrocarbon group may be replaced with -O-.] [3] The colored curable resin composition according to [1] or [2], wherein the average ethylenically unsaturated group equivalent number is 83.0 or more. [4] The colored curable resin composition according to any one of [1] to [3], wherein the polymerizable compound (C) includes a polymerizable compound having 3 to 5 ethylenically unsaturated bonds. [5] The colored curable resin composition according to any one of [1] to [4], wherein the polymerizable compound (C) includes at least one selected from pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and glycerin tri(meth)acrylate. [6] The colored curable resin composition according to any one of [1] to [5], wherein the polymerization initiator (D) contains an O-acyloxime compound. [7] A color filter formed from the colored curable resin composition according to any one of [1] to [6]. [8] A display device comprising the color filter according to [7]. [9] A solid-state imaging device comprising the color filter according to [7]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a colored curable resin composition that is useful for producing a color filter with good contrast. DETAILED DESCRIPTION OF THE INVENTION

[0008] The colored curable resin composition of the present invention contains a colorant (hereinafter may be referred to as colorant (A)), a resin (hereinafter may be referred to as resin (B)), a polymerizable compound (hereinafter may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter may be referred to as polymerization initiator (D)). The colorant (A) includes a squarylium dye. The colored curable resin composition of the present invention may contain a solvent (hereinafter, may be referred to as solvent (E)). The colored curable resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as components can be used alone or in combination unless otherwise specified.

[0009] <Colorant (A)> The colorant (A) includes a squarylium dye. The squarylium dye is not particularly limited and any known dye can be used.

[0010] The squarylium dye preferably includes a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)). Compound (I) includes the resonance structure of formula (I), and also includes compounds obtained by rotating each group in formula (I) or its resonance structure around the bond axis of the carbon-carbon single bond or carbon-nitrogen single bond.

[0011] [ka]

[0012] [In formula (I), R 1 ~R 8 each independently represents a hydrogen atom, a halogen atom, a hydroxy group, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent. R 9 and R 10 each independently represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and a methylene group contained in the aliphatic hydrocarbon group may be replaced with -O-. R 11 and R 12 each independently represents a hydrocarbon group having 6 to 20 carbon atoms and an aromatic hydrocarbon ring, the hydrocarbon group may have a substituent, and a methylene group contained in the hydrocarbon group may be replaced with -O-. R 13 represents a hydrogen atom or a saturated hydrocarbon group having 1 to 8 carbon atoms.]

[0013] R 1 ~R 8 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0014] R 1 ~R 8 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be linear, branched, or cyclic. Specific examples of the linear or branched saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, an isobutyl group, a butyl group, a tert-butyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a heptadecyl group, and an undecyl group. Examples of the cyclic saturated hydrocarbon group include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 1,2-dimethylcyclohexyl group, a cyclooctyl group, a 2,4,6-trimethylcyclohexyl group, and a 4-cyclohexylcyclohexyl group. R 1 ~R 8Examples of the substituent of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; a R b (R a and R b are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group or an ethoxy group; an alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and the like.

[0015] R 1 ~R 8 Examples of the alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include a group in which -O- is bonded to a bond of the saturated hydrocarbon group having 1 to 20 carbon atoms. Specific examples include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and a 2-ethylhexyloxy group. R 1 ~R 8 Examples of the substituent of the alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; c R d (R c and R d are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; an alkoxy group having 1 to 10 carbon atoms, such as a methoxy group or an ethoxy group; and an alkoxycarbonyl group in which the alkoxy moiety has 1 to 10 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group. R 1 ~R 8 The saturated hydrocarbon group represented by the formula (I) preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 7 carbon atoms, and even more preferably 1 to 4 carbon atoms. R 1 ~R 8The saturated hydrocarbon group represented by the formula (I) is preferably a linear or branched saturated hydrocarbon group, and more preferably a linear saturated hydrocarbon group.

[0016] R 1 ~R 8 Among them, R 1 ~R 4 is preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom. 1 ~R 4 is a hydrogen atom or a methyl group, more preferably R 1 ~R 4 is a hydrogen atom, R 5 ~R 8 are each independently preferably a hydrogen atom, a hydroxy group, a saturated hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, or an alkoxy group of 1 to 20 carbon atoms which may have a substituent, and more preferably a hydrogen atom or a hydroxy group.

[0017] R 1 ~R 8 (preferably R 5 ~R 8 ) are each independently a hydroxy group, and 1 ~R 8 (preferably R 5 ~R 8 ) are each independently a hydroxy group, and 1 ~R 8 (preferably R 5 ~R 8 ) are each independently a hydroxy group.

[0018] R 9 and R 10 The divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be saturated or unsaturated, preferably saturated. The divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear, branched, or cyclic, preferably linear or branched.

[0019] Examples of the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, a hexadecane-1,17-diyl group, a hexadecane-1,18-diyl group, a hexadecane-1,19-diyl group, a hexadecane-20-diyl group, a hexadecane-21-diyl group, a hexadecane-22-diyl group, a hexadecane-23-diyl group, a hexadecane-24-diyl group, a hexadecane-25-diyl group, a hexadecane-26-diyl group, a hexadecane-27-diyl group, a hexadecane-28-diyl group, a hexadecane-29-diyl group, a hexadecane-30-diyl group, a hexadecane-31-diyl group, a hexadecane-32-diyl group, a hexadecane-33-diyl group, a hexadecane-34-diyl group, a hexadecane-35-diyl group, a hexadecane-36-diyl group, a hexade divalent linear aliphatic hydrocarbon groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2,2-dimethylpropane-1,3-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl groups. The cyclic divalent aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic divalent aliphatic hydrocarbon group include monocyclic divalent aliphatic hydrocarbon groups such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; and polycyclic divalent aliphatic hydrocarbon groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl. R 9 and R 10 The divalent aliphatic hydrocarbon group represented by the following formula preferably has 1 to 10 carbon atoms, more preferably 1 to 7 carbon atoms, and even more preferably 1 to 4 carbon atoms. R 9 and R 10 The divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably a saturated linear or branched aliphatic hydrocarbon group, and more preferably a saturated linear aliphatic hydrocarbon group. R 9 and R 10The divalent aliphatic hydrocarbon groups represented by the following formula may be the same or different, but are preferably the same.

[0020] A methylene group contained in the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms may be replaced with -O-. Examples of the divalent aliphatic hydrocarbon group in which a methylene group contained in the group is replaced with -O- include groups represented by the following formula: In the following formula, the * on the left represents a bond to the nitrogen atom, and the * on the right represents a bond to the oxygen atom.

[0021] [ka]

[0022] R 9 and R 10 The divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have a substituent, and examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; e R f (R e and R f are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; an alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and the like. Among them, R 9 and R 10 The divalent aliphatic hydrocarbon group represented by the formula (I) is preferably a methylene group, an ethylene group, a propane-1,3-diyl group, or a butane-1,4-diyl group.

[0023] R 11 and R 12 Examples of the hydrocarbon group having 6 to 20 carbon atoms and an aromatic hydrocarbon ring represented by the formula (I) include a group having a bond on the aromatic hydrocarbon ring (hereinafter referred to as an aromatic hydrocarbon group), an aralkyl group having 7 to 20 carbon atoms, etc. These may have a substituent. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, with a benzene ring being preferred. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a tolyl group, a xylyl group, a dimethylethylphenyl group, a dimethylpropylphenyl group, a dimethylbutylphenyl group, a trimethylphenyl group, and a diisopropylphenyl group. Among these, an aromatic hydrocarbon group having an alkyl group at the ortho position is preferred, and examples thereof include a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,6-diisopropylphenyl group, a 2,6-dimethyl-4-ethylphenyl group, a 2,6-dimethyl-4-propylphenyl group, and a 2,6-dimethyl-4-butylphenyl group. Furthermore, a bulky alkyl group at the ortho position tends to result in excellent light resistance. When the aromatic hydrocarbon group has a substituent, it may have one or more of the substituents. When the aromatic hydrocarbon group has multiple substituents, the substituents may be the same or different. Examples of the substituent include a hydroxy group; a carboxy group; a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, or a bromine atom; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group or an ethoxy group; a sulfamoyl group; an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group; an alkoxycarbonyl group having 1 to 6 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and the like. The hydrocarbon group having 6 to 20 carbon atoms and an aromatic hydrocarbon ring may have a substituent such as a hydroxy group, a carboxy group, a halogen atom, or an alkoxy group, and preferably has a hydroxy group.

[0024] When the aromatic hydrocarbon group which may have a substituent has a methylene group, the methylene group may be replaced with —O—.

[0025] Examples of the aralkyl group having 7 to 20 carbon atoms include a group in which an alkanediyl group having 1 to 5 carbon atoms, such as a methylene group, an ethylene group, or a propylene group, is bonded to the aromatic hydrocarbon ring described above for the aromatic hydrocarbon group. Examples of the aralkyl group include a benzyl group, a phenylethyl group, a naphthylmethyl group, and a naphthylethyl group. The aralkyl group having 7 to 20 carbon atoms may have a substituent, and when there are multiple substituents, the respective substituents may be the same or different. The substituent may be bonded to the aromatic hydrocarbon ring or the alkanediyl group, and examples of the substituent that can be bonded to the aromatic hydrocarbon ring are the same as those described above as the substituents of the aromatic hydrocarbon group.

[0026] When the aralkyl group having 7 to 20 carbon atoms which may have a substituent has a methylene group, the methylene group may be replaced with —O—.

[0027] R 11 and R 12 The hydrocarbon groups having 6 to 20 carbon atoms and having an aromatic hydrocarbon ring represented by the formula (I) may be the same or different, but are preferably the same. Among them, R 11 and R 12The hydrocarbon group having 6 to 20 carbon atoms and an aromatic hydrocarbon ring represented by the formula (I) is preferably a dimethylethylphenyl group, a dimethylpropylphenyl group, a dimethylbutylphenyl group, a dimethylmethoxyphenyl group, a dimethylethoxyphenyl group, or a dimethylpropoxyphenyl group, more preferably a 2,6-dimethyl-4-ethylphenyl group, a 2,6-dimethyl-4-propylphenyl group, a 2,6-dimethyl-4-butylphenyl group, a 2,6-dimethyl-4-methoxyphenyl group, a 2,6-dimethyl-4-ethoxyphenyl group, or a 2,6-dimethyl-4-propoxyphenyl group, even more preferably a 2,6-dimethyl-4-methoxyphenyl group, a 2,6-dimethyl-4-ethoxyphenyl group, or a 2,6-dimethyl-4-propoxyphenyl group, and still more preferably a 2,6-dimethyl-4-ethoxyphenyl group. Furthermore, the ethyl, propyl, butyl, methoxy, ethoxy, or propoxy group preferably has a hydroxy group as a substituent.

[0028] R 13 The saturated hydrocarbon group having 1 to 8 carbon atoms represented by the formula (I) may be linear, branched, or cyclic. Specific examples of the linear or branched saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, an isobutyl group, a butyl group, a tert-butyl group, a hexyl group, a heptyl group, and an octyl group. Examples of the cyclic saturated hydrocarbon group include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 1,2-dimethylcyclohexyl group, and a cyclooctyl group. Among them, R 13 is particularly preferably a hydrogen atom.

[0029] Examples of compound (I) include compounds represented by formulae (I-1) to (I-240) shown in Tables 1 to 3.

[0030] [Table 1]

[0031] [Table 2]

[0032] [Table 3]

[0033] In Tables 1 to 3, A1-1 to A1-4 represent groups represented by the following formulae: In the following formulae, the * on the left represents a bond to the nitrogen atom, and the * on the right represents a bond to the oxygen atom.

[0034] [ka]

[0035] In Tables 1 to 3, A2-1 to A2-5 represent groups represented by the following formulae: In the following formulae, * represents a bond.

[0036] [ka]

[0037] Compound (I) includes not only the compounds represented by the above formulas (I-1) to (I-240) but also the compound represented by the following formula (II) (hereinafter sometimes referred to as compound (II)), and compound (II) is preferred. Compound (II) has good light resistance.

[0038] [ka]

[0039] [In formula (II), R 1 ~R 10 represents the same meaning as in formula (I). X 1 and X 2each independently represents a hydrocarbon group having 1 to 14 carbon atoms having at least one group selected from the group consisting of a hydroxy group and a carboxy group, a hydroxy group, or a carboxy group, and a methylene group contained in the hydrocarbon group may be replaced with -O-. R 14 and R 15 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 13 carbon atoms. n1 and n2 each independently represent an integer of 1 to 5. However, (X 1 ) n1 and (R 14 ) 5-n1 The total number of carbon atoms in (X 2 ) n2 and (R 15 ) 5-n2 The total number of carbon atoms in each is 14 or less.

[0040] X 1 and X 2 Examples of the hydrocarbon group having 1 to 14 carbon atoms represented by the formula include aliphatic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups. Examples of the straight-chain aliphatic hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. Examples of the branched aliphatic hydrocarbon group include an isopropyl group, a sec-butyl group, a tert-butyl group, a methylpentyl group, an ethylpentyl group, a methylhexyl group, an ethylhexyl group, a propylhexyl group, and a tert-octyl group, and preferably an isopropyl group, a sec-butyl group, a tert-butyl group, and an ethylhexyl group. Examples of the cyclic aliphatic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a norbornyl group, and an adamantyl group. Examples of aromatic hydrocarbon groups include a phenyl group, a naphthyl group, an anthryl group, a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Examples of groups combining these groups include alkylcycloalkyl groups, cycloalkylalkyl groups, and aralkyl groups. X 1 and X 2 The hydrocarbon group having 1 to 14 carbon atoms represented by the formula (I) preferably has 1 to 10 carbon atoms, more preferably 1 to 7 carbon atoms, and even more preferably 1 to 4 carbon atoms. X 1 and X 2 The hydrocarbon group having 1 to 14 carbon atoms represented by the formula (I) is preferably a linear or branched aliphatic hydrocarbon group, more preferably a linear aliphatic hydrocarbon group, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group. X 1 and X 2 The hydrocarbon groups having 1 to 14 carbon atoms represented by the formula (I) may be the same or different, but are preferably the same. X 1 and X 2 are preferably each independently a hydrocarbon group having 1 to 10 carbon atoms and having at least one group selected from the group consisting of a hydroxy group and a carboxy group, X 1 and X 2 are more preferably each independently a hydrocarbon group having 1 to 7 carbon atoms and having at least one group selected from the group consisting of a hydroxy group and a carboxy group, X 1 and X 2 are more preferably each independently a hydrocarbon group having 1 to 4 carbon atoms and having at least one group selected from the group consisting of a hydroxy group and a carboxy group, X 1 and X 2 and are each independently a hydrocarbon group having 1 to 4 carbon atoms and a hydroxy group.

[0041] The methylene group contained in the hydrocarbon group having 1 to 14 carbon atoms may be replaced with —O—.

[0042] R 14 and R 15 The hydrocarbon group having 1 to 13 carbon atoms represented by the formula: 1 and X 2 Examples of the hydrocarbon group having 1 to 14 carbon atoms include the same groups as those described above as represented by the following formula: R 14 and R 15 may be the same or different, but are preferably the same. Among them, R 14 and R 15 is particularly preferably a hydrogen atom.

[0043] n1 and n2 each independently represent an integer of 1 to 5, more preferably 1 or 2, and even more preferably 1.

[0044] (X 1 ) n1 and (R 14 ) 5-n1 The total number of carbon atoms in (X 2 ) n2 and (R 15 ) 5-n2 The total number of carbon atoms in each of X is 14 or less. 1 , X 2 , R 14 and R 15 If there are multiple X 1 , X 2 , R 14 and R 15 may be the same or different.

[0045] Compound (II) includes compounds represented by the following formula (II-a), and specific examples include compounds represented by formulas (II-1) to (II-540) shown in Tables 4 to 12.

[0046] [ka]

[0047] [Table 4]

[0048] [Table 5]

[0049] [Table 6]

[0050] [Table 7]

[0051] [Table 8]

[0052] [Table 9]

[0053] [Table 10]

[0054] [Table 11]

[0055] [Table 12]

[0056] In Tables 4 to 12, A1-1 to A1-4 represent the same groups as above.

[0057] In Tables 4 to 12, A3-1 to A3-3 represent groups represented by the following formulae: In the following formulae, * represents a bond. [ka]

[0058] In Tables 4 to 12, A4-1 to A4-3 represent groups represented by the following formulae: In the following formulae, * represents a bond. [ka]

[0059] Each of the compounds represented by formulas (I), (II), and (II-a) preferably has 2 to 10, more preferably 3 to 9, and even more preferably 4 to 8 hydroxy groups.

[0060] Compound (I) includes: Compounds represented by formula (I-1) to formula (I-180), formula (II-121) to formula (II-180), and formula (II-331) to formula (II-375) are preferred; Compounds represented by formulae (I-25) to (I-36), (I-85) to (I-96), (I-145) to (I-156), (I-169) to (I-181), (II-121) to (II-150), and (II-361) to (II-375) are more preferred, The compounds represented by formulae (II-133) to (II-135) are more preferred, and the compound represented by formula (II-135) is particularly preferred.

[0061] The compound represented by formula (I) can be synthesized, for example, by the method described in JP-A-2020-055956.

[0062] The squarylium dye preferably includes a compound represented by formula (III) (hereinafter, sometimes referred to as compound (III)). Compound (III) includes the resonance structure of formula (III), and also includes compounds obtained by rotating each group in formula (III) or its resonance structure around the bond axis of the carbon-carbon single bond or carbon-nitrogen single bond.

[0063] [ka]

[0064] [In formula (III), R 31 ~R 38 each independently represents a hydrogen atom, a hydroxy group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms. R 39 ~R 42 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 39 ~R 42 At least one of R is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent, and R 39 ~R 42 At least one of the groups is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and a methylene group contained in the aliphatic hydrocarbon group may be replaced with -O-.]

[0065] R 31 ~R 38The alkyl group having 1 to 20 carbon atoms represented by the formula (I) may be linear, branched, or cyclic. Specific examples of linear or branched alkyl groups include methyl, ethyl, propyl, isobutyl, butyl, tert-butyl, hexyl, heptyl, octyl, nonyl, decyl, heptadecyl, and undecyl. Examples of cyclic alkyl groups include cyclopropyl, 1-methylcyclopropyl, cyclopentyl, cyclohexyl, 1,2-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, and 4-cyclohexylcyclohexyl. R 31 ~R 38 Examples of the substituent of the alkyl group having 1 to 20 carbon atoms represented by the formula (I) include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; k R l (R k and R l are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group or an ethoxy group; an alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and the like.

[0066] R 31 ~R 38 Examples of the alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include a group in which -O- is bonded to a bond of the alkyl group having 1 to 20 carbon atoms. Specific examples include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and a 2-ethylhexyloxy group. R 31 ~R 38 Examples of the substituent of the alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; m R n (R m and R nare each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group or an ethoxy group; an alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and the like. R 31 ~R 38 The alkyl group and alkoxy group having 1 to 20 carbon atoms represented by the formula (I) preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 5 carbon atoms.

[0067] R 31 ~R 38 Among them, R 31 ~R 34 is particularly preferably a hydrogen atom. 35 ~R 38 are each independently preferably a hydrogen atom, a hydroxy group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms, more preferably a hydrogen atom or a hydroxy group.

[0068] R 31 ~R 38 (preferably R 35 ~R 38 ) are each independently a hydroxy group, and 31 ~R 38 (preferably R 35 ~R 38 ) are each independently a hydroxy group, and 31 ~R 38 (preferably R 35 ~R 38 ) are each independently a hydroxy group.

[0069] R 39 ~R 42 Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by the formula include an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms.

[0070] The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be saturated or unsaturated, preferably saturated, and may be linear, branched, or cyclic, preferably linear or branched.

[0071] Examples of linear or branched aliphatic hydrocarbons having 1 to 20 carbon atoms include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, and 2-propenyl (allyl) groups; and branched aliphatic hydrocarbon groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 5. The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The number of carbon atoms in the cyclic aliphatic hydrocarbon group is preferably 3 to 8, and more preferably 3 to 6.

[0072] A methylene group contained in the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be replaced with -O-. Examples of the group in which a methylene group contained in the aliphatic hydrocarbon group is replaced with -O- include groups represented by the following formula: In the following formula, * represents a bond.

[0073] [ka]

[0074] Examples of aromatic hydrocarbon groups having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 16, more preferably 6 to 12, and even more preferably 6 to 9.

[0075] R 39 ~R 42 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have a substituent, and examples of the substituent include a carboxy group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group or an ethoxy group; a hydroxy group; a sulfamoyl group; and an alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group.

[0076] R 39 ~R 42 At least one of the above is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent. The aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent preferably has 1 to 2 carboxy groups, and more preferably 1 carboxy group. The carboxy group is desirably bonded to at least the terminal of the aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent. Examples of such aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent include groups represented by the following formula: In the following formula, * represents a bond.

[0077] [ka]

[0078] R 39 ~R 42 At least one of the groups is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferably a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, or a phenyl group having two halogen atoms as substituents, such as a 2,4-difluorophenyl group, a 2,4-dichlorophenyl group, a 2,4-dibromophenyl group, or a 2,4-diiodophenyl group, and more preferably a 2,4-dimethylphenyl group, a 2,4,6-trimethylphenyl group, or a 2,4-difluorophenyl group.

[0079] In compound (III), R 39 and R 42 are each independently an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent, and R 40 and R 41 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, R 39 and R 42 are each independently an aliphatic hydrocarbon group having 1 to 10 carbon atoms and having a carboxy group as a substituent, and R 40 and R 41 are each independently an aromatic hydrocarbon group having 6 to 16 carbon atoms which may have a substituent, R 39 and R 42 are each independently an aliphatic hydrocarbon group having 1 to 8 carbon atoms and having a carboxy group as a substituent, and R 40 and R 41 are each independently an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, R 39 and R 42 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms and having a carboxy group as a substituent, and R 40 and R 41 are each independently an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have a substituent. Compound (III) preferably has 2 to 4 hydroxy groups and 2 to 4 carboxy groups, more preferably 2 to 3 hydroxy groups and 2 to 3 carboxy groups, and even more preferably 2 hydroxy groups and 2 carboxy groups.

[0080] Examples of compound (III) include compounds represented by formulae (III-1) to (III-180) shown in Tables 13 to 15. Compound (III) is Preferred are compounds represented by formulas (III-1) to (III-90) and formulas (III-121) to (III-180), More preferably, the compounds are represented by formulas (III-1) to (III-30) and formulas (III-121) to (III-150). More preferred are compounds represented by formulas (III-1) to (III-3), (III-19) to (III-21), and (III-127) to (III-129), Even more preferred are the compounds represented by formulae (III-1) to (III-3), and particularly preferred is the compound represented by formula (III-3).

[0081] [Table 13]

[0082] [Table 14]

[0083] [Table 15]

[0084] In Tables 13 to 15, ph1 to ph10 represent groups represented by the following formulae (* represents a bond).

[0085] [ka]

[0086] In Tables 13 to 15, ca1 to ca6 represent groups represented by the following formulae (* represents a bond).

[0087] [ka]

[0088] The compound represented by formula (III) can be synthesized, for example, by the method described in JP-A-2019-163233.

[0089] The squarylium dye preferably contains at least one selected from the group consisting of compound (I) and compound (III).

[0090] The content of compound (I) and compound (III) is preferably 0.1 to 150 parts by mass, more preferably 0.3 to 100 parts by mass, and even more preferably 0.5 to 50 parts by mass, relative to 100 parts by mass of resin (B).

[0091] The content of compound (I) and compound (III) in the total amount of colorant (A) is preferably 20% by mass or more, more preferably 50% by mass or more, even more preferably 80% by mass or more, and particularly preferably 90% by mass or more.

[0092] The content of the squarylium dye is 3 to 140 parts by mass, more preferably 5 to 130 parts by mass, and even more preferably 10 to 120 parts by mass, relative to 100 parts by mass of the polymerization initiator (D). Within this range, a color filter with good contrast can be obtained. Furthermore, when the squarylium dye is compound (I) (including compound (II)), the content of compound (I) is preferably 3 to 140 parts by mass, more preferably 18 to 135 parts by mass, even more preferably 50 to 130 parts by mass, and even more preferably 90 to 125 parts by mass, relative to 100 parts by mass of the polymerization initiator (D). When the squarylium dye is compound (I), the contrast tends to improve as the content of compound (I) relative to the polymerization initiator (D) increases. When the squarylium dye is compound (III), the content of compound (III) is preferably 3 to 140 parts by mass, more preferably 18 to 135 parts by mass, even more preferably 50 to 130 parts by mass, and still more preferably 90 to 125 parts by mass, relative to 100 parts by mass of the polymerization initiator (D). When the squarylium dye is compound (III), the contrast tends to improve as the content of compound (III) relative to the polymerization initiator (D) increases.

[0093] In addition to compounds (I) and (III), colorant (A) may contain a colorant different from compounds (I) and (III). The colorant different from compounds (I) and (III) may be either a dye (hereinafter sometimes referred to as dye (A1)) or a pigment (hereinafter sometimes referred to as pigment (A2)). The colorant different from compounds (I) and (III) may contain one or both of these dyes (A1) and pigments (A2).

[0094] The dye (A1) is not particularly limited, and known dyes can be used as long as they do not contain compounds (I) and (III). Examples of such dyes include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of such dyes include compounds classified as non-pigment dyes with hues 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, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes (excluding compounds (I) and (III)), acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

[0095] Specifically, CI Solvent Yellow 4 (hereinafter, the notation CI Solvent Yellow will be omitted and only the numbers will be listed), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; 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, 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, 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, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324, 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, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; 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, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, and 60; 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; Examples include CI Vat dyes such as CI Vat Green 1. These dyes may be appropriately selected in accordance with the desired spectral spectrum of the color filter.

[0096] The pigment (A2) is not particularly limited and any known pigment can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of 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, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, and 214; 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, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, and 58; Brown pigments such as CI Pigment Brown 23 and 25; Examples include black pigments such as CI Pigment Black 1 and 7.

[0097] The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, a graft treatment onto the pigment surface using a polymer compound or the like, a microparticle treatment using a sulfuric acid microparticle 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, or the like. The pigment preferably has a uniform particle size. By adding a pigment dispersant and carrying out a dispersion treatment, it is possible to obtain a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution.

[0098] Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Corporation), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie). When a pigment dispersant is used, the amount thereof is preferably from 1 to 100% by mass, more preferably from 5 to 50% by mass, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is within this range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

[0099] The content of the colorant (A) in the colored curable resin composition is preferably 0.1 mass % or more and 70 mass % or less, more preferably 0.5 mass % or more and 60 mass % or less, and even more preferably 1 mass % or more and 50 mass % or less, relative to the total amount of solids. The content of the squarylium dye in the colored curable resin composition is preferably 0.1% by mass or more and 40% by mass or less, more preferably 0.5% by mass or more and 30% by mass or less, and even more preferably 1% by mass or more and 20% by mass or less, relative to the total amount of solids. When the contents of the colorant (A) and the squarylium dye are within the above ranges, the color density when formed into a color filter is sufficient, and the composition can contain the resin (B) and the polymerizable compound (C) in the required amounts, so that a pattern with sufficient mechanical strength can be formed.

[0100] Here, the "total amount of solids" in this specification refers to the amount obtained by excluding the content of the solvent from the total amount of the colored curable 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.

[0101] <Resin (B)> Resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having structural units derived from at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "monomer (a)"). Resin (B) is preferably a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b)"), and other structural units. Examples of other structural units include structural units derived from a monomer copolymerizable with monomer (a) (however, different from monomer (a) and monomer (b); hereinafter, this may be referred to as "monomer (c)"), structural units having an ethylenically unsaturated bond, etc.

[0102] 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.

[0103] 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-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like.

[0104] Among these, acrylic acid, methacrylic acid, o-, m-, p-vinylbenzoic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.

[0105] 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. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0106] Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)").

[0107] Examples of the monomer (b1) include a monomer having a structure in which a linear or branched unsaturated aliphatic hydrocarbon has been epoxidized (hereinafter, this may be referred to as "monomer (b1-1)") and a monomer having a structure in which an unsaturated alicyclic hydrocarbon has been epoxidized (hereinafter, this may be referred to as "monomer (b1-2)").

[0108] The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. 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(glycidyl ether), Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0109] 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).

[0110] [ka]

[0111] [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.]

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] X a and X bPreferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0117] 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.

[0118] [ka]

[0119] 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).

[0120] [ka]

[0121] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20 on a molar basis.

[0122] As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. 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.

[0123] The monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Ltd.), tetrahydrofurfuryl methacrylate, and the like.

[0124] The monomer (b) is preferably the monomer (b1) in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, the monomer (b1-2) is more preferable in that it provides excellent storage stability of the colored composition.

[0125] 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; Halogen atom-containing (meth)acrylic acid esters such as 2,2,3,3,4,4,5,5-octafluoropentyl (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, 9-vinylcarbazole, 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, phenyl(meth)acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl(meth)acrylate, 9-vinylcarbazole, benzyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, and 2-ethylhexyl(meth)acrylate are preferred.

[0126] 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 (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl (meth)acrylate / 9-vinylcarbazole / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] Decyl (meth)acrylate / phenyl (meth)acrylate / o-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / m-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / p-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate / 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / Tricyclo[5.2.1.0 2,6] decenyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and resins described in JP-A Nos. 9-106071, 2004-29518, and 2004-361455. Among these, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).

[0127] Resin (B) may be a combination of two or more kinds. In this case, resin (B) contains at least It is preferable that the composition contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), more preferably, the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1); It is more preferable that the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2), 3,4-Epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] It is even more preferable that the copolymer contains one or more selected from the group consisting of decyl (meth)acrylate / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymers.

[0128] 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, even more preferably from 3,000 to 30,000, and still more preferably from 5,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed areas in a developer is high, and the resulting pattern tends to have high film retention and hardness.

[0129] 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 or more and 5 or less, and even more preferably 1 or more and 4 or less.

[0130] 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 180 mg-KOH / g, and particularly preferably 40 mg-KOH / g to 150 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.

[0131] The content of resin (B) is preferably 5 to 90 mass%, more preferably 10 to 80 mass%, even more preferably 13 to 70 mass%, and still more preferably 15 to 60 mass%, relative to 100 mass% of the solid content of the colored curable 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.

[0132] <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.

[0133] The average ethylenically unsaturated group equivalent number of the polymerizable compound (C) is less than 96.0. As a result of investigations by the present inventors, it has been found that if the average ethylenically unsaturated group equivalent number exceeds the above range, the contrast of the color filter deteriorates. The average ethylenically unsaturated group equivalent number of the polymerizable compound (C) is preferably 95.5 or less, more preferably 95.0 or less, even more preferably 94.5 or less, and even more preferably 94.0 or less. Although there is no particular lower limit, the average ethylenically unsaturated group equivalent number of the polymerizable compound (C) is preferably 83.0 or more, more preferably 83.5 or more, even more preferably 84.0 or more, even more preferably 84.5 or more, and particularly preferably 85.0 or more. The average ethylenically unsaturated group equivalent number of the polymerizable compound (C) is calculated by the formula (1).

[0134] <Average Ethylenically Unsaturated Group Equivalents> The average ethylenically unsaturated group equivalent number of the polymerizable compound (C) is represented by formula (1). Average ethylenically unsaturated group equivalent number of polymerizable compound (C) = ΣK i m i …(1) [In formula (1), K i : represents the value expressed as (molecular weight / number of ethylenically unsaturated bonds) of component i among all polymerizable compounds (C) contained in the colored curable resin composition. m i : represents the mole fraction of component i.]

[0135] The polymerizable compound (C) preferably contains a polymerizable compound having three or more (preferably five or less, more preferably four or less) ethylenically unsaturated bonds. Any polymerizable compound can be used as the polymerizable compound as long as the average ethylenically unsaturated group equivalent number of the polymerizable compound (C) is less than 96.0. Examples of the polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, glycerin tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, and tetrapentaerythritol hexa(meth)acrylate. Examples of the acrylate include thritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Among these, the polymerizable compound (C) preferably contains at least one selected from pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and glycerin tri(meth)acrylate, and more preferably contains at least one selected from pentaerythritol triacrylate, pentaerythritol tetraacrylate, and glycerin triacrylate.

[0136] The polymerizable compound (C) may be a combination of two or more of the above-exemplified compounds, or may be a combination of pentaerythritol tri(meth)acrylate and pentaerythritol tetra(meth)acrylate.

[0137] When pentaerythritol tri(meth)acrylate and pentaerythritol tetra(meth)acrylate are combined, the ratio (x:y) of pentaerythritol tri(meth)acrylate (x) to pentaerythritol tetra(meth)acrylate (y) is preferably 1 to 99 mol%:99 to 1 mol%, more preferably 10 to 90 mol%:90 to 10 mol%, even more preferably 20 to 80 mol%:80 to 20 mol%, and still more preferably 30 to 70 mol%:70 to 30 mol%.

[0138] The content of the polymerizable compound (C) is preferably 1 to 65 mass% relative to the total amount of solids, more preferably 5 to 60 mass%, even more preferably 10 to 55 mass%, and even more preferably 15 mass% or more, 20 mass% or more, or 25 mass% or more. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved. Furthermore, when the content is higher within the above range, the contrast tends to be further improved.

[0139] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.

[0140] Examples of the O-acyloxime compound include O-acyloxime compounds having a diphenyl sulfide skeleton such as 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, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine; N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-one-2-imine; O-acyloxime compounds having a carbazole skeleton such as 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; and O-acyloxime compounds having a fluorene skeleton such as 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyloxime. Commercially available products such as Irgacure (registered trademark) OXE01 and OXE02 (all manufactured by BASF), PBG-327 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), N-1919 (manufactured by ADEKA Corporation), and DFI-091 (manufactured by Daito ChemiX Co., Ltd.) may also be used.Among them, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, and 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyloxime. These O-acyloxime compounds tend to produce color filters with high brightness.

[0141] 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, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, 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. Commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may also be used.

[0142] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0143] 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.

[0144] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) 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-48-38403 and JP-A-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-7-10913).

[0145] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.

[0146] 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, benzil, methyl phenylglyoxylate, and titanocene compounds.

[0147] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an O-acyloxime compound, an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0148] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 205 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0149] The content of the polymerization initiator (D) is preferably 1 to 70 parts by mass, more preferably 2 to 65 parts by mass, even more preferably 3 to 60 parts by mass, and even more preferably 55 parts by mass or less, 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, 35 parts by mass or less, 30 parts by mass or less, or 25 parts by mass or less, relative to 100 parts by mass of the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, contrast tends to be improved, and when it is reduced within the above range, contrast tends to be further improved.

[0150] The content of the polymerization initiator (D) is preferably 0.1 to 30% by mass, more preferably 0.5 to 25% by mass, even more preferably 1 to 20% by mass, and even more preferably 15% by mass or less, or 10% by mass or less, based on the total amount of solids. When the content of the polymerization initiator (D) is within the above range, the contrast tends to improve, and when it is reduced within the above range, the contrast tends to improve further.

[0151] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0152] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0153] 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.

[0154] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0155] 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.

[0156] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.

[0157] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0158] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0159] 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.

[0160] 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, methyl 2-ethoxy ... Examples of the alkyl ether acetate include ethyl 2-methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0161] 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.

[0162] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0163] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0164] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0165] Among the above solvents, from the viewpoints of coatability and drying property, organic solvents having a boiling point at 1 atm of 120° C. or higher and 180° C. or lower are preferred. Preferred solvents are propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferred are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate.

[0166] The content of the solvent (E) is preferably 70 to 95 mass%, more preferably 75 to 92 mass%, based on the total amount of the colored curable resin composition of the present invention. In other words, the total content of the solids in the colored curable resin composition is preferably 5 to 30 mass%, more preferably 8 to 25 mass%. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

[0167] <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. 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 (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).

[0168] Examples of the fluorine-based surfactant 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.).

[0169] Examples of the silicone surfactant having a fluorine atom 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).

[0170] The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002% by mass or more and 0.2% by mass or less, and even more preferably 0.005% by mass or more and 0.2% by mass or less, relative to the total amount of the colored curable resin composition. Note that this content does not include the content of the dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0171] <Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as a polymerization initiation aid, a filler, another polymer compound, an adhesion promoter, a light stabilizer, and a chain transfer agent, as necessary. Adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-sulfur Examples thereof include phenylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropyltriethoxysilane.

[0172] <Method for producing colored curable resin composition> The colored curable resin composition can be prepared, for example, by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and, if necessary, the solvent (E), the leveling agent (F), the polymerization initiation aid (D1), and other components. The colorant (A) may be contained in advance in a pigment dispersion liquid. The desired colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid to a predetermined concentration. When a dye is contained, the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution, which is preferably filtered through a filter having a pore size of about 0.01 to 1 μm. The colored curable resin composition after mixing is preferably filtered through a filter with a pore size of about 0.01 to 10 μm.

[0173] <Color filter> Methods for producing a colored pattern of a color filter from the colored curable resin composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the colored curable resin composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.

[0174] The film thickness of the color filter (cured film) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, still more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, and preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0175] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass; a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate; silicon; or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS may be used.

[0176] Formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored curable resin composition is applied to a substrate, and then heated and dried (prebaked) and / or dried under reduced pressure to remove volatile components such as solvents and dry the composition, thereby obtaining a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. The temperature for heat drying is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably carried out under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C. The thickness of the composition layer is not particularly limited and may be appropriately selected depending on the desired thickness of the color filter.

[0177] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 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. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.

[0178] A colored pattern is formed on the substrate by bringing the exposed composition layer into contact with a developer and developing it. The unexposed portions of the composition layer are dissolved and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may also contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, or the like. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0179] Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-bake time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0180] The colored patterns and colored coating films thus obtained are useful as color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. [Example]

[0181] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples, % and parts representing the content or amount used are by mass unless otherwise specified.

[0182] [Synthesis Example 1] According to Example 8 described in JP 2020-055956 A, a compound represented by formula (II-135) was obtained.

[0183] [ka]

[0184] [Synthesis Example 2] According to Example 2 described in JP 2019-163233 A, a compound represented by formula (III-3) was obtained.

[0185] [ka]

[0186] [Resin synthesis example 1] 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 2,6A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (mixing ratio 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a mixed solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the flask was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (Resin (B-1)) solution with a Brookfield viscosity (23°C) of 125 mPa·s and a solids content of 35.1%. The resulting copolymer had a weight-average molecular weight Mw of 9200, a polydispersity of 2.08, and an acid value of the solids of 77 mg-KOH / g. Resin (B-1) has the following structural units.

[0187] [ka]

[0188] 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°C Solvent: THF Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standard material ;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.

[0189] [Examples 1 to 24, Comparative Example 1] [Preparation of Colored Curable Resin Composition] The components were mixed to obtain the compositions shown in Tables 16 and 17, thereby obtaining colored curable resin compositions. In Tables 16 and 17, each component represents the following compound. Colorant (A-1): Compound represented by formula (II-135) Colorant (A-2): Compound represented by formula (III-3) Resin (B-1): Resin (B-1) (solid content conversion) Polymerizable compound (C-1): pentaerythritol tetraacrylate (average ethylenically unsaturated group equivalent weight: 88.1; A-TMMT; manufactured by Shin-Nakamura Chemical Co., Ltd.) Polymerizable compound (C-2): pentaerythritol triacrylate and pentaerythritol tetraacrylate (average ethylenically unsaturated group equivalent weight: 94.6; A-TMM-3LM-N; trifunctional: approximately 57 mol%, tetrafunctional: approximately 43 mol%; manufactured by Shin-Nakamura Chemical Co., Ltd.) Polymerizable compound (C-3): glycerin triacrylate (average ethylenically unsaturated group equivalent weight: 84.7; Aronix (registered trademark) M-930; manufactured by Toagosei Co., Ltd.) Polymerizable compound (C-4): dipentaerythritol hexaacrylate (average ethylenically unsaturated group equivalent weight: 96.4; KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (PBG-327; oxime compound; Changzhou Strong Electronic New Materials Co., Ltd.) Polymerization initiator (D-2): 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyloxime (DFI-091; oxime compound; manufactured by Daito Chemiks Co., Ltd.) Polymerization initiator (D-3): N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine (N-1919; oxime compound; manufactured by ADEKA Corporation) Solvent (E-1): 4-hydroxy-4-methyl-2-pentanone Solvent (E-2): Propylene glycol monomethyl ether acetate Leveling agent (F-1): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0190] [Preparation of colored coating film] A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the film thickness after post-baking would be 2.0 μm, and then pre-baked at 100° C. for 3 minutes to form a colored composition layer. After cooling, the colored composition layer was exposed to 100 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 The colored composition layer was irradiated with light at an exposure amount (365 nm standard) of 1000 ppm, and then post-baked in an oven at 230° C. for 30 minutes to obtain a colored coating film.

[0191] [Contrast rating] 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.) with a blank value of 30,000. The results are shown in Tables 16 and 17.

[0192] [Table 16]

[0193] [Table 17]

[0194] According to the above, when a predetermined amount of squarylium dye and a predetermined polymerizable compound are used as colorants, contrast is improved. In addition, when the amount of polymerizable compound is increased and the amount of polymerization initiator is decreased, contrast is further improved.

Claims

1. The composition comprises a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), the colorant (A) comprises a squarylium dye, the polymerizable compound (C) has an average ethylenically unsaturated group equivalent number represented by formula (1) of less than 96.0, The squarylium dye contains at least one compound selected from the group consisting of a compound represented by formula (I) and a compound represented by formula (III), The colored curable resin composition, wherein the content of the squarylium dye is 3 to 140 parts by mass per 100 parts by mass of the polymerization initiator (D). <Average Ethylenically Unsaturated Group Equivalent Number> Average ethylenically unsaturated group equivalent number of polymerizable compound (C)=ΣK i m i …(1) [In formula (1), K i represents the value expressed as (molecular weight / number of ethylenically unsaturated bonds) of component i among all polymerizable compounds (C) contained in the colored curable resin composition. m i : represents the mole fraction of component i.] 【Chemistry 1】 [In formula (I), R 1 to R 8 each independently represent a hydrogen atom, a halogen atom, a hydroxy group, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent. R 9 and R 10 each independently represent a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and a methylene group contained in the aliphatic hydrocarbon group may be replaced with —O—. R 11 and R 12 each independently represent a hydrocarbon group having 6 to 20 carbon atoms and an aromatic hydrocarbon ring, the hydrocarbon group may have a substituent, and a methylene group contained in the hydrocarbon group may be replaced with —O—. R 13 represents a hydrogen atom or a saturated hydrocarbon group having 1 to 8 carbon atoms.] 【Chemistry 2】 [In formula (III), R 31 to R 38 each independently represent a hydrogen atom, a hydroxy group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms. R 39 to R 42 each independently represent a hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, at least one of R 39 to R 42 is an aliphatic hydrocarbon group of 1 to 20 carbon atoms which has a carboxy group as a substituent, and at least one of R 39 to R 42 is an aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent, and a methylene group contained in the aliphatic hydrocarbon group may be replaced with —O—.]

2. 2. The colored curable resin composition according to claim 1, wherein the average ethylenically unsaturated group equivalent number is 83.0 or more.

3. The colored curable resin composition according to claim 1 or 2, wherein the polymerizable compound (C) includes a polymerizable compound having 3 to 5 ethylenically unsaturated bonds.

4. The colored curable resin composition according to any one of claims 1 to 3, wherein the polymerizable compound (C) comprises at least one selected from pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and glycerin tri(meth)acrylate.

5. The colored curable resin composition according to any one of claims 1 to 4, wherein the polymerization initiator (D) comprises an O-acyloxime compound.

6. A color filter formed from the colored curable resin composition according to any one of claims 1 to 5.

7. A display device comprising the color filter according to claim 6.

8. A solid-state imaging device comprising the color filter according to claim 6.

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