Coloring curable resin composition, color filter, display device, and solid-state imaging device

Abstract

An object of the present invention is to provide a coloring curable resin composition capable of producing a color filter having improved color separation properties from green light.SOLUTION: The colored curable resin composition of the present invention contains a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant contains a xanthene dye (a1) having a maximum absorption wavelength of 510 nm or more and not more than 535 nm, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and not more than 570 nm, and a blue pigment (a3).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a colored curable resin composition, a color filter formed from the colored curable resin composition, and a display device and a solid-state imaging device that include the color filter. [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 usually composed of color pixels (specifically, red, green, and blue filters), and each color filter is formed from a colored curable resin composition. For example, Patent Document 1 describes a composition for forming a blue color filter that uses a colorant containing, relative to the total weight of the colorant, 60 to 85 wt % of a blue pigment (A-1), 5 to 20 wt % of a blue pigment (A-2) other than the blue pigment (A-1), 5 to 20 wt % of a violet pigment (B), and 0.5 to 5 wt % of a violet dye (C). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2023-124822 Summary of the Invention [Problem to be solved by the invention]

[0004] However, further improvement in color separation is required for color filters formed from the composition described in Patent Document 1. For example, in a blue color filter, it is required to suppress leakage of green light. Therefore, an object of the present invention is to provide a colored curable resin composition that can be used to prepare a color filter with improved color separation from green light. [Means for solving the problem]

[0005] The gist of the present invention is as follows. [1] A composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator; The colored curable resin composition, wherein the colorant comprises a xanthene dye (a1) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3). [2] The colored curable resin composition according to [1], wherein the content ratio (a1 / a2) of the xanthene colorant (a1) to the xanthene colorant (a2) is 0.1 to 15 on a mass basis. [3] The colored curable resin composition according to [1] or [2], wherein the total content of the xanthene colorant (a1) and the xanthene colorant (a2) is 8 parts by mass or more per 100 parts by mass of the blue pigment (a3). [4] The colored curable resin composition according to any one of [1] to [3], wherein the content of the colorant is 35 mass % or more relative to the total amount of solids in the colored curable resin composition. [5] The colored curable resin composition according to any one of [1] to [4], wherein the content ratio (a1 / a2) of the xanthene colorant (a1) to the xanthene colorant (a2) is 10 or less by mass. [6] The colored curable resin composition according to any one of [1] to [5], wherein the content of the xanthene colorant (a1) is 7 to 15 mass % relative to 100 mass % of the colorant. [7] The colored curable resin composition according to any one of [1] to [6], wherein the content ratio (a1 / a2) of the xanthene colorant (a1) to the xanthene colorant (a2) is 1.0 to 10 by mass. [8] The colored curable resin composition according to any one of [1] to [7], wherein the xanthene colorant (a2) contains a compound represented by formula (1): [ka] [In formula (1), R 1 ~R 4are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or *-R 12 -Si(R 13 ) 3 (* indicates the bonding position to the nitrogen atom), and R 1 and R 2 may be taken together to form a ring containing the nitrogen atom, R 3 and R 4 may be taken together to form a ring containing a nitrogen atom, provided that R 1 ~R 4 The total number of aromatic hydrocarbon rings contained in is 4 or more. R 5 -OH, -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 , -SO3R 8 or -SO2NR 9 R 10 Represents. R 6 ~R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 8 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a halogen atom. R 9 and R 10 each independently represents a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 9 and R 10 may be taken together to form a ring containing the nitrogen atom. R 12 represents an alkanediyl group having 1 to 10 carbon atoms, and -CH2- contained in the alkanediyl group is not selected from -O-, -CO-, -NR 8 It may be substituted by -, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO-. R 13represents a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and a plurality of R 13 may be the same or different. Z + represents any cation. X represents a halogen atom. a represents 0 or 1. m represents an integer of 0 to 5, and when m is 2 or more, a plurality of R 5 may be the same or different.] [9] A color filter formed from the colored curable resin composition according to any one of [1] to [8].

[10] A display device comprising the color filter according to [9].

[11] A solid-state imaging device comprising the color filter according to [9]. [Effects of the Invention]

[0006] The colored curable resin composition of the present invention makes it possible to produce a color filter having improved color separation from green light. DETAILED DESCRIPTION OF THE INVENTION

[0007] [Colored curable resin composition] The present invention encompasses a colored curable resin composition comprising a colorant (hereinafter sometimes referred to as colorant (A)), a resin (hereinafter sometimes referred to as resin (B)), a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), wherein the colorant (A) comprises a xanthene dye (a1) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3). Use of such a colored curable resin composition allows for the production of a color filter with improved color separation from green light, preferably a color filter with improved color separation from both green light and red light, and also allows the production of a color filter that can be used to fabricate a high-sensitivity solid-state imaging device. The colored curable resin composition of the present invention preferably further contains 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 each component can be used alone or in combination, unless otherwise specified.

[0008] <Colorant (A)> The xanthene dye (a1) and the xanthene dye (a2) are dyes containing a compound having a xanthene skeleton in the molecule, and each has a specific maximum absorption wavelength.

[0009] The maximum absorption wavelength of the xanthene dye (a1) is 510 to 535 nm, preferably 515 to 530 nm. The maximum absorption wavelength of the xanthene dye (a2) is longer than 535 nm and not more than 570 nm, preferably 536 to 560 nm, and more preferably 536 to 545 nm. The maximum absorption wavelength of the xanthene dye can be measured by the method described in the Examples below.

[0010] Preferably, one or both of the xanthene dye (a1) and the xanthene dye (a2) correspond to the compound represented by formula (1). It is preferable to select and combine the xanthene dye (a1) and the xanthene dye (a2) from the compounds represented by formula (1) according to the maximum absorption wavelength. The compound represented by formula (1) may be a tautomer thereof.

[0011] [ka] [In formula (1), R 1 ~R 4 are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or *-R 12 -Si(R13 ) 3 (* indicates the bonding position to the nitrogen atom), and R 1 and R 2 may be taken together to form a ring containing the nitrogen atom, R 3 and R 4 may be taken together to form a ring containing the nitrogen atom. R 5 -OH, -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 , -SO3R 8 or -SO2NR 9 R 10 Represents. R 6 ~R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 8 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a halogen atom. R 9 and R 10 each independently represents a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 9 and R 10 may be taken together to form a ring containing the nitrogen atom. R 12 represents an alkanediyl group having 1 to 10 carbon atoms, and -CH2- contained in the alkanediyl group is not selected from -O-, -CO-, -NR 8 It may be substituted by -, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO-. R 13 represents a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and multiple R 13 may be the same or different. Z + represents any cation. X represents a halogen atom. a represents 0 or 1. m represents an integer of 0 to 5, and when m is 2 or more, a plurality of R 5 may be the same or different.]

[0012] R 1 ~R 4 , and R 8 ~R 10 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be either linear or cyclic, and examples thereof include linear or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, icosyl, isopropyl, isobutyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups.

[0013] R 1 ~R 4 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, still more preferably an alkyl group having 1 to 5 carbon atoms, and particularly preferably an alkyl group having 2 to 4 carbon atoms. R 8 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. R 9 ~R 10 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 4 to 10 carbon atoms.

[0014] R 1 ~R 4The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have a substituent, and examples of the substituent include aryl groups such as phenyl, tolyl, xylyl, and mesityl; halogen atoms such as fluorine, chlorine, bromine, and iodine; hydroxy groups; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; carboxy groups; alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and butoxycarbonyl; amino groups; and alkyl-substituted amino groups such as N-methylamino, N-ethylamino, and N,N-dimethylamino. Among these, halogen atoms, hydroxy groups, and carboxy groups are preferred, and carboxy groups are more preferred.

[0015] R 8 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be substituted with a halogen atom, and examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0016] R 9 and R 10 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have a substituent, and the substituent may be R 1 ~R 4 Examples of the substituent include the same groups as those that may be contained in the saturated hydrocarbon group having 1 to 20 carbon atoms and represented by the following formula: Among these, a halogen atom and a hydroxy group are preferred.

[0017] R 1 ~R 4 Examples of the aromatic hydrocarbon group having 6 to 30 carbon atoms represented by the formula (I) include a phenyl group; alkylphenyl groups such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group; arylphenyl groups such as a biphenyl group and a diphenylphenyl group; and a naphthyl group. The alkyl group constituting the alkylphenyl group is R 1 ~R 4Among these, alkyl groups having 1 to 10 carbon atoms are preferred, more preferably alkyl groups having 1 to 4 carbon atoms, and even more preferably methyl groups. The alkylphenyl group is preferably a group having an alkyl group at at least one of the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group, and more preferably a group having alkyl groups at the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group. In particular, the xanthene dye (a1) is preferably a group having an alkyl group at at least one of the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group, and even more preferably a group having an alkyl group at at least one of the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group. 1 ~R 4 Preferably, at least one of R is an alkylphenyl group. 1 ~R 4 More preferably, the compound contains a compound in which at least two of R are alkylphenyl groups. 1 and R 4 More preferably, the compound includes a compound in which is an alkylphenyl group. Examples of the aryl group constituting the arylphenyl group include a phenyl group; an alkylphenyl group such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group; and among these, an aryl group having 6 to 10 carbon atoms is preferred, and a phenyl group is more preferred. The arylphenyl group is preferably a group having an aryl group at at least one of two bonding positions that are ortho-positions relative to the N bonded to the phenyl group, and more preferably a group having an aryl group at two bonding positions that are ortho-positions relative to the N bonded to the phenyl group. In particular, the xanthene dye (a2) is preferably a group having an aryl group at at least one of two bonding positions that are ortho-positions relative to the N bonded to the phenyl group. 1 ~R 4 Preferably, at least one of R is an arylphenyl group. 1 ~R 4 More preferably, the compound includes a compound in which at least two of R are arylphenyl groups. 1 and R 4 More preferably, the compound includes a compound in which is an arylphenyl group.

[0018] In particular, R 1 ~R 4Examples of the aromatic hydrocarbon group having 6 to 30 carbon atoms represented by the formula: It is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, More preferably, the alkylphenyl group has an alkyl group at at least one of the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group, or the arylphenyl group has an aryl group at at least one of the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group, More preferably, the group is an alkylphenyl group having alkyl groups at two bonding positions that are ortho to the N bonded to the phenyl group, or an arylphenyl group having aryl groups at two bonding positions that are ortho to the N bonded to the phenyl group.

[0019] R 1 ~R 4 The aromatic hydrocarbon group having 6 to 30 carbon atoms represented by the formula (I) may have a substituent, and examples of the substituent include a halogen atom, —OH, —OR 8 , -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2R 8 , -SR 8 , -SO2R 8 , -SO3R 8 , -SO2NR 9 R 10 Among these, -SO3 - , -SO3H, -SO3 - Z + , -SO2NR 9 R 10 is preferred, -SO3 - , -SO3 - Z + , -SO2NR 9 R 10 is more preferred, -SO3 - is more preferable. In this case, -SO3 - Z + As for -SO3 - N + (R 11) 4 is preferred. When the aromatic hydrocarbon group having 6 to 30 carbon atoms has a substituent, the substituent is preferably directly bonded to the aromatic hydrocarbon ring.

[0020] Z + is the ammonium cation, Na + or K + is preferred, and more preferably, an ammonium cation. In this specification, the ammonium cation is defined as NH4 + The term "ammonium cation" is defined to include, but is not limited to, organic ammonium cations such as primary ammonium cations, secondary ammonium cations, tertiary ammonium cations, and quaternary ammonium cations, among which quaternary ammonium cations are preferred. Examples of the ammonium cation include those having a -N partial structure. + (R 11 )3 and polymers with N + (R 11 )4. Multiple R 11 may be the same or different.

[0021] R 11 represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. R 11 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably an alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 15 carbon atoms. R 11 Examples of the aralkyl group having 7 to 10 carbon atoms represented by the formula (I) include a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, and a naphthylmethyl group. N + (R 11 )4 is the four R 11 Among the four R groups, at least two are preferably saturated hydrocarbon groups having 5 to 20 carbon atoms (particularly alkyl groups having 5 to 20 carbon atoms). 11 The total number of carbon atoms is preferably 20 to 80, and more preferably 20 to 60.

[0022] -OR 8 Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.

[0023] -CO2R 8 Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

[0024] -SR 8 Examples of the sulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.

[0025] -SO2R 8 Examples of the sulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.

[0026] -SO3R 8 Examples of the sulfonyl group include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

[0027] -SO2NR 9 R 10 As for sulfamoyl group; N-Methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-(1,1-dimethylpropyl)sulfamoyl group, N-(1,2-dimethylpropyl)sulfamoyl group, N-(2,2-dimethylpropyl)sulfamoyl group, N-(1-methylbutyl)sulfamoyl group, N-(2-methylbutyl)sulfamoyl group N-1-substituted sulfamoyl groups such as a sulfamoyl group, an N-(3-methylbutyl)sulfamoyl group, an N-cyclopentylsulfamoyl group, an N-hexylsulfamoyl group, an N-(1,3-dimethylbutyl)sulfamoyl group, an N-(3,3-dimethylbutyl)sulfamoyl group, an N-heptylsulfamoyl group, an N-(1-methylhexyl)sulfamoyl group, an N-(1,4-dimethylpentyl)sulfamoyl group, an N-octylsulfamoyl group, an N-(2-ethylhexyl)sulfamoyl group, an N-(1,5-dimethyl)hexylsulfamoyl group, and an N-(1,1,2,2-tetramethylbutyl)sulfamoyl group; N,N-disubstituted sulfamoyl groups such as N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, and N,N-heptylmethylsulfamoyl group; and the like.

[0028] R 12Examples of the alkanediyl group having 1 to 10 carbon atoms represented by the formula (I) include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an isopropylene group, an isobutylene group, a 2-methyltrimethylene group, an isopentylene group, an isohexylene group, an isooctylene group, a 2-ethylhexylene group, etc. Among these, an alkanediyl group having 1 to 6 carbon atoms is preferred, and an alkanediyl group having 1 to 4 carbon atoms is more preferred.

[0029] R 12 The -CH2- contained in the alkanediyl group represented by the formula 8 It may be substituted by -, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO-.

[0030] R 13 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula include a methyl group, an ethyl group, a propyl group, and a butyl group. R 13 Examples of the alkoxy group having 1 to 4 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, a propoxy group, and a tert-butoxy group. R 13 is preferably a methyl group, an ethyl group, a methoxy group, or an ethoxy group, and more preferably a methoxy group or an ethoxy group.

[0031] R 1 and R 2 , R 3 and R 4 , R 9 and R 10 Examples of the ring containing a nitrogen atom formed by combining with are as follows: In the following structures, * represents a bond.

[0032] [ka]

[0033] R 1 ~R 4are preferably each independently a hydrogen atom, a saturated hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 30 carbon atoms which may have a substituent, more preferably each independently a hydrogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 30 carbon atoms which may have a substituent, and even more preferably each independently a hydrogen atom, an alkyl group of 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent.

[0034] In particular, in the xanthene dye (a1), R 1 and R 4 each independently represents an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, and R 2 and R 3 each independently represents a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 1 and R 4 each independently represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and R 2 and R 3 more preferably, each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent, and R 1 and R 4 each independently represents an alkylphenyl group having 7 to 20 carbon atoms which may have a substituent, and R 2 and R 3 and more preferably each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent. In addition, in the xanthene dye (a2), R 1 and R 4 each independently represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent; R 2 and R 3each independently represents a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 1 and R 4 each independently represents an alkyl group having 1 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, R 2 and R 3 more preferably, each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent, and R 1 and R 4 each independently represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an alkylphenyl group having 7 to 20 carbon atoms which may have a substituent, or an arylphenyl group having 12 to 20 carbon atoms which may have a substituent, R 2 and R 3 and more preferably each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent.

[0035] R 9 and R 10 are each independently preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a branched alkyl group having 3 to 10 carbon atoms, and even more preferably a hydrogen atom or a 2-ethylhexyl group. 9 is a hydrogen atom, and R 10 is preferably an alkyl group having 1 to 10 carbon atoms, and R 9 is a hydrogen atom, and R 10 is more preferably a branched alkyl group having 3 to 10 carbon atoms, and R 9 is a hydrogen atom, and R 10 is more preferably a 2-ethylhexyl group.

[0036] R 6 ~R 7 Examples of the alkyl group having 1 to 6 carbon atoms represented by the formula include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.

[0037] R6 ~R 7 are each independently preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom.

[0038] R 5 is preferably -CO2H, -CO2 - Z + , -CO2R 8 , -SO3 - , -SO3 - Z + , -SO3H, -SO2NR 9 R 10 and more preferably -SO3 - , -SO3 - Z + , -SO3H, -SO2NR 9 R 10 and more preferably -SO3 - , -SO3 - Z + is.

[0039] m is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0040] R 5 The bonding positions of are not particularly limited, but are preferably bonded to at least one of the two bonding positions that are ortho-positions relative to the xanthene skeleton, and more preferably bonded to one of the two bonding positions that are ortho-positions relative to the xanthene skeleton. Furthermore, when m is 2 or more, are preferably bonded to at least one of the two bonding positions that are ortho-positions relative to the xanthene skeleton and a bonding position that is para-position, and more preferably bonded to one of the two bonding positions that are ortho-positions relative to the xanthene skeleton and a bonding position that is para-position.

[0041] Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0042] In formula (1), -SO3 in the form of ions -The number of is preferably 0 or 1, and more preferably 1.

[0043] a represents 0 or 1, and is preferably 0.

[0044] The compound represented by formula (1) is preferably electrically neutral. That is, the compound represented by formula (1) is preferably in the form of an ion, -SO3 - When the compound represented by formula (1) has one -SO3, it is preferable that a is 0. - When there is no a, it is preferred that a is 1.

[0045] The compound represented by formula (1) is -SO3 - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 It is preferable that the compound has one or more groups selected from the group consisting of:

[0046] The xanthene dye (a1) and the xanthene dye (a2) are preferably compounds represented by formula (2) or (3) having the above-mentioned specific maximum absorption wavelength. The compound represented by formula (2) may be a tautomer thereof, and the compound represented by formula (3) may be a tautomer thereof.

[0047] [ka]

[0048] [In formula (2), R 21 and R 22 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent. R 23 and R 24 are each independently an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, -SO3 -, -SO3H, -SO3 - Z + , or -SO2NR 29 R 30 Represents. p and q each independently represent an integer of 0 to 5, and when p is 2 or more, a plurality of R 23 may be the same or different, and when q is 2 or more, multiple R 24 may be the same or different. R 25 is -SO3 - , -SO3H, -SO3 - Z + , or -SO2NR 29 R 30 Represents. R 29 and R 30 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. a, m, X, and Z + is the same as above.]

[0049] [ka]

[0050] [In formula (3), R 31 and R 34 each independently represents an alkyl group having 1 to 10 carbon atoms which may have a substituent. R 32 and R 33 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent. R 35 is -SO3 - , -SO3H, -SO3 - Z + , or -SO2NR 29 R 30 Represents. R 29 and R 30 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. a, m, X, and Z +is the same as above.]

[0051] In formula (2) and formula (3), a, m, X, and Z + a, m, X, and Z in formula (1), including preferred embodiments thereof. + is the same as:

[0052] R 21 ~R 22 , R 29 ~R 30 , and R 31 ~R 34 Specific examples of the alkyl group having 1 to 10 carbon atoms represented by the formula (I) include linear or branched alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an isopropyl group, an isobutyl group, a tert-butyl group, an isopentyl group, a neopentyl group, and a 2-ethylhexyl group.

[0053] R 21 ~R 22 and R 31 ~R 34 The alkyl group having 1 to 10 carbon atoms represented by the formula (I) may have a substituent, and the substituent is, for example, R 1 ~R 4 Examples of the substituent include the same groups as those that may be contained in the saturated hydrocarbon group having 1 to 20 carbon atoms and represented by the following formula: Among these, a halogen atom, a hydroxy group, and a carboxy group are preferred, and a carboxy group is more preferred.

[0054] R 21 and R 22 are each independently preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a carboxy group, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a carboxy group, and even more preferably a hydrogen atom.

[0055] R 29 and R 30are each independently preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a branched alkyl group having 3 to 10 carbon atoms, and even more preferably a hydrogen atom or a 2-ethylhexyl group. 29 is a hydrogen atom, and R 30 is preferably an alkyl group having 1 to 10 carbon atoms, and R 29 is a hydrogen atom, and R 30 is more preferably a branched alkyl group having 3 to 10 carbon atoms, and R 29 is a hydrogen atom, and R 30 is more preferably a 2-ethylhexyl group.

[0056] R 31 and R 34 are each independently preferably an alkyl group having 1 to 8 carbon atoms which may have a substituent, more preferably an alkyl group having 1 to 5 carbon atoms which may have a substituent, and even more preferably an alkyl group having 2 to 4 carbon atoms which may have a substituent.

[0057] R 32 and R 33 are each independently preferably a hydrogen atom or an alkyl group of 1 to 8 carbon atoms which may have a substituent, more preferably a hydrogen atom or an alkyl group of 1 to 5 carbon atoms which may have a substituent, still more preferably a hydrogen atom or an alkyl group of 2 to 4 carbon atoms which may have a substituent, and particularly preferably an alkyl group of 2 to 4 carbon atoms which may have a substituent.

[0058] R 23 and R 24 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (I) include a linear or branched alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Among these, an alkyl group having 1 to 2 carbon atoms is preferred, and a methyl group is more preferred.

[0059] R 23 and R 24Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by the formula include a phenyl group; an alkylphenyl group such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group; and among these, a phenyl group is preferred.

[0060] R 23 and R 24 are each independently an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or -SO3 - is preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and more preferably a methyl group or a phenyl group. In particular, in the xanthene dye (a1), R 23 and R 24 are each independently preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group. In addition, in the xanthene dye (a2), R 23 and R 24 are each independently an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or -SO3 - is preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and particularly preferably a phenyl group.

[0061] R 23 and R 24 is preferably bonded to at least one of the two bonding positions that are ortho-positions relative to N, and more preferably bonded to one of the two bonding positions that are ortho-positions relative to N.

[0062] p and q are each independently preferably an integer of 0 to 3, more preferably an integer of 1 to 3, even more preferably an integer of 1 to 2, and particularly preferably 2.

[0063] R 25 is -SO3 -It is particularly preferred that:

[0064] R 35 is -SO3 - or -SO3 - Z + It is preferable that:

[0065] In formulas (2) and (3), -SO3 in the form of an ion - The number of is preferably 0 or 1, and more preferably 1.

[0066] The compounds of formulas (2) and (3) are preferably electrically neutral, i.e., in the ionic form -SO3 - When there is one, a is preferably 0, and the ionic form -SO3 - When there is no a, it is preferred that a is 1.

[0067] The compounds represented by formulas (2) and (3) are -SO3 - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 It is preferable that the compound has one or more groups selected from the group consisting of:

[0068] In particular, the xanthene dye (a1) is preferably a compound represented by formula (1), and more preferably a compound represented by formula (2). - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 and R 23 and R 24 are each independently an alkyl group having 1 to 4 carbon atoms, -SO3 - , -SO3H, -SO3 - Z + , or -SO2NR 29 R30 It is also preferred that the compound is

[0069] The xanthene dye (a2) is preferably a compound represented by formula (1), and more preferably a compound represented by formula (2) or (3). The xanthene dye (a2) is a compound represented by formula (1), and is —SO3 - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 The compound (i) is preferably a compound having two or more (particularly 2 to 4) groups selected from the group consisting of: - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 It is more preferable that the compound has two or more (particularly, two to four) groups selected from the group consisting of: The xanthene dye (a2) is a compound represented by formula (1), 1 ~R 4 It is also preferable that the compound (hereinafter referred to as compound (ii)) has a total number of aromatic hydrocarbon rings (preferably benzene rings) of R 1 ~R 4 The total number of aromatic hydrocarbon rings contained in the compound (ii) is more preferably 4 to 6. The compound (ii) is a compound represented by formula (2), in which R is an aromatic hydrocarbon group having 6 to 10 carbon atoms. 23 and R is an aromatic hydrocarbon group having 6 to 10 carbon atoms. 24 It is more preferable that the compound has at least one (particularly two) of the above. That is, the xanthene dye (a2) is preferably the compound (i) or the compound (ii), and more preferably contains at least the compound (ii).

[0070] Examples of the compound represented by formula (1) include compounds represented by formulas (1-1) to (1-56): In the following formulas, Ra represents a 2-ethylhexyl group.

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] Specific examples of the compound represented by formula (1) include salt-forming compounds of any of the compounds represented by formulas (a) to (d) below with a copolymer of a monomer group including methyl methacrylate, 2-ethylhexyl methacrylate, and dimethylaminoethyl methacrylate methyl chloride salt, the copolymer having a glass transition temperature of 30 to 60°C and an ammonium salt value of 30 to 40 mgKOH / g converted to solids. The glass transition temperature can be calculated using Fox's equation, and the ammonium salt value can be calculated by titrating with a 0.1 N silver nitrate aqueous solution using a 5% potassium chromate aqueous solution as an indicator, and then converting it into an equivalent amount of potassium hydroxide.

[0079] [ka]

[0080] The colored curable resin composition of the present invention may contain one or more types of xanthene colorants (a1), and may contain one or more types of xanthene colorants (a2).

[0081] The blue pigment (a3) ​​contained in the colorant (A) can be a known blue pigment, and examples thereof include pigments having a blue hue that are classified as pigments in the Color Index (published by The Society of Dyers and Colourists). The colored curable resin composition of the present invention may contain one or more types of blue pigment (a3).

[0082] Specific examples of the blue pigment (a3) ​​include CI Pigment Blue 15, 15:3, 15:4, 15:6, 16, 60, and 80. Of these, phthalocyanine blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, and 16 are preferred, copper phthalocyanine blue pigments such as CI Pigment Blue 15, 15:3, 15:4, and 15:6 are more preferred, CI Pigment Blue 15:4 and / or 15:6 are even more preferred, and it is particularly preferred that the pigment contains at least CI Pigment Blue 15:6. In 100% by mass of the blue pigment (a3), the content of CI Pigment Blue 15:6 is preferably 30% by mass or more, more preferably 50% by mass or more, even more preferably 70% by mass or more, particularly preferably 80% by mass or more or 85% by mass or more, and may be 100% by mass.

[0083] The content of the xanthene dye (a1) is preferably 1 to 40% by mass, more preferably 5 to 20% by mass, and even more preferably 7 to 15% by mass, relative to the total amount of the colorant (A). By adjusting the content of the xanthene dye (a1) within the above range, red light leakage in the resulting color filter can be further suppressed. Furthermore, from the viewpoint of further suppressing red light leakage in the resulting color filter, it is also preferable that the xanthene dye (a1) represented by formula (2) is 7% by mass or more.

[0084] The content of the xanthene colorant (a2) is preferably 0.1 to 40 mass %, more preferably 0.5 to 30 mass %, even more preferably 0.8 to 25 mass %, and may be 0.8 to 15 mass %, relative to the total amount of the colorant (A).

[0085] The content ratio (a1 / a2) of the xanthene dye (a1) to the xanthene dye (a2) is preferably 0.05 to 20 by mass, more preferably 0.1 to 15, even more preferably 1.0 to 10, and particularly preferably 1.0 to 7. By adjusting the mass ratio (a1 / a2) within the above range, leakage of green light from the resulting color filter can be further suppressed. Furthermore, by adjusting the mass ratio (a1 / a2) to 1.0 to 10 (preferably 1.0 to 7), a color filter that enables the production of a solid-state imaging device with higher sensitivity can be formed.

[0086] The content of the blue pigment (a3) ​​is preferably 30 to 98 mass %, more preferably 50 to 94 mass %, and even more preferably 60 to 90 mass %, based on the total amount of the colorant (A).

[0087] The total content of the xanthene colorant (a1) and the xanthene colorant (a2) is, for example, 3 to 60 parts by mass, preferably 8 to 50 parts by mass, more preferably 12 to 40 parts by mass, and even more preferably 20 to 40 parts by mass, relative to 100 parts by mass of the blue pigment (a3). By adjusting the total content to equal to or greater than the lower limit, leakage of green light from the resulting color filter is more easily suppressed. On the other hand, by adjusting the total content to equal to or less than the upper limit, leakage of red light from the resulting color filter is more easily suppressed.

[0088] The total content of the xanthene colorant (a1), the xanthene colorant (a2), and the blue pigment (a3) ​​is preferably 60% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, and may be 98% by mass or more or 100% by mass, based on the total amount of the colorant (A).

[0089] The colorant (A) may contain one or more colorants other than the xanthene colorant (a1), the xanthene colorant (a2), and the blue pigment (a3) ​​(hereinafter, sometimes referred to as other colorants (a4)).

[0090] The other colorant (a4) may be either a dye (hereinafter, sometimes referred to as dye (a4-1)) or a pigment (hereinafter, sometimes referred to as pigment (a4-2)).

[0091] The dye (a4-1) is not particularly limited, and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used based on their chemical structure include xanthene dyes other than the xanthene dye (a1) and the xanthene dye (a2), azo dyes, cyanine dyes, triarylmethane dyes, thiazole dyes, oxazine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, and isoindoline dyes.

[0092] Specific examples of the dye (a4-1) include CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, and 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 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, and 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, 57, 66, 73, 76, 80, 88, 91, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 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, 236, 237, 238, 240, 241, 242, 243, 245, 24 83, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 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, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72; 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, and 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 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, 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, and 53; Examples include CI Vat dyes such as CI Vat Green 1. These dyes (a4-1) may be used alone or in combination for each color.

[0093] Examples of the pigment (a4-2) include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0094] Specific examples of pigments (a4-2) classified as pigments include: Yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, 235, 236; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 272, 273, 291, 297; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67; Purple pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1, 7, 31, and 32; These pigments (a4-2) may be used alone or in combination for each color.

[0095] The xanthene colorant (a1), the xanthene colorant (a2), the blue pigment (a3), and the pigment (a4-2) may be optionally subjected to a rosin treatment, a surface treatment using a pigment derivative having an acidic or basic group introduced therein, a grafting treatment onto the pigment surface using a polymeric compound, a particle size reduction treatment using a sulfuric acid atomization method, a washing treatment using an organic solvent or water to remove impurities, or a treatment to remove ionic impurities using an ion exchange method. The particle size of these colorants is preferably substantially uniform. Furthermore, by adding a pigment dispersant and dispersing the colorants, they can be made into a colorant dispersion in which they are uniformly dispersed in the pigment dispersant solution. These colorants may be dispersed individually or in combination.

[0096] Examples of pigment dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of pigment dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie).

[0097] When a pigment dispersant is used, the amount used is preferably 5 to 200 parts by mass, more preferably 8 to 150 parts by mass, and even more preferably 10 to 100 parts by mass, relative to 100 parts by mass of the colorant. When the amount of the pigment dispersant used is within the above range, a colorant dispersion in a more uniformly dispersed state tends to be obtained when preparing a colorant dispersion containing two or more colorants.

[0098] The content of the colorant (A) is, for example, 10 to 75 mass%, preferably 20 to 65 mass%, more preferably 30 to 55 mass%, and even more preferably 35 to 55 mass%, of the total amount of solids. By adjusting the content of the colorant (A) to equal to or greater than the lower limit, it becomes easier to obtain a spectrum and color density suitable for a color filter. By adjusting the content of the colorant (A) to equal to or less than the upper limit, reliability and patterning ability can be improved. In particular, by using the colored curable resin composition of the present invention, a color filter having good color separation properties can be produced while suppressing the colorant concentration. In other words, it is preferable in that color separation properties can be achieved simultaneously with reliability such as chemical resistance and heat resistance, and patterning ability. In this specification, the term "total amount of solids" refers to the total amount of components excluding the solvent from the colored curable resin composition of the present invention. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0099] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added and a structural unit derived from (c), and which contains a structural unit derived from (a) to which (b) has not been added; Resin [K4']: a copolymer having a structural unit derived from (a) to which (b) has been added and a structural unit derived from (c), but not containing a structural unit derived from (a) to which (b) has not been added; Resin [K5]: a copolymer having structural units derived from (b) to which (a) has been added and structural units derived from (c) (which may contain, but preferably does not contain, structural units derived from (b) to which (a) has not been added); Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further adding a carboxylic acid anhydride, and a structural unit derived from the (c).

[0100] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.

[0101] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0102] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0103] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0104] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0105] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0106] [ka]

[0107] [In formula (BI) and formula (BII), R e and R f represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X e and X f is a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0108] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R e and R f Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0109] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X e and X fPreferred 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).

[0110] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formula (BI-1), (BI-3), (BII-5), (BI-7), (BI-9) or (BI-11) to (BI-15) are preferred, and compounds represented by formula (BI-1), (BI-7), (BI-9) or (BI-15) are more preferred.

[0111] [ka]

[0112] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formula (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) or (BII-11) to (BII-15) are preferred, and compounds represented by formula (BII-1), (BII-7), (BII-9) or (BII-15) are more preferred.

[0113] [ka]

[0114] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0115] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0116] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0117] As (b), (b1) is preferred in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b1-2) is more preferred in that it provides excellent storage stability to the colored curable resin composition.

[0118] Examples of (c) include unsaturated carboxylic acid esters such as (meth)acrylic acid ester monomers and unsaturated dicarboxylic acid esters; vinyl monomers such as vinyl monomers having an unsaturated aliphatic hydrocarbon ring or an aromatic ring; and maleimides. Examples of the (meth)acrylic acid ester monomer include (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and cyclopentyl (meth)acrylate; (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, such as allyl (meth)acrylate and propargyl (meth)acrylate; Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate (commonly known in the technical field as "dicyclopentanyl (meth)acrylate" and sometimes called "tricyclodecyl (meth)acrylate"), isobornyl (meth)acrylate, and adamantyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), and dicyclopentanyloxyethyl (meth)acrylate; (meth)acrylic acid esters having an aromatic ring, such as phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and phenoxybenzyl (meth)acrylate; Examples thereof include hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate. Examples of the unsaturated dicarboxylic acid ester include dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate.

[0119] Among these unsaturated carboxylic acid esters, C such as methyl methacrylate and 2-ethylhexyl acrylate 1-10 Alkyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ] (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl(meth)acrylate; Preferred are (meth)acrylic acid esters having an aromatic ring, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate.

[0120] Vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (also called 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxy ethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6- Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 ]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, and other bicyclounsaturated compounds. Examples of vinyl monomers having an aromatic ring include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene. Other vinyl monomers include nitrile group-containing monomers such as acrylonitrile and methacrylonitrile; Halogen atom-containing monomers such as vinyl chloride and vinylidene chloride; Examples include acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these vinyl monomers, styrene-based monomers such as styrene and vinyltoluene, and bicyclounsaturated compounds such as bicyclo[2.2.1]hept-2-ene (also called 2-norbornene) are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0121] Examples of maleimides include 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. Among these maleimides, maleimides having an alicyclic hydrocarbon group or an aromatic hydrocarbon group, such as N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide, are preferred in terms of copolymerization reactivity and heat resistance.

[0122] The structural unit obtained by adding (b) to a structural unit derived from (a) refers to a unit formed by adding (b) to a structural unit derived from (a) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (b). In this structural unit, (a) may be any of the above-mentioned examples, and (b) may also be any of the above-mentioned examples. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred.

[0123] The structural unit obtained by adding (a) to a structural unit derived from (b) refers to a unit formed by adding (a) to a structural unit derived from (b) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0124] A structural unit obtained by adding (a) to a structural unit derived from (b) and then further adding a carboxylic acid anhydride refers to a structural unit in which (a) is added to a structural unit derived from (b) constituting the main chain of the copolymer, resulting in the formation of a hydroxyl group, to which a carboxylic acid anhydride is attached through half-esterification. This structural unit has a pendant carboxy group derived from the carboxylic acid anhydride and a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. Examples of carboxylic acid anhydrides include saturated aliphatic polycarboxylic acid anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; and alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0125] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: It is also preferable that the structural unit derived from (c) is not substantially contained. The total of the structural units derived from (a) and the structural units derived from (b) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K1]. When the ratio of the structural units of the resin [K1] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

[0126] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0127] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, tert-butylperoxy-2-ethylhexanoate, etc.). Solvents that dissolve the respective monomers can be used, and examples of the solvents that will be described later as the solvent (E) for the colored curable resin composition of the present invention can include the solvents described below.

[0128] The resulting copolymer may be used as a solution after the reaction as is, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be used as is for preparing the colored curable resin composition of the present invention, thereby simplifying the production process for the colored curable resin composition of the present invention.

[0129] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 1 to 70 mol% Structural units derived from (b): 1 to 60 mol% Structural units derived from (c): 20 to 95 mol% It is preferred that Structural units derived from (a): 3 to 50 mol% Structural units derived from (b): 3 to 40 mol% Structural units derived from (c): 30 to 90 mol% It is more preferable that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 30 mol% Structural units derived from (c): 40 to 80 mol% It is even more preferable that: The total of the structural units derived from (a), the structural units derived from (b), and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K2]. When the ratio of the structural units of the resin [K2] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and the obtained color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

[0130] In the resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (b) is preferably a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond, and more preferably a monomer (b1-2) having an epoxidized alicyclic unsaturated hydrocarbon. (c) is preferably a (meth)acrylic acid ester having a cyclic unsaturated aliphatic hydrocarbon group, a (meth)acrylic acid ester having an aromatic ring, or a dicarbonyl imide derivative.

[0131] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0132] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that Structural units derived from (a): 35 to 45 mol% Structural units derived from (c): 55 to 65 mol% It is even more preferable that: It is also preferable that the polymer contains substantially no structural units derived from (b). The total of the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all structural units constituting the resin [K3].

[0133] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid, and (c) is preferably a (meth)acrylic acid ester having an aromatic ring. Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0134] In the resin [K4], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a) (without addition of (b)): 1 to 60 mol% Structural units in which (b) is added to structural units derived from (a): 1 to 50 mol% Structural units derived from (c): 30 to 90 mol% It is preferred that Structural units derived from (a) (without addition of (b)): 5 to 50 mol% Structural units in which (b) is added to structural units derived from (a): 5 to 40 mol% Structural units derived from (c): 35 to 80 mol% It is more preferable that Structural units derived from (a) (without addition of (b)): 10 to 40 mol% Structural units in which (b) is added to structural units derived from (a): 10 to 25 mol% Structural units derived from (c): 40 to 75 mol% It is even more preferable that: The total of the structural units derived from (a) (without the addition of (b)), the structural units derived from (a) with the addition of (b), and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4].

[0135] The structural unit derived from (a) (without the addition of (b)) is preferably a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit obtained by adding (b) to a structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, bicyclounsaturated compounds, and styrene-based monomers, more preferably two or more. When (c) has two types of structural units derived from (c), it is preferable that two types are selected from unsaturated carboxylic acid esters such as (meth)acrylic acid esters, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring, and that two or more types are selected from bicyclounsaturated compounds and vinyl monomers such as styrene-based monomers.

[0136] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0137] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.), a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0138] In the resin [K4'], the ratio of the structural units derived from each of these is as follows, among all the structural units constituting the resin [K4']: Structural units in which (b) is added to structural units derived from (a): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units obtained by adding (b) to structural units derived from (a): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units obtained by adding (b) to structural units derived from (a): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferable that: Furthermore, structural units derived from (a) to which (b) is not added are not substantially included. The total of the structural units obtained by adding (b) to the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4'].

[0139] The structural unit obtained by adding (b) to a structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more selected from these. Resin [K4'] may be produced by referring to the production method of resin [K4] described above, and the amount of (b) used is preferably 100 mol or more, more preferably 100 mol, per 100 mol of (a).

[0140] In resin [K5], the ratio of structural units derived from each of these is as follows among all structural units constituting resin [K5]: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units in which (a) is added to structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units obtained by adding (a) to structural units derived from (b): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units in which (a) is added to structural units derived from (b): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is more preferable that: The total of the structural units derived from (b) (without (a) added), the structural units derived from (b) with (a) added, and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K5].

[0141] The structural unit derived from (b) (without (a) added) is preferably a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized. The structural unit in which (a) has been added to a structural unit derived from (b) is preferably a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more selected from these.

[0142] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0143] Furthermore, under the same conditions as in the production method of resin [K4] or resin [K4'], resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 100 mol, more preferably 60 to 100 mol, per 100 mol of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0144] In the resin [K6], the ratio of structural units derived from each of these is as follows: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 5 to 70 mol% A structural unit obtained by adding (a) to a structural unit derived from (b) and then adding a carboxylic acid anhydride thereto: 10 to 80 mol% Structural units derived from (c): 10 to 60 mol% It is preferred that Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 10 to 50 mol% Structural units obtained by adding (a) to a structural unit derived from (b) and then adding a carboxylic acid anhydride thereto: 25 to 60 mol% Structural units derived from (c): 15 to 50 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units in which (a) is added to structural units derived from (b) (no carboxylic acid anhydride is added); 15 to 35 mol% Structural units obtained by adding (a) to a structural unit derived from (b) and then adding a carboxylic acid anhydride thereto: 35 to 55 mol% Structural units derived from (c): 20 to 40 mol% It is even more preferable that:

[0145] The total of the structural units derived from (b) (to which (a) is not added), the structural units in which (a) is added to the structural units derived from (b) (to which carboxylic acid anhydride is not added), the structural units in which (a) is added to the structural units derived from (b) and then a carboxylic acid anhydride is added, and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K6].

[0146] As the structural unit derived from (b) (without (a) added), a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred. As the structural unit in which (a) has been added to a structural unit derived from (b) (without carboxylic acid anhydride added), a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred. As the structural unit in which (a) has been added to a structural unit derived from (b) and a carboxylic acid anhydride has been further added, a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid has been added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched-chain aliphatic unsaturated hydrocarbon has been epoxidized is preferred, The structural unit derived from (c) is preferably one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and more preferably two or more types.

[0147] Resin [K6] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0148] Furthermore, under the same conditions as in the production of resin [K4], the cyclic ether derived from (b) contained in the copolymer of (b) and (c) is reacted with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0149] The hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic acid anhydride contained in (a) is reacted with the carboxylic acid anhydride. The amount of carboxylic acid anhydride used is preferably 0.05 to 1 mol, more preferably 0.10 to 0.8 mol, and even more preferably 0.13 to 0.7 mol, relative to 1 mol of (a) used (in other words, 1 mol of hydroxy groups generated by the use of (a)).

[0150] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / tricyclo[5.2.1.0 2,6 ]decene-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] Decyl acrylate / (meth)acrylic acid / phenoxybenzyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, and other resins [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; Resins such as a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and a resin in which glycidyl (meth)acrylate is added to some of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer [K4]; Resins such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / (meth)acrylic acid with glycidyl (meth)acrylate, and a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid with glycidyl (meth)acrylate [K4']; Resins such as resins obtained by reacting tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymers with (meth)acrylic acid, and resins obtained by reacting tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymers with (meth)acrylic acid [K5]; Examples of such resins include a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with tetrahydrophthalic anhydride, a resin obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate, tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with succinic anhydride, and a resin obtained by reacting a copolymer of methyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, tricyclodecyl (meth)acrylate and glycidyl (meth)acrylate with (meth)acrylic acid and then reacting the resulting resin with succinic anhydride [K6].

[0151] The resin (B) may be used singly or in combination of two or more. The resin (B) is preferably at least one selected from the group consisting of resin [K1], resin [K2], resin [K4], and resin [K6], and more preferably resin [K2] and / or resin [K6]. When two or more resins (B) are used in combination, a preferred combination includes, for example, a combination of resins [K2] and [K6]. The combined use of resins [K2] and [K6] provides a better balance between patterning ability and reliability. When resins [K2] and [K6] are combined, the amount of resin [K2] is, for example, 5 to 99.9% by mass, preferably 50 to 99.8% by mass, and more preferably 75 to 99.7% by mass, relative to 100% by mass of the total of resins [K2] and [K6].

[0152] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the colored pattern tends to be improved. The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0153] The acid value of the resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 50 to 150 mg-KOH / g, and even more preferably 80 to 135 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0154] The content of resin (B) is preferably 5 to 65 mass%, more preferably 12 to 55 mass%, and even more preferably 20 to 45 mass%, relative to the total amount of solids in the colored curable resin composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0155] <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.

[0156] Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tri(meth)acrylate ... pentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylates (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylates (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated pentaerythritol tri(meth)acrylate), alkoxylated dipentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylates (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol caprolactone-modified pentaerythritol poly(meth)acrylates (for example, caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylates (for example, caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), and the like. Among these, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol poly(meth)acrylate, and alkoxylated dipentaerythritol poly(meth)acrylate is preferred. In particular, from the viewpoint of improving developability during colored pattern formation, alkoxylated dipentaerythritol poly(meth)acrylate is preferred, ethoxylated dipentaerythritol poly(meth)acrylate such as ethoxylated dipentaerythritol penta(meth)acrylate and ethoxylated dipentaerythritol hexa(meth)acrylate is more preferred, and ethoxylated dipentaerythritol polyacrylate such as ethoxylated dipentaerythritol pentaacrylate and ethoxylated dipentaerythritol hexaacrylate is even more preferred.

[0157] The number of moles of alkoxy groups added in the alkoxylated dipentaerythritol poly(meth)acrylate is preferably 2 to 30, more preferably 5 to 20, and even more preferably 8 to 15. The number of moles of ethoxy groups added in the ethoxylated dipentaerythritol poly(meth)acrylate and ethoxylated dipentaerythritol polyacrylate is also preferably adjusted to fall within the above range.

[0158] The content of the polymerizable compound (C) is, for example, 5 to 65 mass%, preferably 6 to 50 mass%, and more preferably 8 to 30 mass%, relative to the total amount of solids in the colored curable resin composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during colored pattern formation and the chemical resistance of the color filter tend to be further improved.

[0159] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and known polymerization initiators can be used.

[0160] Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0161] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): Hereinafter, * represents a bond.

[0162] [ka]

[0163] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N- Examples thereof include acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one. Commercially available products such as Irgacure OXE01, OXE02, and OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, O-acyloxime compounds include N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine. At least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is preferred, and at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is more preferred. These O-acyloxime compounds tend to produce color filters with high brightness.

[0164] The alkylphenone compound is preferably a compound having a partial structure represented by formula (d2) or (d3), wherein the benzene ring in these partial structures may have a substituent.

[0165] [ka]

[0166] Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.

[0167] Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0168] 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.

[0169] 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.

[0170] 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).

[0171] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (particularly an amine compound) described below.

[0172] 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.

[0173] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and more preferably a polymerization initiator containing an O-acyloxime compound. The content of the O-acyloxime compound in 100% by mass of the polymerization initiator (D) is, for example, 30 to 100% by mass, preferably 50% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.

[0174] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 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.

[0175] <Polymerization initiator aid (D1)> The colored curable resin composition of the present invention may further contain a polymerization initiation aid (D1). The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0176] 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.

[0177] 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.

[0178] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0179] 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.

[0180] 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.

[0181] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples thereof 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.

[0182] 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.

[0183] 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.

[0184] 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.

[0185] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0186] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0187] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0188] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0189] Among the above solvents, from the viewpoints of coatability and drying property, preferred are organic solvents having a boiling point at 1 atm of 120° C. or higher and 180° C. or lower. The solvent is preferably at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferably at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate.

[0190] It is also preferable to use an ether solvent and an ether ester solvent in combination as the solvent (E). In this case, the ether solvent is C 2-3 Alkylene glycol mono C 1-4 Alkyl ethers are preferred, and propylene glycol mono C 1-4 Alkyl ethers are more preferred. As the ether ester solvent, C 2-3 Alkylene glycol mono C 1-4 Alkyl ether acetate is preferred, propylene glycol mono C 1-4 Alkyl ether acetates are more preferred. When an ether solvent and an ether ester solvent are used in combination, the content of the ether solvent is preferably 0.1 to 30 parts by mass, and more preferably 1 to 10 parts by mass, relative to 100 parts by mass of the total of the ether solvent and the ether ester solvent. When the content of the ether solvent is within the above range, the solubility and dispersibility of components other than the solvent contained in the colored curable resin composition are improved, and the flatness during application tends to be good.

[0191] 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. In other words, the solid content of 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 coating is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics and sensitivity tend to be good.

[0192] <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.

[0193] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0194] 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 (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemicals Research Institute, Ltd.).

[0195] 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).

[0196] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, and even more preferably 0.005 to 0.05 mass%, relative to the total amount of the colored curable resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0197] <Other ingredients> The colored curable resin composition may contain additives known in the technical field, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.

[0198] <Method for producing colored curable resin composition> The colored curable resin composition can be prepared, for example, by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and, if necessary, a solvent (E), a leveling agent (F), a polymerization initiator aid (D1), and other components. The colored curable resin composition after mixing may be filtered through a filter with a pore size of about 0.01 to 10 μm.

[0199] As described above, the colorant (A) may be used as a colorant dispersion in which the colorant is uniformly dispersed in a solution by adding a pigment dispersant and carrying out a dispersion treatment. The desired colored curable resin composition can be prepared by mixing the remaining components into such a colorant dispersion to give a predetermined concentration.

[0200] When the colorant (A) contains a dye, the dye may be dissolved in advance in a part or all of the solvent (E) to prepare a solution, which is then preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0201] [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.

[0202] The film thickness of the color filter (colored coating film or colored pattern) 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 1.0 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.

[0203] 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.

[0204] Formation of each color pixel (each color filter) 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. When heated and dried, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When dried under reduced pressure, it is preferably carried out under a pressure of 50 to 150 Pa and at a temperature of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the desired color filter.

[0205] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 250 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, or 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] In particular, the colored pattern and colored coating film are useful as blue pixels in a color filter (blue color filter).

[0210] When the thickness of the colored pattern or colored coating film is adjusted so that the maximum transmittance at wavelengths of 400 to 500 nm is 83%, the transmittance at 530 nm is preferably 13.0% or less, more preferably 11.0% or less, even more preferably 8.0% or less, and particularly preferably 6.0% or less or 4.0% or less. By reducing the transmittance at 530 nm, leakage of green light can be suppressed, and the color separation properties of the blue color filter can be improved. The lower limit of the transmittance at 530 nm is not particularly limited, and may be, for example, 0.5% or more.

[0211] Furthermore, when the thickness of the colored pattern or colored coating film is adjusted so that the maximum transmittance at wavelengths of 400 to 500 nm is 83%, the transmittance at 640 nm is preferably 10.0% or less, more preferably 5.0% or less, and even more preferably 3.5% or less, and can also be 2.0% or less. By reducing the transmittance at 640 nm, leakage of red light can be suppressed, and the color separation ability as a blue color filter can be further improved. The lower limit of the transmittance at 640 nm is not particularly limited, and may be, for example, 0.5% or more.

[0212] Furthermore, when the thickness of the colored pattern or colored coating film is adjusted so that the maximum transmittance at wavelengths of 400 to 500 nm is 83%, the absolute value of the slope of the transmittance spectrum, as determined by the method described in the Examples below, is preferably 0.013 or more, more preferably 0.015 or more, and even more preferably 0.017 or more. By increasing the absolute value of the slope, a color filter with a high amount of transmitted light can be produced, thereby increasing the sensitivity of a solid-state imaging device including the color filter. The upper limit of the absolute value of the slope is not particularly limited, and may be, for example, 0.05 or less. [Example]

[0213] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and can of course be practiced with appropriate modifications within the scope of the above and below-described aims, all of which are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

[0214] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).

[0215] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of analytical sample: 0.001 to 0.01% Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0216] <Colorant Synthesis Example 1> 40.5 parts of the compound represented by formula (II-X) and 60.5 parts of 2,6-xylidine (Tokyo Chemical Industry Co., Ltd.) were mixed under light-shielded conditions and stirred in 200 parts of N-methylpyridone at 150°C for 8 hours. The resulting reaction solution was cooled to room temperature and then added to a mixture of 1200 parts of water and 75 parts of 35% hydrochloric acid. The mixture was stirred at room temperature for 1 hour, resulting in the precipitation of crystals. The precipitated crystals were collected as a residue by suction filtration, washed with 100 parts of methanol, and then dried under reduced pressure at 60°C for 12 hours to obtain 49 parts of the compound represented by formula (II-1). The yield was 85%.

[0217] [ka]

[0218] Identification of the compound represented by formula (II-1) (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 575 Exact Mass: 574

[0219] <Colorant Synthesis Example 2> 2,6-Diphenylaniline was synthesized with reference to the method described in ARKIVOC, 2012, 9, 62-75. 4.0 parts of the compound represented by formula (II-X), 9.69 parts of 2,6-diphenylaniline, 2.69 parts of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.), and 24 parts of sulfolane (Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 250 °C, and stirred for 4 hours. After cooling the reaction solution to room temperature, 48 parts of 1 N hydrochloric acid was added. The resulting precipitate was collected as a residue by suction filtration and washed sequentially with 24 parts of toluene, 18 parts of N,N-dimethylformamide, and 20 parts of N,N-dimethylformamide. The resulting residue was dried to obtain 5.18 parts of the compound represented by formula (II-2). The yield was 64%.

[0220] [ka]

[0221] Identification of the compound represented by formula (II-2) (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 823.3 Exact Mass: 823.3

[0222] <Resin Synthesis Example 1: Synthesis of Resin (B-1)> A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with nitrogen to replace the atmosphere, and 340 parts of propylene glycol monomethyl ether acetate was added, followed by heating to 80°C with stirring. Next, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 54 parts of a mixture of decan-9-yl acrylate (1:1 molar ratio), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 40 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition of the initiator solution was completed, the mixture was kept at 80°C for 3 hours and then cooled to room temperature, yielding a copolymer (resin (B-1)) solution with a viscosity of 127 mPa·s measured with a Brookfield viscometer (23°C) and a solids content of 37.0%. The weight-average molecular weight Mw of the resulting copolymer was 9.4×10 3 The resin (B-1) had the following structural units: a polydispersity of 1.89, and an acid value calculated as solid content of 114 mg-KOH / g.

[0223] [ka]

[0224] <Resin Synthesis Example 2: Synthesis of Resin (B-2)> 241 parts of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The mixture was stirred while purging with nitrogen and heated to 130°C. Next, a monomer mixture consisting of 73 parts of 2-ethylhexyl acrylate, 145 parts of glycidyl methacrylate, and 10 parts of dicyclopentanyl methacrylate, plus 34 parts of tert-butyl peroxy-2-ethylhexanoate, was added dropwise from the dropping funnel to the flask over 2 hours. After the dropwise addition was completed, the mixture was stirred for an additional 30 minutes to allow the copolymerization reaction to proceed. The atmosphere in the flask was then purged with air, and 74 parts of acrylic acid, 1 part of triphenylphosphine, and 1 part of methoquinone were added. The reaction was continued for 10 hours at 120°C. Next, 65 parts of succinic anhydride was added to the reaction system, and the reaction was continued for an additional 1.5 hours to obtain a polymer. Finally, 300 parts of propylene glycol monomethyl ether was added to the reaction solution, followed by propylene glycol monomethyl ether acetate, to obtain a copolymer (Resin (B-2)) solution with a viscosity of 26 mPa·s measured with a Brookfield viscometer (23°C) and a solids content of 38.5%. The weight-average molecular weight Mw of the resulting copolymer was 6600, and the acid value calculated as solids was 92.5 mg-KOH / g.

[0225] <Dispersion preparation examples 1 to 7> Colorant dispersions (A-1) to (A-7) were obtained by mixing the components in the blending ratios shown in Table 1 and dispersing them using a bead mill. In Table 1, resin (B-1) represents resin (B-1) (solid content equivalent) obtained in Resin Synthesis Example 1, PGME represents propylene glycol monomethyl ether, and PGMEA represents propylene glycol monomethyl ether acetate. CI Acid Red 289 is a mixture of a compound represented by formula (II-3) and a compound represented by formula (II-4), and CI Acid Red 52 is a compound represented by formula (II-5).

[0226] [ka]

[0227] [Table 1]

[0228] <Measurement of maximum absorption wavelength of xanthene dye> In a measuring flask, 0.005 g of each compound shown in Table 2 was dissolved in dimethylformamide to a volume of 0.1 L, and 0.01 L of this solution was diluted with chloroform to a volume of 0.25 L (concentration: 0.002 g / L). The absorption spectrum was measured in the wavelength range of 800 to 300 nm using a UV-visible spectrophotometer (V-650DS; manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm), and the maximum absorption wavelength was determined. The maximum absorption wavelength of each compound is shown in Table 2.

[0229] [Table 2]

[0230] [Examples 1 to 6 and Comparative Examples] <Preparation of Colored Curable Resin Composition> The components were mixed in the blending ratios (by mass) shown in Table 3 to obtain colored curable resin compositions.

[0231] [Table 3]

[0232] Colorant dispersion (A-1): Colorant dispersion (A-1) obtained in Dispersion Preparation Example 1 Colorant dispersion (A-2): Colorant dispersion (A-2) obtained in Dispersion Preparation Example 2 Colorant dispersion (A-3): Colorant dispersion (A-3) obtained in Dispersion Preparation Example 3 Colorant dispersion (A-4): Colorant dispersion (A-4) obtained in Dispersion Preparation Example 4 Colorant dispersion (A-5): Colorant dispersion (A-5) obtained in Dispersion Preparation Example 5 Colorant dispersion (A-6): Colorant dispersion (A-6) obtained in Dispersion Preparation Example 6 Colorant dispersion (A-7): Colorant dispersion (A-7) obtained in Dispersion Preparation Example 7 Resin solution (B-2): Resin (B-2) solution obtained in Resin Synthesis Example 2 Polymerizable compound (C-1): A compound represented by the following formula (NK Ester A-DPH-12E: manufactured by Shin-Nakamura Chemical Co., Ltd.) [ka] Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (trade name PBG-327: O-acyloxime compound; manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) Solvent (E-1): Propylene glycol monomethyl ether acetate Leveling agent (F-1): Polyether-modified silicone oil (product name: Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

[0233] <Formation of colored patterns (color filters)> A colored curable resin composition was applied to the surface of a 4-inch glass substrate by spin coating, and then prebaked at 100°C for 2 minutes to obtain a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was exposed to 1500 J / m using an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation). 2 The colored composition layer after the light irradiation was immersed and developed in an aqueous developer containing 0.3% tetramethylammonium hydroxide at 23°C for 30 seconds, washed with water, and then post-baked on a hot plate at 220°C for 5 minutes to produce a colored pattern. The film thickness of the colored pattern was adjusted so that the maximum transmittance at wavelengths of 400 to 500 nm was 83%.

[0234] <Film thickness measurement> The film thickness of the obtained colored patterns was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.) The film thickness of the colored patterns obtained in Examples 1 to 6 and the Comparative Example was all 0.6 μm.

[0235] <Transmittance evaluation> The transmittance of the obtained colored pattern was measured in 1 nm increments in the wavelength range of 380 nm to 780 nm using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation).

[0236] (1) Transmittance at 530 nm From the above measurement results, the transmittance of each colored pattern at 530 nm was confirmed. The results are shown in Table 4. The lower the transmittance at 530 nm, the less green light leaks, and the better the color separation performance of the color filter (especially the blue color filter).

[0237] [Table 4]

[0238] (2) Transmittance at 640 nm From the above measurement results, the transmittance at 640 nm of each colored pattern was confirmed. The results are shown in Table 5. The lower the transmittance at 640 nm, the less red light leaks, and the better the color separation performance of the color filter (especially the blue color filter).

[0239] [Table 5]

[0240] (3) Transmittance spectrum slope From the above measurement results, the spectral slope was calculated from the wavelengths at which the transmittance was 70% and 20% on the longer wavelength side of the maximum transmittance. The results are shown in Table 6. The larger the absolute value of the spectral slope, the greater the amount of transmitted light that can be produced in a color filter, and the greater the sensitivity of a solid-state imaging device including the color filter.

[0241] [Table 6]

Claims

1. Contains a colorant, a resin, a polymerizable compound, and a polymerization initiator, The colored curable resin composition, wherein the colorant comprises a xanthene dye (a1) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3).

2. The colored curable resin composition according to claim 1, wherein the content ratio (a1 / a2) of the xanthene dye (a1) to the xanthene dye (a2) is 0.1 to 15 on a mass basis.

3. 2. The colored curable resin composition according to claim 1, wherein a total content of the xanthene colorant (a1) and the xanthene colorant (a2) is 8 parts by mass or more relative to 100 parts by mass of the blue pigment (a3).

4. 2. The colored curable resin composition according to claim 1, wherein a content of the colorant is 35 mass% or more relative to a total amount of solids in the colored curable resin composition.

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

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

7. A solid-state imaging device comprising the color filter according to claim 5 .

Images