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 reducing crosstalk of color filters.SOLUTION: The present invention relates to a coloring curable resin composition including a colorant, a resin, a polymerizable compound, and a polymerization initiator, in which the colorant includes C. I. Pigment Yellow 185, a xanthene colorant, and at least one selected from the group consisting of a red pigment and an orange pigment.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, a display device including the color filter, and a solid-state imaging device including the color filter. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, organic electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored resin compositions. Various colorants are used in such colored resin compositions, and for example, CI Pigment Red 254, CI Pigment Red 242, CI Pigment Yellow 139, and CI Pigment Yellow 185 are known to be used as colorants (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2023-39409 Summary of the Invention [Problem to be solved by the invention]

[0004] When color filters are used together with sensors such as solid-state imaging devices, pixels need to be made smaller as resolution increases. However, there is a problem in that light passing through a specific color filter leaks into filter areas of other colors (e.g., crosstalk), making it impossible to increase the quantum efficiency of the pixel. Therefore, an object of the present invention is to provide a colored curable resin composition that can reduce crosstalk in a color filter. [Means for solving the problem]

[0005] That is, the gist of the present invention is as follows. [1] A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant comprises CI Pigment Yellow 185, a xanthene dye, and at least one pigment selected from the group consisting of a red pigment and an orange pigment. [2] The colored curable resin composition according to [1], wherein the content of the xanthene colorant is 1% by mass or more and 40% by mass or less, based on the total amount of the colorants. [3] The colored curable resin composition according to [1] or [2], wherein the total content of at least one pigment selected from the group consisting of a red pigment and an orange pigment is 10% by mass or more and 65% by mass or less, based on the total amount of colorants. [4] The colored curable resin composition according to any one of [1] to [3], wherein the content of CI Pigment Yellow 185 is 6% by mass or more and 50% by mass or less, based on the total amount of colorants. [5] The colored curable resin composition according to any one of [1] to [4], wherein the red pigment and the orange pigment include pigments having one or more skeletons selected from the group consisting of a diketopyrrolopyrrole skeleton and an azo skeleton. [6] A color filter formed from the colored curable resin composition according to any one of [1] to [5]. [7] The color filter according to [6], wherein in a transmission spectrum with wavelength on the horizontal axis and transmittance on the vertical axis, the slope calculated from the following formula based on the minimum wavelength λ1 that satisfies a transmittance of 70% or more in the wavelength range of 580 nm or more, the transmittance T1 at this wavelength λ1, the maximum wavelength λ2 that satisfies a transmittance of 30% or less in the wavelength range of less than 580 nm, and the transmittance T2 at this wavelength λ2 is 0.03 to 0.06: Slope = (T1-T2) / (λ1-λ2) [8] A display device comprising the color filter according to [6] or [7]. [9] A solid-state imaging device comprising the color filter according to [6] or [7]. [Effects of the Invention]

[0006] According to the present invention, it is possible to reduce crosstalk in color filters. DETAILED DESCRIPTION OF THE INVENTION

[0007] [Colored curable resin composition] The present invention encompasses a colored curable resin composition containing 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 colorant (A) contains CI Pigment Yellow 185, a xanthene dye, and at least one pigment selected from the group consisting of a red pigment and an orange pigment. Use of such a colored curable resin composition allows for the production of a color filter with reduced crosstalk, preferably a color filter with reduced crosstalk and prevention of color mixing into green. The colored curable resin composition of the present invention may contain a solvent (hereinafter, may be referred to as solvent (E)). The colored curable resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.

[0008] In the present invention, based on the following conditions, a red pigment is defined as one having a maximum absorption wavelength of more than 500 nm, and an orange pigment is defined as one having a maximum absorption wavelength of more than 460 nm and not more than 500 nm. [Conditions] A colored curable resin composition containing only one colorant is prepared, with the colorant content being 10 mass % of the solid content of the composition. A color filter having a thickness of 1 μm formed from the composition is measured for absorbance in the visible light region (wavelength 400 to 780 nm).

[0009] <Colorant (A)> A xanthene dye is a compound having a xanthene skeleton in the molecule. Examples of xanthene dyes include CI Acid Red 50, 51 (hereinafter, the term CI Acid Red will be omitted and only the numbers will be used. The same applies to the others.), 52, 87, 91, 92, 94, 95, 98, 289, 388, CI Acid Violet 9, 30, 102, CI Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, CI Basic Violet 10 (Rhodamine B), 11, CI Solvent Red 218, CI Mordant Red 27, CI Reactive Red 36 (Rose Bengal B), sulforhodamine G, CI Pigment Red 81, 169, 173, CI Pigment Violet 1, 2, the xanthene dyes described in JP-A-2010-32999 and the xanthene dyes described in Japanese Patent No. 4,492,760.

[0010] The xanthene dye preferably contains a compound represented by formula (1): 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(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 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 10The 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, an alkyl group having 1 to 10 carbon atoms is preferred, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group. The alkylphenyl group is preferably a group having an alkyl group in 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 an alkyl group in the two bonding positions that are ortho-positions relative to the N bonded to the phenyl group. In particular, xanthene dyes are 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.

[0018] Examples of aryl groups constituting the arylphenyl group include phenyl groups and alkylphenyl groups such as tolyl, xylyl, mesityl, propylphenyl, and butylphenyl groups, among which aryl groups having 6 to 10 carbon atoms are preferred, and phenyl groups are more preferred.The arylphenyl group is preferably a group having an aryl group in 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 in two bonding positions that are ortho-positions relative to the N bonded to the phenyl group.

[0019] In particular, R 1 ~R 4 Examples 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.

[0020] 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 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.

[0021] Z +is the ammonium cation, Na + or K + is preferred, and more preferably an ammonium cation. The ammonium cation is NH4 + The term "ammonium cation" refers to organic ammonium cations such as, but not limited to, primary ammonium cations, secondary ammonium cations, tertiary ammonium cations, and quaternary ammonium cations, among which quaternary ammonium cations are preferred. Ammonium cations 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.

[0022] 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.

[0023] -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.

[0024] -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.

[0025] -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.

[0026] -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.

[0027] -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.

[0028] -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-1-substituted sulfamoyl groups such as an N-(2-methylbutyl)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, and an N-(2-ethylhexyl)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, and N,N-butylethylsulfamoyl group; and the like.

[0029] R 12 Examples 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.

[0030] R 12The -CH2- contained in the alkanediyl group represented by the formula 8 It may be substituted by -, -OCO-, -COO-, -OCONH-, -CONH- or -NHCO-.

[0031] 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.

[0032] 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.

[0033] [ka]

[0034] R 1 ~R 4 are 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.

[0035] In particular, 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, 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.

[0036] 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.

[0037] 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.

[0038] R 6 ~R 7 are each independently preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom.

[0039] 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 + and even more preferably -SO3 - is.

[0040] m is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0041] 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.

[0042] Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0043] In formula (1), -SO3 in the form of ions - The number of is preferably 0 or 1, and more preferably 1.

[0044] a represents 0 or 1, and is preferably 0.

[0045] 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.

[0046] 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:

[0047] The xanthene dye more preferably contains a compound represented by formula (1-A): The compound represented by formula (1-A) may be a tautomer thereof.

[0048] [ka]

[0049] [In formula (1-A), 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.]

[0050] In formula (1-A), a, m, X, and Z + a, m, X, and Z in formula (1), including preferred embodiments thereof. + is the same as:

[0051] R 21 ~R 22 and R 29 ~R 30 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.

[0052] R 21 and R 22 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 4Examples 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.

[0053] 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 or an alkyl group having 2 to 4 carbon atoms which may have a carboxy group.

[0054] R 29 and R 30 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. 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.

[0055] 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.

[0056] 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.

[0057] R 23 and R 24 are each independently preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, more 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.

[0058] 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.

[0059] 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.

[0060] R 25 is -SO3 - It is particularly preferred that:

[0061] In formula (1-A), -SO3 in the form of an ion - The number of is preferably 0 or 1, and more preferably 1.

[0062] The compound represented by formula (1-A) is preferably electrically neutral, i.e., in the form of an ion -SO3 - When the compound represented by formula (1-A) has one ionic form of -SO3, it is preferable that a is 0. - When there is no a, it is preferred that a is 1.

[0063] The compound represented by formula (1-A) 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:

[0064] Examples of xanthene dyes include compounds represented by formulas (1-1) to (1-54): In the following formulas, Ra represents a 2-ethylhexyl group.

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] Other xanthene dyes include those described in JP-A-2017-194551.

[0073] Among them, the xanthene dye is preferably a compound represented by formula (1-17) to formula (1-32), more preferably a compound represented by formula (1-17) to formula (1-28) and formula (1-32), and even more preferably a compound represented by formula (1-32).

[0074] The colorant may contain one or more xanthene dyes.

[0075] The colorant (A) contains at least one selected from the group consisting of a red pigment and an orange pigment, preferably contains at least an orange pigment, and more preferably contains both a red pigment and an orange pigment. Examples of red pigments and orange pigments include: 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; etc.

[0076] The red pigment and the orange pigment preferably contain a pigment having one or more selected from the group consisting of a diketopyrrolopyrrole skeleton and an azo skeleton. The red pigment more preferably contains a pigment having a diketopyrrolopyrrole skeleton. The orange pigment more preferably contains a pigment having an azo skeleton.

[0077] As the pigment having a diketopyrrolopyrrole skeleton, a compound represented by formula (i) is preferred.

[0078] [ka] [In formula (i), R 1 ~R 10 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group having 1 to 15 carbon atoms, -OR 11 , -SR 11 , -SO3M, -SO2NHR 11 , -SO2N(R 12 )2, -N(R 11 )2. R 11 represents a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms. R 12 represents a hydrocarbon group having 1 to 15 carbon atoms. M represents a hydrogen atom or an alkali metal atom.

[0079] The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, more preferably a fluorine atom, a chlorine atom or a bromine atom, and even more preferably a chlorine atom or a bromine atom.

[0080] R 1 ~R 10 The hydrocarbon group having 1 to 15 carbon atoms represented by the formula (I) may be saturated or unsaturated, and is preferably an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and is also preferably a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group.

[0081] The aliphatic hydrocarbon group is preferably a linear or branched alkyl group, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, an octadecyl group, a 1,5-dimethylhexyl group, a 1,6-dimethylheptyl group, or a 2-ethylhexyl group. The aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, even more preferably 1 to 8 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms.

[0082] The aromatic hydrocarbon group is preferably a phenyl group or an alkylphenyl group such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group or a butylphenyl group, and more preferably a phenyl group. The aromatic hydrocarbon group preferably has 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 9 carbon atoms, including the carbon atoms of the substituent. The aromatic hydrocarbon group may be substituted, and may have a substituent such as a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, a carbamoyl group, a sulfamoyl group, or an alkoxyl group having 1 to 4 carbon atoms. The substituted aromatic hydrocarbon group is preferably a p-methylphenyl group, a 4-tert-butylphenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a p-chlorophenyl group, a 2,4-dichlorophenyl group, or a 3-carbamoylphenyl group.

[0083] The combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group is preferably an aralkyl group such as a benzyl group, a 4-methylbenzyl group, a 4-tert-butylbenzyl group, a 4-methoxybenzyl group, a 4-nitrobenzyl group, or a 2,4-dichlorobenzyl group.

[0084] R 11 and R 12 The hydrocarbon group having 1 to 15 carbon atoms represented by R 1 ~R 10 The preferred range may be the same as the hydrocarbon group having 1 to 15 carbon atoms represented by the following formula:

[0085] -OR 11 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.

[0086] -SR 11 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.

[0087] -SO2NHR 11 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 N-substituted sulfamoyl groups such as a 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.

[0088] -SO2N(R 12 )2 includes N,N-disubstituted sulfamoyl groups such as an N,N-dimethylsulfamoyl group, an N,N-ethylmethylsulfamoyl group, an N,N-diethylsulfamoyl group, an N,N-propylmethylsulfamoyl group, an N,N-isopropylmethylsulfamoyl group, an N,N-tert-butylmethylsulfamoyl group, an N,N-butylethylsulfamoyl group, an N,N-bis(1-methylpropyl)sulfamoyl group, and an N,N-heptylmethylsulfamoyl group.

[0089] -N(R 11 )2 is, amino group; mono-substituted amino groups such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-(sec-butyl)amino group, an N-(tert-butyl)amino group, an N-pentylamino group, an N-(1-ethylpropyl)amino group, an N-hexylamino group, an N-(2-ethylhexyl)amino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, or an N-phenylamino group;

[0090] N,N-Dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-propyl-N-methylamino group, N,N-dipropylamino group, N-isopropyl-N-methylamino group, N,N-diisopropylamino group, N,N-diisobutylamino group, N,N-di(sec-butyl)amino group, N-(tert-butyl)-N-methylamino group, N,N-di(tert-butyl)amino group, N-butyl-N-methylamino group, N,N-dibutylamino group, N-butyl-N-octyl and di-substituted amino groups such as an amino group, an N,N-dipentylamino group, an N,N-bis(1-ethylpropyl)amino group, an N-butyl-N-hexylamino group, an N-hexyl-N-methylamino group, an N,N-dihexylamino group, an N-(2-ethylhexyl)-N-methylamino group, an N,N-bis(2-ethylhexyl)amino group, an N,N-diheptylamino group, an N-octyl-N-methylamino group, an N,N-dioctylamino group, an N-phenyl-N-methylamino group, and an N,N-diphenylamino group.

[0091] The alkali metal atom represented by M in the above -SO3M is preferably sodium or potassium.

[0092] Among them, R 1 ~R 10 preferably each independently represents a hydrogen atom, a halogen atom, a cyano group, or a hydrocarbon group having 1 to 15 carbon atoms, and more preferably represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 10 carbon atoms.

[0093] In a preferred embodiment, R 1 ~R 5 At least one of R is a halogen atom or a hydrocarbon group having 1 to 15 carbon atoms, and R 6 ~R 10 At least one of R is preferably a halogen atom or a hydrocarbon group having 1 to 15 carbon atoms, 1 ~R 5 at least one of R is a halogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and 6 ~R 10 More preferably, at least one of R is a halogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and 1 ~R 5 at least one of R is a halogen atom or an aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 10 carbon atoms, and 6 ~R 10 It is more preferable that at least one of them is a halogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group. When there are a plurality of halogen atoms or aliphatic hydrocarbon groups having 1 to 10 carbon atoms, the halogen atoms or aliphatic hydrocarbon groups having 1 to 10 carbon atoms may be the same or different.

[0094] The compound represented by formula (i) is more preferably a compound represented by formula (i-1).

[0095] [ka] [In formula (i-1), R 3 and R 8 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group having 1 to 15 carbon atoms, -OR 11 , -SR 11 , -SO3M, -SO2NHR 11 , -SO2N(R 12 )2, -N(R 11 )2. R 11 represents a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms. R12 represents a hydrocarbon group having 1 to 15 carbon atoms. M represents a hydrogen atom or an alkali metal atom.

[0096] R 3 , R 8 , R 11 , R 12 , M are the same as above.

[0097] In formula (i) or formula (i-1), R 3 and R 8 are each independently preferably a halogen atom or a hydrocarbon group having 1 to 15 carbon atoms, more preferably a halogen atom, an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a chlorine atom, a bromine atom, a linear alkyl group having 1 to 10 carbon atoms, or a phenyl group. When there are multiple halogen atoms or hydrocarbon groups, the halogen atoms or hydrocarbon groups may be the same or different.

[0098] The compound represented by formula (i) or formula (i-1) is preferably CI Pigment Red 254, CI Pigment Red 272, CI Pigment Red 291, or the like.

[0099] As the pigment having an azo skeleton, a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) and a compound represented by formula (II) (hereinafter sometimes referred to as compound (II)) are preferred. Compound (I) will be described in detail below, but compound (I) also includes the resonance structure of formula (I), tautomers of formula (I), and compounds obtained by rotating each group in formula (I) around the bond axis of the single bond.

[0100] [ka] [In formula (I), X 1represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic hydrocarbon group, an optionally substituted heterocyclic group, or -CONR 5 R 6 Represents. X 2 represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, -OR 1 , or -COOR 2 Represents. X 3 represents a halogen atom, a cyano group, a nitro group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, -OR 3 , -COOR 4 , -CONR 5 R 6 , or -SO2NR 7 R 8 Represents. R 1 ~R 8 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. l represents an integer of 0 to 4. n represents 1 or 2; m represents an integer of 0 to 5, The sum of m and n is an integer of 6 or less. X 1 , X 2 , or X 3 When there are multiple, they may be the same or different.

[0101] X 1 The aliphatic hydrocarbon group represented by the formula (I) may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0102] Examples of saturated or unsaturated chain hydrocarbon groups include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups; Isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl, 4-methyl branched alkyl groups such as 1-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl, and 1-butylhexyl; Ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1,3-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,2-dimethyl-1-propenyl group, pentenyl group (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4 alkenyl groups such as 1-pentenyl group, 1-(1,1-dimethylethyl)ethenyl group, 1,3-dimethyl-1-butenyl group, hexenyl group (e.g., 1-hexenyl group, 5-hexenyl group), heptenyl group (e.g., 1-heptenyl group, 6-heptenyl group), octenyl group (e.g., 1-octenyl group, 7-octenyl group), nonenyl group (e.g., 1-nonenyl group, 8-nonenyl group), decenyl group (e.g., 1-decenyl group, 9-decenyl group), undecenyl group, and dodecenyl group; alkynyl groups such as an ethynyl group, a propynyl group (e.g., a 1-propynyl group, a 2-propynyl group), an octynyl group (e.g., a 1-octynyl group, a 7-octynyl group), a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, a nonynyl group, a decynyl group, an undecynyl group, and a dodecynyl group; etc. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 12, and particularly preferably 1 to 9. Of these, a linear or branched chain alkyl group having 1 to 9 carbon atoms is particularly preferred.

[0103] Examples of saturated or unsaturated alicyclic hydrocarbon groups include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 2,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, a 2,6 ... Examples of such groups include cycloalkyl groups such as methylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, and 4,4-dimethylcyclohexyl; cycloalkenyl groups such as cyclohexenyl groups (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl), cycloheptenyl, and cyclooctenyl; and saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl, and bicyclo[2.2.2]octyl.

[0104] The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, even more preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms.

[0105] X1 Examples of the aromatic hydrocarbon group represented by the formula (I) include aryl groups such as phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, and biphenyl; alkylaryl groups such as o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-6-ethylphenyl, 2,6-diethylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2-methyl-6-isopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, and p-tert-butylphenyl; and alkenylaryl groups such as 4-vinylphenyl.

[0106] X 1 The aromatic hydrocarbon group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, even more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0107] X 1 The heterocyclic group represented by X may be a monocyclic or polycyclic ring, and may be a saturated or unsaturated ring. 1 The heterocyclic group represented by the formula (I) is preferably a heterocyclic group containing a heteroatom other than carbon atoms as a ring component. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0108] X 1 The heterocyclic group represented by the following formula (I) preferably has 2 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, and even more preferably 3 to 15 carbon atoms.

[0109] Examples of heterocyclic groups containing only nitrogen atoms as heteroatoms include monocyclic heterocyclic groups such as pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolidinyl, piperidyl, and piperazinyl groups; and polycyclic heterocyclic groups such as indolizinyl, indolyl, 1H-indazolyl, isoquinolyl, quinolyl, phthalazinyl, carbazolyl, acridinyl, indolinyl, and isoindolinyl groups. Examples of heterocyclic groups containing only oxygen atoms as heteroatoms include monocyclic heterocyclic groups such as a furyl group and a pyranyl group; and polycyclic heterocyclic groups such as an isobenzofuranyl group, a chromenyl group, a xanthenyl group and a chromanyl group; and the like. Examples of heterocyclic groups containing only sulfur atoms as heteroatoms include monocyclic heterocyclic groups such as thienyl groups; and polycyclic heterocyclic groups such as benzo[b]thienyl groups and thianthrenyl groups. Examples of heterocyclic groups containing a nitrogen atom and an oxygen atom as hetero atoms include monocyclic heterocyclic groups such as an oxazolyl group; and polycyclic heterocyclic groups such as a benzimidazolonyl group.

[0110] X 1 Among the heterocyclic groups represented by the formula (I), polycyclic heterocyclic groups are preferred, and polycyclic heterocyclic groups having a benzene ring such as a benzo[b]thienyl group, a thianthrenyl group, an isobenzofuranyl group, a chromenyl group, a xanthenyl group, an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, a chromanyl group, an indolinyl group, an isoindolinyl group, or a benzimidazolonyl group are more preferred.

[0111] X 1 -CONR, which is represented by 5 R 6is, for example, a carbamoyl group; an N-1-substituted carbamoyl group such as an N-methylcarbamoyl group, an N-ethylcarbamoyl group, an N-propylcarbamoyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, an N-sec-butylcarbamoyl group, an N-tert-butylcarbamoyl group, an N-pentylcarbamoyl group, or an N-phenylcarbamoyl group; an N,N-dimethylcarbamoyl group, an N,N-ethylmethylcarbamoyl group, an N,N-diethylcarbamoyl group, or an N-isopropylcarbamoyl group; and N,N-disubstituted carbamoyl groups such as an N,N-di-isopropylcarbamoyl group, an N,N-propylmethylcarbamoyl group, an N,N-dipropylcarbamoyl group, an N,N-isopropylmethylcarbamoyl group, an N,N-diisopropylcarbamoyl group, an N,N-tert-butylmethylcarbamoyl group, an N,N-diisobutylcarbamoyl group, an N,N-di-sec-butylcarbamoyl group, an N,N-di-tert-butylcarbamoyl group, an N,N-butylmethylcarbamoyl group, and an N,N-diphenylcarbamoyl group.

[0112] X 2 , X 3 , and R 1 ~R 8 Examples of the hydrocarbon group represented by the formula (I) include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0113] Examples of saturated or unsaturated chain hydrocarbon groups include straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-icosyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, and the like. branched alkyl groups such as (1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, and (2-ethyl)octyl group; alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, and 2-pentenyl group; and the like.

[0114] Examples of saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, and bicyclo[2.2.2]octyl.

[0115] The aromatic hydrocarbon group may be any of the above-mentioned X 1 Examples of the aromatic hydrocarbon group include the same groups as those represented by the following formula:

[0116] The hydrocarbon group having 1 to 20 carbon atoms may be a group formed by combining two or more selected from the group consisting of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the carbon number is 20. Examples of such groups include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, and 3,4-dimethylcyclohexyl groups; Alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded, such as a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, a 4,4-dimethylcyclohexyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, or a 3,3,5,5-tetramethylcyclohexyl group; and alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, or a cyclohexylethyl group.

[0117] X 1 aliphatic hydrocarbon groups, aromatic hydrocarbon groups and heterocyclic groups represented by the formula: X 2 and hydrocarbon groups represented by X 3Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include a halogen atom, a hydroxy group, an alkoxy group, an alkylsulfanyl group, a formyl group, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a nitro group, a cyano group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted sulfamoyl group, -SO3M, etc. The M represents a hydrogen atom or an alkali metal atom (e.g., sodium, potassium).

[0118] The aliphatic hydrocarbon group having a halogen atom as a substituent is X 1 and a halogen atom bonded to an aliphatic hydrocarbon group represented by the following formula (I):

[0119] The aromatic hydrocarbon group having a halogen atom as a substituent is X 1 and a halogen atom bonded to an aromatic hydrocarbon group represented by the following formula:

[0120] Examples of the heterocyclic group having a halogen atom as a substituent include X 1 Examples of the heterocyclic group include those in which a halogen atom is bonded to a heterocyclic group represented by the following formula:

[0121] Examples of combinations of aromatic hydrocarbon groups and aliphatic hydrocarbon groups having halogen atoms as substituents include a (2,4-dichlorophenyl)methyl group, a (4-fluorophenyl)methyl group, a (3,5-difluorophenyl)methyl group, a 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl group, a (phenoxy)(phenyl)methyl group, and a (benzyloxy)(phenyl)methyl group.

[0122] Examples of the alkoxy group as a substituent include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a tert-butoxy group, etc. The alkoxy group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.

[0123] Examples of the alkylsulfanyl group as a substituent include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an n-butylsulfanyl group, etc. The alkylsulfanyl group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.

[0124] The substituted amino group as a substituent includes an amino group having one or two hydrocarbon groups. Examples of the hydrocarbon group include the groups exemplified above as the hydrocarbon group having 1 to 20 carbon atoms, and are preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms. Examples of the substituted amino group include N-1 substituted amino groups such as N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, and N-phenylamino; and N,N-2 substituted amino groups such as N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-diisopropylamino, N,N-diphenylamino, N,N-ethylmethylamino, N,N-methylphenylamino, and N,N-ethylphenylamino.

[0125] The N-acylamino group as a substituent is -NHCOR 9a R 9a represents a hydrogen atom or a hydrocarbon group. 9a Examples of the hydrocarbon group represented by R include the groups exemplified above as hydrocarbon groups having 1 to 20 carbon atoms. 9a is preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. Examples of the N-acylamino group include an N-formylamino group, an N-acetylamino group, an N-propanoylamino group, an N-butanoylamino group, and an N-benzoylamino group.

[0126] The substituted or unsubstituted carbamoyl group as a substituent is -CONR 9b R 9c R 9b , R 9c R each independently represents a hydrogen atom or a hydrocarbon group. 9b , R 9c Examples of the hydrocarbon group represented by R include the groups exemplified above as hydrocarbon groups having 1 to 20 carbon atoms. 9b , R 9c are preferably each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. 9b R 9c Examples of the alkyl group include a carbamoyl group; N-1-substituted carbamoyl groups such as an N-methylcarbamoyl group, an N-ethylcarbamoyl group, an N-propylcarbamoyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-tert-butylcarbamoyl group, and an N-phenylcarbamoyl group; and N,N-2-substituted carbamoyl groups such as an N,N-dimethylcarbamoyl group, an N,N-ethylmethylcarbamoyl group, an N,N-diethylcarbamoyl group, an N,N-propylmethylcarbamoyl group, an N,N-dipropylcarbamoyl group, an N,N-butylmethylcarbamoyl group, an N,N-tert-butylmethylcarbamoyl group, an N,N-di-tert-butylcarbamoyl group, an N,N-phenylmethylcarbamoyl group, and an N,N-diphenylcarbamoyl group.

[0127] The substituted or unsubstituted sulfamoyl group as a substituent is -SO2NR 9d R 9e R 9d , R 9e R each independently represents a hydrogen atom or a hydrocarbon group. 9d , R 9e Examples of the hydrocarbon group represented by R include the groups exemplified above as hydrocarbon groups having 1 to 20 carbon atoms. 9d , R 9eare preferably each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. 9d R 9e Examples of the sulfamoyl group include a sulfamoyl group; N-1-substituted sulfamoyl groups such as an N-methylsulfamoyl group, an N-ethylsulfamoyl group, an N-propylsulfamoyl group, an N-isopropylsulfamoyl group, an N-butylsulfamoyl group, and an N-isobutylsulfamoyl group; and N,N-2-substituted sulfamoyl groups such as an N,N-dimethylsulfamoyl group, an N,N-ethylmethylsulfamoyl group, an N,N-diethylsulfamoyl group, an N,N-propylmethylsulfamoyl group, an N,N-isopropylmethylsulfamoyl group, an N,N-tert-butylmethylsulfamoyl group, an N,N-butylethylsulfamoyl group, and an N,N-dibutylsulfamoyl group.

[0128] X 2 -OR 1 , and X 3 -OR 3 Examples of the alkyl group include a hydroxy group; an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and a pentyloxy group; and the like.

[0129] X 2 -COOR represented by 2 , and X 3 -COOR represented by 4 Examples of the alkyl group include a carboxy group; an alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, and a pentyloxycarbonyl group; and the like.

[0130] X 3 -CONR, which is represented by 5 R 6Examples of the aryl group include a carbamoyl group; N-substituted carbamoyl groups such as an N-methylcarbamoyl group, an N-ethylcarbamoyl group, an N-propylcarbamoyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, an N-sec-butylcarbamoyl group, an N-tert-butylcarbamoyl group, and an N-pentylcarbamoyl group; an N,N-dimethylcarbamoyl group, an N,N-ethylmethylcarbamoyl group, and an N,N-diethyl N,N-disubstituted carbamoyl groups such as a carbamoyl group, an N,N-propylmethylcarbamoyl group, an N,N-dipropylcarbamoyl group, an N,N-isopropylmethylcarbamoyl group, an N,N-diisopropylcarbamoyl group, an N,N-tert-butylmethylcarbamoyl group, an N,N-diisobutylcarbamoyl group, an N,N-disec-butylcarbamoyl group, an N,N-di-tert-butylcarbamoyl group, and an N,N-butylmethylcarbamoyl group.

[0131] X 3 Represented by -SO2NR 7 R 8 Examples of the sulfamoyl group include a sulfamoyl group; an N-1-substituted sulfamoyl group such as an N-methylsulfamoyl group, an N-ethylsulfamoyl group, an N-propylsulfamoyl group, an N-isopropylsulfamoyl group, an N-butylsulfamoyl group, an N-isobutylsulfamoyl group, an N-pentylsulfamoyl group, an N-(1-ethylpropyl)sulfamoyl group, an N-(1,1-dimethylpropyl)sulfamoyl group, an N-cyclopentylsulfamoyl group, or an N-hexylsulfamoyl group. and N,N-disubstituted sulfamoyl groups such as an N,N-dimethylsulfamoyl group, an N,N-ethylmethylsulfamoyl group, an N,N-diethylsulfamoyl group, an N,N-propylmethylsulfamoyl group, an N,N-isopropylmethylsulfamoyl group, an N,N-tert-butylmethylsulfamoyl group, an N,N-butylethylsulfamoyl group, an N,N-bis(1-methylpropyl)sulfamoyl group, and an N,N-heptylmethylsulfamoyl group.

[0132] X 2 and X 3Examples of the halogen atom represented by the formula (I) and the halogen atom as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, or a bromine atom is preferred, and a fluorine atom or a chlorine atom is more preferred.

[0133] l is an integer of 0 to 4, preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and even more preferably 1 or 2. n represents 1 or 2, m represents an integer of 0 to 5, and the sum of m and n is an integer of 6 or less.

[0134] X 1 is a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, or -CONR 5 R 6 is preferably a hydrogen atom, an optionally substituted chain alkyl group, or -CONR 5 R 6 and more preferably a hydrogen atom, a chain alkyl group having 1 to 6 carbon atoms which may have a substituent, or -CONR 5 R 6 is. -CONR 5 R 6 R in 5 and R 6 is preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms, and more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0135] X 2 is a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or -OR 1is preferred, more preferably a hydrogen atom, a halogen atom, a hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, or an alkoxy group of 1 to 20 carbon atoms, even more preferably a hydrogen atom, a halogen atom, a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, or an alkoxy group of 1 to 10 carbon atoms, still more preferably a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms which may have a substituent, or an alkoxy group of 1 to 4 carbon atoms, even more preferably an alkyl group of 1 to 4 carbon atoms, a halogen atom, or an alkoxy group of 1 to 4 carbon atoms, even more preferably a halogen atom, or an alkoxy group of 1 to 4 carbon atoms.

[0136] X 3 Examples of the alkyl group include a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, -OR 3 , -CONR 5 R 6 , or -SO2NR 7 R 8 is preferred, and more preferred is a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, or -OR 3 more preferably a halogen atom, a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, or an alkoxy group of 1 to 20 carbon atoms; even more preferably a halogen atom, an alkyl group of 1 to 4 carbon atoms which may have a substituent, or an alkoxy group of 1 to 10 carbon atoms; even more preferably a fluorine atom, a chlorine atom, a bromine atom, an alkyl group of 1 to 4 carbon atoms which has a halogen atom as a substituent, or an alkoxy group of 1 to 4 carbon atoms; even more preferably a fluorine atom, a chlorine atom, a fluoroalkyl group of 1 to 4 carbon atoms (particularly a perfluoroalkyl group), or an alkoxy group of 1 to 4 carbon atoms; and even more preferably a chlorine atom, a trifluoromethyl group, or an alkoxy group of 1 to 4 carbon atoms.

[0137] n is 1 or 2, preferably 1.

[0138] m is an integer of 0 to 5, preferably an integer of 0 to 2, more preferably 0 or 2, and even more preferably 2. If m is 2, then two X 3 may be bonded at any of the ortho, meta, and para positions, preferably at the meta or para position, and more preferably at the para position.

[0139] Examples of Compound (I) include CI Pigment Red 242, 269, the azo pigments described in JP-A-2013-161026, and the azo pigments described in JP-A-2017-142503.

[0140] Compound (I) can be produced by a known method.

[0141] The orange pigment preferably contains compound (II). Compound (II) will be described in detail below, but compound (II) also includes the resonance structure of formula (II), tautomers of formula (II), and compounds obtained by rotating each group in formula (II) around the bond axis of the single bond.

[0142] [ka] [In formula (II), L 1 represents a divalent aromatic hydrocarbon group which may have a substituent. X 11 ~X 14 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.]

[0143] L 1The divalent aromatic hydrocarbon group represented by the formula (I) is a group in which two hydrogen atoms directly bonded to carbon atoms constituting the aromatic hydrocarbon ring are replaced by bonds. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be either a monocyclic or polycyclic ring, and examples thereof include a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, and structures in which at least one hydrogen atom of these aromatic hydrocarbon rings is replaced by a hydrocarbon group. Examples of the hydrocarbon group include the above-mentioned X 2 , X 3 , and R 1 ~R 8 Examples include the same groups as the hydrocarbon group having 1 to 20 carbon atoms represented by the following formula: wherein a hydrocarbon group having 1 to 12 carbon atoms is preferred, more preferably a chain hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a chain hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, and more preferably 0 to 2. The number of carbon atoms in the divalent aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 18, and even more preferably 6 to 12.

[0144] X 11 ~X 14 The hydrocarbon group represented by the formula 2 , X 3 , and R 1 ~R 8 Examples include the same hydrocarbon groups having 1 to 20 carbon atoms as those represented by the following formula:

[0145] L 1 and a divalent aromatic hydrocarbon group represented by X 11 ~X 14 The substituents that the hydrocarbon group represented by the formula (I) may have include the above-mentioned X 1 Aromatic hydrocarbon groups and heterocyclic groups represented by the formula: X 2 and hydrocarbon groups represented by X 3 Examples of the substituents include the same groups as those which may be contained in the hydrocarbon group represented by the following formula:

[0146] L 1is preferably a divalent aromatic hydrocarbon group of 6 to 30 carbon atoms which may have a substituent, more preferably a divalent aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a benzene ring, a biphenyl ring, a naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group of 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms), more preferably a benzene ring, a biphenyl ring, or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group of 1 to 4 carbon atoms, and even more preferably a benzene ring or a biphenyl ring. The substituent that the divalent aromatic hydrocarbon group may have is preferably a halogen atom, an alkoxy group, an alkylsulfanyl group, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, or a substituted or unsubstituted carbamoyl group, more preferably a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, or a substituted or unsubstituted carbamoyl group, even more preferably a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group, still more preferably a chlorine atom, a fluorine atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group, and even more preferably a chlorine atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group.

[0147] L 1 is preferably any of the groups represented by the following formulas (ph1) to (ph16), more preferably any of the groups represented by the formulas (ph1) to (ph3) and (ph11) to (ph13), and even more preferably any of the groups represented by the formulas (ph11), (ph12), (ph11), and (ph12).

[0148] [ka] [In formulas (ph1) to (ph16), * and ** represent bonds.]

[0149] X 11 , X 13 are preferably, independently of one another, a hydrogen atom, an alkyl group of 1 to 10 carbon atoms which may have a substituent, a cycloalkyl group of 3 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 12 carbon atoms which may have a substituent, more preferably an alkyl group of 1 to 10 carbon atoms which may have a substituent, a cycloalkyl group of 3 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 12 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 12 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 to 4 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 10 carbon atoms which may have a substituent, even more preferably an aromatic hydrocarbon group of 6 to 10 carbon atoms which may have a substituent, even more preferably an aromatic hydrocarbon group of 6 to 10 carbon atoms which may have a substituent, even more preferably a phenyl group which may have a substituent, and even more preferably a phenyl group. 11 , X 13 The substituent that the hydrocarbon group represented by the formula (I) may have is preferably a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, or a substituted or unsubstituted carbamoyl group, more preferably a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group, still more preferably a chlorine atom, a fluorine atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group, and still more preferably a chlorine atom or a fluorine atom.

[0150] X 12 , X 14are preferably, independently of one another, a hydrogen atom, an alkyl group of 1 to 10 carbon atoms which may have a substituent, a cycloalkyl group of 3 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 12 carbon atoms which may have a substituent, more preferably an alkyl group of 1 to 10 carbon atoms which may have a substituent, a cycloalkyl group of 3 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 12 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 12 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 to 4 carbon atoms which may have a substituent, or an aromatic hydrocarbon group of 6 to 10 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 to 4 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 to 4 carbon atoms which may have a substituent, even more preferably an alkyl group of 1 or 2 carbon atoms which may have a substituent, even more preferably a methyl group or an ethyl group, and particularly preferably a methyl group. 12 , X 14 The substituent that the hydrocarbon group represented by the formula (I) may have is preferably a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, or a substituted or unsubstituted carbamoyl group, more preferably a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group, still more preferably a chlorine atom, a fluorine atom, an alkoxy group having 1 to 4 carbon atoms, or a cyano group, and still more preferably a chlorine atom or a fluorine atom.

[0151] Examples of compound (II) include CI Pigment Orange 13 and azo pigments described in WO 2022 / 065357.

[0152] Compound (II) can be produced by a known method.

[0153] The colorant (A) may contain a colorant other than those described above, and the other colorant (a1) may be either a dye (hereinafter, sometimes referred to as dye (a1-1)) or a pigment (hereinafter, sometimes referred to as pigment (a1-2)).

[0154] The dye (a1-1) 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 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.

[0155] Specific examples of the dye (a1-1) 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, 57, 66, 73, 76, 80, 88, 97, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 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. As for these dyes (a1-1), one dye or a plurality of dyes may be used for each color, and dyes of each color may be combined.

[0156] Examples of the pigment (a1-2) include pigments listed in the Color Index (The Society of Dyers and Examples include pigments classified as pigments in the Colourists publication.

[0157] 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, 194, 214, 231, 235, 236; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 16; Purple pigments such as CI Pigment Violet 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 (a1-2) may be used singly or in combination for each color.

[0158] CI Pigment Yellow 185, xanthene dyes, and at least one pigment selected from the group consisting of red pigments and orange pigments may be optionally subjected to rosin treatment, surface treatment using a pigment derivative having an acidic or basic group introduced therein, grafting treatment onto the pigment surface using a polymer compound, atomization treatment using sulfuric acid atomization, washing treatment using an organic solvent or water to remove impurities, or 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 a mixture of two or more.

[0159] 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).

[0160] 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.

[0161] The content of CI Pigment Yellow 185 is preferably 6% by mass or more and 50% by mass or less, more preferably 9% by mass or more and 45% by mass or less, even more preferably 11% by mass or more and 40% by mass or less, and even more preferably 14% by mass or more and 35% by mass or less, based on the total amount of colorants.

[0162] The content of CI Pigment Yellow 185 is preferably 1% by mass or more and 30% by mass or less, more preferably 2% by mass or more and 28% by mass or less, even more preferably 3% by mass or more and 26% by mass or less, and even more preferably 5% by mass or more and 24% by mass or less, relative to the total amount of solids in the colored curable resin composition.

[0163] The content of the xanthene dye is preferably 1 to 40% by mass, more preferably 5 to 20% by mass, and even more preferably 7 to 15% by mass, based on the total amount of colorant (A). By adjusting the content of the xanthene dye within the above range, crosstalk (red light leakage) in the resulting color filter can be further reduced. Furthermore, from the viewpoint of further reducing the mixing of red light into the green region in the resulting color filter, it is also preferable that the content of the xanthene dye (preferably the compound represented by formula (1)) is more than 5% by mass based on the total amount of the colorant.

[0164] The content of the xanthene dye is preferably 0.5 to 20 mass %, more preferably 1 to 18 mass %, and even more preferably 2 to 16 mass %, relative to the total amount of solids in the colored curable resin composition.

[0165] The content of the red pigment is preferably 10% by mass or more and 65% by mass or less, more preferably 15% by mass or more and 63% by mass or less, even more preferably 20% by mass or more and 61% by mass or less, and even more preferably 25% by mass or more and 59% by mass or less, based on the total amount of the colorant.

[0166] The content of the red pigment is preferably 5% by mass or more and 40% by mass or less, more preferably 10% by mass or more and 35% by mass or less, and even more preferably 15% by mass or more and 34% by mass or less, relative to the total amount of solids in the colored curable resin composition.

[0167] The content of the compound represented by formula (i) is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more, relative to 100% by mass of the red pigment. The content of the compound represented by formula (i) may be 100% by mass relative to 100% by mass of the red pigment.

[0168] The content of the orange pigment is preferably 0% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 35% by mass or less, and even more preferably 3% by mass or more and 30% by mass or less, based on the total amount of the colorant.

[0169] The content of the orange pigment is preferably 0% by mass or more and 30% by mass or less, more preferably 0.5% by mass or more and 25% by mass or less, and even more preferably 1% by mass or more and 20% by mass or less, relative to the total amount of solids in the colored curable resin composition.

[0170] The content of the compound represented by formula (II) is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more, relative to 100% by mass of the orange pigment. The content of the compound represented by formula (II) may be 100% by mass relative to 100% by mass of the orange pigment.

[0171] The total content of CI Pigment Yellow 185, xanthene colorant, red pigment, and orange pigment is preferably 70% by mass or more, more preferably 83% by mass or more, and even more preferably 90% by mass or more, based on the total amount of colorants.

[0172] The total content of the colorant (A) (preferably CI Pigment Yellow 185, xanthene colorant, red pigment, and orange pigment) is, for example, 10 to 75 mass%, preferably 20 to 70 mass%, and more preferably 30 to 65 mass%, relative to the total amount of solids in the colored curable resin composition. 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.

[0173] <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).

[0174] 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.

[0175] (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.

[0176] 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)").

[0177] 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.

[0178] 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.

[0179] 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).

[0180] [ka]

[0181] [In formula (BI) and formula (BII), R e and R f represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X e and X fis a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0182] 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.

[0183] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X e and X f Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0184] 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.

[0185] [ka]

[0186] 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.

[0187] [ka]

[0188] 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.

[0189] 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.

[0190] 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.

[0191] 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.

[0192] 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.

[0193] 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.

[0194] 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.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] 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.

[0199] 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.

[0200] 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.

[0201] 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, t-butylperoxy-2-ethylhexanoate, etc.). Solvents that dissolve the respective monomers can be used, and examples of the solvent (E) for the colored curable resin composition of the present invention include the solvents described below.

[0202] 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.

[0203] 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.

[0204] 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.

[0205] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0206] 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].

[0207] 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].

[0208] 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].

[0209] 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.

[0210] 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].

[0211] 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.

[0212] 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'].

[0213] 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).

[0214] 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].

[0215] 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.

[0216] Resin [K5] is obtained as a 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:

[0217] 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.

[0218] 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:

[0219] 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].

[0220] 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.

[0221] 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:

[0222] 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).

[0223] 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)).

[0224] 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].

[0225] 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].

[0226] 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.

[0227] 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.

[0228] The content of resin (B) is preferably 5 to 60 mass %, more preferably 10 to 55 mass %, and even more preferably 14 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.

[0229] <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.

[0230] 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., tripentaerythritol octa(meth)acrylate), and the like. (meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethylene glycol modified pentaerythritol tetra(meth)acrylate), acrylate, propylene glycol modified pentaerythritol tri(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate), alkylene glycol modified dipentaerythritol poly(meth)acrylate (e.g., ethylene glycol modified dipentaerythritol penta(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified dipentaerythritol penta(meth)acrylate, propylene glycol modified caprolactone-modified dipentaerythritol hexa(meth)acrylate), caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate). Among these, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol poly(meth)acrylate, alkylene glycol-modified pentaerythritol poly(meth)acrylate, alkylene glycol-modified dipentaerythritol poly(meth)acrylate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, and propylene glycol-modified dipentaerythritol hexa(meth)acrylate is preferred, and ethylene glycol-modified pentaerythritol poly(meth)acrylate and ethylene glycol-modified dipentaerythritol poly(meth)acrylate are more preferred.

[0231] The hydroxyl value of the ethylene glycol modified pentaerythritol poly(meth)acrylate and ethylene glycol modified dipentaerythritol poly(meth)acrylate is, for example, 1 to 50 mg-KOH / g, preferably 1 to 30 mg-KOH / g, and more preferably 1 to 20 mg-KOH / g.

[0232] The number of ethylene glycol units in the ethylene glycol-modified pentaerythritol poly(meth)acrylate and ethylene glycol-modified dipentaerythritol poly(meth)acrylate is, for example, 6 to 30, preferably 8 to 25, and more preferably 10 to 20.

[0233] 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.

[0234] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used.

[0235] Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0236] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): Hereinafter, * represents a bond.

[0237] [ka]

[0238] 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.

[0239] 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.

[0240] [ka]

[0241] 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.

[0242] 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).

[0243] 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.

[0244] 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.

[0245] 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).

[0246] 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.

[0247] 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.

[0248] 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.

[0249] 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.

[0250] <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.

[0251] 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.

[0252] 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.

[0253] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0254] 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.

[0255] 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.

[0256] <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.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0262] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0263] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0264] Among the above solvents, from the viewpoints of coatability and drying property, organic solvents having a boiling point at 1 atm of 120° C. or more and 180° C. or less are preferred. 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.

[0265] 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.

[0266] The content of the solvent (E) is preferably 70 to 95 mass%, more preferably 73 to 92 mass%, and even more preferably 76 to 89 mass%, relative to the total amount of the colored curable resin composition. In other words, the solids content of the colored curable resin composition is preferably 5 to 30 mass%, more preferably 8 to 27 mass%, and even more preferably 11 to 24 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.

[0267] <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.

[0268] 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).

[0269] 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.).

[0270] 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).

[0271] 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.

[0272] <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.

[0273] <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.

[0274] 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.

[0275] 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.

[0276] [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.

[0277] 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 0.5 μm or less, and preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] 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.

[0282] 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.

[0283] In the color filter of the present invention, in a transmission spectrum with wavelength on the horizontal axis and transmittance on the vertical axis, it is also preferable that the slope calculated from the following formula based on the minimum wavelength λ1 that satisfies a transmittance of 70% or more in the wavelength range of 580 nm or more and the transmittance T1 at this wavelength λ1, and the maximum wavelength λ2 that satisfies a transmittance of 30% or less in the wavelength range of less than 580 nm and the transmittance T2 at this wavelength λ2 is 0.03 to 0.06. Slope = (T1-T2) / (λ1-λ2)

[0284] The colored patterns and colored coating films thus obtained are useful as color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. [Example]

[0285] 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."

[0286] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).

[0287] 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.

[0288] <Synthesis Example of Compound (I-1)> According to the description of WO 2022 / 065357, an orange pigment compound (I-1) represented by the following formula was synthesized.

[0289] [ka]

[0290] <Synthesis example of compound (X)> 40.5 parts of the compound represented by formula (IX) and 60.5 parts of 2,6-xylidine (Tokyo Chemical Industry Co., Ltd.) were mixed under light-shielded conditions, and the mixture was 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 (X) (compound (X)). The yield was 85%.

[0291] [ka]

[0292] Identification of the compound represented by formula (X) (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 575 Exact Mass: 574

[0293] <Synthesis example of resin (B-1)> A suitable amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 256 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C with stirring. 2,6 A mixed solution of 44 parts of a mixture of decane-8 and -9-yl acrylate, 57 parts of acrylic acid, 249 parts of 3-phenoxybenzyl acrylate, and 159 parts of propylene glycol monomethyl ether acetate was added dropwise over 3 hours. Meanwhile, a mixed solution of 25 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 210 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the completion of the dropwise addition, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a Brookfield viscosity (23°C) of 51 mPa·s and a solids content of 36.0%. The weight-average molecular weight Mw of the resulting resin (B-1) was 1.1×10 4The resin (B-1) had the following structural units: a polydispersity of 1.98, and an acid value calculated as solid content of 123 mg-KOH / g.

[0294] [ka]

[0295] <Synthesis example of resin (B-2)> 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 (content ratio 1:1 by molar ratio), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 40 parts of 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 to obtain a copolymer (resin (B-2)) solution with a viscosity of 127 mPa·s measured with a Brookfield viscometer (23°C) and a solids content of 37.0 wt%. The weight-average molecular weight Mw of the resulting copolymer was 9.4 × 10 3 The resin (B-2) had the following structural units: a polydispersity of 1.89, and an acid value calculated as solid content of 114 mg-KOH / g.

[0296] [ka]

[0297] <Preparation of Colorant Dispersions (A-1) to (A-11)> The components were mixed in the blending ratios shown in Table 1 and dispersed in a bead mill to obtain colorant dispersions (A-1) to (A-11).

[0298] [Table 1]

[0299] Preparation of Colored Curable Resin Composition <Examples 1 to 9 and Comparative Example 1> The components were mixed in the blending ratios shown in Table 2 to obtain colored curable resin compositions.

[0300] [Table 2]

[0301] <Polymerizable compound (C)> Polymerizable compound (C): A compound represented by the following formula (NK Ester A-DPH-12E: manufactured by Shin-Nakamura Chemical Co., Ltd.) [ka]

[0302] <Polymerization initiator (D)> Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine ("PBG-327 (O-acyloxime compound)" manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) <Leveling Agent (E)> Leveling agent (E): Polyether-modified silicone oil ("Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.) <Solvent (F)> Solvent (F): Propylene glycol monomethyl ether acetate

[0303] <Preparation of colored patterns> A colored curable resin composition was applied to the surface of a 4-inch silicon 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 500 J / m using an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation).2 ~3000J / m 2 The film was irradiated with light at an exposure dose of 0.8 μm, 1.0 μm, and 2.0 μm square (365 nm standard). During the light irradiation, a photomask (with pitches of 1.6 μm, 2.0 μm, and 4.0 μm, respectively) was used to form dot patterns. The colored composition layer after 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 obtain a colored pattern after post-baking.

[0304] <Film thickness measurement> The film thickness of the resulting colored pattern was measured using a film thickness measuring device (DEKTAK3, manufactured by Nippon Shinku Gijutsu Co., Ltd.).

[0305] <Transmittance evaluation> The resulting colored pattern was measured for transmittance in the wavelength range of 380 nm to 780 nm in 1 nm increments using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). The lower the transmittance at 430 nm, the less blue light leaks, and the lower the transmittance at 530 nm, the less green light leaks, indicating excellent color performance as a color filter (especially a red color filter). The results are shown in Table 3.

[0306] [Table 3]

[0307] Furthermore, when the slope of the obtained colored patterns was calculated based on the following formula, it was within the range of 0.03 to 0.06 in all of Examples 1 to 9. Slope = (T1-T2) / (λ1-λ2) λ1: The minimum wavelength that satisfies a transmittance of 70% or more in the wavelength range of 580 nm or more λ2: Maximum wavelength that satisfies a transmittance of 30% or less in the wavelength range of less than 580 nm T1: Transmittance at λ1 T2: Transmittance at λ2

Claims

1. Contains a colorant, a resin, a polymerizable compound, and a polymerization initiator, A colored curable resin composition, wherein the colorant comprises C.I. Pigment Yellow 185, a xanthene dye, and at least one pigment selected from the group consisting of a red pigment and an orange pigment.

2. 2. The colored curable resin composition according to claim 1, wherein the content of the xanthene colorant is from 1% by mass to 40% by mass based on the total amount of the colorants.

3. 3. The colored curable resin composition according to claim 1, wherein a total content of at least one pigment selected from the group consisting of a red pigment and an orange pigment is 10% by mass or more and 65% by mass or less, based on the total amount of colorants.

4. 3. The colored curable resin composition according to claim 1, wherein the content of C. I. Pigment Yellow 185 is 6% by mass or more and 50% by mass or less, based on the total amount of the colorants.

5. 3. The colored curable resin composition according to claim 1, wherein the red pigment and the orange pigment comprise pigments having one or more skeletons selected from the group consisting of a diketopyrrolopyrrole skeleton and an azo skeleton.

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

7. 7. The color filter according to claim 6, wherein in a transmission spectrum with wavelength on the horizontal axis and transmittance on the vertical axis, the slope calculated from the following formula based on a minimum wavelength λ1 that satisfies a transmittance of 70% or more in a wavelength range of 580 nm or more, a transmittance T1 at this wavelength λ1, a maximum wavelength λ2 that satisfies a transmittance of 30% or less in a wavelength range of less than 580 nm, and a transmittance T2 at this wavelength λ2 is 0.03 to 0.06: Slope = (T1-T2) / (λ1-λ2)

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

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

Images