Color-curable resin composition, color filter, display device, and solid-state image sensor

Abstract

The object of this invention is to provide a color-curable resin composition that can reduce crosstalk in color filters. [Solution] The present invention relates to a colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant comprises a first pigment composed of at least one selected from an orange pigment and a red pigment, and a yellow pigment, the first pigment comprises a diketopyrrolopyrrole pigment and an azo pigment, and the yellow pigment comprises CI Pigment Yellow 180.

Description

[Technical Field]

[0001] The present invention relates to a color-curable resin composition, a color filter formed from the color-curable resin composition, a display device including the color filter, and a solid-state image sensor including the color filter. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as in solid-state image sensors such as CCDs 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 Publication No. 2023-39409 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] When using color filters with sensors such as solid-state image sensors, increasing resolution necessitates miniaturizing pixels. However, this leads to a problem where light transmitted through a given color filter leaks into the filter regions of other colors (e.g., crosstalk), preventing improvements in pixel quantum efficiency. Therefore, the object of the present invention is to provide a color-curable resin composition that can reduce crosstalk of color filters. [Means for solving the problem]

[0005] That is, the gist of the present invention is as follows. [1] A colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant includes a first pigment composed of at least one selected from an orange pigment and a red pigment, and a yellow pigment, the first pigment includes a diketopyrrolopyrrole-based pigment and an azo-based pigment, the yellow pigment includes C.I. Pigment Yellow 180, and a colored curable resin composition. [2] The colored curable resin composition according to [1], wherein the content of the first pigment is 60 to 95% by mass in a total of 100% by mass of the first pigment and the yellow pigment. [3] The colored curable resin composition according to [1] or [2], wherein the azo-based pigment of the red pigment is a compound represented by the formula (I).

Chemical formula

[0006] According to the present invention, it is possible to reduce crosstalk in color filters. Specifically, it is possible to eliminate green light leakage and reduce crosstalk to the green pixel region. According to a preferred embodiment of the present invention, it is possible to eliminate green light leakage and reduce crosstalk to the green pixel region, as well as eliminate blue light leakage and reduce crosstalk to the blue pixel region. [Modes for carrying out the invention]

[0007] [Colored curable resin composition] The present invention comprises a coloring agent (hereinafter sometimes referred to as coloring agent (A)), a resin (hereinafter sometimes referred to as resin (B)), a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), wherein the coloring agent (A) comprises a first pigment consisting of at least one selected from an orange pigment and a red pigment, and a yellow pigment, the first pigment comprises a diketopyrrolopyrrole pigment and an azo pigment, and the yellow pigment comprises CI Pigment Yellow 180, and includes a colorable curable resin composition. By using such a color-curable resin composition, a color filter with reduced crosstalk can be fabricated. Specifically, it is possible to eliminate green light leakage and reduce crosstalk to the green pixel region. In a preferred embodiment, there is no green light leakage, reducing crosstalk to the green pixel region, and there is no blue light leakage, reducing crosstalk to the blue pixel region. The color-curable resin composition of the present invention may contain a solvent (hereinafter sometimes referred to as solvent (E)). The colored curable resin composition of the present invention may contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In this specification, the compounds exemplified as components may be used individually or in combination, unless otherwise specified.

[0008] In this invention, red pigments are defined as having a maximum absorption wavelength greater than 500 nm, orange pigments as having a maximum absorption wavelength greater than 460 nm and less than or equal to 500 nm, and yellow pigments as having a maximum absorption wavelength greater than 410 nm and less than or equal to 460 nm, based on the following conditions. [Conditions] A composition is prepared containing only one type of coloring agent, with the coloring agent content being 10% by mass of the solid content of the colored curable resin composition. The absorbance in the visible light region (wavelength 400-780 nm) is measured for a color filter with a film thickness of 1 μm formed from this composition.

[0009] The coloring agent includes a first pigment consisting of at least one selected from an orange pigment and a red pigment, and the first pigment includes a diketopyrrolopyrrole pigment and an azo pigment. The first pigment preferably contains at least a red pigment, and more preferably contains a red pigment and an orange pigment. The red pigment preferably contains azo pigments and diketopyrrolopyrrole pigments, and more preferably contains diketopyrrolopyrrole pigments. From the viewpoint of reducing transmittance at 530 nm, it is preferable that the orange pigment includes an azo pigment.

[0010] The aforementioned diketopyrrolopyrrole pigment is preferably a compound represented by formula (z).

[0011] [ka] [In formula (z), R 1 ~R 10 These are, independently, a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group with 1 to 15 carbon atoms, and -OR 11 , -SR 11 -SO3M, -SO2NHR 11 , -SO2N(R 12 )2, or -N(R 11 ) represents 2. R 11 This represents a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms. R 12 This represents a hydrocarbon group with 1 to 15 carbon atoms. M represents a hydrogen atom or an alkali metal atom.

[0012] The halogen atoms are preferably fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, more preferably fluorine atoms, chlorine atoms, and bromine atoms, and even more preferably chlorine atoms and bromine atoms.

[0013] R 1 ~R 10The hydrocarbon group having 1 to 15 carbon atoms represented by may be saturated or unsaturated, and is preferably an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and is also preferably a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group.

[0014] The aliphatic hydrocarbon group is preferably a linear or branched alkyl group. Specifically, examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, octadecyl group, 1,5-dimethylhexyl group, 1,6-dimethylheptyl group, and 2-ethylhexyl group. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 8, even more preferably 1 to 6, and particularly preferably 1 to 3.

[0015] The aromatic hydrocarbon group is preferably an alkylphenyl group such as a phenyl group, tolyl group, xylyl group, mesityl group, propylphenyl group, or butylphenyl group, and more preferably a phenyl group. The number of carbon atoms in the aromatic hydrocarbon group, including the number of carbon atoms in the substituents, is preferably 6 to 15, more preferably 6 to 12, and even more preferably 6 to 9. The aromatic hydrocarbon group may be substituted, and may have substituents such as a trifluoromethyl group, halogen atom, nitro group, cyano group, carbamoyl group, sulfamoyl group, or alkoxyl group having 1 to 4 carbon atoms. Preferably, the substituted aromatic hydrocarbon group is 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.

[0016] The combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group is preferably an aralkyl group such as a benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, or 2,4-dichlorobenzyl group.

[0017] R 11 and R 12 A hydrocarbon group with 1 to 15 carbon atoms represented by R 1 ~R 10 This may be the same as a hydrocarbon group having 1 to 15 carbon atoms represented by , and the preferred range may also be the same.

[0018] -OR 11 Examples include methoxy groups, ethoxy groups, propoxy groups, butoxy groups, pentyloxy groups, hexyloxy groups, heptyloxy groups, octyloxy groups, 2-ethylhexyloxy groups, and eicosyloxy groups.

[0019] -SR 11 Examples include methylsulfanyl group, ethylsulfanyl group, butylsulfanyl group, hexylsulfanyl group, decylsulfanyl group, and eicosylsulfanyl group.

[0020] -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 Examples include N-1 substituted sulfamoyl groups such as N-(3-methylbutyl)sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-(1,3-dimethylbutyl)sulfamoyl group, N-(3,3-dimethylbutyl)sulfamoyl group, N-heptylsulfamoyl group, N-(1-methylhexyl)sulfamoyl group, N-(1,4-dimethylpentyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group, N-(1,5-dimethyl)hexylsulfamoyl group, and N-(1,1,2,2-tetramethylbutyl)sulfamoyl group.

[0021] -SO2N(R 12 Examples of )2 include N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, N,N-heptylmethylsulfamoyl group, and other N,N-2 substituted sulfamoyl groups; and so on.

[0022] -N(R 11 )2 is, amino group; Monosubstituted amino groups such as N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-(sec-butyl)amino group, N-(tert-butyl)amino group, N-pentylamino group, N-(1-ethylpropyl)amino group, N-hexylamino group, N-(2-ethylhexyl)amino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-phenylamino group, etc.

[0023] 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 Examples of disubstituted amino groups include amino groups, N,N-dipentylamino groups, N,N-bis(1-ethylpropyl)amino groups, N-butyl-N-hexylamino groups, N-hexyl-N-methylamino groups, N,N-dihexylamino groups, N-(2-ethylhexyl)-N-methylamino groups, N,N-bis(2-ethylhexyl)amino groups, N,N-diheptylamino groups, N-octyl-N-methylamino groups, N,N-dioctylamino groups, N-phenyl-N-methylamino groups, N,N-diphenylamino groups, and other such groups.

[0024] The alkali metal atom represented by M in -SO3M above is preferably sodium or potassium.

[0025] Among them, R 1 ~R 10 Each of these elements independently preferably represents a hydrogen atom, a halogen atom, a cyano group, or a hydrocarbon group having 1 to 15 carbon atoms, and more preferably a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 10 carbon atoms.

[0026] In a preferred embodiment, R 1 ~R 5 At least one of them is a halogen atom or a hydrocarbon group having 1 to 15 carbon atoms, and R 6 ~R 10 At least one of them is preferably a halogen atom or a hydrocarbon group having 1 to 15 carbon atoms, R 1 ~R 5 At least one of them is a halogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and R 6 ~R 10 At least one of them is more preferably a halogen atom or a hydrocarbon group having 1 to 10 carbon atoms, R 1 ~R 5 At least one of them is a halogen atom or an aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 10 carbon atoms, and R 6 ~R 10 It is even more preferable that at least one of these is a halogen atom or an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group. If there are multiple 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 very different.

[0027] The compound represented by formula (z) is more preferably the compound represented by formula (z-1).

[0028] [ka] [In formula (z-1), R 3 and R 8 These are, independently, a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group with 1 to 15 carbon atoms, and -OR 11 , -SR 11 -SO3M, -SO2NHR 11 , -SO2N(R 12 )2, or -N(R 11 ) represents 2. R 11 This represents a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms. R 12This represents a hydrocarbon group with 1 to 15 carbon atoms. M represents a hydrogen atom or an alkali metal atom.

[0029] R 3 , R 8 , R 11 , R 12 M is the same as above.

[0030] In equation (z) or equation (z-1), R 3 and R 8 Each of these groups is preferably an atom of halogen or a hydrocarbon group having 1 to 15 carbon atoms, more preferably an atom of halogen or an aliphatic hydrocarbon group or 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. If there are multiple atoms of halogen or hydrocarbon groups, the atoms of halogen or hydrocarbon groups may be the same or different.

[0031] The compound represented by formula (z) or formula (z-1) is preferably CI pigment red 254, CI pigment red 264, CI pigment red 272, CI pigment red 291, etc.

[0032] The azo pigment for the red pigment is preferably a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)). Compound (I) includes resonance structures of formula (I), tautomers of formula (I), and compounds obtained by rotating each group in formula (I) around the bond axis of a single bond.

[0033] [ka] [In formula (I), X 1 This is 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 It represents. X 2 This includes a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, and -OR 1 , or -COOR 2 It represents. X 3 This includes halogen atoms, cyano groups, nitro groups, hydrocarbon groups having 1 to 20 carbon atoms which may have substituents, and -OR 3 ,-COOR 4 ,-CONR 5 R 6 , or -SO2NR 7 R 8 Represents . R 1 ~R 8 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. l represents an integer between 0 and 4. n represents either 1 or 2. m represents an integer between 0 and 5. The sum of m and n is an integer less than or equal to 6. X 1 , X 2 , or X 3 If multiple instances exist, they may be identical or different.

[0034] X 1 The aliphatic hydrocarbon group represented by may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0035] Examples of saturated or unsaturated linear hydrocarbon groups include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups; Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethylpropyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, 2-propylpentyl group, 1-ethyl-1,2-dimethylpropyl group, 1-methylpentyl group, 4-methylpentyl group, 4-methylpentyl group Branched alkyl groups such as hexyl group, 5-methylhexyl group, 2-ethylhexyl group, 1-methylhexyl group, 1-ethylpentyl group, 1-propylbutyl group, 3-ethylheptyl group, 2,2-dimethylheptyl group, 1-methylheptyl group, 1-ethylhexyl group, 1-propylpentyl group, 1-methyloctyl group, 1-ethylheptyl group, 1-propylhexyl group, 1-butylpentyl group, 1-methylnonyl group, 1-ethyloctyl group, 1-propylheptyl group, and 1-butylhexyl group; 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 -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, dodecenyl group, etc. Alkynyl groups such as ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), octinyl group (e.g., 1-octinyl group, 7-octinyl group), butynyl group, pentynyl group, hexynyl group, heptynyl group, noninyl group, desinyl group, undecynyl group, dodecynyl group, etc. These are some examples. The number of carbon atoms in the saturated or unsaturated linear hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 12, and particularly preferably 1 to 9. Among these, a linear or branched alkyl group having 1 to 9 carbon atoms is particularly preferred.

[0036] Examples of saturated or unsaturated alicyclic hydrocarbon groups include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, and 3,4-dimethylcyclohexyl group. Examples include cycloalkyl groups such as methylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, and 4,4-dimethylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexa-1-en-1-yl, cyclohexa-2-en-1-yl, cyclohexa-3-en-1-yl), cycloheptenyl, and cyclooctenyl; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norborneyl, adamantyl, and bicyclo[2.2.2]octyl; and so on.

[0037] The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, even more preferably 3 to 18, and particularly preferably 3 to 12.

[0038] X1 Examples of the aromatic hydrocarbon group represented by [X] include aryl groups such as phenyl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, biphenyl group; alkylaryl groups such as o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2-methyl-6-isopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group; alkenylaryl groups such as 4-vinylphenyl group; and the like.

[0039] X 1 The number of carbon atoms of the aromatic hydrocarbon group represented by [X] is preferably 6 to 20, more preferably 6 to 18, still more preferably 6 to 12, and even more preferably 6 to 10.

[0040] X 1 The heterocyclic group represented by [X] may be monocyclic or polycyclic, and may be a saturated ring or an unsaturated ring. X 1 As the heterocyclic group represented by [X], a heterocyclic group containing a heteroatom other than a carbon atom as a ring constituent element is preferable. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0041] X 1 The number of carbon atoms of the heterocyclic group represented by [X] is preferably 2 to 20, more preferably 3 to 18, and still more preferably 3 to 15.

[0042] Examples of the heterocyclic group containing only nitrogen atoms as heteroatoms include monocyclic heterocyclic groups such as pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group; polycyclic heterocyclic groups such as indolizinyl group, indolyl group, 1H-indazolyl group, isoquinolyl group, quinolyl group, phthalazinyl group, carbazolyl group, acridinyl group, indolinyl group, isoindolinyl group; and the like. Examples of the heterocyclic group containing only oxygen atoms as heteroatoms include monocyclic heterocyclic groups such as furyl group, pyranyl group; polycyclic heterocyclic groups such as isobenzofuranyl group, chromenyl group, xanthenyl group, chromanyl group; and the like. Examples of the heterocyclic group containing only sulfur atoms as heteroatoms include monocyclic heterocyclic groups such as thienyl group; polycyclic heterocyclic groups such as benzo[b]thienyl group, thianthrenyl group; and the like. Examples of the heterocyclic group containing nitrogen atoms and oxygen atoms as heteroatoms include monocyclic heterocyclic groups such as oxazolyl group; polycyclic heterocyclic groups such as benzimidazolonyl group; and the like.

[0043] X 1 Among the heterocyclic groups represented by, polycyclic heterocyclic groups are preferred, and polycyclic heterocyclic groups having a benzene ring such as benzo[b]thienyl group, thianthrenyl group, isobenzofuranyl group, chromenyl group, xanthenyl group, indolyl group, 1H-indazolyl group, isoquinolyl group, quinolyl group, phthalazinyl group, carbazolyl group, acridinyl group, chromanyl group, indolinyl group, isoindolinyl group, benzimidazolonyl group are more preferred.

[0044] X 1 -CONR represented by 5 R 6Examples include carbamoyl groups; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-phenylcarbamoyl group, and other N-1 substituted carbamoyl groups; N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, etc. Examples include N,N-2 substituted carbamoyl groups such as moyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, and N,N-diphenylcarbamoyl group.

[0045] X 2 , X 3 , and R 1 ~R 8 Examples of hydrocarbon groups represented by include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0046] Saturated or unsaturated linear hydrocarbon groups include linear alkyl groups such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group; isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, ( Examples include branched alkyl groups such as 1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, and (2-ethyl)octyl group; and alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, and 2-pentenyl group.

[0047] 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., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl, and cyclooctenyl; and norbornyl, adamantyl, and bicyclo[2.2.2]octyl groups.

[0048] As for aromatic hydrocarbon groups, the above-mentioned X 1 Examples of groups similar to the aromatic hydrocarbon group represented by the symbol are shown.

[0049] The aforementioned hydrocarbon groups having 1 to 20 carbon atoms may be groups that combine two or more selected from the group consisting of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 20. Such groups include, for example, aralkyl groups such as benzyl group, phenethyl group, and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, and 3,4-dimethylcyclohexyl group. Examples include alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded, such as 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, and 3,3,5,5-tetramethylcyclohexyl group; alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, and cyclohexylethyl group; and so on.

[0050] X 1 Aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group represented by X 2 A hydrocarbon group represented by X 3The substituents that the hydrocarbon group represented by may have include halogen atoms, hydroxyl groups, alkoxy groups, alkylsulfanyl groups, formyl groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, nitro groups, cyano groups, substituted or unsubstituted carbamoyl groups, substituted or unsubstituted sulfamoyl groups, -SO3M, etc. The M represents a hydrogen atom or an alkali metal atom (e.g., sodium, potassium).

[0051] As an aliphatic hydrocarbon group having a halogen atom as a substituent, X 1 Examples include a halogen atom bonded to an aliphatic hydrocarbon group represented by , such as a chain alkyl group including trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-dibromoethyl, 2,2,3,3-tetrafluoropropyl, pentafluoroethyl, and heptafluoropropyl.

[0052] Examples of aromatic hydrocarbon groups having a halogen atom as a substituent include X 1 Examples include aromatic hydrocarbon groups to which halogen atoms are bonded, such as aryl groups like 4-bromophenyl, 2,4-dichlorophenyl, pentafluorophenyl, 2-methyl-4-chlorophenyl, and 4,5,8-trichloro-2-naphthyl.

[0053] Examples of heterocyclic groups having halogen atoms as substituents include X 1 Examples include a heterocyclic group represented by , to which a halogen atom is bonded.

[0054] Examples of combinations of aromatic hydrocarbon groups and aliphatic hydrocarbon groups having halogen atoms as substituents include (2,4-dichlorophenyl)methyl group, (4-fluorophenyl)methyl group, (3,5-difluorophenyl)methyl group, 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl group, (phenoxy)(phenyl)methyl group, and (benzyloxy)(phenyl)methyl group.

[0055] Examples of alkoxy groups used as substituents include methoxy groups, ethoxy groups, propoxy groups, n-butoxy groups, and tert-butoxy groups. The alkoxy group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.

[0056] Examples of alkylsulfanil groups used as substituents include methylsulfanil group, ethylsulfanil group, propylsulfanil group, and n-butylsulfanil group. The alkylsulfanil group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.

[0057] Examples of substituted amino groups as substituents include amino groups having one or two hydrocarbon groups. Examples of the hydrocarbon groups include those exemplified above as hydrocarbon groups having 1 to 20 carbon atoms, and are preferably alkyl groups having 1 to 4 carbon atoms or aromatic hydrocarbon groups having 6 to 10 carbon atoms. Examples of substituted amino groups include N-1 substituted amino groups such as N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, and N-phenylamino group; and N,N-2 substituted amino groups such as N,N-dimethylamino group, N,N-diethylamino group, N,N-dipropylamino group, N,N-diisopropylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, and N,N-ethylphenylamino group.

[0058] The N-acylamino group as a substituent is -NHCOR 9a It means a group represented by R 9a R represents a hydrogen atom or a hydrocarbon group. 9a Examples of hydrocarbon groups represented by include the groups exemplified above as hydrocarbon groups having 1 to 20 carbon atoms. 9a Preferably, the N-acylamino group is 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 N-acylamino groups include N-formylamino group, N-acetylamino group, N-propanoylamino group, N-butanoylamino group, and N-benzoylamino group.

[0059] Substitutive or unsubstituted carbamoyl groups as substituents include -CONR 9b R 9c It means a group represented by R 9b , R 9c Each of these independently represents either a hydrogen atom or a hydrocarbon group. 9b , R 9c Examples of hydrocarbon groups represented by include the groups exemplified above as hydrocarbon groups having 1 to 20 carbon atoms. 9b , R 9c Preferably, these are a hydrogen atom, a C1-C4 alkyl group, or a C6-C10 aromatic hydrocarbon group, independently of each other. -CONR 9b R 9c Examples include carbamoyl groups; N-1 substituted carbamoyl groups such as N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-tert-butylcarbamoyl group, and N-phenylcarbamoyl group; and N,N-2 substituted carbamoyl groups such as N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-phenylmethylcarbamoyl group, and N,N-diphenylcarbamoyl group.

[0060] A substituted or unsubstituted sulfamoyl group as a substituent is -SO2NR 9d R 9e It means a group represented by R 9d , R 9e Each of these independently represents either a hydrogen atom or a hydrocarbon group. 9d , R 9e Examples of hydrocarbon groups represented by include the groups exemplified above as hydrocarbon groups having 1 to 20 carbon atoms. 9d , R 9ePreferably, these are a hydrogen atom, a C1-C4 alkyl group, or a C6-C10 aromatic hydrocarbon group, independently of each other. -SO2NR 9d R 9e Examples include sulfamoyl groups; N-1 substituted sulfamoyl groups such as N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, and N-isobutylsulfamoyl group; and N,N-2 substituted sulfamoyl groups such as N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, and N,N-dibutylsulfamoyl group.

[0061] X 2 -OR 1 , and X 3 -OR 3 Examples include hydroxyl groups; methoxy groups, ethoxy groups, propoxy groups, isopropoxy groups, n-butoxy groups, isobutoxy groups, sec-butoxy groups, tert-butoxy groups, pentyloxy groups, and other alkoxy groups.

[0062] X 2 -COOR 2 , and X 3 -COOR 4 Examples include carboxyl groups; alkoxycarbonyl groups such as methoxycarbonyl groups, ethoxycarbonyl groups, propoxycarbonyl groups, tert-butoxycarbonyl groups, butoxycarbonyl groups, and pentyloxycarbonyl groups; and so on.

[0063] X 3 -CONR 5 R 6Examples include carbamoyl groups; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, and other N-1 substituted carbamoyl groups; N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethyl Examples include N,N-2 substituted carbamoyl groups such as carbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, and N,N-butylmethylcarbamoyl group.

[0064] X 3 -SO2NR 7 R 8 Examples include N-1 substituted sulfa groups such as sulfamoyl groups; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-(1,1-dimethylpropyl)sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, etc. Examples of moyl groups include N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, and N,N-heptylmethylsulfamoyl group, which are N,N-2 substituted sulfamoyl groups.

[0065] X 2 and X 3Examples of halogen atoms represented by and halogen atoms as substituents include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, among which fluorine atoms, chlorine atoms, or bromine atoms are preferred, and fluorine atoms or chlorine atoms are more preferred.

[0066] l is an integer from 0 to 4, preferably an integer from 1 to 4, more preferably an integer from 1 to 3, and even more preferably 1 or 2. n represents either 1 or 2, m represents any integer from 0 to 5, and the sum of m and n is an integer less than or equal to 6.

[0067] X 1 Examples include a hydrogen atom, an aliphatic hydrocarbon group which may have substituents, or -CONR 5 R 6 Preferably, it is a hydrogen atom, a chain alkyl group which may have substituents, or -CONR 5 R 6 More preferably, a hydrogen atom, a C1-C6 chain alkyl group which may have substituents, or -CONR 5 R 6 That is the case. -CONR 5 R 6 In R 5 and R 6 It is preferably a hydrogen atom and a hydrocarbon group having 1 to 15 carbon atoms, and more preferably a hydrogen atom and an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0068] X 2 Examples include hydrogen atoms, halogen atoms, hydrocarbon groups having 1 to 20 carbon atoms which may have substituents, or -OR 1Preferably, it is a hydrogen atom, a halogen atom, a C1-C10 hydrocarbon group which may have substituents, or a C1-C20 alkoxy group, even more preferably a hydrogen atom, a halogen atom, a C1-C10 linear hydrocarbon group which may have substituents, or a C1-C10 alkoxy group, even more preferably a hydrogen atom, a halogen atom, a C1-C4 alkyl group which may have substituents, or a C1-C4 alkoxy group, even more preferably a C1-C4 alkyl group, a halogen atom, or a C1-C4 alkoxy group, and even more preferably a halogen atom and a C1-C4 alkoxy group.

[0069] X 3 Examples include halogen atoms, hydrocarbon groups having 1 to 20 carbon atoms which may have substituents, and -OR 3 ,-CONR 5 R 6 , or -SO2NR 7 R 8 Preferably, it is a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms which may have substituents, or -OR 3 More preferably, a halogen atom, a C1-C10 chain hydrocarbon group which may have substituents, or a C1-C20 alkoxy group; even more preferably, a halogen atom, a C1-C4 alkyl group which may have substituents, or a C1-C10 alkoxy group; even more preferably, a fluorine atom, a chlorine atom, a bromine atom, a C1-C4 alkyl group which has a halogen atom as a substituent, or a C1-C4 alkoxy group; even more preferably, a fluorine atom, a chlorine atom, a C1-C4 fluoroalkyl group (especially a perfluoroalkyl group), or a C1-C4 alkoxy group; and even more preferably, a chlorine atom, a trifluoromethyl group, or a C1-C4 alkoxy group.

[0070] n is 1 or 2, preferably 1.

[0071] m is an integer from 0 to 5, preferably an integer from 0 to 2, more preferably 0 or 2, and even more preferably 2. If m is 2, then the two X 3 The compound may be bonded in an ortho, meta, or para position, but it is preferably bonded in a meta or para position, and more preferably in a para position.

[0072] Furthermore, the compound represented by formula (I) may include one selected from the group consisting of the compound represented by formula (Ia) and the compound represented by formula (Ib), as described later, and it is preferable that it includes the compound represented by formula (Ia) or the compound represented by formula (Ib). Examples of one embodiment of compound (I) include compounds (Ia-1) to (Ia-600) specified by the following formula (Ia) and Tables 1 to 8, and compounds (Ib-1) to (Ib-600) specified by the following formula (Ib) and Tables 9 to 17. In Tables 1 to 17, "t1" to "t14" represent the groups represented by the following formulas (t1) to (t14), respectively, "H" represents a hydrogen atom, "Me" represents a methyl group, "Et" represents an ethyl group, "OMe" represents a methoxy group, "OEt" represents an ethoxy group, "Cl" represents a chlorine atom, "F" represents a fluorine atom, "CF3" represents a trifluoromethyl group, and "-" indicates the absence of the corresponding group.

[0073] [ka] [In formula (Ia), X 2 This has the same meaning as above, X 1a X represents a phenyl group (the phenyl group may have a halogen atom and a group selected from the group consisting of alkyl groups having 1 to 4 carbon atoms that may have a halogen atom), X 3a and X 3a These are, independently of each other, a halogen atom, a C1-C4 alkyl group which may have a halogen atom, or -OR 3X Represents R 3X This represents an alkyl group having 1 to 4 carbon atoms, which may contain a halogen atom.

[0074] [Table 1]

[0075] [Table 2]

[0076] [Table 3]

[0077] [Table 4]

[0078] [Table 5]

[0079] [Table 6]

[0080] [Table 7]

[0081] [Table 8]

[0082] [ka] [In formula (Ib), X 1c and X 1d These terms independently represent the same meaning as above and may have halogen atoms, and are C1-C4 alkyl groups or -CONHX 1b (X 1b is a hydrogen atom or X 1a (represents X) 2c and X2d These are, independently of each other, a halogen atom, a C1-C4 alkyl group which may have a halogen atom, or -OR 3X (R 3X (This represents the same meaning as above), X 3c and X 3d These are, independently of each other, a halogen atom, a C1-C4 alkyl group which may have a halogen atom, or -OR 3X [This represents...]

[0083] [Table 9]

[0084] [Table 10]

[0085] [Table 11]

[0086] [Table 12]

[0087] [Table 13]

[0088] [Table 14]

[0089] [Table 15]

[0090] [Table 16]

[0091] [Table 17]

[0092] [ka] [In equations (t1) to (t14), * represents a bond.]

[0093] Among the compounds (I), compounds (Ia-1) to (Ia-600) and compounds (Ib-505) to (Ib-600) are preferred. Compounds (Ia-1) to (Ia-100), compound (Ib-505) to (Ib-528), and compound (Ib-589) to (Ib-600) are more preferable. Compounds (Ia-51) to (Ia-100), compound (Ib-517) to (Ib-528), and compound (Ib-589) to (Ib-600) are even more preferred. Compounds (Ia-51) to (Ia-75), (Ib-522), (Ib-528), and (Ib-591) are more preferably, Compounds (Ia-51) to (Ia-55), (Ia-61) to (Ia-70), (Ib-522), and (Ib-591) are more preferably, Compounds (Ia-51) to (Ia-55), (Ia-61) to (Ia-66), (Ib-522), and (Ib-591) are more preferably, Compounds (Ia-51) to (Ia-55), (Ia-61), (Ib-522), and (Ib-591) (CI Pigment Red 242) are even more preferred.

[0094] As a method for producing compound (I), known methods (for example, the methods described in Japanese Patent Publication No. 2013-161026 and Japanese Patent Publication No. 2017-142503) can be employed.

[0095] The orange azo pigment is preferably a compound represented by formula (II) (hereinafter sometimes referred to as compound (II)). Compound (II) includes resonance structures of formula (II), tautomers of formula (II), and compounds obtained by rotating each group in formula (II) around the bond axis of a single bond.

[0096] [ka] [In formula (II), L 1 This represents a divalent aromatic hydrocarbon group which may have substituents. X 11 ~X 14 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents.

[0097] L 1 A divalent aromatic hydrocarbon group represented by X is a group in which two hydrogen atoms directly bonded to carbon atoms constituting an aromatic hydrocarbon ring are replaced by a bonding site. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be monocyclic or polycyclic, and examples include a benzene ring, a biphenyl ring, a naphthalene ring, anthracene ring, and structures in which at least one hydrogen atom of these aromatic hydrocarbon rings is replaced by a hydrocarbon group. The hydrocarbon group is as described above. 2 , X 3 , and R 1 ~R 8 Examples of groups similar to the hydrocarbon groups having 1 to 20 carbon atoms represented by can be cited, with hydrocarbon groups having 1 to 12 carbon atoms being preferred, more preferably chain hydrocarbon groups having 1 to 10 carbon atoms, or aromatic hydrocarbon groups having 6 to 12 carbon atoms, even more preferably chain hydrocarbon groups having 1 to 10 carbon atoms, and even more preferably saturated chain hydrocarbon groups having 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, 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.

[0098] X 11 ~X 14 The hydrocarbon group represented by the above X 2 , X 3 , and R 1 ~R 8 Examples of similar groups include hydrocarbon groups with 1 to 20 carbon atoms represented by .

[0099] L 1 A divalent aromatic hydrocarbon group represented by and X 11 ~X 14 The substituents that the hydrocarbon group represented by the above-mentioned X may have include 1 Aromatic hydrocarbon groups and heterocyclic groups represented by X 2 A hydrocarbon group represented by X 3 Examples of substituents that may be present on the hydrocarbon group represented by include similar groups.

[0100] L 1Preferably, the compound is a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have substituents, and more preferably, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have substituents. 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 by a saturated chain hydrocarbon group having 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 by a saturated chain hydrocarbon group having 1 to 4 carbon atoms, and even more preferably a benzene ring or a biphenyl ring. The substituents that the divalent aromatic hydrocarbon group may have are preferably halogen atoms, alkoxy groups, alkylsulfanyl groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, and substituted or unsubstituted carbamoyl groups; more preferably halogen atoms, C1-C4 alkoxy groups, C1-C4 alkylsulfanyl groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, substituted or unsubstituted carbamoyl groups; even more preferably halogen atoms, C1-C4 alkoxy groups, and cyano groups; even more preferably chlorine atoms, fluorine atoms, C1-C4 alkoxy groups, and cyano groups.

[0101] L 1 Preferably, the group is one of the groups represented by formulas (ph1) to (ph16) below, more preferably one of the groups represented by formulas (ph1) to (ph3) and formulas (ph11) to (ph13), and even more preferably one of the groups represented by formulas (ph11) and (ph12).

[0102] [ka] [In equations (ph1) to (ph16), * and ** represent bonding.]

[0103] X 11, X 13 Preferably, these are, independently of each other, a hydrogen atom, an optionally substituted C1-C10 alkyl group, an optionally substituted C3-C10 cycloalkyl group, or an optionally substituted C6-C12 aromatic hydrocarbon group; more preferably, an optionally substituted C1-C10 alkyl group, an optionally substituted C3-C10 cycloalkyl group, or an optionally substituted C6-C12 aromatic hydrocarbon group; even more preferably, an optionally substituted C1-C10 alkyl group, or an optionally substituted C6-C12 aromatic hydrocarbon group; even more preferably, an optionally substituted C1-C4 alkyl group, or an optionally substituted C6-C10 aromatic hydrocarbon group; even more preferably, an optionally substituted C6-C10 aromatic hydrocarbon group; even more preferably, an optionally substituted phenyl group; and even more preferably, a phenyl group. 11 , X 13 The substituents that the hydrocarbon group represented by may have are preferably halogen atoms, C1-C4 alkoxy groups, C1-C4 alkylsulfanyl groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, substituted or unsubstituted carbamoyl groups, more preferably halogen atoms, C1-C4 alkoxy groups, cyano groups, even more preferably chlorine atoms, fluorine atoms, C1-C4 alkoxy groups, cyano groups, and even more preferably chlorine atoms and fluorine atoms.

[0104] X 12 , X 14Preferably, these are, independently of each other, a hydrogen atom, a C1-C10 alkyl group which may have substituents, a C3-C10 cycloalkyl group which may have substituents, or a C6-C12 aromatic hydrocarbon group which may have substituents; more preferably, a C1-C10 alkyl group which may have substituents, a C3-C10 cycloalkyl group which may have substituents, or a C6-C12 aromatic hydrocarbon group which may have substituents; even more preferably, a C1-C10 alkyl group which may have substituents, or a C6-C12 aromatic hydrocarbon group which may have substituents; even more preferably, a C1-C4 alkyl group which may have substituents, or a C6-C10 aromatic hydrocarbon group which may have substituents; even more preferably, a C1-C4 alkyl group which may have substituents; even more preferably, a C1 or C2 alkyl group which may have substituents; even more preferably, a methyl group or an ethyl group; and particularly preferably, a methyl group. 12 , X 14 The substituents that the hydrocarbon group represented by may have are preferably halogen atoms, C1-C4 alkoxy groups, C1-C4 alkylsulfanyl groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, substituted or unsubstituted carbamoyl groups, more preferably halogen atoms, C1-C4 alkoxy groups, cyano groups, even more preferably chlorine atoms, fluorine atoms, C1-C4 alkoxy groups, cyano groups, and even more preferably chlorine atoms and fluorine atoms.

[0105] Examples of compound (II) include CI Pigment Orange 13 and azo pigments described in International Publication No. 2022 / 065357. CI Pigment Orange 13 as compound (II) can reduce transmittance at 430 nm.

[0106] A known method can be used to produce compound (II).

[0107] The coloring agent contains a yellow pigment, which is CI Pigment Yellow 180. The coloring agent preferably further contains a yellow pigment different from CI Pigment Yellow 180. Examples of yellow pigments different from CI Pigment Yellow 180 include azo pigments and isoindoline pigments, excluding CI Pigment Yellow 180. In particular, the yellow pigment preferably contains an isoindoline-based pigment.

[0108] The isoindoline pigment is preferably a compound represented by formula (III-1) or formula (III-2).

[0109] [ka] [In formula (III-1), L 1 This represents -CO- or -SO2-. R 31 ~R 37 Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, or a C1-C10 hydrocarbon group which may have substituents. R 38 is -N(R 100 ) Represents a hydrocarbon group having 1 to 10 carbon atoms, which may have 2 or substituents. R 100 This represents a hydrocarbon group having 1 to 10 carbon atoms, which may have a hydrogen atom or substituents. M represents a hydrogen atom or an alkali metal atom. The wavy line indicates E-form or Z-form.

[0110] L 1 It is preferable that it be -CO-.

[0111] R 31 ~R 38 and R 100 The hydrocarbon group represented by the above R 1 ~R 10 Among the compounds represented by , it is preferable that they are similar to hydrocarbon groups having 1 to 10 carbon atoms.

[0112] Examples of alkali metal atoms include sodium atoms and potassium atoms.

[0113] R 31 ~R 38 and R 100 The substituents that the hydrocarbon group represented by may have include halogen atoms, hydroxyl groups, alkoxy groups, alkylsulfanyl groups, formyl groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, nitro groups, cyano groups, substituted or unsubstituted carbamoyl groups, substituted or unsubstituted sulfamoyl groups, -SO3M, etc. The M represents a hydrogen atom or an alkali metal atom (e.g., sodium, potassium).

[0114] R 38 -N(R) 102 )2 is an amino group; Amino groups substituted with one hydrocarbon group having 1 to 10 carbon atoms, such as N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-phenylamino group, etc.; Examples include amino groups substituted with two hydrocarbon groups having 1 to 50 carbon atoms, such as N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N,N-diisopropylamino group, N,N-tert-butylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N-butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, and N,N-di(1-ethylpropyl)amino group.

[0115] R 31 ~R37 It is preferable that it be a hydrogen atom. R 38 is -N(R 102 )2 is preferable. R 102 It is preferably a hydrogen atom or an aliphatic hydrocarbon group, more preferably a hydrogen atom or a linear alkyl group, and even more preferably a hydrogen atom, a methyl group, an ethyl group, or a propyl group. R 38 -NHR is an amino group substituted with one hydrocarbon group having 1 to 10 carbon atoms. 102 It is preferable that this be the case.

[0116] An example of a compound represented by formula (III-1) is CI Pigment Yellow 185.

[0117] [ka] [In formula (III-2), R 41 ~R 47 Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, or a C1-C10 hydrocarbon group which may have substituents. M represents a hydrogen atom or an alkali metal atom.

[0118] R 41 ~R 47 The hydrocarbon group represented by and the substituent of the hydrocarbon group are the above R 31 ~R 38 and the above R 1 ~R 10 It may be the same as this.

[0119] R 41 ~R 47 It is preferable that it be a hydrogen atom.

[0120] An example of a compound represented by formula (III-2) is CI Pigment Yellow 139.

[0121] From the perspective of reducing the transmittance at 430 nm, the isoindoline-based pigment is more preferably a compound represented by formula (III-1).

[0122] The colorant (A) may contain colorants other than those described above. As other colorants (a1), either a dye (hereinafter sometimes referred to as dye (a1-1)) or a pigment (hereinafter sometimes referred to as pigment (a1-2)) may be used.

[0123] The dye (a1-1) is not particularly limited, and known dyes can be used. Examples include solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in the Dyeing Note (Color Dyeing Company). Also, according to the chemical structure, 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, isoindoline dyes, etc. can be mentioned.

[0124] Specific examples of the dye (a1-1) include C.I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; C.I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247; C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. 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; C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. of C.I. Solvent Dyes, C.I. 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; C.I. 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; C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; C.I. 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, 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, 324:1, 335, 340; CI Acid Green dyes such as 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, etc. 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 Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI Direct dyes, CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 60 and other CI disperse dyes, CI Basic 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 Green 1; and other CI Basic dyes, CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive Red 36; and other CI reactive dyes, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Modern Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. CI Modant dyes Examples include CI bat dyes such as CI bat green 1. These dyes (a1-1) may use one or more dyes for each color, or a combination of dyes for each color.

[0125] Examples of pigments (a1-2) include the Color Index (The Society of Dyers and Examples include pigments classified as "pigments" (as published by Colourists).

[0126] Pigments classified as pigments (a1-2) include, specifically, 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, 147, 148, 150, 153, 154, 166, 173, 194, 214, 231, 235, 236, and other yellow pigments; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67; CI Pigment Blue 15, 15:3, 15:4, 15:6, 16, and other blue pigments; CI Pigment Violet 19, 23, 29, 32, 36, 38, and other purple pigments; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1, 7, 31, and 32; and so on. These pigments (a1-2) may consist of one or more pigments for each color, or a combination of pigments for each color.

[0127] At least one pigment selected from the group consisting of yellow pigments, red pigments, and orange pigments may be subjected to, if necessary, rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, graft treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment by ion exchange method for ionic impurities, etc. The particle size of these colorants is preferably substantially uniform. Furthermore, by dispersing these colorants with a pigment dispersant, a uniformly dispersed colorant dispersion can be obtained in a pigment dispersant solution. These colorants may be dispersed individually or multiple types may be mixed and dispersed.

[0128] Examples of the pigment dispersant include surfactants, etc., and any of cationic, anionic, nonionic and amphoteric surfactants may be used. Specifically, surfactants such as polyester-based, polyamine-based and acrylic-based surfactants, etc. are included. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant represented by the trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (registered trademark), BYK (registered trademark) (manufactured by BYK Chemie GmbH), etc.

[0129] When using the pigment dispersant, its usage amount 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 with respect to 100 parts by mass of the colorant. When the usage amount of the pigment dispersant is within the above range, a colorant dispersion liquid in a more uniform dispersion state tends to be obtained when preparing a colorant dispersion liquid containing two or more colorants.

[0130] The content of the first pigment is preferably 55 to 90% by mass, more preferably 57 to 85% by mass, even more preferably 59 to 80% by mass, and even more preferably 60 to 75% by mass in 100% by mass of the colorant.

[0131] The content of the first pigment is preferably 60 to 95% by mass, more preferably 62 to 90% by mass, even more preferably 64 to 85% by mass, and even more preferably 65 to 80% by mass in 100% by mass of the total of the first pigment and the yellow pigment.

[0132] The content of the first pigment is preferably 35 to 80% by mass, more preferably 38 to 75% by mass, even more preferably 41 to 70% by mass, and even more preferably 43 to 65% by mass with respect to the total solid content of the colored curable resin composition.

[0133] The content of the red pigment is preferably 45 to 90% by mass, more preferably 47 to 88% by mass, even more preferably 50 to 85% by mass, and even more preferably 55 to 80% by mass, based on 100% by mass of the total colorants (preferably the first pigment and the yellow pigment).

[0134] The content of the red pigment is preferably 30% to 70% by mass, more preferably 32% to 65% by mass, and even more preferably 34% to 60% by mass, based on the total amount of solids in the colored curable resin composition.

[0135] The content of the orange pigment is preferably 0 to 40% by mass of the total 100% by mass of the colorants (preferably the first pigment and the yellow pigment), more preferably 1 to 35% by mass, and even more preferably 3 to 30% by mass, from the viewpoint of reducing the transmittance at 530 nm.

[0136] The content of the orange pigment is preferably 0 to 30% by mass, more preferably 1 to 25% by mass, and even more preferably 5 to 20% by mass, based on the total amount of solids in the colored curable resin composition, from the viewpoint of reducing the transmittance at 530 nm.

[0137] The ratio of (the orange pigment of the first pigment) to (the red and orange pigments of the first pigment) is preferably 0 to 0.9, more preferably 0.05 to 0.8, even more preferably 0.1 to 0.6, and even more preferably 0.15 to 0.4.

[0138] The total content of the diketopyrrolopyrrole pigment and azo pigment in the first pigment is preferably 80% by mass or more, more preferably 85% by mass or more, and even more preferably 90% by mass or more, based on 100% by mass of the first pigment. The total content of the diketopyrrolopyrrole pigment and azo pigment in the first pigment may be 100% by mass, based on 100% by mass of the first pigment.

[0139] The content of the diketopyrrolopyrrole pigment is preferably 48 to 93% by mass, more preferably 50 to 88% by mass, even more preferably 52 to 83% by mass, and even more preferably 54 to 78% by mass, based on 100% by mass of the coloring agent.

[0140] The content of the diketopyrrolopyrrole pigment (preferably the compound represented by formula (z)) is preferably 70% by mass or more, more preferably 75% by mass or more, even more preferably 80% by mass or more, and even more preferably 85% by mass or more, based on 100% by mass of the red pigment. The content of the diketopyrrolopyrrole pigment (preferably the compound represented by formula (z)) may be 100% by mass, based on 100% by mass of the red pigment.

[0141] The content of the diketopyrrolopyrrole pigment is preferably 50 to 95% by mass, more preferably 52 to 90% by mass, even more preferably 54 to 85% by mass, and even more preferably 56 to 80% by mass, of the total 100% by mass of the diketopyrrolopyrrole pigment and azo pigment of the first pigment.

[0142] The content of the diketopyrrolopyrrole pigment is preferably 30 to 70% by mass, more preferably 32 to 65% by mass, even more preferably 34 to 60% by mass, and even more preferably 36 to 55% by mass, based on the total amount of solids in the colored curable resin composition.

[0143] The content of the azo pigment in the first pigment is preferably 5 to 40% by mass, more preferably 7 to 35% by mass, even more preferably 9 to 30% by mass, and even more preferably 11 to 25% by mass, based on 100% by mass of the colorant.

[0144] The content of the azo pigment in the first pigment is preferably 16 to 75% by mass, more preferably 16 to 70% by mass, and even more preferably 16 to 65% by mass, of 100% by mass of the diketopyrrolopyrrole pigment and azo pigment in the first pigment, and may be 20% or more by mass, 25% by mass, 30% or more by mass, or 35% or more by mass.

[0145] The content of the azo pigment in the first pigment is preferably 5 to 40% by mass, more preferably 10 to 35% by mass, and even more preferably 15 to 30% by mass, relative to the total amount of solids in the colored curable resin composition.

[0146] The ratio of the red azo pigment to the orange azo pigment is preferably 1 or less, more preferably 0.7 or less, even more preferably 0.5 or less, and even more preferably 0.3 or less, and is particularly preferably 0.

[0147] The azo pigment / (first pigment + yellow pigment) of the red pigment is preferably 0.5 or less, more preferably 0.3 or less, even more preferably 0.2 or less, and particularly preferably 0.

[0148] The content of the azo pigment (preferably a compound represented by formula (I)) in the red pigment is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less, based on 100% by mass of the red pigment. The content of the azo pigment (preferably a compound represented by formula (I)) in the red pigment may also be 0% by mass, based on 100% by mass of the red pigment. A low content of the azo pigment in the red pigment results in a lower transmittance at 430 nm.

[0149] The content of the azo pigment (preferably a compound represented by formula (I)) in the red pigment is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less, based on the total amount of solids in the colored curable resin composition. The content of the azo pigment (preferably a compound represented by formula (I)) in the red pigment may be 0% by mass, based on the total amount of solids in the colored curable resin composition.

[0150] The content of the azo pigment (preferably a compound represented by formula (II)) in the orange pigment is preferably 70% by mass or more, more preferably 75% by mass or more, even more preferably 80% by mass or more, and even more preferably 85% by mass or more, based on 100% by mass of the orange pigment. The content of the azo pigment (preferably a compound represented by formula (II)) in the orange pigment may be 100% by mass, based on 100% by mass of the orange pigment.

[0151] The content of the azo pigment (preferably a compound represented by formula (II)) in the orange pigment is preferably 0 to 30% by mass, more preferably 1 to 25% by mass, and even more preferably 2 to 20% by mass, relative to the total amount of solids in the colored curable resin composition.

[0152] The content of the yellow pigment is preferably 4 to 38% by mass, more preferably 8 to 36% by mass, even more preferably 13 to 34% by mass, and even more preferably 18 to 32% by mass, based on 100% by mass of the coloring agent.

[0153] The content of the yellow pigment is preferably 5 to 40% by mass, more preferably 10 to 38% by mass, even more preferably 15 to 36% by mass, and even more preferably 20 to 34% by mass, of the total mass of the first pigment and the yellow pigment.

[0154] The content of the yellow pigment is preferably 5 to 35% by mass, more preferably 7 to 30% by mass, and even more preferably 9 to 25% by mass, based on the total amount of solids in the colored curable resin composition.

[0155] The content of CI Pigment Yellow 180 is preferably 4 to 38% by mass, more preferably 5 to 36% by mass, even more preferably 6 to 34% by mass, and even more preferably 7 to 32% by mass, based on 100% by mass of the coloring agent.

[0156] The content of CI Pigment Yellow 180 is preferably 5 to 40% by mass, more preferably 6 to 38% by mass, even more preferably 7 to 36% by mass, and even more preferably 8 to 34% by mass, of the total of 100% by mass of the first pigment and the yellow pigment. The content of CI Pigment Yellow 180 may be 30% by mass or less of the total 100% by mass of the first pigment and the yellow pigment, from the viewpoint of further reducing the transmittance at 530 nm, and may also be 13% by mass or less of the total 100% by mass of the first pigment and the yellow pigment, from the viewpoint of further reducing the transmittance at 530 nm.

[0157] The content of CI Pigment Yellow 180 is preferably 30 to 100% by mass, more preferably 33 to 90% by mass, even more preferably 35 to 80% by mass, and even more preferably 35 to 70% by mass, based on 100% by mass of yellow pigment. From the viewpoint of further reducing the transmittance at 530 nm, the content of CI Pigment Yellow 180 may be 45% by mass or less out of 100% by mass of yellow pigment.

[0158] The content of CI Pigment Yellow 180 is preferably 1 to 35% by mass, more preferably 2 to 30% by mass, even more preferably 4 to 25% by mass, and even more preferably 5 to 25% by mass, based on the total amount of solids in the colored curable resin composition. The content of CI Pigment Yellow 180 may be 20% by mass or less relative to the total amount of solids in the colored curable resin composition, from the viewpoint of further reducing the transmittance at 530 nm, and may also be 8% by mass or less relative to the total amount of solids in the colored curable resin composition, from the viewpoint of further reducing the transmittance at 530 nm.

[0159] The content of the isoindoline pigment is preferably 0 to 45% by mass, more preferably 1 to 40% by mass, even more preferably 2 to 35% by mass, and even more preferably 5 to 30% by mass, based on 100% by mass of the coloring agent.

[0160] The content of the isoindoline pigment is preferably 0 to 50% by mass, more preferably 1 to 45% by mass, even more preferably 2 to 40% by mass, and even more preferably 5 to 35% by mass, of the total of 100% by mass of the first pigment and the yellow pigment.

[0161] The content of the isoindoline pigment is preferably 0 to 70% by mass, more preferably 10 to 67% by mass, even more preferably 20 to 65% by mass, and even more preferably 30 to 65% by mass, based on 100% by mass of the yellow pigment.

[0162] The content of the isoindoline pigment is preferably 0 to 30% by mass, more preferably 1 to 25% by mass, and even more preferably 2 to 15% by mass, relative to the total amount of solids in the colored curable resin composition.

[0163] The total content of the first pigment and the yellow pigment is preferably 80% by mass or more, more preferably 85% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and particularly preferably 100% by mass, based on 100% by mass of the coloring agent.

[0164] The total content of the colorants (A) (preferably yellow pigment, red pigment, and orange pigment) is, for example, 50 to 95% by mass, preferably 52 to 80% by mass, and more preferably 53 to 70% by mass, based on the total amount of solids in the colored curable resin composition. In this specification, "total amount of solids" refers to the total amount of components of the colored curable resin composition of the present invention, excluding the solvent. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0165] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of 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 monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]; a copolymer having structural units derived from (a) and structural units derived from structural units derived from (b) and a monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]; a copolymer having structural units obtained by adding (b) to structural units derived from (a) and structural units derived from (c), wherein the copolymer includes structural units derived from (a) to which (b) is not added; Resin [K4']; a copolymer having structural units obtained by adding (b) to structural units derived from (a) and structural units derived from (c), and not containing structural units derived from (a) to which (b) is not added; Resin [K5]; a copolymer having structural units obtained by adding (a) to structural units derived from (b) and structural units derived from (c) (it may include structural units derived from (b) to which (a) is not added, but it is preferable that it not be included); Resin [K6]; A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c).

[0166] (a) specifically includes, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0167] (b) refers to a polymerizable compound having, for example, a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0168] Examples of (b) include monomers having an oxyranyl group and an ethylenically unsaturated bond (b1) (hereinafter sometimes referred to as "(b1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (b2) (hereinafter sometimes referred to as "(b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)").

[0169] Examples of (b1) include monomers having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized (b1-1) (hereinafter sometimes referred to as "(b1-1)") and monomers having a cyclic unsaturated hydrocarbon structure that has been epoxidized (b1-2) (hereinafter sometimes referred to as "(b1-2)").

[0170] (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyl Examples include oxymethylstyrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0171] Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer-M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0172] [ka]

[0173] [In formulas (BI) and (BII), R e and R f This represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X e and X fThis is a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g Represents -NH- R g This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0174] Examples of alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxyl group include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group. R e and R f Preferably, the group can be a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0175] Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl. X e and X f Preferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- and *-CH2CH2-O-, and more preferably, single bonds and *-CH2CH2-O- (* represents a bond with O).

[0176] Compounds represented by formula (BI) include those represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BII-5), (BI-7), (BI-9), or (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9), or (BI-15) are more preferred.

[0177] [ka]

[0178] Compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), or (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), or (BII-15) are more preferred.

[0179] [ka]

[0180] The compound represented by formula (BI) and the compound represented by formula (BII) may be used individually or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, their content ratio [compound represented by formula (BI):compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20, on a molar basis.

[0181] For (b2), monomers having an oxetanyl group and a (meth)acryloyloxy group are more preferred. Examples of (b2) include 3-methyl-3-(meth)acryloyloxymethyl oxetane, 3-ethyl-3-(meth)acryloyloxymethyl oxetane, 3-methyl-3-(meth)acryloyloxyethyl oxetane, and 3-ethyl-3-(meth)acryloyloxyethyl oxetane.

[0182] For (b3), monomers having a tetrahydrofurfuryl group and a (meth)acryloyloxy group are more preferred. Specifically for (b3), examples include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0183] (b) is preferable because it allows for greater reliability of the heat resistance, chemical resistance, etc., of the resulting color filter. Furthermore, (b1-2) is more preferable because it provides excellent storage stability for the colored curable resin composition.

[0184] Examples of (c) include (meth)acrylic acid ester monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters; vinyl monomers such as vinyl monomers having an unsaturated aliphatic hydrocarbon ring or an aromatic ring; maleimides; and the like. Examples of (meth)acrylic acid ester monomers include (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups, such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and cyclopentyl (meth)acrylate; (Meth)acrylic acid esters having straight-chain or branched aliphatic unsaturated hydrocarbon groups, such as allyl (meth)acrylate and propargyl (meth)acrylate; Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 (Meth)acrylic acid esters having cyclic saturated hydrocarbon groups, such as decane-8-yl(meth)acrylate (commonly known in the relevant technical field as "dicyclopentanyl(meth)acrylate," and sometimes as "tricyclodecyl(meth)acrylate"), isobornyl(meth)acrylate, and adamantyl(meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having cyclic unsaturated aliphatic hydrocarbon groups, such as decen-8-yl (meth)acrylate (commonly known in the art as "dicyclopentenyl (meth)acrylate") and dicyclopentanyloxyethyl (meth)acrylate; Aromatic ring-containing (meth)acrylic acid esters such as phenyl(meth)acrylate, naphthyl(meth)acrylate, benzyl(meth)acrylate, and phenoxybenzyl(meth)acrylate; Examples include hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate. Examples of unsaturated dicarboxylic acid esters include diethyl maleate, diethyl fumarate, and diethyl itaconate.

[0185] 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 cyclic saturated hydrocarbon groups, such as decane-8-yl(meth)acrylate; Tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters having cyclic unsaturated aliphatic hydrocarbon groups, such as decen-8-yl(meth)acrylate; (Meth)acrylic acid esters having aromatic rings, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate, are preferred.

[0186] Examples of vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (also known as 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, and 5-(2'-hydroxy Ethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6- Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 Examples of bicyclounsaturated compounds include hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene. Examples of vinyl monomers having aromatic rings include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene. Other vinyl monomers include nitrile group-containing monomers such as acrylonitrile and methacrylonitrile; Halogen atom-containing monomers such as vinyl chloride and vinylidene chloride; Examples include acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 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]hepto-2-ene (also known as 2-norbornene) are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0187] Examples of maleimides include N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide. Among these maleimides, maleimides having alicyclic hydrocarbon groups or aromatic hydrocarbon groups, such as N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide, are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0188] A structural unit obtained by adding (b) to a structural unit derived from (a) is 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 examples above, and (b) may also be any of the examples above. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is more preferred.

[0189] A structural unit obtained by adding (a) to a structural unit derived from (b) is a unit formed by adding (a) to a structural unit derived from (b) that constitutes the main chain of the copolymer, and has a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the examples above, and (a) may also be any of the examples above. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0190] A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride is a structural unit in which a hydroxyl group formed by the addition of (a) to a structural unit derived from (b) constituting the main chain of the copolymer is bonded to by the carboxylic acid anhydride through half-esterification, and has a pendant carboxyl group derived from the carboxylic acid anhydride and a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above examples, and (a) may also be any of the above examples. As (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. Examples of carboxylic acid anhydrides include saturated aliphatic polycarboxylic acid anhydrides such as malonic acid anhydride, succinic acid anhydride, glutaric acid anhydride, and adipic acid anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic acid anhydride, citraconic acid anhydride, and itaconic acid anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic acid anhydride and 4-vinylphthalic acid anhydride; and polycarboxylic acid anhydrides such as alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic acid anhydride, 1,2,3,6-tetrahydrophthalic acid anhydride, dimethyltetrahydrophthalic acid anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0191] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. Furthermore, it is preferable that the structural units derived from (c) are substantially omitted. The sum of structural units derived from (a) and structural units derived from (b) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K1]. When the ratio of structural units of resin [K1] is within the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0192] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0193] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents include those described later as solvent (E) of the colored curable resin composition of the present invention.

[0194] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored curable resin composition of the present invention, thereby simplifying the manufacturing process of the colored curable resin composition of the present invention.

[0195] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 1-70 mol% (b) Structural units derived from (b); 1-60 mol% (c) Structural units derived from (c); 20-95 mol% It is preferable that this be the case. (a) Structural units derived from (a); 3-50 mol% (b) Structural units derived from (b); 3-40 mol% (c) Structural units derived from (c); 30-90 mol% It is more preferable that, (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-30 mol% (c) Structural units derived from (c); 40-80 mol% It is even more preferable that it be so. The sum of structural units derived from (a), (b), and (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K2]. When the ratio of structural units of resin [K2] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0196] In resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. For (b), a monomer (b1) having an oxiranil group and an ethylenically unsaturated bond is preferred, and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized is more preferred. For (c), (meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, and dicarbonylimide derivatives are preferred.

[0197] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0198] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from this structure; 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is more preferable that, (a) Structural units derived from (a); 35-45 mol% (c) Structural units derived from (c); 55-65 mol% It is even more preferable that it be so. Furthermore, it is preferable that the structural units derived from (b) are substantially omitted. The sum of structural units derived from (a) and structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K3].

[0199] In resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (c) is preferably (meth)acrylic acid esters having an aromatic ring. Resin [K3] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0200] In resin [K4], the ratio of structural units derived from each is, among all structural units constituting resin [K4], (a) Structural units derived from (b) (without addition); 1-60 mol% A structural unit obtained by adding (b) to a structural unit derived from (a); 1-50 mol% (c) Structural units derived from (c); 30-90 mol% It is preferable that this be the case. (a) Structural units derived from (b) (without addition); 5-50 mol% A structural unit obtained by adding (b) to a structural unit derived from (a); 5-40 mol% (c) Structural units derived from (c); 35-80 mol% It is more preferable that, (a) Structural units derived from (b) (without addition); 10-40 mol% A structural unit obtained by adding (b) to a structural unit derived from (a); 10-25 mol% (c) Structural units derived from this structure; 40-75 mol% It is even more preferable that it be so. The sum of structural units derived from (a) (without (b) added), structural units derived from (a) with (b) added, and structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K4].

[0201] As structural units derived from (a) (without (b) being added), structural units derived from unsaturated monocarboxylic acids such as (meth)acrylic acid are preferred. As structural units obtained by adding (b) to structural units derived from (a), structural units obtained by adding a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid are preferred. As structural units derived from (c), one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups, (meth)acrylic acid esters having cyclic saturated hydrocarbon groups, (meth)acrylic acid esters having aromatic rings, bicyclounsaturated compounds, and styrene monomers are preferred, and two or more are more preferred. When (c) has two constituent units derived from (c), it is preferable to select two from unsaturated carboxylic acid esters such as (meth)acrylic acid esters, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring, and to select two or more from bicyclounsaturated compounds and vinyl monomers such as styrene monomers.

[0202] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as described in the method for producing resin [K1]. In this case, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0203] Next, a portion of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.) and a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.) are added to the flask and the mixture is reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored curable resin composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0204] In resin [K4'], the ratio of structural units derived from each is, among all structural units constituting resin [K4'], A structural unit obtained by adding (b) to a structural unit derived from (a); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. A structural unit obtained by adding (b) to a structural unit derived from (a); 15-90 mol% (c) Structural units derived from (c); 10-85 mol% It is more preferable that, A structural unit obtained by adding (b) to a structural unit derived from (a); 20-80 mol% (c) Structural units derived from (c); 20-80 mol% It is even more preferable that it be so. Furthermore, structural units derived from (a) but without (b) attached are not substantially included. The sum of structural units derived from (a) with (b) added, and structural units derived from (c), is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K4'].

[0205] As a structural unit obtained by adding (b) to a structural unit derived from (a), a preferred structural unit is one obtained by adding a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. As a structural unit derived from (c), one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups and (meth)acrylic acid esters having cyclic saturated hydrocarbon groups are preferred, and two or more are more preferred. The resin [K4'] may be prepared by referring to the above method for producing resin [K4], and the amount of (b) used is preferably 100 moles or more, and more preferably 100 moles, per 100 moles of (a).

[0206] In resin [K5], the ratio of structural units derived from each is, among all structural units constituting resin [K5], (b) Structural units derived from (a) (without addition of (a)); 0-30 mol% Structural units obtained by adding (a) to structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (a) (without addition); 0-10 mol% Structural units obtained by adding (a) to structural units derived from (b); 15-90 mol% (c) Structural units derived from (c); 10-85 mol% It is more preferable that, (b) Structural units derived from (a) (without addition); 0-5 mol% Structural units obtained by adding (a) to structural units derived from (b); 20-80 mol% (c) Structural units derived from (c); 20-80 mol% It is even more preferable that this be the case. The sum of structural units derived from (b) (without (a) added), structural units derived from (b) with (a) added, and structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K5].

[0207] As structural units derived from (b) (without (a) attached), structural units derived from monomers (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized are preferred. As structural units obtained by attaching (a) to structural units derived from (b), structural units obtained by attaching an unsaturated monocarboxylic acid such as (meth)acrylic acid to structural units derived from monomers (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized are preferred. As structural units derived from (c), one or more selected from (meth)acrylic acid esters having linear or branched aliphatic saturated hydrocarbon groups and (meth)acrylic acid esters having cyclic saturated hydrocarbon groups are preferred, and two or more are more preferred.

[0208] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0209] Furthermore, resin [K5] can be obtained by reacting a cyclic ether derived from (b) in a copolymer of (b) and (c) with a carboxylic acid or carboxylic acid anhydride from (a) under the same conditions as for the production of resin [K4] or resin [K4']. The amount of (a) used to react with the copolymer is preferably 5 to 100 moles, and more preferably 60 to 100 moles, per 100 moles of (b). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is even more preferred.

[0210] In resin [K6], the ratio of structural units derived from each is, among all structural units constituting resin [K6], (b) Structural units derived from (a) (without addition of (a)); 0-30 mol% (b) is a structural unit to which (a) is added (no carboxylic acid anhydride is added); 5-70 mol% A structural unit obtained by adding (a) to a structural unit derived from (b), and then adding a carboxylic acid anhydride; 10-80 mol% (c) Structural units derived from (c); 10-60 mol% It is preferable that this be the case. (b) Structural units derived from (a) (without addition); 0-10 mol% (b) is a structural unit to which (a) is added (no carboxylic acid anhydride is added); 10-50 mol% A structural unit obtained by adding (a) to a structural unit derived from (b), and then adding a carboxylic acid anhydride; 25-60 mol% (c) Structural units derived from (c); 15-50 mol% It is more preferable that, (b) Structural units derived from (a) (without addition); 0-5 mol% (b) is a structural unit to which (a) is added (no carboxylic acid anhydride is added); 15-35 mol% A structural unit obtained by adding (a) to a structural unit derived from (b), and then adding a carboxylic acid anhydride; 35-55 mol% (c) Structural units derived from this structure; 20-40 mol% It is even more preferable that it be so.

[0211] The sum of structural units derived from (b) (without (a) added), structural units obtained by adding (a) to structural units derived from (b) (without carboxylic acid anhydride added), structural units obtained by adding (a) to structural units derived from (b) and further adding carboxylic acid anhydride, and structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of the total structural units constituting the resin [K6].

[0212] As a structural unit derived from (b) (without (a) being added), a structural unit derived from a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is preferred. As a structural unit obtained by adding (a) to a structural unit derived from (b) (without carboxylic acid anhydride being added), a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit derived from a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is preferred. As a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit derived from a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized is preferred, and further adding a saturated aliphatic polycarboxylic acid anhydride such as succinic anhydride is preferred. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having 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.

[0213] As a first step, resin [K6] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0214] Furthermore, under the same conditions as for the production of resin [K4], the cyclic ether derived from (b) in the copolymer of (b) and (c) is reacted with the carboxylic acid or carboxylic acid anhydride of (a). The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0215] The hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic acid anhydride of (a) is reacted with the carboxylic acid anhydride. The amount of carboxylic acid anhydride used is preferably 0.05 to 1 mole, more preferably 0.10 to 0.8 moles, and even more preferably 0.13 to 0.7 moles, relative to 1 mole of (a) used (in other words, 1 mole of hydroxyl groups produced by the use of (a)).

[0216] Specifically, resin (B) is 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / tricyclo[5.2.1.0 2,6 ] Decen-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6Resins such as decyl acrylate / (meth)acrylic acid / phenoxybenzyl(meth)acrylate copolymer and 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymers and styrene / (meth)acrylic acid copolymers [K3]; Resins such as those obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl (meth)acrylate to some of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer [K4]; Resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / (meth)acrylic acid copolymer with glycidyl (meth)acrylate, and resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer with glycidyl (meth)acrylate [K4']; Resins such as resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, and resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; Examples of resins include those obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with tetrahydrophthalic anhydride; a resin obtained by reacting a 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with succinic anhydride; a resin obtained by reacting a methyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting that with succinic anhydride; and so on [K6].

[0217] Resin (B) may be used alone or in combination of two or more types. Preferably, resin (B) is at least one selected from resins [K1], [K2], [K4], and [K6], with resin [K2] being more preferred.

[0218] The weight-average molecular weight of resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the color pattern tends to improve. The degree of dispersion of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0219] The acid value of 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, based on solid content. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0220] The content of resin (B) is preferably 5 to 40% by mass, more preferably 7 to 35% by mass, and even more preferably 9 to 30% by 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 improve.

[0221] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples include compounds having polymerizable ethylenically unsaturated bonds, and is preferably a (meth)acrylic acid ester compound.

[0222] In particular, polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tripentaerythritol oc (meth)acrylate, tripentaerythritol heptate (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) (T)acrylate, propylene glycol-modified pentaerythritol tri(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, alkylene glycol-modified dipentaerythritol poly(meth)acrylate (for example, ethylene glycol-modified dipentaerythritol penta(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified dipentaerythritol penta(meth)acrylate, propylene glycol-modified Examples include poly(meth)acrylates such as dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), and caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate). In particular, it is preferable that it be 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, and more preferably ethylene glycol-modified pentaerythritol poly(meth)acrylate and ethylene glycol-modified dipentaerythritol poly(meth)acrylate.

[0223] The hydroxyl value of 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.

[0224] The number of ethylene glycol units in 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.

[0225] The content of polymerizable compound (C) is, for example, 5 to 40% by mass, preferably 6 to 35% by mass, and more preferably 8 to 30% by mass, relative to the total amount of solids in the colored curable resin composition. When the content of polymerizable compound (C) is within the above range, the residual film rate when forming the colored pattern and the chemical resistance of the color filter tend to improve.

[0226] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc., upon the action of light or heat and can initiate polymerization; any known polymerization initiator can be used.

[0227] Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0228] The O-acyloxime compound is a compound having a substructure represented by formula (d1). Hereinafter, * represents a bond.

[0229] [ka]

[0230] Examples of the O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N- Examples include acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, O-acyloxime compounds include N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1- At least one selected from the group consisting of on-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-on-2-imine is preferred, and at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-on-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-on-2-imine is more preferred. These O-acyloxime compounds tend to yield high-brightness color filters.

[0231] The alkylphenone compound is preferably a compound having a substructure represented by formula (d2) or formula (d3). In these substructures, the benzene ring may have substituents.

[0232] [ka]

[0233] Examples of compounds having the substructure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.

[0234] Examples of compounds having the substructure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal. In terms of sensitivity, alkylphenone compounds having the substructure represented by formula (d2) are preferred.

[0235] Examples of the aforementioned triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ Examples include 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0236] Examples of the aforementioned acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0237] Examples of the biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2- Examples include chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0238] Furthermore, examples of polymerization initiators (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) described later.

[0239] Examples of polymerization initiators that generate acids include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, as well as nitrobenzyl tosylates and benzoin tosylates.

[0240] The polymerization initiator (D) is preferably one containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and a polymerization initiator containing an O-acyloxime compound is more preferred. The content of the O-acyloxime compound in 100% by mass of 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.

[0241] 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, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time is shortened, thus improving the productivity of color filters.

[0242] <Polymerization initiator (D1)> The colored curable resin composition of the present invention may further contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0243] Examples of the amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0244] Examples of the alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0245] Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0246] Examples of the carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.

[0247] When these polymerization initiators (D1) are used, their content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the amount of polymerization initiator (D1) is within this range, it is possible to form a colored pattern with even higher sensitivity, and the productivity of color filters tends to improve.

[0248] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing both -CO- and -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, and the like.

[0249] 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.

[0250] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole.

[0251] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxypropionate Examples include ethyl xy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0252] 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.

[0253] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0254] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0255] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0256] Of the above solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred from the viewpoint of applicability and drying properties. As the solvent, at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide is preferred, and at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate is more preferred.

[0257] Furthermore, it is also preferable to use a combination of ether solvents and ether ester solvents as solvent (E). In this case, C is used as the ether solvent. 2-3 Alkylene glycol mono C 1-4Alkyl ethers are preferred, and propylene glycol monoC 1-4 Alkyl ethers are more preferred. Also, as an ether ester solvent, C 2-3 Alkylene glycol mono C 1-4 Alkyl ether acetate is preferred, and propylene glycol monoC 1-4 Alkyl ether acetate is more preferred.

[0258] The solvent (E) content is preferably 70 to 95% by mass, more preferably 73 to 92% by mass, and even more preferably 76 to 89% by mass, relative to the total amount of the colored curable resin composition. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 27% by mass, and even more preferably 11 to 24% by mass. When the solvent (E) content is within the above range, the flatness during coating is good, and when a color filter is formed, there is no shortage of color density, which tends to result in good display characteristics and sensitivity.

[0259] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0260] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0261] Examples of the aforementioned fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc. (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0262] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0263] The content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and even more preferably 0.005 to 0.05% by mass, relative to the total amount of the colored curable resin composition. This content does not include the content of the pigment dispersant mentioned above. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0264] <Other ingredients> The colored curable resin composition may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.

[0265] <Method for producing a colored curable resin composition> A 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 mixed colored curable resin composition may be filtered through a filter with a pore size of approximately 0.01 to 10 μm.

[0266] As described above, the colorant (A) may be used as a uniformly dispersed colorant dispersion in a solution by dispersing it with a pigment dispersant. The desired colored curable resin composition can be prepared by mixing the remaining components to such a colorant dispersion to a predetermined concentration.

[0267] Furthermore, if the coloring agent (A) contains a dye, the solution may be prepared by dissolving part or all of the dye in the solvent (E) beforehand. It is preferable to filter the solution through a filter with a pore size of approximately 0.01 to 1 μm.

[0268] [Color Filter] Methods for producing a colored pattern on a color filter from the colored curable resin composition of the present invention include photolithography, inkjet printing, and other printing methods. Among these, photolithography is preferred. 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 for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the composition layer, can be formed.

[0269] The film thickness of the color filter (colored coating 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, even more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0270] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used; silicon is used; and aluminum, silver, and silver / copper / palladium alloy thin films are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates. Alternatively, a substrate treated with HMDS on a silicon substrate may be used.

[0271] The formation of each color pixel (color filter) by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows: First, a colored curable resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying to obtain a smooth composition layer. Application methods include spin coating, slit coating, and slit and spin coating. When performing heat drying, the temperature is preferably 30 to 120°C, and more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited and can be appropriately selected according to the desired film thickness of the color filter.

[0272] Next, the composition layer is exposed via a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. A light source that generates light with a wavelength of 250 to 450 nm is preferred for exposure. For example, light below 250 nm can be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. It is preferable to use a reduction projection exposure apparatus or proximity exposure apparatus such as a mask aligner and stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment of the photomask and the substrate.

[0273] A colored pattern is formed on the substrate by developing the exposed composition layer in contact with a developer. During development, the unexposed parts of the composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developer may also contain a surfactant. The development method may be any of the following: the paddle method, the dipping method, and the spray method. Furthermore, the substrate may be tilted at any angle during development. After developing, it is preferable to wash the film with water.

[0274] Furthermore, it is preferable to perform a post-bake on the obtained coloring pattern. The post-bake temperature is preferably 80 to 250°C, and more preferably 100 to 245°C. The post-bake time is preferably 1 to 120 minutes, and more preferably 2 to 30 minutes.

[0275] The colored patterns and colored coatings obtained in this manner are useful as color filters, and these color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state image sensors, etc. [Examples]

[0276] The present invention will be described in more detail below with reference to examples, but the present invention is not limited by the following examples, and it is certainly possible to implement it with appropriate modifications within the scope that is consistent with the spirit of the preceding and following descriptions, and all such modifications are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "percent mass".

[0277] In the following examples, the structure of the compounds was confirmed by mass spectrometry (LC: Agilent 1200, MASS: Agilent LC / MSD6130).

[0278] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, calculated on a polystyrene basis, were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid content concentration of the analytical sample: 0.001~0.01% Injection volume: 50μL Detector: RI Calibration standards: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight-average molecular weight to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0279] <Coloring agent (A): Example of synthesis of compound (I-1)> In accordance with International Publication No. 2022 / 065357, compound (I-1), an orange pigment represented by the following formula, was synthesized.

[0280] [ka]

[0281] <Coloring agent (A): Example of synthesis of compound (Ia-61)> A compound represented by the following formula (Ia-61) was synthesized in accordance with the description in Example 1 of Japanese Patent Publication No. 2013-161026.

[0282] [ka]

[0283] <Coloring agent (A): Example of synthesis of compound (Ib-522)> A compound represented by the following formula (Ib-522) was synthesized in accordance with the description in Example 1 of Japanese Patent Publication No. 2017-142503.

[0284] [ka]

[0285] <Example of resin (B-1) synthesis> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 340 parts of propylene glycol monomethyl ether acetate were added and heated to 80°C while stirring. Then, 57 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixed solution of 54 parts of decane-9-yl acrylate (with a molar ratio of 1:1), 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 addition of the initiator solution was complete, the mixture was held at 80°C for 3 hours, then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a viscosity of 127 mPas and a solid content of 37.0 wt%, as measured by a B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.4 × 10⁻⁶. 3 The dispersion was 1.89, and the acid value on a solid content basis was 114 mg-KOH / g. Resin (B-1) has the following structural units.

[0286] [ka]

[0287] <Preparation of colorant dispersions (A-1) to (A-10)> A colorant dispersion was obtained by mixing each component in the proportions listed in Table 18 and dispersing them in a bead mill.

[0288] [Table 18]

[0289] Preparation of a colored curable resin composition <Examples 1-10 and Comparative Example 1> A colored curable resin composition was obtained by mixing each component in the proportions shown in Table 19.

[0290] [Table 19]

[0291] <Polymerizable compound (C)> Polymerizable compound (C): Compound represented by the following formula (NK ester A-DPH-12E: manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0292] [ka]

[0293] <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

[0294] <Creating a colored pattern> A colored curable resin composition was applied to the surface of a 4-inch silicon substrate by spin coating, and then pre-baked at 100°C for 2 minutes to obtain a colored composition layer. After cooling, the substrate with the colored composition layer was exposed to 500 J / m² using an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation). 2 ~3000 J / m 2 The samples were irradiated with light at an exposure level of 365 nm. Photomasks (with pitches of 1.6 μm, 2.0 μm, and 4.0 μm, respectively) were used to form dot patterns of 0.8 μm, 1.0 μm, and 2.0 μm squares during light irradiation. The colored composition layer after light irradiation was developed by immersion 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 the post-baked colored pattern.

[0295] <Film thickness measurement> The film thickness of the obtained colored patterns was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.). The results are shown in Table 20.

[0296] [Table 20]

[0297] <Transmittance Evaluation> The obtained color patterns were measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) to determine the transmittance in the wavelength range of 380 nm to 780 nm at 1 nm intervals. A lower transmittance at 530 nm indicates less green light leakage and suggests superior color performance as a color filter (especially a red color filter). The results are shown in Table 21.

[0298] [Table 21]

[0299] Furthermore, a lower transmittance at 430nm indicates less blue light leakage, suggesting superior color performance as a color filter (especially a red color filter). The results are shown in Table 22.

[0300] [Table 22]

[0301] The results in Table 21 show that Examples 1 to 10 can reduce crosstalk to the green pixel region without green light leakage. The results in Table 22 show that Examples 3-10 can reduce crosstalk to the blue pixel region, particularly by eliminating blue light leakage.

Claims

1. A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, The coloring agent comprises a first pigment consisting of at least one selected from an orange pigment and a red pigment, and a yellow pigment. The first pigment comprises a diketopyrrolopyrrole pigment and an azo pigment, A colored curable resin composition wherein the yellow pigment comprises C.I. Pigment Yellow 180.

2. The colored curable resin composition according to claim 1, wherein the content of the first pigment is 60 to 95% by mass of the total of the first pigment and the yellow pigment in 100% by mass.

3. The colored curable resin composition according to claim 1 or 2, wherein the azo pigment of the red pigment is a compound represented by formula (I). 【Chemistry 1】 [In formula (I), X 1 This is 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 It represents. X 2 This includes a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, and -OR 1 , or -COOR 2 It 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 -SONR 2 R 7 R 8 . R 1 ~R 8 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. l represents an integer between 0 and 4. n represents either 1 or 2. m represents an integer from 0 to 5. The sum of m and n is an integer less than or equal to 6. X 1 , X 2 , or X 3 If multiple instances exist, they may be identical or different.

4. The colored curable resin composition according to claim 1 or 2, wherein the orange azo pigment is a compound represented by formula (II). 【Chemistry 2】 [In formula (II), L 1 This represents a divalent aromatic hydrocarbon group which may have substituents. X 11 ~X 14 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents.

5. A color filter formed from the color-curable resin composition described in claim 1 or 2.

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

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

Images