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

Abstract

The invention relates to a colored curable resin composition, a color filter, a display device and a solid-state imaging device. The present invention addresses the problem of providing a colored curable resin composition capable of reducing crosstalk in a color filter. The present invention relates to a colored curable resin composition comprising a colorant, a resin, a polymerizable compound and a polymerization initiator, the colorant comprising at least one selected from the group consisting of red pigment and orange pigment, C.I. Pigment yellow 185 and xanthene pigment.

Description

TECHNICAL FIELD

[0001] The present application relates to a colored curable resin composition, a color filter formed from the colored curable resin composition, a display device including the color filter, and a solid-state imaging device including the color filter. BACKGROUND

[0002] A color filter used in a liquid crystal display device, an organic electroluminescent display device, a plasma display, and the like, a solid-state imaging device such as a CCD, and a CMOS sensor is manufactured from a colored resin composition. As such a colored resin composition, various colorants are used, and, for example, as a colorant, C.I. Pigment Red 254, C.I. Pigment Red 242, C.I. Pigment Yellow 139, and C.I. Pigment Yellow 185 are known to be used (Patent Document 1).

[0003] PRIOR ART DOCUMENTS

[0004] PATENT DOCUMENTS

[0005] Patent Document 1: Japanese Patent Application Publication No. 2023-39409 SUMMARY

[0006] PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] In the case where a color filter is used with a sensor such as a solid-state imaging device, with high resolution, it is necessary to make the pixels finer, and there is a problem in that a phenomenon in which light that has passed through a prescribed color filter leaks to a filter region of another color (for example, crosstalk) occurs, and the quantum efficiency of the pixels cannot be improved.

[0008] Therefore, an object of the present application is to provide a colored curable resin composition that can reduce crosstalk of a color filter.

[0009] MEANS FOR SOLVING THE PROBLEMS

[0010] That is, the gist of the present application is as described below.

[0011] [1] A colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant including at least one selected from the group consisting of a red pigment and an orange pigment, C.I. Pigment Yellow 185, and a xanthene dye.

[0012] [2] The colored curable resin composition according to [1], wherein the content ratio of the xanthene dye is 1% by mass or more and 40% by mass or less with respect to the total amount of the colorant.

[0013] [3] The colored curable resin composition according to [1] or [2], wherein the total content of at least one selected from the group consisting of a red pigment and an orange pigment is 10 to 65 mass% with respect to the entire amount of the colorant.

[0014] [4] The colored curable resin composition according to any one of [1] to [3], wherein the content of C.I. Pigment Yellow 185 is 6 to 50 mass% with respect to the entire amount of the colorant.

[0015] [5] The colored curable resin composition according to any one of [1] to [4], wherein the red pigment and the orange pigment include a pigment having one or more skeletons selected from the group consisting of a pyrrolopyrylo skeleton and an azo skeleton.

[0016] [6] A color filter formed of the colored curable resin composition according to any one of [1] to [5].

[0017] [7] The color filter according to [6], wherein, in a transmission spectrum in which a wavelength is taken as a horizontal axis and a transmittance is taken as a vertical axis, a slope calculated based on a minimum wavelength λ1 at which a transmittance of 70% or more is satisfied in a range of 580 nm or more in wavelength and a transmittance T1 at the wavelength λ1, and a maximum wavelength λ2 at which a transmittance of 30% or less is satisfied in a range of less than 580 nm in wavelength and a transmittance T2 at the wavelength λ2, is 0.03 to 0.06.

[0018] Slope = (T1 - T2) / (λ1 - λ2)

[0019] [8] A display device including the color filter according to [6] or [7].

[0020] [9] A solid-state imaging device including the color filter according to [6] or [7].

[0021] Effects of Invention

[0022] According to the present application, crosstalk of a color filter can be reduced. DETAILED DESCRIPTION

[0023] [Colored Curable Resin Composition]

[0024] The present application includes a colored curable resin composition containing a colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)), the colorant (A) containing at least one selected from the group consisting of a red pigment and an orange pigment, C.I. Pigment Yellow 185, and a xanthene dye. By using such a colored curable resin composition, a color filter that reduces crosstalk can be produced, preferably, a color filter that reduces crosstalk and prevents color mixing to green can be produced.

[0025] The colored curable resin composition of the present application can contain a solvent (hereinafter, sometimes referred to as solvent (E)).

[0026] The colored curable resin composition of the present application can contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0027] In the present specification, unless otherwise specified, the compounds exemplified as each component can be used singly or in combination of a plurality.

[0028] In the present application, based on the following conditions, a red pigment is defined as a pigment having a maximum absorption wavelength of more than 500 nm, and an orange pigment is defined as a pigment having a maximum absorption wavelength of more than 460 nm and 500 nm or less.

[0029] [Condition] A colored curable resin composition containing only one colorant and having a content of the colorant of 10% by mass in the solid content of the composition was prepared, and the absorbance in the visible region (wavelength 400 to 780 nm) was measured for a color filter having a film thickness of 1 μm formed from the composition.

[0030] [Colorant (A)]

[0031] The xanthene dye is a compound having a xanthene skeleton in the molecule. As the xanthene dye, for example, C.I. Acid Red 50, 51 (hereinafter, the description of C.I. Acid Red is omitted, and only the number is described. The same applies to others.), 52, 87, 91, 92, 94, 95, 98, 289, 388, C.I. Acid Violet 9, 30, 102, C.I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, C.I. Basic Violet 10 (Rhodamine B), 11, C.I. Solvent Red 218, C.I. Mordant Red 27, C.I. Reactive Red 36 (Rose Bengal B), sulforhodamine G, C.I. Pigment Red 81, 169, 173, C.I. Pigment Violet 1, 2, the xanthene dyes described in Japanese Patent Application Publication No. 2010-32999, the xanthene dyes described in Japanese Patent No. 4492760, and the like can be given.

[0032] The xanthene dye preferably contains a compound represented by formula (1). The compound represented by formula (1) can be a tautomer thereof.

[0033]

[0034] [In formula (1),

[0035] R 1 ~R 4 each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent, an aromatic hydrocarbon group having 6 to 30 carbon atoms which can have a substituent, or a group represented by *-R 12 -Si(R 13 )3 ( * indicates a bonding position to a nitrogen atom), R 1 and R 2 may form a ring containing a nitrogen atom together. 3 and R 4 may form a ring containing a nitrogen atom together.

[0036] R 5 represents -OH, -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 , -SO3R 8 , or -SO2NR 9 R 10 .

[0037] R 6 ~R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0038] R 8 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which can be substituted with a halogen atom.

[0039] R 9 and R 10 each independently represent a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent, R 9 and R 10 may form a ring containing a nitrogen atom together.

[0040] R 12 represents an alkanediyl group having 1 to 10 carbon atoms, and -CH2- included in the aforementioned alkanediyl group can be replaced with -O-, -CO-, -NR 8 -, -OCO-, -COO-, -OCONH-, -CONH-, or -NHCO-.

[0041] R 13 represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and a plurality of R 13 Each of R1to R4may be the same or different.

[0042] Z + represents an arbitrary cation.

[0043] X represents a halogen atom.

[0044] a represents 0 or 1.

[0045] m represents an integer of 0 to 5, and when m is 2 or more, a plurality of R 5 may be the same or different.

[0046] R 1 to R 4 , and R 8 to R 10 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R

[0047] The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 4 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably an alkyl group having 1 to 5 carbon atoms, and particularly preferably an alkyl group having 2 to 4 carbon atoms.

[0048] The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 8 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and further preferably an alkyl group having 1 to 4 carbon atoms.

[0049] The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 9 to R 10 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and further preferably an alkyl group having 4 to 10 carbon atoms.

[0050] The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 4The saturated hydrocarbon group with 1 to 20 carbon atoms may have substituents. Examples of such substituents include: aryl groups such as phenyl, tolyl, xylyl, and mesitylelel; halogen atoms such as fluorine, chlorine, bromine, and iodine; hydroxyl groups; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; carboxyl groups; alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and butoxycarbonyl; amino groups; alkyl-substituted amino groups such as N-methylamino, N-ethylamino, and N,N-dimethylamino; and so on. Among these, halogen atoms, hydroxyl groups, and carboxyl groups are preferred, and carboxyl groups are more preferred.

[0051] R 8 The saturated hydrocarbon group with 1 to 20 carbon atoms can be replaced by a halogen atom. Examples of such halogen atoms include fluorine, chlorine, bromine, and iodine.

[0052] R 9 and R 10 The saturated hydrocarbon group representing 1 to 20 carbon atoms can have substituents. Examples of such substituents include those related to R. 1 ~R 4 The saturated hydrocarbon group representing 1 to 20 carbon atoms may have the same substituents. Among them, halogen atoms and hydroxyl groups are preferred.

[0053] As R 1 ~R 4 Aromatic hydrocarbon groups with 6 to 30 carbon atoms can be represented by: phenyl; alkylphenyl groups such as tolyl, xylyl, mesitylelel, propylphenyl, and butylphenyl; arylphenyl groups such as biphenyl and diphenylphenyl; naphthyl; and so on.

[0054] As alkyl groups constituting alkylphenyl groups, examples include those that are R 1 ~R 4 The alkyl group in the saturated hydrocarbon group representing 1 to 20 carbon atoms is described, preferably an alkyl group with 1 to 10 carbon atoms, more preferably an alkyl group with 1 to 4 carbon atoms, and even more preferably a methyl group. As an alkylphenyl group, it is preferred that the alkyl group has an alkyl group at at least one of the two bonding positions adjacent to the N bonded to the phenyl group, more preferably a group having an alkyl group at the two bonding positions adjacent to the N bonded to the phenyl group.

[0055] Specifically, the zeaxanthin pigment preferably contains R 1 ~R 4 At least one of the compounds is an alkylphenyl compound, more preferably containing R 1 ~R 4 Compounds in which at least two are alkylphenyl groups, and more preferably contain R 1 and R 4 It is a compound of alkylphenyl groups.

[0056] Examples of aryl groups constituting arylphenyl groups include: phenyl; alkylphenyl groups such as tolyl, xylyl, mesitylene, propylphenyl, and butylphenyl; etc., wherein an aryl group having 6 to 10 carbon atoms is preferred, and a phenyl group is more preferred. As an arylphenyl group, it is preferred to have an aryl group at at least one of the two bonding positions adjacent to the N bonded to the phenyl group, and a group having an aryl group at the two bonding positions adjacent to the N bonded to the phenyl group is more preferred.

[0057] Specifically, as R 1 ~R 4 The group represents an aromatic hydrocarbon group with 6 to 30 carbon atoms.

[0058] Preferably, the aromatic hydrocarbon group has 6 to 20 carbon atoms.

[0059] More preferably, it is an alkylphenyl having an alkyl group at at least one of the two bonding positions adjacent to the N group bonded to the phenyl group; or, it is an arylphenyl having an aryl group at at least one of the two bonding positions adjacent to the N group bonded to the phenyl group.

[0060] Further preferred is an alkylphenyl having an alkyl group at two bonding positions adjacent to the N group bonded to the phenyl group; or an arylphenyl having an aryl group at two bonding positions adjacent to the N group bonded to the phenyl group.

[0061] R 1 ~R 4 Aromatic hydrocarbon groups with 6 to 30 carbon atoms can have substituents. Examples of such substituents include halogen atoms, -OH, and -OR. 8 -SO3 - -SO3H, -SO3 - Z + -CO2H, -CO2R 8 -SR 8 -SO2R 8 -SO3R 8 -SO2NR 9 R 10 Among these, SO3 is preferred. - -SO3H, -SO3 - Z + -SO2NR 9 R 10 More preferably -SO3 - -SO3 - Z + -SO2NR 9 R 10 As for -SO3 in this case- Z + Preferred SO3 - N + (R 11 4. It should be noted that when an aromatic hydrocarbon group with 6 to 30 carbon atoms has a substituent, it is preferable that the substituent is directly bonded to the aromatic hydrocarbon ring.

[0062] Z + Preferred ammonium cations, Na + or K + More preferably, ammonium cations are used. Ammonium cations are not limited to NH4+. + This refers to organic ammonium cations such as primary ammonium cations, secondary ammonium cations, tertiary ammonium cations, and quaternary ammonium cations, with quaternary ammonium cations being preferred. Examples of ammonium cations containing -N... + (R 11 )3 as a partially structured polymer, N + (R 11 4. Multiple R 11 They can be the same or different.

[0063] R 11 It represents a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbon atoms, or an aralkyl group with 7 to 10 carbon atoms.

[0064] As R 11 The saturated hydrocarbon group represented by the carbon group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 15 carbon atoms.

[0065] As R 11 Aryl groups representing 7 to 10 carbon atoms include benzyl, phenylethyl, phenylpropyl, phenylbutyl, and naphthylmethyl.

[0066] As mentioned above, N + (R 11 4. Select four Rs 11 At least two of them are saturated hydrocarbon groups with 5 to 20 carbon atoms (especially alkyl groups with 5 to 20 carbon atoms). Additionally, the four R... 11 The total number of carbon atoms is preferably 20 to 80, more preferably 20 to 60.

[0067] As -OR 8 Examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, 2-ethylhexoxy, and eicosyloxy.

[0068] As -CO2R 8 Examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, hexoxycarbonyl, and eicosyloxycarbonyl.

[0069] As -SR 8 Examples include methylsulfanyl, ethylsulfanyl, butylsulfanyl, hexylsulfanyl, decylsulfanyl, and eicosylsulfanyl.

[0070] As -SO2R 8 Examples include methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl, and eicosylsulfonyl.

[0071] As -SO3R 8 Examples include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, butoxysulfonyl, hexoxysulfonyl, and eicosyloxysulfonyl.

[0072] As -SO2NR 9 R 10 Examples include:

[0073] Aminosulfonyl;

[0074] N-Methylaminosulfonyl, N-ethylaminosulfonyl, N-propylaminosulfonyl, N-isopropylaminosulfonyl, N-butylaminosulfonyl, N-isobutylaminosulfonyl, N-sec-butylaminosulfonyl, N-tert-butylaminosulfonyl, N-pentylaminosulfonyl, N-(1-ethylpropyl)aminosulfonyl, N-(1,1-dimethylpropyl)aminosulfonyl, N-(1,2-dimethylpropyl)aminosulfonyl, N-(2,2-dimethylpropyl)aminosulfonyl, N-(1-methylbutyl)amino N-monosubstituted aminosulfonyl groups include sulfonyl, N-(2-methylbutyl)aminosulfonyl, N-(3-methylbutyl)aminosulfonyl, N-cyclopentylaminosulfonyl, N-hexylaminosulfonyl, N-(1,3-dimethylbutyl)aminosulfonyl, N-(3,3-dimethylbutyl)aminosulfonyl, N-heptylaminosulfonyl, N-(1-methylhexyl)aminosulfonyl, N-(1,4-dimethylpentyl)aminosulfonyl, N-octylaminosulfonyl, and N-(2-ethylhexyl)aminosulfonyl.

[0075] N,N-dimethylaminosulfonyl, N,N-ethylmethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-propylmethylaminosulfonyl, N,N-isopropylmethylaminosulfonyl, N,N-tert-butylmethylaminosulfonyl, N,N-butylethylaminosulfonyl and other N,N-disubstituted aminosulfonyl groups; etc.

[0076] As R 12Examples of alkane dimethyl groups with 1 to 10 carbon atoms include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, isopropylene, isobutylene, 2-methyltrimethylene, isopentylene, isohexylene, isooctylene, and 2-ethylhexylene. Among these, alkane dimethyl groups with 1 to 6 carbon atoms are preferred, and alkane dimethyl groups with 1 to 4 carbon atoms are more preferred.

[0077] R 12 The -CH2- group in the alkane dimethyl group can be represented by -O-, -CO-, or -NR. 8 Replace with -, -OCO-, -COO-, -OCONH-, -CONH-, or -NHCO-.

[0078] As R 13 Alkyl groups having 1 to 4 carbon atoms are represented, for example, methyl, ethyl, propyl, and butyl.

[0079] As R 13 The alkoxy group represents alkoxy groups with 1 to 4 carbon atoms, for example, methoxy, ethoxy, propoxy, tert-butoxy, etc.

[0080] R 13 Preferably, it is methyl, ethyl, methoxy, or ethoxy, and more preferably methoxy or ethoxy.

[0081] As R 1 With R 2 R 3 With R 4 R 9 With R 10 The following structures illustrate the formation of nitrogen-containing rings. In the following structures, * indicates a connecting bond.

[0082]

[0083] R 1 ~R 4 Preferably, each group is a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 30 carbon atoms that may have substituents. More preferably, each group is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 30 carbon atoms that may have substituents. Even more preferably, each group is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents.

[0084] In particular, R is preferred. 1 and R 4 Each independently represents an aromatic hydrocarbon group with 6 to 30 carbon atoms that may have substituents, and R 2 and R3 Each can independently represent a hydrogen atom or a saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, more preferably R. 1 and R 4 Each independently represents an aromatic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, and R 2 and R 3 Each of the following independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms that may have substituents, with R being more preferred. 1 and R 4 Each independently represents an alkylphenyl group having 7 to 20 carbon atoms that may have substituents, and R 2 and R 3 Each can independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms that may have substituents.

[0085] R 9 and R 10 Each of the components is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a branched alkyl group having 3 to 10 carbon atoms, and even more preferably a hydrogen atom or a 2-ethylhexyl group. In particular, R is preferred. 9 It is a hydrogen atom, and R 10 It is an alkyl group having 1 to 10 carbon atoms, more preferably R. 9 It is a hydrogen atom, and R 10 It is a branched alkyl group having 3 to 10 carbon atoms, with R being more preferred. 9 It is a hydrogen atom, and R 10 It is 2-ethylhexyl.

[0086] As R 6 ~R 7 Alkyl groups having 1 to 6 carbon atoms are represented, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.

[0087] R 6 ~R 7 Each of the atoms is preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom.

[0088] R 5 Preferred types are -CO2H and -CO2. - Z + -CO2R 8 -SO3 - -SO3 - Z + -SO3H, -SO2NR 9 R 10 More preferably -SO3 - -SO3 - Z + -SO3H, -SO2NR9 R 10 Further preferred is -SO3 - -SO3 - Z + More preferably -SO3 - .

[0089] m is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0090] R 5 The bonding position is not particularly limited, but it is preferable to bond to at least one of two bonding positions adjacent to the pyrite skeleton, and more preferably to one of the two bonding positions adjacent to the pyrite skeleton. Furthermore, when m is 2 or more, it is preferable to bond to at least one of the two bonding positions adjacent to the pyrite skeleton and to a corresponding bonding position, and more preferably to bond to one of the two bonding positions adjacent to the pyrite skeleton and to a corresponding bonding position.

[0091] Examples of halogen atoms represented by X include fluorine, chlorine, bromine, and iodine atoms.

[0092] In formula (1), the ionic form of -SO3 - The number is preferably 0 or 1, more preferably 1.

[0093] a represents 0 or 1, preferably 0.

[0094] The compound represented by formula (1) is preferably electrically neutral. That is, the compound represented by formula (1) has one ionic form of -SO3. - In this case, a is preferably 0, and the compound represented by formula (1) does not have the ionic form of -SO3. - In this case, a is preferably 1.

[0095] The compound represented by formula (1) preferably has one or more ions selected from -SO3. - -SO3H, -SO3 - Z + and -SO2NR 9 R 10 The group comprising the group preferably has 1 to 4 groups, and more preferably 1 to 2 groups.

[0096] The preferred embodiment of the thallium pigment includes the compound represented by formula (1-A). The compound represented by formula (1-A) may be its tautomer.

[0097]

[0098] In formula (1-A),

[0099] R 21 and R 22 Each can independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms that may have substituents.

[0100] R 23 and R 24 Each can independently represent an alkyl group with 1 to 4 carbon atoms, an aromatic hydrocarbon group with 6 to 10 carbon atoms, or -SO3. - -SO3H, -SO3 - Z + 、or -SO2NR 29 R 30 .

[0101] p and q each independently represent integers from 0 to 5. When p is 2 or higher, multiple R... 23 They can be the same or different; when q is 2 or higher, multiple Rs... 24 They can be the same or different.

[0102] R 25 Indicates -SO3 - -SO3H, -SO3 - Z + 、or -SO2NR 29 R 30 .

[0103] R 29 and R 30 Each can be independently represented by an alkyl group having 1 to 10 hydrogen or carbon atoms.

[0104] a, m, X, and Z + Same as above.

[0105] In equation (1-A), a, m, X, and Z + With a, m, X, and Z in equation (1) + The same applies to their preferred methods.

[0106] As R 21 ~R 22 and R 29 ~R 30 The alkyl group refers to alkyl groups with 1 to 10 carbon atoms. Specifically, examples include straight-chain or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, isobutyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl.

[0107] R 21 and R 22 The alkyl group representing 1 to 10 carbon atoms may have substituents; examples of such substituents include those related to R.1 ~R 4 The saturated hydrocarbon group representing 1 to 20 carbon atoms may have the same substituents. Preferably, these are halogen atoms, hydroxyl groups, or carboxyl groups, and more preferably carboxyl groups.

[0108] R 21 and R 22 Each of the components is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms and a carboxyl group, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms and a carboxyl group, and even more preferably a hydrogen atom or an alkyl group having 2 to 4 carbon atoms and a carboxyl group.

[0109] R 29 and R 30 Each of the components is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a branched alkyl group having 3 to 10 carbon atoms, and even more preferably a hydrogen atom or a 2-ethylhexyl group. In particular, R is preferred. 29 It is a hydrogen atom, and R 30 It is an alkyl group having 1 to 10 carbon atoms, more preferably R. 29 It is a hydrogen atom, and R 30 It is a branched alkyl group having 3 to 10 carbon atoms, with R being more preferred. 29 It is a hydrogen atom, and R 30 It is 2-ethylhexyl.

[0110] As R 23 and R 24 The alkyl group representing 1 to 4 carbon atoms includes, for example, straight-chain or branched alkyl groups such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, and tert-butyl, with alkyl groups having 1 to 2 carbon atoms being preferred, and methyl being more preferred.

[0111] As R 23 and R 24 The aromatic hydrocarbon group representing 6 to 10 carbon atoms can be phenyl; tolyl, xylyl, mesitylene, propylphenyl, butylphenyl and other alkylphenyl groups, etc., with phenyl being preferred.

[0112] R 23 and R 24 Each of the components is preferably an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and even more preferably methyl or phenyl.

[0113] Regarding R 23 and R 24 Regarding the bonding position, it is preferable to bond to at least one of two bonding positions that are adjacent to N, and more preferably to bond to two bonding positions that are adjacent to N.

[0114] p and q are each preferably integers from 0 to 3, more preferably integers from 1 to 3, even more preferably integers from 1 to 2, and especially preferably 2.

[0115] R 25 Especially preferred is -SO3 - .

[0116] In formula (1-A), the ionic form of -SO3 - The number is preferably 0 or 1, more preferably 1.

[0117] The compound represented by formula (1-A) is preferably electrically neutral. That is, it has one ionic form, -SO3. - In this case, a is preferably 0, and the compound represented by formula (1-A) does not have the ionic form of -SO3. - In this case, a is preferably 1.

[0118] The compound represented by formula (1-A) preferably has one or more ions selected from -SO3 - -SO3H, -SO3 - Z + and -SO2NR 9 R 10 The group comprising the group preferably has 1 to 4 groups, and more preferably 1 or 2 groups.

[0119] Examples of succinate pigments include compounds represented by formulas (1-1) to (1-54). It should be noted that in the following formulas, Ra represents 2-ethylhexyl.

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] Other examples of pigments include those described in Japanese Patent Application Publication No. 2017-194551.

[0127] The preferred compound is a compound represented by formula (1-17) to formula (1-32), more preferably a compound represented by formula (1-17) to formula (1-28) and formula (1-32), and even more preferably a compound represented by formula (1-32).

[0128] It should be noted that the colorant may contain one or more pyrithione pigments.

[0129] The colorant (A) comprises at least one selected from the group consisting of red pigment and orange pigment, preferably comprising at least orange pigment, and more preferably comprising both red pigment and orange pigment.

[0130] As red and orange pigments, for example:

[0131] CI pigments include orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments;

[0132] CI pigments include red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 272, 273, 291, 297, etc.

[0133] etc.

[0134] Red and orange pigments preferably comprise pigments having one or more skeletons selected from the group consisting of a pyrrolopyrrole dione skeleton and an azo skeleton. Red pigments more preferably comprise pigments having a pyrrolopyrrole dione skeleton. Orange pigments more preferably comprise pigments having an azo skeleton.

[0135] As a pigment having a pyrrolopyrrole dione skeleton, the compound represented by formula (i) is preferred.

[0136]

[0137] In formula (i),

[0138] R 1 ~R 10 Each can independently represent a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group with 1 to 15 carbon atoms, or -OR. 11 -SR 11 -SO3M, -SO2NHR 11 -SO2N(R) 12 )2、-N(R 11 )2.

[0139] R 11 A hydrocarbon group representing 1 to 15 hydrogen or carbon atoms.

[0140] R 12 Represents hydrocarbon groups with 1 to 15 carbon atoms.

[0141] M represents a hydrogen atom or an alkali metal atom.

[0142] The halogen atom is preferably a fluorine atom, chlorine atom, bromine atom, or iodine atom, more preferably a fluorine atom, chlorine atom, or bromine atom, and even more preferably a chlorine atom or bromine atom.

[0143] R 1 ~R 10 The hydrocarbon groups representing 1 to 15 carbon atoms can be saturated or unsaturated, preferably aliphatic hydrocarbon groups and aromatic hydrocarbon groups, and also preferably a combination of aliphatic hydrocarbon groups and aromatic hydrocarbon groups.

[0144] The aliphatic hydrocarbon group is preferably a straight-chain or branched alkyl group. Specifically, examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, octadecyl, 1,5-dimethylhexyl, 1,6-dimethylheptyl, 2-ethylhexyl, etc.

[0145] The aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms, more preferably 1 to 10, even more preferably 1 to 8, even more preferably 1 to 6, and especially preferably 1 to 3.

[0146] The aromatic hydrocarbon group is preferably phenyl; tolyl, xylyl, mesitylene, propylphenyl, butylphenyl and other alkylphenyl groups, more preferably phenyl.

[0147] 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.

[0148] The aromatic hydrocarbon group can be substituted and can have substituents such as trifluoromethyl, halogen atom, nitro, cyano, carbamoyl, aminosulfonyl, alkoxy with 1 to 4 carbon atoms, etc. The aromatic hydrocarbon group with substituents is preferably p-methylphenyl, 4-tert-butylphenyl, p-nitrophenyl, p-methoxyphenyl, p-chlorophenyl, 2,4-dichlorophenyl, or 3-carbamoylphenyl.

[0149] The combination of aliphatic and aromatic hydrocarbon groups is preferably aralkyl groups such as benzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 4-methoxybenzyl, 4-nitrobenzyl, and 2,4-dichlorobenzyl.

[0150] R 11 and R 12Hydrocarbon groups representing 1 to 15 carbon atoms can be combined with R 1 ~R 10 The hydrocarbon groups representing 1 to 15 carbon atoms are the same, and the preferred range can also be the same.

[0151] As -OR 11 Examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, 2-ethylhexoxy, and eicosyloxy.

[0152] As -SR 11 Examples include methyl thio, ethyl thio, butyl thio, hexyl thio, decyl thio, and eicosyl thio.

[0153] As -SO2NHR 11 Examples include:

[0154] Aminosulfonyl;

[0155] N-Methylaminosulfonyl, N-ethylaminosulfonyl, N-propylaminosulfonyl, N-isopropylaminosulfonyl, N-butylaminosulfonyl, N-isobutylaminosulfonyl, N-sec-butylaminosulfonyl, N-tert-butylaminosulfonyl, N-pentylaminosulfonyl, N-(1-ethylpropyl)aminosulfonyl, N-(1,1-dimethylpropyl)aminosulfonyl, N-(1,2-dimethylpropyl)aminosulfonyl, N-(2,2-dimethylpropyl)aminosulfonyl, N-(1-methylbutyl)aminosulfonyl, N-(2-methylbutyl)aminosulfonyl, N -(3-methylbutyl)aminosulfonyl, N-cyclopentylaminosulfonyl, N-hexylaminosulfonyl, N-(1,3-dimethylbutyl)aminosulfonyl, N-(3,3-dimethylbutyl)aminosulfonyl, N-heptylaminosulfonyl, N-(1-methylhexyl)aminosulfonyl, N-(1,4-dimethylpentyl)aminosulfonyl, N-octylaminosulfonyl, N-(2-ethylhexyl)aminosulfonyl, N-(1,5-dimethyl)hexylaminosulfonyl, N-(1,1,2,2-tetramethylbutyl)aminosulfonyl and other N-monosubstituted aminosulfonyl groups;

[0156] As -SO2N(R 12 )2, Examples include N,N-dimethylaminosulfonyl, N,N-ethylmethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-propylmethylaminosulfonyl, N,N-isopropylmethylaminosulfonyl, N,N-tert-butylmethylaminosulfonyl, N,N-butylethylaminosulfonyl, N,N-bis(1-methylpropyl)aminosulfonyl, N,N-heptylmethylaminosulfonyl, and other N,N-disubstituted aminosulfonyl groups; etc.

[0157] As -N(R) 11 )2, examples can be given:

[0158] amino;

[0159] Monosubstituted amino groups such as N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-(sec-butyl)amino, N-(tert-butyl)amino, N-pentylamino, N-(1-ethylpropyl)amino, N-hexylamino, N-(2-ethylhexyl)amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, and N-phenylamino;

[0160] N,N-Dimethylamino, N-Ethyl-N-Methylamino, N,N-Diethylamino, N-Propyl-N-Methylamino, N,N-Dipropylamino, N-Isopropyl-N-Methylamino, N,N-Diisopropylamino, N,N-Diisobutylamino, N,N-Di(sec-butyl)amino, N-(tert-butyl)-N-Methylamino, N,N-Di(tert-butyl)amino, N-Butyl-N-Methylamino, N,N-Dibutylamino, N-Butyl-N- Disubstituted amino groups such as octylamino, N,N-dipentylamino, N,N-bis(1-ethylpropyl)amino, N-butyl-N-hexylamino, N-hexyl-N-methylamino, N,N-dihexylamino, N-(2-ethylhexyl)-N-methylamino, N,N-bis(2-ethylhexyl)amino, N,N-diheptylamino, N-octyl-N-methylamino, N,N-dioctylamino, N-phenyl-N-methylamino, and N,N-diphenylamino.

[0161] The alkali metal atom represented by M in -SO3M is preferably sodium or potassium.

[0162] Among them, R 1 ~R 10 Each of the groups is preferably represented by a hydrogen atom, a halogen atom, a cyano group, and a hydrocarbon group having 1 to 15 carbon atoms, and more preferably by a hydrocarbon group having 1 to 10 hydrogen atoms, a halogen atom, and a hydrocarbon group having 1 to 10 carbon atoms.

[0163] In the preferred method, R is preferred. 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 a halogen atom or a hydrocarbon group having 1 to 15 carbon atoms, more preferably 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 a halogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and R is further preferred. 1 ~R 5At least one of them is a halogen atom or an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 10 carbon atoms, and R 6 ~R 10 At least one of them is a halogen atom or an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 10 carbon atoms. When 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 can be the same or different.

[0164] The compound represented by formula (i) is more preferably the compound represented by formula (i-1).

[0165]

[0166] In equation (i-1),

[0167] R 3 and R 8 Each can independently represent a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group with 1 to 15 carbon atoms, or -OR. 11 -SR 11 -SO3M, -SO2NHR 11 -SO2N(R) 12 )2、-N(R 11 )2.

[0168] R 11 A hydrocarbon group representing 1 to 15 hydrogen or carbon atoms.

[0169] R 12 Represents hydrocarbon groups with 1 to 15 carbon atoms.

[0170] M represents a hydrogen atom or an alkali metal atom.

[0171] R 3 R 8 R 11 R 12 M is the same as in the above text.

[0172] In equation (i) or equation (i-1), R 3 and R 8 Each halogen atom or hydrocarbon group having 1 to 15 carbon atoms is preferred, more preferably an aliphatic or aromatic hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a chlorine atom, bromine atom, a straight-chain alkyl group having 1 to 10 carbon atoms, or a phenyl group. When there are multiple halogen atoms or hydrocarbon groups, the halogen atoms or hydrocarbon groups can be the same or different.

[0173] The compounds represented by formula (i) or formula (i-1) are preferably CI Pigment Red 254, CI Pigment Red 272, CI Pigment Red 291, etc.

[0174] As pigments having an azo skeleton, compounds represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and compounds represented by formula (II) (hereinafter, sometimes referred to as compound (II)) are preferred.

[0175] The following describes compound (I) in detail, but compound (I) also includes the resonance structure of formula (I), the tautomer of formula (I), and compounds obtained by rotating the groups in formula (I) about the bond axis of the single bond.

[0176]

[0177] In formula (I),

[0178] X 1 Represents a hydrogen atom, an aliphatic hydrocarbon group that may have substituents, an aromatic hydrocarbon group that may have substituents, a heterocyclic group that may have substituents, or -CONR. 5 R 6 .

[0179] X 2 Represents hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms that may have substituents, and -OR. 1 、or -COOR 2 .

[0180] X 3 Represents halogen atoms, cyano groups, nitro groups, hydrocarbon groups with 1 to 20 carbon atoms that may have substituents, and -OR. 3 -COOR 4 -CONR 5 R 6 、or -SO2NR 7 R 8 .

[0181] R 1 ~R 8 Each group can be a hydrogen atom or a hydrocarbon group with 1 to 20 carbon atoms, representing a hydrogen atom or a hydrocarbon group that can be represented independently.

[0182] l represents an integer from 0 to 4.

[0183] n represents 1 or 2,

[0184] m represents any integer from 0 to 5.

[0185] The sum of m and n is an integer less than or equal to 6.

[0186] X 1 X 2 、 or X 3 If multiple instances exist, they can be the same or different.

[0187] X 1The aliphatic hydrocarbon group can be saturated or unsaturated, and can be chain-like or cyclic (alicyclic hydrocarbon group).

[0188] Examples of saturated or unsaturated chain hydrocarbon groups include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0189] Isopropyl, Isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl 4-Methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butylhexyl, etc., are branched alkyl groups;

[0190] Vinyl group, propenyl (e.g., 1-propenyl, 2-propenyl(allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1-(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,2-dimethyl-1-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, ... 4-Pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, and other alkenyl groups;

[0191] Acynyl, propynyl (e.g., 1-propynyl, 2-propynyl), octyynyl (e.g., 1-octyynyl, 7-octyynyl), butynyl, pentyynyl, hexynyl, hepynyl, nonynyl, decyynyl, undecynyl, dodecyynyl, and other ynylyl groups;

[0192] etc.

[0193] The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 12, and particularly preferably 1 to 9. Among these, straight-chain or branched alkyl groups with 1 to 9 carbon atoms are particularly preferred.

[0194] Examples of saturated or unsaturated alicyclic hydrocarbon groups include: cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3... Cycloalkyl groups such as 4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, and 4,4-dimethylcyclohexyl; cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl, and cyclooctenyl; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornyl, adamantyl, and bicyclo[2.2.2]octyl; etc.

[0195] 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 especially preferably 3 to 12.

[0196] As X 1 Examples of aromatic hydrocarbon groups that can be represented include: phenyl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, biphenyl, and other aryl groups; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-6-ethylphenyl, 2,6-diethylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2-methyl-6-isopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, and other alkylaryl groups; 4-vinylphenyl and other alkenylaryl groups; and so on.

[0197] X 1 The aromatic hydrocarbon group represented preferably has 6 to 20 carbon atoms, more preferably 6 to 18, even more preferably 6 to 12, and even more preferably 6 to 10.

[0198] X 1 The heterocyclic group can be monocyclic or polycyclic, and can be either saturated or unsaturated. As X 1The heterocyclic group represented is preferably a heterocyclic group that includes heteroatoms other than carbon atoms as constituent elements of the ring. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms.

[0199] X 1 The number of carbon atoms in the heterocyclic group is preferably 2 to 20, more preferably 3 to 18, and even more preferably 3 to 15.

[0200] Examples of heterocyclic groups containing only nitrogen atoms as heteroatoms include: monocyclic heterocyclic groups such as pyrroloyl, imidazoyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridylylene, piperidinyl, and piperazinyl; polycyclic heterocyclic groups such as indoleazinyl, indoleyl, 1H-indazoleyl, isoquinolinyl, quinolinyl, phthalazinyl, carbazoleyl, acridineyl, indolelinyl, and isoindolinyl; and so on.

[0201] Examples of heterocyclic groups that contain only oxygen atoms as heteroatoms include: monocyclic heterocyclic groups such as furanyl and pyranyl; polycyclic heterocyclic groups such as isobenzofuranyl, benzopyranyl, xanthanyl, and chromanyl; and so on.

[0202] Examples of heterocyclic groups that contain only sulfur atoms as heteroatoms include: monocyclic heterocyclic groups such as thienyl; polycyclic heterocyclic groups such as benzo[b]thienyl and thianthyl; and so on.

[0203] Examples of heterocyclic groups that include nitrogen and oxygen atoms as heteroatoms include: monocyclic heterocyclic groups such as oxazolyl; polycyclic heterocyclic groups such as benzimidazolone; and so on.

[0204] As X 1 The heterocyclic group represented is preferably a polycyclic heterocyclic group, more preferably a polycyclic heterocyclic group having a benzene ring, such as benzo[b]thiophene, thiaanthryl, isobenzofuranyl, benzopyranyl, xanthonyl, indolyl, 1H-indazoleyl, isoquinolinyl, quinolinyl, phthalazinyl, carbazoleyl, acridineyl, chromanyl, indololinyl, isoindololinyl, benzimidazoloneyl, etc.

[0205] X 1 -CONR 5 R 6Examples include: carbamoyl; N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N-phenylcarbamoyl, etc., all N-monosubstituted carbamoyl groups; N,N-dimethylcarbamoyl, N,N-ethylmethylcarbamoyl, N,N-diethyl... Carbamoyl, N,N-propylmethylcarbamoyl, N,N-dipropylcarbamoyl, N,N-isopropylmethylcarbamoyl, N,N-diisopropylcarbamoyl, N,N-tert-butylmethylcarbamoyl, N,N-diisobutylcarbamoyl, N,N-disec-butylcarbamoyl, N,N-ditert-butylcarbamoyl, N,N-butylmethylcarbamoyl, N,N-diphenylcarbamoyl, and other N,N-disubstituted carbamoyl groups.

[0206] As X 2 X 3 and R 1 ~R 8 The hydrocarbon group represented can be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. Aliphatic hydrocarbon groups can be saturated or unsaturated, and can be chain-like or alicyclic.

[0207] Examples of saturated or unsaturated chain hydrocarbon groups include: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecanyl, n-eicosyl, etc., which are straight-chain alkyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)propyl, etc. Branched alkyl groups such as (1-propyl)pentyl, (1-butyl)pentyl, isohexyl, (2-methyl)hexyl, (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (2-methyl)octyl, (2-ethyl)octyl, etc.; vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, 2-pentenyl, etc.; etc.

[0208] Examples of saturated or unsaturated alicyclic hydrocarbon groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and other cycloalkyl groups; cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and other cycloalkenyl groups; norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc.

[0209] As an aromatic hydrocarbon group, examples can be given related to X mentioned above. 1 The same group represents an aromatic hydrocarbon group.

[0210] Regarding the aforementioned hydrocarbon groups with 1 to 20 carbon atoms, these can be groups composed of two or more groups selected from the group consisting of chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups mentioned above, provided that the upper limit for the number of carbon atoms is 20. Examples of such groups include: benzyl, phenethyl, 1-methyl-1-phenylethyl, and other arylalkyl groups; phenyl vinyl and other arylalylene groups; phenyl ethynyl and other arylynyl groups; 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl... Cyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, and other alicyclic hydrocarbon groups bonded with one or more alkyl or alicyclic hydrocarbon groups; alkyl groups bonded with one or more alicyclic hydrocarbon groups, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl; etc.

[0211] As X 1 The aliphatic hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, and X are represented. 2 The hydrocarbon group and X are represented. 3 The substituents that the hydrocarbon group may have include halogen atoms, hydroxyl groups, alkoxy groups, alkyl thio 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 aminosulfonyl groups, -SO3M, etc. The aforementioned M represents a hydrogen atom or an alkali metal atom (e.g., sodium, potassium).

[0212] Regarding aliphatic hydrocarbon groups with halogen atoms as substituents, examples can be found in X. 1 The group represented is an aliphatic hydrocarbon group bonded with a halogen atom. Examples include trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-dibromoethyl, 2,2,3,3-tetrafluoropropyl, pentafluoroethyl, heptafluoropropyl, and other chain alkyl groups.

[0213] Regarding aromatic hydrocarbon groups with halogen atoms as substituents, examples can be found in X. 1The aromatic hydrocarbon group to which the halogen atom is bonded can be represented, for example, aryl groups such as 4-bromophenyl, 2,4-dichlorophenyl, pentafluorophenyl, 2-methyl-4-chlorophenyl, and 4,5,8-trichloro-2-naphthyl.

[0214] Regarding heterocyclic groups with halogen atoms as substituents, examples can be found in X. 1 This indicates a group to which a halogen atom is bonded to a heterocyclic group.

[0215] Examples of combinations of aromatic and aliphatic hydrocarbon groups with halogen atoms as substituents include (2,4-dichlorophenyl)methyl, (4-fluorophenyl)methyl, (3,5-difluorophenyl)methyl, 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl, (phenoxy)(phenyl)methyl, and (benzyloxy)(phenyl)methyl.

[0216] Regarding the alkoxy group as a substituent, examples include methoxy, ethoxy, propoxy, n-butoxy, tert-butoxy, etc. The aforementioned alkoxy group preferably has 1 to 4 carbon atoms, more preferably 1 or 2.

[0217] Examples of alkyl thio groups that can be used as substituents include methyl thio, ethyl thio, propyl thio, and n-butyl thio. The number of carbon atoms in the aforementioned alkyl thio groups is preferably 1 to 4, more preferably 1 or 2.

[0218] Regarding the substituted amino group as a substituent, examples include amino groups having one or two hydrocarbon groups. Examples of such hydrocarbon groups, as described above, that have 1 to 20 carbon atoms, are preferably alkyl groups with 1 to 4 carbon atoms or aromatic hydrocarbon groups with 6 to 10 carbon atoms. Examples of substituted amino groups include, for example, N-monosubstituted amino groups such as N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, and N-phenylamino; and N,N-disubstituted amino groups such as N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-diisopropylamino, N,N-diphenylamino, N,N-ethylmethylamino, N,N-methylphenylamino, and N,N-ethylphenylamino.

[0219] The N-acylamino group used as a substituent refers to the group consisting of -NHCOR. 9a The group represented by R 9a Represents a hydrogen atom or a hydrocarbon group. As R... 9a The hydrocarbon group represented can be exemplified by the groups described above that have 1 to 20 carbon atoms. As R 9a Preferably, it 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, N-acetylamino, N-propionylamino, N-butyrylamino, and N-benzoylamino.

[0220] The term "substituted or unsubstituted carbamoyl group" as a substituent refers to the carbamoyl group formed by -CONR. 9b R 9c The group represented by R 9b R 9c Each can be represented independently by a hydrogen atom or a hydrocarbon group. As R 9b R 9c The hydrocarbon group represented can be exemplified by the groups described above that have 1 to 20 carbon atoms. As R 9b R 9c Preferably, each group is independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. As -CONR 9b R 9c Examples include: carbamoyl; N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-tert-butylcarbamoyl, N-phenylcarbamoyl, etc., all N-monosubstituted carbamoyl groups; N,N-dimethylcarbamoyl, N,N-ethylmethylcarbamoyl, N,N-diethylcarbamoyl, N,N-propylmethylcarbamoyl, N,N-dipropylcarbamoyl, N,N-butylmethylcarbamoyl, N,N-tert-butylmethylcarbamoyl, N,N-ditert-butylcarbamoyl, N,N-phenylmethylcarbamoyl, N,N-diphenylcarbamoyl, etc., all N,N-disubstituted carbamoyl groups.

[0221] The substituted or unsubstituted aminosulfonyl group as a substituent refers to -SO2NR 9d R 9e The group represented by R 9d R 9e Each can be represented independently by a hydrogen atom or a hydrocarbon group. As R 9d R 9e The hydrocarbon group represented can be exemplified by the groups described above that have 1 to 20 carbon atoms. As R 9d R 9e Preferably, each group is independently composed of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. As -SO2NR 9d R 9eExamples include: aminosulfonyl; N-methylaminosulfonyl, N-ethylaminosulfonyl, N-propylaminosulfonyl, N-isopropylaminosulfonyl, N-butylaminosulfonyl, N-isobutylaminosulfonyl and other N-monosubstituted aminosulfonyl groups; N,N-dimethylaminosulfonyl, N,N-ethylmethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-propylmethylaminosulfonyl, N,N-isopropylmethylaminosulfonyl, N,N-tert-butylmethylaminosulfonyl, N,N-butylethylaminosulfonyl, N,N-dibutylaminosulfonyl and other N,N-disubstituted aminosulfonyl groups.

[0222] As X 2 -OR 1 and X 3 -OR 3 For example, examples include: hydroxyl; methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, and other alkoxy groups; and so on.

[0223] As X 2 -COOR 2 and X 3 -COOR 4 For example, examples include: carboxyl groups; methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, and other alkoxycarbonyl groups; and so on.

[0224] As X 3 -CONR 5 R 6 Examples include: carbamoyl; N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, etc., N-monosubstituted carbamoyl groups; N,N-dimethylcarbamoyl, N,N-ethylmethylcarbamoyl, N,N- Diethylcarbamoyl, N,N-propylmethylcarbamoyl, N,N-dipropylcarbamoyl, N,N-isopropylmethylcarbamoyl, N,N-diisopropylcarbamoyl, N,N-tert-butylmethylcarbamoyl, N,N-diisobutylcarbamoyl, N,N-disec-butylcarbamoyl, N,N-ditert-butylcarbamoyl, N,N-butylmethylcarbamoyl and other N,N-disubstituted carbamoyl groups.

[0225] As X 3 -SO2NR 7 R 8Examples include: aminosulfonyl; N-methylaminosulfonyl, N-ethylaminosulfonyl, N-propylaminosulfonyl, N-isopropylaminosulfonyl, N-butylaminosulfonyl, N-isobutylaminosulfonyl, N-pentylaminosulfonyl, N-(1-ethylpropyl)aminosulfonyl, N-(1,1-dimethylpropyl)aminosulfonyl, N-cyclopentylaminosulfonyl, N-hexylaminosulfonyl, etc., all N-monosubstituted aminosulfonyl groups. Acyl group; N,N-dimethylaminosulfonyl, N,N-ethylmethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-propylmethylaminosulfonyl, N,N-isopropylmethylaminosulfonyl, N,N-tert-butylmethylaminosulfonyl, N,N-butylethylaminosulfonyl, N,N-bis(1-methylpropyl)aminosulfonyl, N,N-heptylmethylaminosulfonyl, etc. N,N-disubstituted aminosulfonyl groups.

[0226] About X 2 and X 3 Examples of halogen atoms, including fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, may be represented by halogen atoms, chlorine atoms, or bromine atoms, and more preferably fluorine atoms or chlorine atoms.

[0227] 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.

[0228] n represents 1 or 2, m represents any integer from 0 to 5, and the sum of m and n is an integer less than 6.

[0229] As X 1 Preferably, it is a hydrogen atom, an aliphatic hydrocarbon group that may have substituents, or -CONR. 5 R 6 More preferably, it is a hydrogen atom, a chain alkyl group that may have substituents, or a -CONR group. 5 R 6 More preferably, hydrogen atoms, or chain alkyl groups having 1 to 6 carbon atoms and substituents, or -CONR. 5 R 6 .

[0230] -CONR 5 R 6 R in 5 and R 6 Preferably, it is a hydrocarbon group with 1 to 15 hydrogen atoms and carbon atoms, more preferably an aliphatic hydrocarbon group with 1 to 10 hydrogen atoms or an aromatic hydrocarbon group with 6 to 10 carbon atoms.

[0231] As X 2 Preferably, it is a hydrogen atom, a halogen atom, a hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or -OR 1More preferably, it is a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms that may have a substituent, or an alkoxy group having 1 to 20 carbon atoms; even more preferably, it is a hydrogen atom, a halogen atom, a chain hydrocarbon group having 1 to 10 carbon atoms that may have a substituent, or an alkoxy group having 1 to 10 carbon atoms; even more preferably, it is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms that may have a substituent, or an alkoxy group having 1 to 4 carbon atoms; even more preferably, it is an alkyl group having 1 to 4 carbon atoms, a halogen atom, or an alkoxy group having 1 to 4 carbon atoms; even more preferably, it is a halogen atom or an alkoxy group having 1 to 4 carbon atoms.

[0232] As X 3 Preferably, it contains halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms that may have substituents, and -OR. 3 -CONR 5 R 6 、or -SO2NR 7 R 8 More preferably, it is a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms that may have substituents, or -OR 3 Further preferred are halogen atoms, chain hydrocarbon groups having 1 to 10 carbon atoms that may have substituents, or alkoxy groups having 1 to 20 carbon atoms; even more preferred are halogen atoms, alkyl groups having 1 to 4 carbon atoms that may have substituents, or alkoxy groups having 1 to 10 carbon atoms; further preferred are fluorine atoms, chlorine atoms, bromine atoms, alkyl groups having 1 to 4 carbon atoms that have halogen atoms as substituents, or alkoxy groups having 1 to 4 carbon atoms; even more preferred are fluorine atoms, chlorine atoms, fluoroalkyl groups having 1 to 4 carbon atoms (especially perfluoroalkyl groups), or alkoxy groups having 1 to 4 carbon atoms; even more preferred are chlorine atoms, trifluoromethyl groups, or alkoxy groups having 1 to 4 carbon atoms.

[0233] n can be 1 or 2, preferably 1.

[0234] m is any integer from 0 to 5, preferably any integer from 0 to 2, more preferably 0 or 2, and even more preferably 2.

[0235] When m is 2, there are 2 X 3 It can be bonded to any position that is adjacent, intermediate, or opposite, preferably to a position that is intermediate or opposite, and more preferably to a position that is opposite.

[0236] Examples of compounds (I) include CI pigment reds 242 and 269, azo pigments described in Japanese Patent Application Publication No. 2013-161026, and azo pigments described in Japanese Patent Application Publication No. 2017-142503.

[0237] As a method for producing compound (I), known methods can be employed.

[0238] Orange pigments preferably contain compound (II).

[0239] The following describes compound (II) in detail, but compound (II) also includes the resonance structure of formula (II), the tautomer of formula (II), and compounds obtained by rotating the groups in formula (II) around the bond axis of the single bond.

[0240]

[0241] In formula (II),

[0242] L 1 This indicates a divalent aromatic hydrocarbon group that may have substituents.

[0243] X 11 ~X 14 A hydrocarbon group, which can independently represent a hydrogen atom or have 1 to 20 carbon atoms and may have substituents.

[0244] The so-called L 1 The term "divalent aromatic hydrocarbon group" refers to a group formed in an aromatic hydrocarbon ring where the two hydrogen atoms directly bonded to the carbon atoms constituting the ring are replaced by linking bonds. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group can be any monocyclic or polycyclic ring; examples include benzene rings, biphenyl rings, naphthalene rings, anthracene rings, and structures formed by replacing at least one hydrogen atom with a hydrocarbon group in these aromatic hydrocarbon rings. Examples of the aforementioned hydrocarbon groups include those related to X described above. 2 X 3 and R 1 ~R 8 The same group representing a hydrocarbon group with 1 to 20 carbon atoms is preferably a hydrocarbon group with 1 to 12 carbon atoms, more preferably a chain hydrocarbon group with 1 to 10 carbon atoms, or an aromatic hydrocarbon group with 6 to 12 carbon atoms, even more preferably a chain hydrocarbon group with 1 to 10 carbon atoms, and even more preferably a saturated chain hydrocarbon group with 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.

[0245] As X 11 ~X 14 The hydrocarbon group represented can be exemplified by X mentioned above. 2 X 3 and R 1 ~R 8 The same group represents hydrocarbon groups with 1 to 20 carbon atoms.

[0246] As L 1 The divalent aromatic hydrocarbon group and X represent11 ~X 14 The hydrocarbon group represented may have substituents, and examples of substituents related to X mentioned above can be given. 1 The aromatic hydrocarbon group and heterocyclic group represented by X 2 The hydrocarbon group and X are represented. 3 The hydrocarbon group represented may have the same substituents as the group.

[0247] As L 1 Preferably, it is a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms that may have substituents, more preferably a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents. As the aromatic hydrocarbon ring constituting the aforementioned divalent aromatic hydrocarbon group, it 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 structure in which at least one hydrogen atom of the 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 may be present in the aforementioned divalent aromatic hydrocarbon group are preferably halogen atoms, alkoxy groups, alkyl thio groups, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, and substituted or unsubstituted carbamoyl groups. More preferably, they are halogen atoms, alkoxy groups with 1 to 4 carbon atoms, alkyl thio groups with 1 to 4 carbon atoms, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, and substituted or unsubstituted carbamoyl groups. Even more preferably, they are halogen atoms, alkoxy groups with 1 to 4 carbon atoms, and cyano groups. Even more preferably, they are chlorine atoms, fluorine atoms, alkoxy groups with 1 to 4 carbon atoms, and cyano groups.

[0248] As L 1 Preferably, it is any one of the groups represented by formulas (ph1) to (ph16), more preferably any one of the groups represented by formulas (ph1) to (ph3) and (ph11) to (ph13), and even more preferably any one of the groups represented by formulas (ph11), (ph12), (ph11), and (ph12).

[0249]

[0250] [In equations (ph1) to (ph16), * and ** represent connecting keys.]

[0251] As X 11 X 13The components are preferably, independently, hydrogen atoms, alkyl groups having 1 to 10 carbon atoms that may have substituents, cycloalkyl groups having 3 to 10 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 12 carbon atoms that may have substituents; more preferably, alkyl groups having 1 to 10 carbon atoms that may have substituents, cycloalkyl groups having 3 to 10 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 12 carbon atoms that may have substituents; even more preferably, alkyl groups having 1 to 10 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 12 carbon atoms that may have substituents; even more preferably, alkyl groups having 1 to 4 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 10 carbon atoms that may have substituents; even more preferably, phenyl groups having substituents; and even more preferably, phenyl. As X 11 X 13 The substituents that the hydrocarbon group may have are preferably halogen atoms, alkoxy groups with 1 to 4 carbon atoms, alkyl thio groups with 1 to 4 carbon atoms, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, substituted or unsubstituted carbamoyl groups, more preferably halogen atoms, alkoxy groups with 1 to 4 carbon atoms, or cyano groups, even more preferably chlorine atoms, fluorine atoms, alkoxy groups with 1 to 4 carbon atoms, or cyano groups, and even more preferably chlorine atoms or fluorine atoms.

[0252] As X 12 X 14 The components are preferably, independently, hydrogen atoms, alkyl groups having 1 to 10 carbon atoms that may have substituents, cycloalkyl groups having 3 to 10 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 12 carbon atoms that may have substituents; more preferably, alkyl groups having 1 to 10 carbon atoms that may have substituents, cycloalkyl groups having 3 to 10 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 12 carbon atoms that may have substituents; even more preferably, alkyl groups having 1 to 10 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 12 carbon atoms that may have substituents; even more preferably, alkyl groups having 1 to 4 carbon atoms that may have substituents, or aromatic hydrocarbon groups having 6 to 10 carbon atoms that may have substituents; even more preferably, alkyl groups having 1 to 4 carbon atoms that may have substituents; even more preferably, alkyl groups having 1 or 2 carbon atoms that may have substituents; even more preferably, methyl or ethyl; and especially preferably, methyl. As X 12 X 14The substituents that the hydrocarbon group may have are preferably halogen atoms, alkoxy groups with 1 to 4 carbon atoms, alkyl thio groups with 1 to 4 carbon atoms, carboxyl groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, substituted or unsubstituted carbamoyl groups, more preferably halogen atoms, alkoxy groups with 1 to 4 carbon atoms, or cyano groups, even more preferably chlorine atoms, fluorine atoms, alkoxy groups with 1 to 4 carbon atoms, or cyano groups, and even more preferably chlorine atoms or fluorine atoms.

[0253] Examples of compounds (II) include, for example, pigment CI Orange 13 and the azo pigment described in International Publication No. 2022 / 065357.

[0254] As a method for producing compound (II), known methods can be employed.

[0255] The colorant (A) may contain colorants other than those described above. Other colorants (a1) may be any of dyes (hereinafter, sometimes referred to as dyes (a1-1)) and pigments (hereinafter, sometimes referred to as pigments (a1-2)).

[0256] There are no particular limitations on the dyes (a1-1), and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of dyes include compounds classified as dyes in color indexes (published by The Society of Dyers and Colourists) and known dyes listed in dyeing guides (for dyeing companies). Additionally, based on their chemical structures, examples include azo dyes, cyanide dyes, triarylmethane dyes, thiazole dyes, oxazine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylbenzene dyes, methylimine dyes, squaric acid onion dyes, acridine dyes, styrylyl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinoline ketone dyes, isoindoline dyes, etc.

[0257] As a dye (a1-1), specifically, examples include:

[0258] CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

[0259] CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;

[0260] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0261] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0262] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0263] CI solvent green dyes 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0264] CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 15 7, 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;

[0265] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 57, 66, 73, 76, 80, 88, 97, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 1 98, 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;

[0266] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0267] CI Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0268] Acid Blue (CI) 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;

[0269] CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50: 1, 58, 63, 65, 80, 104, 105, 106, 109, etc. CI acid dyes

[0270] 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;

[0271] 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;

[0272] CI direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0273] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0274] 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, 16 7, 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;

[0275] CI Direct Green includes CI direct dyes such as 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82.

[0276] CI Disperse Yellow 51, 54, 76;

[0277] CI Disperse Violet 26, 27;

[0278] CI disperse blue 1, 14, 56, 60 and other CI disperse dyes,

[0279] 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;

[0280] CI Basic Violet 2;

[0281] CI Basic Red 9;

[0282] CI Basic Green 1; and other CI basic dyes,

[0283] CI Active Yellow 2, 76, 116;

[0284] CI Active Orange 16;

[0285] CI Reactive Red 36; and other CI reactive dyes,

[0286] CI Media Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0287] CI Media 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;

[0288] CI Media Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0289] CI Media Purple 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;

[0290] CI Media 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;

[0291] CI mordant green dyes 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc.

[0292] CI vat green 1 and other CI vat dyes, etc.

[0293] These dyes (a1-1) can be used with one or more dyes for various colors, or a combination of dyes of various colors.

[0294] As pigments (a1-2), for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be cited.

[0295] As pigments classified as pigments (a4-2), specifically, examples include:

[0296] CI pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, 231, 235, 236, etc.

[0297] CI pigments include green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67, and other green pigments;

[0298] CI pigment blue 15, 15:3, 15:4, 15:6, 16 and other blue pigments;

[0299] CI pigments include purple 19, 23, 29, 32, 36, 38, and other purple pigments;

[0300] CI pigments, such as brown 23 and 25;

[0301] CI pigments include black 1, 7, 31, 32, and other black pigments; etc.

[0302] These pigments (a1-2) can be used with one or more pigments for various colors, or a combination of pigments of various colors.

[0303] At least one pigment selected from the group consisting of red and orange pigments, CI pigment yellow 185, and thallium pigment can be subjected to the following treatments as needed: rosin treatment; surface treatment using pigment derivatives with introduced acidic or basic groups; grafting treatment to the pigment surface using polymeric compounds; micronization treatment using sulfuric acid micronization; cleaning treatment using organic solvents, water, etc., to remove impurities; and removal treatment of ionic impurities using ion exchange, etc. The particle size of these colorants is preferably substantially uniform. Furthermore, by dispersing these colorants with a pigment dispersant, a colorant dispersion in a uniformly dispersed state in a pigment dispersant solution can be prepared. These colorants can be dispersed individually or in combination.

[0304] Examples of pigment dispersants include surfactants, which can be cationic, anionic, nonionic, or amphoteric. Specifically, examples include polyester-based, polyamine-based, and acrylic surfactants. These pigment dispersants can be used alone or in combination of two or more. Examples of pigment dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Corporation), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie Corporation).

[0305] When using a pigment dispersant, its amount is preferably 5 to 200 parts by mass relative to 100 parts by mass of the colorant, more preferably 8 to 150 parts by mass, and even more preferably 10 to 100 parts by mass. If the amount of pigment dispersant used is within the aforementioned range, when preparing a colorant dispersion containing two or more colorants, there is a tendency to obtain a colorant dispersion with a more uniform dispersion state.

[0306] The content of CI Pigment Yellow 185 relative to the total amount of colorant is preferably 6% by mass or more and 50% by mass or less, more preferably 9% by mass or more and 45% by mass or less, even more preferably 11% by mass or more and 40% by mass or less, and even more preferably 14% by mass or more and 35% by mass or less.

[0307] The content of CI Pigment Yellow 185 is preferably 1% by mass or more and 30% by mass or less, more preferably 2% by mass or more and 28% by mass or less, even more preferably 3% by mass or more and 26% by mass or less, and even more preferably 5% by mass or more and 24% by mass or less, relative to the total amount of solid components in the coloring and curing resin composition.

[0308] The content of xaton pigment relative to the total amount of colorant (A) is preferably 1 to 40% by mass, more preferably 5 to 20% by mass, and even more preferably 7 to 15% by mass. By adjusting the content of xaton pigment to the above range, crosstalk (leakage of red light) in the obtained color filter can be further reduced. In addition, from the viewpoint of further reducing the mixing of red light into the green region in the obtained color filter, it is also preferable that the xaton pigment (preferably the compound represented by formula (1)) exceeds 5% by mass relative to the total amount of colorant.

[0309] The content of zeatin pigment is preferably 0.5 to 20% by mass, more preferably 1 to 18% by mass, and even more preferably 2 to 16% by mass, relative to the total amount of solid components in the coloring and curing resin composition.

[0310] The content of red pigment relative to the total amount of colorant is preferably 10% by mass or more and 65% by mass or less, more preferably 15% by mass or more and 63% by mass or less, even more preferably 20% by mass or more and 61% by mass or less, and even more preferably 25% by mass or more and 59% by mass or less.

[0311] The content of red pigment is preferably 5% by mass or more and 40% by mass or less, more preferably 10% by mass or more and 35% by mass or less, and even more preferably 15% by mass or more and 34% by mass or less, relative to the total amount of solid components in the coloring curable resin composition.

[0312] In 100% by mass of red pigment, the content of the compound represented by formula (i) is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more. In 100% by mass of red pigment, the content of the compound represented by formula (i) can be 100% by mass.

[0313] The content of orange pigment relative to the total amount of colorant is preferably 0% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 35% by mass or less, and even more preferably 3% by mass or more and 30% by mass or less.

[0314] The content of orange pigment is preferably 0% by mass or more and 30% by mass or less, more preferably 0.5% by mass or more and 25% by mass or less, and even more preferably 1% by mass or more and 20% by mass or less, relative to the total amount of solid components in the coloring curable resin composition.

[0315] In 100% by mass of orange pigment, the content of the compound represented by formula (II) is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more. In 100% by mass of orange pigment, the content of the compound represented by formula (II) can be 100% by mass.

[0316] The total content of CI pigment yellow 185, thallium pigment, red pigment, and orange pigment relative to the total amount of colorant is preferably 70% by mass or more, more preferably 83% by mass or more, and even more preferably 90% by mass or more.

[0317] The total content of colorant (A) (preferably CI Pigment Yellow 185, Xanthan pigment, red pigment, and orange pigment) relative to the total amount of solid components in the coloring curable resin composition is, for example, 10 to 75% by mass, preferably 20 to 70% by mass, and more preferably 30 to 65% by mass.

[0318] It should be noted that, in this specification, the term "total amount of solid components" refers to the total amount of components after removing the solvent from the coloring and curing resin composition of the present invention. The total amount of solid components and the content of each component therewith can be determined, for example, by known analytical methods such as liquid chromatography and gas chromatography.

[0319] <Resin (B)>

[0320] The resin (B) is not particularly limited, but an alkali-soluble resin is preferred. Examples of resin (B) include resins [K1] to [K6].

[0321] Resin [K1]: A copolymer having structural units of at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and structural units of monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond;

[0322] Resin [K2]: A copolymer having structural units from the aforementioned (a) and structural units from the aforementioned (b), and structural units from monomer (c) that can copolymerize with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0323] Resin [K3]: a copolymer having structural units from (a) and (c) above;

[0324] Resin [K4]: a copolymer having structural units obtained by adding the aforementioned (b) to structural units from the aforementioned (a) and structural units from the aforementioned (c), and comprising structural units from (a) that have not been added (b);

[0325] Resin [K4']: A copolymer having structural units obtained by adding the aforementioned (b) to structural units from the aforementioned (a) and structural units from the aforementioned (c), and containing no structural units from (a) that have not been added (b);

[0326] Resin [K5]: A copolymer having structural units obtained by adding the aforementioned (a) to structural units from the aforementioned (b) and structural units from the aforementioned (c) (may contain structural units from (b) that have not been added to (a), but preferably do not);

[0327] Resin [K6]: a copolymer having a structural unit formed by adding the aforementioned (a) to a structural unit from the aforementioned (b) and further adding a carboxylic anhydride, and a structural unit from the aforementioned (c).

[0328] As for (a), specifically, for example, the following can be cited:

[0329] Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and p-vinylbenzoic acid;

[0330] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid.

[0331] 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, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups;

[0332] Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxylic acid bicyclic [2.2.1]hept-2-ene anhydride and other unsaturated dicarboxylic acid anhydrides;

[0333] Unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids with two or more members, such as succinate mono[2-(meth)acryloyloxyethyl] ester and phthalate mono[2-(meth)acryloyloxyethyl] ester.

[0334] Unsaturated acrylates such as α-(hydroxymethyl)acrylic acid, which contain both hydroxyl and carboxyl groups in the same molecule; etc.

[0335] Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferred, considering both copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0336] (b) For example, it refers to a polymeric compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., selected from at least one of the group consisting of ethylene oxide ring, oxobutane ring and tetrahydrofuran ring) and an olefinic unsaturated bond. (b) Preferably, it is a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0337] It should be noted that in this specification, "(meth)acrylic acid" means 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.

[0338] As (b), examples include monomers having epoxy ethyl and olefinic unsaturated bonds (b1) (hereinafter sometimes referred to as "(b1)"), monomers having oxocyclobutyl and olefinic unsaturated bonds (b2) (hereinafter sometimes referred to as "(b2)"), monomers having tetrahydrofuranyl and olefinic unsaturated bonds (b3) (hereinafter sometimes referred to as "(b3)"), etc.

[0339] As (b1), examples include monomers (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure of epoxidized aliphatic unsaturated hydrocarbons in the form of straight or branched chains, and monomers (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure of epoxidized alicyclic unsaturated hydrocarbons.

[0340] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methylo-vinylbenzyl glycidyl ether, α-methylm-vinylbenzyl glycidyl ether, α-methylp-vinylbenzyl glycidyl ether, and 2,3-bis(glycidyloxymethyl) Styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

[0341] Examples of compounds represented by (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), methyl 3,4-epoxycyclohexyl methacrylate (e.g., Cyclomer A400; manufactured by Daicel Co., Ltd.), methyl 3,4-epoxycyclohexyl methacrylate (e.g., Cyclomer M100; manufactured by Daicel Co., Ltd.), compounds represented by formula (BI), and compounds represented by formula (BII).

[0342]

[0343] In formulas (BI) and (BII), R e and R f It represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be replaced by a hydroxyl group.

[0344] X e and X f Indicates a single bond, *-R g -、*-R g -O-、*-R g -S- or *-R g -NH-.

[0345] R g It represents the dimethyl groups of alkanes with 1 to 6 carbon atoms.

[0346] * indicates a connection to O.

[0347] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0348] Examples of alkyl groups in which hydrogen atoms are replaced by hydroxyl groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

[0349] As R e and R f Preferably, hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups are included; more preferably, hydrogen atoms and methyl groups are included.

[0350] Examples of alkane dimethyl groups include methylene, ethylene, propane-1,2-dimethyl, propane-1,3-dimethyl, butane-1,4-dimethyl, pentane-1,5-dimethyl, and hexane-1,6-dimethyl.

[0351] As X e and X f Preferably, single bonds, methylene, ethylene, *-CH2-O- and *-CH2CH2-O- are examples of such bonds, and more preferably, single bonds and *-CH2CH2-O- (* indicates a bond with O).

[0352] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-1-5), (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.

[0353]

[0354] Examples of compounds represented by formula (BII) include compounds represented by any one 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.

[0355]

[0356] The compounds represented by formula (BI) and formula (BII) can be used individually or in combination of two or more. When using compounds represented by formula (BI) and formula (BII), their content ratio [compound represented by formula (BI): compound represented by formula (BII)] is preferably 5:95 to 95:5 on a molar basis, more preferably 20:80 to 80:20.

[0357] As (b2), a monomer having an oxetyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0358] As (b3), a monomer having a tetrahydrofuran group and a (meth)acryloyloxy group is more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemicals Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0359] As for (b), from the perspective of further improving the reliability of the obtained color filter, such as heat resistance and chemical resistance, (b1) is preferred. Furthermore, from the perspective of excellent storage stability of the color-curing resin composition, (b1-2) is more preferred.

[0360] Examples of (c) include (meth)acrylate monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters; vinyl monomers such as vinyl monomers having unsaturated aliphatic hydrocarbon rings or aromatic rings; maleimides; and so on.

[0361] Examples of (meth)acrylate monomers include: methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, and other (meth)acrylates having straight-chain or branched aliphatic saturated hydrocarbon groups.

[0362] (Meth)acrylates such as allyl methacrylate and propargyl methacrylate are aliphatic unsaturated hydrocarbon groups with straight or branched chains.

[0363] Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclohexyl (meth)acrylate [5.2.1.0] 2,6 Decane-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentyl ester" in this technical field; sometimes also called "(meth)acrylate tricyclodecyl ester"), isobornyl ester of (meth)acrylate, adamantane ester of (meth)acrylate, and other (meth)acrylates having cyclic saturated hydrocarbon groups;

[0364] (Meth)acrylate tricyclic [5.2.1.0] 2,6 Decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate dicyclopentyloxyethyl ester, and other (meth)acrylates containing cyclic unsaturated aliphatic hydrocarbon groups;

[0365] (Meth)acrylates such as phenyl methacrylate, naphthyl methacrylate, benzyl methacrylate, and phenoxybenzyl methacrylate contain aromatic rings.

[0366] Hydroxyl acrylates such as 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.

[0367] Examples of unsaturated dicarboxylic acid esters include diethyl maleate, diethyl fumarate, and diethyl itaconic acid.

[0368] Among these unsaturated carboxylic acid esters, the preferred choices are:

[0369] Methyl methacrylate, 2-ethylhexyl acrylate, and other (meth)acrylates C 1-10 Alkyl esters;

[0370] (Meth)acrylate tricyclic [5.2.1.0] 2,6 Decane-8-yl esters and other (meth)acrylates containing cyclic saturated hydrocarbon groups;

[0371] (Meth)acrylate tricyclic [5.2.1.0] 2,6 ] Decen-8-yl esters and other (meth)acrylates containing cyclic unsaturated aliphatic hydrocarbon groups;

[0372] (Meth)acrylates such as benzyl methacrylate and phenoxybenzyl methacrylate contain aromatic rings.

[0373] Examples of vinyl monomers with unsaturated aliphatic hydrocarbon rings include bicyclo[2.2.1]hept-2-ene (or 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)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, and 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene. .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- Bicyclic unsaturated compounds such as tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene.

[0374] Examples of vinyl monomers with aromatic rings include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene.

[0375] Other vinyl monomers include acrylonitrile, methacrylonitrile, and other monomers containing nitrile groups;

[0376] Monomers containing halogen atoms, such as vinyl chloride and vinylidene chloride;

[0377] Acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene; etc.

[0378] Among these vinyl monomers, considering copolymerization reactivity and heat resistance, styrene-based monomers such as styrene and vinyltoluene, and bicyclic unsaturated compounds such as bicyclic [2.2.1]hept-2-ene (or 2-norbornene) are preferred.

[0379] Examples of maleimides include N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 3-maleimide benzoate-N-succinimide ester, 4-maleimide butyrate-N-succinimide ester, 6-maleimide hexanoate-N-succinimide ester, 3-maleimide propionate-N-succinimide ester, and N-(9-acridyl)maleimide.

[0380] Among these maleimides, considering copolymerization reactivity and heat resistance, N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide, which have alicyclic hydrocarbon groups or aromatic hydrocarbon groups, are preferred.

[0381] The structural unit obtained by adding (b) to the structural unit from (a) refers to a unit formed by bonding (b) to the structural unit from (a) constituting the main chain of the copolymer through addition, having an unsaturated side group from (b). In this structural unit, (a) can be any of the aforementioned examples, and (b) can also be any of the aforementioned examples. As (a), unsaturated monocarboxylic acids such as (meth)acrylic acid are preferred. As (b), monomers (b1) having epoxy ethyl and olefinic unsaturated bonds are preferred, and monomers (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure after epoxidation are more preferred.

[0382] The structural unit obtained by adding (a) to the structural unit from (b) refers to a unit formed by bonding (a) to the structural unit from (b) constituting the main chain of the copolymer through addition, having an unsaturated side group from (a). In this structural unit, (b) can be any of the aforementioned examples, and (a) can also be any of the aforementioned examples. As (b), a monomer (b1) having an epoxy ethyl and olefinic unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure after epoxidation is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0383] The structural unit obtained by adding (a) to a structural unit from (b) and further adding a carboxylic anhydride refers to a structural unit obtained by bonding a carboxylic anhydride to a hydroxyl group generated by adding (a) to a structural unit from (b) constituting the main chain of the copolymer via half-esterification, having a carboxyl side group from the carboxylic anhydride and an unsaturated side group from (a). In this structural unit, (b) can be any of the aforementioned examples, and (a) can also be any of the aforementioned examples. As (b), a monomer (b1) having an epoxy ethyl and olefinic unsaturated bond is preferred, and a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure after epoxidation is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0384] As the carboxylic anhydride, the following polycarboxylic anhydrides can be mentioned: saturated aliphatic polycarboxylic anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, adipic anhydride; unsaturated aliphatic polycarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride; aromatic polycarboxylic anhydrides such as 3-vinylphthalic anhydride, 4-vinylphthalic anhydride; alicyclic polycarboxylic anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc.

[0385] In the resin [K1], in all the structural units constituting the resin [K1], the ratio of the structural units from each is preferably:

[0386] Structural units from (a): 2 to 60 mol%

[0387] Structural units from (b): 40 to 98 mol%,

[0388] More preferably:

[0389] Structural units from (a): 10 to 50 mol%

[0390] Structural units from (b): 50 to 90 mol%.

[0391] In addition, it is preferably substantially free of structural units from (c).

[0392] In all the structural units constituting the resin [K1], the total of the structural units from (a) and the structural units 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%.

[0393] When the ratio of the structural units of the 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 obtained color filter tend to be excellent.

[0394] The resin [K1] can be produced, for example, according to the methods described in the reference document "Experimental Methods of Polymer Synthesis" (高分子合成の実験法) (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited references described in that document.

[0395] Specifically, the following method can be used: A specified amount of (a) and (b), the polymerization initiator, and the solvent are added to a reaction vessel, for example, by replacing oxygen with nitrogen to create a deoxygenated atmosphere, and the mixture is heated and kept at a constant temperature while stirring. It should be noted that the polymerization initiator and solvent used herein are not particularly limited, and substances commonly used in the art can be used. For example, as polymerization initiators, examples include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) and organic peroxides (benzoyl peroxide, tert-butyl peroxide-2-ethylhexanoate, etc.). As solvents, any solvent sufficient to dissolve the monomers is acceptable; examples include solvents described later as the solvent (E) for the coloring and curing resin composition of the present invention.

[0396] It should be noted that the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or from a substance removed in solid (powder) form by methods such as reprecipitation. In particular, by using the solvent contained in the color-curing resin composition of the present invention as the solvent during polymerization, the reaction solution can be directly used in the preparation of the color-curing resin composition of the present invention, thus simplifying the manufacturing process of the color-curing resin composition of the present invention.

[0397] In resin [K2], the preferred ratio of structural units from each of the various structural units constituting resin [K2] is:

[0398] Structural units from (a): 1–70 mol%

[0399] Structural units from (b): 1–60 mol%

[0400] Structural units from (c): 20–95 mol%.

[0401] More preferably:

[0402] Structural units from (a): 3–50 mol%

[0403] Structural units from (b): 3–40 mol%

[0404] Structural units from (c): 30–90 mol%.

[0405] A further preferred option is:

[0406] Structural units from (a): 5–40 mol%

[0407] Structural units from (b): 5–30 mol%

[0408] Structural units from (c): 40–80 mol%.

[0409] Of all the structural units constituting resin [K2], the total of the structural units 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%.

[0410] If the ratio of the structural units of resin [K2] is within the above range, the color-curing resin composition tends to have excellent storage stability, developability when forming color patterns, and solvent resistance, heat resistance and mechanical strength of the obtained color filter.

[0411] In resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. As (b), a monomer (b1) having an epoxy ethyl and olefinic unsaturated bond is preferred, and a monomer (b1-2) having an epoxidized alicyclic unsaturated hydrocarbon structure is more preferred. As (c), (meth)acrylates having cyclic unsaturated aliphatic hydrocarbon groups, (meth)acrylates having aromatic rings, and dicarbonylimide derivatives are preferred.

[0412] Resin [K2] can be manufactured in the same manner as the method described in the manufacturing method of resin [K1].

[0413] In resin [K3], the preferred ratio of structural units from each of the various structural units constituting resin [K3] is:

[0414] Structural units from (a): 2–60 mol%

[0415] Structural units from (c): 40–98 mol%.

[0416] More preferably:

[0417] Structural units from (a): 10–50 mol%

[0418] Structural units from (c): 50–90 mol%.

[0419] A further preferred option is:

[0420] Structural units from (a): 35–45 mol%

[0421] Structural units from (c): 55–65 mol%.

[0422] In addition, it is preferable that the structure does not substantially contain any structural units from (b).

[0423] Of all the structural units constituting resin [K3], the total of the structural units from (a) and the structural units 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%.

[0424] In resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (c) is preferably a (meth)acrylate having an aromatic ring.

[0425] Resin [K3] can be manufactured in the same manner as the method described in the manufacturing method of resin [K1].

[0426] In resin [K4], the preferred ratio of structural units from each of the various structural units constituting resin [K4] is:

[0427] Structural units from (a) (unadded to (b)): 1–60 mol%

[0428] Structural units obtained by adding (b) to structural units from (a): 1–50 mol%

[0429] Structural units from (c): 30–90 mol%.

[0430] More preferably:

[0431] Structural units from (a) (unadded to (b)): 5–50 mol%

[0432] Structural units obtained by adding (b) to structural units from (a): 5–40 mol%

[0433] Structural units from (c): 35–80 mol%.

[0434] A further preferred option is:

[0435] Structural units from (a) (unadded to (b)): 10–40 mol%

[0436] Structural unit obtained by adding (b) to the structural unit from (a): 10–25 mol%.

[0437] Structural units from (c): 40–75 mol%.

[0438] Of all the structural units constituting resin [K4], the total of the structural units from (a) (without addition (b)), the structural units obtained by adding (b) to the structural units from (a), and the structural units 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%.

[0439] As the structural unit from (a) (without addition (b)), it is preferably a structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid. As the structural unit obtained by adding (b) to the structural unit from (a), it is preferably a structural unit obtained by adding a monomer (b1-1) having a linear or branched aliphatic unsaturated hydrocarbon structure to the structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid. As the structural unit from (c), it is preferably one or more selected from (meth)acrylates having linear or branched aliphatic saturated hydrocarbon groups, (meth)acrylates having cyclic saturated hydrocarbon groups, (meth)acrylates having aromatic rings, bicyclic unsaturated compounds, and styrene monomers, more preferably two or more. When (c) has two structural units from (c), two of them are selected from unsaturated carboxylic acid esters such as (meth)acrylates, (meth)acrylates having cyclic saturated hydrocarbon groups, and (meth)acrylates having aromatic rings. Preferably, two or more are selected from dicyclic unsaturated compounds and vinyl monomers such as styrene monomers.

[0440] The resin [K4] can be manufactured by obtaining a copolymer of (a) and (c) by adding a cyclic ether having 2 to 4 carbon atoms in (b) to a carboxylic acid and / or carboxylic anhydride in (a).

[0441] First, the copolymers of (a) and (c) are manufactured in the same manner as described in the method for manufacturing resin [K1]. In this case, the ratio of the structural units from each is preferably the same as that described in resin [K3].

[0442] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride from (a) in the aforementioned copolymer.

[0443] After producing the copolymer of (a) and (c), the atmosphere inside the flask is replaced with air instead of nitrogen, and (b), a reaction catalyst for the carboxylic acid or carboxylic anhydride with the cyclic ether (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.) and a polymerization inhibitor (e.g., hydroquinone, p-hydroxyanisole, etc.) are added to the flask. The reaction is carried out at 60 to 130°C for 1 to 10 hours, thereby producing resin [K4].

[0444] Compared to 100 moles in (a), the amount used in (b) is preferably 5 to 80 moles, more preferably 10 to 75 moles. By setting it within this range, there is a tendency for the coloring curable resin composition to have good storage stability, developability when forming a pattern, and a good balance of solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern.

[0445] The amount of the aforementioned reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total mass of 100 parts by mass of (a), (b), and (c). The amount of the aforementioned polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total mass of 100 parts by mass of (a), (b), and (c).

[0446] The charging method, reaction temperature, and time, among other reaction conditions, can be adjusted appropriately by taking into account the manufacturing equipment and the heat generated by polymerization. It should be noted that the charging method and reaction temperature can be adjusted appropriately by considering the manufacturing equipment and the heat generated by polymerization, just as with polymerization conditions.

[0447] In resin [K4'], the preferred ratio of structural units from each of the various structural units constituting resin [K4'] is:

[0448] Structural units obtained by adding (b) to structural units from (a): 5–95 mol%

[0449] Structural units from (c): 5–95 mol%.

[0450] More preferably:

[0451] Structural units obtained by adding (b) to structural units from (a): 15–90 mol%.

[0452] Structural units from (c): 10–85 mol%.

[0453] A further preferred option is:

[0454] Structural units obtained by adding (b) to structural units from (a): 20–80 mol%

[0455] Structural units from (c): 20–80 mol%.

[0456] In addition, it does not actually contain structural units from (a) and not added to (b).

[0457] Of all the structural units constituting resin [K4'], the total of the structural units obtained by adding (b) to the structural unit from (a) and the structural units 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%.

[0458] The structural unit obtained by adding (b) to the structural unit from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure of linear or branched aliphatic unsaturated hydrocarbons epoxidized to a structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit from (c) is preferably one or more selected from (meth)acrylates having linear or branched aliphatic saturated hydrocarbon groups and (meth)acrylates having cyclic saturated hydrocarbon groups, more preferably two or more.

[0459] The resin [K4'] can be manufactured by referring to the above-described method for manufacturing resin [K4]. The amount of (b) used is preferably 100 moles or more, more preferably 100 moles, relative to (a) 100 moles.

[0460] In resin [K5], the preferred ratio of structural units from each of the various structural units constituting resin [K5] is:

[0461] Structural units from (b) (unadded to (a)): 0–30 mol%

[0462] Structural units obtained by adding (a) to structural units from (b): 5–95 mol%

[0463] Structural units from (c): 5–95 mol%.

[0464] More preferably:

[0465] Structural units from (b) (unadded to (a)): 0–10 mol%

[0466] Structural units obtained by adding (a) to structural units from (b): 15–90 mol%

[0467] Structural units from (c): 10–85 mol%.

[0468] Further preferred options are:

[0469] Structural units from (b) (unadded to (a)): 0–5 mol%

[0470] Structural units obtained by adding (a) to structural units from (b): 20–80 mol%

[0471] Structural units from (c): 20–80 mol%.

[0472] Of all the structural units constituting resin [K5], the total of the structural units from (b) (without addition to (a)), the structural units obtained by adding (a) to the structural units from (b), and the structural units 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%.

[0473] As a structural unit from (b) (without addition (a)), it is preferably a structural unit from a monomer (b1-1) having a structure of epoxidized aliphatic unsaturated hydrocarbons with straight or branched chains. As a structural unit obtained by adding (a) to a structural unit from (b), it is preferably a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit from a monomer (b1-1) having a structure of epoxidized aliphatic unsaturated hydrocarbons with straight or branched chains. As a structural unit from (c), it is preferably one or more selected from (meth)acrylates having a straight or branched aliphatic saturated hydrocarbon group and (meth)acrylates having a cyclic saturated hydrocarbon group, more preferably two or more.

[0474] Regarding resin [K5], as a first stage, copolymers of (b) and (c) are obtained in the same manner as resin [K1] described above. Similarly, for the obtained copolymer, the solution after the reaction can be used directly, or a concentrated or diluted solution can be used, or a substance extracted in solid (powder) form by methods such as reprecipitation can be used.

[0475] The preferred ratios of structural units from (b) and (c) are respectively, relative to the total molar number of all structural units constituting the aforementioned copolymer.

[0476] Structural units from (b): 5–95 mol%

[0477] Structural units from (c): 5–95 mol%.

[0478] More preferably:

[0479] Structural units from (b): 10–90 mol%

[0480] Structural units from (c): 10–90 mol%.

[0481] Furthermore, under the same conditions as the manufacturing method of resin [K4] or resin [K4'], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether from (b) contained in the copolymer of (b) and (c), thereby obtaining resin [K5].

[0482] The amount of (a) used in reaction with the aforementioned copolymer is preferably 5 to 100 moles relative to 100 moles of (b). More preferably, it is 60 to 100 moles. Considering the high reactivity of cyclic ethers and the fact that unreacted (b) is less likely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is even more preferred.

[0483] In resin [K6], the preferred ratio of structural units from each of the various structural units constituting resin [K6] is:

[0484] Structural units from (b) (unadded to (a)): 0–30 mol%

[0485] The structural unit (unadditional carboxylic anhydride) obtained by adding (a) to the structural unit from (b): 5–70 mol%.

[0486] The structural unit formed by adding (a) to the structural unit from (b) and further adding carboxylic anhydride: 10–80 mol%

[0487] Structural units from (c): 10–60 mol%.

[0488] More preferably:

[0489] Structural units from (b) (unadded to (a)): 0–10 mol%

[0490] The structural unit (unadditional carboxylic anhydride) obtained by adding (a) to the structural unit from (b): 10–50 mol%.

[0491] The structural unit formed by adding (a) to the structural unit from (b) and further adding carboxylic anhydride: 25–60 mol%.

[0492] Structural units from (c): 15–50 mol%.

[0493] A further preferred option is:

[0494] Structural units from (b) (unadded to (a)): 0–5 mol%

[0495] The structural unit (unadditional carboxylic anhydride) obtained by adding (a) to the structural unit from (b): 15–35 mol%.

[0496] The structural unit formed by adding (a) to the structural unit from (b) and further adding carboxylic anhydride: 35–55 mol%.

[0497] Structural units from (c): 20–40 mol%.

[0498] Of all the structural units constituting resin [K6], the total of the structural units from (b) (without addition to (a)), the structural units obtained by adding (a) to the structural units from (b) (without addition to carboxylic anhydride), the structural units obtained by adding (a) to the structural units from (b) and further adding carboxylic anhydride, and the structural units 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%.

[0499] As a structural unit from (b) (without addition to (a)), it is preferably a structural unit from a monomer (b1-1) having a structure of epoxidized aliphatic unsaturated hydrocarbons with straight or branched chains. As a structural unit obtained by adding (a) to a structural unit from (b) (without addition to carboxylic anhydride), it is preferably a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit from a monomer (b1-1) having a structure of epoxidized aliphatic unsaturated hydrocarbons with straight or branched chains. As a structural unit obtained by adding (a) to a structural unit from (b) and further adding a carboxylic anhydride, it is preferably a structural unit obtained by adding an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structural unit from a monomer (b1-1) having a structure of epoxidized aliphatic unsaturated hydrocarbons with straight or branched chains, and further adding a saturated aliphatic polycarboxylic anhydride such as succinic anhydride. As the structural unit from (c), it is preferably selected from one or more of (meth)acrylates having a straight-chain or branched aliphatic saturated hydrocarbon groups and (meth)acrylates having cyclic saturated hydrocarbon groups, more preferably two or more.

[0500] Regarding resin [K6], as a first stage, copolymers (b) and (c) are obtained in the same manner as those for resin [K1] described above. Similarly, the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or from a substance extracted in solid (powder) form by methods such as reprecipitation.

[0501] The preferred ratios of structural units from (b) and (c) are respectively, relative to the total molar number of all structural units constituting the aforementioned copolymer.

[0502] Structural units from (b): 5–95 mol%

[0503] Structural units from (c): 5–95 mol%.

[0504] More preferably:

[0505] Structural units from (b): 10–90 mol%

[0506] Structural units from (c): 10–90 mol%.

[0507] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether from (b) present in the copolymer of (b) and (c). The amount of (a) used is preferably 80 to 100 moles relative to 100 moles of (b).

[0508] The carboxylic anhydride is reacted with a hydroxyl group generated by the reaction of the aforementioned cyclic ether with the carboxylic acid or carboxylic anhydride present in (a).

[0509] The amount of carboxylic anhydride used is preferably 0.05 to 1 mole relative to the amount of (a) used (in other words, 1 mole of hydroxyl group generated by using (a)), more preferably 0.10 to 0.8 moles, and even more preferably 0.13 to 0.7 moles.

[0510] As for resin (B), specifically, examples include:

[0511] 3,4-Epoxycyclohexylmethyl methacrylate / (meth)acrylate copolymer, 3,4-Epoxytricyclic methacrylate [5.2.1.0] 2,6 [K1] decyl ester / (meth)acrylic acid copolymer and other resins;

[0512] (Meth)acrylate glycidyl acrylate / (meth)acrylate benzyl acrylate / (meth)acrylate copolymer, (meth)acrylate glycidyl acrylate / styrene / (meth)acrylate copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid tricyclic [5.2.1.0] 2,6 ] Decene-8-yl ester copolymer, 3,4-epoxy tricyclic acrylate [5.2.1.0] 2,6 Decyl ester / (meth)acrylate / (meth)acrylate benzyl ester copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 Resins such as decyl ester / (meth)acrylic acid / (meth)acrylic acid phenoxybenzyl ester copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2];

[0513] Resins such as benzyl methacrylate / methacrylic acid copolymer and styrene / methacrylic acid copolymer [K3];

[0514] Resins obtained by adding glycidyl methacrylate to a portion of the carboxylic acid group of a benzyl methacrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate to a portion of the carboxylic acid group of a tricyclodecyl methacrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate to a portion of the carboxylic acid group of a tricyclodecyl methacrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate to a portion of the carboxylic acid group of a norbornene / vinyltoluene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl methacrylate to a portion of the carboxylic acid group of a norbornene / styrene / (meth)acrylic acid copolymer, etc. [K4];

[0515] Resins obtained by reacting a copolymer of tricyclodecyl methacrylate / (meth)acrylic acid with glycidyl methacrylate, and resins obtained by reacting a copolymer of tricyclodecyl methacrylate / styrene / (meth)acrylic acid with glycidyl methacrylate, etc. [K4'];

[0516] Resins obtained by reacting a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid, and resins obtained by reacting a copolymer of tricyclodecyl methacrylate / styrene / glycidyl methacrylate with (meth)acrylic acid, etc. [K5];

[0517] Resins obtained by reacting a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid, and further reacting it with tetrahydrophthalic anhydride; resins obtained by reacting a copolymer of 2-ethylhexyl methacrylate / tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid, and further reacting it with succinic anhydride; resins obtained by reacting a copolymer of methyl methacrylate / 2-ethylhexyl methacrylate / tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid, and further reacting it with succinic anhydride, etc. [K6]; etc.

[0518] Resin (B) can be used alone or in combination of two or more. As resin (B), it is preferably selected from at least one of resin [K1], resin [K2], resin [K4] and resin [K6], and more preferably resin [K2].

[0519] The weight-average molecular weight of resin (B), converted from polystyrene, is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. If the molecular weight is within the aforementioned range, there is a tendency for the hardness of the color filter to increase, the residual film rate to be high, the unexposed portion to have good solubility in the developer, and the resolution of the colored pattern to be improved.

[0520] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 to 6, more preferably 1.2 to 4.

[0521] The acid value of resin (B), calculated based on solid content, is preferably 20–170 mg-KOH / g, more preferably 50–150 mg-KOH / g, and even more preferably 80–135 mg-KOH / g. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0522] The content of resin (B) relative to the total amount of solid components in the coloring curable resin composition is preferably 5 to 60% by mass, more preferably 10 to 55% by mass, and even more preferably 14 to 45% by mass. If the content of resin (B) is within the aforementioned range, there is a tendency to form a coloring pattern, and furthermore, the resolution of the coloring pattern and the residual film rate are improved.

[0523] <Polymerizing Compounds (C)>

[0524] The polymerizable compound (C) is a compound that can be polymerized using active free radicals and / or acids generated by the polymerization initiator (D). Examples include compounds with polymerizable olefinic unsaturated bonds, and (meth)acrylate compounds are preferred.

[0525] The polymerizable compound (C) is preferably a polymerizable compound having three or more olefinic unsaturated bonds. Examples of such polymerizable compounds include, for instance, trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylates (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylates (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylates (e.g., tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylates (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylates (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ... Ethylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified pentaerythritol tri(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, alkylene glycol-modified dipentaerythritol poly(meth)acrylate (e.g., ethylene glycol-modified dipentaerythritol penta(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified dipentaerythritol penta(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate), caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), etc.

[0526] Preferably, it is selected from at least one of the following groups: 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; more preferably, it is ethylene glycol modified pentaerythritol poly(meth)acrylate or ethylene glycol modified dipentaerythritol poly(meth)acrylate.

[0527] 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.

[0528] 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.

[0529] The content of the polymeric compound (C) relative to the total amount of solid components in the coloring and curing resin composition is, for example, 5 to 65% by mass, preferably 6 to 50% by mass, and more preferably 8 to 30% by mass. If the content of the polymeric compound (C) is within the aforementioned range, there is a tendency to further improve the residual film rate during the formation of the color pattern and the chemical resistance of the color filter.

[0530] <Polymerization Initiator (D)>

[0531] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc. under the action of light and heat and can initiate polymerization. Known polymerization initiators can be used.

[0532] Examples of polymerization initiators that generate active free radicals include alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and bimidazole compounds.

[0533] The aforementioned O-acyl oxime compounds are compounds having a partial structure represented by formula (d1). Hereinafter, * denotes a linking bond.

[0534]

[0535] Examples of the aforementioned O-acyl oxime compounds include, for instance, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxane-2,4-dioxane-6-pentylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane- 1-Imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[4-(2-hydroxyethyloxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, etc. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) can be used. The O-acyl oxime compound is preferably selected from N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylthiophenyl]propane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylthiophenyl)propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylthiophenyl) At least one of the following is selected from the group consisting of octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, more preferably at least one of the following selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, and N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine. When these O-acyl oxime compounds are used, there is a tendency to obtain color filters with high brightness.

[0536] The aforementioned alkyl phenyl ketone compounds are preferably compounds having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have substituents.

[0537]

[0538] Examples of compounds having a partial structure represented by formula (d2) include, for example, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can be used.

[0539] Examples of compounds having a partial structure represented by formula (d3) include, for example, oligomers of 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, benzoyladimethyl ketal, etc.

[0540] From a sensitivity perspective, alkyl phenyl ketone compounds are preferably compounds having a partial structure represented by formula (d2).

[0541] Examples of the aforementioned triazine compounds include, for instance, 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-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6- [2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0542] Examples of the aforementioned acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl diphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.

[0543] Examples of the aforementioned biimidazole compounds include, for example, 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 Application Publication No. 6-75372, Japanese Patent Application Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis... (2-Chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (e.g., see 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 an alkoxycarbonyl group (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0544] In addition, examples of polymerization initiators (D) include: benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as methyl benzoyl peroxide, 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-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoin, methyl phenylglyoxylate, and titanium dioxide compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) described later.

[0545] Examples of polymerization initiators that generate acids include, for example, onion salts such as 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl benzyl sulfonium hexafluoroantimonate, triphenyl sulfonium p-toluenesulfonate, triphenyl sulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl toluenesulfonate, and benzoin toluenesulfonate.

[0546] As the polymerization initiator (D), it is preferable to have a polymerization initiator comprising at least one selected from the group consisting of alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds, and more preferably a polymerization initiator comprising an O-acyl oxime compound. In 100% by mass of the polymerization initiator (D), the content of the O-acyl oxime compound 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.

[0547] The content of polymerization initiator (D) is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C), more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 parts by mass. If the content of polymerization initiator (D) is within the aforementioned range, there is a tendency to achieve higher sensitivity and shorten the exposure time, thereby increasing the productivity of the color filter.

[0548] <Polymerization Initiator (D1)>

[0549] The coloring and curing resin composition of the present invention may further comprise a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound initiated by a polymerization initiator.

[0550] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0551] Examples of the aforementioned amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as michalcone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

[0552] Examples of the aforementioned 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.

[0553] Examples of the aforementioned thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0554] Examples of the aforementioned carboxylic acid compounds include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0555] When using these polymerization initiators (D1), their content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the combined amount of resin (B) and polymerizable compound (C). If the amount of polymerization initiator (D1) is within this range, there is a tendency to further improve the productivity of color filters by forming colored patterns with high sensitivity.

[0556] Solvent (E)

[0557] The solvent (E) is not particularly limited and solvents commonly used in the art can be used. Examples include ester solvents (solvents containing -COO- and not -O-), ether solvents (solvents containing -O- and not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing -CO- and not -COO-), alcohol solvents (solvents containing OH and not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

[0558] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0559] 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, phenethyl ether, and methyl anisole.

[0560] 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, ethyl 2-ethoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutylacetate, 3-methyl-3-methoxybutylacetate, 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.

[0561] 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.

[0562] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0563] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0564] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0565] Of the solvents mentioned above, from the perspective of coatability and drying properties, organic solvents with a boiling point of 120°C to 180°C at 1 atm are preferred. Preferably, the solvent is 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; more preferably, it is 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.

[0566] Furthermore, as the solvent (E), it is preferable to use a combination of ether solvent and ether ester solvent. In this case, C is preferred as the ether solvent. 2-3 Alkylene glycol mono-C 1-4 Alkyl ethers, more preferably propylene glycol mono-C 1-4 Alkyl ethers. Additionally, C4 is preferred as an ether ester solvent. 2-3 Alkylene glycol mono-C 1-4 Alkyl ether acetate, more preferably propylene glycol mono-C 1-4 Alkyl ether acetate.

[0567] The solvent (E) content is preferably 70-95% by mass, more preferably 73-92% by mass, and even more preferably 76-89% by mass, relative to the total amount of the color-curing resin composition. In other words, the solid component of the color-curing resin composition is preferably 5-30% by mass, more preferably 8-27% by mass, and even more preferably 11-24% by mass. If the solvent (E) content is within the aforementioned range, the flatness during coating becomes good, and the color concentration is not insufficient when forming the color filter, thus tending to improve display characteristics and sensitivity.

[0568] Leveling agent (F)

[0569] Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may also have polymerizable groups on their side chains.

[0570] Organosilicon surfactants include surfactants that have intramolecular siloxane bonds. Specifically, examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade 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 Advanced Materials Japan Contract Co., Ltd.).

[0571] As examples of the aforementioned fluorinated surfactants, surfactants with intramolecular fluorocarbon chains can be cited. Specifically, examples include Flourad (registered trademark) FC430, Flourad FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFACE (registered trademark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE RS-718-K (manufactured by DIC Co., Ltd.), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals Co., Ltd.), SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, and SURFLON... SC105 (manufactured by AGC Corporation (formerly Asahi Glass Corporation)) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

[0572] As examples of organosilicon surfactants containing fluorine atoms, surfactants with siloxane bonds and fluorocarbon chains within the molecule can be cited. Specifically, examples include MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Co., Ltd.).

[0573] The leveling agent (F) content 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 color-curing resin composition. It should be noted that this content does not include the aforementioned pigment dispersant content. If the leveling agent (F) content is within the aforementioned range, the flatness of the color filter can be well achieved.

[0574] <Other Ingredients>

[0575] Coloring and curing resin compositions may include fillers, other polymers, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art, as needed.

[0576] <Method for manufacturing color-curing resin compositions>

[0577] Colored curable resin compositions can be prepared, for example, by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and, as needed, a solvent (E), a leveling agent (F), a polymerization initiation aid (D1), and other components. The mixed colored curable resin composition can be filtered using a filter with a pore size of approximately 0.01–10 μm.

[0578] Colorant (A) can be dispersed using a pigment dispersant as described above to prepare a colorant dispersion that is uniformly dispersed in solution. By mixing the remaining components into such a colorant dispersion at a predetermined concentration, a target-colored curable resin composition can be prepared.

[0579] Alternatively, if the colorant (A) contains a dye, the solution can be prepared by pre-dissolving the dye in part or all of the solvent (E). It is preferable to filter the solution using a filter with a pore size of approximately 0.01 to 1 μm.

[0580] [Color Filter]

[0581] Methods for manufacturing color patterns for color filters using the color-curing resin composition of the present invention include photolithography, inkjet printing, and printing. Photolithography is preferred. The photolithography method involves coating the aforementioned color-curing resin composition onto a substrate, drying it to form a composition layer, exposing the composition layer through a photomask, and developing it. In the photolithography method, by not using a photomask during exposure and / or not developing, a color coating film, which is a cured product of the aforementioned composition layer, can be formed.

[0582] The 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.

[0583] As substrates, the following can be used: glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica-coated surface; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other color filter layers, resin layers, transistors, circuits, etc., can also be formed on these substrates. Furthermore, substrates on silicon substrates that have undergone HMDS treatment can also be used.

[0584] The formation of color pixels (color filters) based on photolithography can be performed using known or conventional apparatus and conditions. For example, it can be fabricated as follows: First, a color-curable resin composition is coated onto a substrate and then subjected to heat drying (pre-baking) and / or vacuum drying to remove volatile components such as solvents and dry the substrate, resulting in a smooth composition layer. Examples of coating methods include spin coating, slot coating, and a combination of slot and spin coating. The temperature during heat drying is preferably 30–120°C, more preferably 50–110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. Vacuum drying is preferably performed at a pressure of 50–150 Pa and a temperature range of 20–25°C. The film thickness of the composition layer is not particularly limited and can be appropriately selected depending on the desired thickness of the color filter.

[0585] Next, the composition layer is exposed through a photomask used to form the target color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended use can be used. The light source used for exposure is preferably a light source that generates light with wavelengths of 250–450 nm. For example, a filter that cuts off wavelengths less than 250 nm can be used to cut off this wavelength region; or a bandpass filter that extracts wavelengths around 436 nm, 408 nm, and 365 nm can be used to selectively extract these wavelength regions. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. To uniformly illuminate the entire exposure surface with parallel light, or to achieve precise alignment of the photomask and substrate, a reduction projection exposure device or a proximity exposure device, such as a mask aligner and a stepper, is preferably used.

[0586] A colored pattern is formed on a substrate by developing the exposed composition layer through contact with a developing solution. During development, the unexposed portions of the composition layer dissolve in the developing solution and are removed. As the developing solution, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Furthermore, the developing solution may also contain a surfactant. The developing method can be any of the following: spin-dip, immersion, or spray. Additionally, the substrate can be tilted at any angle during development.

[0587] After development, it is preferable to wash with water.

[0588] Preferably, the obtained colored pattern is further baked. The post-baking temperature is preferably 80-250°C, more preferably 100-245°C. The post-baking time is preferably 1-120 minutes, more preferably 2-30 minutes.

[0589] With regard to the color filter of the present invention, it is also preferable that, in the transmission spectrum with wavelength as the horizontal axis and transmittance as the vertical axis, the slope calculated according to the following formula is 0.03 to 0.06, based on the minimum wavelength λ1 that satisfies transmittance of 70% or more in the range of wavelengths above 580 nm and the transmittance T1 at that wavelength λ1, and the maximum wavelength λ2 that satisfies transmittance of 30% or less in the range of wavelengths below 580 nm and the transmittance T2 at that wavelength λ2.

[0590] Slope = (T1 - T2) / (λ1 - λ2)

[0591] The colored pattern and colored coating obtained in this way are useful as color filters, which are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc.

[0592] Example

[0593] The present invention will be described in more detail below with examples, but the present invention is not limited to the following examples. Of course, it can be implemented by appropriate modifications within the scope of the spirit described above and below, and all such modifications are included within the technical scope of the present invention. It should be noted that, unless otherwise specified, "parts" refers to "parts by mass" and "%" refers to "% by mass".

[0594] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200, MASS; Agilent LC / MSD6130).

[0595] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, converted to polystyrene, were determined using the GPC method under the following conditions.

[0596] Device: HLC-8120GPC (manufactured by Tosoh Corporation)

[0597] Column: TSK-GELG2000HXL

[0598] Column temperature: 40℃

[0599] Solvent: Tetrahydrofuran

[0600] Flow rate: 1.0 mL / min

[0601] The concentration of solid components in the analytical sample was 0.001%–0.01%.

[0602] Injection volume: 50μL

[0603] Detector: RI

[0604] Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0605] The ratio of weight-average molecular weight to number-average molecular weight (Mw / Mn) obtained above, converted to polystyrene, is used as the dispersity.

[0606] <Example of the synthesis of compound (I-1)>

[0607] According to International Publication No. 2022 / 065357, a compound (I-1) of orange pigment represented by the following formula was synthesized.

[0608]

[0609] <Example of the synthesis of compound (X)>

[0610] 40.5 parts of the compound represented by formula (IX) were mixed with 60.5 parts of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) under light-shielding conditions, and stirred at 150°C for 8 hours in 200 parts of N-methylpyridinone. The resulting reaction solution was cooled to room temperature and added to a mixture of 1200 parts of water and 75 parts of 35% hydrochloric acid. The mixture was stirred at room temperature for 1 hour, resulting in crystal precipitation. The precipitated crystals were collected as a residue by vacuum filtration, washed with 100 parts of methanol, and dried under reduced pressure at 60°C for 12 hours to obtain 49 parts of the compound represented by formula (X) (compound (X)). The yield was 85%.

[0611]

[0612] Identification of compounds represented by formula (X)

[0613] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 575

[0614] Exact Mass: 574

[0615] <Example of Resin (B-1) Synthesis>

[0616] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere. 256 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 80°C while stirring. Then, 3,4-epoxytricyclic acrylic acid [5.2.1.0] was added dropwise over 3 hours. 2,6 ] Decane-8-yl ester or / and 3,4-epoxytricyclic acrylate [5.2.1.0] 2,6 A mixed solution of 44 parts decane-9-yl ester, 57 parts acrylic acid, 249 parts 3-phenoxybenzyl acrylate, and 159 parts propylene glycol monomethyl ether acetate was prepared. On the other hand, a mixed solution of 25 parts 2,2-azobis(2,4-dimethylpentanonitrile) dissolved in 210 parts propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the addition was completed, the solution was maintained at the same temperature for 4 hours, then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a type B viscosity (23°C) of 51 mPa·s and a solid content of 36.0%. The weight-average molecular weight (Mw) of the resulting resin (B-1) was 1.1 × 10⁻⁶. 4 The dispersion is 1.98, and the acid value calculated based on the solid component is 123 mg-KOH / g.

[0617] Resin (B-1) has the following structural units.

[0618]

[0619] <Example of Resin (B-2) Synthesis>

[0620] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere. 340 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 80°C while stirring. Then, over 5 hours, 57 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise. 2,6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2,6A mixture of 54 parts of decane-9-yl ester (molar ratio 1:1), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was prepared. Meanwhile, a solution was prepared by dropwise addition of 40 parts of polymerization initiator 2,2-azobis(2,4-dimethylpentanonitrile) dissolved in 197 parts of propylene glycol monomethyl ether acetate over 6 hours. After the addition of the initiator solution was completed, the solution was maintained at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (resin (B-2)) solution with a viscosity of 127 mPa·s measured by a type B viscometer (23°C) and a solid content of 37.0% by weight. The weight-average molecular weight (Mw) of the resulting copolymer was 9.4 × 10⁻⁶. 3 The dispersion is 1.89, and the acid value converted from solid components is 114 mg-KOH / g. Resin (B-2) has the following structural units.

[0621]

[0622] <Preparation of colorant dispersions (A-1) to (A-11)>

[0623] The components were mixed in the proportions listed in Table 1 and dispersed using a bead mill to obtain colorant dispersions (A-1) to (A-11).

[0624] [Table 1]

[0625]

[0626] Preparation of coloring and curing resin compositions

[0627] <Examples 1-9 and Comparative Example 1>

[0628] The components were mixed in the proportions listed in Table 2 to obtain a coloring and curing resin composition.

[0629] [Table 2]

[0630]

[0631] <Polymerizing Compounds (C)>

[0632] Polymerizable compound (C): The compound represented by the following formula (NK Ester A-DPH-12E: manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0633]

[0634] <Polymerization Initiator (D)>

[0635] Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd., "PBG-327 (O-acyl oxime compound)")

[0636] Leveling agent (E)

[0637] Leveling agent (E): Polyether modified silicone oil (Toray Silicone SH8400 manufactured by Toray Dow Corning Co., Ltd.)

[0638] <Solvent(F)>

[0639] Solvent (F): Propylene glycol monomethyl ether acetate

[0640] <Creating Coloring Patterns>

[0641] After the coloring and curing resin composition was coated onto the surface of a 4-inch silicon substrate using spin coating, it was pre-baked at 100°C for 2 minutes to obtain the coloring composition layer. After cooling, it was then exposed using an exposure machine (NSR-2205i11D; Nikon Corporation) at 500 J / m². 2 ~3000J / m 2 The substrate with the colored composition layer was irradiated with light at an exposure level (based on 365 nm). During irradiation, photomasks were used to form dot patterns of 0.8 μm, 1.0 μm, and 2.0 μm square (with spacing of 1.6 μm, 2.0 μm, and 4.0 μm, respectively). The irradiated colored composition layer was immersed in an aqueous developer containing 0.3% tetramethylammonium hydroxide at 23°C for 30 seconds, rinsed with water, and then baked at 220°C for 5 minutes to obtain the post-baked colored pattern.

[0642] <Film Thickness Measurement>

[0643] The film thickness was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.) for the obtained colored pattern.

[0644] <Transmittance Evaluation>

[0645] For the obtained colored pattern, the transmittance in the wavelength region of 380nm to 780nm was measured every 1nm using a colorimeter (OSP-SP-200; manufactured by OLYMPUS Co., Ltd.). Lower transmittance at 430nm indicates less blue light leakage, and lower transmittance at 530nm indicates less green light leakage. This indicates excellent color performance as a color filter (especially a red filter). The results are shown in Table 3.

[0646] [Table 3]

[0647]

[0648] Furthermore, regarding the obtained coloring patterns, the slope was calculated based on the following formula, and the results for Examples 1 to 9 were all in the range of 0.03 to 0.06.

[0649] Slope = (T1 - T2) / (λ1 - λ2)

[0650] λ1: The minimum wavelength that satisfies a transmittance of 70% or higher in the wavelength range above 580nm.

[0651] λ2: The maximum wavelength within the wavelength range of less than 580 nm that satisfies a transmittance of less than 30%.

[0652] T1: Transmittance at λ1

[0653] T2: Transmittance at λ2

Claims

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

2. The colored curable resin composition according to claim 1, wherein The content of the xanthene dye is 1 mass% or more and 40 mass% or less with respect to the entire amount of the colorant.

3. The colored curable resin composition according to claim 1 or 2, wherein The total content of at least one selected from the group consisting of a red pigment and an orange pigment is 10 mass% or more and 65 mass% or less with respect to the entire amount of the colorant.

4. The colored curable resin composition according to claim 1 or 2, wherein The content of C.I. Pigment Yellow 185 is 6 mass% or more and 50 mass% or less with respect to the entire amount of the colorant.

5. The colored curable resin composition according to claim 1 or 2, wherein The red pigment and the orange pigment contain a pigment having one or more skeletons selected from the group consisting of a pyrrolopyryoline skeleton and an azo skeleton.

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

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

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

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

Images