KR20210091134A - coloring composition - Google Patents

Abstract

An object of the present invention is to provide a coloring composition excellent in heat resistance.
This invention is a coloring composition containing a coloring agent and resin, Comprising: The said coloring agent relates to the coloring composition containing the compound represented by a following formula (I), and a compound represented by a following formula (II).

Description

coloring composition

The present invention relates to a colored composition, and further to a colored curable resin composition, a color filter, and a display device.

The field of agricultural film WHEREIN: The fluorescent film which has a resin layer containing the brand name Lumogen (trademark) F orange 240 as a perylene type compound is known (patent document 1).

Japanese Patent Laid-Open No. 10-235776

In the field of coloring agents, the improvement of heat resistance is calculated|required.

An object of the present invention is to provide a coloring composition excellent in heat resistance. Another object of the present invention is to provide a coloring composition having high transmittance at a wavelength of 630 nm and excellent heat resistance.

This invention provides the following coloring compositions, coloring curable resin composition, a color filter, and a display apparatus.

[1] A coloring composition comprising a coloring agent and a resin, wherein the coloring agent contains a compound represented by the following formula (I) and a compound represented by the following formula (II).

[Formula 1]

[Formula 2]

[In formula (II),

R ¹ and R ² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms.

R ³ to ^{R 10} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

[2] The ^{coloring composition according to [1], wherein R 1} and R ² are a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms.

[3] The ^{coloring composition according to [1], wherein R 1} and R ² are each independently an alkanediyl group having 1 to 20 carbon atoms.

[4] The ^{coloring composition according to [1], wherein R 1} and R ² are each independently a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms.

[5] A colored curable resin composition comprising a compound represented by the following formula (I), a compound represented by the following formula (II), a resin, a polymerizable compound, a polymerization initiator, and a solvent.

[Formula 3]

[Formula 4]

[In formula (II),

R ¹ and R ² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms.

R ³ to ^{R 10} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

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

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

ADVANTAGE OF THE INVENTION According to this invention, the coloring composition excellent in heat resistance can be provided.

(1) Coloring composition

The coloring composition of this invention contains a coloring agent (henceforth a coloring agent (A)), and resin (henceforth resin (B)).

The colorant (A) contains a compound represented by formula (I) (hereinafter also referred to as compound (I)) and a compound represented by formula (II) (hereinafter also referred to as compound (II)).

The colorant (A) may contain a colorant other than the compound (I) and the compound (II) (hereinafter also referred to as a colorant (A1)).

The coloring agent (A) may contain 1 type, or 2 or more types of coloring agents (A1).

The coloring composition of this invention may contain the solvent (henceforth a solvent (E)).

Compound (I) and compound (II) may be disperse|distributed to the solvent (E).

<Compound (I)>

As compound (I), a commercially available compound can be used. As an example of a typical commercial item of compound (I), Lumogen (trademark) F Orange 240 (made by BASF) is mentioned.

Compound (I) can be produced by a known general production method, for example, by reacting 3,4,9,10-perylenetetracarboxylic dianhydride with 2,6-diisopropylaniline.

<Compound (II)>

The ^{divalent hydrocarbon group represented by R 1} and R ² has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms. Examples of the divalent hydrocarbon group include a divalent chain aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group, and a divalent aromatic hydrocarbon group.

The divalent chain aliphatic hydrocarbon group represented by ^{R 1} and R ^{2 may be saturated or unsaturated.} Among them, a divalent saturated chain aliphatic hydrocarbon group (hereinafter also referred to as alkanediyl group) is preferable. Linear may be sufficient as an alkanediyl group, and branched form may be sufficient as it.

Examples of the linear alkanediyl group represented by R ¹ and R ² include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane- 1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11- Diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16- a diyl group, a heptadecane-1,17-diyl group, an octadecane-1,18-diyl group, a nonadecan-1,19-diyl group, and an icosan-1,20-diyl group are mentioned. Among them, preferably an alkanediyl group having 1 to 10 carbon atoms, more preferably an alkanediyl group having 1 to 4 carbon atoms, still more preferably a methylene group, ethylene group, propane-1,3-diyl group, butane-1, 4-diyl group and pentane-1,5-diyl group.

As ^{the branched alkanediyl group represented by R 1} and R ² , for example, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2 -diyl group, 1-methylbutane-1,4-diyl group, 2-methylbutane-1,4-diyl group, 2,2-dimethylpropane-1,3-diyl group, 2-ethylpropane-1,3 -diyl group, 2-methylpentane-1,5-diyl group, 3-methylpentane-1,5-diyl group, 2,3-dimethylpentane-1,4-diyl group, etc. are mentioned. Among them, preferably a branched alkanediyl group having 4 to 10 carbon atoms, more preferably a branched alkanediyl group having 4 to 6 carbon atoms, and still more preferably

Examples of the divalent unsaturated chain aliphatic hydrocarbon group represented by R ¹ and R ² include an ethene-1,2-diyl group, a propa-1-ene-1,3-diyl group, and a buta-2-ene-1,4 group. -diyl group, penta-3-ene-1,4-diyl group, etc. are mentioned.

The divalent alicyclic hydrocarbon group represented by ^{R 1} and R ^{2 may be saturated or unsaturated.} Among them, a divalent saturated alicyclic hydrocarbon group (hereinafter also referred to as a cycloalkanediyl group) is preferable. The cycloalkanediyl group may be monocyclic or polycyclic may be sufficient as it. Examples of the monocyclic cycloalkanediyl group include a cyclopropane-1,2-diyl group, a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, and a cyclo Cycloalkanediyl groups, such as an octane-1, 5- diyl group, are mentioned. Examples of the polycyclic cycloalkanediyl group include norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. Diary, etc. are mentioned. Among them, a cyclohexane-1,4-diyl group is preferable.

Examples of the divalent unsaturated alicyclic hydrocarbon group represented by R ¹ and R ² include a cyclohexa-2-ene-1,4-diyl group.

The ^{divalent aromatic hydrocarbon group represented by R 1} and R ² (hereinafter also referred to as an arenediyl group) may be monocyclic or polycyclic.

Examples of the monocyclic areenediyl group include a benzenediyl group, an alkylbenzenediyl group, and a dialkylbenzenediyl group. Specific examples include benzene-1,2-diyl group, benzene-1,3-diyl group, benzene-1,4-diyl group, 2-methylbenzene-1,4-diyl group, 3-methylbenzene-1,4 -Diyl group, 2-methylbenzene-1,5-diyl group, 3-methylbenzene-1,5-diyl group, 4-methylbenzene-1,5-diyl group, 2-ethylbenzene-1,4-di Diyl, 3-ethylbenzene-1,4-diyl group, 3,5-dimethylbenzene-1,4-diyl group, 3,5-diethylbenzene-1,4-diyl group, 3-methyl-5-ethyl benzene-1,4-diyl group, 2-methyl-6-ethylbenzene-1,4-diyl group, etc. are mentioned.

Examples of the polycyclic areenediyl group include a naphthalene-1,5-diyl group, a naphthalene-1,6-diyl group, a naphthalene-1,7-diyl group, and a naphthalene-1,8-diyl group. In addition, the ^{divalent aromatic hydrocarbon group represented by R<1>} and R<^2> may be what connected two or more aromatic hydrocarbon groups, [1,1'-biphenyl]-4,4'- diyl group, etc. are mentioned.

The ^{arenediyl group represented by R 1} and R ² is preferably a monocyclic arenediyl group, more preferably a benzene-1,4-diyl group or a 3,5-dimethylbenzene-1,4-diyl group. , a 2-methylbenzene-1,4-diyl group, a 2-ethylbenzene-1,4-diyl group, and a 3-ethyl-5-methylbenzene-1,4-diyl group.

R ¹ and R ² are each independently and preferably a group selected from the group consisting of an alkanediyl group having 1 to 20 carbon atoms, a cycloalkanediyl group having 3 to 20 carbon atoms, and an arenediyl group having 6 to 20 carbon atoms; , more preferably a group selected from the group consisting of an alkanediyl group having 1 to 10 carbon atoms, a cycloalkanediyl group having 3 to 10 carbon atoms, and an areenediyl group having 6 to 10 carbon atoms, and more preferably a group having 1 to 6 carbon atoms. is a group selected from the group consisting of an alkanediyl group, a monocyclic cycloalkanediyl group having 5 to 7 carbon atoms, a benzenediyl group, an alkylbenzenediyl group, and a dialkylbenzenediyl group, and more preferably a methylene group; Ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, 4-methylpentane-1,2-diyl group, cyclohexane-1,4-diyl group , a group selected from the group consisting of a benzene-1,4-diyl group and a 3,5-dimethylbenzene-1,4-diyl group.

R ¹ and R ² are each independently a combination of two or more hydrocarbon groups, for example, at least one of a group combining a chain hydrocarbon group and an alicyclic hydrocarbon group, or an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group It can also be a combined contribution of dogs. The total carbon number of these combined groups is 20 or less.

R ¹ and R ² may be the same type or different types, preferably the same type.

Specific examples of R ¹ and R ² include groups represented by the following formulas. * and ** indicate a bond.

[Formula 5]

[Formula 6]

[Formula 7]

Preferred as R ¹ and R ² are each independently formulas (A-1) to (A-8), (A-14), (B-1) to (B-3), (B-16) to It is a group represented by (B-19) or (C-3). From a manufacturing viewpoint, it is preferable that it is said group.

Examples of the halogen atom represented by R ^{3 to R 10} include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, a fluorine atom and a chlorine atom are preferable.

Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R ³ to ^{R 10 include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.} The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic.

Examples of the saturated or unsaturated chain aliphatic hydrocarbon group represented by R ^{3 to R 10} include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. , tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, Hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl group, tritriacontyl group, tetratriacontyl group, pentatriacontyl group, hexatriacontyl group, straight-chain alkyl groups such as heptatriacontyl group, octatriacontyl group, nonatriacontyl group and tetracontyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10. Especially, it is still more preferable that it is a C1-C8 linear or branched alkyl group, and a methyl group or an ethyl group is especially preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^{3 to R 10} include a cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and 1-methylcyclohexyl group. , 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclo Hexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6 cycloalkyl groups such as ,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group and 4-cyclohexylcyclohexyl group; Cycloalkenyl groups, such as a cyclohexenyl group (For example, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; a norbornyl group, an adamantyl group, a bicyclo[2.2.2]octyl group, etc. are mentioned. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, particularly preferably 4 to 15 carbon atoms, still more preferably It is 5-15, Especially preferably, it is 5-10. Among them, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group is most preferable.

Examples of the aromatic hydrocarbon group represented by R ^{3 to R 10} include a phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, and 2,3-dimethyl Phenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m- Isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert-butyl)phenyl group, mesityl group, 4-ethylphenyl group , 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(2,4, 4-trimethyl-2-pentyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naph aromatic hydrocarbon groups such as tyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group and pyrenyl group; and the like. Carbon number of the said aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The ^{hydrocarbon group represented by R 3} to ^{R 10 may} be a group combining two or more of the above-mentioned hydrocarbon groups, for example, an aromatic hydrocarbon group, a combination of at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group, as an example , an aralkyl group such as a benzyl group, a phenethyl group, and a 1-methyl-1-phenylethyl group; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); Aryl alkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

The ^{hydrocarbon group represented by R 3} to ^{R 10 may} be a group combining two or more of the above-mentioned hydrocarbon groups, for example, a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group, for example, cyclopropylmethyl group, cyclopropylethyl group, cyclo and an alkyl group to which one or more alicyclic hydrocarbon groups such as butylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group and adamantylmethyl group are bonded.

The carbon number of the group which combined two or more of the said hydrocarbon groups becomes like this. Preferably it is 4-30, More preferably, it is 4-20, More preferably, it is 4-15, More preferably, it is 6-15.

Examples of the substituent that the hydrocarbon group having 1 to 40 carbon atoms represented by R ³ to ^{R 10} may have include, for example, a halogen atom, formyl group, carboxy group, formyloxy group, hydroxyl group, thiol group, sulfo group, sulfamoyl group, penta Fluorosulfanyl group, carbamoyl group, amino group, nitro group, cyano group, -COR ¹² , -COOR ¹² , -OCOR ¹² , -OR ¹² , -SR ¹² , -SOR ¹² , -SO ₂ R ¹² , -SO ₂ NHR ¹² , -SO ₂ NR ¹² R ¹³ , -CONHR ¹² , -CONR ¹² R ¹³ , -NHR ¹² , -NR ¹² R ¹³ , -NHCOR ¹² , -NR ¹³ COR ¹² , and the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, a fluorine atom and a chlorine atom are preferable.

R ¹² and R ¹³ each independently represent an alkyl group, a phenyl group or a naphthyl group.

The number of carbon atoms of the alkyl group represented by R ¹² and R ¹³ is preferably 1 to 20, more preferably 1 to 10, still more preferably 1 to 5.

Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, A pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, etc. are mentioned.

-COR ^{12 is} acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decano group Diary, undecanoyl group, dodecanoyl group, henicosanoyl group, benzoyl group, etc. are mentioned.

-COOR ¹² is a methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxy group and a carbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group and an icosyloxycarbonyl group.

As -OCOR ¹² , acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl)hexanoyloxy group, heptanoyloxy group, Octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, 2-propenylcarbonyloxy group, etc. can be heard

Examples of -OR ¹² include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a phenoxy group, and a naphthyloxy group.

-SR ^{12 is a} methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, a tert-butylsulfanyl group, a pentylsulfanyl group, a hexylsulfanyl group, a (2-ethyl)hexylsulfanyl group, a heptylsulfanyl group, and an octylsulfanyl group. nyl group, nonylsulfanyl group, decylsulfanyl group, undecylsulfanyl group, dodecylsulfanyl group, icosylsulfanyl group, phenylsulfanyl group, o-tolylsulfanyl group, etc. are mentioned.

Examples of -SOR ¹² include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, a phenylsulfinyl group, and a naphthylsulfinyl group.

Examples of -SO ₂ R ¹² include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a phenylsulfonyl group, and a naphthylsulfonyl group.

As -SO ₂ NHR ¹² , N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group , N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2- Ethyl) hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N -icosylsulfamoyl group, N-phenylsulfamoyl group, etc. are mentioned.

As -SO ₂ NR ¹² R ¹³ , N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N, N-dipropylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulf Pamoyl group, N,N-disec-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N -dipentylsulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-dihep Tylsulfamoyl group, N,N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfa pamoyl group, N,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc. are mentioned.

-CONHR ^{12 is} N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N -sec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl) Hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N -icosylcarbamoyl group, N-phenylcarbamoyl group, etc. are mentioned.

-CONR ¹² R ^{13 is} N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N- Dipropylcarbamoyl group, N,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group , N,N-disec-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyl Octylcarbamoyl group, N,N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl) Hexylcarbamoyl group, N,N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decyl group Methylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group, N, N-diphenylcarbamoyl group etc. are mentioned.

-NHR ^{12 is} N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group , N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dode A sylamino group, N-icosylamino group, N-phenylamino group, etc. are mentioned.

-NR ¹² R ^{13 is} N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N- Isopropylmethylamino group, N,N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert- Butylamino group, N,N-butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N, N-di(2-ethyl)hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethyl an amino group, N,N-dodecylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc. are mentioned.

-NHCOR ^{12 is} acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoyl an amino group, a nonanoylamino group, a decanoylamino group, an undecanoylamino group, a dodecanoylamino group, a henicosanoylamino group, a benzoylamino group, etc. are mentioned.

Examples of -NR ¹³ COR ¹² include N-methyl-N-acetylamino group.

_{-CH 2} - which is contained in the hydrocarbon group having 1 to 40 carbon atoms and does not constitute a ring represented by R ³ to ^{R 10} is -O-, -CO-, -S(O) ₂ -, -NR ^x1 - may be substituted with However, when -CH ₂ - is substituted, -COOH and -S(O) ₂ OH are not formed. R ^x1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, isopropyl group, isobutyl group, sec-butyl group, isopentyl group and the like.

Examples of R ³ to ^{R 10} include groups represented by the following formulas. * indicates a bond.

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

R ³ to ^{R 10 are} preferably a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, -CH ₃ , formulas (D-1) to (D-18), (E-1) to (E-27) ), (F-1) to (F-18) and (G-1) to (G-27). As for the said halogen atom, a chlorine atom and a bromine atom are preferable. When such an atom is included as a halogen atom, the colored pattern and colored coating film formed from colored curable resin composition will show the outstanding heat resistance, or it will become a tendency for the transmittance|permeability in wavelength 630nm to be high. From the viewpoint of production, R ³ to ^{R 10} are preferably a hydrogen atom.

Specific examples of the compound (II) include compounds shown in Tables 1 to 3 below.

[Table 1]

[Table 2]

[Table 3]

Among them, compounds (II-1) to (II-9) and (I-82) to (I-117) are preferable, and from the viewpoint of heat resistance and light resistance, compounds (II-2) to (II) are more preferable. -6), (II-8), and (II-91) to (II-108).

As a preferred embodiment of the compound (II) in the present invention, a compound represented by the following formula (IIa) (hereinafter also referred to as compound (IIa)) is exemplified.

[Formula 12]

[In formula (IIa),

R ^1a and R ^2a each independently represent an alkanediyl group having 1 to 20 carbon atoms.

R ^3a to ^{R 10a} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

Examples of the alkanediyl group represented by R ^1a and R ^2a are the same as those of the alkanediyl group in the description ^{of R 1} and R ^{2 in the formula (II).}

The definitions of R ^3a to ^{R 10a} are the same as those ^{of R 3} to ^{R 10} in formula (II).

Specific examples of compound (IIa) include compounds (II-1) to (II-6), (II-10) to (II-15), and (II-19) to (II-24) shown in Tables 1 to 3 ), (II-28) to (II-33), (II-37) to (II-42), (II-46) to (II-51), (II-55) to (II-60), (II-64) to (II-69), (II-73) to (II-78), (I-82) to (I-87), (I-91) to (I-96), (I -100) to (I-105) and (I-109) to (I-114) are mentioned.

As another preferred embodiment of the compound (II) in the present invention, a compound represented by the following formula (IIb) (hereinafter also referred to as compound (IIb)) is exemplified.

[Formula 13]

[In formula (IIb),

R ^1b and R ^2b each independently represent a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms.

R ^3b to ^{R 10b} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

Examples of the divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by R ^1b and R ^2b include a divalent alicyclic group having 1 to 20 carbon atoms in the description ^{of R 1} and R ^{2 in the above formula (II).} It is the same as the example of a hydrocarbon group.

The definitions of R ^3b to ^{R 10b} are the same as those ^{of R 3} to ^{R 10} in formula (II).

Specific examples of compound (IIb) include compounds (II-9), (II-18), (II-27), (II-36), (II-45), (II-54) shown in Tables 1 to 3 ), (II-63), (II-72), (II-81), (I-90), (I-99), (I-108), (I-117).

As another preferred embodiment of the compound (II) in the present invention, a compound represented by the following formula (IIc) (hereinafter also referred to as compound (IIc)) is exemplified.

[Formula 14]

[In formula (IIc),

R ^1c and R ^2c each independently represent a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms.

R ^3c to ^{R 10c} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

Examples of the divalent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by R ^1c and R ^2c include a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms in the description ^{of R 1} and R ^{2 in the above formula (II).} same as the example of

The definitions of R ^3c to ^{R 10c} are the same as those ^{of R 3} to ^{R 10} in formula (II).

Specific examples of compound (IIc) include compounds (II-7), (II-8), (II-16), (II-17), (II-25), (II-26) shown in Tables 1 to 3 ), (II-34), (II-35), (II-43), (II-44), (II-52), (II-53), (II-61), (II-62), (II-70), (II-71), (II-79), (II-80), (I-88), (I-89), (I-97), (I-98), (I -106), (I-107), (I-115), and (I-116) are mentioned.

Compound (II) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1) in a solvent.

[Formula 15]

[Wherein, R ^{3 to R 10} are the same as defined above.]

[Formula 16]

[In the formula, R represents a divalent hydrocarbon group having 1 to 20 carbon atoms.]

3,4,9,10-perylenetetracarboxylic dianhydride etc. are mentioned as a compound represented by Formula (pt1).

Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms represented by R in the formula (ca1) include the divalent hydrocarbon group having 1 to 20 carbon atoms in the description ^{of R 1} and R ^{2 in the compound (II) above.} It is the same as the example of a hydrocarbon group.

Examples of the compound represented by the formula (ca1) include 2-aminoethanoic acid (glycine), 2-aminopropionic acid, 2-amino-3-methylbutanoic acid, 2-amino-4-methylpentanoic acid, and 2-amino-3- methylpentanoic acid, 4-aminobenzoic acid, and 2-amino-3-phenylpropionic acid.

The amount of the compound represented by formula (ca1) to be used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, more preferably with respect to 1 mol of the compound represented by formula (pt1). They are 1 mole or more and 6 moles or less, and more preferably 1 mole or more and 4 moles or less.

As a solvent, For example, water; nitrile solvents such as acetonitrile; Alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol ; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; Sulfoxide solvents, such as dimethyl sulfoxide, are mentioned.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compounds represented by Formula (pt1).

Reaction temperature is -100 degreeC or more and 300 degrees C or less normally, Preferably they are -90 degreeC or more and 200 degrees C or less, More preferably, they are -10 degreeC or more and 150 degrees C or less.

The method for taking out compound (II) after completion of the reaction is not particularly limited, and can be taken out by various known methods. For example, compound (II) can be taken out by distillation of a solvent. Moreover, after distilling off a solvent, you may refine|purify the obtained residue by column chromatography, recrystallization, etc. In addition, after completion of the reaction, compound (II) can be taken out by filtration. Moreover, after filtration, you may refine|purify the obtained residue by column chromatography, recrystallization, etc. The chemical structure of the obtained compound (II) can be analyzed by a known analysis method and its conditions. Although it does not specifically limit as such an analysis method, X-ray crystal structure analysis method, mass spectrometry (LC), NMR analysis method, an elemental analysis method, etc. are mentioned. The X-ray crystal structure analysis method can be performed based on, for example, Chemistry of Materials, 2012, Vol. 24, p.4647-4652.

Compound (IIa) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1a) (hereinafter also referred to as compound (ca1a)) in a solvent.

[Formula 17]

[In the formula, R ^a represents an alkanediyl group having 1 to 20 carbon atoms.]

Examples of the alkanediyl group having 1 to 20 carbon atoms represented by R ^a are the same as the examples of the alkanediyl group having 1 to 20 carbon atoms in the description ^{of R 1} and R ^{2 in the formula (II).}

Specific examples of the compound (ca1a) include 2-aminoethanoic acid (glycine), 3-aminopropanoic acid, 4-aminobutanoic acid, 5-aminopentanoic acid, 6-aminohexanoic acid, 7-aminoheptanoic acid, and 8-aminoox. Carbonic acid, 9-aminononanoic acid, 10-aminodecanoic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, 13-aminotridecanoic acid, 14-aminotetradecanoic acid, 15-aminopentadecanoic acid, 16- Aminohexadecanoic acid, 17-aminoheptadecanoic acid, 18-aminooctadecanoic acid, 19-aminononadecanoic acid, 20-aminoeicosic acid, 2-aminopropionic acid, 2-amino-3-methylbutanoic acid, 2-amino -4-methylpentanoic acid, 2-amino-3-methylpentanoic acid, etc. are mentioned.

Compound (IIb) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1b) (hereinafter also referred to as compound (ca1b)) in a solvent.

[Formula 18]

[In the formula, R ^b represents a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms.]

Examples of the divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by R ^b include examples of the divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms in the description ^{of R 1} and R ^{2 in formula (II);} same.

Specific examples of the compound (ca1b) include 3-aminocyclopentane-1-carboxylic acid and 3-aminocyclopentane-1-carboxylic acid.

Compound (IIc) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1c) in a solvent.

[Formula 19]

[In the formula, R ^c represents a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms.]

Examples of the divalent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by R ^c are the same as the examples of the divalent aromatic hydrocarbon group having 1 to 20 carbon atoms in the description ^{of R 1} and R ^{2 in formula (II).} .

Specific examples of the compound (ca1c) include 4-aminobenzoic acid and 2-(4-aminophenyl)benzoic acid.

<Colorant (A)>

The content of the compound (I) in the colorant (A) may be, for example, 0.1 mass% or more, preferably 0.5 mass% or more, more preferably 1 mass% or more, with respect to the total amount of the colorant (A). , more preferably 5 mass % or more, particularly preferably 10 mass % or more, still more preferably 20 mass % or more, still more preferably 50 mass % or more, on the other hand, the compound in the colorant (A) The content rate of (I) is usually less than 100 mass % with respect to the total amount of a coloring agent (A), for example, 99 mass % or less may be sufficient.

The content of compound (II) in the colorant (A) may be, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more with respect to the total amount of the colorant (A). , more preferably 5 mass % or more, particularly preferably 10 mass % or more, still more preferably 20 mass % or more, while the content of compound (II) in the colorant (A) is, the colorant (A) It is usually less than 100 mass % with respect to the total amount, for example, 99 mass % or less may be sufficient.

As a mass ratio of compound (I) and compound (II) in a coloring agent (A), 1:99-99:1 may be sufficient, for example, Preferably it is 20:80-80:20, More preferably, 30:70 -70:30, more preferably 40:60-60:40. When the mass ratio of the compound (I) and the compound (II) in the coloring agent (A) is within the above range, the dispersibility of the compound (I) in the coloring composition improves, and there exists a tendency for heat resistance to improve easily.

The content rate of the coloring agent (A) in the coloring composition may be, for example, 0.1 mass % or more and 99.9 mass % or less, preferably 0.5 mass % or more and 99 mass % or less, with respect to the total amount of solid content in the coloring composition, more preferably is 1 mass % or more and 90 mass % or less, More preferably 5 mass % or more and 80 mass % or less, Especially preferably 10 mass % or more and 70 mass % or less, More preferably, 15 mass % or more and 60 mass % or less or less, still more preferably 20% by mass or more and 50% by mass or less, particularly preferably 25% by mass or more and 45% by mass or less, and extremely preferably 30% by mass or more and 40% by mass or less.

In this specification, "the total amount of solid content in a coloring composition" means the total amount of the component except all the solvent components from the coloring composition. The total amount of solid content and content of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography.

<Colorant (A1)>

A coloring agent (A1) may be dye or a pigment may be sufficient as it. As dye, a well-known dye can be used, For example, the well-known dye described in the color index (published by The Society of Dyers and Colors) and the dyeing notebook (Shikisensha) is mentioned. Further, according to the chemical structure, azo dye, cyanine dye, triphenylmethane dye, xanthene dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine Dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, etc. are mentioned. You may use these dyes individually or in combination of 2 or more types.

Specifically, the dye of the following color index (C.I.) numbers is mentioned.

C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;

C.I. Solvent Red 24, 45, 49, 90, 91111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. C.I. solvent dyes,

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;

C.I. acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 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, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

C.I. 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, CIs of 104, 105, 106, 109, etc. acid dye,

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

C.I. 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;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

C.I. 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, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82, etc. C.I. direct dye,

C.I. Disperse Yellow 51, 54, 76;

C.I. Disperse Violet 26, 27;

C.I. Disperse Blue 1, 14, 56, 60, etc. C.I. dispers dye,

C.I. Basic Red 1, 10;

C.I. 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;

C.I. Basic Violet 2;

C.I. Basic Red 9;

C.I. Basic Green 1; et al. C.I. basic dye,

C.I. Reactive Yellow 2, 76, 116;

C.I. Reactive Orange 16;

C.I. Reactive Red 36; et al. C.I. reactive dyes,

C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

C.I. Modern Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

C.I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

C.I. Modern Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;

C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. C.I. modern dye,

C.I. Bat Green 1, etc. C.I. bat dye, etc.

Moreover, Lumogen (trademark) F Yellow 083 (made by BASF), Lumogen (trademark) F Yellow 170 (made by BASF), and Lumogen (trademark) F Red 305 (made by BASF) are mentioned.

As a pigment, a well-known pigment can be used, For example, the pigment classified into the pigment by the color index (The Society of Dyers and Colorists publication) is mentioned. These may be used independently and may be used in combination of 2 or more type.

Specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138 , 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231 yellow pigments;

C.I. Orange pigments, such as pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264 Red pigments, such as 265, 266, 268, 269, 273;

C.I. Blue pigments, such as pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;

C.I. Violet pigments, such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Green pigments, such as Pigment Green 7, 36, 58, 59, 62, 63;

C.I. Brown pigments, such as Pigment Brown 23 and 25;

C.I. Black pigments, such as pigment black 1, 7, 31, and 32, are mentioned.

The colorant (A1) is, if necessary, a rosin treatment, a surface treatment using a derivative into which an acidic group or a basic group is introduced, a graft treatment to the surface of the colorant (A1) with a polymer compound, etc., atomization treatment by a sulfuric acid atomization method, etc.; Washing treatment with an organic solvent, water, etc. for removing impurities, removal treatment of ionic impurities by an ion exchange method, etc. may be performed. It is preferable that the particle diameter of a coloring agent (A1) is substantially uniform.

When the colorant (A) further contains the colorant (A1), the lower limit of the content of the total amount of the compound (I) and the compound (II) in the colorant (A) is usually 1% by mass based on the total amount of the colorant (A). More preferably, it is 2 mass % or more, More preferably, it is 10 mass % or more, More preferably, it is 25 mass % or more, Especially preferably, it is 50 mass % or more. On the other hand, the upper limit of the content rate of the total amount of compound (I) and compound (II) in a coloring agent (A) is 100 mass % or less normally with respect to the total amount of a coloring agent (A).

When the coloring agent (A) further contains the coloring agent (A1), the content rate of the coloring agent (A) in the coloring composition is usually 0.1% by mass or more and 99% by mass or less with respect to the total amount of solid content in the coloring composition, for example, 0.1 It may be mass % or more and 90 mass % or less, Preferably it is 0.5 mass % or more and 80 mass % or less, More preferably, it is 0.7 mass % or more and 70 mass % or less, Especially preferably, it is 1 mass % or more and 60 mass % or less. am.

When a coloring composition contains a solvent (E), after preparing the coloring agent containing liquid containing a coloring agent (A) and a solvent (E) previously, you may prepare a coloring composition using the said coloring agent containing liquid. When a coloring agent (A) does not melt|dissolve in a solvent (E), a coloring agent containing liquid can be prepared by disperse|distributing a coloring agent (A) to a solvent (E), and mixing it. The coloring agent containing liquid may contain a part or all of the solvent (E) contained in a coloring composition.

The content of solid content in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, more preferably 0.1% by mass or more with respect to the total amount of the colorant-containing liquid. 99% by mass or less, particularly preferably 1% by mass or more and 90% by mass or less, still more preferably 1% by mass or more and 60% or less, still more preferably 3% by mass or more and 50% by mass or less, particularly preferably is 3% by mass or more and 30% by mass or less, and extremely preferably 5% by mass or more and 30% by mass or less.

The content rate of the colorant (A) in the colorant-containing liquid is usually less than 100% by mass, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.01% by mass or more and 99 in the total amount of solid content in the colorant-containing liquid. It is mass % or less, More preferably, they are 0.1 mass % or more and 99 mass % or less, Especially preferably, they are 1 mass % or more and 99 mass % or less, More preferably, they are 2 mass % or more and 99 mass % or less.

In this specification, "the total amount of solid content in the coloring agent containing liquid" means the total amount of the component except the solvent (E) from the coloring agent containing liquid. The total amount of solid content and content of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography.

The coloring agent (A) can be made into the state which disperse|distributed the coloring agent (A) uniformly in the coloring agent containing liquid by making it contain a dispersing agent and performing a dispersion process. A coloring agent (A) may carry out a dispersion process independently, respectively, and may mix and disperse|distribute multiple types.

Surfactants etc. are mentioned as a dispersing agent, Any surfactant of cationic, anionic, nonionic, and amphoteric type may be sufficient. Specifically, surfactants, such as a polyester type, a polyamine type, and an acryl type, etc. are mentioned. You may use these dispersing agents individually or in combination of 2 or more types. As a dispersing agent, when it shows by a brand name, KP (made by Shin-Etsu Chemical Co., Ltd.), Florene (made by Kyoeisha Chemical Co., Ltd.), Solsperse (trademark) (made by Zeneca Co., Ltd.), EFKA (trademark) (manufactured by BASF Co., Ltd.), Azispa (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by Big Chemi Co., Ltd.), BYK (registered trademark) (manufactured by Big Chemi Co., Ltd.) ) and the like.

When a dispersing agent is used to prepare the colorant-containing liquid, the amount of the dispersant (solid content) used is usually 10,000 parts by mass or less, preferably 5000 parts by mass or less, with respect to 100 parts by mass of the colorant (A), more Preferably it is 1000 mass parts or less, More preferably, it is 500 mass parts or less, Especially preferably, it is 300 mass parts or less, More preferably, it is 200 mass parts or less, More preferably, it is 5 mass parts or more and 150 mass parts. It is a part or less, Especially preferably, they are 5 mass parts or more and 110 mass parts or less. When the usage-amount of the said dispersing agent exists in the said range, there exists a tendency for the coloring agent containing liquid in a more uniformly dispersed state to be obtained.

<Resin (B)>

The resin (B) is preferably an alkali-soluble resin, and is derived from at least one monomer (hereinafter sometimes referred to as “monomer (a)”) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride. It is more preferable that it is a polymer which has a structural unit.

The resin (B) is a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b)”), and other structural units. chain is preferred.

As another structural unit, the structural unit derived from the monomer copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b). Hereinafter, it may be referred to as "monomer (c)"), ethylene The structural unit etc. which have a sex unsaturated bond are mentioned.

As a monomer (a), For example, unsaturated monocarboxylic acids, such as acrylic acid, methacrylic acid, a crotonic acid, and o-, m-, p-vinyl benzoic acid;

Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid;

Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene , a bicyclo unsaturated compound containing a carboxyl group, such as 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2-ene;

carboxylic acid anhydrides such as anhydrides of the above unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;

Unsaturated mono [(meth) acryloyloxyalkyl] of polyhydric carboxylic acids with divalence or higher, such as mono[2-(meth)acryloyloxyethyl succinate] and mono[2-(meth)acryloyloxyethyl] phthalate esters;

and unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from the point of copolymerization reactivity and the solubility point to the aqueous alkali solution of resin obtained.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. say The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

As the monomer (b), for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter “monomer”) (b2)") and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b3)"), etc. are mentioned.

As the monomer (b1), for example, a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “monomer (b1-1)”) and an alicyclic unsaturated hydrocarbon are epoxy and a monomer (hereinafter, sometimes referred to as "monomer (b1-2)") having a modified structure.

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.

Specific examples of the monomer (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, and glycidyl vinyl ether. , Vinylbenzylglycidyl ether, α-methylvinylbenzylglycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5- Bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycy diloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene methyl) styrene and the like.

As the monomer (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxy Cyclohexylmethyl (meth) acrylate (eg, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, Cyclomer (registered) Trademark) M100 (manufactured by Daicel Corporation), the compound represented by the formula (BI), the compound represented by the formula (BII), and the like.

[Formula 20]

[In formulas (BI) and (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, even if the hydrogen atom contained in the alkyl group is substituted with a hydroxy group do.

X ^a and X ^b each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.

R ^c represents a C1-C6 alkanediyl group.

* indicates a bond with O.]

Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.

Examples of the alkyl group in which a hydrogen atom is substituted with hydroxy include a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, and 3-hydroxypropyl group. , 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, etc. can be heard

R ^a and R ^b preferably include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1,5-diyl group. , a hexane-1,6-diyl group, and the like.

As X ^a and X ^b , Preferably, a single bond, a methylene group, an ethylene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O- are mentioned, More preferably, a single bond, *- CH ₂ CH ₂ -O- is mentioned (* indicates a bond with O).

Examples of the compound represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among them, formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15) ) is preferable, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferable.

[Formula 21]

Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), and among these, formula (BII-1), formula ( BII-3), a compound represented by a formula (BII-5), a formula (BII-7), a formula (BII-9), and a formula (BII-11) - a formula (BII-15) are mentioned, More preferable Examples thereof include compounds represented by formulas (BII-1), (BII-7), (BII-9) and (BII-15).

[Formula 22]

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone, or the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. When these are used together, the content ratio of the compound represented by the formula (BI) and the compound represented by the formula (BII) is, on a molar basis, preferably 5:95 to 95:5, more preferably 10:90 to It is 90:10, More preferably, it is 20:80-80:20.

As a monomer (b2), the monomer which has an oxetanyl group and a (meth)acryloyloxy group is more preferable.

As the monomer (b2), for example, 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxy Methyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl -3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. are mentioned.

As a monomer (b3), the monomer which has a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable.

As a monomer (b3), tetrahydrofurfuryl acrylate (For example, Viscoat V#150, Osaka Organic Chemical Co., Ltd. product), tetrahydrofurfuryl methacrylate etc. are mentioned, for example.

As a monomer (b), it is preferable that it is a monomer (b1) from the point which can improve reliability, such as the heat resistance of the color filter obtained, chemical-resistance, etc. more. Moreover, a monomer (b1-2) is more preferable at the point which is excellent in the storage stability of a coloring composition.

As the monomer (c), for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate , 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate , 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-9-yl (meth) ) acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, dicyclopentanyloxy Ethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth)acrylic acid esters, such as (meth)acrylate and benzyl (meth)acrylate;

hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;

Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybi Cyclo[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, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept- 2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methyl Bicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxy Cycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexylox) bicyclo unsaturated compounds such as cycarbonyl)bicyclo[2.2.1]hept-2-ene;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutylate, N-succinimidyl dicarbonylimide derivatives such as -6-maleimide caproate, N-succinimidyl-3-maleimide propionate and N-(9-acridinyl)maleimide;

Vinyl group-containing aromatic compounds, such as styrene, (alpha)-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; and the like.

Of these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate, and tricyclo[5.2.1.0 ^2,6 ]decane-9 -yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-9-yl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, benzyl (meth)acrylate, and the like are preferable.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. The resin having such a structural unit is a monomer having an ethylenically unsaturated bond in a group capable of reacting with the group of the monomer (a) or the monomer (b) in a polymer having a structural unit derived from the monomer (a) or the monomer (b). It can be obtained by adding

As such a structural unit, the structural unit which added glycidyl (meth)acrylate to the (meth)acrylic acid unit, the structural unit which added 2-hydroxyethyl (meth)acrylate to the maleic anhydride unit, and glycidyl The structural unit etc. which added (meth)acrylic acid to the (meth)acrylate unit are mentioned. Moreover, when such a structural unit has a hydroxyl group, the structural unit which further added carboxylic acid anhydride is also mentioned as a structural unit which has an ethylenically unsaturated bond.

The polymer having a structural unit derived from the monomer (a) can be produced, for example, by polymerization of a monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. A polymerization initiator, a solvent, etc. are not specifically limited, What is normally used in the said field|area can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) ) are mentioned, and what is necessary is just to melt|dissolve each monomer as a solvent.

In addition, the obtained polymer may use the solution after reaction as it is, may use the concentrated or diluted solution, and may use what was taken out as solid (powder) by methods, such as reprecipitation.

If necessary, a catalyst for the reaction of carboxylic acid or carboxylic acid anhydride with a cyclic ether (for example, tris(dimethylaminomethyl)phenol), a polymerization inhibitor (for example, hydroquinone, etc.), etc. may be used.

Examples of the carboxylic anhydride include 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-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. are mentioned.

Specifically as the resin (B), 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acryl rate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ( meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/2-ethylhexyl(meth)acryl Late copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / tricyclo [5.2.1.0 ^2,6 ] decenyl (meth) acrylate / (meth) acrylic acid / N -Cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl(meth)acrylate/(meth)acrylic acid copolymer, styrene/ (meth)acrylic acid copolymer and the resin of each publication of Unexamined-Japanese-Patent No. 9-106071, Unexamined-Japanese-Patent No. 2004-29518, and Unexamined-Japanese-Patent No. 2004-361455, etc. are mentioned.

Especially, as resin (B), the copolymer containing the structural unit derived from the monomer (a) and the structural unit derived from the monomer (b) is preferable.

Resin (B) may combine 2 or more types, and in this case, resin (B) is at least 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth) Acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl(meth)acrylate copolymer , 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ( It is preferable to include at least one selected from meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

The weight average molecular weight (Mw) in terms of polystyrene of the resin (B) is preferably 1,000 or more and 100,000 or less, more preferably 1,000 or more and 50,000 or less, still more preferably 1,000 or more and 30,000 or less, particularly preferably 3000 more than 30000 and less than

The molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, still more preferably 1.01 or more and 4 or less. is below.

The acid value (in terms of solid content) of the resin (B) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, still more preferably 20 mg-KOH/g or more and 200 mg-KOH/g or less, particularly preferably 20 mg-KOH/g or more and 170 mg-KOH/g or less, still more preferably 30 mg-KOH/g or more and 170 mg-KOH/g or less, particularly preferably is 60 mg-KOH/g or more and 150 mg-KOH/g or less, and extremely preferably 65 mg-KOH/g or more and 135 mg-KOH/g or less. Here, an acid value is a value measured as the quantity (mg) of potassium hydroxide required for neutralizing 1 g of resin (B), For example, it can obtain|require by titrating using potassium hydroxide aqueous solution.

In the coloring composition, the content of the resin (B) may be, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 0.5% by mass or more and 99% by mass or less, more preferably with respect to the total amount of solid content in the coloring composition. is 1 mass % or more and 95 mass % or less, More preferably 2 mass % or more and 90 mass % or less, Especially preferably 3 mass % or more and 80 mass % or less, More preferably, 5 mass % or more and 70 mass % or less and still more preferably 7 mass % or more and 60 mass % or less, particularly preferably 10 mass % or more and 50 mass % or less, and extremely preferably 10 mass % or more and 30 mass % or less.

After preparing the colorant-containing liquid in advance, when the coloring composition of the present invention is prepared using the colorant-containing liquid, the colorant-containing liquid is a part or all of, preferably part of, the resin (B) described later contained in the coloring composition. may be included in advance. By including the resin (B) in advance, the dispersion stability of the colorant-containing liquid can be further improved.

The content of the resin (B) in the colorant-containing liquid may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less with respect to 100 parts by mass of the colorant (A). , More preferably, they are 1 mass part or more and 500 mass parts or less, Especially preferably, they are 5 mass parts or more and 200 mass parts or less, More preferably, they are 10 mass parts or more and 100 mass parts or less.

<Embodiment 1>

The coloring composition which concerns on Embodiment 1 is a coloring composition containing a coloring agent (A) and resin (B), The coloring agent (A) is represented by the compound represented by Formula (I), and following formula (IIa), It is a coloring composition containing the oily compound.

[Formula 23]

[In formula (IIa), ^{the definitions of R 1a} to ^{R 10a} are the same as those described above.]

Examples and preferred ranges of each content rate of compound (I) and compound (IIa) in the colorant (A) are the same as the examples and preferred ranges of each content rate of compound (I) and compound (II) in the colorant (A) described above. do.

<Embodiment 2>

The coloring composition which concerns on Embodiment 2 is a coloring composition containing a coloring agent (A) and resin (B), Comprising: The coloring agent (A) is represented by the compound represented by Formula (I), and following formula (IIb), It is a coloring composition containing the oily compound.

[Formula 24]

[In formula (IIb), ^{the definitions of R 1b} to ^{R 10b} are the same as those described above.]

Examples and preferred ranges of each content rate of compound (I) and compound (IIb) in the colorant (A) are the same as the examples and preferred ranges of each content rate of compound (I) and compound (II) in the colorant (A) described above. do.

<Embodiment 3>

The coloring composition which concerns on Embodiment 3 is a coloring composition containing a coloring agent (A) and resin (B), Comprising: It is a coloring composition in which a coloring agent (A) contains compound (IIc).

[Formula 25]

[In formula (IIc), ^{the definitions of R 1c} to ^{R 10c} are the same as the definitions described above.]

Examples and preferred ranges of each content rate of compound (I) and compound (IIc) in the colorant (A) are the same as the examples and preferred ranges of each content rate of compound (I) and compound (II) in the colorant (A) described above. do.

(2) Colored curable resin composition

The colored curable resin composition comprises a compound (I), a compound (II), a resin (B) (hereinafter, collectively referred to as a colorant (A)), a polymerizable compound (hereinafter referred to as a polymerizable compound (C)) In some cases) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)) are included.

The colored curable resin composition is selected from the group consisting of a leveling material (hereinafter, may be referred to as a leveling material (F)), an antioxidant (hereinafter may be referred to as an antioxidant (G)), and a solvent (E) You may include 1 type more.

Although the content rate of solid content in the coloring composition contained in colored curable resin composition is not specifically limited since it is suitably adjusted according to the chromaticity, brightness, film thickness, etc. required when hardening colored curable resin composition, The total amount of solid content in colored curable resin composition Based on, for example, 1 mass % or more and 99 mass % or less may be sufficient, Preferably it is 1 mass % or more and 90 mass % or less, More preferably, it is 2 mass % or more and 80 mass % or less, More preferably 3 mass % or more and 70 mass % or less, particularly preferably 4 mass % or more and 60 mass % or less, still more preferably 5 mass % or more and 50 mass % or less, particularly preferably 6 mass % or more and 45 mass % or less , Very preferably, it is 7 mass % or more and 40 mass % or less.

Each content rate of the colorant (A) in the colored curable resin composition is not particularly limited because it is appropriately adjusted depending on the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured, but in the total amount of solid content in the colored curable resin composition , For example, 0.1 mass% or more and 99 mass% or less may be sufficient, Preferably it is 1 mass % or more and 90 mass % or less, More preferably, it is 2 mass % or more and 80 mass % or less, More preferably, it is 3 mass % or more. 70 mass % or less, Especially preferably 4 mass % or more and 60 mass % or less, More preferably 5 mass % or more and 50 mass % or less, Especially preferably 8 mass % or more and 40 mass % or less, extremely preferable Preferably, it is 10 mass % or more and 30 mass % or less.

In this specification, "the total amount of solid content in colored curable resin composition" means the total amount of the component except the solvent (E) from colored curable resin composition. The total amount of solid content and content of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography. The content rate of solid content in colored curable resin composition may be 0.01 mass % or more and less than 100 mass % with respect to the total amount of colored curable resin composition, Preferably, 0.1 mass % or more and 99.9 mass % or less, More preferably 0.1 It is mass % or more and 99 mass % or less, Especially preferably, it is 1 mass % or more and 60 mass % or less, More preferably, it is 3 mass % or more and 50 mass % or less, More preferably, it is 3 mass % or more and 30 mass % or less. , Especially preferably, it is 5 mass % or more and 30 mass % or less.

The colored pattern or colored coating film described later formed from the colored curable resin composition of the present invention is not only excellent in heat resistance, but also tends to have a high transmittance at a wavelength of 630 nm, and preferably contains the compound (I) alone. The transmittance|permeability in wavelength 630nm tends to be high compared with the coloring pattern and colored coating film formed from curable resin composition. The transmittance at a wavelength of 630 nm may be, for example, 90% or more, preferably 95% or more, and more preferably 97% or more of the colored pattern or colored coating film described later formed from the colored curable resin composition of the present invention. . The transmittance at a wavelength of 630 nm can be measured using, for example, a colorimeter (OSP-SP-200; manufactured by OLYMPUS).

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized with an active radical and/or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, preferably ( It is a meth)acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, and 2-hydroxy Ethyl acrylate, N-vinylpyrrolidone, etc., and the above-mentioned monomer (a), monomer (b), and monomer (c) are mentioned.

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tri Ethylene glycol di(meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc. are mentioned.

Especially, it is preferable that a polymeric compound (C) is a polymeric compound which has three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol penta(meth)acrylate. Pentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth) ) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate, preferably Dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are mentioned.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4000 or less, more preferably 50 or more and 3500 or less, still more preferably 50 or more and 3000 or less, particularly preferably 150 or more and 2,900 or less. , particularly preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 2% by mass or more and 90% by mass or less, with respect to the total amount of solid content in the colored curable resin composition, more Preferably it is 3 mass % or more and 80 mass % or less, More preferably, it is 4 mass % or more and 70 mass % or less, Especially preferably, it is 5 mass % or more and 60 mass % or less, More preferably, it is 6 mass % or more and 50 mass % or less. It is mass % or less, Especially preferably, they are 7 mass % or more and 40 mass % or less.

<Polymerization Initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating an active radical, an acid, etc. under the action of light or heat, and a known polymerization initiator can be used.

As a polymerization initiator (D), an O-acyl oxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, an acylphosphine oxide compound, etc. are mentioned.

As the O-acyloxime compound, for example, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl) ) Octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4 -Phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine , N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6 -{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1 -[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine and N-benzoyloxy-1-[9-ethyl-6-( 2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine and the like. Moreover, as an O-acyl oxime compound, you may use commercial items, such as Irgacure OXE01, OXE02 (above, BASF Corporation make), and N-1919 (made by ADEKA Corporation). Among them, examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl). At least one selected from the group consisting of octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferable , N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferable.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzyl butan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one; and the like. As an alkylphenone compound, you may use commercial items, such as Irgacure 369, 907, 379 (above, BASF Co., Ltd. product).

Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1 -one, 1-hydroxycyclohexylphenylketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyldimethyl Ketals are also included.

As the biimidazole compound, 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 Laid-Open No. 6-75372, Japanese Patent Application Laid-Open 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. , Japanese Patent Application Laid-Open No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.) and biimi in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group. Dazole compounds (for example, refer to Unexamined-Japanese-Patent No. 7-10913, etc.) etc. are mentioned.

Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4 -Methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloro) To methyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl) tenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2, 4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6 -[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine etc. are mentioned.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. You may use commercial items, such as Irgacure (trademark) 819 (made by BASF Corporation).

Furthermore, as a polymerization initiator (D), Benzoin compounds, such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Benzophenone, o-benzoylbenzoate methyl, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone and benzophenone compounds such as 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compound, and the like.

It is preferable to use these in combination with the polymerization initiation adjuvant (D1) (especially amines) mentioned later.

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

The content rate of the polymerization initiator (D) may be, for example, 0.01 mass% or more and 40 mass% or less, with respect to the total amount of all the resins (B) and the polymerizable compound (C) contained in the colored curable resin composition, preferably 0.1 mass % or more and 35 mass % or less.

<Polymerization initiation aid (D1)>

A polymerization initiation adjuvant (D1) is a compound used in order to accelerate|stimulate superposition|polymerization of the polymeric compound which superposition|polymerization was started by a polymerization initiator, or a sensitizer. When a polymerization initiation adjuvant (D1) is included, it is used in combination with a polymerization initiator (D) normally.

As polymerization initiation adjuvant (D1), an amine compound, an alkoxyanthracene compound, a thioxanthone compound, a carboxylic acid compound, etc. are mentioned.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and 4-dimethylaminobenzoic acid. 2-ethylhexyl, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4' -bis(ethylmethylamino)benzophenone etc. are mentioned, Preferably 4,4'-bis(diethylamino)benzophenone is mentioned. Moreover, as an amine compound, you may use commercial items, such as EAB-F (made by Hodogaya Chemical Industry Co., Ltd.).

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibu thoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene; and the like.

Examples of the thioxanthone compound include 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxy Oxanthone etc. are mentioned.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenyl Sulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc. are mentioned.

When using such a polymerization initiation adjuvant (D1), the content rate may be, for example, 0.01 mass % or more and 40 mass % or less with respect to the total amount of resin (B) and polymeric compound (C), Preferably 0.1 mass % or more and 30 mass % or less.

<Solvent (E)>

The solvent (E) is, for example, an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), an ether solvent (containing -O- in the molecule and not containing -COO-), for example. solvent), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (OH in the molecule) and solvents that do not contain -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

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

As the ether solvent, 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, phenetol and methylanisole and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, and methyl 3-ethoxypropionate. , 3-ethoxypropionate ethyl, 2-methoxypropionate methyl, 2-methoxypropionate ethyl, 2-methoxypropionate propyl, 2-ethoxypropionate methyl, 2-ethoxypropionate ethyl, 2-methoxy-2- Methyl methyl propionate, 2-ethoxy-2-methyl ethyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono and propyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

As a ketone solvent, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclo pentanone, cyclohexanone, isophorone, and the like.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

As an aromatic hydrocarbon solvent, benzene, toluene, xylene, mesitylene, etc. are mentioned.

Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.

These solvents may use 2 or more types together.

The content rate of a solvent (E) is 99.99 mass % or less normally with respect to the total amount of colored curable resin composition, Preferably it is 0.1 mass % or more and 99.9 mass % or less, More preferably, it is 1 mass % or more and 99.9 mass % or less. , More preferably, it is 10 mass % or more and 99 mass % or less, Especially preferably, it is 40 mass % or more and 99 mass % or less, More preferably, it is 50 mass % or more and 90 mass % or less, Especially preferably, it is 60 mass %. It is 95 mass % or more, More preferably, it is 70 mass % or more and 90 mass % or less.

The colored curable resin composition of the present invention is prepared by dispersing all or a part of the compound (I) and the compound (II) in all or a part of the solvent (E) to prepare a colorant-containing liquid, and then using this colorant-containing liquid You can do it.

The content rate of solid content in the colorant-containing liquid may be, for example, 0.01% by mass or more and 99.99% by mass or less, preferably 0.1% by mass or more and 99.9% by mass or less, more preferably 0.1% by mass relative to the total amount of the colorant-containing liquid. % or more and 99 mass % or less, more preferably 1 mass % or more and 90 mass % or less, more preferably 1 mass % or more and 60 mass % or less, still more preferably 3 mass % or more and 50 mass % or less, especially Preferably they are 3 mass % or more and 30 mass % or less, Very preferably, they are 5 mass % or more and 30 mass % or less.

The total content of compound (I) and compound (II) in the colorant-containing liquid may be, for example, 0.0001% by mass or more, preferably 0.01% by mass or more, more preferably 1, based on the total amount of solid content in the colored dispersion. It is mass % or more, More preferably, it is 5 mass % or more, More preferably, it is 10 mass % or more, More preferably, it is 20 mass % or more, Especially preferably, it is 30 mass % or more. On the other hand, the upper limit of the total content of compound (I) and compound (II) in the colorant-containing liquid is usually less than 100% by mass, for example, 99% by mass or less, in the total amount of solid content in the colorant-containing liquid.

When all or part of compound (I) and compound (II) are dispersed in all or part of solvent (E) to prepare a colorant-containing liquid, all or part of resin (B) is included to contain a colorant The dispersion stability of the liquid can be further improved. The content of the resin (B) in the colorant-containing liquid is, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 100 parts by mass or less in total of 100 parts by mass of the compound (I) and the compound (II). is 1000 parts by mass or less, more preferably 1 parts by mass or more and 500 parts by mass or less, particularly preferably 5 parts by mass or more and 200 parts by mass or less, and still more preferably 10 parts by mass or more and 100 parts by mass or less.

Compound (I) and compound (II), if necessary, rosin treatment, surface treatment using a derivative into which an acidic group or basic group is introduced, grafting onto the surface of compound (I) and compound (II) with a high molecular compound or the like Treatment, atomization treatment by a sulfuric acid atomization method, etc., washing treatment with an organic solvent or water for removing impurities, removal treatment by ion exchange method of ionic impurities, etc. may be performed. It is preferable that the particle diameters of compound (I) and compound (II) are substantially uniform.

Compound (I) and compound (II) can be uniformly dispersed in a colored dispersion by subjecting the compound (I) and compound (II) to dispersion treatment containing a dispersing agent. Compound (I) and compound (II) may be each individually subjected to a dispersion treatment, or a plurality of types may be mixed and dispersed. When the colorant (A) contains the compound (I), the compound (II), and the dispersing agent, the dispersibility of the compound (I) tends to improve.

Surfactants etc. are mentioned as a dispersing agent, Any surfactant of cationic, anionic, nonionic, and amphoteric type may be sufficient. Specifically, surfactants, such as a polyester type, a polyamine type, and an acryl type, etc. are mentioned. You may use these dispersing agents individually or in combination of 2 or more types. As a dispersing agent, when it shows by a brand name, KP (made by Shin-Etsu Chemical Co., Ltd.), Florene (made by Kyoeisha Chemical Co., Ltd.), Solsperse (trademark) (made by Zeneca Co., Ltd.), EFKA (trademark) (manufactured by BASF Co., Ltd.), Azispa (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by Big Chemi Co., Ltd.), BYK (registered trademark) (manufactured by Big Chemi Co., Ltd.) ) and the like.

When using a dispersing agent, the usage-amount of a dispersing agent (solid content) is 10000 mass parts or less with respect to a total of 100 mass parts of compound (I) and compound (II), Preferably it is 5000 mass parts or less, More preferably, it is 1000 mass parts by mass or less, more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, still more preferably 100 parts by mass or less, still more preferably 5 parts by mass or more and 100 parts by mass or less, particularly Preferably they are 5 mass parts or more and 50 mass parts or less. When the usage-amount of a dispersing agent exists in the said range, there exists a tendency for the colored dispersion liquid in a more uniformly dispersed state to be obtained.

The colored curable resin composition of this invention may also contain a leveling agent (F) and antioxidant (G) further.

<Leveling agent (F)>

As a leveling agent (F), a silicone type surfactant, the silicone type surfactant etc. which have a silicone type surfactant, a fluorine type surfactant, and a fluorine atom are mentioned. These may have a polymeric group in a side chain.

As a silicone type surfactant, the surfactant etc. which have a siloxane bond in a molecule|numerator are mentioned. Specifically, Toray Silicon DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan Joint Stock Company), etc. can

As a fluorine-type surfactant, the surfactant etc. which have a fluorocarbon chain in a molecule|numerator are mentioned. Specifically, Florad (registered trademark) FC430, copper FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megapac (registered trademark) F142D, east F171, east F172, east F173, east F177, east F183, east F554, east R30, RS-718-K (manufactured by DIC Co., Ltd.), EFTO (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electric Chemical Co., Ltd.), Saffron (registered trademark) S381 , copper S382, copper SC101, copper SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Institute), and the like.

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megapac (trademark) R08, Dong BL20, Dong F475, Dong F477, Dong F443 (DIC Co., Ltd. product), etc. are mentioned.

When containing a leveling agent (F), the content is 0.0005 mass % or more and 5 mass % or less normally with respect to the total amount of colored curable resin composition, Preferably they are 0.001 mass % or more and 1 mass %, More preferably They are 0.001 mass % or more and 0.5 mass % or less, More preferably, they are 0.002 mass % or more and 0.2 mass % or less, Especially preferably, they are 0.005 mass % or more and 0.1 mass % or less. When content of a leveling agent (F) exists in said range, the flatness of a color filter can be made favorable.

<Antioxidant (G)>

From a viewpoint of improving the heat resistance of a coloring agent, it is preferable to use antioxidant (G) individually or in combination of 2 or more types. The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like can be used.

Examples of the phenolic antioxidant include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF ( Co.), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, BASF Co., Ltd.), Irganox 1330 (Irganox 1330:3,3',3'',5,5',5''-hexa-tert-butyl-a,a',a''-(mesitylene-2,4,6-triyl) Tri-p-cresol, manufactured by BASF Co., Ltd.), Irganox 3114 (Irganox 3114:1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3, 5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), Irganox 3790 (Irganox 3790:1,3,5-tris((4-tert-butyl) -3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), Irga Nox 1035 (Irganox 1035: thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF Co., Ltd.), Irganox 1135 (Irganox 1135: Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 branched alkyl ester, manufactured by BASF Co., Ltd., Irganox 1520L (Irganox 1520L: 4,6-bis (octylthiomethyl)-o-cresol, manufactured by BASF Co., Ltd.), Irganox 3125 (Irganox 3125, manufactured by BASF), Irganox 565 (Irganox 565: 2,4-bis (n-octylthio) )-6-(4-hydroxy 3',5'-di-tert-butylanilino)-1,3,5-triazine, BASF Co., Ltd. product), adecastab AO-80 (adecastab AO-80:3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8, 10-tetraoxaspiro (5,5) undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (Sumitomo Chemical Co., Ltd.) , Sumilizer GA-80 (Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (Cyanox 1790, manufactured by Cytech) and vitamin E (manufactured by Eisai Co., Ltd.); and the like.

As said phosphorus antioxidant, Irgafos 168 (Irgafos 168: tris (2,4-di-tert- butylphenyl) phosphite, BASF Co., Ltd. product), Irgafos 12 (Irgafos 12: tris) is, for example, [2-[[2,4,8,10-tetra-tert-butylbenzo[d,f][1,3,2]dioxaphosphin-6-yl]oxy]ethyl]amine, BASF Corporation ), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Co., Ltd.), adecastab 329K (Co., Ltd.) ADEKA), ADEKA STAB PEP36 (made by ADEKA), ADEKA STAB PEP-8 (made by ADEKA), Sandstab P-EPQ (made by Clariant), Weston 618 (Weston 618, manufactured by GE), Weston 619G (Weston 619G, manufactured by GE), Ultranox 626 (Ultranox 626, manufactured by GE) and Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy]-2,4,8,10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphospepine) (manufactured by Sumitomo Chemical Co., Ltd.); and the like.

Examples of the sulfur-based antioxidant include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and tetrakis[methylene(3-dodecylthio)propionate] and β-alkyl mercaptopropionic acid ester compounds of polyols such as methane.

<Other ingredients>

The colored curable resin composition of this invention may contain well-known additives in this technical field, such as a filler, another high molecular compound, an adhesion promoter, an optical stabilizer, and a chain transfer agent, as needed.

As the adhesion promoter, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropyl Methyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane , 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2-(aminoethyl )-3-Aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2 -(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl- 3-aminopropyl triethoxysilane etc. are mentioned.

<Method for producing colored curable resin composition>

Colored curable resin composition, when patterning a coloring agent (A), resin (B), a solvent (E), and a leveling agent (F) by the photolitho method, for example, a polymeric compound (C) , it can prepare by mixing with a polymerization initiator (D), a polymerization initiation auxiliary|assistant (D1), and another component.

It is preferable to mix a pigment with a part or all of a solvent (E) beforehand, and to disperse|distribute using a bead mill etc. until the average particle diameter of a pigment becomes about 0.2 micrometer or less. At this time, you may mix|blend a part or all of the said pigment dispersant and resin (B) as needed. The target colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid obtained in this way so that it may become predetermined density|concentration.

The dye may be previously dissolved in a part or all of the solvent (E) to prepare a solution. It is preferable to filter the said solution with a filter of about 0.01 micrometer or more and 1 micrometer or less of pore diameter.

It is preferable to filter the colored curable resin composition after mixing with a filter with a pore diameter of about 0.1 micrometer or more and 10 micrometers or less.

(3) color filter

A color filter can be formed from the colored curable resin composition of this invention. A photolithographic method, an inkjet method, a printing method, etc. are mentioned as a method of forming a coloring pattern. Especially, the photolithographic method is preferable. The photolithography method is a method of apply|coating the said colored curable resin composition to a board|substrate, drying it, forming a colored curable resin composition layer, exposing the said colored curable resin composition layer through a photomask, and developing. In the photolithography method, the colored coating film which is the hardened|cured material of the said colored curable resin composition layer can be formed by not using a photomask at the time of exposure and/or not developing. The colored pattern and colored coating film formed in this way are the color filter of this invention.

The film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose or use, for example, 0.1 µm or more and 30 µm or less, preferably 0.1 µm or more and 20 µm or less, more preferably is 0.5 µm or more and 6 µm or less.

As the substrate, a glass plate, a resin plate, silicon, or a substrate in which an aluminum, silver, silver/copper/palladium alloy thin film or the like is formed is used. On such a board|substrate, another color filter layer, a resin layer, a transistor, a circuit, etc. may be formed.

Formation of each color pixel by the photolithographic method can be performed with a well-known or customary apparatus and conditions. For example, it can be produced as follows.

First, a colored curable resin composition is apply|coated on a board|substrate, volatile components, such as a solvent, are removed and dried by heat-drying (pre-baking) and/or drying under reduced pressure, and a smooth colored curable resin composition layer is obtained.

As a coating method, the spin coat method, the slit coat method, the slit-and-spin coat method, etc. are mentioned.

30 degreeC or more and 120 degrees C or less are preferable and, as for the temperature in the case of heat-drying, 50 degrees C or more and 110 degrees C or less are more preferable. Moreover, as heating time, it is preferable that they are 10 second or more and 60 minutes or less, and it is more preferable that they are 30 second or more and 30 minutes or less.

When performing reduced-pressure drying, it is preferable to carry out in the temperature range of 20 degreeC or more and 25 degrees C or less under a pressure of 50 Pa or more and 150 Pa or less.

The film thickness of colored curable resin composition is not specifically limited, What is necessary is just to select suitably according to the film thickness of the color filter made into the objective.

Next, the colored curable resin composition layer is exposed through a photomask for forming the target colored pattern. It is preferable to use an exposure apparatus such as a mask aligner and a stepper to uniformly irradiate the entire exposure surface with parallel rays and to accurately align the photomask and the substrate on which the colored curable resin composition layer is formed. .

As a light source used for exposure, you may use the light source which generate|occur|produces the light of the wavelength of 250 nm or more and 450 nm or less. For example, light of less than 350 nm is cut using a filter that cuts this wavelength region, or light around 436 nm, 408 nm, or 365 nm is selectively extracted using a bandpass filter that extracts these wavelength regions. You can do it. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned.

A colored pattern is formed on a board|substrate by making a developing solution contact and developing the colored curable resin composition layer after exposure. By image development, the unexposed part of a colored curable resin composition layer melt|dissolves in a developing solution and is removed.

As a developing solution, the aqueous solution of alkaline compounds, such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, and tetramethylammonium hydroxide, is preferable, for example. The concentration in the aqueous solution of such an alkaline compound may be, for example, 0.01 mass% or more and 10 mass% or less. Moreover, the developing solution may contain surfactant.

Any of a paddle method, a dipping method, a spray method, etc. may be sufficient as the image development method. In addition, you may incline a board|substrate at an arbitrary angle at the time of image development.

It is preferable that the board|substrate after image development is washed with water.

Moreover, it is preferable to post-baking to the obtained coloring pattern.

(4) display device

The color filter is useful as a color filter used for a display device (eg, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image pickup device, and particularly as a color filter used for a liquid crystal display device.

(Example)

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples, of course, and may be carried out with appropriate changes within a range suitable for the purpose of the above and later. possible, and they are all included in the technical scope of the present invention. In addition, below, unless otherwise indicated, "part" means "part by mass" and "%" means "mass %".

In the following synthesis examples, the structure of the compound was confirmed by mass spectrometry (LC; Model 1200 manufactured by Agilent, MASS; Model LC/MSD6130 manufactured by Agilent).

The measurement of the polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) of resin was performed by GPC method on the following conditions.

Device: HLC-8120GPC (manufactured by Toso Co., Ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40℃

Solvent: tetrahydrofuran

Flow rate: 1.0mL/min

Solid content concentration of analysis sample: 0.001 to 0.01 mass %

Injection volume: 50μL

Detector: RI

Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Toso Co., Ltd.)

Ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) obtained above was made into the dispersion degree.

Synthesis Example 1

3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.0 parts, glycine (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.8 parts, zinc acetate (manufactured by Kanto Chemical Co., Ltd.) 1.3 parts and 314 parts of imidazole (made by Tokyo Chemical Industry Co., Ltd.) were added, and it stirred at 150 degreeC for 7 hours. While maintaining the obtained mixture at 20°C or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) prepared in advance and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was wash|cleaned with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 9.1 parts of a compound represented by formula (II-1) (also described as compound II-1) (yield: 88%).

[Formula 26]

<Identification of compound II-1>

(mass spectrometry) ionization mode=ESI-: m/z=[MH] ^- 505

Exact Mass: 506

Synthesis Example 2

3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.0 parts, 5-aminopentanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 6.0 parts zinc acetate (Kanto Chemical Co., Ltd.) ) agent) 1.3 parts and imidazole (Tokyo Chemical Industry Co., Ltd. product) 314 parts were added, and it stirred at 150 degreeC for 14 hours. While maintaining the obtained mixture at 20°C or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) prepared in advance and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was wash|cleaned with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 8.8 parts of a compound represented by formula (II-4) (also referred to as compound II-4) (yield 77%).

[Formula 27]

<Identification of compound II-4>

(mass spectrometry) ionization mode=ESI-: m/z=[MH] ^- 589

Exact Mass: 590

Synthesis Example 3

3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.0 parts, 4-amino-3,5-dimethylbenzoic acid (European Journal of Medicinal Chemistry 2014, in the method described in 78.236) 8.4 parts of zinc acetate (manufactured by Kanto Chemical Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 150°C for 22 hours. While maintaining the obtained mixture at 20°C or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) prepared in advance and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the residue after filtration was wash|cleaned with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 13 parts of a compound represented by formula (II-8) (also described as compound II-8) (yield: 90%).

[Formula 28]

<Identification of compound II-8>

(mass spectrometry) ionization mode=ESI-: m/z=[MH] ^- 685

Exact Mass: 686

Synthesis Example 4

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride (ComBi Blocks 2.9 parts of the compound represented by Formula (II-91) (it is also described as compound II-91) was obtained in the same manner as in Synthesis Example 1 except that it was replaced with 3.4 parts (yield 70%).

[Formula 29]

<Identification of compound II-91>

(mass spectrometry) ionization mode=ESI-: m/z=[MH] ^- 641

Exact Mass: 642

Synthesis Example 5

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride (ComBi Blocks 3.7 parts of the compound (also described as compound II-94) represented by Formula (II-94) was obtained in the same manner as in Synthesis Example 2 except that it was replaced with 3.4 parts (yield: 79%).

[Formula 30]

<Identification of compound II-94>

(mass spectrometry) ionization mode=ESI-: m/z=[MH] ^- 725

Exact Mass: 726

Synthesis Example 6

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 3.5 parts of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Aldrich) Except having changed, it carried out similarly to Synthesis Example 1, and obtained 2.7 parts of a compound (it is also described as compound II-100) represented by Formula (II-100) (yield 65%).

[Formula 31]

<Identification of compound II-100>

(mass spectrometry) ionization mode=ESI-: m/z=[MH] ^- 661

Exact Mass: 662

Synthesis Example 7

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was poured and replaced with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was put, and it heated to 80 degreeC, stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylic A mixed solution of 289 parts of a mixture (content ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution obtained by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at 80°C for 4 hours, cooled to room temperature, and a copolymer (resin B1) solution having a solid content of 35.1% and a viscosity measured with a B-type viscometer (23°C) of 125 mPa·s was obtained. The weight average molecular weight (Mw) of the produced|generated copolymer was 9.2x10<^3> , the dispersion degree 2.08, and the acid value in conversion of solid content was 77 mg-KOH/g. Resin B1 has the following structural units.

[Formula 32]

<Example 1>

(1) Preparation of coloring composition

Each component was mixed in the following ratios, and the colorant was dispersed using a bead mill. Then, the bead mill was removed by filtration, and the coloring composition 1 was obtained.

Colorant: Compound I 50 copies;

compound II-1 50 copies;

Dispersing agent: BYK-LPN6919 (Big Chemie Japan Co., Ltd.: 60% solids) 167 copies;

Resin (B): Resin B1 solution 229 copies;

Solvent (E): propylene glycol monomethyl ether acetate 3105 parts;

diacetone alcohol 400 copies

Next, each component was mixed in the following ratios, and the colored curable resin composition 1 was obtained.

Coloring composition 1 400 copies;

Resin (B): Resin B1 solution 45 copies;

Polymeric compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 25 copies;

Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) 15 copies;

Solvent (E): propylene glycol monomethyl ether acetate 86 copies;

Leveling agent: polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.) 0.12 parts

(2) Preparation of colored coating film

On a 5 cm wide glass substrate (Eagle XG; manufactured by Corning), the colored curable resin composition is applied by spin coating so that the post-baking film thickness is 1.7 to 2 μm, and then pre-baked at 100° C. for 3 minutes. , the colored curable resin composition layer was formed. After standing to cool, the colored curable resin composition layer formed on the substrate was irradiated with light at an exposure dose (365 nm standard) of ^{80 mJ/cm 2 in} an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). After light irradiation, in oven, it post-baked at 230 degreeC for 30 minute(s), and obtained the colored coating film.

(3) Heat resistance test

The absorbance of the obtained colored coating film was computed using the colorimeter (OSP-SP-200; OLYMPUS company make). After heating the colored coating film after a measurement at 230 degreeC in air atmosphere in oven for 120 minutes, the absorbance was computed using the colorimeter. The absorbance retention was calculated|required from the absorbance change of the maximum absorption wavelength of the colored curable composition film|membrane before and behind a heat resistance test.

<Example 2>

The colored curable resin composition 2 was obtained like Example 1 except having changed into the compound (II-4) instead of the compound (II-1). A result is shown in Table 4.

<Example 3>

The colored curable resin composition 3 was obtained like Example 1 except having changed into the compound (II-8) instead of the compound (II-1). A result is shown in Table 4.

<Example 4>

The colored curable resin composition 4 was obtained like Example 1 except having changed the compound (I) into 40 parts and the compound (II-8) into 60 parts. A result is shown in Table 4.

<Example 5>

Except having changed the compound (I) into 60 parts and the compound (II-8) into 40 parts, it carried out similarly to Example 1, and the colored curable resin composition 5 was obtained. A result is shown in Table 4.

<Example 6>

The colored curable resin composition 6 was obtained like Example 1 except having changed into the compound (II-91) instead of the compound (II-1). A result is shown in Table 4.

<Example 7>

The colored curable resin composition 7 was obtained like Example 1 except having changed into the compound (II-94) instead of the compound (II-1). A result is shown in Table 4.

<Example 8>

Except having changed into compound (II-100) instead of compound (II-1), it carried out similarly to Example 1, and obtained the colored curable resin composition 8. A result is shown in Table 4.

<Comparative Example 1>

Except having prepared the coloring agent without using compound (II-1), it carried out similarly to Example 1, and obtained colored curable resin composition 9. A result is shown in Table 4.

[Table 4]

Claims (7)

A coloring composition comprising a coloring agent and a resin, wherein the coloring agent contains a compound represented by the following formula (I) and a compound represented by the following formula (II).
[Formula 1]

[Formula 2]

[In formula (II),
R ¹ and R ² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms.
R ³ to ^{R 10} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.] The method of claim 1,
Said R<^1> and R<^2> are a C1-C20 divalent aromatic hydrocarbon group, The coloring composition. The method of claim 1,
Said R<^1> and R<^2> are each independently a C1-C20 alkanediyl group, The coloring composition. The method of claim 1,
Said R<^1> and R<^2> are each independently a C1-C20 divalent alicyclic hydrocarbon group, The coloring composition. The colored curable resin composition containing the compound represented by following formula (I), the compound represented by following formula (II), resin, a polymeric compound, a polymerization initiator, and a solvent.
[Formula 3]

[Formula 4]

[In formula (II),
R ¹ and R ² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms.
R ³ to ^{R 10} each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.] The color filter formed from the colored curable resin composition of Claim 5. A display device comprising the color filter of claim 6 .