JP2020079396A - Coloring composition - Google Patents

Abstract

To provide a coloring composition excellent in heat resistance.SOLUTION: A coloring composition includes a colorant and a resin, where the colorant includes a compound represented by formula (I) in the figure and a compound represented by formula (II) in the figure.SELECTED DRAWING: None

Description

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

  In the field of agricultural films, a fluorescent film having a resin layer containing a trade name of Lumogen (registered trademark) F Orange 240 as a perylene compound is known (Patent Document 1).

JP-A-10-235776

  In the field of colorants, improvement in heat resistance is required.

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

［式（ＩＩ）中、
Ｒ^１及びＲ^２は、それぞれ独立して、炭素数１〜２０の２価の炭化水素基を表す。
Ｒ^３〜Ｒ^１０は、それぞれ独立して、水素原子、ニトロ基、ハロゲン原子、又は置換基を有していてもよい炭素数１〜４０の炭化水素基を表す。］
［２］ 前記Ｒ^１及びＲ^２は、炭素数１〜２０の２価の芳香族炭化水素基である、［１］に記載の着色組成物。
［３］ 前記Ｒ^１及びＲ^２は、それぞれ独立して、炭素数１〜２０のアルカンジイル基である、［１］に記載の着色組成物。
［４］ 前記Ｒ^１及びＲ^２は、それぞれ独立して、炭素数１〜２０の２価の脂環式炭化水素基である、［１］に記載の着色組成物。
［５］ 下記式（Ｉ）で表される化合物と、下記式（ＩＩ）で表される化合物と、樹脂と、重合性化合物と、重合開始剤と、溶剤とを含む着色硬化性樹脂組成物。

［式（ＩＩ）中、
Ｒ^１及びＲ^２は、それぞれ独立して、炭素数１〜２０の２価の炭化水素基を表す。
Ｒ^３〜Ｒ^１０は、それぞれ独立して、水素原子、ニトロ基、ハロゲン原子、又は置換基を有していてもよい炭素数１〜４０の炭化水素基を表す。］
［６］ ［５］に記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［７］ ［６］に記載のカラーフィルタを含む表示装置。 The present invention provides the following colored composition, colored curable resin composition, color filter and display device.
[1] A coloring composition containing a colorant and a resin, wherein the colorant contains a compound represented by the following formula (I) and a compound represented by the following formula (II). Composition.

[In the 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 divalent aromatic hydrocarbon groups 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 containing 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. .

[In the 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 from the colored curable resin composition according to [5].
[7] A display device including the color filter according to [6].

  According to the present invention, a colored composition having excellent heat resistance can be provided.

(1) Colored composition The colored composition of the present invention contains a colorant (hereinafter, also referred to as a colorant (A)) and a resin (hereinafter, also referred to as a 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 the colorant (A1)).
The colorant (A) may contain one kind or two or more kinds of colorants (A1).
The colored composition of the present invention may contain a solvent (hereinafter, also referred to as a solvent (E)).
The compound (I) and the compound (II) may be dispersed in the solvent (E).

<Compound (I)>
As the compound (I), a commercially available compound can be used. As an example of a typical commercially available product of compound (I), Lumogen (registered trademark) F Orange 240 (manufactured by BASF) can be mentioned.

  Compound (I) can be produced by a well-known general production method, for example, by reacting 3,4,9,10-perylenetetracarboxylic acid 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. Of these, a divalent saturated chain aliphatic hydrocarbon group (hereinafter, also referred to as alkanediyl group) is preferable. The alkanediyl group may be linear or branched.

The linear alkanediyl group represented by R ¹ and R ² includes a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group. , 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-diyl group, Examples thereof include a heptadecane-1,17-diyl group, an octadecane-1,18-diyl group, a nonadecane-1,19-diyl group, and an icosane-1,20-diyl group. Among them, an alkanediyl group having 1 to 10 carbon atoms is preferable, an alkanediyl group having 1 to 4 carbon atoms is more preferable, and a methylene group, an ethylene group, a propane-1,3-diyl group, and butane-1,4- are more preferable. A diyl group and a pentane-1,5-diyl group.

Examples of the branched alkanediyl group represented by R ¹ and R ² include 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 Group, 2-methylpentane-1,5-diyl group, 3-methylpentane-1,5-diyl group, 2,3-dimethylpentane-1,4-diyl group, and the like. Among them, a branched alkanediyl group having 4 to 10 carbon atoms is preferable, a branched alkanediyl group having 4 to 6 carbon atoms is more preferable, and

Examples of the divalent unsaturated chain aliphatic hydrocarbon group represented by R ¹ and R ² include ethene-1,2-diyl group, prop-1-ene-1,3-diyl group, buta-2. Examples thereof include -ene-1,4-diyl group and penta-3-ene-1,4-diyl group.

The divalent alicyclic hydrocarbon group represented by R ¹ and R ² may be saturated or unsaturated. Of these, a divalent saturated alicyclic hydrocarbon group (hereinafter, also referred to as cycloalkanediyl group) is preferable. The cycloalkanediyl group may be monocyclic or polycyclic. Examples of the monocyclic cycloalkanediyl group include cyclopropane-1,2-diyl group, cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclo Examples thereof include cycloalkanediyl groups such as octane-1,5-diyl group. 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. . Of these, 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 cyclohex-2-ene-1,4-diyl group.

The divalent aromatic hydrocarbon group represented by R ¹ and R ² (hereinafter, also referred to as arenediyl group) may be monocyclic or polycyclic.
Examples of the monocyclic arenediyl group include a benzenediyl group, an alkylbenzenediyl group, and a dialkylbenzenediyl group. Specific examples thereof 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- Diyl group, 3-ethylbenzene-1,4-diyl group, 3,5-dimethylbenzene-1,4-diyl group, 3,5-diethylbenzene-1,4-diyl group, 3-methyl-5-ethylbenzene-1 , 4-diyl group, and 2-methyl-6-ethylbenzene-1,4-diyl group.

Examples of the polycyclic arenediyl group include naphthalene-1,5-diyl group, naphthalene-1,6-diyl group, naphthalene-1,7-diyl group, naphthalene-1,8-diyl group and the like. Further, the divalent aromatic hydrocarbon group represented by R ¹ and R ² may be one in which two or more aromatic hydrocarbon groups are linked, and [1,1′-biphenyl]-4,4 Examples include a'-diyl group and the like.

The arenediyl group represented by R ¹ and R ² is preferably a monocyclic arenediyl group, more preferably a benzene-1,4-diyl group, 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 selected from the group consisting of alkanediyl groups having 1 to 20 carbon atoms, cycloalkanediyl groups having 3 to 20 carbon atoms, and arenediyl groups having 6 to 20 carbon atoms. More preferably a group selected from the group consisting of alkanediyl groups having 1 to 10 carbon atoms, cycloalkanediyl groups having 3 to 10 carbon atoms, and arenediyl groups having 6 to 10 carbon atoms, and Preferably, it is a group selected from the group consisting of an alkanediyl group having 1 to 6 carbon atoms, a monocyclic cycloalkanediyl group having 5 to 7 carbon atoms, a benzenediyl group, an alkylbenzenediyl group, and a dialkylbenzenediyl group. , And even more preferably methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl, 4-methylpentane-1,2-diyl group, cyclohexane. It is a group selected from the group consisting of -1,4-diyl group, benzene-1,4-diyl group and 3,5-dimethylbenzene-1,4-diyl group.

R ¹ and R ² may be each independently a group in which two or more of the above hydrocarbon groups are combined, for example, a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined, or an aromatic hydrocarbon group. It may be a group in which a hydrogen group is combined with at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group. The total carbon number of these combined groups is 20 or less.

R ¹ and R ² may be the same or different and are preferably the same.

Specific examples of R ¹ and R ² include groups represented by the following formula. * And ** represent a bond.

Preferred as R ¹ and R ² are each independently formulas (A-1) to (A-8), (A-14), (B-1) to (B-3) and (B-16). ) To (B-19) or a group represented by (C-3). From the viewpoint of production, the above groups are preferred.

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. Of these, 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, Decyl group, undecyl group, 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, heptatriacontyl group, Linear alkyl groups such as octatriacontyl group, nonatriacontyl group, tetracontyl group, etc.; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group 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, Branched chain alkyl groups such as (2-ethyl)hexyl group and (3-ethyl)heptyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group An alkenyl group such as a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a (1-(2-propenyl))ethenyl group, a (1,2-dimethyl)propenyl group, a 2-pentenyl group; Etc. The saturated or unsaturated chain hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 15 carbon atoms, and particularly preferably 1 to 10 carbon atoms. Among them, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferable, and a methyl group or an ethyl group is particularly preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^{3 to} R ¹⁰ include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group. 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 Group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5 A cycloalkyl group such as a tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, a 4-cyclohexylcyclohexyl group; a cyclohexenyl group (for example, cyclohex-2-ene, cyclohex-3-ene), a cycloheptenyl group, Cycloalkenyl groups such as cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group and the like. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, further preferably 4 to 20 carbon atoms, and particularly preferably 4 to 15 carbon atoms, It is more preferably 5 to 15, and particularly preferably 5 to 10. Of these, 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 phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethyl group. Phenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group , 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-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecyl Aromatic hydrocarbon groups such as phenyl group and pyrenyl group; and the like. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and further preferably 6 to 15 carbon atoms.

The hydrocarbon group represented by R ^{3 to} R ¹⁰ is a group formed by combining two or more of the above-mentioned hydrocarbon groups, for example, an aromatic hydrocarbon group, a chain hydrocarbon group and an alicyclic hydrocarbon group. It may be a group in combination with at least one, and examples thereof include an aralkyl group such as a benzyl group, a phenethyl group, and a 1-methyl-1-phenylethyl group; an arylalkenyl group such as a phenylethenyl group (phenylvinyl group). An arylalkynyl group 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, a (dimethyl(phenyl)methyl)phenyl group and the like. To be

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

  The number of carbon atoms of the group formed by combining two or more of the above hydrocarbon groups is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 15, and further preferably 6 to 15.

Examples of the substituent which the hydrocarbon group having 1 to 40 carbon atoms represented by R ^{3 to} R ¹⁰ may have include, for example, a halogen atom, a formyl group, a carboxy group, a formyloxy group, a hydroxy group, and a thiol. group, a sulfo group, a sulfamoyl group, pentafluorosulfanyl group, a carbamoyl group, an amino group, a nitro group, a 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 or the like Can be mentioned.

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Of these, 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 alkyl group represented by R ¹² and R ¹³ preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 5 carbon atoms.

  As the alkyl group having 1 to 20 carbon atoms, 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, Examples thereof include a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group and an icosyl group.

-COR ¹² includes an acetyl group, a propanoyl group, a butanoyl group, a 2,2-dimethylpropanoyl group, a pentanoyl group, a hexanoyl group, a (2-ethyl)hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, Examples thereof include an undecanoyl group, a dodecanoyl group, a henicosanoyl group and a benzoyl group.

-COOR ¹² includes methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxy group. Examples thereof include a carbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group and an icosyloxycarbonyl group.

-OCOR ¹² includes an acetoxy group, a propanoyloxy group, a butanoyloxy group, a 2,2-dimethylpropanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a (2-ethyl)hexanoyloxy group, and a hepta. Noyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, 2-propenylcarbonyloxy group Groups and the like.

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, an octyl group. Examples thereof include sulfanyl group, nonylsulfanyl group, decylsulfanyl group, undecylsulfanyl group, dodecylsulfanyl group, icosylsulfanyl group, phenylsulfanyl group and o-tolylsulfanyl group.

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, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, phenylsulfonyl group, naphthylsulfonyl group, and the like.

The -SO ₂ NHR ^12, N- methylsulfamoyl group, N- ethylsulfamoyl group, N- propyl sulfamoyl group, N- isopropyl sulfamoyl 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 Moyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N- Examples thereof include an undecylsulfamoyl group, an N-dodecylsulfamoyl group, an N-icosylsulfamoyl group and an N-phenylsulfamoyl group.

The _{^{-SO 2 NR 12 R 13, N}} , N- dimethylsulfamoyl group, N, N-ethyl-methylsulfamoyl group, N, N-diethyl sulfamoyl group, N, N-propyl-methylsulfamoyl Group, N,N-dipropylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N- Diisobutylsulfamoyl group, N,N-disec-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group Moyl group, N,N-dipentylsulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfa Moyl group, N,N-diheptylsulfamoyl group, N,N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decyl Methylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group Group, N,N-diphenylsulfamoyl group and the like.

-CONHR ¹² includes 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- Examples thereof include an octylcarbamoyl group, an N-nonylcarbamoyl group, an N-decylcarbamoyl group, an N-undecylcarbamoyl group, an N-dodecylcarbamoyl group, an N-icosylcarbamoyl group and an N-phenylcarbamoyl group.

—CONR ¹² R ¹³ is an 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-butyloctylcarbamoyl 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-decylmethylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group Group, N,N-phenylmethylcarbamoyl group, N,N-diphenylcarbamoyl group and the like.

-NHR ¹² includes an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-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- A decylamino group, N-undecylamino group, N-dodecylamino group, N-icosylamino group, N-phenylamino group and the like can be mentioned.

-NR ¹² R ¹³ includes an 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-undecylmethylamino group, N,N-dodecylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group and the like. Be done.

-NHCOR ¹² includes an acetylamino group, a propanoylamino group, a butanoylamino group, a 2,2-dimethylpropanoylamino group, a pentanoylamino group, a hexanoylamino group, a (2-ethyl)hexanoylamino group, Examples thereof include a heptanoylamino group, an octanoylamino group, a nonanoylamino group, a decanoylamino group, an undecanoylamino group, a dodecanoylamino group, a henicosanoylamino group, and a benzoylamino group.

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

—CH ₂ — which is contained in the hydrocarbon group having 1 to 40 carbon atoms and is not represented by R ^{3 to} R ^{10 and} which does not form a ring is —O—, —CO—, —S(O) ₂ —, —. It may be replaced by NR ^x1 −. However, -CH ₂ - is never -COOH and -S _(O) 2 OH is formed by replacing. 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 and isopentyl group.

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

Preferred as R ^{3 to} R ¹⁰ are a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, —CH ₃ , and formulas (D-1) to (D-18) and (E-1) to (E). -27), (F-1) to (F-18) and (G-1) to (G-27). The halogen atom is preferably a chlorine atom and a bromine atom. When these atoms are included as halogen atoms, the colored pattern or the colored coating film formed from the colored curable resin composition tends to show excellent heat resistance or have a high transmittance at a wavelength of 630 nm. From the viewpoint of production, R ^{3 to} R ¹⁰ are preferably hydrogen atoms.

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

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

［式（ＩＩａ）中、
Ｒ^１ａ及びＲ^２ａは、それぞれ独立して、炭素数１〜２０のアルカンジイル基を表す。
Ｒ^３ａ〜Ｒ^１０ａは、それぞれ独立して、水素原子、ニトロ基、ハロゲン原子、又は置換基を有していてもよい炭素数１〜４０の炭化水素基を表す。］ A preferred embodiment of the compound (II) in the present invention includes a compound represented by the following formula (IIa) (hereinafter, also referred to as compound (IIa)).

[In the 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 the examples of the alkanediyl group in the description of R ¹ and R ² in the chemical formula (II).

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

  Specific examples of the compound (IIa) include compounds (II-1) to (II-6), (II-10) to (II-15) and (II-19) to (II) shown in Tables 1 to 3. -24), (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).

［式（ＩＩｂ）中、
Ｒ^１ｂ及びＲ^２ｂは、それぞれ独立して、炭素数１〜２０の２価の脂環式炭化水素基を表す。
Ｒ^３ｂ〜Ｒ^１０ｂは、それぞれ独立して、水素原子、ニトロ基、ハロゲン原子、又は置換基を有していてもよい炭素数１〜４０の炭化水素基を表す。］ Another preferred embodiment of the compound (II) in the present invention is a compound represented by the following formula (IIb) (hereinafter, also referred to as compound (IIb)).

[In the 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 those having 1 to 20 carbon atoms in the description of R ¹ and R ² in the above chemical formula (II). This is the same as the example of the divalent alicyclic hydrocarbon group.

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

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

［式（ＩＩｃ）中、
Ｒ^１ｃ及びＲ^２ｃは、それぞれ独立して、炭素数１〜２０の２価の芳香族炭化水素基を表す。
Ｒ^３ｃ〜Ｒ^１０ｃは、それぞれ独立して、水素原子、ニトロ基、ハロゲン原子、又は置換基を有していてもよい炭素数１〜４０の炭化水素基を表す。］ 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)) can be mentioned.

[In the 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 2 to 1 carbon atoms in the description of R ¹ and R ² in the above chemical formula (II). It is the same as the example of the valent aromatic hydrocarbon group.

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

  Specific examples of the compound (IIc) include compounds (II-7), (II-8), (II-16), (II-17), (II-25) and (II) shown in Tables 1 to 3. -26), (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.

［式中、Ｒ^３〜Ｒ^１０は、上述の定義と同一である。］

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

［式中、Ｒは、炭素数１〜２０の２価の炭化水素基を表す。］

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

  Examples of the compound represented by the formula (pt1) include 3,4,9,10-perylenetetracarboxylic dianhydride.

Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms represented by R in the formula (ca1) include divalent hydrocarbon groups having 1 to 20 carbon atoms in the description of R ¹ and R ² in the above compound (II). It is the same as the example of the 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, 2-amino-3. -Methylpentanoic acid, 4-aminobenzoic acid, 2-amino-3-phenylpropionic acid.

  The amount of the compound represented by the formula (ca1) to be used is generally 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, relative to 1 mol of the compound represented by the formula (pt1). , More preferably 1 mol or more and 6 mol or less, and further preferably 1 mol or more and 4 mol or less.

  Examples of the solvent include water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, Alcohol solvent such as 1-octanol and phenol; Ether solvent such as diethyl ether and tetrahydrofuran; Ketone solvent such as acetone and methyl isobutyl ketone; Ester solvent such as ethyl acetate; Aliphatic hydrocarbon solvent such as hexane; Aromatic such as toluene Hydrocarbon solvents; 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.

  The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (pt1).

  The reaction temperature is usually −100° C. or higher and 300° C. or lower, preferably −90° C. or higher and 200° C. or lower, and more preferably −10° C. or higher and 150° C. or lower.

The method of taking out the compound (II) after completion of the reaction is not particularly limited, and it can be taken out by various known methods. For example, the compound (II) can be taken out by distilling off the solvent. Furthermore, after distilling off the solvent, the obtained residue may be purified by column chromatography, recrystallization or the like. Further, after the reaction is completed, the compound (II) can be taken out by filtration. After filtration, the obtained residue may be purified by column chromatography, recrystallization or the like. The chemical structure of the obtained compound (II) can be analyzed by a known analysis method and its conditions. Such an analysis method is not particularly limited, and examples thereof include an X-ray crystal structure analysis method, a mass spectrometry method (LC), an NMR analysis method and an elemental analysis method. The X-ray crystal structure analysis method is described in, for example, Chemistry of Materials, 2012, Vol. 24, p. It can be performed according to 4647-4652.

［式中、Ｒ^ａは、炭素数１〜２０のアルカンジイル基を表す。］ Compound (IIa) is 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. You can

[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 ^Ra 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 chemical 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, 8-amino. Octanoic 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-aminoeicoic acid, 2-aminopropionic acid, 2-amino-3-methylbutanoic acid, 2-amino-4-methylpentanoic acid, 2-amino-3-methylpentanoic acid and the like can be mentioned.

［式中、Ｒ^ｂは、炭素数１〜２０の２価の脂環式炭化水素基を表す。］ Compound (IIb) is 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. You can

[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 a divalent alicyclic ring having 1 to 20 carbon atoms in the description of R ¹ and R ² in the chemical formula (II). It is the same as the example of the formula hydrocarbon group.

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

［式中、Ｒ^ｃは、炭素数１〜２０の２価の芳香族炭化水素基を表す。］ 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.

[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 include divalent aromatic hydrocarbon groups having 1 to 20 carbon atoms in the description of R ¹ and R ² in the chemical formula (II). It is the same as the example of the hydrogen group.

  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% by mass or more, preferably 0.5% by mass or more, based on the total amount of the colorant (A). It is more preferably 1% by mass or more, further preferably 5% by mass or more, particularly preferably 10% by mass or more, further preferably 20% by mass or more, still more preferably 50% by mass or more. On the other hand, the content of the compound (I) in the colorant (A) is usually less than 100% by mass, for example, 99% by mass or less, based on the total amount of the colorant (A).

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

  The mass ratio of the compound (I) to the compound (II) in the colorant (A) may be, for example, 1:99 to 99:1, preferably 20:80 to 80:20, more preferably 30:. 70 to 70:30, more preferably 40:60 to 60:40. When the mass ratio of the compound (I) and the compound (II) in the colorant (A) is within the above range, the dispersibility of the compound (I) in the coloring composition is improved, and the heat resistance is easily improved. Tends to become.

The content of the colorant (A) in the coloring composition may be, for example, 0.1% by mass or more and 99.9% by mass or less, and preferably 0.1% by mass or less, based on the total amount of solids in the coloring composition. 5 mass% or more and 99 mass% or less, more preferably 1 mass% or more and 90 mass% or less, further preferably 5 mass% or more and 80 mass% or less, and particularly preferably 10 mass% or more and 70 mass% or less. Is more preferably 15% by mass or more and 60% by mass 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 very preferably 30% by mass or more. It is from 40% by mass to 40% by mass.
In the present specification, the "total amount of solids in the coloring composition" refers to the total amount of components excluding all solvent components from the coloring composition. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis means such as liquid chromatography or gas chromatography.

<Colorant (A1)>
The colorant (A1) may be a dye or a pigment. As the dye, known dyes can be used, and examples thereof include known dyes described in Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Shikisosha). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes. Examples thereof include dyes, nitro dyes, phthalocyanine dyes and perylene dyes. You may use these dyes individually or in combination of 2 or more types.

Specific examples include dyes having the following color index (CI) numbers.
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 and the like C.I. I. Solvent dye,
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, C. 104, 105, 106, 109, etc. I. Acid dyes,
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. C. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and the like. I. Direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C. such as Disperse Blue 1, 14, 56, 60 and the like. I. Disperse 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. C. such as Basic Green 1; I. Basic dye,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. C. such as Reactive Red 36; I. Reactive dye,
C. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Mordan tread 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. Modern 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. Modant 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. C. such as Modern Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53. I. Modant dye,
C. I. C. such as Bat Green 1 I. Vat dye etc.

  Further, Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF) and Lumogen (registered trademark) F Red 305 (manufactured by BASF) can be mentioned.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments by Color Index (published by The Society of Dyers and Colorists). These may be used alone or in combination of two or more.
Specifically, C.I. 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, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
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. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and the like violet color pigments;
C. I. Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments;
C. I. Pigment Brown 23, 25 and other brown color pigments;
C. I. Pigment Black 1, 7, 31, 32 and other black pigments.

  The colorant (A1) is, if necessary, a rosin treatment, a surface treatment using a derivative having an acidic group or a basic group introduced therein, a graft treatment with a polymer compound or the like on the surface of the colorant (A1), sulfuric acid. Atomization treatment by an atomization method or the like, a cleaning treatment by an organic solvent or water for removing impurities, a removal treatment of an ionic impurity by an ion exchange method, or the like may be performed. The particle size of the colorant (A1) is preferably substantially uniform.

  When the colorant (A) further contains the colorant (A1), the lower limit of the total content of the compound (I) and the compound (II) in the colorant (A) is the total amount of the colorant (A). On the other hand, it is generally 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, further preferably 25% by mass or more, and particularly preferably 50% by mass or more. On the other hand, the upper limit of the total content of the compound (I) and the compound (II) in the colorant (A) is usually 100% by mass or less based on the total amount of the colorant (A).

  When the colorant (A) further contains the colorant (A1), the content of the colorant (A) in the coloring composition is usually 0.1% by mass based on the total amount of solids in the coloring composition. Or more and 99% by mass or less, for example, 0.1% by mass or more and 90% by mass or less, preferably 0.5% by mass or more and 80% by mass or less, and more preferably 0.7% by mass or more and 70% by mass or less. % Or less, particularly preferably 1% by mass or more and 60% by mass or less.

  When the coloring composition contains the solvent (E), a coloring agent-containing liquid containing the coloring agent (A) and the solvent (E) is prepared in advance, and then the coloring composition is prepared using the coloring agent-containing liquid. You may. When the colorant (A) does not dissolve in the solvent (E), the colorant-containing liquid can be prepared by dispersing the colorant (A) in the solvent (E) and mixing them. The colorant-containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.

  The 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 based on the total amount of the colorant-containing liquid. % By mass or less, more preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 90% by mass or less, further preferably 1% by mass or more and 60% or less, still more preferably 3% by mass or more. It is from 50% by mass to 50% by mass, particularly preferably from 3% by mass to 30% by mass, and most preferably from 5% by mass to 30% by mass.

The content 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, in the total amount of solids in the colorant-containing liquid. Is more preferably 0.01% by mass or more and 99% by mass or less, further preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 99% by mass or less, and It is preferably 2% by mass or more and 99% by mass or less.
In the present specification, the "total amount of solids in the colorant-containing liquid" refers to the total amount of components excluding the solvent (E) from the colorant-containing liquid. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis means such as liquid chromatography or gas chromatography.

  The colorant (A) can be in a state in which the colorant (A) is uniformly dispersed in the colorant-containing liquid by subjecting the colorant (A) to a dispersant and performing a dispersion treatment. Each of the colorants (A) may be subjected to a dispersion treatment alone or a mixture of a plurality of types may be subjected to a dispersion treatment.

  Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based, and acrylic-based surfactants. You may use these dispersants individually or in combination of 2 or more types. As the dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Sols Perth (registered trademark) (manufactured by Zeneca Corporation), and EFKA (registered trademark) are trade names. (Manufactured by BASF Co., Ltd.), Azisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by Big Chemie), BYK (registered trademark) (manufactured by Big Chemie) Can be mentioned.

  When a dispersant 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 100 parts by mass, with respect to 100 parts by mass of the colorant (A). 5,000 parts by mass or less, more preferably 1,000 parts by mass or less, further preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, more preferably 200 parts by mass or less, still more preferably Is 5 parts by mass or more and 150 parts by mass or less, particularly preferably 5 parts by mass or more and 110 parts by mass or less. When the amount of the dispersant used is in the above range, a more uniformly dispersed colorant-containing liquid tends to be obtained.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, and at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as “monomer (a)”). It is more preferable that the polymer has a structural unit derived from (in some cases).
The resin (B) is 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 A copolymer having the structural unit of is preferable.
As the other structural unit, a monomer copolymerizable with the monomer (a) (however, different from the monomer (a) and the monomer (b). Hereinafter, “monomer (c)”. In some cases), a structural unit having an ethylenically unsaturated bond, and the like.

Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-, m-, p-vinylbenzoic 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-cyclohexene dicarboxylic 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, Bicyclo unsaturated compounds containing a carboxy group such as 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2-ene;
Carboxylic anhydrides such as anhydrides of the above unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl]esters of divalent or higher polyvalent carboxylic acids such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl]. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an aqueous alkaline solution.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), an oxetanyl group and an ethylenically unsaturated bond. (Hereinafter sometimes referred to as “monomer (b2)”) and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b3)”) ) And the like.

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

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.
As the monomer (b1-1), specifically, glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, α- Methyl vinyl benzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxy) Methyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4. Examples thereof include 5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene.
Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl. (Meth)acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel) , A compound represented by the formula (BI), a compound represented by the formula (BII), and the like.

[In the 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, and the hydrogen atom contained in the alkyl group is a hydroxy group. May be replaced with.
X ^a and ^{X b} are each independently a single ^{bond, * - R c -, *} - R c -O -, * - represents the R c -S- or ^* -R c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

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

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

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

  Examples of the alkanediyl group include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, Hexane-1,6-diyl group and the like can be mentioned.

The X ^a and ^{X b,} preferably a single bond, a methylene group, an ethylene group, * _- CH 2 -O- and _* -CH ₂ CH ₂ -O- and the like, more preferably a single bond, * - CH ₂ CH ₂ -O- and the like (* represents a bond to O.).

  Examples of the compound represented by the formula (BI) include compounds represented by any of the 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). The compound represented by formula (BI-1), the formula (BI-7), the formula (BI-9) and the compound represented by the formula (BI-15) are more preferable.

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

  The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination with the compound represented by the formula (BI) and the compound represented by the formula (BII). You may. When these are used in combination, 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: It is 90 to 90:10, and more preferably 20:80 to 80:20.

As the monomer (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3. -Acryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, etc. Is mentioned.

As the monomer (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

  The monomer (b) is preferably the monomer (b1) from the viewpoint that the obtained color filter can have higher reliability such as heat resistance and chemical resistance. Furthermore, the monomer (b1-2) is more preferable in that the storage stability of the coloring composition is excellent.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 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, dicyclopentanyloxyethyl(meth)acrylate, isobornyl(meth) ) (Meth)acrylic acid esters such as acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and benzyl (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid ester 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- Hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]. Hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2] .1] hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2. 1] hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-Methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2 2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyl) Oxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclo unsaturated compounds;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate and N-(9-acridinyl)maleimide;
Vinyl group-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth)acrylamide And vinyl group-containing amides such as vinyl acetate; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene;
Among these, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl(meth)acrylate, tricyclo[5.2.1] from the viewpoint of copolymerization reactivity and heat resistance. .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, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and benzyl(meth)acrylate 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 group having the monomer (a) or the monomer (b) in the polymer having the structural unit derived from the monomer (a) or the monomer (b). It can be obtained by adding a monomer having an ethylenically unsaturated bond to a group capable of reacting with.
Examples of such a structural unit include a structural unit in which glycidyl (meth)acrylate is added to a (meth)acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth)acrylate is added to a maleic anhydride unit, and glycidyl (meth). ) A structural unit in which (meth)acrylic acid is added to an acrylate unit can be used. Moreover, when these structural units have a hydroxy group, the structural unit to which the carboxylic acid anhydride was further added 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 polymerizing the monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, the solvent and the like are not particularly limited, and those usually used in the art can be used. For example, as the polymerization initiator, an azo compound (2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile) or the like) or an organic peroxide (benzoyl peroxide or the like) The solvent may be any solvent that can dissolve each monomer.

The obtained polymer may be used as it is after the reaction, or may be used as a concentrated or diluted solution, or as a solid (powder) obtained by a method such as reprecipitation. May be used.
If necessary, a reaction catalyst (for example, tris(dimethylaminomethyl)phenol or the like) between a carboxylic acid or a carboxylic acid anhydride and a cyclic ether, a polymerization inhibitor (for example, hydroquinone), or the like may be used.
As the carboxylic acid anhydride, maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic acid anhydride, 4-vinylphthalic acid anhydride, 3,4,5,6-tetrahydrophthalic acid anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and the like.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Decyl (meth)acrylate/(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-cyclohexyl maleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5 2.2.1.0 ^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)acrylate 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 Copolymers, benzyl (meth)acrylate/(meth)acrylic acid copolymers, styrene/(meth)acrylic acid copolymers and JP-A-9-106071, JP-A 2004-29518 and JP-A 2004-2004. Resins and the like described in the respective publications of 361455 can be mentioned.
Among them, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).

The resin (B) may be a combination of two or more kinds. In this case, the 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-epoxy It is preferable to include one or more selected from tricyclo[5.2.1.0 ^2,6 ]decyl (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, and further preferably 1,000 or more. It is 30,000 or less, and particularly preferably 3,000 or more and 30,000 or less.

  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, and further preferably 1. It is 01 or more and 4 or less.

  The acid value (solid content conversion value) 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, further 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, more preferably 30 mg-KOH/g or more and 170 mg-KOH/g or less, particularly preferably 60 mg-KOH. /G or more and 150 mg-KOH/g or less, and very preferably 65 mg-KOH/g or more and 135 mg-KOH/g or less. Here, the acid value is a value measured as an amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by, for example, titration using an aqueous potassium hydroxide solution.

  The content of the resin (B) in the coloring composition may be, for example, 0.1% by mass or more and 99.9% by mass or less, and preferably 0.5% by mass, based on the total amount of solids in the coloring composition. Mass% or more and 99 mass% or less, more preferably 1 mass% or more and 95 mass% or less, further preferably 2 mass% or more and 90 mass% or less, particularly preferably 3 mass% or more and 80 mass% or less, and further preferably Is 5 mass% or more and 70 mass% or less, more preferably 7 mass% or more and 60 mass% or less, particularly preferably 10 mass% or more and 50 mass% or less, and very preferably 10 mass% or more and 30 mass% or less. % Or less.

  When a colorant-containing liquid is prepared in advance and then the colorant-containing liquid of the present invention is prepared using the colorant-containing liquid, the colorant-containing liquid is a resin (B) described later contained in the colorant composition. Part or all, preferably part may be included in advance. By preliminarily containing the resin (B), 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, and more preferably 1000 parts by mass with respect to 100 parts by mass of the coloring agent (A). The amount is not more than 1 part by mass, more preferably not less than 1 part by mass and not more than 500 parts by mass, particularly preferably not less than 5 parts by mass and not more than 200 parts by mass, more preferably not less than 10 parts by mass and not more than 100 parts by mass.

［式（ＩＩａ）中、Ｒ^１ａ〜Ｒ^１０ａの定義は上述の定義と同一である。］ <Embodiment 1>
The coloring composition according to Embodiment 1 is a coloring composition containing a coloring agent (A) and a resin (B), wherein the coloring agent (A) is a compound represented by the formula (I), and It is a coloring composition containing the compound represented by formula (IIa).

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

  Examples and preferable ranges of the respective content rates of the compound (I) and the compound (IIa) in the colorant (A) are the respective content rates of the compound (I) and the compound (II) in the colorant (A) described above. It is the same as the exemplified and preferred ranges.

［式（ＩＩｂ）中、Ｒ^１ｂ〜Ｒ^１０ｂの定義は上述の定義と同一である。］ <Embodiment 2>
A coloring composition according to Embodiment 2 is a coloring composition containing a colorant (A) and a resin (B), wherein the colorant (A) is a compound represented by the formula (I) and the following: It is a coloring composition containing the compound represented by Formula (IIb).

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

  Examples and preferable ranges of the respective content rates of the compound (I) and the compound (IIb) in the colorant (A) are the respective content rates of the compound (I) and the compound (II) in the colorant (A) described above. It is the same as the exemplified and preferred ranges.

［式（ＩＩｃ）中、Ｒ^１ｃ〜Ｒ^１０ｃの定義は上述の定義と同一である。］ <Embodiment 3>
The coloring composition according to Embodiment 3 is a coloring composition containing a colorant (A) and a resin (B), and the colorant (A) contains a compound (IIc).

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

  Examples and preferred ranges of the respective contents of the compound (I) and the compound (IIc) in the colorant (A) are the respective contents of the compound (I) and the compound (II) in the colorant (A) described above. It is the same as the exemplified and preferred ranges.

(2) Colored curable resin composition The colored curable resin composition includes a compound (I), a compound (II), a resin (B) (hereinafter collectively referred to as a colorant (A)), It contains a polymerizable compound (hereinafter sometimes referred to as the polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as the polymerization initiator (D)).
The colored curable resin composition comprises a leveling material (hereinafter sometimes referred to as leveling material (F)), an antioxidant (hereinafter sometimes referred to as antioxidant (G)), and a solvent (E). It may further include one selected from the group.

  The content of the solid content in the colored composition contained in the colored curable resin composition is appropriately adjusted according to the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured. Although not particularly limited, it may be, for example, 1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 90% by mass or less, and more preferably based on the total amount of solids in the colored curable resin composition. 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, and further preferably 5 mass% or more and 50 mass% or less. Or less, particularly preferably 6% by mass or more and 45% by mass or less, and very preferably 7% by mass or more and 40% by mass or less.

  Each content of the colorant (A) in the colored curable resin composition is particularly limited because it is appropriately adjusted according to the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured. However, the total amount of solids in the colored curable resin composition may be, for example, 0.1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 90% by mass or less, and more preferably 2% by mass or more. 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, and further preferably 5 mass% or more and 50 mass% or less. It is particularly preferably 8% by mass or more and 40% by mass or less, and most preferably 10% by mass or more and 30% by mass or less.

  In the present specification, the “total amount of solids in the colored curable resin composition” refers to the total amount of components excluding the solvent (E) from the colored curable resin composition. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis means such as liquid chromatography or gas chromatography. The content of solids in the colored curable resin composition may be, for example, 0.01% by mass or more and less than 100% by mass, and preferably 0.1% by mass, with respect to the total amount of the colored curable resin composition. Or more and 99.9 mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 60% or less, and further preferably 3 mass% or more and 50 mass% or less. It is more preferably 3% by mass or more and 30% by mass or less, and particularly preferably 5% by mass or more and 30% by mass or less.

  The coloring pattern or colored coating film described below formed from the colored curable resin composition of the present invention is not only excellent in heat resistance, but also tends to have high transmittance at a wavelength of 630 nm, and preferably the compound (I) alone is used. The transmittance at a wavelength of 630 nm tends to be higher than that of a colored pattern or a colored coating film formed from the colored curable resin composition containing. The colored pattern or colored coating film described below formed from the colored curable resin composition of the present invention may have a transmittance at a wavelength of 630 nm of, for example, 90% or more, preferably 95% or more, and more preferably 97. % Or more. 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 by an active radical and/or an acid generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenic unsaturated bond or the like, 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, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Etc., and the above-mentioned monomers (a), (b) and (c).

  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, triethylene glycol di. Examples thereof include (meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

  Among them, the polymerizable compound (C) is preferably a polymerizable compound having 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, dipentaerythritol 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, Examples thereof include caprolactone-modified pentaerythritol tetra(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

  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, and particularly preferably 150 or more and 2900 or less. And 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, based on the total amount of solids in the colored curable resin composition. Or less, more preferably 3% by mass or more and 80% by mass or less, further preferably 4% by mass or more and 70% by mass or less, particularly preferably 5% by mass or more and 60% by mass or less, and further preferably 6% by mass or less. It is from 50% by mass to 50% by mass, and particularly preferably from 7% by mass to 40% by mass.

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

  Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine oxide compounds.

  Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 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- Examples thereof include cyclopentylpropan-1-one-2-imine. As the O-acyl oxime compound, commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF Ltd.) and N-1919 (manufactured by ADEKA) may be used. Among them, as the O-acyl oxime compound, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- At least one selected from the group consisting of 1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferable, and N-benzoyl Oxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one and 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-. On and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one and the like. As the alkylphenone compound, commercially available products such as Irgacure 369, 907 and 379 (all manufactured by BASF Corporation) may be used.
Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, Mention may also be made of 1-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyldimethyl ketal.

  Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole and 2,2'-bis(2,3-dichlorophenyl)-4. , 4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4, 4',5,5'-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 (see, for example, JP-B-48-38403 and JP-A-62-174204). And a biimidazole compound in which the phenyl group at the 4,4′,5,5′-position is substituted with a carboalkoxy group (see, for example, JP-A-7-10913).

  Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl). -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis( Trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methyl) Phenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine. ..

  Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. A commercially available product such as Irgacure (registered trademark) 819 (manufactured by BASF Ltd.) may be used.

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3′,4,4′-tetra(tert-butylperoxycarbonyl)benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds and the like.
These are preferably used in combination with the below-mentioned polymerization initiation aid (D1) (particularly amines).

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

  The content of the polymerization initiator (D) is, for example, 0.01% by mass or more and 40% by 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. It may be the following, preferably 0.1% by mass or more and 35% by mass or less.

<Polymerization initiation aid (D1)>
The polymerization initiation aid (D1) is a compound or a sensitizer used for promoting the polymerization of the polymerizable compound whose polymerization is initiated by the polymerization initiator. When the polymerization initiator auxiliary agent (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.

  As the amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-Ethylhexyl dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4′-bis(dimethylamino)benzophenone (commonly called Michler's ketone), 4,4′-bis(diethylamino)benzophenone and 4,4′-bis( Examples thereof include ethylmethylamino)benzophenone, and preferably 4,4′-bis(diethylamino)benzophenone. Further, as the amine compound, a commercially available product such as EAB-F (produced by Hodogaya Chemical Co., Ltd.) may be used.

  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-dibutoxy. Examples thereof include anthracene and 2-ethyl-9,10-dibutoxyanthracene.

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

  As the carboxylic acid compound, phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.

  When these polymerization initiation aids (D1) are used, their content is, for example, 0.01% by mass or more and 40% by mass or less based on the total amount of the resin (B) and the polymerizable compound (C). Good, and preferably 0.1% by mass or more and 30% by mass or less.

<Solvent (E)>
The solvent (E) is, for example, an ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule, not containing -COO-), ether. Ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule, not containing -COO-), alcohol solvent (containing OH in the molecule, Solvents not containing —O—, —CO— and —COO—), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.

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

  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 Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole and methylanisole.

  Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, and 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

  Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. Etc.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.

  Two or more kinds of these solvents may be used in combination.

  The content of the solvent (E) is usually 99.99% by mass or less, preferably 0.1% by mass or more and 99.9% by mass or less, and more preferably based on the total amount of the colored curable resin composition. Is 1% by mass or more and 99.9% by mass or less, more preferably 10% by mass or more and 99% by mass or less, particularly preferably 40% by mass or more and 99% by mass or less, and further preferably 50% by mass or more and 90% by mass or more. It is preferably not more than 60% by mass, particularly preferably not less than 60% by mass and not more than 95% by mass, and most preferably not less than 70% by mass and not more than 90% by mass.

  The colored curable resin composition of the present invention is prepared by dispersing all or part of compound (I) and compound (II) in all or part of solvent (E) to prepare a colorant-containing liquid, It may be prepared using a colorant-containing liquid.

  The content of the 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% by mass or less, based on the total amount of the colorant-containing liquid. 1.9 mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 90 mass% or less, and more preferably 1 mass% or more and 60% or less. It is more preferably 3% by mass or more and 50% by mass or less, particularly preferably 3% by mass or more and 30% by mass or less, and very preferably 5% by mass or more and 30% by mass or less.

  The total content of the compound (I) and the compound (II) in the colorant-containing liquid may be, for example, 0.0001% by mass or more, and preferably 0.01% by mass, in the total amount of solids in the coloring dispersion liquid. % Or more, more preferably 1% by mass or more, further preferably 5% by mass or more, further preferably 10% by mass or more, still more preferably 20% by mass or more, particularly preferably 30% by mass. It is at least mass%. On the other hand, the upper limit of the total content of the compound (I) and the compound (II) in the colorant-containing liquid is usually less than 100% by mass in the total amount of solids in the colorant-containing liquid, for example 99% by mass or less. May be

  When a colorant-containing liquid is prepared by dispersing all or part of compound (I) and compound (II) in all or part of solvent (E), include all or part of resin (B). By preserving it, 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, and preferably 5000 parts by mass or less, based on 100 parts by mass of the total amount of the compound (I) and the compound (II). , More preferably 1000 parts by mass or less, further preferably 1 part 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 further preferably 10 parts by mass or more and 100 parts by mass or less. Is.

  The compound (I) and the compound (II) are, if necessary, rosin-treated, surface-treated with a derivative having an acidic group or a basic group introduced therein, a compound (I) and a compound (II) with a polymer compound or the like. ) Even if it has been subjected to surface grafting, atomization by sulfuric acid atomization, cleaning with organic solvent or water to remove impurities, removal of ionic impurities by ion exchange, etc. Good. The particle sizes of the compound (I) and the compound (II) are preferably substantially uniform.

  The compound (I) and the compound (II) can be made to be in a state of being uniformly dispersed in the colored dispersion liquid, by performing a dispersion treatment by containing a dispersant. .. Each of the compound (I) and the compound (II) may be subjected to dispersion treatment alone, or a plurality of kinds may be mixed and subjected to dispersion treatment. When the colorant (A) contains the compound (I), the compound (II) and the dispersant, the dispersibility of the compound (I) tends to be improved.

  Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based, and acrylic-based surfactants. You may use these dispersants individually or in combination of 2 or more types. As the dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Sols Perth (registered trademark) (manufactured by Zeneca Corporation), and EFKA (registered trademark) are trade names. (Manufactured by BASF Co., Ltd.), Azisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by Big Chemie Co., Ltd.), BYK (registered trademark) (manufactured by Big Chemie Co., Ltd.), etc. Can be mentioned.

  When a dispersant is used, the amount of the dispersant (solid content) used is 10000 parts by mass or less, preferably 5000 parts by mass or less, relative to 100 parts by mass of the compound (I) and the compound (II) in total. It is more preferably 1000 parts by mass or less, still 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. Parts by mass or less, particularly preferably 5 parts by mass or more and 50 parts by mass or less. When the amount of the dispersant used is within the above range, a colored dispersion liquid in a more uniform dispersed state tends to be obtained.

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

<Leveling agent (F)>
Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC). .

  Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florade (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F543. R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

  Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples include Megafac (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

  When the leveling agent (F) is contained, its content is usually 0.0005 mass% or more and 5 mass% or less, preferably 0.001 mass% or more 1 with respect to the total amount of the colored curable resin composition. Mass%, more preferably 0.001 mass% or more and 0.5 mass% or less, still more preferably 0.002 mass% or more and 0.2 mass% or less, and particularly preferably 0.005 mass% or more. It is 0.1 mass% or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Antioxidant (G)>
From the viewpoint of improving the heat resistance of the colorant, it is preferable to use the antioxidant (G) alone or in combination of two or more kinds. The antioxidant is not particularly limited as long as it is an industrially commonly used antioxidant, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant 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], manufactured by BASF Ltd.), Irganox 1076 (Irganox 1076: Octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF 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 Corp., 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 Ltd., Irganox 3790 (Irganox 3790:1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,3). 5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corp., Irganox 1035 (Irganox 1035: thiodiethylenebis[3-(3,5-di-tert-butyl- 4-hydroxyphenyl)propionate], manufactured by BASF Ltd., Irganox 1135 (Irganox 1135: benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 side chain alkyl) Ester, manufactured by BASF Corporation, Irganox 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Corporation), Irganox 3125 (Irganox 3125, manufactured by BASF Corporation). ), Irganox 565 (2,4-bis(n-octylthio)-6-(4-hydroxy3′,5′-di-tert-butylanilino)-1,3,5-triazine, BASF (strain). )), Adekastab AO-80 (Adekastab AO-80:3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethyl). Ethyl)-2,4,8,10-tetraoxaspiro( 5, 5) Undecane, manufactured by ADEKA Co., Ltd., Sumilizer BHT, manufactured by Sumitomo Chemical Co., Ltd., Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd., Sumilizer GS. , Sumitomo Chemical Co., Ltd., Cyanox 1790 (Cyanox 1790, Cytec Co., Ltd.), Vitamin E (Eisai Co., Ltd.), and the like.

  Examples of the phosphorus-based antioxidant include Irgafos 168 (Irgafos 168: Tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF Ltd.), Irgafos 12 (Irgafos 12: Tris[2- [[2,4,8,10-Tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl]oxy]ethyl]amine, manufactured by BASF Ltd., Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Ltd., ADEKA STAB 329K (manufactured by ADEKA), ADEKA STAB PEP36 (manufactured by ADEKA), ADEKA STAB PEP-8 (manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (Weston 618, manufactured by GE), Weston 619G (Weston 619G, GE). Company), Ultranox 626 (Ultranox 626, manufactured by GE) and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4. 8,10-Tetra-tert-butyldibenz[d,f][1.3.2]dioxaphosphepine) (Sumitomo Chemical Co., Ltd.) and the like can be mentioned.

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

<Other ingredients>
The colored curable resin composition of the present invention may optionally contain additives known in the art such as a filler, another polymer compound, an adhesion promoter, a light stabilizer and a chain transfer agent. .
Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycid. Xypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercapto Propyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-amino Propylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3 -Aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane and the like can be mentioned.

<Method for producing colored curable resin composition>
The colored curable resin composition includes, for example, a colorant (A), a resin (B), a solvent (E), a leveling agent (F), a polymerizable compound (C), and a polymerizable compound (C) when patterning by a photolithography method. It can be prepared by mixing with the polymerization initiator (D), the polymerization initiation aid (D1) and other components.
The pigment is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, part or all of the pigment dispersant and the resin (B) may be blended, if necessary. The target colored curable resin composition can be prepared by mixing the remaining components in the pigment dispersion liquid thus obtained so as to have a predetermined concentration.
The dye may be dissolved in advance in a part or all of the solvent (E) to prepare a solution. It is preferable to filter the solution with a filter having a pore size of 0.01 μm or more and 1 μm or less.
The colored curable resin composition after mixing is preferably filtered with a filter having a pore size of 0.1 μm or more and 10 μm or less.

(3) Color filter A color filter can be formed from the colored curable resin composition of the present invention. Examples of the method for forming the colored pattern include a photolithographic method, an inkjet method, a printing method and the like. Among them, the photolithographic method is preferable. Photolithographic method, the colored curable resin composition is applied to a substrate, dried to form a colored curable resin composition layer, and the colored curable resin composition layer is exposed through a photomask, It is a method of developing. In the photolithographic method, a colored coating film which is a cured product of the colored curable resin composition layer can be formed by not using a photomask during exposure and/or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

  The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose and application, and is, 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, it is 0.5 μm or more and 6 μm or less.

  As the substrate, a glass plate, a resin plate, silicon, or a substrate on which aluminum, silver, a silver/copper/palladium alloy thin film or the like is formed is used. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or commonly used apparatus and conditions. For example, it can be manufactured as follows.
First, a colored curable resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (prebaking) and/or vacuum drying to dry the layer, and a smooth colored curable resin composition layer is formed. obtain.
Examples of the coating method include a spin coating method, a slit coating method, and a slit and spin coating method.

The temperature for heat drying is preferably 30°C or higher and 120°C or lower, more preferably 50°C or higher and 110°C or lower. The heating time is preferably 10 seconds or more and 60 minutes or less, and more preferably 30 seconds or more and 30 minutes or less.
When drying under reduced pressure, it is preferable to perform drying under a pressure of 50 Pa or more and 150 Pa or less in a temperature range of 20° C. or more and 25° C. or less.
The film thickness of the colored curable resin composition is not particularly limited and may be appropriately selected according to the intended film thickness of the color filter.

  Next, the colored curable resin composition layer is exposed through a photomask for forming an intended colored pattern. An exposure apparatus such as a mask aligner and a stepper can be provided because it is possible to uniformly illuminate parallel light rays on the entire exposed surface and to perform accurate alignment between the photomask and the substrate on which the colored curable resin composition layer is formed. Is preferably used.

  As a light source used for exposure, a light source that emits light having a wavelength of 250 nm or more and 450 nm or less may be used. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light of about 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges. You may. Specific examples thereof include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.

A colored pattern is formed on the substrate by bringing the colored curable resin composition layer after exposure into contact with a developing solution for development. By the development, the unexposed portion of the colored curable resin composition layer is dissolved in the developer and removed.
As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution may be, for example, 0.01% by mass or more and 10% by mass or less. Furthermore, the developing solution may contain a surfactant.
The developing method may be a paddle method, a dipping method, a spray method or the like. Further, the substrate may be tilted at an arbitrary angle during development.
The substrate after development is preferably washed with water.
Furthermore, it is preferable to perform post-baking on the obtained colored pattern.

(4) Display Device The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image sensor, and particularly as a color filter used in a liquid crystal display device. is there.

  Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples, and may be appropriately modified within a range compatible with the gist of the above and the following. Of course, it is possible to carry out, and all of them are included in the technical scope of the present invention. In the following, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified.

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

Synthesis example 1
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.8 parts of glycine (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc acetate (Kanto Chemical ( (Manufactured by K.K.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 150.degree. C. for 7 hours. While maintaining the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) prepared in advance and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing the orange-red precipitate was filtered, and the residue after filtration was washed 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 the compound represented by the formula (II-1) (also referred to as compound II-1) (yield 88%).

<Identification of Compound II-1>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 505
Exact Mass: 506

Synthesis example 2
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.0 parts of 5-aminopentanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc acetate 1.3 parts (manufactured by Kanto Chemical Co., Inc.) and 314 parts imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 150° C. for 14 hours. While maintaining the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) prepared in advance and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing the orange-red precipitate was filtered, and the residue after filtration was washed 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 the formula (II-4) (also referred to as compound II-4) (yield 77%).

<Identification of Compound II-4>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 589
Exact Mass: 590

Synthesis example 3
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 4-amino-3,5-dimethylbenzoic acid (European Journal of Medicinal Chemistry 2014, 78.236). 8.4 parts, zinc acetate (manufactured by Kanto Chemical Co., Inc.), and 314 parts imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added at 150° C., 22 Stir for hours. While maintaining the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) prepared in advance and 1300 parts of water were added, and an orange-red precipitate was formed. The mixture containing the orange-red precipitate was filtered, and the residue after filtration was washed 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 the formula (II-8) (also referred to as compound II-8) (yield 90%).

<Identification of Compound II-8>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 685
Exact Mass: 686

Synthesis example 4
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 was added to 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride. (Manufactured by ComBi Blocks) 2.9 parts of the compound represented by the formula (II-91) (also referred to as compound II-91) in the same manner as in Synthesis Example 1 except that 3.4 parts were used. Obtained (yield 70%).

<Identification of Compound II-91>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 641
Exact Mass: 642

Synthesis example 5
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 was converted to 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride. 3.7 parts of the compound represented by the formula (II-94) (also referred to as compound II-94) was prepared in the same manner as in Synthesis Example 2 except that the amount was changed to 3.4 parts (manufactured by ComBi Blocks). Obtained (yield 79%).

<Identification of Compound II-94>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 725
Exact Mass: 726

Synthesis example 6
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 was converted to 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Aldrich). 2.7 parts of the compound represented by the formula (II-100) (also referred to as compound II-100) was obtained in the same manner as in Synthesis Example 1 except that the amount was changed to 3.5 parts (yield 65. %).

<Identification of Compound II-100>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 661
Exact Mass: 662

Synthesis example 7
An appropriate amount of nitrogen was flown into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2, A mixed solution of 289 parts of a mixture of [ ⁶ ]decane-9-yl acrylate (content ratio is 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of dropping, the mixture was kept at 80° C. for 4 hours, then cooled to room temperature, solid content 35.1%, copolymer (resin B1) solution having a viscosity of 125 mPa·s measured by a B-type viscometer (23° C.). Got The weight average molecular weight Mw of the produced copolymer was 9.2×10 ³ , the dispersity was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. The resin B1 has the following structural units.

<Example 1>
(1) Preparation of Coloring Composition Each component was mixed at the following ratio, and the colorant was dispersed using a bead mill. Then, the bead mill was removed by filtration to obtain a colored composition 1.
Colorant: 50 parts of compound I;
Compound II-1 50 parts;
Dispersant: BYK-LPN6919 (manufactured by BYK Japan KK: solid content 60%) 167 parts;
Resin (B): Resin B1 solution 229 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 3105 parts;
400 parts of diacetone alcohol

Then, the respective components were mixed in the following proportions to obtain a colored curable resin composition 1.
Coloring composition 1 400 parts;
Resin (B): Resin B1 solution 45 parts;
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 25 parts;
Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Ltd.) 15 parts;
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate;
Leveling agent: polyether modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.12 parts

(2) Preparation of Colored Coating Film A 5 cm square glass substrate (Eagle XG; manufactured by Corning Incorporated) was spin-coated with a colored curable resin composition such that the film thickness after post-baking was 1.7 to 2 μm. Method and then prebaked at 100° C. for 3 minutes to form a colored curable resin composition layer. After being left to cool, the colored curable resin composition layer formed on the substrate was exposed to 80 mJ/cm ^{2 in} an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corp.) (365 nm standard). ). After the light irradiation, post-baking was performed in an oven at 230° C. for 30 minutes to obtain a colored coating film.

(3) Heat resistance test The absorbance of the obtained colored coating film was calculated using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). The colored coating film after the measurement was heated in an oven at 230° C. for 120 minutes in an air atmosphere, and then the absorbance was calculated using a colorimeter. The absorbance retention was determined from the absorbance change of the maximum absorption wavelength of the colored curable composition film before and after the heat resistance test.

<Example 2>
A colored curable resin composition 2 was obtained in the same manner as in Example 1 except that the compound (II-4) was used instead of the compound (II-1). The results are shown in Table 4.

<Example 3>
A colored curable resin composition 3 was obtained in the same manner as in Example 1 except that the compound (II-8) was used instead of the compound (II-1). The results are shown in Table 4.

<Example 4>
A colored curable resin composition 4 was obtained in the same manner as in Example 1 except that the amount of the compound (I) was changed to 40 parts and the amount of the compound (II-8) was changed to 60 parts. The results are shown in Table 4.

<Example 5>
A colored curable resin composition 5 was obtained in the same manner as in Example 1 except that the amount of the compound (I) was changed to 60 parts and the amount of the compound (II-8) was changed to 40 parts. The results are shown in Table 4.

<Example 6>
A colored curable resin composition 6 was obtained in the same manner as in Example 1 except that the compound (II-91) was used instead of the compound (II-1). The results are shown in Table 4.

<Example 7>
A colored curable resin composition 7 was obtained in the same manner as in Example 1 except that the compound (II-94) was used instead of the compound (II-1). The results are shown in Table 4.

<Example 8>
A colored curable resin composition 8 was obtained in the same manner as in Example 1 except that the compound (II-100) was used instead of the compound (II-1). The results are shown in Table 4.

<Comparative Example 1>
A colored curable resin composition 9 was obtained in the same manner as in Example 1 except that the colorant was prepared without using the compound (II-1). The results are shown in Table 4.

Claims (7)

A coloring composition comprising a colorant and a resin, wherein the colorant comprises a compound represented by the following formula (I) and a compound represented by the following formula (II).

[In the 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 coloring composition according to claim 1, wherein R ¹ and R ² are divalent aromatic hydrocarbon groups having 1 to 20 carbon atoms. The coloring composition according to claim 1, wherein R ¹ and R ² are each independently an alkanediyl group having 1 to 20 carbon atoms. The coloring composition according to claim 1, wherein R ¹ and R ² are each independently a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms. 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.

[In the 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. ]   A color filter formed from the colored curable resin composition according to claim 5.   A display device including the color filter according to claim 6.