JP7412140B2 - coloring composition - Google Patents

Description

The present invention relates to a colored composition, and further relates 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 perylene compound under the trade name Lumogen (registered trademark) F Orange 240 is known (Patent Document 1).

Japanese Patent Application Publication No. 10-235776

In the field of colorants, there is a demand for improved heat resistance.

An object of the present invention is to provide a colored composition with excellent heat resistance. Another object of the present invention is to provide a colored composition that has 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 colored composition containing a coloring agent and a resin, wherein the coloring agent is a colored composition containing a compound represented by the following formula (I) and a compound represented by the following formula (II). Composition.

[In formula (II),
R ¹ and R ² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms.
R ³ to R ¹⁰ each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. ]
[2] The colored composition according to [1], wherein R ¹ and R ² are divalent aromatic hydrocarbon groups having 1 to 20 carbon atoms.
[3] The colored 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 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 with excellent heat resistance can be provided.

(1) Coloring Composition The coloring composition of the present invention includes a colorant (hereinafter also referred to as colorant (A)) and a resin (hereinafter also referred to as resin (B)).
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 compound (I) and compound (II) (hereinafter also referred to as colorant (A1)).
The colorant (A) may contain one or more colorants (A1).
The colored composition of the present invention may contain a solvent (hereinafter also referred to as solvent (E)).
Compound (I) and compound (II) may be dispersed in solvent (E).

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

Compound (I) can be produced by a well-known general production method, for example, by reacting 3,4,9,10-perylenetetracarboxylic dianhydride and 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 groups represented by R ¹ and R ² may be saturated or unsaturated. Among them, a divalent saturated chain aliphatic hydrocarbon group (hereinafter also referred to as an alkanediyl group) is preferred. 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, and 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 include heptadecane-1,17-diyl group, octadecane-1,18-diyl group, nonadecane-1,19-diyl group, and icosane-1,20-diyl group. Among them, preferably an alkanediyl group having 1 to 10 carbon atoms, more preferably an alkanediyl group having 1 to 4 carbon atoms, and even more preferably a methylene group, ethylene group, propane-1,3-diyl group, butane-1,4- They are diyl group and 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 these, preferred are branched alkanediyl groups having 4 to 10 carbon atoms, more preferred are branched alkanediyl groups having 4 to 6 carbon atoms, and even more preferred are branched alkanediyl groups having 4 to 6 carbon atoms.

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, but-2 -ene-1,4-diyl group, pent-3-ene-1,4-diyl group, and the like.

The divalent alicyclic hydrocarbon group represented by R ¹ and R ² may be saturated or unsaturated. Among these, a divalent saturated alicyclic hydrocarbon group (hereinafter also referred to as a cycloalkanediyl group) is preferred. The cycloalkanediyl group may be monocyclic or polycyclic. Examples of monocyclic cycloalkanediyl groups include cyclopropane-1,2-diyl group, cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cycloalkanediyl group. Examples 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. . Among them, cyclohexane-1,4-diyl group is preferred.

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 (hereinafter also referred to as arenediyl group) represented by R ¹ and R ² may be monocyclic or polycyclic.
Examples of the monocyclic arenediyl group include a benzenediyl group, an alkylbenzenediyl group, and a dialkylbenzenediyl group. Specific examples include benzene-1,2-diyl group, benzene-1,3-diyl group, benzene-1,4-diyl group, 2-methylbenzene-1,4-diyl group, 3-methylbenzene-1 ,4-diyl group, 2-methylbenzene-1,5-diyl group, 3-methylbenzene-1,5-diyl group, 4-methylbenzene-1,5-diyl group, 2-ethylbenzene-1,4- 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, [1,1'-biphenyl]-4,4 '-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, They are 2-methylbenzene-1,4-diyl group, 2-ethylbenzene-1,4-diyl group, and 3-ethyl-5-methylbenzene-1,4-diyl group.

R ¹ and R ² are each independently preferably selected from the group consisting of an alkanediyl group having 1 to 20 carbon atoms, a cycloalkanediyl group having 3 to 20 carbon atoms, and an arenediyl group having 6 to 20 carbon atoms. More preferably, it is a group selected from the group consisting of an alkanediyl group having 1 to 10 carbon atoms, a cycloalkanediyl group having 3 to 10 carbon atoms, and an arenediyl group 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. , still 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 each independently be a group that is a combination of two or more of the above hydrocarbon groups, such as a group that is a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group, or an aromatic hydrocarbon group. The group may be a combination of a hydrogen group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group. The total number of carbon atoms in these combined groups is 20 or less.

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

Specific examples of R ¹ and R ² include groups represented by the following formulas. * and ** represent bonds.

Preferable R ¹ and R ² are each independently the formulas (A-1) to (A-8), (A-14), (B-1) to (B-3), and (B-16 ) to (B-19) or (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. Among them, fluorine atoms and chlorine atoms are preferred.

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 chain or cyclic.

Examples of the saturated or unsaturated chain aliphatic hydrocarbon group represented by R ³ to R ¹⁰ include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, Decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group , heptacocyl 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 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 , 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, 2-pentenyl group, and other alkenyl groups; etc. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10. Among these, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferred, and a methyl group or an ethyl group is particularly preferred.

The saturated or unsaturated alicyclic hydrocarbon group represented by R ³ to R ¹⁰ includes 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 - cycloalkyl groups such as tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group; cyclohexenyl group (e.g. cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, Cycloalkenyl groups such as a cyclooctenyl group; examples include a norbornyl group, an adamantyl group, a bicyclo[2.2.2]octyl group, and the like. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, particularly preferably 4 to 15, The number is more preferably 5 to 15, particularly preferably 5 to 10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group is most preferred.

The aromatic hydrocarbon group represented by R ³ to R ¹⁰ includes 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 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 group 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 still more preferably 6 to 15 carbon atoms.

The hydrocarbon groups represented by R ³ to R ¹⁰ include a combination of two or more of the hydrocarbon groups listed above, such as an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group. Examples include aralkyl groups such as benzyl group, phenethyl group, and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group). ; Arylalkynyl groups such as phenylethynyl groups; phenyl groups to which one or more phenyl groups are bonded such as biphenylyl groups and terphenylyl groups; cyclohexylmethylphenyl groups, benzylphenyl groups, (dimethyl(phenyl)methyl)phenyl groups, etc. It will be done.

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

The number of carbon atoms in the group in which two or more of the above hydrocarbon groups are combined is preferably 4 to 30, more preferably 4 to 20, still more preferably 4 to 15, and even more preferably 6 to 15.

Examples of substituents that the hydrocarbon group having 1 to 40 carbon atoms represented by R ³ to R ¹⁰ may have include, for example, a halogen atom, a formyl group, a carboxy group, a formyloxy group, a hydroxy group, and a thiol group. group, sulfo group, sulfamoyl group, pentafluorosulfanyl group, carbamoyl group, amino group, nitro group, cyano group, -COR ¹² , -COOR ¹² , -OCOR ¹² , -OR ¹² , -SR ¹² , -SOR ¹² , - SO ₂ R ¹² , -SO ₂ NHR ¹² , -SO ₂ NR ¹² R ¹³ , -CONHR ¹² , -CONR ¹² R ¹³ , -NHR ¹² , -NR ¹² R ¹³ , -NHCOR ¹² , -NR ¹³ COR ¹² , etc. Can be mentioned.

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

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

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

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

-COR ¹² includes acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, Examples include undecanoyl group, dodecanoyl group, henicosanoyl group, and 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 Examples include carbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, and the like.

-OCOR ¹² includes acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl)hexanoyloxy group, heptanoyloxy group, Noyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, 2-propenylcarbonyloxy group Examples include groups.

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

-SR ¹² includes methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, butylsulfanyl group, tert-butylsulfanyl group, pentylsulfanyl group, hexylsulfanyl group, (2-ethyl)hexylsulfanyl group, heptylsulfanyl group, octyl Examples include sulfanyl group, nonylsulfanyl group, decylsulfanyl group, undecylsulfanyl group, dodecylsulfanyl group, icosylsulfanyl group, phenylsulfanyl group, and o-tolylsulfanyl group.

-SOR ¹² includes a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, a phenylsulfinyl group, a naphthylsulfinyl group, and the like.

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

-SO ₂ NHR ¹² includes N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N- Isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group Moyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N- Examples include undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamoyl group, and N-phenylsulfamoyl group.

-SO ₂ NR ¹² R ¹³ is N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group 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)hexylsulfamoyl group 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 include octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamoyl group, N-phenylcarbamoyl group, and the like.

-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-di-tert-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 N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N- Examples include decylamino group, N-undecylamino group, N-dodecylamino group, N-icosylamino group, N-phenylamino group, and the like.

-NR ¹² R ¹³ includes 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 -di-tert-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 group, N,N-undecylmethylamino group, N,N-dodecylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc. It will be done.

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

-NR ¹³ COR ¹² includes N-methyl-N-acetylamino group and the like.

-CH ₂ - included in the hydrocarbon group having 1 to 40 carbon atoms represented by R ³ to R ¹⁰ and not forming a ring is -O-, -CO-, -S(O) ₂ -, - It may be replaced by NR ^x1 -. However, -COOH and -S(O) ₂ OH are not formed by replacing -CH ₂ -. 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.

R ³ to R ¹⁰ are preferably hydrogen atoms, halogen atoms, hydroxy groups, nitro groups, cyano groups, -CH ₃ , formulas (D-1) to (D-18), (E-1) to (E -27), (F-1) to (F-18) and (G-1) to (G-27). The halogen atom is preferably a chlorine atom or a bromine atom. When these atoms are included as halogen atoms, colored patterns and colored coating films formed from the colored curable resin composition tend to exhibit excellent heat resistance and 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 compound (II) include compounds shown in Tables 1 to 3 below.

Among them, compounds (II-1) to (II-9) and (I-82) to (I-117) are preferred, and from the viewpoint of heat resistance and light resistance, compounds (II-2) to (II -6), (II-8), (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 compound (II) in the present invention includes a compound represented by the following formula (IIa) (hereinafter also referred to as compound (IIa)).

[In formula (IIa),
R ^1a and R ^2a each independently represent an alkanediyl group having 1 to 20 carbon atoms.
R ^3a to R ^10a each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. ]

Examples of the alkanediyl group represented by R ^1a and R ^2a are the same as those exemplified in the explanation of R ¹ and R ² in chemical formula (II).

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

Specific examples of compound (IIa) include compounds (II-1) to (II-6), (II-10) to (II-15), and (II-19) to (II-19) 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), Examples include (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 compound (II) in the present invention is a compound represented by the following formula (IIb) (hereinafter also referred to as compound (IIb)).

[In formula (IIb),
R ^1b and R ^2b each independently represent a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms.
R ^3b to R ^10b each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. ]

Examples of the divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by R ^1b and R ^2b include those having 1 to 20 carbon atoms in the explanation 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 chemical formula (II).

Specific examples of compound (IIb) include compounds (II-9), (II-18), (II-27), (II-36), (II-45), (II -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。］ Other preferred embodiments of compound (II) in the present invention include a compound represented by the following formula (IIc) (hereinafter also referred to as compound (IIc)).

[In formula (IIc),
R ^1c and R ^2c each independently represent a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms.
R ^3c to R ^10c each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. ]

Examples of the divalent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by R ^1c and R ^2c include 2 having 1 to 20 carbon atoms in the explanation of R ¹ and R ² in the above chemical formula (II). This is the same as the example of the aromatic hydrocarbon group.

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

Specific examples of compound (IIc) include compounds (II-7), (II-8), (II-16), (II-17), (II-25), (II -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), Examples include (I-106), (I-107), (I-115), and (I-116).

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。］

[In the formula, 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 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 formula (ca1) include the divalent hydrocarbon group having 1 to 20 carbon atoms in the explanation of R ¹ and R ² in the above compound (II). This is the same as the example of the hydrocarbon group.

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

The amount of the compound represented by formula (ca1) to be used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, per 1 mol of the compound represented by formula (pt1). , more preferably 1 mol or more and 6 mols or less, still more preferably 1 mol or more and 4 mols 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 solvents such as 1-octanol and phenol; Ether solvents such as diethyl ether and tetrahydrofuran; Ketone solvents such as acetone and methyl isobutyl ketone; Ester solvents such as ethyl acetate; Aliphatic hydrocarbon solvents such as hexane; Aromatic solvents 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; and sulfoxide solvents such as dimethyl sulfoxide.

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

The reaction temperature is usually -100°C or more and 300°C or less, preferably -90°C or more and 200°C or less, and more preferably -10°C or more and 150°C or less.

After completion of the reaction, the method for removing compound (II) is not particularly limited, and it can be removed by various known methods. Compound (II) can be removed, for example, by distilling off the solvent. Furthermore, after distilling off the solvent, the resulting residue may be purified by column chromatography, recrystallization, or the like. Moreover, after the reaction is completed, compound (II) can be taken out by filtration. Moreover, 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 using known analytical techniques and conditions. Such analysis methods include, but are not particularly limited to, X-ray crystallography, mass spectrometry (LC), NMR analysis, elemental analysis, and the like. The X-ray crystal structure analysis method is described in, for example, Chemistry of Materials, 2012, Vol. 24, p. 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) can be produced, for example, by reacting a compound represented by the following formula (pt1) and a compound represented by the following formula (ca1a) (hereinafter also referred to as compound (ca1a)) in a solvent. Can be done.

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

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

Specific examples of compound (ca1a) include 2-aminoethanoic acid (glycine), 3-aminopropanoic acid, 4-aminobutanoic acid, 5-aminopentanoic acid, 6-aminohexanoic acid, 7-aminoheptanoic acid, and 8-aminoheptanoic acid. 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, Examples include 2-amino-3-methylpentanoic acid.

［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) can be produced, for example, by reacting a compound represented by the following formula (pt1) and a compound represented by the following formula (ca1b) (hereinafter also referred to as compound (ca1b)) in a solvent. Can be done.

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

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

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

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

<Coloring agent (A)>
The content of 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), More preferably 1% by mass or more, still more preferably 5% by mass or more, particularly preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 50% by mass or more. On the other hand, the content of compound (I) in the colorant (A) is usually less than 100% by mass, and may be, for example, 99% by mass or less, based on the total amount of the colorant (A).

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

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

The content of the coloring agent (A) in the coloring composition may be, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 0.1% by mass or more and 99.9% by mass or less, based on the total amount of solids in the coloring composition. 5% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 90% by mass or less, even more preferably 5% by mass or more and 80% by mass or less, particularly preferably 10% by mass or more and 70% by mass or less. It is more preferably 15% by mass or more and 60% by mass or less, even more preferably 20% by mass or more and 50% by mass or less, particularly preferably 25% by mass or more and 45% by mass or less, and extremely preferably 30% by mass or less. It is not less than 40% by mass and not more than 40% by mass.
As used herein, "total amount of solid content in the coloring composition" refers to the total amount of components excluding all solvent components from the coloring composition. The total solid content and the content of each component relative to the total solid content can be measured by known analytical 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, such as those described in Color Index (published by The Society of Dyers and Colourists) and Dyeing Note (Shirosensha). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline Examples include dyes, nitro dyes, phthalocyanine dyes, perylene dyes, and the like. These dyes may be used alone or in combination of two or more.

Specifically, dyes having the following color index (C.I.) numbers may be mentioned.
C. I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63,
68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
C. I. Solvent red 24, 45, 49, 90, 91111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
C. I. Solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. C.I. such as Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. 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 dye,
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. C. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82, etc. I. direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C.I. such as Disperse Blue 1, 14, 56, 60, etc. 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. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern 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. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. C. mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. I. mordant dye,
C. I. Bat green 1st class C. I. Vat dye etc.

Further examples include 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).

As the pigment, known pigments can be used, such as pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). These may be used alone or in combination of two or more.
Specifically, C. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231;
C. I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, Red pigments such as 265, 266, 268, 269, 273;
C. I. Blue pigments such as Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
C. I. Violet color pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as Pigment Green 7, 36, 58, 59, 62, 63;
C. I. Brown pigments such as Pigment Brown 23 and 25;
C. I. Examples include black pigments such as Pigment Black 1, 7, 31, and 32.

The colorant (A1) may be treated, if necessary, by rosin treatment, surface treatment using a derivative with an acidic or basic group introduced therein, grafting treatment on the surface of the colorant (A1) with a polymer compound, etc., or sulfuric acid. Atomization treatment using an atomization method, washing treatment with an organic solvent, water, etc. to remove impurities, removal treatment of ionic impurities by an ion exchange method, etc. may be performed. The particle size of the colorant (A1) is preferably substantially uniform.

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

When the colorant (A) further contains a 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. 99% by mass or less, for example, it may be 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, more preferably 0.7% by mass or more and 70% by mass. % or less, particularly preferably 1% by mass or more and 60% by mass or less.

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

The content of solids 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. mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, still more preferably 1 mass% or more and 60% or less, even more preferably 3 It is at least 3% by mass and at most 30% by mass, particularly preferably at least 3% by mass and at most 30% by mass, and extremely preferably at least 5% by mass and at most 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 based on the total amount of solids in the colorant-containing liquid. and more preferably 0.01% by mass or more and 99% by mass or less, still more 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 even more preferably Preferably it is 2% by mass or more and 99% by mass or less.
In this specification, the "total amount of solid content in the colorant-containing liquid" refers to the total amount of components excluding the solvent (E) from the colorant-containing liquid. The total solid content and the content of each component relative to the total solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.

By incorporating a dispersant into the colorant (A) and performing a dispersion treatment, the colorant (A) can be uniformly dispersed in the colorant-containing liquid. The coloring agents (A) may be dispersed individually, or a plurality of them may be mixed and dispersed.

Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric surfactants. Specific examples include polyester-based, polyamine-based, acrylic-based surfactants, and the like. These dispersants may be used alone or in combination of two or more. As a dispersant, the trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (registered trademark) (manufactured by Zeneca Corporation), and EFKA (registered trademark). (manufactured by BASF Co., Ltd.), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK Chemie Co., Ltd.), etc. 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 10,000 parts by mass or less, based on 100 parts by mass of the colorant (A). 5000 parts by mass or less, more preferably 1000 parts by mass or less, even more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, even more preferably 200 parts by mass or less, even 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 within the above range, a colorant-containing liquid with a more uniformly dispersed state tends to be obtained.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, containing 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 to use a polymer having 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 others. It is preferable that it is a copolymer having a structural unit of
Other structural units include monomers copolymerizable with monomer (a) (however, they are different from monomer (a) and monomer (b); hereinafter referred to as "monomer (c)") Examples include structural units derived from (sometimes referred to as), structural units having ethylenically unsaturated bonds, and the like.

Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and 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-cyclohexenedicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, Bicyclounsaturated 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 acid anhydrides such as anhydrides of the above unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyhydric carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate. Class;
Examples 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 preferred from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one member selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. means. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
As the monomer (b), for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), an oxetanyl group and an ethylenically unsaturated bond, etc. (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)") ) etc.

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)") ) and a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "monomer (b1-2)").

The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond.
Specifically, the monomer (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, vinylbenzylglycidyl ether, α- Methylvinylbenzylglycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxy) methyl) styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4, Examples include 5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene.
As the monomer (b1-2), 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 Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Corporation) , a compound represented by formula (BI), a compound represented by formula (BII), and the like.

[In formula (BI) and formula (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 each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-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 methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.

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

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

Examples of alkanediyl groups 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, Examples include hexane-1,6-diyl group.

Preferably, X ^a and X ^b include a single bond, a methylene group, an ethylene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, and more preferably a single bond, *-CH ₂ Examples include CH ₂ -O- (* represents a bond with O).

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

Examples of the compound represented by formula (BII) include compounds represented by any one of formula (BII-1) to formula (BII-15), among which compounds represented by formula (BII-1) and formula (BII-15) are preferred. (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formulas (BII-11) to (BII-15), and more. Preferred are compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination with the compound represented by formula (BI) and the compound represented by formula (BII). You may. When these are used together, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10: The ratio is 90 to 90:10, 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-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3 -Acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. can be 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 (eg, Viscoat V #150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

As the monomer (b), monomer (b1) is preferable because it can further improve the reliability of the heat resistance, chemical resistance, etc. of the color filter obtained. Furthermore, monomer (b1-2) is more preferred in that the coloring composition has excellent storage stability.

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)acrylate, ) (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 esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate;
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) bicyclounsaturated compounds such as (oxycarbonyl)bicyclo[2.2.1]hept-2-ene;
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 maleimidopropionate and N-(9-acridinyl)maleimide;
Aromatic compounds containing vinyl groups such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; Nitriles containing vinyl groups such as (meth)acrylonitrile; Halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth)acrylamide Examples include vinyl group-containing amides such as; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene;
Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decane-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, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, benzyl (meth)acrylate, and the like are preferred.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. A resin having such a structural unit is a polymer having a structural unit derived from monomer (a) or monomer (b), and a group possessed by monomer (a) or monomer (b). It can be obtained by adding a monomer having an ethylenically unsaturated bond to a group capable of reacting with.
Such structural units 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 a structural unit in which glycidyl (meth)acrylate is added to a maleic anhydride unit. ) Examples include structural units in which (meth)acrylic acid is added to acrylate units. Furthermore, when these structural units have a hydroxy group, structural units to which carboxylic acid anhydride is further added are also included as structural units having ethylenically unsaturated bonds.

A polymer having a structural unit derived from monomer (a) can be produced, for example, by polymerizing monomers constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, solvent, etc. are not particularly limited, and those commonly used in the field can be used. For example, as a polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) The solvent may be any solvent as long as it dissolves each monomer.

In addition, the obtained polymer may be used as it is as a solution after the reaction, a concentrated or diluted solution may be used, or it may be taken out as a solid (powder) by a method such as reprecipitation. may be used.
If necessary, a catalyst for the reaction between a carboxylic acid or a carboxylic acid anhydride and a cyclic ether (for example, tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (for example, hydroquinone, etc.) may be used.
Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

Specifically, the resin (B) includes 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 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-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5 .2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth) ) acrylate/(meth)acrylic acid/2-ethylhexyl (meth)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- Examples include resins described in each publication such as No. 361455.
Among these, as the resin (B), a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) is preferable.

Two or more resins (B) may be used in combination, and 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-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxy It is preferable to contain 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) of the resin (B) in terms of polystyrene is preferably 1,000 or more and 100,000 or less, more preferably 1,000 or more and 50,000 or less, and still more preferably 1,000 or more. It is 30,000 or less, 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 still more preferably 1.001 or more and 4 or less. 01 or more and 4 or less.

The acid value (solid content equivalent 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, and even more preferably 20 mg-KOH/g. -KOH/g or more and 200mg-KOH/g or less, particularly preferably 20mg-KOH/g or more and 170mg-KOH/g or less, even more preferably 30mg-KOH/g or more and 170mg-KOH/g or less, particularly preferably 60mg-KOH /g or more and 150 mg-KOH/g or less, extremely preferably 65 mg-KOH/g or more and 135 mg-KOH/g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

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

After preparing a colorant-containing liquid in advance, when the colorant-containing liquid is used to prepare the colored composition of the present invention, the colorant-containing liquid is a mixture of the resin (B) described below contained in the coloring composition. A part or all of it, preferably a part of it, may be included in advance. By including the resin (B) in advance, the dispersion stability of the colorant-containing liquid can be further improved.

The content of the resin (B) in the colorant-containing liquid may be, for example, 10,000 parts by mass or less, preferably 5,000 parts by mass or less, and more preferably 1,000 parts by mass, based on 100 parts by mass of the colorant (A). It 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, and even 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 colored composition according to Embodiment 1 is a colored composition containing a coloring agent (A) and a resin (B), wherein the coloring agent (A) is a compound represented by formula (I) and the following: This is a colored composition containing a 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 preferred ranges of the contents of compound (I) and compound (IIa) in the colorant (A) are as follows: It is the same as the example and preferred range.

［式（ＩＩｂ）中、Ｒ^１ｂ～Ｒ^１０ｂの定義は上述の定義と同一である。］ <Embodiment 2>
The colored composition according to Embodiment 2 is a colored composition containing a coloring agent (A) and a resin (B), wherein the coloring agent (A) is a compound represented by formula (I) and the following: This is a colored composition containing a 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 preferred ranges of the contents of compound (I) and compound (IIb) in the colorant (A) are as follows: It is the same as the example and preferred range.

［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 colored composition according to Embodiment 3 is a colored composition containing a coloring agent (A) and a resin (B), where the coloring agent (A) contains a compound (IIc).

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

Examples and preferred ranges of the contents of compound (I) and compound (IIc) in the colorant (A) are as follows: It is the same as the example and preferred range.

(2) Colored curable resin composition The colored curable resin composition contains compound (I), compound (II), resin (B) (hereinafter also collectively referred to as colorant (A)), It contains a polymerizable compound (hereinafter sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)).
The colored curable resin composition consists of 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 solid content in the colored curable resin composition is adjusted as appropriate depending on 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, more preferably 1% by mass or more and 90% by mass or less, based on the total amount of solids in the colored curable resin composition. is 2% by mass or more and 80% by mass or less, more preferably 3% by mass or more and 70% by mass or less, particularly preferably 4% by mass or more and 60% by mass or less, even more preferably 5% by mass or more and 50% by mass. It is particularly preferably 6% by mass or more and 45% by mass or less, and extremely 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 adjusted appropriately depending on the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured, and therefore is not particularly limited. However, it 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, more preferably 2% by mass or less, based on the total amount of solids in the colored curable resin composition. % by mass or more and 80% by mass or less, more preferably 3% by mass or more and 70% by mass or less, particularly preferably 4% by mass or more and 60% by mass or less, even more preferably 5% by mass or more and 50% by mass or less. The content is particularly preferably 8% by mass or more and 40% by mass or less, and extremely preferably 10% by mass or more and 30% by mass or less.

As used herein, "the total amount of solid content in the colored curable resin composition" refers to the total amount of the components excluding the solvent (E) from the colored curable resin composition. The total amount of solid content and the content of each component relative to the total amount can be measured by known analytical 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, preferably 0.1% by mass, based on the total amount of the colored curable resin composition. 99.9% 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 60% by mass, even more preferably 3% by mass or more and 50% by mass or less. , even more preferably 3% by mass or more and 30% by mass or less, particularly preferably 5% by mass or more and 30% by mass or less.

The colored patterns and colored coating films described below formed from the colored curable resin composition of the present invention not only have excellent heat resistance but also tend to have high transmittance at a wavelength of 630 nm, and preferably contain compound (I) alone. 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 a 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 of, for example, 90% or more at a wavelength of 630 nm, preferably 95% or more, and more preferably 97% or more. % 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 active radicals and/or acids generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond. It is a (meth)acrylic acid ester compound.

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. etc., and the above-mentioned monomers (a), monomers (b) and monomers (c).

Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, and triethylene glycol di(meth)acrylate. Examples include (meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol 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 include caprolactone-modified pentaerythritol tetra(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate, 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 4,000 or less, more preferably 50 or more and 3,500 or less, even more preferably 50 or more and 3,000 or less, particularly preferably 150 or more and 2,900 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 solid content 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 even more preferably 6% by mass or less. It is from 7% by mass to 40% by mass, 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 that can initiate polymerization by generating active radicals, acids, etc. under the action of light or heat, and any known polymerization initiator can be used.

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

Examples of O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, 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 include cyclopentylpropan-1-one-2-imine. Further, as the O-acyloxime compound, commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF Corporation) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, 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 preferred, and N-benzoyl More preferred is oxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine.

Examples of alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1- and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. As the alkylphenone compound, commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF Corporation) may be used.
Examples of alkylphenone compounds 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-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyl dimethyl ketal.

Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4 , 4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4, 4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2 '-Bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Unexamined Patent Publication No. 174204-1984, etc.) and biimidazole compounds in which the phenyl group at the 4,4′,5,5′-position is substituted with a carbalkoxy group (see, for example, JP-A-7-10913).

As triazine compounds, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)- 1,3,5-triazine, 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) Examples include 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 Corporation) may be used.

Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, o-benzoyl methyl benzoate, 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, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.
These are preferably used in combination with the polymerization initiation aid (D1) (especially amines) described below.

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

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

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

Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and 4-dimethylaminobenzoate. 2-ethylhexyl dimethylaminobenzoate, N,N-dimethylpara-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis( Examples include ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. Furthermore, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used.

Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy Examples 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.

Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.

When using these polymerization initiation aids (D1), the content thereof 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). The content is often 0.1% by mass or more and 30% by mass or less.

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

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

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

Ether ester solvents include methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 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 include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

Ketone solvents 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 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, more preferably 0.1% by mass or more and 99.9% by mass or less, 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, even more preferably 50% by mass or more and 90% by mass or less. It is not more than 60% by mass and not more than 95% by mass, particularly preferably not less than 70% by mass and not more than 90% by mass.

The colored curable resin composition of the present invention can be 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 also be prepared using a colorant-containing liquid.

The content of solids 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. .9 mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, still more preferably 1 mass% or more and 90 mass% or less, and even more preferably 1 mass% or more and 60% or less. , 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 extremely preferably 5% by mass or more and 30% by mass or less.

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

When preparing a colorant-containing liquid by dispersing all or part of compound (I) and compound (II) in all or part of solvent (E), all or part of resin (B) may not be included. By keeping it in place, 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, 10,000 parts by mass or less, preferably 5,000 parts by mass or less, based on a total of 100 parts by mass of compound (I) and compound (II). , more preferably 1000 parts by mass or less, still more 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, even more preferably 10 parts by mass or more and 100 parts by mass or less. It is.

Compound (I) and compound (II) can be treated, if necessary, with rosin treatment, surface treatment with a derivative having an acidic group or basic group introduced therein, and compound (I) and compound (II) with a polymer compound or the like. ) Even if surface grafting treatment, atomization treatment using sulfuric acid atomization method, cleaning treatment using organic solvents, water, etc. to remove impurities, removal treatment such as ion exchange method for ionic impurities, etc. good. The particle sizes of compound (I) and compound (II) are preferably substantially uniform.

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

Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric surfactants. Specific examples include polyester-based, polyamine-based, acrylic-based surfactants, and the like. These dispersants may be used alone or in combination of two or more. As a dispersant, the trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (registered trademark) (manufactured by Zeneca Corporation), and EFKA (registered trademark). (manufactured by BASF Co., Ltd.), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK Chemie Co., Ltd.), etc. Can be mentioned.

When using a dispersant, the amount of the dispersant (solid content) used is 10,000 parts by mass or less, preferably 5,000 parts by mass or less, based on a total of 100 parts by mass of compound (I) and compound (II). 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, even more preferably 100 parts by mass or less, even more preferably 5 parts by mass or more and 100 parts by mass. Parts 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 with a more uniformly 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 surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms. These may have a polymerizable group in the side chain.
Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Dow Corning Toray 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, Florado (registered trademark) FC430, Florado FC431 (manufactured by Sumitomo 3M Ltd.), Megafac (registered trademark) F142D, Florado (registered trademark) F171, Florado F172, Florado F173, Florado F177, Florado F183, Florado F554, Megafac (registered trademark) R30, RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Examples include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute).

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

When containing a leveling agent (F), its content is usually 0.0005% by mass or more and 5% by mass or less, preferably 0.001% by mass or more and 1% by mass or less, based on 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, particularly preferably 0.005 mass% or more It is 0.1% by 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. The antioxidant is not particularly limited as long as it is an antioxidant commonly used industrially, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like can be used.

Examples of the phenolic antioxidant include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF Corporation), 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 Corporation), Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H )-trione, manufactured by BASF Corporation), Irganox 3790:1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3, 5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), Irganox 1035 (Irganox 1035: thiodiethylenebis[3-(3,5-di-tert-butyl- 4-hydroxyphenyl)propionate], manufactured by BASF Corporation), 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 (4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Corporation), Irganox 3125 (Irganox 3125, manufactured by BASF Corporation) ), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy 3',5'-di-tert-butylanilino)-1,3,5-triazine, BASF Corporation ), 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 (Sumilizer GA- Examples include Sumilizer GS (manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec Co., Ltd.), and Vitamin E (manufactured by Eisai Co., Ltd.). .

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

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

<Other ingredients>
The colored curable resin composition of the present invention may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, light stabilizers, and chain transfer agents, as necessary. .
Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycid Xypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercapto Propyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-amino Propylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3 Examples include -aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropyltriethoxysilane.

<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), and when patterning is performed by a photolithography method, a polymerizable compound (C), It can be prepared by mixing together a polymerization initiator (D), a polymerization initiation aid (D1), and other components.
It is preferable that the pigment is mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes approximately 0.2 μm or less. At this time, part or all of the pigment dispersant and resin (B) may be blended as necessary. The desired colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion obtained in this way to a predetermined concentration.
The dye may be dissolved in part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution using a filter with a pore size of approximately 0.01 μm or more and 1 μm or less.
It is preferable that the colored curable resin composition after mixing is filtered through a filter with a pore size of approximately 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 a colored pattern include a photolithography method, an inkjet method, and a printing method. Among these, photolithography is preferred. In the photolithography 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 to light through a photomask. This is a method of developing. In the photolithography method, by not using a photomask during exposure and/or not developing, a colored coating film that is a cured product of the colored curable resin composition layer can be formed. The colored pattern and colored coating film thus formed are the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited, and can be adjusted as appropriate depending on the purpose, use, etc., 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 a thin film of aluminum, silver, silver/copper/palladium alloy, etc. is formed is used. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

Formation of each color pixel by photolithography can be performed using known or conventional equipment and conditions. For example, it can be produced as follows.
First, a colored curable resin composition is applied onto a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and/or reduced pressure drying to form a smooth colored curable resin composition layer. obtain.
Examples of the coating method include spin coating, slit coating, and slit-and-spin coating.

The temperature when performing heat drying is preferably 30°C or more and 120°C or less, more preferably 50°C or more and 110°C or less. Further, 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 is performed, it is preferably carried out under a pressure of 50 Pa or more and 150 Pa or less and at a temperature range of 20° C. or more and 25° C. or less.
The thickness of the colored curable resin composition is not particularly limited, and may be appropriately selected depending on the thickness of the intended color filter.

Next, the colored curable resin composition layer is exposed through a photomask to form a desired colored pattern. Exposure equipment such as mask aligners and steppers can uniformly irradiate the entire exposure surface with parallel light and accurately align the photomask and the substrate on which the colored curable resin composition layer is formed. It is preferable to use

As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less may be used. For example, light of less than 350 nm can be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a band pass filter that extracts these wavelength ranges. You can also Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.

A colored pattern is formed on the substrate by bringing the exposed colored curable resin composition layer into contact with a developer and developing it. By development, the unexposed areas of the colored curable resin composition layer are dissolved in the developer and removed.
As the developer, 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 developer may contain a surfactant.
The developing method may be any of the paddle method, dipping method, spray method, etc. Furthermore, 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 post-bake the obtained colored pattern.

(4) Display device The color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors, especially as a color filter used in liquid crystal display devices. be.

Hereinafter, the present invention will be explained in more detail with reference to Examples. However, the present invention is not limited by the Examples, and modifications may be made as appropriate within the scope of the spirit of the above and below. Of course, other implementations are also possible, and all of them are included within the technical scope of the present invention. In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass."

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

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

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 (manufactured by Kanto Chemical Industry Co., Ltd.) 1.3 parts of Imidazole (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added, and the mixture was stirred at 150°C for 7 hours. When 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Kagaku Co., Ltd.) and 1300 parts of water were added to the resulting mixture while keeping the temperature below 20°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the filtered residue 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 a compound represented by formula (II-1) (also referred to as compound II-1) (yield: 88%).

<Identification of compound II-1>
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 505
Exact Mass: 506

Synthesis example 2
3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.0 parts, 5-aminopentanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 6.0 parts, zinc acetate (manufactured by Kanto Kagaku Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 150° C. for 14 hours. When 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Kagaku Co., Ltd.) and 1300 parts of water were added to the resulting mixture while keeping the temperature below 20°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the filtered residue 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 formula (II-4) (also referred to as compound II-4) (yield 77%).

<Identification of compound II-4>
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 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 of zinc acetate (manufactured by Kanto Kagaku Co., Ltd.), and 314 parts of imidazole (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added, and the mixture was heated at 150°C at 22 Stir for hours. When 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Kagaku Co., Ltd.) and 1300 parts of water were added to the resulting mixture while keeping the temperature below 20°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the filtered residue 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 formula (II-8) (also referred to as compound II-8) (yield 90%).

<Identification of compound II-8>
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 685
Exact Mass: 686

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

<Identification of compound II-91>
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 641
Exact Mass: 642

Synthesis example 5
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride of Synthesis Example 1 was converted to 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride. (manufactured by ComBi Blocks) 3.7 parts of the compound represented by 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. (yield 79%).

<Identification of compound II-94>
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 725
Exact Mass: 726

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

<Identification of compound II-100>
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 661
Exact Mass: 662

Synthesis example 7
A suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added thereto, and the flask was heated to 80° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2, A mixed solution of 289 parts of a mixture of decane-9-yl acrylate (content ratio: 1:1 in molar ratio) and ¹²⁵ parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, 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 the dropwise addition was completed, the temperature was maintained at 80°C for 4 hours, and then cooled to room temperature to prepare a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s measured with a B-type viscometer (23°C). I got it. The weight average molecular weight Mw of the produced copolymer was 9.2×10 ³ , the degree of dispersion was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. Resin B1 has the following structural units.

<Example 1>
(1) Preparation of colored composition Each component was mixed in the following proportions, and the coloring agent was dispersed using a bead mill. Thereafter, the bead mill was removed by filtration to obtain Colored Composition 1.
Colorant: Compound I 50 parts;
Compound II-1 50 parts;
Dispersant: BYK-LPN6919 (manufactured by BYK Chemie Japan Co., Ltd.: solid content 60%) 167 parts;
Resin (B): 229 parts of resin B1 solution;
Solvent (E): 3105 parts of propylene glycol monomethyl ether acetate;
Diacetone alcohol 400 parts

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

(2) Preparation of colored coating film Spin coat a colored curable resin composition on a 5 cm square glass substrate (Eagle After coating by the method, prebaking was performed at 100° C. for 3 minutes to form a colored curable resin composition layer. After cooling, the colored curable resin composition layer formed on the substrate was exposed to a light dose of 80 mJ/cm ² (365 nm standard) using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) in an air atmosphere. ) was irradiated with light. After the light irradiation, post-baking was performed at 230° C. for 30 minutes in an oven 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 in an air atmosphere at 230° C. for 120 minutes, and then the absorbance was calculated using a colorimeter. The absorbance retention rate was determined from the change in absorbance at the maximum absorption wavelength of the colored curable composition film before and after the heat resistance test.

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

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

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

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

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

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

<Example 8>
Colored curable resin composition 8 was obtained in the same manner as in Example 1 except that compound (II-1) was replaced with compound (II-100). The results are shown in Table 4.

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

Claims (7)

A coloring composition containing a colorant and a resin, the colorant containing a compound represented by the following formula (I) and a compound represented by the following formula (II) ,
A colored composition in which the mass ratio of the compound represented by formula (I) and the compound represented by formula (II) is 30:70 to 70:30 .

[In formula (II),
R ¹ and R ² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms.
R ³ to R ¹⁰ each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. ] The colored composition according to claim 1, wherein R ¹ and R ² are divalent aromatic hydrocarbon groups having 1 to 20 carbon atoms. The colored 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. 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,
A colored curable resin composition in which the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) is 30:70 to 70:30 .

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