JP7241514B2 - Colored composition, colored curable resin composition, color filter and display device - Google Patents

Description

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

Potassium salts of perylene tetracarboxylic acids have been proposed in the field of gas separation membranes to exhibit excellent CO ₂ separation performance (Non-Patent Document 1).

Chemistry of Materials, 2012, Vol. 24, p. 4647-4652

In the field of colorants, improvements in heat resistance and light resistance are required.

An object of the present invention is to provide a colored composition having good heat resistance and light resistance.

［式中、
Ｒ^１～Ｒ^３は、互いに独立に、水素原子、－ＣＯ_２ ^－、ハロゲン原子、シアノ基、ニトロ基、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。
Ｒ^４～Ｒ^１１は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基、ニトロ基、－ＣＯ_２ ^－、又は－Ｓ（Ｏ）_２Ｏ^－を表す。
前記Ｒ^４～Ｒ^１１で表される置換基を有していてもよい炭素数１～４０の炭化水素基に含まれ、かつ環を構成しない－ＣＨ_２－、及び前記Ｒ^４～Ｒ^１１で表される置換基を有していてもよい複素環基に含まれ、かつ環を構成しない－ＣＨ_２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）_２－、－ＮＲ^ｘ１－に置き換わっていてもよい。ただし、前記－ＣＨ_２－が置き換わることで－ＣＯＯＨ及び－Ｓ（Ｏ）_２ＯＨが形成されることはない。
前記Ｒ^ｘ１は、水素原子、又は炭素数１～５のアルキル基を表す。
Ｍ^ｘ＋は、ヒドロン又はｘ価の金属カチオンを表す。
ｘは２以上の整数を表す。
ａは、ａが付く括弧内の構造の価数を表し、１以上１２以下の整数を表す。
ｂは、Ｍ^Ｘ＋の個数を表し、１以上１２以下の整数を表す。
ａ及びｂは、下記式：
ａ＝ｂｘ
を満たす。］
［２］ ［１］に記載の着色組成物と、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。
［３］ ［２］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。
［４］ ［３］に記載のカラーフィルタを含む表示装置。 The present invention provides the following [1] to [4].
[1] A colored composition containing a compound represented by the following formula (I) and a resin.

[In the formula,
R ¹ to R ³ each independently represent a hydrogen atom, —CO ₂ ⁻ , a halogen atom, a cyano group, a nitro group, or an optionally substituted hydrocarbon group having 1 to 40 carbon atoms.
R ⁴ to R ¹¹ each independently represent an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, cyano group, nitro group, —CO ₂ ⁻ , or —S(O) ₂ O ^— .
—CH ² — which is included in the optionally substituted hydrocarbon group having 1 to 40 carbon atoms and does not form a ring, represented by R 4 to R ¹¹ _, and R ⁴ to R ¹¹ —CH ₂ — contained in the represented heterocyclic group optionally having substituent(s) and not forming a ring, —O—, —CO—, —S(O) ₂ —, —NR ^x1 — may be replaced by 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.
M ^x+ represents a hydrogen or an x-valent metal cation.
x represents an integer of 2 or more.
a represents the valence of the structure in parentheses with a and represents an integer of 1 or more and 12 or less.
b represents the number of M ^X+ and represents an integer of 1 or more and 12 or less.
a and b are represented by the following formula:
a=bx
meet. ]
[2] A colored curable resin composition comprising the colored composition according to [1], a polymerizable compound, a polymerization initiator, and a solvent.
[3] A color filter formed from the colored curable resin composition according to [2].
[4] A display device including the color filter described in [3].

ADVANTAGE OF THE INVENTION According to this invention, the coloring composition which has favorable heat resistance and light resistance is provided.

<Coloring composition>
The coloring composition of the present invention contains a compound represented by formula (I) (hereinafter also referred to as compound (I)) and a resin (hereinafter also referred to as resin (B)).

Compound (I) also includes tautomers and salts thereof.
Compound (I) can be used as a coloring agent.
The coloring composition of the present invention may contain one or more compounds (I).
The coloring composition of the present invention may contain a solvent (hereinafter sometimes referred to as solvent (E)).
Moreover, it is preferable that the compound (I) is dispersed in the solvent (E).
The coloring composition of the present invention may contain a coloring agent other than the compound (I) (hereinafter also referred to as a coloring agent (A1)) (hereinafter, a combination of the compound (I) and the coloring agent (A1) Also referred to as a coloring agent (A)).
The colorant (A1) may contain one or more colorants.
Colorant (A1) preferably comprises a yellow colorant and/or an orange colorant and/or a red colorant.
Further, the colored curable resin composition of the present invention includes a compound (I), a resin (B), a polymerizable compound (hereinafter also referred to as a polymerizable compound (C)), a polymerization initiator (hereinafter, polymerization initiator (D )) and the solvent (E). In other words, the colored curable resin composition of the present invention contains the colored composition of the present invention, a polymerizable compound (C), a polymerization initiator (D) and a solvent (E).
The colored curable resin composition of the present invention may contain a polymerization initiation aid (hereinafter also referred to as polymerization initiation aid (D1)).
The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter also referred to as a leveling agent (F)) and an antioxidant.

［式中、
Ｒ^１～Ｒ^３は、互いに独立に、水素原子、－ＣＯ_２ ^－、ハロゲン原子、シアノ基、ニトロ基、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。
Ｒ^４～Ｒ^１１は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基、ニトロ基、－ＣＯ_２ ^－、又は－Ｓ（Ｏ）_２Ｏ^－を表す。
前記Ｒ^４～Ｒ^１１で表される置換基を有していてもよい炭素数１～４０の炭化水素基に含まれ、かつ環を構成しない－ＣＨ_２－、及び前記Ｒ^４～Ｒ^１１で表される置換基を有していてもよい複素環基に含まれ、かつ環を構成しない－ＣＨ_２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）_２－、－ＮＲ^ｘ１－に置き換わっていてもよい。ただし、前記－ＣＨ_２－が置き換わることで－ＣＯＯＨ及び－Ｓ（Ｏ）_２ＯＨが形成されることはない。
前記Ｒ^ｘ１は、水素原子、又は炭素数１～５のアルキル基を表す。
前記Ｒ^４～Ｒ^１１で表される置換基を有していてもよい炭素数１～４０の炭化水素基及び置換基を有していてもよい複素環基は、－ＣＯ_２ ^－及び－Ｓ（Ｏ）_２Ｏ^－からなる群から選ばれる少なくとも一種を有していてもよい。
Ｍ^ｘ＋は、ヒドロン又はｘ価の金属カチオンを表す。
ｘは２以上の整数を表す。
ａは、ａが付く括弧内の構造の価数を表し、１以上１２以下の整数を表す。
ｂは、Ｍ^Ｘ＋の個数を表し、１以上１２以下の整数を表す。
ａ及びｂは、下記式：
ａ＝ｂｘ
を満たす。］ [Compound (I)]
Compound (I) is a compound represented by the following formula (I).

[In the formula,
R ¹ to R ³ each independently represent a hydrogen atom, —CO ₂ ⁻ , a halogen atom, a cyano group, a nitro group, or an optionally substituted hydrocarbon group having 1 to 40 carbon atoms.
R ⁴ to R ¹¹ each independently represent an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, cyano group, nitro group, —CO ₂ ⁻ , or —S(O) ₂ O ^— .
—CH ² — which is included in the optionally substituted hydrocarbon group having 1 to 40 carbon atoms and does not form a ring, represented by R 4 to R ¹¹ _, and R ⁴ to R ¹¹ —CH ₂ — contained in the represented heterocyclic group optionally having substituent(s) and not forming a ring, —O—, —CO—, —S(O) ₂ —, —NR ^x1 — may be replaced by 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.
The optionally substituted C 1-40 hydrocarbon group and optionally substituted heterocyclic group represented by R ⁴ to R ¹¹ are —CO ₂ ^— and —S It may have at least one selected from the group consisting of (O) ₂ ^O- .
M ^x+ represents a hydrogen or an x-valent metal cation.
x represents an integer of 2 or more.
a represents the valence of the structure in parentheses with a and represents an integer of 1 or more and 12 or less.
b represents the number of M ^X+ and represents an integer of 1 or more and 12 or less.
a and b are represented by the following formula:
a=bx
meet. ]

Halogen atoms represented by R ¹ to R ³ include fluorine, chlorine, bromine and iodine atoms. Among them, a fluorine atom and a chlorine atom are preferred.

The number of carbon atoms in the hydrocarbon group represented by R ¹ to R ³ is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, especially It is preferably 1-10.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ to R ³ represents an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated. It may be linear or cyclic (alicyclic hydrocarbon group).

Saturated or unsaturated chain aliphatic hydrocarbon groups represented by R ¹ to R ³ 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 , a heptacosyl group, an octacosyl group, a nonacosyl group, a triacontyl group, a hentriacontyl group, a dotriacontyl group, a tritriacontyl group, a tetratriacontyl group, a pentatriacontyl group, a hexatriacontyl group, a heptatriacontyl group, Linear alkyl groups such as octatriacontyl group, nonatriacontyl group, tetracontyl group, etc.; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group group, tert-pentyl group, (1-methyl)pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, isohexyl group, (5-methyl)hexyl group, Branched chain alkyl groups such as (2-ethyl)hexyl group and (3-ethyl)heptyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group , 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 saturated or unsaturated chain hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, still more preferably 1 to 15 carbon atoms, and particularly preferably 1 to 10 carbon atoms. Among them, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferable, and a methyl group or an ethyl group is particularly preferable.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ¹ to R ³ include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and 1-methylcyclohexyl. group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl 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 a tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; cycloalkenyl groups such as cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane and the like. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, and particularly preferably 4 to 15 carbon atoms, More preferably 5-15, particularly preferably 5-10. Among them, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group are most preferable.

Aromatic hydrocarbon groups represented by R ¹ to R ³ include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethyl phenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group , 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3 , 5-di(tert-butyl)phenyl group, mesityl group, 4-ethylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 5,6, 7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecyl aromatic hydrocarbon groups such as phenyl group and pyrenyl group; 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 ¹ to R ³ are groups in which two or more of the above-mentioned hydrocarbon groups are combined, such as at least aromatic hydrocarbon groups, chain hydrocarbon groups and alicyclic hydrocarbon groups. aralkyl groups such as benzyl group, phenethyl group, 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 such as biphenylyl groups and terphenylyl groups are bonded; cyclohexylmethylphenyl groups, benzylphenyl groups, (dimethyl(phenyl)methyl)phenyl groups, and the like. .

The hydrocarbon group represented by R ¹ to R ³ may be a group in which two or more of the above-mentioned hydrocarbon groups are combined, for example, a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined. , examples thereof include cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, adamantylmethyl and an alkyl group to which one or more alicyclic hydrocarbon groups such as groups are bonded.

The number of carbon atoms in the group obtained by combining two or more of the above hydrocarbon groups is preferably 4-30, more preferably 4-20, even more preferably 4-15, still more preferably 6-15.

Examples of substituents that the hydrocarbon groups having 1 to 40 carbon atoms represented by R ¹ to R ³ may have include halogen atoms, formyl groups, carboxy groups, formyloxy groups, hydroxy groups, and thiols. 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 and the like mentioned.

Halogen atoms include fluorine, chlorine, bromine and iodine atoms. Among them, a fluorine atom and a chlorine atom are preferred.

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

The alkyl groups represented by R ¹² and R ¹³ preferably have 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 5 carbon atoms.

Examples of alkyl groups 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 and tridecyl group. , tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group and icosyl group.

—COR ¹² includes, for example, an acetyl group, a propanoyl group, a butanoyl group, a 2,2-dimethylpropanoyl group, a pentanoyl group, a hexanoyl group, a (2-ethyl)hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group and a decanoyl group. , undecanoyl group, dodecanoyl group, henicosanoyl group, benzoyl group and the like.

—COOR ¹² includes, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl)hexyloxycarbonyl, heptyl oxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group and icosyloxycarbonyl group.

—OCOR ¹² includes, for example, an acetoxy group, a propanoyloxy group, a butanoyloxy group, a 2,2-dimethylpropanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a (2-ethyl)hexanoyloxy group, heptanoyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, 2-propenylcarbonyl An oxy group and the like can be mentioned.

—OR ¹² includes, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a phenoxy group, a naphthyloxy group and the like.

—SR ¹² includes, for example, a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, a tert-butylsulfanyl group, a pentylsulfanyl group, a hexylsulfanyl group, a (2-ethyl)hexylsulfanyl group, a heptylsulfanyl group, octylsulfanyl group, nonylsulfanyl group, decylsulfanyl group, undecylsulfanyl group, dodecylsulfanyl group, icosylsulfanyl group, phenylsulfanyl group, o-tolylsulfanyl group and the like.

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

—SO ₂ R ¹² includes, for example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, phenylsulfonyl group, naphthylsulfonyl group and the like.

—SO ₂ NHR ¹² includes, for example, 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 famoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N -undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamoyl group, N-phenylsulfamoyl group and the like.

—SO ₂ NR ¹² R ¹³ includes, for example, N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group; moyl 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 famoyl group, N,N-dipentylsulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group famoyl group, N,N-diheptylsulfamoyl group, N,N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N- Decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group moyl group, N,N-diphenylsulfamoyl group and the like.

—CONHR ¹² includes, for example, an N-methylcarbamoyl group, an N-ethylcarbamoyl group, an N-propylcarbamoyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, and an N-sec-butylcarbamoyl group. , N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N -octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamoyl group, N-phenylcarbamoyl group and the like.

—CONR ¹² R ¹³ includes an N,N-dimethylcarbamoyl group, an N,N-ethylmethylcarbamoyl group, an N,N-diethylcarbamoyl group, an N,N-propylmethylcarbamoyl group and an 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, for example, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group and N-sec-butylamino group. , N-tert-butylamino group, N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N -decylamino group, N-undecylamino group, N-dodecylamino group, N-icosylamino group, N-phenylamino group and the like.

—NR ¹² R ¹³ includes, for example, 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-decylmethyl amino group, N,N-undecylmethylamino group, N,N-dodecylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc. mentioned.

—NHCOR ¹² includes, for example, an acetylamino group, a propanoylamino group, a butanoylamino group, a 2,2-dimethylpropanoylamino group, a pentanoylamino group, a hexanoylamino group, and a (2-ethyl)hexanoylamino group. , heptanoylamino group, octanoylamino group, nonanoylamino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group and the like.
—NR ¹³ COR ¹² includes, for example, an N-methyl-N-acetylamino group.
R ¹ to R ³ preferably each independently represent —CO ₂ ⁻ , a halogen atom, a cyano group, a nitro group, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and R ¹ At least one of ~R ³ represents -CO ₂ ^- .
R ¹ to R ³ more preferably independently represent -CO ₂ ^- , a halogen atom, a cyano group or a nitro group, and at least one of R ¹ to R ³ represents -CO ₂ ^- .
R ¹ to R ³ more preferably independently of each other R ¹ and R ³ are identically —CO ₂ ^— , a halogen atom, a cyano group or a nitro group, and R ² is —CO ₂ ^— .

Halogen atoms represented by R ⁴ to R ¹¹ include fluorine, chlorine, bromine and iodine atoms. Among them, a fluorine atom and a chlorine atom are preferred.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ⁴ to R ¹¹ represents an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated. may be linear or cyclic.

Saturated or unsaturated chain aliphatic hydrocarbon groups represented by R ⁴ to R ¹¹ 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 , a heptacosyl group, an octacosyl group, a nonacosyl group, a triacontyl group, a hentriacontyl group, a dotriacontyl group, a tritriacontyl group, a tetratriacontyl group, a pentatriacontyl group, a hexatriacontyl group, a heptatriacontyl group, Linear alkyl groups such as octatriacontyl group, nonatriacontyl group, tetracontyl group, etc.; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group group, tert-pentyl group, (1-methyl)pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, isohexyl group, (5-methyl)hexyl group, Branched chain alkyl groups such as (2-ethyl)hexyl group and (3-ethyl)heptyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group , 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 saturated or unsaturated chain hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, still more preferably 1 to 15 carbon atoms, and particularly preferably 1 to 10 carbon atoms. Among them, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferable, and a methyl group or an ethyl group is particularly preferable.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ⁴ to R ¹¹ include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and 1-methylcyclohexyl. group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl 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 a tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; cycloalkenyl groups such as cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane and the like. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, and particularly preferably 4 to 15 carbon atoms, More preferably 5-15, particularly preferably 5-10. Among them, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group are most preferable.

Aromatic hydrocarbon groups represented by R ⁴ to R ¹¹ include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethyl phenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group , 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3 , 5-di(tert-butyl)phenyl group, mesityl group, 4-ethylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 5,6, 7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecyl aromatic hydrocarbon groups such as phenyl group and pyrenyl group; 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 ⁴ to R ¹¹ are groups in which two or more of the above-mentioned hydrocarbon groups are combined, such as at least aromatic hydrocarbon groups, chain hydrocarbon groups and alicyclic hydrocarbon groups. aralkyl groups such as benzyl group, phenethyl group, 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 such as biphenylyl groups and terphenylyl groups are bonded; cyclohexylmethylphenyl groups, benzylphenyl groups, (dimethyl(phenyl)methyl)phenyl groups, and the like. .

The hydrocarbon group represented by R ⁴ to R ¹¹ may be a group in which two or more of the above-mentioned hydrocarbon groups are combined, for example, a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined. , examples thereof include cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, adamantylmethyl and an alkyl group to which one or more alicyclic hydrocarbon groups such as groups are bonded.

The number of carbon atoms in the group obtained by combining two or more of the above hydrocarbon groups is preferably 4-30, more preferably 4-20, even more preferably 4-15, still more preferably 6-15.

The heterocyclic groups represented by R ⁴ to R ¹¹ may be monocyclic or polycyclic. Heteroatoms in the heterocyclic group include, for example, nitrogen, oxygen and sulfur atoms.

The heterocyclic group represented by R ⁴ to R ¹¹ preferably has 1 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, still more preferably 3 to 16 carbon atoms, and particularly preferably 3 to 14 carbon atoms. Yes, more preferably 3-12.

Heterocyclic rings in heterocyclic groups containing nitrogen atoms include monocyclic saturated heterocyclic rings such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrrole, pyrazole, imidazole, 1,2,3-triazole and 1,2,4 - 5-membered unsaturated heterocycles such as triazole; 6-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine and 1,3,5-triazine; indazole, indoline, isoindoline, indole, indolizine , benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydroquinoxaline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine and other condensed bicyclic heterocycles; carbazole, acridine and condensed tricyclic heterocycles such as phenazine;

The heterocyclic ring in the heterocyclic group containing an oxygen atom includes monocyclic saturated heterocyclic rings such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1,3-dioxolane; Bicyclic saturated heterocycles such as 4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.4]nonane; α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and Lactone heterocycles such as δ-valerolactone; 5-membered unsaturated heterocycles such as furan; 6-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; 1-benzofuran, benzopyran, benzodiox condensed bicyclic heterocycles such as sol, chroman and isochroman; condensed tricyclic heterocycles such as xanthene and dibenzofuran; and the like.

The heterocyclic ring in the heterocyclic group containing a sulfur atom includes a 5-membered saturated heterocyclic ring such as dithiolane; a 6-membered saturated heterocyclic ring such as thiane and 1,3-dithiane; thiophene, 4H-thiopyran, benzotetrahydrothio 5-membered ring system unsaturated heterocycles such as pyran; condensed bicyclic heterocycles such as benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene;

The heterocyclic ring in the heterocyclic group containing a nitrogen atom and an oxygen atom includes monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone and 2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; benzoxazole; , benzoisoxazole, benzoxazine, benzodioxane, benzimidazoline and the like; condensed bicyclic heterocycles such as phenoxazine; and the like.

The heterocycle in the heterocyclic group containing a nitrogen atom and a sulfur atom includes monocyclic heterocycles such as thiazole; condensed bicyclic heterocycles such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; .

In addition, the bonding position of the heterocyclic group is a portion from which any hydrogen atom contained in each heterocyclic ring is eliminated.

The heterocyclic group may be a group in which two or more of the heterocyclic groups exemplified above and the hydrocarbon groups exemplified above are combined, and examples thereof include a tetrahydrofurylmethyl group and the like.

Examples of substituents which the hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ⁴ to R ¹¹ may have include a halogen atom, formyl group, formyloxy group, hydroxy group, carboxy group, thiol 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 and the like. Examples of R ¹² and R ¹³ are the same as the alkyl group, phenyl group or naphthyl group exemplified above.

Examples of substituents which the hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ⁴ to R ¹¹ may have include 1 carbon atom represented by R ¹ to R ³ described above. The examples are the same as in the description of the substituents which the hydrocarbon groups of 1 to 40 may have.

—CH ₂ — included in hydrocarbon groups having 1 to 40 carbon atoms represented by R ⁴ to R ¹¹ and not forming a ring, and included in heterocyclic groups represented by R ⁴ to R ¹¹ , and —CH ₂ that does not constitute a ring may be replaced with —O—, —CO—, —S(O) ₂ —, —NR ^x1 —. However, -CH ₂ - is not replaced to form -COOH and -S(O) ₂ OH. R ^x1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of alkyl groups 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 ⁴ to R ¹¹ include groups represented by the following formulas. * represents a bond.

R ⁴ to R ¹¹ are preferably hydrogen atom, halogen atom, hydroxy group, nitro group, cyano group, —CH ₃ , formulas (Aa-1) to (Aa-18), (Ba-1) to (Ba -27), (Ca-1) to (Ca-18) and (Da-1) to (Da-27).

M ^x+ represents a hydrogen or an x-valent metal cation. x represents an integer of 2 or more, preferably an integer of 2 or more and 4 or less.

Examples of divalent metal cations (M ²⁺ ) include Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Cd ²⁺ , Fe ²⁺ , Co 2+ , Rh ²⁺ , Ir ²⁺ , Ni ²⁺ , Pd ²⁺ , Cu ^{2+ ,} Zn ²⁺ , Hg ²⁺ , Sn ²⁺ , Pb ²⁺ , Mn ²⁺ and the like.

Examples of trivalent metal cations (M ³⁺ ) include Cr ³⁺ , Fe ³⁺ , Co ³⁺ and Al ³⁺ .

Examples of tetravalent metal cations (M ⁴⁺ ) include Ti ⁴⁺ , Zr ⁴⁺ , Hf ⁴⁺ , Mn ⁴⁺ , Si ⁴⁺ , Ge ⁴⁺ , Sn ⁴⁺ and Pb ⁴⁺ .

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

Among them, compounds represented by the following formulas (I-1) to (I-5) are preferred.

Compounds represented by formulas (I-1), (I-2), (I-3) and (I-5) are more preferred from the viewpoint of heat resistance and light resistance.

Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) with water. Alternatively, compound (I) is produced, for example, by reacting a product obtained by reacting a compound represented by the following formula (pt1) with water and a compound represented by the following formula (M1). be able to.

［式中、Ｒ^４～Ｒ^１１は、上述の定義と同一である。］

[In the formula, R ⁴ to R ¹¹ are the same as defined above. ]

Examples of the compound represented by the formula (pt1) include 3,4,9,10-perylenetetracarboxylic dianhydride and the like. The amount of water used is generally 2 mol or more and 20 mol or less, preferably 2 mol or more and 16 mol or less, more preferably 2 mol or more and 10 mol or less, per 1 mol of the compound represented by the formula (pt1). or less, more preferably 2 mol or more and 8 mol or less.

The reaction between the compound represented by formula (pt1) below and water is usually carried out in the presence of a base and a solvent. Examples of bases include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3 .0]non-5-ene, organic bases such as 1,5-diazabicyclo[4.3.0]non-5-ene, organometallic compounds such as methyllithium, butyllithium, tert-butyllithium and phenyllithium; Inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide are included.

The amount of the base to be used is generally 1 mol or more and 20 mol or less, preferably 1 mol or more and 16 mol or less, more preferably 1 mol or more and 10 mol or less, per 1 mol of the compound represented by the formula (pt1). or less, more preferably 1 mol or more and 8 mol or less.

When a compound represented by the following formula (pt1) is reacted with water in the presence of a base, the compound (I) of the present invention can be produced by neutralizing with an acid at the end of the reaction. . Acids include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and Carboxylic acid etc. are mentioned.

The amount of the acid to be used is generally 1 mol or more and 20 mol or less, preferably 1 mol or more and 16 mol or less, more preferably 1 mol or more and 10 mol or less, per 1 mol of the compound represented by the formula (pt1). or less, more preferably 1 mol or more and 8 mol or less.

［式中、
Ｍは、ヒドロン又はｘ価の金属カチオンを表す。
ｘは２以上の整数を表す。
ｐは１以上の整数を表す。］

[In the formula,
M represents hydrogen or an x-valent metal cation.
x represents an integer of 2 or more.
p represents an integer of 1 or more. ]

Examples of the compound represented by formula (M1) include magnesium acetate and barium acetate.

The amount of the compound represented by formula (M1) to be used is generally 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 mol or less, and still more preferably 1 mol or more and 4 mol or less.

Examples of solvents 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; 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 dimethylsulfoxide.

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

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

Compound (I) in which R ¹ , R ³ and R ⁴ to R ¹¹ are hydrogen atoms and R ² is —CO ₂ ^— is diisobutyl 3,9-perylenedicarboxylate (Solvent It can be produced by reacting Green 5) with a base in the presence of a solvent, and then reacting the resulting product with an acid or a compound represented by formula (M1).

Compound (I) in which R ¹ and R ³ are cyano groups, R ² is —CO ₂ ^— , and R ⁴ to R ¹¹ are hydrogen atoms is 4,10-dicyano It can be produced by reacting diisobutyl perylene-3,9-dicarboxylate with a base in the presence of a solvent, and then reacting the resulting product with an acid or a compound represented by formula (M1). .

The base, solvent, acid, compound represented by formula (M1), and the amounts used thereof may be the same as those exemplified above. The reaction temperature may be in the temperature ranges exemplified above.

After completion of the reaction, the method for removing compound (I) is not particularly limited, and can be obtained by various known methods. Compound (I) can be isolated, for example, by evaporating the solvent. Furthermore, after distilling off the solvent, the resulting residue may be purified by column chromatography, recrystallization, or the like. Also, after the reaction is completed, the compound (I) can be taken out by filtration. After filtration, the resulting residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the obtained compound (I) can be analyzed by a known analytical technique and its conditions. Examples of such analysis techniques include, but are not limited to, X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystal structure analysis is described, for example, in Chemistry of Materials, 2012, Vol. 24, p. 4647-4652.

The content of compound (I) in the coloring composition may be, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 0.5, relative to the total amount of solids in the coloring composition. 99% by mass or less, more preferably 1% by mass or more and 95% by mass or less, still more preferably 5% by mass or more and 90% by mass or less, and particularly preferably 10% by mass or more and 80% by mass or less more preferably 15% by mass or more and 70% by mass or less, still more preferably 20% by mass or more and 60% by mass or less, particularly preferably 25% by mass or more and 55% by mass or less, and extremely preferably 30% by mass % or more and 50% by mass.
As used herein, the term "total amount of solids in the coloring composition" refers to the total amount of components in the coloring composition excluding all solvent components. The total amount of solids and the content of each component relative thereto can be measured by known analysis means such as liquid chromatography or gas chromatography.

[Colorant (A1)]
The coloring composition can contain a coloring agent (A1) as a coloring agent other than compound (I).

The colorant (A1) may contain one or more colorants. The coloring agent (A1) preferably contains a yellow coloring agent and/or an orange coloring agent and/or a red coloring agent.

Colorant (A1) may be either a dye or a pigment. As the dye, known dyes can be used, and examples thereof include known dyes described in Color Index (published by The Society of Dyers and Colorists) and Dye Note (Shikisensha). Further, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, perylene dyes and the like can be mentioned. These dyes may be used alone or in combination of two or more.

Dyes with Color Index (C.I.) numbers such as:
Specific examples include dyes with the following Color Index (C.I.) numbers.
C. I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
C. I. Solvent Red 24, 45, 49, 90, 91111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
C. I. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. solvent blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. C.I. I. solvent dyes,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. acid red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C. I. acid blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;
C. I. acid green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109 and the like. 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. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and the like. I. direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C.I. I. disperse dyes,
C. I. Basic Red 1, 10;
C. I. basic blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C. I. basic violet 2;
C. I. basic red 9;
C. I. Basic Green 1; I. basic dye,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. C.I. Reactive Red 36; I. reactive dyes,
C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern 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. Modant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Modant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. C.I. I. modant dye,
C. I. C.I. I. Vat dyes, etc.

The following dyes may be mentioned.
BASF product names: Lumogen® Lumogen F Yellow 083, Lumogen® F Yellow 170, Lumogen® F Orange 240 and Lumogen® F Red 305.

As the pigment, known pigments can be used, and examples thereof include 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. 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;
C. I. Brown pigments such as Pigment Brown 23 and 25;
C. I. Black pigments such as Pigment Black 1, 7, 31, and 32 are included.

Examples of the coloring agent (A1) include yellow dyes and yellow pigments (hereinafter collectively referred to as "yellow coloring agents"), green dyes and green pigments (hereinafter collectively referred to as "green coloring agents"). is preferred, yellow pigments and green pigments are more preferred, and green pigments are even more preferred.
Examples of yellow dyes include dyes classified as yellow in hue among the above dyes, and examples of yellow pigments include pigments classified as yellow in hue among the above pigments.
Among yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments and isoindoline yellow pigments are preferred, and C.I. I. Pigment Yellow 129, 138, 139, 150, 185 and 231 are more preferred, and C.I. I. Pigment Yellow 138, 139, 150, 185 and 231 are more preferred.
Examples of green dyes include dyes classified as green in hue among the above dyes, and examples of green pigments include pigments classified as green in hue among the above pigments.
Among green pigments, phthalocyanine pigments are preferred, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferred. I. At least one selected from the group consisting of Pigment Green 7, 36, 58 and 59 is more preferred.

The coloring agent (A1) is preferably a coloring agent containing one or more selected from green coloring agents and yellow coloring agents.

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

When the coloring composition contains the coloring agent (A1), the upper limit of the content of the compound (I) in the coloring agent (A) is usually 1% by mass or more with respect to the total amount of the coloring agent (A), It is 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 content of compound (I) in colorant (A) is usually 100% by mass or less with respect to the total amount of colorant (A).

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

When the coloring composition contains the solvent (E), a coloring agent-containing liquid containing the compound (I) or the coloring agent (A) and the solvent (E) is prepared in advance, and then the coloring agent-containing liquid is used. A coloring composition may be prepared. When compound (I) or colorant (A) does not dissolve in solvent (E), the colorant-containing liquid is prepared by dispersing compound (I) or colorant (A) in solvent (E) and mixing. can. 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, relative to the total amount of the colorant-containing liquid. % by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 90% by mass or less, still more preferably 1% by mass or more and 60% or less, and still more preferably 3 It is 50% by mass or more, particularly preferably 3% by mass or more and 30% by mass or less, and most preferably 5% by mass or more and 30% by mass or less.

The content of compound (I) or colorant (A) in the colorant-containing liquid is usually 100% by mass or less, preferably 0.0001% by mass or more, and 99% by mass of the total solid content in the colorant-containing liquid. .9999% by mass or less, more preferably 0.01% by mass or more and 99% by mass or less, still more preferably 1% by mass or more and 99% by mass or less, and particularly preferably 10% by mass or more and 99% by mass or less more preferably 20% by mass or more and 99% by mass or less.
As used herein, "the total amount of solids in the colorant-containing liquid" refers to the total amount of the components of the colorant-containing liquid excluding the solvent (E). The total amount of solids and the content of each component relative thereto can be measured by known analysis means such as liquid chromatography or gas chromatography.

The colorant (A1) can be uniformly dispersed in the liquid containing the colorant (A1) by incorporating a dispersant and performing a dispersion treatment. The colorants (A1) may be dispersed individually, or may be mixed and dispersed.

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

When a dispersant is used to prepare the colorant-containing liquid, the amount of the dispersant (solid content) used is usually 10000 parts by mass or less per 100 parts by mass of compound (I) or colorant (A). , preferably 5000 parts by mass or less, 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, and still more preferably 100 parts by mass or less , more preferably 5 to 100 parts by mass, and particularly preferably 5 to 50 parts by mass. When the amount of the dispersant used is within the above range, there is a tendency to obtain a colorant-containing liquid in a more uniformly dispersed state.

[Resin (B)]
The resin (B) is preferably an alkali-soluble resin and contains at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as "monomer (a)" It is more preferable that the polymer has a structural unit derived from
Resin (B) is a structural unit derived from a monomer having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b)"), and other is preferably a copolymer having a structural unit of
As other structural units, a monomer copolymerizable with the monomer (a) (which is different from the monomer (a) and the monomer (b), hereinafter "monomer (c)") may be called), structural units having an ethylenically unsaturated bond, and the like.

Examples of 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-vinyl phthalic acid, 4-vinyl phthalic 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 the anhydrides of the above unsaturated dicarboxylic acids except fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate kind;
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 preferable from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say. 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, (hereinafter sometimes referred to as "monomer (b2)") and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b3)" ) and the like.

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

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred.
Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, α- methyl vinyl benzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxy methyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4, 5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene.
Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), and 3,4-epoxycyclohexylmethyl. (Meth)acrylate (eg, Cychromer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cychromer (registered trademark) M100; manufactured by Daicel Corporation) , a compound represented by the formula (BI), a compound represented by the 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 substituted 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 alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.

Alkyl groups in which a hydrogen atom is substituted with hydroxy include, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1 -hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.

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

Examples of 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, A hexane-1,6-diyl group and the like can be mentioned.

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

Examples of the compound represented by formula (BI) include compounds represented by any one 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 preferable.

Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), and among them, preferably formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and compounds represented by 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 the formula (BI) and the compound represented by the formula (BII) may be used alone, or the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. You may When these are used in combination, 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: on a molar basis. 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 preferred.
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. are 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), the monomer (b1) is preferable in that the heat resistance, chemical resistance, etc. of the obtained color filter can be further improved. Furthermore, the monomer (b1-2) is more preferable in terms of excellent storage stability of the coloring composition.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2. 1.0 ^2,6 ]decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^{2 ,6} ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate ) (meth)acrylic acid esters such as acrylates, 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 oxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclounsaturated compounds;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 - dicarbonylimide derivatives such as maleimidopropionate and N-(9-acridinyl)maleimide;
vinyl group-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth)acrylamide esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene;
Among these, styrene, vinyl toluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate, tricyclo[5.2.1 .0 ^2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^{2, 6} ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and benzyl(meth)acrylate are preferred.

A 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 the monomer (a) or the monomer (b), and a group having the monomer (a) or the monomer (b). can be obtained by adding a monomer having an ethylenically unsaturated bond to a group capable of reacting with.
Examples of such structural units include structural units obtained by adding glycidyl (meth)acrylate to (meth)acrylic acid units, structural units obtained by adding 2-hydroxyethyl (meth)acrylate to maleic anhydride units, and glycidyl (meth)acrylate units. ) structural units obtained by adding (meth)acrylic acid to acrylate units, and the like. Moreover, when these structural units have a hydroxy group, a structural unit to which a carboxylic acid anhydride is further added is also included as a structural unit having an ethylenically unsaturated bond.

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

The obtained polymer may be used as it is after the reaction, or may be used as a concentrated or diluted solution, or taken out as a solid (powder) by a method such as reprecipitation. may be used.
If necessary, a reaction catalyst (eg, tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (eg, hydroquinone, etc.) for the reaction between carboxylic acid or carboxylic acid anhydride and cyclic ether may be used.
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.

Specific examples of the resin (B) include 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/vinyl toluene 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 Copolymer, benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer and JP-A-9-106071, JP-A-2004-29518 and JP-A-2004- Examples thereof include resins described in each gazette of JP-A-361455.
Among them, 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.

The resin (B) may be a combination of two or more, in which case the resin (B) is at least 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate /(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (Meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxy It preferably contains one or more selected from tricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/2-ethylhexyl(meth)acrylate copolymer.

The polystyrene equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 or more and 100,000 or less, more preferably 1,000 or more and 50,000 or less, and still more preferably 1,000 or more. It is 30,000 or less, and particularly preferably 3000 or more and 30000 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. 01 or more and 4 or less.

The acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, and still more preferably 20 mg. -KOH/g or more and 200 mg-KOH/g or less, particularly preferably 20 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 30 mg-KOH/g or more and 170 mg-KOH/g or less, particularly preferably 60 mg-KOH/g /g or more and 150 mg-KOH/g or less, extremely preferably 70 mg-KOH/g or more and 140 mg-KOH/g or less, extremely preferably 70 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 by titration with an aqueous potassium hydroxide solution, for example.

The content of the resin (B) in the coloring composition may be, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 0.5, relative to the total amount of solids in the coloring composition. 99% by mass or less, more preferably 1% by mass or more and 95% by mass or less, still 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, and still more preferably is 5% by mass or more and 70% by mass or less, 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 15% by mass or more and 40% by mass or less. % or less.

When the coloring composition of the present invention is prepared by using the coloring agent-containing liquid after preparing the coloring agent-containing liquid in advance, the coloring agent-containing liquid contains the resin (B) described later contained in the coloring composition. Part or all, preferably part may be included in advance. By containing the resin (B) in advance, the dispersion stability of the colorant-containing liquid can be further improved.

The content of the resin (B) in the colorant-containing liquid may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, relative to 100 parts by mass of the compound (I) or the colorant (A). , More preferably 1000 parts by mass or less, 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, still more preferably 10 parts by mass or more and 100 parts by mass or less is.

<Colored curable resin composition>
The colored curable resin composition contains a colored composition, a polymerizable compound (C), a polymerization initiator (D) and a solvent (E).

The content of solids in the colored composition contained in the colored curable resin composition is appropriately adjusted according to the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured. Although it is not particularly limited, it may be, for example, 1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 90% by mass or less, and more preferably, based on the total amount of solid content 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, and still more preferably 5% by mass or more and 50% by mass. or less, particularly preferably 6% by mass or more and 40% by mass or less, and extremely preferably 7% by mass or more and 30% by mass or less.

The content of compound (I) in the colored curable resin composition is not particularly limited because it is appropriately adjusted according to the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured. , the total amount of solids in the colored curable resin composition may be, for example, 0.1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 90% by mass or less, more preferably 2% by mass. 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, still more preferably 5% by mass or more and 50% by mass or less, Particularly preferably, it is 6% by mass or more and 40% by mass or less, and extremely preferably 7% by mass or more and 30% by mass or less.

As used herein, "the total amount of solids in the colored curable resin composition" refers to the total amount of components excluding the solvent (E) from the colored curable resin composition. The total amount of solids and the content of each component relative thereto can be measured by known analysis means such as liquid chromatography or gas chromatography. The content of solids in the colored curable resin composition may be, for example, 0.01% by mass or more and 100% by mass or less, preferably 0.1% by mass, relative to 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, still more preferably 1% by mass or more and 90% by mass or less, particularly preferably 1% by mass or more and 60% or less, It is preferably 3% by mass or more and 50% by mass or less, more preferably 3% by mass or more and 30% by mass or less, and particularly preferably 5% by mass or more and 30% by mass or less.

The colored pattern and colored coating film described later, which are formed from the colored curable resin composition, may have an absorption maximum (λmax) in a wavelength range of, for example, 420 nm or more and 510 nm or less, preferably in a wavelength range of 440 nm or more and 500 nm or less. It has an absorption maximum (λmax).
Absorption maximum (λmax) and absorbance can be measured, for example, using a colorimeter (OSP-SP-200; manufactured by OLYMPUS).

[Polymerizable compound (C)]
The polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, etc., preferably 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., as well as monomers (a), (b) and (c) described above.

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

Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 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 4000 or less, more preferably 50 or more and 3500 or less, still more preferably 50 or more and 3000 or less, and particularly preferably 150 or more and 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, relative to the total amount of solids in the colored curable resin composition. or less, more preferably 3% by mass or more and 80% by mass or less, still more 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 still more preferably 6 It is 50% by mass or more and preferably 7% by mass or more and 40% by mass or less.

[Polymerization initiator (D)]
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat, and known polymerization initiators 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]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl -2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3- cyclopentylpropan-1-one-2-imine and the like. As the O-acyl oxime compound, commercially available products such as Irgacure OXE01 and OXE02 (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 Oxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferred.

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

Biimidazole compounds include, for example, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2,3-dichlorophenyl)-4 ,4′,5,5′-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2′-bis(2-chlorophenyl)-4, 4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2 '-Bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403, JP-A-62-174204, etc.) and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

Triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis( trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methyl phenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, etc. .

Acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) may also be used.

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

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

The content of the polymerization initiator (D) is, for example, 0.01% by mass or more and 40% by mass with respect to the total amount of the total resin (B) and the polymerizable compound (C) contained in the colored curable resin composition. or less, preferably 0.1% by mass or more and 30% by mass or less.

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

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

Alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy and anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxythioxanthone.

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 is, for example, 0.01% by mass or more and 40% by mass or less with respect to the total amount of the resin (B) and the polymerizable compound (C). Well, preferably 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- in the molecule but not containing -COO-), an ether Ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not containing -COO-), alcohol solvents (containing OH in the molecule, -O-, -CO- and -COO--free solvents), 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, and propylene glycol monoethyl ether. , propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, methylanisole and the like.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 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 Ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate and the like.

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.

Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
Aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene and the like.
Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

These solvents may be used in combination of two or more.

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 99.9% by mass or less, relative to the total amount of the colored curable resin composition. is 1% by mass or more and 99.9% by mass or less, more preferably 10% by mass or more and 99% by mass or less, particularly preferably 40% by mass or more and 99% by mass or less, and still more preferably 50% by mass or more and 97% by mass. % by mass or less, particularly preferably 70% by mass or more and 97% by mass or less, and extremely preferably 75% by mass or more and 95% by mass or less.

The colored curable resin composition of the present invention is prepared by dispersing all or part of the compound (I) in all or part of the solvent (E) to prepare a colored dispersion, and then using this colored dispersion. may be prepared using

The content of solids in the colored dispersion may be, for example, 0.01% by mass or more and 99.99% by mass or less, preferably 0.1% by mass or more and 99.9% by mass, relative to the total amount of the colored dispersion. % by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, still more preferably 1% by mass or more and 90% by mass or less, more preferably 1% by mass or more and 60% or less, It is 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 content of compound (I) in the colored dispersion may be, for example, 0.0001% by mass or more, preferably 0.01% by mass or more, more preferably 0.01% by mass or more, based on the total amount of solids in the colored dispersion. is 1% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, still more preferably 20% by mass or more, and particularly preferably 30% by mass or more. On the other hand, the upper limit of the content of compound (I) in the colored dispersion is usually 100% by mass or less, and may be, for example, 99% by mass or less, based on the total solid content in the colored dispersion.

When all or part of the compound (I) is dispersed in all or part of the solvent (E) to prepare a colored dispersion, all or part of the resin (B) is included to obtain a colored dispersion. The dispersion stability of the dispersion can be further improved. The content of the resin (B) in the colored dispersion may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass, relative to 100 parts by mass of the compound (I). or less, more preferably 1 to 500 parts by mass, particularly preferably 5 to 200 parts by mass, and even more preferably 10 to 100 parts by mass.

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

The compound (I) can be uniformly dispersed in the colored dispersion by adding a dispersant and performing a dispersion treatment. The compounds (I) may be dispersed individually, or may be mixed and dispersed.

Examples of the dispersant include surfactants, and cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples include surfactants such as polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. As the dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (manufactured by BASF Corporation), 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. mentioned.

When a dispersant is used, the amount of the dispersant (solid content) used is 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass, relative to 100 parts by mass of compound (I). or less, more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, still more preferably 100 parts by mass or less, still more preferably 5 parts by mass or more and 100 parts by mass or less, especially It is 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, there is a tendency to obtain a colored dispersion in a more uniformly dispersed state.

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

[Leveling agent (F)]
Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.
Examples of silicone-based surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray SH7PA, Toray DC11PA, Toray SH21PA, Toray SH28PA, Toray SH29PA, Toray SH30PA, Toray SH8400 (trade name: 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), etc. .

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

Examples of fluorine atom-containing silicone-based surfactants include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, F477 and F443 (manufactured by DIC Corporation) and the like can be mentioned.

When the leveling agent (F) is contained, 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, more preferably 0.001% by mass or more and 0.5% by mass or less, still more preferably 0.002% by mass or more and 0.2% by mass or less, and particularly preferably 0.005% by 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]
From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more. The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and phenol antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like can be used.

Examples of the phenol-based antioxidant include, for example, 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 (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 (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, manufactured by Sumitomo Chemical Co., Ltd., Sumilizer GS , manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec Co., Ltd.), vitamin E (manufactured by Eisai Co., Ltd.), and the like.

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), ADEKA STAB 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), Weston 618 (Weston 618, manufactured by GE), Weston 619G (Weston 619G, GE) company), Ultranox 626 (manufactured by GE) and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4, 8,10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphosphepin) (manufactured by Sumitomo Chemical Co., Ltd.) and the like.

Examples of the sulfur-based antioxidant include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and 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 optionally contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, light stabilizers and chain transfer agents. .
Examples of adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycidide. Xypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercapto propyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-amino Propylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3 -aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane.

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

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

The film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose and application. 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 obtained by forming a thin film of aluminum, silver, silver/copper/palladium alloy, or the like on the substrate is used. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by the photolithographic method can be carried out using a known or commonly used apparatus and conditions. For example, it can be produced as follows.
First, a colored curable resin composition is applied onto a substrate, and dried by heating and drying (pre-baking) and/or under reduced pressure to remove volatile components such as a solvent, thereby forming a smooth colored curable resin composition layer. obtain.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.

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

Next, the colored curable resin composition layer is exposed through a photomask to form a desired colored pattern. Exposure devices such as mask aligners and steppers are capable of uniformly irradiating the entire exposure surface with parallel light beams and of accurately aligning the photomask with the substrate on which the colored curable resin composition layer is formed. is preferably used.

As a light source used for exposure, a light source that 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 is cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges. You can Specifically, mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, and the like can be used.

A colored pattern is formed on the substrate by contacting the exposed colored curable resin composition layer with a developer for development. By development, the unexposed portion of the colored curable resin composition layer is dissolved in the developer and removed.
As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate and tetramethylammonium hydroxide are preferred. 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 a puddle method, a dipping method, a spray method, and the like. Furthermore, the substrate may be tilted at any angle during development.
The substrate after development is preferably washed with water.
Furthermore, it is preferable to post-bake the obtained colored pattern.

The color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, particularly as a color filter used in liquid crystal display devices.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples, and can be modified appropriately within the scope that can conform to the gist of the above and later descriptions. It is of course possible to implement them, and all of them are included in the technical scope of the present invention. In the following description, "parts" means "parts by mass" and "%" means "% by mass" unless otherwise specified.

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

The polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: Tetrahydrofuran Flow rate: 1.0 mL/min Solid content concentration of analysis sample: 0.001 to 0.01% by mass
Injection volume: 50 μL
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 polystyrene-equivalent weight-average molecular weight and the number-average molecular weight obtained above was defined as the degree of dispersion.

<Preparation of compound I-1>
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 80 parts of water were mixed. While maintaining the temperature of the obtained mixture at 60°C, 8.0 parts of potassium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 60°C for 6 hours. 263 parts of pre-diluted sulfuric acid (7.4 parts of concentrated sulfuric acid and 256 parts of water) was added while maintaining the temperature of the resulting mixture below 5° C., resulting in an orange precipitate. The mixture containing this orange precipitate was filtered, and the filtered residue was washed with 300 parts of water and 300 parts of methanol. The resulting residue was dried under reduced pressure at 60° C. to obtain 6.1 parts of compound I-1 represented by formula (I-1) (yield 70%).

<Identification of Compound I-1>
(Mass spectrometry) Ionization mode = ESI-: m/z = [M-H] ^-427
Exact Mass: 428

<Preparation of compound I-2>
10 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.4 parts of potassium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.), and 57 parts of water are mixed. bottom. The temperature of the resulting mixture was heated to 100° C. and stirred for 6 hours. While maintaining the temperature of the resulting mixture below 5°C, 1000 parts of acetone was added. The resulting mixture was filtered, and the residue after filtration was washed with 25 parts of acetone three times. The resulting residue was dried under reduced pressure at 60° C. to obtain 12 parts of compound I-2a represented by formula (I-2a) (yield 80%).

1.2 parts of the compound represented by compound (1-2a) and 103 parts of water were added and dissolved. 0.98 parts of magnesium acetate tetrahydrate and 227 parts of water were added dropwise at 23°C, and the mixture was stirred at 23°C for 6 hours to produce a red precipitate. The mixture containing this red precipitate was filtered, and the filtered residue was washed three times with 1 part of water. The resulting residue was dried under reduced pressure at 60° C. to obtain 0.24 parts of compound I-2 represented by formula (I-2) (yield 25%).

<Preparation of compound I-3>
Synthesis was carried out in the same manner as in Example 2, except that 1.2 parts of barium acetate was added dropwise in place of the dropwise addition of 0.98 parts of magnesium acetate tetrahydrate. The precipitate obtained by dropping 1.2 parts of barium acetate was also red. 1.3 parts of compound I-3 represented by formula (I-3) was obtained (yield 91%).

<Preparation of compound I-4>
10 parts of diisobutyl 3,9-perylenedicarboxylate (Solvent Green 5, manufactured by Tokyo Chemical Industry Co., Ltd.), 2.8 parts of potassium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.), and 28 parts of water were mixed, °C and stirred for 15 hours. When 6.2 parts of concentrated sulfuric acid was added while maintaining the temperature of the resulting mixture at 5°C or less, a yellow precipitate was formed. The mixture containing this yellow precipitate was filtered, and the filtered residue was washed with 100 parts of water three times. The resulting residue was dried under reduced pressure at 60° C. to obtain 6.2 parts of compound I-4 represented by formula (I-4) (yield 83%).

<Identification of compound I-4>
(Mass spectrometry) Ionization mode = ESI-: m/z = [M-H] ^-339
Exact Mass: 340

<Preparation of compound I-5>
3.5 parts of diisobutyl 4,10-dicyanoperylene-3,9-dicarboxylate (Lumogen (registered trademark) F Yellow 083, manufactured by BASF Corporation) and 1.6 parts of sodium hydroxide (Wako Pure Chemical Industries, Ltd.) ) and 35 parts of water were mixed and stirred at 100°C for 10 hours. When 5.2 parts of concentrated hydrochloric acid was added while maintaining the temperature of the resulting mixture at 5°C or lower, an orange precipitate was formed. A mixture containing an orange precipitate was filtered, and the filtered residue was washed three times with 100 parts of water. The resulting residue was dried under reduced pressure at 60° C. to obtain 2.6 parts of compound I-5 represented by formula (I-5) (yield 93%).

<Identification of Compound I-5>
(Mass spectrometry) Ionization mode = ESI-: m/z = [M-H] ^-389
Exact Mass: 390

Synthesis example 1
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to create a nitrogen atmosphere. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2, 6} ] A mixed solution of 289 parts of a mixture of decane-9-yl acrylate (content ratio is 1:1 in terms of molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, it was held at 80° C. for 4 hours, then cooled to room temperature, and a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23° C.) was obtained. got The resulting copolymer had a weight average molecular weight Mw of 9.2×10 ³ , a dispersity of 2.08, and an acid value converted to solid content of 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 a bead mill was used to disperse the colorant to obtain a colored composition 1.
Coloring agent: 50 parts of compound I-1;
Dispersant: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 58 parts;
Resin (B): 93 parts of resin B1 solution;
Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

Then, the 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): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) 15 parts;
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate;
Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Dow Corning Toray Co., Ltd.) 0.12 parts

(2) Preparation of colored coating film On a 5 cm square glass substrate (Eagle XG; manufactured by Corning), the colored curable resin composition is spin-coated so that the film thickness after post-baking is 1.7 to 2 μm. After coating according to the method, pre-baking was performed at 100° C. for 3 minutes to form a colored curable resin composition layer. After standing to cool, the colored curable resin composition layer formed on the substrate is exposed to an exposure amount of 80 mJ/cm ² (365 nm standard) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). ) was irradiated with light. After light irradiation, post-baking was performed in an oven at 230° C. for 30 minutes to obtain a colored coating film.

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

(4) Light resistance test An ultraviolet cut filter (COLORED OPTICAL GLASS L38; Hoya Co., Ltd.; cuts light of 380 nm or less) is placed on the obtained colored coating film, and a light resistance tester (SUNTEST CPS +: Toyo Seiki After irradiation with xenon lamp light for 48 hours, the absorbance was measured with a colorimeter. The absorbance retention rate was obtained from the absorbance change at the maximum absorption wavelength of the colored coating film before and after the light resistance test.

Examples 2-5 and Comparative Example 1
Instead of 50 parts of compound (I-1) as a coloring agent,
50 parts of compound (I-2) (Example 2),
50 parts of compound (I-3) (Example 3),
50 parts of compound (I-4) (Example 4),
50 parts of compound (I-5) (Example 5),
50 parts of Solvent Green 5 (manufactured by Tokyo Chemical Industry Co., Ltd.) (Comparative Example 1)
was the same as in Example 1, except that . Table 2 shows the results.

Claims (3)

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

[In the formula,
R ¹ to R ³ each independently represent a hydrogen atom, —CO ₂ ⁻ , a halogen atom, a cyano group, a nitro group, or an optionally substituted hydrocarbon group having 1 to 40 carbon atoms.
R ⁴ to R ¹¹ each independently represent an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, cyano group, nitro group, —CO ₂ ⁻ , or —S(O) ₂ O ^— .
—CH ² — which is included in the optionally substituted hydrocarbon group having 1 to 40 carbon atoms and does not form a ring, represented by R 4 to R ¹¹ _, and R ⁴ to R ¹¹ —CH ₂ — contained in the represented heterocyclic group optionally having substituent(s) and not forming a ring, —O—, —CO—, —S(O) ₂ —, —NR ^x1 — may be replaced by 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.
M ^x+ represents a hydrogen or an x-valent metal cation.
x represents an integer of 2 or more.
a represents the valence of the structure in parentheses with a and represents an integer of 1 or more and 12 or less.
b represents the number of M ^X+ and represents an integer of 1 or more and 12 or less.
a and b are represented by the following formula:
a=bx
meet. ] A color filter formed from the colored curable resin composition according to claim 1 . A display device comprising the color filter according to claim 2 .