JP7412141B2 - coloring composition - Google Patents

Description

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

In the field of organic semiconductor materials, materials containing perylenetetracarboxylic acid diimide compounds are known (Patent Document 1).

International Publication No. 2011/105152

In the field of colorants, colorants containing fluorescent dyes are used, and coloring compositions containing such colorants are required to have improved heat resistance.

An object of the present invention is to provide a colored composition with excellent heat resistance.

［式（Ｉ）中、
Ｒ^１～Ｒ^４は、互いに独立に、炭素数５～１０のアルキル基を表す。
Ｒ^５～Ｒ^１２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、水素原子、ハロゲン原子、又はニトロ基を表す。］
［２］ 前記式（Ｉ）で表される化合物とは構造の異なる化合物は、赤色蛍光染料である、［１］に記載の着色組成物。
［３］ 前記赤色蛍光染料は、下記式（ＩＩ）で表される化合物である、［１］又は［２］に記載の着色組成物。

［式（ＩＩ）中、
Ａｒ^１～Ａｒ^６は、互いに独立に、置換基を有していてもよいアリール基を表す。
Ｒ^１５～Ｒ^１８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、水素原子、ハロゲン原子、又はニトロ基を表す。]
［４］ 下記式（Ｉ）で表される化合物と、蛍光染料と、樹脂と、重合性化合物と、重合開始剤と、溶剤とを含む着色硬化性樹脂組成物。

［式（Ｉ）中、
Ｒ^１～Ｒ^４は、互いに独立に、炭素数５～１０のアルキル基を表す。
Ｒ^５～Ｒ^１２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、水素原子、ハロゲン原子、又はニトロ基を表す。］
［５］ ［４］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。
［６］ ［５］に記載のカラーフィルタを含む表示装置。 The present invention provides the following colored composition, colored curable resin composition, color filter, and display device.
[1] A coloring composition containing a colorant and a resin, wherein the colorant contains a compound represented by the following formula (I) and a fluorescent dye, and the fluorescent dye is a compound represented by the formula (I). A coloring composition containing a compound having a different structure from the compound represented by.

[In formula (I),
R ¹ to R ⁴ each independently represent an alkyl group having 5 to 10 carbon atoms.
R ⁵ to R ¹² each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ]
[2] The colored composition according to [1], wherein the compound having a different structure from the compound represented by formula (I) is a red fluorescent dye.
[3] The colored composition according to [1] or [2], wherein the red fluorescent dye is a compound represented by the following formula (II).

[In formula (II),
Ar ¹ to Ar ⁶ each independently represent an aryl group which may have a substituent.
R ¹⁵ to R ¹⁸ each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ]
[4] A colored curable resin composition containing a compound represented by the following formula (I), a fluorescent dye, a resin, a polymerizable compound, a polymerization initiator, and a solvent.

[In formula (I),
R ¹ to R ⁴ each independently represent an alkyl group having 5 to 10 carbon atoms.
R ⁵ to R ¹² each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ]
[5] A color filter formed from the colored curable resin composition according to [4].
[6] A display device including the color filter according to [5].

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

(1) Coloring Composition The coloring composition of the present invention includes a colorant (hereinafter also referred to as colorant (A)) and a resin (hereinafter also referred to as resin (B)).
The colorant (A) contains a compound represented by formula (I) (hereinafter also referred to as compound (I)) and a fluorescent dye (hereinafter also referred to as fluorescent dye (a)).
The fluorescent dye (a) includes a compound having a different structure from the compound represented by formula (I). Compounds with different structures preferably mean compounds with different structures (chemical structures) when expressed by chemical formulas.
The compound having a different structure from the compound represented by formula (I) may be, for example, a red fluorescent dye.
The red fluorescent dye may be, for example, a compound represented by formula (II) (hereinafter also referred to as compound (II)).
The colorant (A) may contain a colorant other than the compound (I) and the fluorescent dye (a) (hereinafter also referred to as a colorant (A1)).
The colorant (A) may contain one or more colorants (A1).
The coloring composition may contain a solvent (hereinafter also referred to as solvent (E)).
Compound (I) and compound (II) may be dispersed in solvent (E).

<Compound (I)>
The alkyl group represented by R ¹ to R ⁴ has 5 to 10 carbon atoms, preferably 5 to 8 carbon atoms. The alkyl group represented by R ¹ to R ⁴ may be linear, branched, or cyclic, and preferably linear.

Examples of the linear alkyl group represented by R ¹ to R ⁴ include n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group and n-decyl group. It will be done. Among these, n-pentyl group, n-hexyl group, n-heptyl group and n-octyl group are preferred, and n-pentyl group and n-hexyl group are more preferred. These groups are preferred from the viewpoint of solubility in solvents and fluorescence intensity.

Examples of the branched alkyl group represented by R ¹ to R ⁴ include 1-methylbutyl group, 1-methylpentyl group, 1-methylhexyl group, 1-methylheptyl group, 1-methyloctyl group, and 1-methylheptyl group. Methylnonyl group, 1-ethylpropyl group, 1-ethylbutyl group, 1-ethylpentyl group, 1-ethylhexyl group, 1-ethylheptyl group, 1-ethyloctyl group, 2-methylbutyl group, 2-methylpentyl group, 2- Methylhexyl group, 2-methylheptyl group, 2-methyloctyl group, 2-methylnonyl group, 2-ethylpropyl group, 2-ethylbutyl group, 2-ethylpentyl group, 2-ethylhexyl group, 2-ethylheptyl group, 2 -ethyloctyl group and the like.

Examples of the cyclic alkyl group represented by R ¹ to R ⁴ include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and the like.

R ¹ to R ⁴ may each independently be, for example, a group combining a linear alkyl group and a cyclic alkyl group, or a group combining a branched alkyl group and a cyclic alkyl group. The number of carbon atoms in these combined groups may be 5 to 10.

R ¹ to R ⁴ may be of the same type or different types, and preferably are of the same type.

Specific examples of R ¹ to R ⁴ include groups represented by the following formulas. * represents a bond.

Examples of the halogen atom represented by R ⁵ to R ¹² include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, fluorine atoms and chlorine atoms are preferred.

Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R ⁵ to R ¹² include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain or cyclic.

The saturated or unsaturated chain aliphatic hydrocarbon groups represented by R ⁵ to R ¹² include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, Decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group , heptacocyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl group, tritriacontyl group, tetratriacontyl group, pentatriacontyl group, hexatriacontyl group, heptatriacontyl group, Linear alkyl groups such as octatriacontyl group, nonatriacontyl group, tetracontyl group, etc.; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group group, tert-pentyl group, (1-methyl)pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, isohexyl group, (5-methyl)hexyl group, Branched alkyl groups such as (2-ethyl)hexyl group and (3-ethyl)heptyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group , 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, 2-pentenyl group, and other alkenyl groups; etc. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10. Among these, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferred, and a methyl group or an ethyl group is particularly preferred.

The saturated or unsaturated alicyclic hydrocarbon group represented by R ⁵ to R ¹² includes cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group. group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5 - cycloalkyl groups such as tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group; cyclohexenyl group (e.g. cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, Cycloalkenyl groups such as a cyclooctenyl group; examples include a norbornyl group, an adamantyl group, a bicyclo[2.2.2]octyl group, and the like. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, particularly preferably 4 to 15, The number is more preferably 5 to 15, particularly preferably 5 to 10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group is most preferred.

The aromatic hydrocarbon groups represented by R ⁵ to R ¹² include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethyl group. Phenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group , 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3 , 5-di(tert-butyl)phenyl group, mesityl group, 4-ethylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 5,6, 7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecyl group Aromatic hydrocarbon groups such as phenyl group and pyrenyl group; and the like. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 15 carbon atoms.

The hydrocarbon groups represented by R ⁵ to R ¹² include a combination of two or more of the hydrocarbon groups listed above, such as an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group. Examples include aralkyl groups such as benzyl group, phenethyl group, and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group). ; Arylalkynyl groups such as phenylethynyl groups; phenyl groups to which one or more phenyl groups are bonded such as biphenylyl groups and terphenylyl groups; cyclohexylmethylphenyl groups, benzylphenyl groups, (dimethyl(phenyl)methyl)phenyl groups, etc. It will be done.

The hydrocarbon group represented by R ⁵ to R ¹² may be a combination of two or more of the hydrocarbon groups listed above, such as a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples include cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, adamantylmethyl group. Examples include alkyl groups to which one or more alicyclic hydrocarbon groups such as groups are bonded.

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

Examples of substituents that the hydrocarbon group having 1 to 40 carbon atoms represented by R ⁵ to R ¹² may have include, for example, a halogen atom, a formyl group, a carboxy group, a formyloxy group, a hydroxy group, and a thiol group. group, sulfo group, sulfamoyl group, pentafluorosulfanyl group, carbamoyl group, amino group, nitro group, cyano group, -COR ¹² , -COOR ¹³ , -OCOR ¹³ , -OR ¹³ , -SR ¹³ , -SOR ¹³ , - SO ₂ R ¹³ , -SO ₂ NHR ¹³ , -SO ₂ NR ¹³ R ¹⁴ , -CONHR ¹³ , -CONR ¹³ R ¹⁴ , -NHR ¹³ , -NR ¹³ R ¹⁴ , -NHCOR ¹³ , -NR ¹⁴ COR ¹³ , etc. Can be mentioned.

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

R ¹³ and R ¹⁴ each independently represent an alkyl group, a phenyl group or a naphthyl group.

The number of carbon atoms in the alkyl group represented by R ¹³ and R ¹⁴ is preferably 1 to 20, more preferably 1 to 10, and still more preferably 1 to 5.

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

-COR ¹³ includes acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, Examples include undecanoyl group, dodecanoyl group, henicosanoyl group, and benzoyl group.

-COOR ¹³ includes methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxy Examples include carbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, and the like.

-OCOR ¹³ includes acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl)hexanoyloxy group, heptanoyloxy group, Noyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, 2-propenylcarbonyloxy group Examples include groups.

Examples of -OR ¹³ include methoxy, ethoxy, propoxy, butoxy, pentyloxy, phenoxy, and naphthyloxy groups.

-SR ¹³ includes methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, butylsulfanyl group, tert-butylsulfanyl group, pentylsulfanyl group, hexylsulfanyl group, (2-ethyl)hexylsulfanyl group, heptylsulfanyl group, octyl Examples include sulfanyl group, nonylsulfanyl group, decylsulfanyl group, undecylsulfanyl group, dodecylsulfanyl group, icosylsulfanyl group, phenylsulfanyl group, and o-tolylsulfanyl group.

-SOR ¹³ includes a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, a phenylsulfinyl group, a naphthylsulfinyl group, and the like.

Examples of -SO ₂ R ¹³ include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a phenylsulfonyl group, a naphthylsulfonyl group, and the like.

-SO ₂ NHR ¹³ includes N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N- Isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group Moyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N- Examples include undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamoyl group, and N-phenylsulfamoyl group.

-SO ₂ NR ¹³ R ¹⁴ is N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group group, N,N-dipropylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N- Diisobutylsulfamoyl group, N,N-disec-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group Moyl group, N,N-dipentylsulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group Moyl group, N,N-diheptylsulfamoyl group, N,N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decyl Methylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group group, N,N-diphenylsulfamoyl group, and the like.

-CONHR ¹³ includes N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N- Examples include octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamoyl group, N-phenylcarbamoyl group, and the like.

-CONR ¹³ R ¹⁴ includes N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group , N,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec-butylcarbamoyl group, N, N-di-tert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N,N-dipentylcarbamoyl group, N,N-di(1 -ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N,N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N -Dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group group, N,N-phenylmethylcarbamoyl group, N,N-diphenylcarbamoyl group, and the like.

-NHR ¹³ includes N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N- Examples include decylamino group, N-undecylamino group, N-dodecylamino group, N-icosylamino group, N-phenylamino group, and the like.

-NR ¹³ R ¹⁴ includes N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N,N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N -di-tert-butylamino group, N,N-butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N -dihexylamino group, N,N-di(2-ethyl)hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group group, N,N-undecylmethylamino group, N,N-dodecylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc. It will be done.

-NHCOR ¹³ includes acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, Examples include heptanoylamino group, octanoylamino group, nonanoylamino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, icosanoylamino group, and benzoylamino group.

-NR ¹⁴ COR ¹³ includes N-methyl-N-acetylamino group and the like.

-CH ₂ - included in the hydrocarbon group having 1 to 40 carbon atoms represented by R ⁵ to R ¹² and not forming a ring is -O-, -CO-, -S(O) ₂ -, - It may be replaced by NR ^x1 -. However, -COOH and -S(O) ₂ OH are not formed by replacing -CH ₂ -. R ^x1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, isopropyl group, isobutyl group, sec-butyl group, and isopentyl group.

Examples of R ⁵ to R ¹² include groups represented by the following formulas. * represents a bond.

R ⁵ to R ¹² are preferably hydrogen atoms, halogen atoms, hydroxy groups, nitro groups, cyano groups, -CH ₃ , formulas (D-1) to (D-18), (E-1) to (E -27), (F-1) to (F-18) and (G-1) to (G-27). From the viewpoint of fluorescence intensity, R ⁵ to R ¹² are preferably hydrogen atoms.

Specific examples of compound (I) include the compounds shown in Table 1 below.

Among them, compound (I-1) and compound (I-2) are preferred. These compounds tend to have high solubility in solvents and high fluorescence intensity.

A preferred embodiment of compound (I) in the present invention includes a compound represented by the following formula (I-1) (hereinafter also referred to as compound (I-1)).

Another preferred embodiment of compound (I) in the present invention includes a compound represented by the following formula (I-2) (hereinafter also referred to as compound (I-2)).

Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (n1) in a solvent.

［式中、Ｒ^５～Ｒ^１２は、上述の定義と同一である。］

[In the formula, R ⁵ to R ¹² are the same as defined above. ]

H ₂ NCHR ¹ R ² (n1)
[wherein R ¹ and R ² are the same as defined above. ]

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

Examples of the compound represented by formula (n1) include 1-pentylhexylamine (6-aminoundecane) and 1-hexylheptylamine (7-aminotridecane). The compound represented by formula (n1) may be used alone or in combination of two or more.

The amount of the compound represented by formula (n1) to be used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, per 1 mol of the compound represented by formula (pt1). , more preferably 1 mol or more and 6 mols or less, still more preferably 1 mol or more and 4 mols or less.

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

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

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

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

Compound (I-1) can be produced, for example, by reacting 3,4,9,10-perylenetetracarboxylic dianhydride and 1-hexylheptylamine in a solvent.

Compound (I-2) can be produced, for example, by reacting 3,4,9,10-perylenetetracarboxylic dianhydride and 1-pentylhexylamine in a solvent.

<Fluorescent dye (a)>
The fluorescent dye (a) is a dye having fluorescent performance (photoluminescence), and includes a compound having a different structure from the compound represented by formula (I). The compound having a different structure from the compound represented by formula (I) is preferably a red fluorescent dye.

［式（ＩＩ）中、
Ａｒ^１～Ａｒ^６は、互いに独立に、置換基を有していてもよいアリール基を表す。
Ｒ^１５～Ｒ^１８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、水素原子、ハロゲン原子、又はニトロ基を表す。] The red fluorescent dye may be, for example, a compound represented by the following formula (II) (hereinafter also referred to as compound (II)).

[In formula (II),
Ar ¹ to Ar ⁶ each independently represent an aryl group which may have a substituent.
R ¹⁵ to R ¹⁸ each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ]

Examples of the aryl group represented by Ar ¹ to Ar ⁶ include a phenyl group and a naphthyl group. The aryl group represented by Ar ¹ to Ar ⁶ is preferably a phenyl group.

Examples of substituents that the aryl group represented by Ar ¹ to Ar ⁶ may have include a halogen atom, a nitrile group, a nitro group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, and a 3 to 10 carbon atom. Cycloalkyl group, alkenyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, aryloxy group, thiol group, alkylthio group having 1 to 10 carbon atoms, allylthio group, sulfoxy group, having 1 to 10 carbon atoms Alkyl sulfoxy group, arylsulfoxy group, silyl group, boron group, arylamine group, aralkylamine group, alkylamine group having 1 to 10 carbon atoms, aryl group, aralkyl group, arylalkenyl group, having 3 to 10 carbon atoms Examples include substituents selected from the group consisting of heterocyclic groups and acetylene groups. Among these, alkyl groups having 1 to 10 carbon atoms and halogen atoms are preferred.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, fluorine atoms and chlorine atoms are preferred.
The alkyl group having 1 to 10 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms.

The aryl group represented by Ar ¹ to Ar ⁶ may or may not have one or more substituents.

Examples of Ar ¹ to Ar ⁶ include groups represented by the following formulas. * represents a bond.

Preferred as Ar ¹ to Ar ⁶ are formulas (E-1), (E-4), (E-7), (E-9), (E-17), (E-18), (E- 19). These groups tend to have high fluorescence intensity. Preferably, Ar ¹ and Ar ² are the same. Ar ³ to Ar ⁶ may be of the same type or may be of different types.

Specific examples of compound (II) include the compounds shown in Tables 2 to 6 below.

Preferably, compounds (II-2), (II-4), (II-7), (II-10), (II-13), (II-64) to (II-108) are more preferable. are compounds (II-2), (II-4), (II-7), (II-10), (II-91) to (II-99), more preferably compound (II-2) and (II-92). These compounds tend to have high solubility in solvents and high fluorescence intensity.

Another preferred embodiment of compound (II) in the present invention is a compound represented by the following formulas (II-2) and (II-92), respectively (hereinafter, compound (II-2), compound (II-92) ).

Compound (II) is produced, for example, by reacting a compound represented by the following formula (pt2), a compound represented by the following formula (AR1), and a compound represented by the following formula (AR2) in a solvent. be able to.

［式中、Ｒ^５～Ｒ^１２は、上述の定義と同一である。］

[In the formula, R ⁵ to R ¹² are the same as defined above. ]

Ar-NH ₂ (AR1)
Ar-OH (AR2)
[In the formula, Ar is the same as the definition of Ar ¹ to Ar ⁶ above.] ]

Examples of the compound represented by formula (pt2) include 1,6,7,12-tetrachloroperylenetetracarboxylic dianhydride.

Examples of the compound represented by formula (AR1) include 2,6-diisopropylaniline, aniline, 3,5-dimethylalinine, and 3,5-di-tert-butylaniline. The compound represented by formula (AR1) may be used alone or in combination of two or more.

Examples of the compound represented by formula (AR2) include phenol, 4-fluorophenol, 4-chlorophenol, 4-bromophenol, and the like. The compound represented by formula (AR1) may be used alone or in combination of two or more.

The total amount of the compound represented by formula (AR1) and the compound represented by formula (AR2) is usually 1 mol or more and 10 mol or less per 1 mol of the compound represented by formula (pt2). , preferably 1 mol or more and 8 mols or less, more preferably 1 mol or more and 6 mols or less, still more preferably 1 mol or more and 4 mols or less.

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, 1 - Alcohol solvents such as octanol and phenol; Ether solvents such as diethyl ether and tetrahydrofuran; Ketone solvents such as acetone and methyl isobutyl ketone; Ester solvents such as ethyl acetate; Aliphatic hydrocarbon solvents such as hexane; aromatic carbonization such as toluene Hydrogen solvents; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, acetic acid, propionic acid, Examples include carboxylic acid solvents such as butyric acid, imidazole, and the like. Preferred are N-methylpyrrolidone, imidazole, and propionic acid.

The amount of the solvent used is usually 1 to 1000 parts by weight per 1 part by weight of the compound represented by formula (pt2).

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

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

Compound (II-2) can be produced by reacting 1,6,7,12-tetrachloroperylenetetracarboxylic dianhydride with 2,6-diisopropylaniline and phenol in a solvent.

Representative commercial products of compound (II-2) include Lumogen (registered trademark) F Red 305 and the like.

<Coloring agent (A)>
The lower limit of the content of compound (I) in the colorant (A) may be, for example, 0.1% by mass or more based on the total amount of the colorant (A), and a specific example thereof is 0.1% by mass or more. It may be 5% by weight, 1% by weight, 5% by weight, 10% by weight, 20% by weight, 50% by weight, 70% by weight, 90% by weight, etc.
On the other hand, the upper limit of the content of compound (I) in the colorant (A) may be, for example, 99.9% by mass or less based on the total amount of the colorant (A). It may be 99.5% by weight, 99% by weight, 95% by weight, 90% by weight, 80% by weight, 50% by weight, 30% by weight, 10% by weight, etc.
For example, when the colorant (A) contains compound (I) and compound (II), the content of compound (I) in the colorant (A) is, for example, 1% with respect to the total amount of the colorant (A). It may be at least 5% by mass and at most 99% by mass, preferably at least 5% by mass and at most 70% by mass, more preferably at least 10% by mass and at most 50% by mass.

The lower limit of the content of the fluorescent dye (a) in the colorant (A) may be, for example, 0.1% by mass or more based on the total amount of the colorant (A), and a specific example is 0.1% by mass or more. It may be .5% by weight, 1% by weight, 5% by weight, 10% by weight, 20% by weight, 50% by weight, 70% by weight, 90% by weight, etc.
On the other hand, the upper limit of the content of the fluorescent dye (a) in the colorant (A) may be, for example, 99.9% by mass or less based on the total amount of the colorant (A). It may be 99.5% by mass, 99% by mass, 95% by mass, 90% by mass, 80% by mass, 50% by mass, 30% by mass, 10% by mass or less.
For example, when the colorant (A) contains compound (I) and compound (II), the content of compound (II) in the colorant (A) is, for example, 1% relative to the total amount of the colorant (A). The content may be 99% by mass or less, preferably 30% by mass or more and 95% by mass or less, and more preferably 50% by mass or more and 90% by mass or less.

The content of a compound having a different structure from the compound represented by formula (I) in the fluorescent dye (a) may be, for example, 0.1% by mass or more based on the total amount of the fluorescent dye (a), Preferably it is 0.5% by mass or more, more preferably 1% by mass or more, even more preferably 5% by mass or more, particularly preferably 10% by mass or more, and even more preferably 20% by mass or more. , even more preferably 50% by mass or more, particularly preferably 70% by mass or more, and extremely preferably 90% by mass or more.
On the other hand, the content of the fluorescent dye (a) in the colorant (A) is usually less than 100% by mass, preferably 99.5% by mass or less, more preferably 99% by mass or less, more preferably 95% by mass or less, particularly preferably 90% by mass or less, even more preferably 80% by mass or less, even more preferably 50% by mass or less, particularly preferably 30% by mass or less, and extremely preferably is 10% by mass or less.

When compound (II) is a compound having a different structure from the compound represented by formula (I), the lower limit of the content of compound (II) in colorant (A) is the total amount of colorant (A). For example, it may be 0.1% by mass or more, and specific examples thereof are 0.5% by mass, 1% by mass or more, 5% by mass or more, 10% by mass, 20% by mass, 50% by mass, and 70% by mass. , 90% by mass, etc.
On the other hand, the upper limit of the content of compound (II) in the colorant (A) may be, for example, 99.9% by mass or less based on the total amount of the colorant (A), and a specific example thereof is 99.9% by mass or less. It may be 5% by mass, 99% by mass, 95% by mass, 90% by mass, 80% by mass, 50% by mass, 30% by mass, 10% by mass, etc.

When the colorant (A) contains the compound (I) and the fluorescent dye (a), the fluorescence intensity of the fluorescent dye (a) tends to improve.

The mass ratio of compound (I) and fluorescent dye (a) in colorant (A) may be, for example, 1:99 to 99:1, preferably 20:80 to 80:20, more preferably 30. :70 to 70:30. When the mass ratio of compound (I) and fluorescent dye (a) in colorant (A) is within the above range, heat resistance and fluorescence intensity tend to be improved.

The mass ratio of compound (I) and compound (II) in colorant (A) may be, for example, 1:99 to 99:1, preferably 20:80 to 80:20, more preferably 30: 70-70:30.

The content of the colorant (A) in the coloring composition may be, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 0.1% by mass or more and 99.9% by mass or less, based on the total amount of solid content in the coloring composition. 5% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 95% by mass or less, still more preferably 3% by mass or more and 90% by mass or less, particularly preferably 10% by mass or more and 80% by mass or less. The content is more preferably 10% by mass or more and 60% by mass or less, even more preferably 10% by mass or more and 35% by mass or less.
As used herein, "total amount of solid content in the coloring composition" refers to the total amount of components excluding all solvent components from the coloring composition. The total amount of solid content and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography.

<Colorant (A1)>
The colorant (A1) may be a dye or a pigment. As the dye, known dyes can be used, such as those described in Color Index (published by The Society of Dyers and Colourists) and Dyeing Note (Shirosensha). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline Examples include dyes, nitro dyes, phthalocyanine dyes, perylene dyes, and the like. These dyes may be used alone or in combination of two or more.

Specifically, dyes having the following color index (C.I.) numbers may be mentioned.
C. I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
C. I. Solvent red 24, 45, 49, 90, 91111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
C. I. Solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. C.I. such as Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. I. solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C. I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;
C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, C. 104, 105, 106, 109, etc. I. acid dye,
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. C. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82, etc. I. direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C.I. such as Disperse Blue 1, 14, 56, 60, etc. I. disperse dye,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C. I. Basic Violet 2;
C. I. Basic Red 9;
C. I. C. such as Basic Green 1; I. basic dye,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. C. such as Reactive Red 36; I. reactive dye,
C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C. I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. C. mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. I. mordant dye,
C. I. Bat green 1st class C. I. Vat dye etc.

Further examples include Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), and Lumogen (registered trademark) F Orange 240 (manufactured by BASF).

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

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

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

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

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

The content of solids in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass, based on the total amount of the colorant-containing liquid. mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, still more preferably 1 mass% or more and 60% or less, even more preferably 3 It is at least 3% by mass and at most 30% by mass, particularly preferably at least 3% by mass and at most 30% by mass, and extremely preferably at least 5% by mass and at most 30% by mass.

The content of the colorant (A) in the colorant-containing liquid is usually less than 100% by mass, preferably 0.0001% by mass or more and 99.9999% by mass or less, based on the total amount of solids in the colorant-containing liquid. It is more preferably 0.01% by mass or more and 99% by mass or less, still more preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 99% by mass or less, and even more preferably Preferably it is 2% by mass or more and 99% by mass or less.
In this specification, the "total amount of solid content in the colorant-containing liquid" refers to the total amount of components excluding the solvent (E) from the colorant-containing liquid. The total solid content and the content of each component relative to the total solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.

The colorant (A1) can be uniformly dispersed in the colorant (A1)-containing liquid by containing a dispersant and performing a dispersion treatment. The coloring agents (A1) may be dispersed individually or in a mixture of two or more types.

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

When a dispersant is used to prepare the colorant-containing liquid, the amount of the dispersant (solid content) used is usually 10,000 parts by mass or less, preferably 10,000 parts by mass or less, based on 100 parts by mass of the colorant (A). 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, even more preferably 100 parts by mass or less, even more preferably It is 5 parts by mass or more and 100 parts by mass or less, particularly preferably 5 parts by mass or more and 50 parts by mass or less. When the amount of the dispersant used is within the above range, a colorant-containing liquid with a more uniformly dispersed state tends to be obtained.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, containing at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as "monomer (a)"). It is more preferable to use a polymer having a structural unit derived from (in some cases).
The resin (B) is a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b)"), and others. It is preferable that it is a copolymer having a structural unit of
Other structural units include monomers copolymerizable with monomer (a) (however, they are different from monomer (a) and monomer (b); hereinafter referred to as "monomer (c)") Examples include structural units derived from (sometimes referred to as), structural units having ethylenically unsaturated bonds, and the like.

Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, Bicyclounsaturated compounds containing a carboxy group such as 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2-ene;
Carboxylic acid anhydrides such as anhydrides of the above unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyhydric carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate. Class;
Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one member selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. means. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
As the monomer (b), for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), an oxetanyl group and an ethylenically unsaturated bond, etc. (hereinafter sometimes referred to as "monomer (b2)") and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b3)") ) etc.

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

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

[In formula (BI) and formula (BII), R ^a and R ^b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group. may be replaced with .
X ^a and X ^b each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S-, or *-R ^c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* represents a bond with O. ]

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

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

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

Examples of alkanediyl groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, Examples include hexane-1,6-diyl group.

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

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

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

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination with the compound represented by formula (BI) and the compound represented by formula (BII). You may. When these are used together, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10: The ratio is 90 to 90:10, more preferably 20:80 to 80:20.

As the monomer (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3 -Acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. can be mentioned.

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

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

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 2-ethylhexyl. (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo [5.2. 1.0 ^2,6 ] Decan-8-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ] Decan-9-yl (meth)acrylate, Tricyclo[5.2.1.0 ^{2 ,6} ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, ) (meth)acrylic acid esters such as acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and benzyl (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate;
Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1] Hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2 .1] hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2 .2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyl) bicyclounsaturated compounds such as (oxycarbonyl)bicyclo[2.2.1]hept-2-ene;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 - dicarbonylimide derivatives such as maleimidopropionate and N-(9-acridinyl)maleimide;
Vinyl group-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth)acrylamide and esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene.
Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1 .0 ^2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^{2, 6} ] decen-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, benzyl (meth)acrylate, and the like are preferred.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. A resin having such a structural unit is a polymer having a structural unit derived from monomer (a) or monomer (b), and a group possessed by monomer (a) or monomer (b). It can be obtained by adding a monomer having an ethylenically unsaturated bond to a group capable of reacting with.
Such structural units include a structural unit in which glycidyl (meth)acrylate is added to a (meth)acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth)acrylate is added to a maleic anhydride unit, and a structural unit in which glycidyl (meth)acrylate is added to a maleic anhydride unit. ) Examples include structural units in which (meth)acrylic acid is added to acrylate units. Furthermore, when these structural units have a hydroxy group, structural units to which carboxylic acid anhydride is further added are also included as structural units having ethylenically unsaturated bonds.

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

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

Specifically, the resin (B) includes 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Decyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid Copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5 .2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth) ) acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/tricyclo[5.2 .1.0 ^2,6 ] Decenyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene Copolymers, benzyl (meth)acrylate/(meth)acrylic acid copolymers, styrene/(meth)acrylic acid copolymers, and JP-A-9-106071, JP-A-2004-29518, and JP-A-2004-2004- Examples include resins described in each publication such as No. 361455.
Among these, as the resin (B), a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) is preferable.

Two or more resins (B) may be used in combination, and in this case, the resin (B) is at least 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate. /(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxy It is preferable to contain one or more selected from tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 1,000 or more and 100,000 or less, more preferably 1,000 or more and 50,000 or less, and still more preferably 1,000 or more. It is 30,000 or less, particularly preferably 3,000 or more and 30,000 or less.

The molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and still more preferably 1.001 or more and 4 or less. 01 or more and 4 or less.

The acid value (solid content equivalent value) of the resin (B) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, and even more preferably 20 mg-KOH/g. -KOH/g or more and 200mg-KOH/g or less, particularly preferably 20mg-KOH/g or more and 170mg-KOH/g or less, even more preferably 30mg-KOH/g or more and 170mg-KOH/g or less, particularly preferably 60mg-KOH /g or more and 150 mg-KOH/g or less, extremely preferably 65 mg-KOH/g or more and 135 mg-KOH/g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

In the colored composition, the content of the resin (B) may be, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 0.5% by mass or less, based on the total amount of solid content in the colored composition. The content is 99% by mass or less, more preferably 1% by mass or more and 95% by mass or less, even more preferably 5% by mass or more and 90% by mass, particularly preferably 20% by mass or more and 90% by mass or less.

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

The content of the resin (B) in the colorant-containing liquid may be, for example, 10,000 parts by mass or less, preferably 5,000 parts by mass or less, and more preferably 1,000 parts by mass, based on 100 parts by mass of the colorant (A). It is not more than 1 part by mass, more preferably not less than 1 part by mass and not more than 500 parts by mass, particularly preferably not less than 5 parts by mass and not more than 200 parts by mass, and even more preferably not less than 10 parts by mass and not more than 100 parts by mass.

<Embodiment 1>
The colored composition according to Embodiment 1 is a colored composition containing a coloring agent (A) and a resin (B), where the coloring agent (A) is a compound represented by the following formula (I-1). and a compound represented by the following formula (II-2).

<Embodiment 2>
The colored composition according to Embodiment 2 is a colored composition containing a coloring agent (A) and a resin (B), where the coloring agent (A) is a compound represented by the following formula (I-2). and a compound represented by the following formula (II-2).

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

The solid content in the colored curable resin composition is adjusted as appropriate depending on the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured. Although not particularly limited, it may be, for example, 1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 90% by mass or less, more preferably 1% by mass or more and 90% by mass or less, based on the total amount of solids in the colored curable resin composition. is 2% by mass or more and 80% by mass or less, more preferably 3% by mass or more and 70% by mass or less, particularly preferably 4% by mass or more and 60% by mass or less, even more preferably 5% by mass or more and 50% by mass. It is particularly preferably 6% by mass or more and 45% by mass or less, and extremely preferably 7% by mass or more and 40% by mass or less.

Each content of the colorant (A) in the colored curable resin composition is adjusted appropriately depending on the chromaticity, brightness, film thickness, etc. required when the colored curable resin composition is cured, and therefore is not particularly limited. However, it may be, for example, 0.1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 90% by mass or less, more preferably 2% by mass or less, based on the total amount of solids in the colored curable resin composition. It is at least 3% by mass and at most 70% by mass, particularly preferably at least 4% by mass and at most 20% by mass.

As used herein, "the total amount of solid content in the colored curable resin composition" refers to the total amount of the components excluding the solvent (E) from the colored curable resin composition. The total amount of solid content and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography. The content of solids in the colored curable resin composition may be, for example, 0.01% by mass or more and less than 100% by mass, preferably 0.1% by mass, based on the total amount of the colored curable resin composition. 99.9% by mass or less, more preferably 0.1% by mass or more and 99% by mass, still more preferably 1% by mass or more and 90% by mass, particularly preferably 1% by mass or more and 60% by mass, and even more preferably The content is preferably 3% by mass or more and 50% by mass or less, even more preferably 3% by mass or more and 30% by mass or less, particularly preferably 5% by mass or more and 30% by mass or less.

The colored patterns and colored coating films described below formed from the colored curable resin composition of the present invention not only have excellent heat resistance but also tend to have high fluorescence intensity at a wavelength of 610 nm, and preferably contain fluorescent dye (a). The fluorescence intensity at a wavelength of 610 nm tends to be higher than that of a colored pattern or a colored coating film formed from a colored curable resin composition containing it alone. The fluorescence intensity can be measured using, for example, a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.).

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond. It is a (meth)acrylic acid ester compound.

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

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

Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa( meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl ) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, Examples include caprolactone-modified pentaerythritol tetra(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate, preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 50 or more and 3,500 or less, even more preferably 50 or more and 3,000 or less, particularly preferably 150 or more and 2,900 or less. and particularly preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 2% by mass or more and 90% by mass, based on the total amount of solid content in the colored curable resin composition. or less, more preferably 5% by mass or more and 80% by mass or less, further preferably 10% by mass or more and 70% by mass or less, particularly preferably 20% by mass or more and 70% by mass or less.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids, etc. under the action of light or heat, and any known polymerization initiator can be used.

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

Examples of O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)- 3-Cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl -6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl) -2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3- Examples include cyclopentylpropan-1-one-2-imine. Further, as the O-acyloxime compound, commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF Corporation) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- At least one selected from the group consisting of 1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyl More preferred is oxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine.

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

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

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

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

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

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

The content of the polymerization initiator (D) is, for example, 0.01% by mass or more and 40% by mass with respect to the total amount of all resins (B) and polymerizable compounds (C) contained in the colored curable resin composition. It may be less than or equal to 1% by mass and preferably 35% by mass or less.

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

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

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

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

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

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

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

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

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

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

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. etc.

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

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

The content of the solvent (E) is usually 99.99% by mass or less, preferably 0.1% by mass or more and 99.9% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, based on the total amount of the colored curable resin composition. is 1% by mass or more and 99.9% by mass or less, more preferably 10% by mass or more and 99% by mass or less, particularly preferably 40% by mass or more and 99% by mass or less, even more preferably 50% by mass or more and 97% by mass or less. It is not more than 70% by mass and not more than 97% by mass, particularly preferably not less than 70% by mass and not more than 90% by mass.

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

The content of solids in the colorant-containing liquid may be, for example, 0.01% by mass or more and 99.99% by mass or less, preferably 0.1% by mass or more and 99% by mass or less, based on the total amount of the colorant-containing liquid. .9 mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, still more preferably 1 mass% or more and 90 mass% or less, and even more preferably 1 mass% or more and 60% or less. , more preferably 3% by mass or more and 50% by mass or less, particularly preferably 3% by mass or more and 30% by mass or less.

The total content of compound (I) and fluorescent dye (a) in the colorant-containing liquid may be, for example, 0.0001% by mass or more, preferably 0.0001% by mass or more, based on the total solid content in the colorant-containing liquid. 01% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more. On the other hand, the upper limit of the total content of compound (I) and compound (II) in the colorant-containing liquid is usually less than 100% by mass, for example 99% by mass or less, based on the total amount of solids in the colorant-containing liquid. It may be.

When preparing a colorant-containing liquid by dispersing all or part of the compound (I) and the fluorescent dye (a) in all or part of the solvent (E), the liquid containing all or part of the resin (B) may be dispersed. By allowing the liquid to stand still, the dispersion stability of the colorant-containing liquid can be further improved. The content of the resin (B) in the colorant-containing liquid may be, for example, 10,000 parts by mass or less, preferably 5,000 parts by mass or less, based on a total of 100 parts by mass of compound (I) and fluorescent dye (a). More preferably 1000 parts by mass or less, still more preferably 1 part by mass or more and 500 parts by mass or less, particularly preferably 5 parts by mass or more and 200 parts by mass or less, even more preferably 10 parts by mass or more and 100 parts by mass. It is as follows.

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

The compound (I) and the fluorescent dye (a) are subjected to a dispersion treatment by containing a dispersant, so that the compound (I) and the fluorescent dye (a) are uniformly dispersed in the colorant-containing liquid. be able to. Compound (I) and fluorescent dye (a) may be dispersed individually, or a plurality of them may be mixed and dispersed. When the colorant (A) contains the compound (I), the fluorescent dye (a), and the dispersant, the dispersibility of the compound (I) is improved and the heat resistance tends to be easily improved.

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

When using a dispersant, the amount of the dispersant (solid content) used is 10,000 parts by mass or less, preferably 5,000 parts by mass or less, based on a total of 100 parts by mass of compound (I) and fluorescent dye (a). , more preferably 1000 parts by mass or less, still more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, even more preferably 100 parts by mass or less, even more preferably 5 parts by mass or more and 100 parts by mass or less. It is not more than 5 parts by mass, particularly preferably not less than 5 parts by mass and not more than 50 parts by mass. When the amount of the dispersant used is within the above range, a colorant-containing liquid with a more uniformly dispersed state tends to be obtained.

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

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

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

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

When containing a leveling agent (F), its content is usually 0.0005% by mass or more and 5% by mass or less, preferably 0.001% by mass or more and 1% by mass or less, based on the total amount of the colored curable resin composition. It is mass %, more preferably 0.001 mass % or more and 0.5 mass % or less, and still more preferably 0.005 mass % or more and 0.1 mass % or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Antioxidant (G)>
From the viewpoint of improving the heat resistance of the colorant, it is preferable to use the antioxidant (G) alone or in combination of two or more kinds. The antioxidant is not particularly limited as long as it is an antioxidant commonly used industrially, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like can be used.

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

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

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

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

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

(3) Color Filter A color filter can be formed from the colored curable resin composition of the present invention. Examples of the method for forming a colored pattern include a photolithography method, an inkjet method, and a printing method. Among these, photolithography is preferred. In the photolithography method, the colored curable resin composition is applied to a substrate, dried to form a colored curable resin composition layer, and the colored curable resin composition layer is exposed to light through a photomask. This is a method of developing. In the photolithography method, by not using a photomask during exposure and/or not developing, a colored coating film that is a cured product of the colored curable resin composition layer can be formed. The colored pattern and colored coating film thus formed are the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited, and can be adjusted as appropriate depending on the purpose, use, etc., and is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, More preferably, it is 0.5 μm or more and 6 μm or less.

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

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

The temperature when performing heat drying is preferably 30°C or higher and 120°C or lower, more preferably 50°C or higher and 110°C or lower. Further, the heating time is preferably 10 seconds or more and 60 minutes or less, and more preferably 30 seconds or more and 30 minutes or less.
When drying under reduced pressure is performed, it is preferably carried out under a pressure of 50 Pa or more and 150 Pa or less and at a temperature range of 20° C. or more and 25° C. or less.
The thickness of the colored curable resin composition is not particularly limited, and may be appropriately selected depending on the thickness of the intended color filter.

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

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

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

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

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

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

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

Synthesis example 1
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.7 parts of 6-aminoundecane (manufactured by Tokyo Chemical Industry Co., Ltd.), 1 part of zinc acetate .3 parts (manufactured by Kanto Kagaku Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 150°C for 3 hours. When 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Kagaku Co., Ltd.) and 1300 parts of water were added to the resulting mixture while keeping the temperature below 20°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the filtered residue was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60° C. to obtain 12 parts of the compound represented by formula (I-1) (yield: 87%).

<Identification of compound I-1>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 699
Exact Mass: 698

Synthesis example 2
8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of 7-aminotridecane (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.0 parts of zinc acetate. 3 parts (manufactured by Kanto Kagaku Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 150°C for 3 hours. When 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Kagaku Co., Ltd.) and 1300 parts of water were added to the resulting mixture while keeping the temperature below 20°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the filtered residue was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60° C. to obtain 12 parts of the compound represented by formula (I-2) (yield 79%).

<Identification of compound I-2>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 755
Exact Mass: 754

Compound (II-2) was obtained from Tokyo Chemical Industry Co., Ltd.

Synthesis example 3
1,6,7,12-tetrachloro-3,4,9,10-perylene dianhydride (manufactured by Combichem Co., Ltd.) 10 parts, 2,6-diisopropylaniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 13 188 parts of propionic acid were added thereto, and the mixture was stirred under reflux for 20 hours. When 50 parts of water was added to the resulting mixture while keeping the temperature below 20°C, an orange precipitate was formed. The mixture containing this orange precipitate was filtered, and the filtered residue was washed with 200 parts of water and 100 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 12 parts of intermediate compound (INT) (yield 75%).

<Identification of compound INT>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+ 847.9
Exact Mass: 848.6

Produced INT 5.0 parts, 4-chlorophenol (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 1.5 parts, 4-tert-butylphenol (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 3.1 parts, potassium carbonate (Kanto 11 parts of Kagaku Co., Ltd.) and 295 parts of N-methylpyrrolidone (Kanto Kagaku Co., Ltd.) were added, and the mixture was stirred at 130°C for 13 hours. When 29 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Kagaku Co., Ltd. SS) and 142 parts of water were added to the resulting mixture while keeping the temperature below 20°C, a dark red precipitate was formed. The mixture containing this dark red precipitate was filtered, and the filtered residue was washed with 300 parts of water and 150 parts of methanol. The obtained residue was dried under reduced pressure at 60° C. to obtain 6.1 parts of the compound represented by formula (II-92) (yield: 81%).

<Identification of compound II-92>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+1237.8
Exact Mass: 1236.8

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

<Example 1>
(1) Preparation of colored composition Colored composition 1 was obtained by mixing each component in the following proportions.
(A) Colorant: 1.3 parts of the compound represented by formula (I-1) (A) Colorant: 2.6 parts of the compound represented by formula (II-2) (B) Resin: Resin B1 solution 54 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts

(2) Preparation of colored curable resin composition Next, each component was mixed in the following proportions to obtain colored curable resin composition 1.
Coloring composition 1 478 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1- (4-Phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: polyether-modified silicone oil (Toray Silicone SH8400: Toray Dow) (manufactured by Corning Corporation) 0.15 part

(3) Preparation of colored coating film Spin coat a colored curable resin composition on a 5 cm square glass substrate (Eagle After coating by the method, prebaking was performed at 100° C. for 3 minutes to form a colored curable resin composition layer. After cooling, the colored curable resin composition layer formed on the substrate was exposed to light at an exposure dose of 80 mJ/cm ² (365 nm standard) using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) in an air atmosphere. ) was irradiated with light. After light irradiation, post-baking was performed in an oven at 230° C. for 30 minutes to obtain a colored coating film.

(4) Heat resistance test The xy chromaticity coordinates (x, y) and Y of the obtained colored coating film were measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). The colored coating film after the measurement was heated in an oven under an air atmosphere at 230° C. for 120 minutes. The xy chromaticity coordinates (x, y) and Y after heating (at 230° C. for 120 minutes) were measured using a colorimeter. Color difference ΔE ^* ab was calculated from the measured values before and after heating by the method described in JIS Z 8730:2009 (7. Color difference calculation method).
In addition, the fluorescence intensity of the colored curable composition film before heating (230°C for 120 minutes) was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.) (excitation side slit 5, fluorescence side slit 10). The measurement was performed using an excitation wavelength of 460 nm). The fluorescence intensity at a wavelength of 610 nm was determined, and the ratio to the fluorescence intensity of Comparative Example 1 before heating was determined. The results are shown in Table 7.
Furthermore, the fluorescence intensity of the colored curable composition film after heating (230°C for 120 minutes) was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.) (excitation side slit 5, fluorescence side slit 10). The measurement was performed using an excitation wavelength of 460 nm). The fluorescence intensity at a wavelength of 610 nm was determined, and the ratio to the fluorescence intensity after heating of Comparative Example 1 was determined. The results are shown in Table 7.

<Example 2>
Colored curable resin composition 2 was obtained in the same manner as in Example 1 except that the colorant was prepared using compound (I-2) instead of compound (I-1). The results are shown in Table 7.

<Example 3>
Colored curable resin composition 3 was obtained in the same manner as in Example 1 except that a colorant was prepared using compound (II-92) instead of compound (II-2). The results are shown in Table 7.

<Example 4>
Colored curable resin composition 4 was obtained in the same manner as in Example 2, except that a colorant was prepared using compound (II-92) instead of compound (II-2). The results are shown in Table 7.

<Example 5>
The same procedure as in Example 3 was carried out, except that compound (I-1) was changed from 1.3 parts to 2.6 parts, and compound (II-92) was changed from 2.6 parts to 1.3 parts. Colored curable resin composition 5 was obtained. The results are shown in Table 7.

<Comparative example 1>
Colored curable resin composition 6 was obtained in the same manner as in Example 1 except that the colorant was prepared without using compound (I-1). The results are shown in Table 7.

<Comparative example 2>
Colored curability was obtained in the same manner as in Example 1, except that the amount of compound (II-2) was changed from 2.6 parts to 3.9 parts, and the colorant was prepared without using compound (I-1). Resin composition 7 was obtained. The results are shown in Table 7.

<Comparative example 3>
Colored curable resin composition 8 was obtained in the same manner as in Example 1, except that the colorant was prepared using Coumarin 545T (manufactured by Tokyo Kasei Co., Ltd.) in place of compound (I-1). The results are shown in Table 7.

<Comparative example 4>
Colored curable resin composition 9 was obtained in the same manner as in Comparative Example 1 except that Compound (II-2) was changed to Compound (II-92). The results are shown in Table 7.

The colored composition of the present invention had a small color difference ΔE ^* ab before and after the heat resistance test, and the fluorescence intensity tended to be high even after the heat resistance test. Therefore, it is understood that the colored composition of the present invention has excellent heat resistance.

Claims (4)

A coloring composition containing a colorant and a resin, wherein the colorant contains a compound represented by the following formula (I) and a fluorescent dye, and the fluorescent dye is represented by the formula (I). This includes compounds that have a different structure from those of other compounds.
The compound having a different structure from the compound represented by formula (I) is a red fluorescent dye,
A colored composition in which the red fluorescent dye is a compound represented by the following formula (II) .

[In formula (I),
R ¹ to R ⁴ each independently represent an alkyl group having 5 to 10 carbon atoms.
R ⁵ to R ¹² each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ]

[In formula (II),
Ar ¹ to Ar ⁶ each independently represent an aryl group which may have a substituent.
R ¹⁵ to R ¹⁸ each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ] Comprising a compound represented by the following formula (I), a fluorescent dye, a resin, a polymerizable compound, a polymerization initiator, and a solvent,
The fluorescent dye includes a compound having a different structure from the compound represented by formula (I),
The compound having a different structure from the compound represented by formula (I) is a red fluorescent dye,
The red fluorescent dye is a colored curable resin composition, which is a compound represented by the following formula (II) .

[In formula (I),
R ¹ to R ⁴ each independently represent an alkyl group having 5 to 10 carbon atoms.
R ⁵ to R ¹² each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ]

[In formula (II),
Ar ¹ to Ar ⁶ each independently represent an aryl group which may have a substituent.
R ¹⁵ to R ¹⁸ each independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, or a nitro group. ] A color filter formed from the colored curable resin composition according to claim 2 . A display device comprising the color filter according to claim 3 .