CN112996860A

Movatterモバイル変換

Info

Publication number: CN112996860A
Application number: CN201980074210.6A
Authority: CN
Inventors: 滨木裕史; 栂井学
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2018-11-13
Filing date: 2019-11-11
Publication date: 2021-06-18
Also published as: KR20210088553A; JP2020079395A; TW202030265A; KR102804446B1; WO2020100781A1; JP7417403B2; TWI810399B

Abstract

Translated fromChinese

本发明的课题在于提供一种耐热性和耐光性优异的着色组合物。本发明涉及一种着色组合物，包含着色剂和树脂，着色剂含有下述式(I)表示的化合物。

The subject of this invention is to provide the coloring composition excellent in heat resistance and light resistance. The present invention relates to a coloring composition comprising a colorant and a resin, wherein the colorant contains a compound represented by the following formula (I).

Description

Coloring composition

Technical Field

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

Background

Colorants are used for displaying colors by reflected light or transmitted light in the fields of fiber materials, liquid crystal display devices, ink jet printers, and the like, for example. As a colorant, a color index (c.i.) solvent green 5 (hereinafter, also simply referred to as "solvent green 5") represented by the following formula is known (non-patent document 1).

On the other hand, in the field of semiconductor electrodes for solar cells, there is described a method for producing an optical semiconductor electrode by immersing a base material of a metal oxide in a solution containing a compound represented by the following formula (patent document 1).

Documents of the prior art

Patent document

Patent document 1: japanese laid-open patent publication No. 10-189065

Non-patent document

Non-patent document 1: color index (The Society of Dyers and Colourists publication)

Disclosure of Invention

In the field of colorants, colorants having more excellent heat resistance and light resistance than solvent green 5 have been sought.

The purpose of the present invention is to provide a coloring composition that exhibits more excellent heat resistance and light resistance than a coloring composition containing solvent green 5.

The invention provides the following colored composition, colored curable resin composition, color filter and display device.

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

[ in the formula (I),

R¹and R²Each independently represents a 2-valent hydrocarbon group having 1 to 20 carbon atoms.

R³～R¹⁰Each independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

[2]According to [1]The coloring composition, wherein R is¹And R²Is an alkanediyl group having 1 to 20 carbon atoms.

[3]According to [1]The coloring composition, wherein R is¹And R²Is a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.

[4]According to [1]The coloring composition, wherein R is¹And R²Is a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.

[5]According to [1]～[4]The coloring composition according to any one of the above, wherein R is³～R¹⁰Is a hydrogen atom.

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

[ in the formula (I),

[7] A color filter comprising the colored curable resin composition according to [6 ].

[8] A display device comprising the color filter according to [7 ].

According to the present invention, a coloring composition excellent in heat resistance and light resistance can be provided.

Detailed Description

(1) Coloring composition

The coloring composition of the present invention comprises a colorant (hereinafter, also referred to as a colorant (a)) and a resin (hereinafter, also referred to as a resin (B)).

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

The colorant (a) may contain a colorant other than the compound (I) (hereinafter, also referred to as a colorant (a 1)).

The colorant (a) may contain 1 or 2 or more colorants (a 1).

The coloring composition may contain a solvent (hereinafter, also referred to as solvent (E)).

The compound (I) may be dispersed in the solvent (E).

< Compound (I) >)

R¹And R²The 2-valent hydrocarbon group has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms. Examples of the 2-valent hydrocarbon group include a 2-valent chain aliphatic hydrocarbon group, a 2-valent alicyclic hydrocarbon group, and a 2-valent aromatic hydrocarbon group.

R¹And R²The 2-valent chained aliphatic hydrocarbon group represented may be saturated or unsaturated. Among them, a 2-valent saturated chain aliphatic hydrocarbon group (hereinafter, also referred to as an alkanediyl group) is preferable. The alkanediyl group may be linear or branched.

As R¹And R²Examples of the linear alkanediyl group include a methylene group, an ethylene group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, a pentane-1, 5-diyl group, a hexane-1, 6-diyl group, a heptane-1, 7-diyl group, an octane-1, 8-diyl group, a nonane-1, 9-diyl group, a decane-1, 10-diyl group, an undecane-1, 11-diyl group, a dodecane-1, 12-diyl group, a tridecane-1, 13-diyl group, a tetradecane-1, 14-diyl group, a pentadecane-1, 15-diyl group, a hexadecane-1, 16-diyl group, a heptadecane-1, 17-diyl group, an octadecane-1, 18-diyl group, a nonadecane-1, 19-diyl group and a eicosane-1, 20-diyl group. Among them, preferred is an alkanediyl group having 1 to 10 carbon atoms, more preferred is an alkanediyl group having 1 to 6 carbon atoms, and still more preferred is a methylene group, an ethylene group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, a pentane-1, 5-diyl group, or a hexane-1, 6-diyl group.

As R¹And R²Examples of the branched alkanediyl group include a 1-methylpropane-1, 3-diyl group, a 2-methylpropane-1, 2-diyl group, a 1-methylbutane-1, 4-diyl group, a 2, 2-dimethylpropane-1, 3-diyl group, a 2-ethylpropane-1, 3-diyl group, a 2-methylpentane-1, 5-diyl group, a 3-methylpentane-1, 5-diyl group, a 2, 3-dimethylpentane-1, 4-diyl group and a 4-methylpentane-1, 2-diyl group. Among these, a branched alkanediyl group having 4 to 10 carbon atoms is preferred, a branched alkanediyl group having 4 to 6 carbon atoms is more preferred, and a 4-methylpentane-1, 2-diyl group is even more preferred.

As R¹And R²Examples of the 2-valent unsaturated chain aliphatic hydrocarbon group include ethylene-1, 2-diyl, prop-1-ene-1, 3-diyl, but-2-ene-1, 4-diyl and pent-3-ene-1, 4-diyl.

As R¹And R²The 2-valent alicyclic hydrocarbon group may be saturated or unsaturated. Among them, a 2-valent saturated alicyclic hydrocarbon group (hereinafter, also referred to as a cycloalkanediyl group) is preferable. The cycloalkanediyl group may be monocyclic or polycyclic. Examples of the monocyclic cycloalkanediyl group include cycloalkanediyl groups such as cyclopropane-1, 2-diyl group, cyclobutane-1, 3-diyl group, cyclopentane-1, 3-diyl group, cyclohexane-1, 4-diyl group, and cyclooctane-1, 5-diyl group. Examples of the polycyclic cycloalkanediyl group include norbornane-1, 4-diyl group, norbornane-2, 5-diyl group, adamantane-1, 5-diyl group, and adamantane-2, 6-diyl group. Among them, cyclohexane-1, 4-diyl is preferable.

As R¹And R²Examples of the 2-valent unsaturated alicyclic hydrocarbon group include cyclohex-2-ene-1, 4-diyl group and the like.

R¹And R²The 2-valent aromatic hydrocarbon group (hereinafter, also referred to as an arene diyl group) may be monocyclic or polycyclic.

Examples of the monocyclic arenediyl group include a benzenediyl group, an alkylphenediyl group, and a dialkylbenzenediyl group. Specific examples thereof include benzene-1, 2-diyl, benzene-1, 3-diyl, benzene-1, 4-diyl, 2-methylbenzene-1, 4-diyl, 3-methylbenzene-1, 4-diyl, 2-methylbenzene-1, 5-diyl, 3-methylbenzene-1, 5-diyl, 4-methylbenzene-1, 5-diyl, 2-ethylbenzene-1, 4-diyl, 3, 5-dimethylbenzene-1, 4-diyl, 3, 5-diethylbenzene-1, 4-diyl, 3-methyl-5-ethylbenzene-1, 4-diyl and 2-methyl-6-ethylbenzene-1, 4-diyl.

Examples of the polycyclic aromatic hydrocarbon diyl group include a naphthalene-1, 5-diyl group, a naphthalene-1, 6-diyl group, a naphthalene-1, 7-diyl group, and a naphthalene-1, 8-diyl group. In addition, R¹And R²The 2-valent aromatic hydrocarbon group may be a group in which 2 or more aromatic hydrocarbon groups are bonded, and [1, 1' -biphenyl group]-4, 4' -diyl and the like.

R¹And R²The aromatic hydrocarbon diyl group is preferably a monocyclic aromatic hydrocarbon diyl group, more preferably a benzene-1, 4-diyl group or a 3, 5-dimethylbenzene group-1, 4-diyl, 2-methylbenzene-1, 4-diyl, 2-ethylbenzene-1, 4-diyl and 3-ethyl-5-methylbenzene-1, 4-diyl.

R¹And R²Each independently preferably a group selected from the group consisting of an alkanediyl group having 1 to 20 carbon atoms, a cycloalkanediyl group having 3 to 20 carbon atoms and an arenediyl group having 6 to 20 carbon atoms, more preferably a group selected from the group consisting of an alkanediyl group having 1 to 10 carbon atoms, a cycloalkanediyl group having 3 to 10 carbon atoms and an arenediyl group having 6 to 10 carbon atoms, still more preferably a group selected from the group consisting of an alkanediyl group having 1 to 6 carbon atoms, a monocyclic cycloalkanediyl group having 5 to 7 carbon atoms, a benzenediyl group, an alkylphenediyl group and a dialkylbenzenediyl group, more preferably a group selected from the group consisting of methylene, ethylene, propane-1, 3-diyl, butane-1, 4-diyl, pentane-1, 5-diyl, 4-methylpentane-1, 2-diyl, cyclohexane-1, 4-diyl, benzene-1, 4-diyl and 3, 5-dimethylbenzene-1, 4-diyl.

R¹And R²Each of the hydrocarbon groups may be independently a group obtained by combining 2 or more hydrocarbon groups, and for example, a group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, or a group obtained by combining an aromatic hydrocarbon group and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group may be used. The total number of carbon atoms of the groups obtained by combining these groups is 20 or less.

R¹And R²May be of the same kind or of different kinds, preferably of the same kind.

As R¹And R²Specific examples of (A) include groups represented by the following formulae. And indicates the bonding site.

As R¹And R²Preferred groups are each independently of the other the formula (A-1) to (A)A-8), (A-14), (B-1) to (B-3), (B-16) to (B-19) or (C-3). From the viewpoint of production, the above-mentioned groups are preferable.

As R³～R¹⁰Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. Among them, fluorine atom and chlorine atom are preferable.

As R³～R¹⁰Examples of the hydrocarbon group having 1 to 40 carbon atoms include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group may be saturated or unsaturated, or may be linear or cyclic.

As R³～R¹⁰Examples of the saturated or unsaturated chain aliphatic hydrocarbon group include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl, tritriacontyl, tetratriacontyl, pentadecanyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and forty-alkyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl, and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, 2-pentenyl and the like; and the like. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, and particularly preferably 1 to 10. Among these, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferable, and a linear or branched alkyl group having 1 to 8 carbon atoms is particularly preferableMethyl or ethyl.

As R³～R¹⁰Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, 2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 2, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, Cycloalkyl groups such as 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptene, cyclooctene, and the like; norbornyl, adamantyl, bicyclo [2.2.2]Octyl, and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, further preferably 4 to 20, particularly preferably 4 to 15, more preferably 5 to 15, and particularly preferably 5 to 10. Among them, most preferred is cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

As R³～R¹⁰The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3, 5-di (tert-butyl) phenyl group, a trimethylphenyl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a, 1-naphthyl, 2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetra-naphthylAnd aromatic hydrocarbon groups such as hydrogen-2-naphthyl, fluorenyl, phenanthryl, anthracyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, and pyrenyl. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.

R³～R¹⁰The hydrocarbon group represented may be a group obtained by combining 2 or more of the above-mentioned hydrocarbon groups, for example, an aromatic hydrocarbon group and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include an aralkyl group such as a benzyl group, a phenethyl group, and a 1-methyl-1-phenylethyl group; an arylalkenyl group such as a phenylvinyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.

R³～R¹⁰The hydrocarbon group represented may be a group obtained by combining 2 or more of the above-mentioned hydrocarbon groups, for example, a group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include an alkyl group to which 1 or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, an adamantylmethyl group, and the like.

The number of carbon atoms of a group obtained by combining 2 or more hydrocarbon groups is preferably 4 to 30, more preferably 4 to 20, still more preferably 4 to 15, and still more preferably 6 to 15.

As R³～R¹⁰Examples of the substituent which may be contained in the hydrocarbon group having 1 to 40 carbon atoms include a halogen atom, a formyl group, a carboxyl group, a formyloxy group, a hydroxyl group, a thiol group, a sulfo group, a sulfamoyl group, a pentafluorosulfanyl group, a carbamoyl group, an amino group, a nitro group, a cyano group and-COR¹²、－COOR¹²、－OCOR¹²、－OR¹²、－SR¹²、－SOR¹²、－SO₂R¹²、－SO₂NHR¹²、－SO₂NR¹²R¹³、－CONHR¹²、－CONR¹²R¹³、－NHR¹²、－NR¹²R¹³、－NHCOR¹²、－NR¹³COR¹²And the like.

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

R¹²And R¹³Each independently represents an alkyl group, a phenyl group or a naphthyl group.

R¹²And R¹³The number of carbon atoms of the alkyl group 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 a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group.

as-COR¹²Examples thereof include acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, 2-ethylhexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, heneicosanoyl and benzoyl.

as-COOR¹²Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenoxycarbonyl and eicosyloxycarbonyl.

as-OCOR¹²Examples thereof include acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, valeryloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy, vinylcarbonyloxy, 2-propenylcarbonyloxyAnd the like.

as-OR¹²Examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, phenoxy and naphthyloxy.

As a-SR¹²Examples thereof include methylsulfanyl, ethylsulfanyl, propylsulfanyl, butylsulfanyl, t-butylsulfanyl, pentylsulfanyl, hexylsulfanyl, (2-ethyl) hexylsulfanyl, heptylsulfanyl, octylsulfanyl, nonylsulfanyl, decylthanyl, undecylsulfanyl, dodecylsulfanyl, eicosylsulfanyl, phenylsulfanyl, and o-tolylsulfanyl.

as-SOR¹²Examples thereof include methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl, pentylsulfinyl, phenylsulfinyl and naphthylsulfinyl groups.

as-SO₂R¹²Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, phenylsulfonyl, naphthylsulfonyl and the like.

as-SO₂NHR¹²Examples thereof include N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl and N-phenylsulfamoyl.

as-SO₂NR¹²R¹³Examples thereof include N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylaminoSulfonyl group, N-di-sec-butylsulfamoyl group, N-di-tert-butylsulfamoyl group, N-butylmethylsulfamoyl group, N-dibutylsulfamoyl group, N-dipentylsulfamoyl group, N-di (1-ethylpropyl) sulfamoyl group, N-dihexylsulfamoyl group, N-di (2-ethyl) hexylsulfamoyl group, N-diheptylsulfamoyl group, N-octylmethylsulfamoyl group, N-dioctylsulfamoyl group, N-dinonylsulfamoyl group, N-decylmethylsulfamoyl group, N-undecylmethylsulfamoyl group, N-dodecylmethylsulfamoyl group, N-eicosylmethylsulfamoyl group, N-phenylmethylsulfamoyl group, N-diphenylsulfamoyl group, etc.

as-CONHR¹²Examples thereof include N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl and N-phenylcarbamoyl.

as-CONR¹²R¹³Examples thereof include N, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, n, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-bis (1-ethylpropyl) carbamoyl group, N-dihexylcarbamoyl group, N-bis (2-ethyl) hexylcarbamoyl group.Acyl, N-diheptylcarbamoyl, N-octylmethylcarbamoyl, N-dioctylcarbamoyl, N-dinonylcarbamoyl, N-decylmethylcarbamoyl, N-undecylmethylcarbamoyl, N-dodecylmethylcarbamoyl, N-eicosylmethyl carbamoyl, N-phenylmethylcarbamoyl, N-diphenylcarbamoyl and the like.

as-NHR¹²Examples thereof include N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N-pentylamino, N-hexylamino, N- (2-ethyl) hexylamino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino and N-phenylamino.

as-NR¹²R¹³Examples thereof include N, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N-dinonylamino group, N-decylmethylamino group, N-undecylmethylamino group, N-dodecylmethylamino group, N, N-eicosylmethyl amino, N-phenylmethyl amino, N-diphenylamino and the like.

as-NHCOR¹²Examples thereof include acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, pentanoylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylaminoAnd the like.

as-NR¹³COR¹²Examples thereof include N-methyl-N-acetylamino and the like.

R³～R¹⁰a-CH which is not a ring and is contained in a C1-40 hydrocarbon group₂May be substituted by-O-, -CO-, -S (O)₂－、－NR^x1-. wherein-CH₂-not by substitution, -COOH and-S (O)₂OH。R^x1Represents 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 a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and an isopentyl group.

As R³～R¹⁰Examples thereof include groups represented by the following formulae. Denotes the bonding site.

As R³～R¹⁰Preferred groups are hydrogen atom, halogen atom, hydroxyl group, nitro group, cyano group, -CH₃And groups represented by the formulae (D-1) to (D-18), (E-1) to (E-27), (F-1) to (F-18) and (G-1) to (G-27). The halogen atom is preferably a chlorine atom or a bromine atom. When these atoms are contained as halogen atoms, the colored pattern or colored coating film formed from the colored curable resin composition tends to have high transmittance at a wavelength of 630nm while exhibiting excellent heat resistance. From a manufacturing point of view, R³～R¹⁰Preferably a hydrogen atom.

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

[ Table 1]

R¹

R²

R³

R⁴

R⁵

R⁶

R⁷

R⁸

R⁹

R¹⁰

I-1

(A-1)

H

I-2

(A-2)

H

I-3

(A-3)

H

I-4

(A-5)

H

I-5

(A-8)

H

I-6

(A-14)

H

I-7

(B-3)

H

I-8

(B-18)

H

I-9

(C-3)

H

I-10

(A-1)

H

(E-9)

H

(E-9)

H

I-11

(A-2)

H

(E-9)

H

(E-9)

H

I-12

(A-3)

H

(E-9)

H

(E-9)

H

I-13

(A-5)

H

(E-9)

H

(E-9)

H

I-14

(A-8)

H

(E-9)

H

(E-9)

H

I-15

(A-14)

H

(E-9)

H

(E-9)

H

I-16

(B-3)

H

(E-9)

H

(E-9)

H

I-17

(B-18)

H

(E-9)

H

(E-9)

H

I-18

(C-3)

H

(E-9)

H

(E-9)

H

I-19

(A-1)

H

(E-9)

H

(E-9)

H

I-20

(A-2)

H

(E-9)

H

(E-9)

H

I-21

(A-3)

H

(E-9)

H

(E-9)

H

I-22

(A-5)

H

(E-9)

H

(E-9)

H

I-23

(A-8)

H

(E-9)

H

(E-9)

H

I-24

(A-14)

H

(E-9)

H

(E-9)

H

I-25

(B-3)

H

(E-9)

H

(E-9)

H

I-26

(B-18)

H

(E-9)

H

(E-9)

H

I-27

(C-3)

H

(E-9)

H

(E-9)

H

I-28

(A-1)

H

(F-14)

H

(F-14)

H

I-29

(A-2)

H

(F-14)

H

(F-14)

H

I-30

(A-3)

H

(F-14)

H

(F-14)

H

I-31

(A-5)

H

(F-14)

H

(F-14)

H

I-32

(A-8)

H

(F-14)

H

(F-14)

H

I-33

(A-14)

H

(F-14)

H

(F-14)

H

I-34

(B-3)

H

(F-14)

H

(F-14)

H

I-35

(B-18)

H

(F-14)

H

(F-14)

H

I-36

(C-3)

H

(F-14)

H

(F-14)

H

I-37

(A-1)

H

(D-14)

H

(D-14)

H

I-38

(A-2)

H

(D-14)

H

(D-14)

H

I-39

(A-3)

H

(D-14)

H

(D-14)

H

I-40

(A-5)

H

(D-14)

H

(D-14)

H

I-41

(A-8)

H

(D-14)

H

(D-14)

H

I-42

(A-14)

H

(D-14)

H

(D-14)

H

I-43

(B-3)

H

(D-14)

H

(D-14)

H

I-44

(B-18)

H

(D-14)

H

(D-14)

H

I-45

(C-3)

H

(D-14)

H

(D-14)

H

[ Table 2]

R¹

R²

R³

R⁴

R⁵

R⁶

R⁷

R⁸

R⁹

R¹⁰

I-46

(A-1)

H

(E-9)

H

(E-9)

H

I-47

(A-2)

H

(E-9)

H

(E-9)

H

I-48

(A-3)

H

(E-9)

H

(E-9)

H

I-49

(A-5)

H

(E-9)

H

(E-9)

H

I-50

(A-8)

H

(E-9)

H

(E-9)

H

I-51

(A-14)

H

(E-9)

H

(E-9)

H

I-52

(B-3)

H

(E-9)

H

(E-9)

H

I-53

(B-18)

H

(E-9)

H

(E-9)

H

I-54

(C-3)

H

(E-9)

H

(E-9)

H

I-55

(A-1)

H

(E-9)

H

(E-9)

H

I-56

(A-2)

H

(E-9)

H

(E-9)

H

I-57

(A-3)

H

(E-9)

H

(E-9)

H

I-58

(A-5)

H

(E-9)

H

(E-9)

H

I-59

(A-8)

H

(E-9)

H

(E-9)

H

I-60

(A-14)

H

(E-9)

H

(E-9)

H

I-61

(B-3)

H

(E-9)

H

(E-9)

H

I-62

(B-18)

H

(E-9)

H

(E-9)

H

I-63

(C-3)

H

(E-9)

H

(E-9)

H

I-64

(A-1)

H

(F-14)

H

(F-14)

H

I-65

(A-2)

H

(F-14)

H

(F-14)

H

I-66

(A-3)

H

(F-14)

H

(F-14)

H

I-67

(A-5)

H

(F-14)

H

(F-14)

H

I-68

(A-8)

H

(F-14)

H

(F-14)

H

I-69

(A-14)

H

(F-14)

H

(F-14)

H

I-70

(B-3)

H

(F-14)

H

(F-14)

H

I-71

(B-18)

H

(F-14)

H

(F-14)

H

I-72

(C-3)

H

(F-14)

H

(F-14)

H

I-73

(A-1)

H

(G-23)

H

(G-23)

H

I-74

(A-2)

H

(G-23)

H

(G-23)

H

I-75

(A-3)

H

(G-23)

H

(G-23)

H

I-76

(A-5)

H

(G-23)

H

(G-23)

H

I-77

(A-8)

H

(G-23)

H

(G-23)

H

I-78

(A-14)

H

(G-23)

H

(G-23)

H

I-79

(B-3)

H

(G-23)

H

(G-23)

H

I-80

(B-18)

H

(G-23)

H

(G-23)

H

I-81

(C-3)

H

(G-23)

H

(G-23)

H

[ Table 3]

R¹

R²

R³

R⁴

R⁵

R⁶

R⁷

R⁸

R⁹

R¹⁰

I-82

A-1

H

Cl

H

Cl

H

I-83

A-2

H

Cl

H

Cl

H

I-B4

A-3

H

Cl

H

Cl

H

I-85

A-5

H

Cl

H

Cl

H

I-86

A-8

H

Cl

H

Cl

H

I-87

A-14

H

Cl

H

Cl

H

I-88

B-3

H

Cl

H

Cl

H

I-89

B-18

H

Cl

H

Cl

H

I-90

C-3

H

Cl

H

Cl

H

I-91

A-1

H

Cl

H

Cl

H

I-92

A-2

H

Cl

H

Cl

H

I-93

A-3

H

Cl

H

Cl

H

I-94

A-5

H

Cl

H

Cl

H

I-95

A-8

H

Cl

H

Cl

H

I-96

A-14

H

Cl

H

Cl

H

I-97

B-3

H

Cl

H

Cl

H

I-98

B-18

H

Cl

H

Cl

H

I-99

C-3

H

Cl

H

Cl

H

I-100

A-1

H

Br

H

Br

H

I-101

A-2

H

Br

H

Br

H

I-102

A-3

H

Br

H

Br

H

I-103

A-5

H

Br

H

Br

H

I-104

A-8

H

Br

H

Br

H

I-105

A-14

H

Br

H

Br

H

I-106

B-3

H

Br

H

Br

H

I-107

B-18

H

Br

H

Br

H

I-108

C-3

H

Br

H

Br

H

I-109

A-1

H

Br

H

Br

H

I-110

A-2

H

Br

H

Br

H

I-111

A-3

H

Br

H

Br

H

I-112

A-5

H

Br

H

Br

H

I-113

A-8

H

Br

H

Br

H

I-114

A-14

H

Br

H

Br

H

I-115

B-3

H

Br

H

Br

H

I-116

B-18

H

Br

H

Br

H

I-117

C-3

H

Br

H

Br

H

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

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

[ in the formula (Ia),

R^1aand R^2aEach independently represents an alkanediyl group having 1 to 20 carbon atoms.

R^3a～R^10aEach independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

As R^1aAnd R^2aExamples of the alkanediyl group represented by the formula (I)¹And R²Examples of the alkanediyl group in the above description are the same.

R^3a～R^10aIs defined with respect to R in formula (I)³～R¹⁰The same definition is applied.

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

In another preferred embodiment of the compound (I) in the present invention, a compound represented by the following formula (Ib) (hereinafter, also referred to as compound (Ib)) may be mentioned.

[ in the formula (Ib),

R^1band R^2bEach independently represents a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.

R^3b～R^10bEach independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

As R^1bAnd R^2bExamples of the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I)¹And R²In the description above, the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.

R^3b～R^10bIs defined with respect to R in formula (I)³～R¹⁰The same definition is applied.

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

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

[ in the formula (Ic),

R^1cand R^2cEach independently represents a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.

R^3c～R^10cEach independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.]

As R^1cAnd R^2cExamples of the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I)¹And R²In the description above, the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.

R^3c～R^10cIs defined with respect to R in formula (I)³～R¹⁰The same definition is applied.

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

The 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 (ca1) in a solvent.

[ in the formula, R³～R¹⁰As defined above.]

[ wherein R represents a C1-20 2-valent hydrocarbon group. ]

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

Examples of the C1-20 2-valent hydrocarbon group represented by R in the formula (ca1) and R in the above-mentioned compound (I)¹And R²The 2-valent hydrocarbon group having 1 to 20 carbon atoms in the description above is exemplified in the same manner.

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

The amount of the compound represented by the formula (ca1) used is usually 1 to 10 moles, preferably 1 to 8 moles, more preferably 1 to 6 moles, and still more preferably 1 to 4 moles, based on 1 mole of the compound represented by the formula (pt 1).

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1, 2-dichlorobenzene; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide.

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

The reaction temperature is usually from-100 ℃ to 300 ℃, preferably from-90 ℃ to 200 ℃, more preferably from-10 ℃ to 150 ℃.

After the reaction is completed, the method for removing compound (I) is not particularly limited, and it can be removed by various known methods. For example, the compound (I) can be removed by distilling off the solvent. After the solvent is distilled off, the obtained residue may be further purified by column chromatography, recrystallization, or the like. After the reaction is completed, the compound (I) can be removed by filtration. 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 by a known analytical method and conditions thereof. Such an analysis method is not particularly limited, and includes an X-ray crystal structure analysis method, a mass spectrometry (LC), an NMR analysis method, an elemental analysis method, and the like. The X-ray crystal structure analysis method can be performed, for example, according to Chemistry of Materials, 2012, volume 24, p.4647-4652.

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

[ in the formula, R^aRepresents an alkanediyl group having 1 to 20 carbon atoms.]

As R^aExamples of the alkanediyl group having 1 to 20 carbon atoms represented by the formula (I)¹And R²Examples of the alkanediyl group having 1 to 20 carbon atoms in the description of (1) are the same as those given above.

Specific examples of the compound (ca1a) include 2-glycine (glycine), 3-aminopropionic acid, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminocaproic acid, 7-aminoheptanoic acid, 8-aminocaprylic acid, 9-aminononanoic acid, 10-aminodecanoic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, 13-aminotridecanoic acid, 14-aminotetradecanoic acid, 15-aminopentadecanoic acid, 16-aminocaproic acid, 17-aminoheptadecanoic acid, 18-aminooctadecanoic acid, 19-aminononadecanoic acid, 20-aminoeicosanoic acid, 2-aminopropionic acid, 2-amino-3-methylbutyric acid, 2-amino-4-methylpentanoic acid, 2-amino-3-methylpentanoic acid, 3-amino-5-methylhexanoic acid (DL-. beta. -homoleucine), and the like.

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

[ in the formula, R^bRepresents a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.]

As R^bExamples of the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I)¹And R²In the description above, the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.

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

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

[ in the formula, R^cRepresents a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.]

As R^cExamples of the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I)¹And R²In the description above, the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.

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

< colorant (A) >)

The content of the compound (I) in the colorant (a) may be, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 5% by mass or more, particularly preferably 10% by mass or more, further preferably 20% by mass or more, further preferably 50% by mass or more, particularly preferably 70% by mass or more, and extremely preferably 90% by mass or more, based on the total amount of the colorant (a). On the other hand, the content of the compound (I) in the colorant (a) is usually less than 100% by mass, for example, may be 99% by mass or less, based on the total amount of the colorant (a).

The content of the compound (I) in the coloring composition may be, for example, 0.1 to 99.9% by mass, preferably 0.5 to 99% by mass, more preferably 1 to 95% by mass, still more preferably 5 to 90% by mass, particularly preferably 10 to 80% by mass, more preferably 15 to 70% by mass, still more preferably 20 to 60% by mass, particularly preferably 25 to 55% by mass, and very preferably 30 to 60% by mass, based on the total amount of solid components in the coloring composition.

In the present specification, the "total amount of solid components in the coloring composition" refers to the total amount of components excluding all solvent components from the coloring composition. The total amount of solid components and the contents of the respective components relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.

The content of the colorant (a) in the coloring composition is usually 0.1 to 99% by mass, for example, 0.1 to 90% by mass, preferably 0.5 to 80% by mass, more preferably 0.7 to 70% by mass, and particularly preferably 1 to 60% by mass, based on the total amount of solid components in the coloring composition.

< colorant (A1) >)

The colorant (a1) may be a dye or a pigment. As The dye, known dyes can be used, and for example, known dyes described in The color index (published by The Society of Dyers and Colourists) and dyeing guidelines (chromo). Further, depending on the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, and the like can be given. These dyes may be used alone or in combination of 2 or more.

Specifically, the following color index (c.i.) number dyes are exemplified.

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: 1. 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

c.i. solvent dyes such as c.i. solvent green 1,3, 4,5, 7, 28, 29, 32, 33, 34, 35,

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, 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: 1. 91, 92, 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 dyes such as c.i. acid green 1,3,5, 6,7,8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50:1, 58, 63, 65, 80, 104, 105, 106, 109 and the like,

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, 256, 236, 229, 237, 242, 244, 245, 247, 238, 248, 250, 257, 275, 260, 251, 293, 268, 274, 251, 268;

c.i. direct dyes such as c.i. direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82,

c.i. disperse yellow 51, 54, 76;

c.i. disperse violet 26, 27;

c.i. disperse dyes such as c.i. disperse blue 1,14, 56, 60, etc.,

c.i. basic red 1, 10;

c.i. basic blue 1,3,5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;

c.i. basic violet 2;

c.i. basic red 9;

c.i. basic dyes such as c.i. basic green 1,

c.i. reactive yellow 2, 76, 116;

c.i. reactive orange 16;

C.I. reactive dyes such as C.I. reactive red 36,

c.i. media yellow 5, 8,10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

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

c.i. intermediate 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. media 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. medium blue 1,2,3, 7,8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84;

c.i. mordant dyes such as c.i. mordant green 1,3, 4,5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53,

c.i. vat dyes such as c.i. vat green 1, and the like.

Further, Lumogen (registered trademark) which is a product of BASF may be mentioned, and Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) FYellow 170 (manufactured by BASF), Lumogen (registered trademark) F Orange 240 (manufactured by BASF), and Lumogen (registered trademark) F Red 305 (manufactured by BASF).

As The pigment, known pigments can be used, and for example, pigments classified as pigments (pigments) in The color index (published by The Society of Dyers and Colourists) can be cited. These may be used alone, or 2 or more of them may be used in combination.

Specifically, there may be mentioned yellow pigments such as c.i. pigment yellow 1,3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231 and the like;

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

red pigments such as 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, 265, 266, 268, 269, 273 and the like;

c.i. pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.;

c.i. pigment violet 1,19, 23, 29, 32, 36, 38 and the like violet pigment;

green pigments such as c.i. pigment green 7, 36, 58, 59, 62, 63;

c.i. brown pigments such as pigment brown 23, 25;

c.i. pigment black 1,7, 31, 32 and the like.

The colorant (a1) may be subjected to, if necessary, rosin treatment, surface treatment using a derivative or the like into which an acidic group or a basic group has been introduced, grafting treatment on the surface of the colorant (a1) by a polymer compound or the like, microparticulation treatment by a sulfuric acid microparticulation method or the like, cleaning treatment by an organic solvent, water or the like for removing impurities, removal treatment by an ion exchange method or the like for removing ionic impurities, or the like. The particle diameter of the colorant (a1) is preferably substantially uniform.

When the colorant (a) contains the compound (I) and the colorant (a1), the lower limit of the content of the compound (I) in the colorant (a) is usually 1 mass% or more, preferably 2 mass% or more, more preferably 10 mass% or more, further preferably 25 mass% or more, and particularly preferably 50 mass% or more, relative to the total amount of the colorant (a). On the other hand, the upper limit of the content of the compound (I) in the colorant (a) is usually less than 100% by mass relative to the total amount of the colorant (a).

When the colorant (a) contains the compound (I) and the colorant (a1), the content of the colorant (a) in the coloring composition is usually 0.1 to 99% by mass, for example, 0.1 to 90% by mass, preferably 0.5 to 80% by mass, more preferably 0.7 to 70% by mass, and particularly preferably 1 to 60% by mass, based on the total amount of solid components in the coloring composition.

When the coloring composition contains the solvent (E), a coloring composition can be prepared by preparing a coloring agent-containing solution containing the coloring agent (a) and the solvent (E) in advance and then using the coloring agent-containing solution. When the colorant (a) is insoluble in the solvent (E), a solution containing the colorant can be prepared by dispersing and mixing the colorant (a) in the solvent (E). The solution containing the colorant may contain a part or all of the solvent (E) contained in the coloring composition.

The content of the solid content in the colorant-containing solution is preferably 0.01 to 99.99% by mass, more preferably 0.1 to 99.9% by mass, even more preferably 0.1 to 99% by mass, even more preferably 1 to 90% by mass, even more preferably 1 to 60% by mass, even more preferably 3 to 50% by mass, particularly preferably 3 to 30% by mass, and extremely preferably 5 to 30% by mass, based on the total amount of the colorant-containing solution.

The content of the colorant (a) in the colorant-containing solution is usually less than 100% by mass, preferably 0.0001 to 99.9999% by mass, more preferably 0.01 to 99% by mass, still more preferably 0.1 to 99% by mass, particularly preferably 1 to 99% by mass, and still more preferably 2 to 99% by mass, of the total amount of solid components in the colorant-containing solution.

In the present specification, the "total amount of solid components in the colorant-containing solution" refers to the total amount of components other than the solvent (E) in the colorant-containing solution. The total amount of solid components and the contents of the respective components relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.

The colorant (a) can be dispersed by a dispersing agent to obtain a state in which the colorant (a) is uniformly dispersed in a solution containing the colorant. The colorant (a) may be dispersed alone or in combination of two or more.

The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamide, acrylic and other surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by shin-Etsu chemical Co., Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by AJISPER Fine chemical Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie), BYK (registered trademark) (manufactured by BYK-Chemie).

When a dispersant is used for the preparation of the colorant-containing solution, the amount of the dispersant (solid content) used is usually 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, more preferably 100 parts by mass or less, still more preferably 5 to 100 parts by mass, and particularly preferably 5 to 50 parts by mass, per 100 parts by mass of the colorant (a). When the amount of the dispersant used is within the above range, a more uniformly dispersed solution containing the colorant tends to be obtained.

< resin (B) >

The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least 1 monomer (hereinafter, sometimes referred to as "monomer (a)") selected from an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride.

The resin (B) is preferably a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (B)") and another structural unit.

Examples of the other structural units include structural units derived from a monomer copolymerizable with the monomer (a) (which is different from the monomer (a) and the monomer (b) and may be referred to as "monomer (c)" hereinafter), structural units having an ethylenically unsaturated bond, and the like.

Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;

unsaturated dicarboxylic acids such as 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, dimethyltetrahydrophthalic acid, and 1, 4-cyclohexene dicarboxylic acid;

carboxyl group-containing bicyclic unsaturated compounds such as 5-norbornene-2, 3-dicarboxylic acid methyl ester, 5-carboxybicyclo [2.2.1] hept-2-ene, 5, 6-dicarboxybicyclo [2.2.1] hept-2-ene, 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 methylfumaric acid;

unsaturated mono [ (meth) acryloyloxyalkyl ] esters of 2-or more-membered polycarboxylic acids such as succinic acid mono [ 2- (meth) acryloyloxyethyl ester ] and phthalic acid mono [ 2- (meth) acryloyloxyethyl ester ];

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

Among them, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained 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 1 selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.

Examples of the monomer (b) include a monomer having an oxirane group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b 1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b 2)"), a monomer having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b 3)"), and the like.

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

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

Specific examples of the monomer (b 1-1) include glycidyl (meth) acrylate, β -methylglycidyl (meth) acrylate, β -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, α -methylvinylbenzyl glycidyl ether, 2, 3-bis (glycidoxymethyl) styrene, 2, 4-bis (glycidoxymethyl) styrene, 2, 5-bis (glycidoxymethyl) styrene, 2, 6-bis (glycidoxymethyl) styrene, 2,3, 4-tris (glycidoxymethyl) styrene, 2,3, 5-tris (glycidoxymethyl) styrene, 2,3, 6-tris (glycidoxymethyl) styrene, 3,4, 5-tris (glycidoxymethyl) styrene and 2,4, 6-tris (glycidoxymethyl) styrene, and the like.

Examples of the monomer (b 1-2) include vinylcyclohexene monooxide, 1, 2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000 (manufactured by Daicel Co., Ltd.), (3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer (registered trademark) A400 (manufactured by Daicel Co., Ltd.), (3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer (registered trademark) M100 (manufactured by Daicel Co., Ltd.)), compounds represented by the formula (BI), and compounds represented by the formula (BII).

[ formula (BI) and formula (BII) wherein R^aAnd R^bEach independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group.

X^aAnd X^bEach independently represents a single bond, [ R ]^c－、*－R^c－O－、*－R^c-S-or R^c－NH－。

R^cRepresents an alkanediyl group having 1 to 6 carbon atoms.

Denotes the bonding site to O. ]

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

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

As R^aAnd R^bPreferred examples thereof include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferred examples thereof include a hydrogen atom and a methyl group.

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

As X^aAnd X^bPreferred examples thereof include a single bond, methylene, ethylene and-CH₂-O-and-CH₂CH₂More preferably, the group-O-includes a single bond and-CH₂CH₂-O- (. indicates a bonding site to O.).

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

The compound represented by the formula (BII) includes compounds represented by any one of the formulae (BII-1) to (BII-15), and the like, and among them, compounds represented by the formulae (BII-1), (BII-3), (BII-5), (BII-7), the formula (BII-9), and the formulae (BII-11) to (BII-15) are preferable, and compounds represented by the formulae (BII-1), (BII-7), the formula (BII-9), and the formula (BII-15) are more preferable.

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

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-methacryloxymethyloxetane, 3-methyl-3-acryloxymethyloxetane, 3-ethyl-3-methacryloxymethyloxetane, 3-ethyl-3-acryloxymethyloxetane, 3-methyl-3-methacryloxyethyloxetane, 3-methyl-3-acryloxyethyloxetane, 3-ethyl-3-methacryloxyethyloxetane, and 3-ethyl-3-acryloxyethyloxetane.

As the monomer (b3), a monomer having a tetrahydrofuranyl group and a (meth) acryloyloxy group is more preferable.

Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V #150, manufactured by Osaka Organischen chemical industries, Ltd.), tetrahydrofurfuryl methacrylate, and the like.

The monomer (b) is preferably the monomer (b1) in view of enabling the obtained color filter to have higher reliability such as heat resistance, chemical resistance and the like. Further, the monomer (b 1-2) is more preferable in terms of excellent storage stability of the coloring composition.

Examples of the monomer (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and tricyclo [5.2.1.0 ] meth) acrylate^2,6]Decan-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decan-9-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decen-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)^2,6](meth) acrylates such as decen-9-yl ester, dicyclopentyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, and benzyl (meth) acrylate;

hydroxyl group-containing (meth) acrylates 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-bis (hydroxymethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-bis (2' -hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-dimethoxybicyclo [ 2.1] hept-2-ene, 5, 6-bis (2.1) hept-2-ene, 5-hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxyhept-2-ene, 5-hydroxybicyclo [2.2.1] hept-2-ene, 5-2.1 ] hept-2, Bicyclic unsaturated compounds such as 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonybicyclo [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 (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene;

dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-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; vinyl group-containing amides such as (meth) acrylamide; esters such as vinyl acetate; dienes such as 1, 3-butadiene, isoprene and 2, 3-dimethyl-1, 3-butadiene.

Among them, styrene, vinyltoluene, and tricyclo [5.2.1.0 ] meth (acrylic acid) are preferable from the viewpoint of copolymerization reactivity and heat resistance^2,6]Decan-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)²_,⁶]Decan-9-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decen-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1]Hept-2-ene, benzyl (meth) acrylate, and the like.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group. The resin having such a structural unit can be obtained by adding a monomer having a group reactive with the groups of the monomer (a) and the monomer (b) and an ethylenically unsaturated bond to a polymer having a structural unit derived from the monomer (a) and the monomer (b).

Examples of such a structural unit include a structural unit obtained by adding glycidyl (meth) acrylate to a (meth) acrylic acid unit, a structural unit obtained by adding 2-hydroxyethyl (meth) acrylate to a maleic anhydride unit, and a structural unit obtained by adding (meth) acrylic acid to a glycidyl (meth) acrylate unit. When these structural units have a hydroxyl group, a structural unit to which a carboxylic anhydride is further added may be mentioned as a structural unit having an ethylenically unsaturated bond.

The polymer having a structural unit derived from the monomer (a) can be produced, for example, by polymerizing a monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, the solvent and the like are not particularly limited, and those generally used in the art can be used. Examples of the polymerization initiator include azo compounds (e.g., 2 '-azobisisobutyronitrile, 2' -azobis (2, 4-dimethylvaleronitrile), and organic peroxides (e.g., benzoyl peroxide), and any solvent may be used as long as it dissolves the monomers.

The polymer obtained may be used as it is in the solution after the reaction, may be used as it is, may be used as a concentrated or diluted solution, or may be used as it is taken out as a solid (powder) by a method such as reprecipitation.

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

Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5, 6-tetrahydrophthalic anhydride, 1,2,3, 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5, 6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride.

Specific examples of the resin (B) include 3, 4-epoxycyclohexylmethyl (meth) acrylate/(meth) acrylic acid copolymer, and 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/(meth) acrylic acid benzyl esterEster/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/styrene/(meth) acrylic acid copolymer, and 3, 4-epoxy tricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid 2-ethylhexyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid tricyclo [5.2.1.0^2,6]Decenyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyloxetane/(meth) acrylic acid/styrene copolymer, benzyl (meth) acrylate/(meth) acrylic acid copolymer, styrene/(meth) acrylic acid copolymer, and resins described in each of Japanese patent application laid-open Nos. 9-106071, 2004-29518 and 2004-361455.

Among these, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (B).

The resin (B) may be used in combination of 2 or more, and in this case, the resin (B) preferably contains at least one member selected from the group consisting of 3, 4-epoxytricyclo [5.2.1.0 ] s of (meth) acrylic acid^2,6]Decyl ester/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]1 or more of decyl ester/(meth) acrylic acid 2-ethylhexyl ester copolymer.

The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 1000 to 100000, more preferably 1000 to 50000, still more preferably 1000 to 30000, and particularly preferably 3000 to 30000.

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

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

The content of the resin (B) in the coloring composition may be, for example, 0.1 to 99.9% by mass, preferably 0.5 to 99% by mass, more preferably 1 to 95% by mass, still more preferably 2 to 90% by mass, particularly preferably 3 to 80% by mass, still more preferably 5 to 70% by mass, still more preferably 7 to 60% by mass, particularly preferably 10 to 50% by mass, and very preferably 15 to 40% by mass, based on the total amount of solid components in the coloring composition.

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

The content of the resin (B) in the colorant-containing solution may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 1 to 500 parts by mass, particularly preferably 5 to 200 parts by mass, and still more preferably 10 to 100 parts by mass, per 100 parts by mass of the colorant (a).

< embodiment 1 >

The coloring composition of embodiment 1 includes a colorant (a) and a resin (B), and the colorant (a) contains a compound represented by the following formula (Ia).

[ in the formula (Ia), R^1a～R^10aThe definitions of (a) are the same as those described above.]

Examples and preferred ranges of the content of the compound (Ia) in the colorant (a) are the same as those of the content of the compound (I) in the colorant (a) described above.

< embodiment 2 >

The coloring composition of embodiment 2 includes a colorant (a) and a resin (B), and the colorant (a) contains a compound represented by the following formula (Ib).

[ in the formula (Ib), R^1b～R^10bThe definitions of (a) are the same as those described above.]

Examples and preferred ranges of the content of the compound (Ib) in the colorant (a) are the same as those of the content of the compound (I) in the colorant (a) described above.

< embodiment 3 >

The coloring composition of embodiment 3 includes a colorant (a) and a resin (B), and the colorant (a) contains the compound (Ic).

[ in the formula (Ic), R^1c～R^10cThe definitions of (a) are the same as those described above.]

Examples and preferred ranges of the content of the compound (Ic) in the colorant (a) are the same as those of the content of the compound (I) in the colorant (a) described above.

(2) Colored curable resin composition

The colored curable resin composition contains a compound (I), a resin (B) (hereinafter, these are also collectively referred to as a colorant (a)), a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)), and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).

The colored curable resin composition may further contain 1 kind selected from a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)), an antioxidant (hereinafter, sometimes referred to as an antioxidant (G)), and a solvent (E).

The content of the solid content in the colored composition contained in the colored curable resin composition is not particularly limited since it is appropriately adjusted according to the chromaticity, brightness, film thickness, and the like required for curing the colored curable resin composition, and may be, for example, 1 to 99% by mass, preferably 1 to 90% by mass, more preferably 2 to 80% by mass, further preferably 3 to 70% by mass, particularly preferably 4 to 60% by mass, more preferably 5 to 50% by mass, particularly preferably 6 to 40% by mass, and extremely preferably 7 to 30% by mass, based on the total amount of the solid content in the colored curable resin composition.

The content of the colorant (a) in the colored curable resin composition is not particularly limited since it is appropriately adjusted according to the chromaticity, brightness, film thickness, and the like required for curing the colored curable resin composition, and may be, for example, 0.1 to 99% by mass, preferably 1 to 90% by mass, more preferably 2 to 80% by mass, further preferably 3 to 70% by mass, particularly preferably 4 to 60% by mass, more preferably 5 to 50% by mass, particularly preferably 6 to 40% by mass, and extremely preferably 7 to 30% by mass, of the total amount of solid components in the colored curable resin composition.

In the present specification, the "total amount of solid components in the colored curable resin composition" refers to the total amount of components excluding the solvent (E) from the colored curable resin composition. The total amount of the solid components and the contents of the respective components relative to the total amount can be measured by a known analysis method such as liquid chromatography or gas chromatography. The content of the solid content 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 to 99.9% by mass, more preferably 0.1% by mass to 99% by mass, particularly preferably 1% by mass to 60% by mass, more preferably 3% by mass to 50% by mass, further preferably 3% by mass to 30% by mass, and particularly preferably 5% by mass to 30% by mass, based on the total amount of the colored curable resin composition.

< polymerizable Compound (C) >)

The polymerizable compound (C) is a compound which can be polymerized by an active radical and/or an acid generated by the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferably a (meth) acrylate compound.

Examples of the polymerizable compound having 1 ethylenically unsaturated bond include nonylphenylcarbinol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomer (a), monomer (b), and monomer (c).

Examples of the polymerizable compound having 2 ethylenically unsaturated bonds include 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol a, and 3-methylpentanediol di (meth) acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane 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, caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate Esters and the like are preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 to 4000, more preferably 50 to 3500, still more preferably 50 to 3000, particularly preferably 150 to 2900, and particularly preferably 250 to 1500.

The content of the polymerizable compound (C) in the colored curable resin composition may be, for example, 1 to 99% by mass, preferably 2 to 90% by mass, more preferably 3 to 80% by mass, still more preferably 4 to 70% by mass, particularly preferably 5 to 60% by mass, still more preferably 6 to 50% by mass, and particularly preferably 7 to 40% by mass, based on the total amount of solid components.

< polymerization initiator (D) >)

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

Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a bisimidazole compound, a triazine compound, and an acylphosphine oxide compound.

Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-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-dioxopentylmethyloxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopentylpropane-1-imine and N-benzoyloxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopentylpropane-1-one-2-imine, etc. Further, as the O-acyloxime compound, commercially available products such as Irgacure OXE01, OXE02 (both of which are manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) can be used. Among them, as the O-acyloxime compound, at least 1 selected from the group consisting of N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine is more preferable.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, and 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [ 4- (4-morpholino) phenyl ] butan-1-one. As the alkylphenone compound, commercially available products such as Irgacure 369, 907 and 379 (all of which are manufactured by BASF) can be used.

Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [ 4- (2-hydroxyethoxy) phenyl ] propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α -diethoxyacetophenone and benzildimethylketal.

Examples of the biimidazole compound include 2,2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetraphenylbiimidazole, 2' -bis (2, 3-dichlorophenyl) -4, 4 ', 5, 5' -tetraphenylbiimidazole (see, for example, japanese patent application laid-open No. 6-75372, japanese patent application laid-open No. 6-75373, etc.), 2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetrakis (alkoxyphenyl) biimidazole, 2' -bis (2-chlorophenyl) -4, 4 ', 5, 5' -tetrakis (dialkoxyphenyl) biimidazole, 2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetrakis (trialkoxyphenyl) biimidazole (see, for example, japanese patent publication No. 48-38403, japanese patent publication No. 62-174204, etc.), and 4, 4', and biimidazole compounds in which the phenyl group at the 5, 5' -position is substituted with a carbonylalkoxy group (see, for example, Japanese patent laid-open No. 7-10913).

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

Examples of the acylphosphine oxide compound include 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and the like. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.

Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3 ', 4,4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone and 2,4, 6-trimethylbenzophenone; quinone compounds such as 9, 10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, titanocene compounds, and the like.

These are preferably used in combination with a polymerization initiation aid (D1) (particularly an amine) described later.

The polymerization initiator (D) is preferably a polymerization initiator containing at least 1 selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a bisimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

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

< polymerization initiation assistant (D1) >)

The polymerization initiation aid (D1) is a compound or sensitizer for promoting polymerization of a polymerizable compound whose polymerization is initiated by a polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N-dimethyl-p-toluidine, 4 '-bis (dimethylamino) benzophenone (commonly known as michelson), 4' -bis (diethylamino) benzophenone, and 4,4 '-bis (ethylmethylamino) benzophenone, and 4, 4' -bis (diethylamino) benzophenone is preferable. As the amine compound, a commercially available compound such as EAB-F (manufactured by UK chemical Co., Ltd.) can be used.

Examples of the alkoxyanthracene compound include 9, 10-dimethoxyanthracene, 2-ethyl-9, 10-dimethoxyanthracene, 9, 10-diethoxyanthracene, 2-ethyl-9, 10-diethoxyanthracene, 9, 10-dibutoxyanthracene, 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 the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylsulfanylacetic acid, N-naphthylglycine, and naphthyloxyacetic acid.

When the polymerization initiator aid (D1) is used, the content thereof may be, for example, 0.01 to 40% by mass, preferably 0.1 to 30% by mass, based on the total amount of the resin (B) and the polymerizable compound (C).

< solvent (E) >

Examples of the solvent (E) include an ester solvent (a solvent containing-COO-and not containing-O-in the molecule), an ether solvent (a solvent containing-O-and not containing-COO-in the molecule), an ether ester solvent (a solvent containing-COO-and not containing-COO-in the molecule), a ketone solvent (a solvent containing-CO-and not containing-COO-in the molecule), an alcohol solvent (a solvent containing OH and not containing-O-, -CO-, and-COO-, a solvent), an aromatic hydrocarbon solvent, an amide solvent, and dimethyl sulfoxide.

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

Examples of the ether solvent 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-di-n

Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

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

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

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-dimethylacetamide, and N-methylpyrrolidone.

These solvents may be used in combination of 2 or more.

The content of the solvent (E) is usually 99.99% by mass or less, preferably 0.1% by mass to 99.9% by mass, more preferably 1% by mass to 99.9% by mass, still more preferably 10% by mass to 99% by mass, particularly preferably 40% by mass to 99% by mass, more preferably 50% by mass to 97% by mass, particularly preferably 70% by mass to 97% by mass, and very preferably 75% by mass to 95% by mass, based on the total amount of the colored curable resin composition.

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

The content of the solid content in the colorant-containing solution may be, for example, 0.01 to 99.99% by mass, preferably 0.1 to 99.9% by mass, more preferably 0.1 to 99% by mass, still more preferably 1 to 90% by mass, still more preferably 1 to 60% by mass, still more preferably 3 to 50% by mass, particularly preferably 3 to 40% by mass, and extremely preferably 5 to 35% by mass, based on the total amount of the colorant-containing solution.

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

When the colorant-containing solution is prepared by dispersing all or a part of the compound (I) in all or a part of the solvent (E), the dispersion stability of the colorant-containing solution can be further improved by previously containing all or a part of the resin (B). The content of the resin (B) in the colorant-containing solution may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 1 to 500 parts by mass, particularly preferably 5 to 200 parts by mass, and more preferably 10 to 100 parts by mass, based on 100 parts by mass of the compound (I).

The compound (I) may be subjected to, if necessary, rosin treatment, surface treatment using a derivative or the like into which an acidic group or a basic group has been introduced, grafting treatment on the surface of the compound (I) with a polymer compound or the like, micronization treatment by a sulfuric acid micronization method or the like, cleaning treatment by an organic solvent, water or the like for removing impurities, removal treatment by an ion exchange method or the like for ionic impurities, or the like. The particle size of the compound (I) is preferably substantially uniform.

The compound (I) can be dispersed by a dispersing agent to obtain a state in which the compound (I) is uniformly dispersed in a solution containing a colorant. The compound (I) may be dispersed individually or in combination of two or more.

The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamide, acrylic and other surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by shin-Etsu chemical industry Co., Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by AJIAOSU Fine chemical Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and the like.

When the dispersant is used, the amount of the dispersant (solid content) used is 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, more preferably 100 parts by mass or less, further preferably 5 to 100 parts by mass, and particularly preferably 5 to 50 parts by mass, relative to 100 parts by mass of the compound (I). When the amount of the dispersant used is within the above range, a more uniformly dispersed solution containing the colorant 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 a silicone surfactant, a fluorine surfactant, and a silicone surfactant having a fluorine atom. These may have a polymerizable group in a side chain.

Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Dow Corning corporation), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by shin-Etsu chemical industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by MONTMEIVE PERFURIACE MATLS. MATPANI contract Co., Ltd.) may be mentioned.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, examples thereof include FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC (Co., Ltd.), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi electro chemical Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Nitron (Co., Ltd.), and E5844 (manufactured by King Kogyo chemical Co., Ltd.).

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

When the leveling agent (F) is contained, the content thereof is usually 0.0005 to 5% by mass, preferably 0.001 to 1% by mass, more preferably 0.001 to 0.5% by mass, still more preferably 0.002 to 0.2% by mass or less, and particularly preferably 0.005 to 0.1% by mass, based on the total amount of the colored curable resin composition. 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 and light resistance of the colorant, the antioxidant (G) is preferably used alone or in combination of 2 or more. The antioxidant is not particularly limited as long as it is an industrially commonly used antioxidant, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, and the like can be used.

Examples of the above-mentioned phenolic antioxidants include Irganox 1010(Irganox 1010: pentaerythritol tetrakis [ 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF), Irganox 1076(Irganox 1076: octadecyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate, manufactured by BASF), Irganox 1330(Irganox 1330:3,3 ', 5,5 ' -hexa-t-butyl-a, a ' - (mesitylene-2, 4, 6-triyl) tri-p-cresol, manufactured by BASF), Irganox 3114(Irganox 3114:1,3, 5-tris (3, 5-di-t-butyl-4-hydroxybenzyl) -1, 3, 5-triazine-2, 4,6(1H, 3H, 5H) -trione, manufactured by BASF), Irganox 3790(Irganox 3790:1,3, 5-tri-t-butyl-4-hydroxybenzyl) -1, 3, 5-triazine-2, 4,6(1H, 5H) -trione, manufactured by BASF), 3, 5-triazine-2, 4,6(1H, 3H, 5H) -trione, manufactured by BASF), Irganox 1035(Irganox 1035: thiodiethylene bis [ 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF), Irganox1135 (Irganox1135: phenylalanic acid, 3, 5-bis (1, 1-dimethylethyl) -4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF), Irganox 1520L (Irganox 1520L:4, 6-bis (octylthiomethyl) -o-cresol, manufactured by BASF), Irganox 3125(Irganox 3125, manufactured by BASF), Irganox 565(Irganox 565:2, 4-bis (n-octylthio) -6- (4-hydroxy 3 ', 5' -di-tert-butylanilino) -1, 3, 5-triazine, manufactured by BASF), ADK B80 (ADK B80: ADK 3-bis (ADK 3-5-hydroxy propionyloxy) -1, 3, 5-bis (ADB 3-5-hydroxy-phenyl-5-methyl-o-phenyl-5, 1-dimethylethyl) -2, 4,8, 10-tetraoxaspiro (5,5) undecane (manufactured by ADEKA), Sumilizer BHT (Sumilizer BHT, manufactured by Sumitomo chemical Co., Ltd.), Sumilizer GA-80 (Sumilizer GA-80, manufactured by Sumitomo chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, manufactured by Sumitomo chemical Co., Ltd.), Cyanox 1790 (manufactured by Sitech)) and vitamin E (manufactured by Eisai).

Examples of the phosphorus-based antioxidant include Irgafos 168(Irgafos 168: tris (2, 4-di-t-butylphenyl) phosphite, manufactured by BASF), Irgafos 12(Irgafos 12: tris [ 2- [ [2,4,8, 10-tetra-t-butylbenzo [ d, f ] [1,3,2] dioxaphosphin-6-yl ] oxy ] ethyl ] amine, manufactured by BASF), Irgafos 38(Irgafos 38: bis (2, 4-bis (1, 1-dimethylethyl) -6-methylphenyl) ethyl phosphite, manufactured by BASF), ADK STAB 329K (manufactured by ADEKA), ADK STAB PEP36 (manufactured by ADEKA), ADSTAB PEP-8 ((manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston618 (GE, manufactured by Weston618, manufactured by Wemilstin), Wemilstin 626 (manufactured by Westin G619, manufactured by Westin 626, manufactured by Westin GK-6-hydroxy propoxy 3- (GP-3, manufactured by Westin) (manufactured by Westin) and U.3- (3-butyl) propoxy G, manufactured by BASF) -2, 4,8, 10-tetra-tert-butyldibenzo [ d, f ] [1.3.2] dioxaphosphepin) (manufactured by Sumitomo chemical Co., Ltd.), and the like.

Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and β -alkylmercaptopropionate compounds of polyhydric alcohols such as tetrakis [ methylene (3-dodecylthio) propionate ] methane.

< other ingredients >

The colored curable resin composition of the present invention may contain additives known in the art, such as a filler, another polymer compound, an adhesion promoter, a light stabilizer, and a chain transfer agent, as required.

Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-thioalkylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, N-glycidyloxy-3-epoxysilane, and the like, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.

< method for producing colored curable resin composition >

The colored curable resin composition can be prepared, for example, by mixing the colorant (a), the resin (B), the solvent (E), and the leveling agent (F), and further mixing the mixture with the polymerizable compound (C), the polymerization initiator (D), the polymerization initiation aid (D1), and other components when the pattern is formed by photolithography.

The pigment is preferably mixed with a part or all of the solvent (E) in advance, and dispersed by a bead mill until the average particle diameter of the pigment becomes about 0.2 μm or less. In this case, a part or all of the pigment dispersant and the resin (B) may be blended as necessary. The remaining components are mixed in the thus obtained pigment dispersion liquid so as to have a predetermined concentration, whereby the target colored curable resin composition can be prepared.

The dyes may be dissolved in a part or all of the solvent (E) separately in advance to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

The mixed colored curable resin composition is preferably filtered through a filter having a pore size of about 0.1 to 10 μm.

(3) Color filter

The color filter can be formed from the colored curable resin composition of the present invention. Examples of a method for forming a colored pattern include a photolithography method, an ink jet method, a printing method, and the like. Among them, photolithography is preferable. The photolithography method is a method in which the colored curable composition is applied to a substrate and dried to form a colored curable composition layer, and the colored curable composition layer is exposed to light through a photomask and developed. In the photolithography method, a colored coating film which is a cured product of the colored curable resin composition layer can be formed without using a photomask and/or without performing development at the time of exposure. The colored pattern and the colored coating film formed in this way 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 suitably adjusted according to the purpose, application, and the like, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

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

The formation of each color pixel by photolithography can be performed by using a known or conventional apparatus and conditions. For example, the following can be used.

First, a substrate is coated with the colored curable resin composition, and is dried by heating (prebaking) and/or drying under reduced pressure to remove volatile components such as a solvent and dry the composition, thereby obtaining a smooth colored curable resin composition layer.

Examples of the coating method include a spin coating method, a slit coating method, and a slit/spin coating method.

The temperature for heating and drying is preferably 30 to 120 ℃, more preferably 50 to 110 ℃. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.

When the drying is carried out under reduced pressure, the drying is preferably carried out under a pressure of 50 to 150Pa and at a temperature of 20 to 25 ℃.

The film thickness of the colored curable resin composition is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.

Next, the colored curable resin composition layer is exposed to light through a photomask for forming a target colored pattern. In order to uniformly irradiate parallel light rays to the entire exposure surface and perform precise alignment of the photomask and the substrate on which the colored curable composition layer is formed, an exposure apparatus such as a mask aligner or a stepper is preferably used.

The light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350nm may be cut off using a filter that cuts off the wavelength region, or light near 436nm, near 408nm, or near 365nm may be selectively extracted using a band-pass filter that extracts these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like can be given.

The exposed colored curable composition layer is brought into contact with a developer to develop the layer, thereby forming a colored pattern on the substrate. The unexposed portion of the colored curable composition layer is dissolved in a developing solution and removed by development.

As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of the basic compound in the aqueous solution may be, for example, 0.01 to 10% by mass. Further, the developer may contain a surfactant.

The developing method may be any of a paddle method, a dipping method, a spraying method, and the like. Further, the substrate can be inclined at an arbitrary angle during development.

The developed substrate is preferably washed with water.

Further preferably, the obtained colored pattern is subjected to post-baking.

(4) Display device

The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, or the like) and a solid-state imaging element, and particularly as a color filter used in an organic EL device.

Examples

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples, and it goes without saying that the present invention can be carried out with appropriate modifications within a range that can be adapted to the gist described above and below, and these are included in 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 by Agilent, MASS; model LC/MSD6130 by Agilent).

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC under the following conditions.

HLC-8120 GPC (manufactured by Tosoh corporation)

The column is TSK-GELG 2000HXL

Column temperature 40 deg.C

Solvent tetrahydrofuran

Flow rate 1.0 mL/min

The solid content concentration of the analysis sample is 0.001-0.01 mass%

The injection amount was 50. mu.L

Detector RI

Calibration standard materials 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) to the number average molecular weight (Mn) in terms of polystyrene obtained above was defined as the degree of dispersion.

Synthesis example 1

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industry Co., Ltd.), 3.8 parts of glycine (manufactured by Tokyo chemical industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industry Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industry Co., Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 7 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 at 60 ℃ under reduced pressure to obtain 9.1 parts (yield: 88%) of a compound represented by formula (I-1) (also referred to as compound I-1).

< identification of Compound I-1 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－505

Accurate mass 506

Synthesis example 2

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 4.6 parts of beta-alanine (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industries, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto and stirred at 150 ℃ for 14 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 8.7 parts (yield: 80%) of a compound represented by formula (I-2) (also referred to as compound I-2).

< identification of Compound I-2 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－533

Accurate mass 534

Synthesis example 3

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 5.3 parts of 4-aminobutyric acid (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industries, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto and stirred at 150 ℃ for 14 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 8.8 parts (yield: 77%) of a compound represented by formula (I-3) (also referred to as compound I-3).

< identification of Compound I-3 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－561

Accurate mass 562

Synthesis example 4

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 6.0 parts of 5-aminopentanoic acid (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industries, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto and stirred at 150 ℃ for 14 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 8.8 parts (yield: 77%) of a compound represented by formula (I-4) (also referred to as compound I-4).

< identification of Compound I-4 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－589

Accurate mass 590

Synthesis example 5

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 6.7 parts of 6-aminocaproic acid (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industries, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto and stirred at 150 ℃ for 14 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 9.5 parts (yield: 75%) of a compound represented by formula (I-5) (also referred to as compound I-5).

< identification of Compound I-5 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－617

Accurate mass 618

Synthesis example 6

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industry Co., Ltd.), 7.4 parts of DL- β -homoleucine (manufactured by Tokyo chemical industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industry Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industry Co., Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 14 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 10 parts (yield: 78%) of a compound represented by formula (I-6) (also referred to as compound I-6).

< identification of Compound I-6 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－645

Accurate mass 646

Synthesis example 7

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 7.0 parts of 4-aminobenzoic acid (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industries, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 22 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 11 parts (yield: 89%) of the compound represented by the formula (I-7) (also referred to as compound I-7).

< identification of Compound I-7 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－629

Accurate mass 630

Synthesis example 8

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industry Co., Ltd.), 8.4 parts of 4-amino-3, 5-dimethylbenzoic acid (synthesized according to the method described in European Journal of medicinal Chemistry2014, 78.236), 1.3 parts of zinc acetate (manufactured by Kanto chemical Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industry Co., Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 22 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 13 parts (yield: 90%) of a compound represented by formula (I-8) (also referred to as compound I-8).

< identification of Compound I-8 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－685

Accurate mass 686

Synthesis example 9

8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 7.3 parts of trans/cis-4-aminocyclohexanecarboxylic acid (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto Chemicals, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 22 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the 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 ℃ to obtain 9.8 parts (yield: 75%) of a compound represented by formula (I-9) (also referred to as compound I-9).

< identification of Compound I-9 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－641

Accurate mass 642

Synthesis example 10

The same procedures as in synthesis example 1 were repeated except that 8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride in synthesis example 1 was changed to 3.4 parts of 1,6,7, 12-tetrachloro-3, 4,9, 10-perylenetetracarboxylic dianhydride (manufactured by ComBi Blocks), thereby obtaining 2.9 parts of a compound represented by formula (I-91) (also referred to as compound I-91) (yield: 70%).

< identification of Compound I-91 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－641

Accurate mass 642

Synthesis example 11

The same procedures as in synthesis example 4 were repeated except that 8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride in synthesis example 1 was changed to 3.4 parts of 1,6,7, 12-tetrachloro-3, 4,9, 10-perylenetetracarboxylic dianhydride (manufactured by ComBi Blocks), thereby obtaining 3.7 parts (yield: 79%) of the compound represented by formula (I-94) (also referred to as compound I-94).

< identification of Compound I-94 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－725

Accurate mass 726

Synthesis example 12

The same operation as in synthesis example 1 was carried out except that 8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride in synthesis example 1 was changed to 3.5 parts of 1, 7-dibromo-3, 4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Aldrich), thereby obtaining 2.7 parts of a compound represented by formula (I-100) (also referred to as compound I-100) (yield 65%).

< identification of Compound I-100 >

(Mass Spectrum) ionization mode ESI-M/z [ M-H ]]^－661

Accurate mass 662

Synthesis example 13

An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was changed to a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was charged and heated to 80 ℃ with stirring. Then, 38 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 5 hours^2,6]Decan-8-yl ester and acrylic acid 3, 4-epoxytricyclo [5.2.1.0²^,6]A mixed solution of 289 parts of a mixture of decane-9-yl esters (containing 1:1 ratio in terms of molar ratio) and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution prepared by dissolving 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was held at 80 ℃ for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution containing 35.1% of a solid content and having a viscosity of 125 mPas as measured with a type B viscometer (23 ℃). The weight-average molecular weight Mw of the resulting copolymer was 9.2X 10³The dispersion degree was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. The resin B1 has the following structural units.

Example 1

(1) Preparation of coloring composition

The ingredients were mixed in the following proportions and the colorant was dispersed using a bead mill. Thereafter, the beads were removed by filtration to obtain coloring composition 1.

Next, the respective components were mixed in the following proportions to obtain a colored curable resin composition 1.

(2) Production of colored coating film

The colored curable resin composition is applied onto a 5cm square glass substrate (EAGLE XG; manufactured by CORNING) by spin coating so that the post-baking film thickness is 1.7 to 2 μm, and then pre-baked at 100 ℃ 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 an exposure machine (TME-150 RSK; manufactured by TOPCON, Inc.) at a thickness of 80mJ/cm in an atmospheric atmosphere²The exposure amount (365nm basis) of (A) was irradiated with light. After the light irradiation, the resultant was postbaked at 230 ℃ for 30 minutes in an oven to obtain a colored coating film.

(3) Heat resistance test

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

(4) Light resistance test

The obtained COLORED coating film was provided with an ultraviolet cut filter (color OPTICAL GLASS L38; manufactured by HOYA corporation; cut off light of 380nm or less), irradiated with xenon lamp light for 48 hours by a light resistance tester (SUNTEST CPS +; manufacturedby seiko Seiko Co., Ltd.), and then measured for absorbance by a color measuring machine. The absorbance retention was determined from the absorbance change at the maximum absorption wavelength of the colored coating film before and after the light resistance test.

Examples 2 to 12 and comparative example 1

The same procedures as in example 1 were carried out except that 50 parts of the compound (I-2) (example 2), 50 parts of the compound (I-3) (example 3), 50 parts of the compound (I-4) (example 4), 50 parts of the compound (I-5) (example 5), 50 parts of the compound (I-6) (example 6), 50 parts of the compound (I-7) (example 7), 50 parts of the compound (I-8) (example 8), 50 parts of the compound (I-9) (example 9), 50 parts of the compound (I-91) (example 10), 50 parts of the compound (I-94) (example 11), 50 parts of the compound (I-100) (example 12) or 50 parts of the solvent Green 5 (manufactured by Tokyo chemical industry Co., Ltd.) (comparative example 1) was used in place of 50 parts of the compound (I-1) to prepare a colorant, a colored curable resin composition was obtained. The results are shown in Table 3.

[ Table 4]

Claims

Translated fromChinese

1.一种着色组合物，包含着色剂和树脂，着色剂含有下述式(I)表示的化合物，1. A coloring composition comprising a colorant and a resin, wherein the colorant contains a compound represented by the following formula (I),

式(I)中，In formula (I),

R¹和R²各自独立地表示碳原子数1～20的2价烃基，R¹ and R² each independently represent a divalent hydrocarbon group having 1 to 20 carbon atoms,

R³～R¹⁰各自独立地表示氢原子、硝基、卤素原子、或可具有取代基的碳原子数1～40的烃基。R³ to R¹⁰ each independently represent a hydrogen atom, a nitro group, a halogen atom, or an optionally substituted hydrocarbon group having 1 to 40 carbon atoms.

2.根据权利要求1所述的着色组合物，其中，所述R¹和R²各自独立地为碳原子数1～20的链烷二基。2 . The coloring composition according to claim 1 , wherein the R¹ and R² are each independently an alkanediyl group having 1 to 20 carbon atoms. 3 .

3.根据权利要求1所述的着色组合物，其中，所述R¹和R²各自独立地为碳原子数1～20的2价脂环式烃基。3 . The coloring composition according to claim 1 , wherein the R¹ and R² are each independently a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms. 4 .

4.根据权利要求1所述的着色组合物，其中，所述R¹和R²各自独立地为碳原子数1～20的2价芳香族烃基。4 . The coloring composition according to claim 1 , wherein the R¹ and R² are each independently a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms. 5 .

5.根据权利要求1～4中任一项所述的着色组合物，其中，所述R³～R¹⁰为氢原子。5 . The coloring composition according to claim 1 , wherein the R³ to R¹⁰ are hydrogen atoms. 6 .

6.一种着色固化性树脂组合物，包含式(I)表示的化合物、树脂、聚合性化合物、聚合引发剂和溶剂，6. A colored curable resin composition comprising a compound represented by formula (I), a resin, a polymerizable compound, a polymerization initiator and a solvent,

式(I)中，In formula (I),

7.一种滤色器，是由权利要求6所述的着色固化性树脂组合物形成的。7 . A color filter formed of the colored curable resin composition according to claim 6 .

8.一种显示装置，含有权利要求7所述的滤色器。8. A display device comprising the color filter of claim 7.