TWI810399B - Colored curable resin composition, color filter and display device - Google Patents

Abstract

The present invention provides a coloring composition excellent in heat resistance and light resistance. A coloring composition includes a colorant and a resin, and the colorant includes a compound represented by the following formula (I).

Description

Colored curable resin composition, color filter and display device place

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

Colorants are used, for example, in the fields of fiber materials, liquid crystal display devices, inkjet, etc. to display colors using reflected light or transmitted light. As a colorant, 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 of manufacturing an optical semiconductor electrode by immersing a base material of a metal oxide semiconductor in a solution containing a compound represented by the following formula (Patent Document 1 ).

[Chem 2]

[Prior art literature]

[Patent Document]

[Patent Document 1] Japanese Patent Laid-Open No. 10-189065

[Non-patent literature]

[Non-Patent Document 1] Color Index (Published by The Society of Dyers and Colourists)

In the field of colorants, a colorant having better heat resistance and light resistance than Solvent Green 5 is desired.

An object of the present invention is to provide a coloring composition that exhibits better heat resistance and light resistance than a coloring composition containing Solvent Green 5.

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

[1] A coloring composition including a colorant and a resin, wherein the colorant includes a compound represented by the following formula (I).

[Chem 3]

[In the formula (I), R ¹ and R ² independently represent a divalent hydrocarbon group with 1 to 20 carbon atoms.

R ³ to R ¹⁰ each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent]

[2] The coloring composition as described in [1], wherein the R ¹ and R ² are each independently an alkanediyl group having 1 to 20 carbon atoms.

[3] The coloring composition as described in [1], wherein the R ¹ and R ² are each independently a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms.

[4] The coloring composition as described in [1], wherein the R ¹ and R ² are each independently a divalent aromatic hydrocarbon group having 1 to 20 carbon atoms.

[5] The coloring composition according to any one of [1] to [4], wherein R ³ to R ¹⁰ are hydrogen atoms.

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

[chemical 4]

[In the formula (I), R ¹ and R ² independently represent a divalent hydrocarbon group with 1 to 20 carbon atoms.

R ³ to R ¹⁰ each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent]

[7] A color filter formed of the colored curable resin composition as described in [6].

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

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

(1) Coloring composition

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

The coloring agent (A) contains the compound (henceforth also referred to as compound (I)) represented by formula (I).

The coloring agent (A) may also contain coloring agents other than the compound (I) (hereinafter, also called colorant (A1)).

One or more kinds of colorants (A1) may also be contained in the colorant (A).

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

Compound (I) can also be dispersed in solvent (E).

<Compound (I)>

The divalent hydrocarbon group represented by R ¹ and R ² has 1-20 carbons, preferably 1-10 carbons, more preferably 1-5 carbons. Examples of the divalent hydrocarbon group include a divalent chain aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group, and a divalent aromatic hydrocarbon group.

The divalent chain aliphatic hydrocarbon group represented by R ¹ and R ² may be saturated or unsaturated. Among them, a divalent saturated chain aliphatic hydrocarbon group (hereinafter also referred to as an alkanediyl group) is preferable. The alkanediyl group may be linear or branched.

Examples of straight-chain alkanediyl represented by ^R1 and ^R2 include: methylene, ethylidene, propane-1,3-diyl, butane-1,4-diyl, pentane-1 ,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1 ,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, Pentadecane-1,15-diyl, Hexadecane-1,16-diyl, Heptadecan-1,17-diyl, Octadecane-1,18-diyl, Nonadecane-1, 19-diyl, and eicosane-1,20-diyl, etc. Among them, preferably alkanediyl having 1 to 10 carbons, more preferably alkanediyl having 1 to 6 carbons, further preferably methylene, ethylidene, propane-1,3-diyl, butane -1,4-diyl, pentane-1,5-diyl or hexane-1,6-diyl.

Examples of the branched alkanediyl group represented by ^R1 and ^R2 include: 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane- 1,2-diyl, 1-methylbutane-1,4-diyl, 2-methylbutane-1,4-diyl, 2,2-dimethylpropane-1,3-diyl , 2-ethylpropane-1,3-diyl, 2-methylpentane-1,5-diyl, 3-methylpentane-1,5-diyl, 2,3-dimethylpentane Alkane-1,4-diyl, 4-methylpentane-1,2-diyl, etc. Among them, 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 further preferred.

Examples of divalent unsaturated chain aliphatic hydrocarbon groups represented by R ¹ and R ² include ethylene-1,2-diyl, prop-1-ene-1,3-diyl, but-2-ene- 1,4-diyl, and pent-3-ene-1,4-diyl, etc.

The divalent alicyclic hydrocarbon group represented by R ¹ and R ² may be saturated or unsaturated. Among them, a divalent 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 include: cyclopropane-1,2-diyl, cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1 , 4-diyl, cyclooctane-1,5-diyl and other cycloalkanediyl groups. Examples of the polycyclic cycloalkanediyl group include norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, adamantane-2, 6-dibasic etc. Among them, cyclohexane-1,4-diyl is preferred.

Examples of the divalent unsaturated alicyclic hydrocarbon group represented by R ¹ and R ² include cyclohex-2-ene-1,4-diyl and the like.

The divalent aromatic hydrocarbon group represented by R ¹ and R ² (hereinafter also referred to as arenediyl) may be monocyclic or polycyclic.

As a monocyclic aromatic diyl group, a benzenediyl group, an alkylbenzenediyl group, a dialkylbenzenediyl group, etc. are mentioned. Specific examples 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-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, etc.

As a polycyclic aromatic diyl group, a naphthalene-1,5-diyl group, a naphthalene-1,6-diyl group, a naphthalene-1,7-diyl group, a naphthalene-1,8-diyl group etc. are mentioned. In addition, the divalent aromatic hydrocarbon groups represented by R ¹ and R ² may be formed by linking two or more aromatic hydrocarbon groups, such as [1,1'-biphenyl]-4,4'-diyl, etc. .

Aryldiyl represented by R ^{and R2} is preferably monocyclic aryldiyl, more preferably benzene-1,4-diyl, 3,5-dimethylbenzene-1,4-diyl, 2-methylbenzene-1,4-diyl, 2-ethylbenzene-1,4-diyl, and 3-ethyl-5-methylbenzene-1,4-diyl.

R ¹ and R ² are independently preferably selected from the group consisting of alkanediyl with 1 to 20 carbons, cycloalkanediyl with 3 to 20 carbons, and aryldiyl with 6 to 20 carbons A group, more preferably a group selected from the group consisting of an alkanediyl group with 1 to 10 carbons, a cycloalkanediyl group with 3 to 10 carbons, and an aryldiyl group with 6 to 10 carbons, and then Preferably, it is selected from the group consisting of alkanediyl with 1 to 6 carbons, monocyclic cycloalkanediyl with 5 to 7 carbons, benzenediyl, alkylbenzenediyl, and dialkylbenzenediyl Groups in the group, and more preferably selected from 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, 3,5-dimethylbenzene-1,4-diyl groups in the group of .

R ¹ and R ² can each independently be a group formed by combining two or more of the above-mentioned hydrocarbon groups, for example, a group formed by combining a chain hydrocarbon group with an alicyclic hydrocarbon group, or a group formed by combining an aromatic hydrocarbon group with a chain A group formed by combining at least one of a hydrocarbon group and an alicyclic hydrocarbon group. The total carbon number of these combined groups is 20 or less.

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

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

[chemical 6]

As R ¹ and R ² , it is preferred to be independently formula (A-1) ~ formula (A-8), formula (A-14), formula (B-1) ~ formula (B-3), A group represented by formula (B-16) to formula (B-19) or formula (C-3). From the viewpoint of production, the above groups are preferred.

Examples of the halogen atom represented by R ³ to R ¹⁰ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, fluorine atoms and chlorine atoms are preferred.

Examples of the hydrocarbon groups having 1 to 40 carbon atoms represented by R ³ to R ¹⁰ include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain or cyclic.

Examples of saturated or unsaturated chain aliphatic hydrocarbon groups represented by R ³ to R ¹⁰ include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl , undecyl, twelve bases, thirteen bases, fourteen bases, fifteen bases, hexadecyl bases, seven bases, octadecyl bases, nineteen bases, twenty bases, twenty one bases, twenty two bases , 23 bases, 24 bases, 25 bases, 26 bases, 27 bases, 28 bases, 29 bases, 30 bases, 31 bases, 32 bases, Thirty-three bases, thirty-four bases, thirty-pentadecyls, thirty-hexadecyls, thirty-heptadecyls, thirty-octacyls, thirty-nonacyls, tetracyls and other linear alkyl groups; isopropyl, Isobutyl, second butyl, third butyl, (2-ethyl) butyl, isopentyl, neopentyl, third pentyl, (1-methyl) pentyl, (2-methyl) ) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl etc. Branched chain alkyl, etc.; vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1,3- butadienyl, (1-(2-propenyl))ethenyl, (1,2-dimethyl)propenyl, alkenyl such as 2-pentenyl; etc. The carbon number of the saturated or unsaturated chain aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, still more preferably 1-15, especially preferably 1-10. Among them, a straight-chain or branched-chain alkyl group having 1 to 8 carbon atoms is even more preferable, and a methyl group or an ethyl group is particularly preferable.

The saturated or unsaturated alicyclic hydrocarbon groups represented by R ³ to R ¹⁰ 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, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octyl Cycloalkyl groups such as cyclohexyl, 4-cyclohexylcyclohexyl; cyclohexenyl (such as cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl and other cycloalkenyl groups; norbornanyl, adamantyl, bicyclo[2.2.2]octyl, etc. The carbon number of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3-30, more preferably 3-20, further preferably 4-20, especially preferably 4-15, further preferably 5-15, particularly preferably 5~10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl are most preferable.

Examples of the aromatic hydrocarbon group represented by R ³ to R ¹⁰ include: phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylbenzene base, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl base, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m- -Tertiary butylphenyl, p-tertiary butylphenyl, 3,5-di(tertiary butyl)phenyl, mesityl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(2-propyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(2,4,4-tri Methyl-2-pentyl) phenyl, 1-naphthyl, 2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2- Aromatic hydrocarbon groups such as naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl and pyrenyl; etc. The carbon number of the aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, and still more preferably 6-15.

The hydrocarbon groups represented by R ³ to R ¹⁰ may be groups formed by combining two or more of the listed hydrocarbon groups, for example, aromatic hydrocarbon groups, and at least one of chain hydrocarbon groups and alicyclic hydrocarbon groups. The formed group, its example can enumerate: Aralkyl such as benzyl, phenethyl, 1-methyl-1-phenylethyl; Phenyl vinyl (phenyl ethyl) (phenyl vinyl (phenyl vinyl) ) and other aryl alkenyl groups; phenylethynyl and other aryl alkynyl groups; biphenyl, terphenylyl and other phenyl groups bonded with more than one phenyl group; cyclohexylmethylphenyl, benzyl Phenyl, (dimethyl(phenyl)methyl)phenyl, etc.

The hydrocarbon group represented by R ³ to R ¹⁰ may be a group formed by combining two or more of the listed hydrocarbon groups, for example, it may be a group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples thereof include : Cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclo An alkyl group in which at least one alicyclic hydrocarbon group is bonded to a hexylethyl group, an adamantylmethyl group, or the like.

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

Examples of substituents that the hydrocarbon groups having 1 to 40 carbon atoms represented by ^R3 to ^R10 include, for example: halogen atoms, formyl groups, carboxyl groups, formyloxy groups, hydroxyl groups, thiol groups, and sulfo groups , sulfamoyl, pentafluorosulfanyl, carbamoyl, amino, nitro, cyano, -COR ¹² , -COOR ¹² , -OCOR ¹² , -OR ¹² , -SR ¹² , -SOR ¹² , -SO ₂ R ¹² , -SO ₂ NHR ¹² , -SO ₂ NR ¹² R ¹³ , -CONHR ¹² , -CONR ¹² R ¹³ , -NHR ¹² , -NR ¹² R ¹³ , -NHCOR ¹² , -NR ¹³ COR ¹² wait.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned. Among them, fluorine atoms and chlorine atoms are preferred.

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

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

Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, Thirteen bases, fourteen bases, fifteen bases, sixteen bases, seventeen bases, octadecyl bases, nineteen bases, twenty bases, etc.

Examples of -COR ¹² include: acetyl, propionyl, butyl, 2,2-dimethylpropionyl, pentyl, hexyl, (2-ethyl)hexyl, heptyl , Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Helicyl, Benzoyl, etc.

Examples of -COOR ¹² include: methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl Base) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl , Eicosyloxycarbonyl, etc.

Examples of -OCOR ¹² include: acetyloxy, propionyloxy, butyryloxy, 2,2-dimethylacryloxy, pentyloxy, hexyloxy, (2 -Ethyl)hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, undecyloxy oxy, benzoyloxy, vinylcarbonyloxy, 2-propenylcarbonyloxy and the like.

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

Examples of -SR ¹² include methylmercapto, ethylmercapto, propylmercapto, butylmercapto, tert-butylmercapto, pentylmercapto, hexylmercapto, (2-ethyl)hexylmercapto, heptylmercapto, Octylmercapto, nonylmercapto, decylmercapto, undecylmercapto, dodecylmercapto, eicosylmercapto, phenylmercapto and o-tolylmercapto, etc.

Examples of -SOR ¹² include methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl, pentylsulfinyl, phenylsulfinyl, Naphthylsulfinyl, etc.

Examples of -SO ₂ R ¹² include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, phenylsulfonyl, and naphthylsulfonyl. Base etc.

Examples of -SO ₂ NHR ¹² include: N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butyl Base sulfamoyl group, N-isobutyl sulfamoyl group, N-second butyl sulfamoyl group, N-third butyl sulfamoyl group, N-pentyl sulfamoyl group, N-( 1-ethylpropyl) sulfamoyl group, N-hexyl sulfamoyl group, N-(2-ethyl) hexyl sulfamoyl group, N-heptyl sulfamoyl group, N-octyl sulfamoyl group base, N-nonyl sulfamoyl group, N-decyl sulfamoyl group, N-undecyl sulfamoyl group, N-dodecyl sulfamoyl group, N-eicosyl sulfamoyl group, N-phenylsulfamoyl, etc.

Examples of -SO ₂ NR ¹² R ¹³ include N,N-dimethylsulfamoyl, N,N-ethylmethylsulfamoyl, N,N-diethylsulfamoyl, N ,N-Propylmethylsulfamoyl, N,N-Dipropylsulfamoyl, N,N-Isopropylmethylsulfamoyl, N,N-Diisopropylsulfamoyl , N,N-tert-butylmethylsulfamoyl, N,N-diisobutylsulfamoyl, N,N-di-second-butylsulfamoyl, N,N-di-third Butylsulfamoyl, N,N-butylmethylsulfamoyl, N,N-dibutylsulfamoyl, N,N-dipentylsulfamoyl, N,N-di(1- Ethylpropyl)sulfamoyl, N,N-dihexylsulfamoyl, N,N-di(2-ethyl)hexylsulfamoyl, N,N-diheptylsulfamoyl, N,N-octylmethylsulfamoyl, N,N-dioctylsulfamoyl, N,N-dinonylsulfamoyl, N,N-decylmethylsulfamoyl, N,N-undecylmethylsulfamoyl, N,N-dodecylmethylsulfamoyl, N,N-eicosylmethylsulfamoyl, N,N-phenylmethyl Aminosulfonyl, N,N-diphenylsulfamoyl, etc.

Examples of -CONHR ¹² include: N-methylaminoformyl, N-ethylaminoformyl, N-propylaminoformyl, N-isopropylaminoformyl, N-butylamine Formyl, N-isobutylaminoformyl, N-second butylaminoformyl, N-tertbutylaminoformyl, N-pentylaminoformyl, N-(1- Ethylpropyl)aminoformyl, N-hexylaminoformyl, N-(2-ethyl)hexylaminoformyl, N-heptylaminoformyl, N-octylaminoformyl, N-nonylaminoformyl, N-decylaminoformyl, N-undecylaminoformyl, N-dodecylaminoformyl, N-eicosylaminoformyl, N- Phenylaminoformyl, etc.

Examples of -CONR ¹² R ¹³ include N,N-dimethylaminoformyl, N,N-ethylmethylaminoformyl, N,N-diethylaminoformyl, N,N- -Propylmethylaminoformyl, N,N-dipropylaminoformyl, N,N-isopropylmethylaminoformyl, N,N-diisopropylaminoformyl, N ,N-tert-butylmethylaminoformyl, N,N-diisobutylaminoformyl, N,N-di-second-butylaminoformyl, N,N-di-tert-butyl Aminoformyl, N,N-Butylmethylaminoformyl, N,N-Dibutylaminoformyl, N,N-Butyloctylaminoformyl, N,N-Dipentylaminoformyl Acyl, N,N-bis(1-ethylpropyl)aminoformyl, N,N-dihexylaminoformyl, N,N-di(2-ethyl)hexylaminoformyl, N ,N-diheptylaminoformyl, N,N-octylmethylaminoformyl, N,N-dioctylaminoformyl, N,N-dinonylaminoformyl, N, N-decylmethylaminoformyl, N,N-undecylmethylaminoformyl, N,N-dodecylmethylaminoformyl, N,N-eicosylmethylaminoformyl Acyl, N,N-phenylmethylaminoformyl, N,N-diphenylaminoformyl, etc.

Examples of -NHR ¹² include: N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamine group Base, N-second butylamine, N-tertiary butylamine, N-pentylamine, N-hexylamine, N-(2-ethyl)hexylamine, N-heptylamine Base, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-benzene Amino groups etc.

Examples of -NR ¹² R ¹³ include: N,N-dimethylamino, N,N-ethylmethylamino, N,N-diethylamino, N,N-propylmethylamine group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N,N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N- Diisobutylamine, N,N-di-second-butylamino, N,N-di-tert-butylamino, N,N-butylmethylamino, N,N-dibutylamine N,N-dipentylamine, N,N-bis(1-ethylpropyl)amino, N,N-dihexylamino, N,N-bis(2-ethyl)hexylamine N,N-diheptylamino, N,N-dioctylamino, N,N-dinonylamino, N,N-decylmethylamino, N,N-undecyl Methylamine, N,N-dodecylmethylamino, N,N-eicosylmethylamino, N,N-phenylmethylamino, N,N-diphenylamino, etc. .

Examples of -NHCOR ¹² include: acetylamino group, propionylamino group, butyrylamine group, 2,2-dimethylacrylamine group, pentylamino group, caproylamine group, ( 2-Ethyl) hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, twenty-one Acylamino group, benzoylamino group, etc.

Examples of -NR ¹³ COR ¹² include N-methyl-N-acetylamino group and the like.

The -CH _{2 -} contained in the hydrocarbon group with 1 to 40 carbon atoms represented by R ³ to R ¹⁰ and which does not constitute a ring may be substituted with -O-, -CO-, -S(O) ₂ -, -NR ^x1 -. Wherein, -COOH and -S(O) ₂ OH are not formed by substituting -CH ₂ -. R ^x1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, isopropyl group, isobutyl group, sec-butyl group, isopentyl group and the like.

Examples of R ³ to R ¹⁰ include groups represented by the following formulae. * Indicates a bond.

[chemical 8]

[chemical 9]

[chemical 10]

[chemical 11]

R ³ to R ¹⁰ are preferably hydrogen atom, halogen atom, hydroxyl group, nitro group, cyano group, -CH ₃ , formula (D-1) ~ formula (D-18), formula (E-1) ~ Groups represented by formula (E-27), formula (F-1) to formula (F-18), and formula (G-1) to formula (G-27). The halogen atoms are preferably chlorine atoms and bromine atoms. When these atoms are included as halogen atoms, the colored pattern or colored coating film formed from the colored curable resin composition tends to exhibit excellent heat resistance or high transmittance at a wavelength of 630 nm. From the viewpoint of production, R ³ to R ¹⁰ are preferably hydrogen atoms.

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

[Table 1]

[Table 2]

[table 3]

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

Preferred embodiments of the compound (I) in the present invention include compounds represented by the following formula (Ia) (hereinafter also referred to as compound (Ia)).

[In the formula (Ia), R ^1a and R ^2a each independently represent an alkanediyl group having 1 to 20 carbon atoms.

R ^3a to R ^10a each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent]

Examples of the alkanediyl group represented by R ^1a and R ^2a are the same as the examples of the alkanediyl group in the description of R ¹ and R ² in the compound (I).

The definitions of R ^3a to R ^10a are the same as the definitions of R ³ to R ¹⁰ in compound (I).

As the specific example of compound (Ia), can enumerate: compound (I-1)～compound (I-6) shown in table 1～table 3, compound (I-10)～compound (I-15), compound ( I-19)~compound (I-24), compound (I-28)~compound (I-33), compound (I-37)~compound (I-42), compound (I-46)~compound (I -51), compound (I-55)~compound (I-60), compound (I-64)~compound (I-69), compound (I-73)~compound (I-78), compound (I- 82) ~ compound (I-87), Compound (I-91)~Compound (I-96), Compound (I-100)~Compound (I-105), Compound (I-109)~Compound (I-114).

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)) is exemplified.

[In the formula (Ib), R ^1b and R ^2b each independently represent a divalent alicyclic hydrocarbon group with 1 to 20 carbon atoms.

R ^3b to R ^10b each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent]

As an example of a divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by R ^1b and R ^2b , the divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms in the description of R ¹ and R ² in the compound (I) Examples of the alicyclic hydrocarbon group are the same.

The definitions of R ^3b to R ^10b are the same as the definitions of R ³ to R ¹⁰ in compound (I).

As the specific example of compound (Ib), can enumerate: compound (I-9), compound (I-18), compound (I-27), compound (I-36), compound ( I-45), compound (I-54), compound (I-63), compound (I-72), Compound (I-81), Compound (I-90), Compound (I-99), Compound (I-108), Compound (I-117).

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

[In formula (Ic), R ^1c and R ^2c each independently represent a divalent aromatic hydrocarbon group with 1 to 20 carbon atoms.

R ^3c to R ^10c each independently represent a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group with 1 to 40 carbon atoms that may have a substituent]

As an example of a divalent aromatic hydrocarbon group with 1 to 20 carbons represented by R ^1c and R ^2c , the same as the divalent aromatic hydrocarbon group with 1 to 20 carbons in the description of R ¹ and R ² in the compound (I) Examples of the group hydrocarbon group are the same.

The definitions of R ^3c to R ^10c are the same as the definitions of R ³ to R ¹⁰ in compound (I).

As the specific example of compound (Ic), can enumerate: compound (I-7), compound (I-8), compound (I-16), compound (I-17), compound ( I-25), compound (I-26), compound (I-34), compound (I-35), Compound (I-43), Compound (I-44), Compound (I-52), Compound (I-53), Compound (I-61), Compound (I-62), Compound (I-70), Compound (I-71), compound (I-79), compound (I-80), compound (I-88), compound (I-89), compound (I-97), compound (I-98), compound ( I-106), compound (I-107), compound (I-115), compound (I-116).

Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) and a compound represented by the following formula (ca1) in a solvent.

[wherein, R ³ to R ¹⁰ have the same definitions as described above]

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

Examples of compounds represented by formula (pt1) include: 3,4,9,10-perylene tetra Carboxylic acid dianhydride, etc.

Examples of divalent hydrocarbon groups having 1 to 20 carbon atoms represented by R in formula (ca1) and examples of divalent hydrocarbon groups having 1 to 20 carbon atoms in the description of ^R1 and ^R2 in the compound (I) same.

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

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

Examples of the solvent include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2- Alcohol solvents such as 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 solvents such as hexane Hydrocarbon solvents; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone ; Dimethyl sulfide and other sulfide solvents.

The usage-amount of a solvent is 1 mass part - 1000 mass parts normally with respect to 1 mass part of the compound represented by formula (pt1).

The reaction temperature is usually not less than -100°C and not more than 300°C, preferably not less than -90°C and not more than 200°C, more preferably not less than -10°C and not more than 150°C.

After completion of the reaction, the method for taking out compound (I) is not particularly limited, and it can be taken out by various known methods. For example, compound (I) can be taken out by distilling off the solvent. Furthermore, after distilling off the solvent, the obtained residue may be purified by column chromatography, recrystallization, or the like. Moreover, compound (I) can be taken out by filtration after completion|finish of reaction. In addition, 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 known analytical methods and conditions. Such an analysis method is not particularly limited, and examples thereof include X-ray crystal structure analysis, mass spectrometry (liquid chromatography (liquid chromatography, LC)), nuclear magnetic resonance (nuclear magnetic resonance, NMR) analysis, and elemental analysis, etc. The X-ray crystal structure analysis method can be performed according to "Chemistry of Materials", 2012, volume 24, p.4647-4652, for example.

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

[wherein, ^R represents an alkanediyl group with 1 to 20 carbon atoms]

Examples of the alkanediyl group having 1 to 20 carbons represented by R ^a are the same as the examples of the alkanediyl group having ¹ to 20 carbon atoms in the description of R1 and ^R2 in the compound (I).

Specific examples of the compound (ca1a) include: 2-aminoacetic acid (glycine), 3-aminopropionic acid, 4-aminobutyric acid, 5-aminovaleric acid, 6-aminocaproic acid , 7-aminoheptanoic acid, 8-aminooctanoic acid, 9-aminononanoic acid, 10-aminodecanoic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, 13-aminotridecanoic acid Acid, 14-aminotetradecanoic acid, 15-aminopentadecanoic acid, 16-aminohexadecanoic acid, 17-aminoheptadecanoic acid, 18-aminooctadecanoic acid, 19-aminononadecanoic acid, 20-aminoeicosanic 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-β-homoleucine).

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

[wherein, R ^b represents a divalent alicyclic hydrocarbon group with 1 to 20 carbon atoms]

As an example of a ^divalent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by R, the difference between the divalent alicyclic hydrocarbon group having ¹ to ²⁰ carbon atoms in the description of R and R in compound (I) Example is the same.

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

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

[wherein, R ^c represents a divalent aromatic hydrocarbon group with 1 to 20 carbon atoms]

Examples of the divalent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by R ^c are the same as the examples of the divalent aromatic hydrocarbon group having 1 to 20 carbon atoms in the description of R ¹ and R ² in compound (I). .

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

<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, with respect to the total amount of the colorant (A). Preferably at least 5% by mass, more preferably at least 10% by mass, more preferably at least 20% by mass, even more preferably at least 50% by mass, particularly preferably at least 70% by mass, and most preferably at least 90% by mass. On the other hand, compared to colorant (A) The content of the compound (I) in the colorant (A) is usually 100% by mass or less, for example, 99% by mass or less.

The content of the compound (I) in the coloring composition may be, for example, 0.1% by mass to 99.9% by mass, preferably 0.5% by mass to 99% by mass relative to the total amount of solids in the coloring composition. , more preferably 1% by mass to 95% by mass, more preferably 5% by mass to 90% by mass, more preferably 10% by mass to 80% by mass, more preferably 15% by mass to 70% by mass % by mass or less, more preferably not less than 20 mass % and not more than 60 mass %, particularly preferably not less than 25 mass % and not more than 55 mass %, most preferably not less than 30 mass % and not more than 60 mass %.

In the present specification, "the total amount of solid content in the coloring composition" refers to the total amount of components obtained by excluding all solvent components from the coloring composition. The total amount of solid content and the content of each component relative to it can be measured by known analytical means such as liquid chromatography or gas chromatography.

The content of the colorant (A) in the coloring composition is generally 0.1% by mass to 99% by mass, for example, 0.1% by mass to 90% by mass relative to the total amount of solids in the coloring composition , preferably not less than 0.5% by mass and not more than 80% by mass, more preferably not less than 0.7% by mass and not more than 70% by mass, particularly preferably not less than 1% by mass and not more than 60% by mass.

<Coloring agent (A1)>

The coloring agent (A1) may be a dye or a pigment. As the dye, known dyes can be used, for example, Color Index (Color Index) (Dyeing and Printing Workers Known dyes described in Dyers and Colourists Association (published by The Society of Dyers and Colourists) and dyeing notes (Shikisensha Co., Ltd.). In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes (xanthene dyes), anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, Azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline dye, nitro dye, phthalocyanine dye, perylene dye, etc. . These dyes may be used alone or in combination of two or more.

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

Furthermore, Lumogen (registered trademark) which is a product of BASF (BASF) can be mentioned, for example: Lumogen (Lumogen) (registered trademark) F Huang 083 (manufactured by BASF), Lumogen ( Lumogen (registered trademark) F Yellow 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, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). These may be used alone or in combination of two or more.

Specifically, C.I. Pigment Yellow (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 other yellow pigments; C.I. Pigment Orange (Pigment Orange) 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C.I. Pigment Red (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 other red colors C.I. Pigment Blue (Pigment Blue) 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments; C.I. Pigment Violet (Pigment Violet) 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. Pigment Green (Pigment Green) 7, 36, 58, 59, 62, 63 and other green pigments; C.I. Pigment Brown (Pigment Brown) 23, 25 and other brown pigments; C.I. Pigment Black (Pigment Black) 1, 7, 31, 32 and other black pigments.

The coloring agent (A1) may also be subjected to rosin treatment, surface treatment using a derivative having an acidic group or a basic group, etc., grafting treatment on the surface of the coloring agent (A1) using a polymer compound, etc., using sulfuric acid, etc., if necessary. Micronization treatment such as micronization method, washing treatment with organic solvent or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc., etc. The particle size of the colorant (A1) is preferably substantially uniform.

When the coloring agent (A) contains the compound (I) and the coloring agent (A1), the lower limit of the content of the compound (I) in the coloring agent (A) is usually 1 with respect to the total amount of the coloring agent (A). % by mass or more, preferably at least 2 mass %, more preferably at least 10 mass %, still more preferably at least 25 mass %, particularly preferably at least 50 mass %. On the other hand, the upper limit of the content rate of the compound (I) in a coloring agent (A) is usually less than 100 mass % with respect to the total amount of a coloring agent (A).

In the case where the coloring agent (A) contains the compound (I) and the coloring agent (A1) Here, the content of the coloring agent (A) in the coloring composition is generally 0.1% by mass to 99% by mass, for example, 0.1% by mass to 90% by mass relative to the total amount of solids in the coloring composition. % or less, preferably 0.5 mass % to 80 mass %, more preferably 0.7 mass % to 70 mass %, particularly preferably 1 mass % to 60 mass %.

When the coloring composition contains the solvent (E), it is also possible to prepare a colorant-containing liquid containing the colorant (A) and the solvent (E) in advance, and then use the colorant-containing liquid to prepare a coloring composition. In the case where the colorant (A) is insoluble in the solvent (E), the colorant-containing liquid can be prepared by dispersing and mixing the colorant (A) in the solvent (E). The coloring agent-containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.

The solid content in the colorant-containing liquid is preferably 0.01% by mass to 99.99% by mass relative to the total amount of the colorant-containing liquid, more preferably 0.1% by mass to 99.9% by mass, still more preferably 0.1% by mass to 99% by mass, more preferably 1% by mass to 90% by mass, more preferably 1% by mass to 60% by mass, still more preferably 3% by mass to 50% by mass , especially preferably at least 3% by mass and at most 30% by mass, and most preferably at least 5% by mass and not more than 30% by mass.

The content of the coloring agent (A) in the coloring agent-containing liquid is usually less than 100% by mass based on the total amount of solids in the coloring agent-containing liquid, preferably 0.0001% by mass to 99.9999% by mass, more preferably 0.01% by mass to 99% by mass, more preferably 0.1% by mass to 99% by mass, most preferably 1% by mass % to 99% by mass, more preferably not less than 2% by mass to 99% by mass.

In the present specification, "the total amount of solid content in the colorant-containing liquid" means the total amount of components after the solvent (E) has been removed from the colorant-containing liquid. The total amount of solid content and the content of each component relative to it can be measured by known analytical means such as liquid chromatography or gas chromatography.

The coloring agent (A) can be brought into a state where the coloring agent (A) is uniformly dispersed in the coloring agent-containing liquid by containing a dispersant and performing a dispersion treatment. The coloring agent (A) may be dispersed individually, or may be mixed and dispersed in two or more types.

Surfactant etc. are mentioned as a dispersing agent, Any of cationic type, anionic type, nonionic type, and amphoteric surfactant may be sufficient. Specifically, surfactants, such as polyester type, polyamine type, and acrylic type, etc. are mentioned. These dispersants may be used alone or in combination of two or more. As a dispersant, when expressed by a trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Kyoeisha Chemical Co., Ltd.), Registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Co., Ltd.), Ajisper (registered trademark) (Ajizhi Su Precision Technology (manufactured by Ajinomoto Fine-Techno) Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-chemie Co., Ltd.), BYK (registered trademark ) (manufactured by BYK-chemie (stock)), etc.

In order to prepare the colorant-containing liquid, in the case of using a dispersant, The amount of the dispersant (solid content) used is usually not more than 10000 parts by mass, preferably not more than 5000 parts by mass, more preferably not more than 1000 parts by mass, and still more preferably not more than 500 parts by mass, relative to 100 parts by mass of the colorant (A). Below, preferably 300 mass parts or less, more preferably 100 mass parts or less, still more preferably 5 mass parts or more and 100 mass parts or less, particularly preferably 5 mass parts or more and 50 mass parts or less. When the usage-amount of this dispersant exists in the said range, there exists a tendency for the coloring agent containing liquid of a more uniform dispersion state to be obtained.

<Resin (B)>

The resin (B) is preferably an alkali-soluble resin, and more preferably has at least one monomer (hereinafter, sometimes referred to as "monomer" selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides). A polymer of structural units of body (a)").

The resin (B) preferably has 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 copolymers of other structural units.

Examples of other structural units include: derived from a monomer (a) that can be copolymerized with the monomer (a), which is different from the monomer (a) and the monomer (b). Hereinafter, it may be referred to as "monomer (a) A structural unit of the body (c)"), a structural unit 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-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; Malic acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinyl phthalate Dicarboxylic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid Unsaturated dicarboxylic acids such as formic acid and 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene , 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2 Bicyclic unsaturated compounds containing carboxyl groups such as alkenes; carboxylic acid anhydrides such as anhydrides of unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid; succinic acid mono[2-(meth)acryloxyethyl unsaturated mono[(meth)acryloxyalkyl] of dibasic or higher polycarboxylic acids such as mono[2-(meth)acryloxyethyl]phthalate and mono[2-(meth)acryloxyethyl]phthalate Esters; unsaturated acrylic esters containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid, etc.

Among these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferable from the viewpoint of copolymerization reactivity or the solubility of the obtained resin in an alkaline aqueous solution.

Monomer (b) refers to a cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) having a carbon number of 2 to 4 and A polymerizable compound having an ethylenically unsaturated bond. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group.

Examples of the monomer (b) include: a monomer having an oxirane group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as a "monomer (b1)"), a monomer having an oxetane group, Monomers of groups and ethylenically unsaturated bonds (hereinafter sometimes referred to as "monomers (b2)") And a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as a "monomer (b3)") and the like.

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

The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond.

Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, and β-ethylglycidyl (meth)acrylate. , glycidyl vinyl ether, vinylbenzyl glycidyl ether, α-methylvinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis (glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3, 4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl) Styrene, 3,4,5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene, etc.

Examples of the monomer (b1-2) include: vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000; manufactured by Daicel (Stock)), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; Daicel (Daicel) manufacturing), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Shacma (Cyclomer (registered trademark) M100; manufactured by Daicel Co., Ltd.), a compound represented by formula (BI), a compound represented by formula (BII), and the like.

[In formula (BI) and formula (BII), R ^a and R ^b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group.

X ^a and X ^b independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S-, or *-R ^c -NH-.

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

*Indicates a bond with O]

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

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

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

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

As X ^a and X ^b , preferably: single bond, methylene, ethylidene, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, more preferably: single bond , *-CH ₂ CH ₂ -O- (* represents a bond with O).

As a compound represented by formula (BI), the compound etc. which are represented by any one of formula (BI-1) - a formula (BI-15) are mentioned. Among them, preferably formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) ~ formula (BI The compound represented by -15) is more preferably a compound represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).

[chem 21]

As the compound represented by formula (BII), a compound represented by any one of formula (BII-1) to formula (BII-15) can be mentioned, and among them, formula (BII-1), Compounds represented by formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) ~ formula (BII-15), more preferably can Compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15) are listed.

[chem 22]

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

As the monomer (b2), a monomer having an oxetanyl group and a (meth)acryloxy group is more preferable.

Examples of the monomer (b2) include: 3-methyl-3-methacryloxy Methyloxetane, 3-methyl-3-acryloxymethyloxetane, 3-ethyl-3-methacryloxymethyloxetane, 3-Ethyl-3-acryloxymethyloxetane, 3-methyl-3-methacryloxyethyloxetane, 3-methyl-3-propene Acyloxyethyloxetane, 3-ethyl-3-methacryloxyethyloxetane, 3-ethyl-3-acryloxyethyloxetane Cyclobutane etc.

The monomer (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloxy group.

Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

The monomer (b) is preferably the monomer (b1) at the point that reliability such as heat resistance and chemical resistance of the obtained color filter can be further improved. Furthermore, it is more preferable that it is a monomeric body (b1-2) from the point which is excellent in the storage stability of a coloring composition.

Examples of the monomer (c) include: methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second-butyl (meth)acrylate, (meth)acrylate ) tert-butyl acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, (meth) Cyclopentyl acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, (methyl) Tricyclo[5.2.1.0 ^2,6 ]decen-9-yl acrylate, Dicyclopentyloxyethyl (meth)acrylate, Isobornyl (meth)acrylate, Adamantyl (meth)acrylate (meth)acrylates such as ester, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and benzyl (meth)acrylate ; Hydroxyl-containing (meth)acrylates such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; diethyl maleate, diethyl fumarate and itaconic acid Dicarboxylic acid diesters such as diethyl ester; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2- 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[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2 .1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5- Phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tertiary butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxy N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide Dicarbonyl imide derivatives such as hexanoate, N-succinimidyl-3-maleimide propionate and N-(9-acridyl)maleimide; Vinyl-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl-containing nitriles such as (meth)acrylonitrile; vinyl chloride and vinylidene chloride, etc. Halogenated hydrocarbons; vinyl-containing amides such as (meth)acrylamide; esters such as vinyl acetate; 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butane dienes such as dienes; etc.

Among these, in terms of copolymerization reactivity and heat resistance, styrene, vinyl toluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, ( Tricyclo[5.2.1.0 ^2,6 ]decen-9-yl meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, (meth)acrylic acid Tricyclo[5.2.1.0 ^2,6 ]decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[ 2.2.1] Hept-2-ene and benzyl (meth)acrylate, etc.

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 combined with the monomer (a) or the monomer (b) by adding a polymer having a structural unit derived from the monomer (a) or the monomer (b). ) is obtained as a monomer of a group reacted with a group possessed by ) and an ethylenically unsaturated bond.

Examples of such structural units include those obtained by adding glycidyl (meth)acrylate to (meth)acrylic acid units, and those obtained by adding 2-hydroxyethyl (meth)acrylate to maleic anhydride units. Structural units and structural units obtained by adding (meth)acrylic acid to glycidyl (meth)acrylate units. In addition, when these structural units have a hydroxyl group, structural units obtained by further adding carboxylic anhydrides can also be cited as examples. It is a structural unit having an ethylenically unsaturated bond.

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

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

Reaction catalysts (for example, tris(dimethylaminomethyl)phenol, etc.) and polymerization inhibitors (for example, hydroquinone, etc.) of carboxylic acids or carboxylic acid anhydrides and cyclic ethers can also be used as needed.

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

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxycyclohexyl (meth)acrylate 5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate Ester/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleic acid Imine copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/(meth)acrylic acid 2-Hydroxyethyl ester copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyl toluene copolymer, (meth)acrylic acid 3 , 4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo(meth)acrylate Cyclo[5.2.1.0 ^2,6 ]decyl ester/tricyclo[5.2.1.0 ^2,6 ]decenyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3 -Methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, Styrene/(meth)acrylic acid copolymers, resins described in JP-A-9-106071, JP-A-2004-29518, and JP-A-2004-361455, etc.

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

Resin (B) may also combine two or more types. In this case, resin (B) preferably contains at least 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate (Meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide/(meth)acrylic acid base) 2-hydroxyethyl acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyl toluene copolymer, (meth) ) One or more kinds of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably from 1,000 to 100,000, more preferably from 1,000 to 50,000, More preferably, it is 1,000 or more and 30,000 or less, and it is especially preferable that it is 3,000 or more and 30,000 or less.

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

The acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, still more preferably 20 mg-KOH/g or more and 200 mg-KOH/g or less, preferably 20 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 30 mg-KOH/g or more and 170 mg-KOH/g or less, especially Preferably, it is not less than 60 mg-KOH/g and not more than 150 mg-KOH/g, most preferably not less than 65 mg-KOH/g and not more than 135 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

The content of the resin (B) in the colored composition may be, for example, not less than 0.1% by mass and not more than 99.9% by mass, preferably not less than 0.5% by mass and not more than 99% by mass, based on the total amount of solids in the colored composition. More preferably at least 1% by mass and at most 95% by mass, more preferably at least 2% by mass and at most 90% by mass, particularly preferably at least 3% by mass and at most 80% by mass, still more preferably at least 5% by mass and at most 70% by mass % or less, more preferably 7 mass % or more and 60 mass % or less, particularly preferably 10 mass % or more and 50 mass % or less, most preferably 15 mass % or more and 40 mass % or less.

When the coloring agent-containing liquid is prepared in advance and the coloring agent-containing liquid is used to prepare the colored composition of the present invention, the coloring agent-containing liquid may previously contain a part or all of the resin (B) described later contained in the coloring composition. , preferably a part. By containing the resin (B) in advance, the dispersion stability of the colorant-containing liquid can be further improved.

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

<Implementation 1>

The coloring composition of Embodiment 1 is a coloring composition including a colorant (A) and a resin (B), and the colorant (A) includes a colorant represented by the following formula (Ia): compound.

[In the formula (Ia), the definitions of R ^1a to R ^10a are the same as those described above]

The examples and preferred ranges of the content of the compound (Ia) in the colorant (A) are the same as the examples and preferred ranges of the content of the compound (I) in the colorant (A) described above.

<Implementation 2>

The coloring composition of Embodiment 2 is a coloring composition comprising a colorant (A) and a resin (B), and the colorant (A) contains a colorant represented by the following formula (Ib): compound.

[In the formula (Ib), the definitions of R ^1b to R ^10b are the same as those described above]

The examples and preferred ranges of the content of the compound (Ib) in the colorant (A) are the same as the examples and preferred ranges of the content of the compound (I) in the colorant (A) described above.

<Implementation 3>

The colored composition of Embodiment 3 is a colored composition including a colorant (A) and a resin (B), and the colorant (A) includes a compound (Ic).

[chem 25]

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

The examples and preferred ranges of the content of the compound (Ic) in the colorant (A) are the same as the examples and preferred ranges of the content of the compound (I) in the colorant (A) described above.

(2) Colored curable resin composition

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

The colored curable resin composition may further contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)), an antioxidant (hereinafter, sometimes referred to as an antioxidant (G)), a solvent (E) One of the groups formed.

The solid content of the coloring composition contained in the coloring curable resin composition can be appropriately adjusted according to the chroma, lightness, film thickness, etc. required when the coloring curable resin composition is cured, so it is not particularly limited. , based on the total amount of solid content in the colored curable resin composition, for example, it can be 1% by mass to 99% by mass, preferably 1% by mass to 90% by mass, more preferably 2% by mass. % by mass and not more than 80 mass %, more preferably not less than 3 mass % and not more than 70 mass %, more preferably not less than 4 mass % and not more than 60 mass %, still more preferably not less than 5 mass % and not more than 50 mass %, especially Preferably, it is 6 mass % or more and 40 mass % or less, Most preferably, it is 7 mass % or more and 30 mass % or less.

The content of the colorant (A) in the colored curable resin composition can be appropriately adjusted according to the chroma, lightness, film thickness, etc. required when curing the colored curable resin composition, so it is not particularly limited. In the total amount of solid content in the permanent resin composition, for example, it may be 0.1% by mass to 99% by mass, preferably 1% by mass to 90% by mass, more preferably 2% by mass to 80% by mass Not more than 3% by mass and not more than 70% by mass, more preferably not less than 4% by mass and not more than 60% by mass, still more preferably not less than 5% by mass and not more than 50% by mass, particularly preferably not less than 6% by mass and not more than 50% by mass 40% by mass or less, preferably 7% by mass or more and 30% by mass or less.

In the present specification, "the total amount of solid content in the curable colored resin composition" refers to the total amount of components obtained by excluding the solvent (E) from the curable colored resin composition. The total amount of solid content and the content of each component relative to it can be measured by known analytical means 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 to less than 100% by mass, preferably 0.1% by mass to 99.9% by mass relative to the total amount of the colored curable resin composition. Not more than 0.1 mass % to 99 mass %, more preferably 1 mass % to 60 mass %, more preferably 3 mass % to 50 mass %, still more preferably 3 mass % or less Above and below 30% by mass, especially preferably at least 5% by mass and below 30% by mass.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, etc., preferably (meth)acrylate compounds.

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

As a polymerizable compound having two ethylenically unsaturated bonds, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di( Meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(meth)acrylate. Dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate Esters, Tris(2-(Meth)acryloxyethyl)isocyanurate, Ethylene glycol modified pentaerythritol tetra(meth)acrylate, Ethylene glycol modified dipentaerythritol hexa(methyl) Acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, Propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc., preferably dipentaerythritol Penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably from 50 to 4,000, more preferably from 50 to 3,500, still more preferably from 50 to 3,000, particularly preferably from 150 to 2,900, most preferably 250 Above and below 1,500.

In the colored curable resin composition, the content of the polymerizable compound (C) may be, for example, 1% by mass to 99% by mass, preferably 2% by mass to 90% by mass, based on the total amount of solid content. , more preferably 3% by mass to 80% by mass, more preferably 4% by mass to 70% by mass, more preferably 5% by mass to 60% by mass, more preferably 6% by mass to 50% by mass % by mass or less, preferably not less than 7% by mass and not more than 40% by mass.

<Polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids, etc. by the action of light or heat to initiate polymerization, and known polymerization initiators can be used.

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

Examples of O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylmercaptophenyl)butane-1-one-2-imine, N-benzoyl Oxy-1-(4-phenyl Mercaptophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)-3-cyclopentylpropane-1-one-2- Imine, N-acetyloxy-1-(4-phenylmercaptophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4- Phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl -2,4-dioxolanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-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-cyclopentylpropan-1-one-2-imine and the like. In addition, as the O-acyl oxime compound, Irgacure OXE01, OXE02 (above, manufactured by BASF Co., Ltd.) and N-1919 (manufactured by ADEKA Co., Ltd.) can also be used. and other commercial products. Among them, as the O-acyl oxime compound, preferably selected from N-benzoyloxy-1-(4-phenylmercaptophenyl) butane-1-one-2-imine, N-benzene Formyloxy-1-(4-phenylmercaptophenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylmercaptophenyl)- At least one of the group consisting of 3-cyclopentylpropane-1-one-2-imine, more preferably N-benzoyloxy-1-(4-phenylmercaptophenyl)octane -1-keto-2-imine.

As the phenyl alkyl ketone compound, 2-methyl-2-morpholinyl-1-(4-methylmercaptophenyl)propane-1-one, 2-dimethylamino-1-(4 -morpholinophenyl)-2-benzylbutan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-( 4-morpholinyl)phenyl]butan-1-one, etc. As the phenyl alkyl ketone compound, Irgacure 369, 907, 379 (the above, manufactured by BASF Co., Ltd.) can also be used and other commercial products.

Examples of phenylalkyl ketone compounds include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy base) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl) propan-1-one, α,α-diethoxyacetophenone and benzyl dimethyl ketal.

Examples of the biimidazole compound include: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3- Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2 '-Bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4' ,5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl) ) biimidazole (for example, referring to Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.) and 4,4 ', 5,5'-position phenyl is composed of alkoxycarbonyl (carboalkoxy ) substituted biimidazole compounds (for example, refer to Japanese Patent Application Laid-Open No. 7-10913, etc.) and the like.

Examples of triazine compounds include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) base)-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)ethylene Base]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1 ,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl) Vinyl]-1,3,5-triazine, etc.

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 Co., Ltd.) can also be used.

Furthermore, 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, methyl o-benzoylbenzoate , 4-phenylbenzophenone, 4-benzoyl-4'-methyl diphenyl sulfide, 3,3',4,4'-tetra(tert-butyl carbonyl peroxide) diphenyl Benzophenone compounds such as ketone and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2- Chloracridone, benzoyl, methyl phenylglyoxylate and titanocene compounds, etc.

These are preferably used in combination with a polymerization initiation aid (D1) (especially amines) described later.

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

The content of the polymerization initiator (D) may be, for example, not less than 0.01% by mass and not more than 40% by mass relative to the total amount of all resins (B) and polymerizable compounds (C) contained in the colored curable resin composition. , preferably not less than 0.1% by mass and not more than 35% by mass.

<Polymerization Initiation Auxiliary (D1)>

The polymerization start aid (D1) is a compound or a sensitizer for promoting the polymerization of the polymerizable compound whose polymerization is started by the polymerization initiator. In the case of containing the polymerization initiation aid (D1), it is usually used in combination with the polymerization initiator (D).

As a polymerization start aid (D1), an amine compound, an alkoxy anthracene compound, a thioxanthone (thioxanthone) compound, a carboxylic acid compound, etc. are mentioned.

Examples of the amine compound include: triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoate Isoamyl aminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4 '-Bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis (Ethylmethylamino)benzophenone etc., Preferably, 4,4'- bis (diethylamino)benzophenone is mentioned. In addition, commercial items such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used as the amine compound.

Examples of alkoxyanthracene compounds 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, etc.

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

Examples of the carboxylic acid compound include phenylthioglycolic acid, methylphenylthioglycolic acid, ethylphenylthioglycolic acid, methylethylphenylthioglycolic acid, dimethylphenylthioglycolic acid, and methoxyphenylthioglycolic acid. Acetic acid, dimethoxyphenylthioglycolic acid, chlorine Phenylthioglycolic acid, dichlorophenylthioglycolic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthyloxyacetic acid, etc.

When these polymerization initiation aids (D1) are used, the content thereof may be, for example, 0.01% by mass or more and 40% by mass or less with respect to the total amount of the resin (B) and the polymerizable compound (C). Preferably, it is not less than 0.1% by mass and not more than 30% by mass.

<Solvent (E)>

Examples of the solvent (E) include: ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether esters Solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH and not containing -O in the molecule -, -CO- and -COO- solvents), aromatic hydrocarbon solvents, amide solvents and dimethyl sulfide, etc.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. , Butyl propionate, Isopropyl butyrate, Ethyl butyrate, Butyl butyrate, Methyl pyruvate, Ethyl pyruvate, Propyl pyruvate, Methyl acetylacetate, Ethyl acetylacetate, Cyclo Hexanol acetate and γ-butyrolactone, etc.

Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, Tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethyl ether Diol dibutyl ether, anisole, phenetole and methyl anisole, etc.

Examples of ether ester solvents include: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropionic acid Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionate Ethyl ester, Propyl 2-methoxypropionate, Methyl 2-ethoxypropionate, Ethyl 2-ethoxypropionate, Methyl 2-methoxy-2-methylpropionate, 2- Ethoxy-2-methyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol mono Diethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate Ester and Dipropylene Glycol Methyl Ether Acetate etc.

Examples of ketone solvents include: 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2- Pentanone, cyclopentanone, cyclohexanone and isophorone, etc.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.

Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

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

The content of the solvent (E) is usually not more than 99.99% by mass, preferably not less than 0.1% by mass and not more than 99.9% by mass, more preferably not less than 1% by mass and not more than 99.9% by mass, based on the total amount of the colored curable resin composition Not more than 10% by mass and not more than 99% by mass, more preferably not less than 40% by mass and not more than 99% by mass, more preferably not less than 50% by mass and not more than 97% by mass, particularly preferably not less than 70% by mass and not more than 99% by mass 97% by mass or less, preferably 75% by mass or more and 95% by mass or less.

The colored curable resin composition of the present invention can also be prepared using the colored containing liquid prepared by dispersing all or part of the compound (I) in all or part of the solvent (E).

The solid content in the colored containing liquid may be, for example, not less than 0.01% by mass and not more than 99.99% by mass, preferably not less than 0.1% by mass and not more than 99.9% by mass, more preferably 0.1% by mass relative to the total amount of the colored containing liquid. % to 99% by mass, more preferably 1% to 90% by mass, more preferably 1% to 60% by mass, more preferably 3% to 50% by mass, particularly preferably It is not less than 3% by mass and not more than 40% by mass, preferably not less than 5% by mass and not more than 35% by mass.

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

In the case of preparing a colored containing liquid by dispersing all or a part of the compound (I) in all or a part of the solvent (E), the coloring containing liquid can be further improved by including all or a part of the resin (B) in advance. dispersion stability. The content of the resin (B) in the colored liquid containing liquid 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, and still more preferably 1 part by mass relative to 100 parts by mass of the compound (I). It is not less than 5 parts by mass and not more than 500 parts by mass, more preferably not less than 5 parts by mass and not more than 200 parts by mass, still more preferably not less than 10 parts by mass and not more than 100 parts by mass.

Compound (I) may also be subjected to rosin treatment, surface treatment using derivatives introduced with acidic groups or basic groups, etc., grafting treatment on the surface of Compound (I) with polymer compounds, etc., micronization with sulfuric acid, etc. Micronization treatment such as method, cleaning treatment with organic solvent or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc. The particle size of the compound (I) is preferably substantially uniform.

The compound (I) can be brought into a state where the compound (I) is uniformly dispersed in the colored containing liquid by containing a dispersant and performing a dispersion treatment. Compound (I) may be dispersed individually or in combination of two or more compounds.

Surfactant etc. are mentioned as a dispersing agent, Any of cationic type, anionic type, nonionic type, and amphoteric surfactant may be sufficient. Specifically, surfactants, such as polyester type, polyamine type, and acrylic type, etc. are mentioned. The scattered The agents can be used alone or in combination of two or more. As a dispersant, when expressed by a trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Kyoeisha Chemical Co., Ltd.), Registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Co., Ltd.), Ajisper (registered trademark) (Ajizhi (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-chemie Co., Ltd.), BYK (registered trademark ) (manufactured by BYK-chemie (stock)), etc.

In the case of using a dispersant, 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, with respect to 100 parts by mass of compound (I). Preferably at most 500 parts by mass, more preferably at most 300 parts by mass, more preferably at most 100 parts by mass, still more preferably at least 5 parts by mass and at most 100 parts by mass, particularly preferably at least 5 parts by mass and at most 50 parts by mass . When the usage-amount of a dispersing agent exists in the said range, there exists a tendency for the colored containing liquid of a more uniform dispersion state to be obtained.

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

<Leveling agent (F)>

Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, silicone-based surfactants having a fluorine atom, and the like. These may have a polymeric group in a side chain.

Examples of the silicone-based surfactant include those having a siloxane bond in the molecule, and the like. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone Ketone (Toray Silicone) SH28PA, Toray Silicone (Toray Silicone) SH29PA, Toray Silicone (Toray Silicone) SH30PA, Toray Silicone (Toray Silicone) SH8400 (trade name: Toray Dow Corning (shares) ) manufacturing); KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); material (manufactured by Momentive Performance Materials Japan Co., Ltd.), etc.

Examples of the fluorine-based surfactant include those having a fluorocarbon chain in the molecule, and the like. Specifically, examples include: Fluorad (registered trademark) FC430, Fluorad (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), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop ) EF352 (manufactured by Mitsubishi Materials Corporation), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule, and the like. Specifically, examples include: Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (DIC ) (stock) manufacturing), etc.

When the leveling agent (F) is contained, its content is usually not less than 0.0005% by mass and not more than 5% by mass, preferably not less than 0.001% by mass and not more than 1% by mass, based on the total amount of the colored curable resin composition , more preferably from 0.001% by mass to 0.5% by mass, still more preferably from 0.002% by mass to 0.2% by mass, particularly preferably from 0.005% by mass to 0.1% by mass. When content of a leveling agent (F) exists in the said range, the flatness of a color filter can be made favorable.

<Antioxidant (G)>

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

Examples of the phenolic antioxidant include: Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF (BASF) Co., Ltd.), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, BASF (BASF) (Shares) Manufacturing), Irganox 1330 (Irganox 1330: 3,3',3",5,5',5"-hexa-tertiary butyl-α,α',α"-(Mesitylene -2,4,6-triyl)tri-p-cresol, BASF (BASF) (stock) manufacture), Irganox 3114 (Irganox 3114: 1,3,5-tri(3,5-di-di- Tributyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Co., Ltd., Egalex 3790 (Irganox 3790: 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4, 6(1H,3H,5H)-Triketone, manufactured by BASF (Stock)), Irganox 1035 (Irganox 1035: thiobisethylenebis[3-(3,5-di-tertiary Butyl-4-hydroxyphenyl)propionate], BASF (BASF) Co., Ltd.), Irganox 1135 (Irganox 1135: phenylpropionic acid, 3,5-bis(1,1-dimethyl Ethyl)-4-hydroxyl, C7-C9 side chain alkyl ester, BASF (BASF) (stock) manufacturing), Irganox 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o Cresol, BASF (BASF) Co., Ltd.), Irganox 3125 (Irganox 3125, BASF (BASF) Co., Ltd. base)-6-(4-hydroxy-3',5'-di-tert-butylanilino)-1,3,5-triazine, BASF (BASF) Co., Ltd.), Eddie Costa (Adekastab) AO-80 (Adekastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1 ,1-Dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, manufactured by ADEKA (stock), 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.), Shano Cyanox 1790 (Cyanox 1790, manufactured by Cytec Co., Ltd.), Vitamin E (manufactured by Eisai Co., Ltd.), etc.

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

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

<other ingredients>

The colored curable resin composition of the present invention may contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, etc. additives well known in the art.

Examples of adhesion promoters include: vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxy 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethylsilane Oxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercapto propane Trimethoxysilane, 3-mercapto (sulfanyl)propyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyl di Methoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxy Silane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.

<Manufacturing method of colored curable resin composition>

The colored curable resin composition can be obtained by further mixing the colorant (A), resin (B), solvent (E), and leveling agent (F) with a polymerizable compound in the case of patterning by photolithography, for example. (C), a polymerization initiator (D), a polymerization initiation auxiliary agent (D1), and other components are mixed together and prepared.

The pigment is preferably mixed with a part or all of the solvent (E) in advance, and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, part or all of the pigment dispersant and the resin (B) may be prepared as necessary. By mixing the remaining components in the pigment dispersion obtained in this manner so as to have a predetermined concentration, a desired colored curable resin composition can be prepared.

A dye can also be prepared by dissolving a part or all of the solvent (E) in advance, respectively, to prepare a solution. The solution is preferably filtered with a filter having a pore diameter of about 0.01 μm to 1 μm.

It is preferable to filter the colored curable resin composition after mixing with a filter having a pore diameter of approximately 0.1 μm to 10 μm.

(3) Color filter

A color filter can be formed from the colored curable resin composition of the present invention. As a method of forming a colored pattern, a photolithography (photolithograph) method, an inkjet method, a printing method, etc. are mentioned. Among them, photolithography is preferred. The photolithography method is to apply the colored curable resin composition on the substrate, make it dry to form a colored curable resin composition layer, and expose the colored curable resin composition layer through a photomask, The method of development. In photolithography, by not using a photomask and/or not performing development during exposure, a colored coating film that is a cured product of the colored curable resin composition layer can be formed. The colored pattern or colored coating film formed in this way is the color filter of this invention.

The film thickness of the produced color filter is not particularly limited, and can be appropriately adjusted according to the purpose or application, for example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 0.5 μm or less. Below 6μm.

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

The formation of pixels of each color by photolithography can be performed by known or commonly used devices or conditions. For example, it can be produced as follows.

First, apply a colored curable resin composition on a substrate, and perform heat drying (pre-baking) and/or reduced-pressure drying to remove volatile components such as solvents and dry it to obtain smooth color curable resin composition layer.

As a coating method, a spin coating method, a slit coating method, a slit and spin coating method, etc. are mentioned.

The temperature at the time of heating and drying is preferably from 30°C to 120°C, more preferably from 50°C to 110°C. In addition, the heating time is preferably from 10 seconds to 60 minutes, more preferably from 30 seconds to 30 minutes.

When performing reduced-pressure drying, it is preferable to carry out at the temperature range of 20 degreeC or more and 25 degreeC or less under the pressure of 50 Pa or more and 150 Pa or less.

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

Next, the colored curable resin composition layer is exposed through a photomask for forming a target colored pattern. In order to uniformly irradiate the entire exposure surface with parallel light, or to accurately align the mask and the substrate on which the colored curable resin composition layer is formed, it is preferable to use a mask aligner and a stepper. Exposure devices such as steppers.

As a light source used for exposure, the light source which generate|occur|produces the light of the wavelength of 250 nm or more and 450 nm or less can also be used. For example, for light less than 350nm, Cutoff is performed using a filter that cuts off this wavelength range, or light around 436 nm, around 408 nm, and around 365 nm is selectively extracted using a band pass filter that extracts these wavelength ranges. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned.

A colored pattern is formed on a substrate by bringing the exposed colored curable resin composition layer into contact with a developer and developing it. By development, the unexposed part of the colored curable resin composition layer is dissolved in a developing solution and removed.

As a developer, for example, an aqueous solution of a basic compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable. The concentration of these basic compounds in the aqueous solution may be, for example, not less than 0.01% by mass and not more than 10% by mass. Furthermore, the developer may also contain a surfactant.

The developing method may be any one of a liquid covering method, a dipping method, a spraying method, and the like. Furthermore, the board|substrate can also be inclined at arbitrary angles at the time of image development.

The developed substrate is preferably washed with water.

Furthermore, it is preferable to post-bak the obtained colored pattern.

(4) Display device

The color filter is used as a color filter in a display device (such as a liquid crystal display device, an organic electroluminescence (EL) device, an electronic paper, etc.) Useful for color filters used in setups.

[Example]

Hereinafter, the present invention will be described more specifically by citing examples, but the present invention is based on The present invention is not limited to the following examples, and of course can be appropriately modified and implemented within the scope of the above-mentioned and later-described gist, and these are included in the technical scope of the present invention. In addition, hereinafter, unless otherwise specified, "part" means "mass part", and "%" means "mass %".

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

The polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) of resin were measured by the gel permeation chromatography (Gel Permeation Chromatography, GPC) method under the following conditions.

Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40°C

Solvent: THF

Flow rate: 1.0mL/min

The solid content concentration of the analysis sample: 0.001% by mass to 0.01% by mass

Injection volume: 50μL

Detector: Refractive Index (RI)

Standard material for calibration: TSK standard polystyrene (STANDARD POLYSTYRENE) F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

The obtained polystyrene-equivalent weight average molecular weight (Mw) and the number The ratio (Mw/Mn) of the average molecular weight (Mn) 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.), and zinc acetate (manufactured by Kanto Chemical Co., Ltd.) were added. 1.3 parts, and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), were stirred at 150° C. for 7 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 9.1 parts of a compound represented by formula (I-1) (also referred to as compound I-1) (88% yield).

<Identification of Compound I-1>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 505

Exact Mass: 506

Synthesis example 2

Add 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.0 4.6 parts of β-alanine (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto Chemical Co., Ltd.), and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), stirred at 150° C. 14 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 8.7 parts of a compound represented by formula (I-2) (also referred to as compound I-2) (80% yield).

<Identification of compound I-2>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 533

Exact Mass: 534

Synthesis example 3

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.3 parts of 4-aminobutyric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc acetate (manufactured by Kanto Chemical Co., Ltd.) 1.3 parts of (manufactured by Tokyo Chemical Industry Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were stirred at 150° C. for 14 hours. While keeping the resulting mixture as Below 20°C, add 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water prepared in advance, resulting in an orange-red precipitate. 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° C. to obtain 8.8 parts of a compound represented by formula (I-3) (also referred to as compound I-3) (77% yield).

<Identification of Compound I-3>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 561

Exact Mass: 562

Synthesis Example 4

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.0 parts of 5-aminovaleric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc acetate (manufactured by Kanto Chemical Co., Ltd.) 1.3 parts of (manufactured by Tokyo Chemical Industry Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were stirred at 150° C. for 14 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. The mixture containing the orange-red precipitate was filtered, using 400 parts of water and 200 parts of methanol to filter After cleaning the residue. The obtained residue was dried under reduced pressure at 60° C. to obtain 8.8 parts of a compound represented by formula (I-4) (also referred to as compound I-4) (77% yield).

<Identification of compound I-4>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 589

Exact Mass: 590

Synthesis Example 5

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.7 parts of 6-aminocaproic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc acetate (manufactured by Kanto Chemical Co., Ltd.) 1.3 parts of (manufactured by Tokyo Chemical Industry Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were stirred at 150° C. for 14 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 9.5 parts of a compound represented by formula (I-5) (also referred to as compound I-5) (75% yield).

[chem 30]

<Identification of Compound I-5>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 617

Exact 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.), zinc acetate ( 1.3 parts of Kanto Chemical Co., Ltd.) and 314 parts of imidazoles (Tokyo Chemical Industry Co., Ltd.) were stirred at 150° C. for 14 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 10 parts of a compound represented by formula (I-6) (also referred to as compound I-6) (yield 78%).

[chem 31]

<Identification of compound I-6>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 645

Exact Mass: 646

Synthesis Example 7

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.0 parts of 4-aminobenzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc acetate (manufactured by Kanto Chemical Co., Ltd.) (Co., Ltd.) 1.3 parts, and 314 parts of imidazoles (Tokyo Chemical Industry Co., Ltd.) were stirred at 150 degreeC for 22 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 11 parts of a compound represented by formula (I-7) (also referred to as compound I-7) (89% yield).

<Identification of Compound I-7>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 629

Exact Mass: 630

Synthesis Example 8

8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 4-amino-3,5-dimethylbenzoic acid (according to European Journal of Pharmaceutical Chemistry (European Journal) of Medicinal Chemistry) 2014, 78.236) 8.4 parts, zinc acetate (manufactured by Kanto Chemical Co., Ltd.) 1.3 parts, and imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) 314 parts, stirred at 150°C for 22 Hour. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 13 parts of a compound represented by formula (I-8) (also referred to as compound I-8) (90% yield).

<Identification of compound I-8>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 685

Exact Mass: 686

Synthesis Example 9

Add 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), trans/cis-4-aminocyclohexanecarboxylic acid (manufactured by Tokyo Chemical Industry Co., Ltd. ), 7.3 parts of zinc acetate (manufactured by Kanto Chemical Co., Ltd.), and 314 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), were stirred at 150° C. for 22 hours. While keeping the obtained mixture at 20° C. or lower, 267 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1300 parts of water were added in advance, resulting in the formation of an orange-red precipitate. 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° C. to obtain 9.8 parts of a compound represented by formula (I-9) (also referred to as compound I-9) (75% yield).

<Identification of compound I-9>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 641

Exact Mass: 642

Synthesis Example 10

Except changing 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride in Synthesis Example 1 into 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride ( Combi Blocks (ComBi Blocks) company) 3.4 parts, in the same manner as Synthesis Example 1 to obtain 2.9 parts of the compound represented by formula (I-91) (also described as compound I-91) (yield 70%).

<Identification of Compound I-91>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 641

Exact Mass: 642

Synthesis Example 11

Except changing 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride in Synthesis Example 1 into 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride ( Combi Blocks (ComBi Blocks) company) 3.4 parts, in the same manner as Synthesis Example 4 to obtain 3.7 parts of the compound represented by formula (I-94) (also described as compound I-94) (yield 79%).

[chem 36]

<Identification of Compound I-94>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 725

Exact Mass: 726

Synthesis Example 12

In addition to changing 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride in Synthesis Example 1 into 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride (Aldrich ( (manufactured by Aldrich) Co., Ltd.), 2.7 parts of a compound represented by formula (I-100) (also referred to as compound I-100) was obtained in the same manner as in Synthesis Example 1 (yield 65%).

<Identification of Compound I-100>

(mass analysis) ionization mode = ESI-: m/z = [MH] ^- 661

Exact Mass: 662

Synthesis Example 13

An appropriate amount of nitrogen gas was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was put in, and heated to 80° C. while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2 , 6} ] A mixture of decane-9-yl esters (containing a molar ratio of 1:1) 289 parts, 125 parts of propylene glycol monomethyl ether acetate mixed solution. On the other hand, a solution obtained by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition, it was kept at 80° C. for 4 hours, and then cooled to room temperature to obtain a solid content of 35.1% and a viscosity of 125 mPa measured with a B-type viscometer (23° C.). s copolymer (resin B1) solution. The weight average molecular weight Mw of the produced copolymer was 9.2×10 ³ , the degree of dispersion was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. Resin B1 has the following structural units.

Example 1

(1) Preparation of coloring composition

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

Next, each component was mixed in the following ratio, and the colored curable resin composition 1 was obtained.

(2) Preparation of colored coating film

On a 5 cm square glass substrate (Eagle XG; manufactured by Corning Corporation), the colored curable resin composition is coated by spin coating so that the film thickness after baking becomes 1.7 μm to 2 μm, After that, it is prebaked at 100° C. for 3 minutes to form a colored curable resin composition layer. After standing to cool, the colored curable resin composition layer formed on the substrate was exposed to an exposure amount of 80mJ/ ^cm2 (365nm Standard) for light irradiation. After light irradiation, post-baking was performed in an oven at 230° C. for 30 minutes to obtain a colored coating film.

(3) Heat resistance test

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

(4) Light fastness test

On the obtained colored coating film, an ultraviolet cut filter (colored optical glass (COLORED OPTICAL GLASS) L38; manufactured by Baogu (HOYA) Co., Ltd.; cut off light below 380nm) was arranged, and a light fastness tester (Sangtest ( SUNTEST) CPS+: manufactured by Toyo Seiki Co., Ltd.) was irradiated with a xenon lamp for 48 hours, and the absorbance was measured with a colorimeter. The absorbance retention rate was calculated from the change in absorbance at the maximum absorption wavelength of the colored coating film before and after the light resistance test.

Embodiment 2 ~ embodiment 12 and comparative example 1

used in place of 50 parts of compound (I-1) 50 parts of compound (I-2) (embodiment 2), 50 parts of compound (I-3) (embodiment 3), 50 parts of compound (I-4) (embodiment 4), 50 parts of compound ( I-5) (Example 5), 50 parts of compound (I-6) (Example 6), 50 parts of compound (I-7) (Example 7), 50 parts of compound (I-8) ( Example 8), 50 parts of compound (I-9) (Example 9), 50 parts of compound (I-91) (Example 10), 50 parts of compound (I-94) (Example 11), 50 parts of compound (I-100) (embodiment 12), or 50 parts of solvent green (Solvent Green) 5 (manufactured by Tokyo Chemical Industry Co., Ltd.) (comparative example 1) to prepare colorant, in addition, with A colored curable resin composition was obtained in the same manner as in Example 1. The results are shown in Table 3.

[Table 4]

Claims (7)

A colored curable resin composition, comprising a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, and the colorant comprises a compound represented by the following formula (I); the resin comprises: derived from A cyclic ether structure with a number of 2 to 4 and a monomeric unit of an ethylenically unsaturated bond; and a structural unit derived from at least one monomeric body selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides Structural units,

[In formula (I), R ¹ and R ² independently represent a divalent hydrocarbon group with 1 to 20 carbon atoms; R ³ to R ¹⁰ independently represent a hydrogen atom, a nitro group, a halogen atom, or a substituent A hydrocarbon group with 1 to 40 carbons; wherein, when R ¹ and R ² are ethylenyl groups, at least one of R ³ to R ¹⁰ is a nitro group, a halogen atom, or a carbon number with 1 to 40 carbons that may have substituents Hydrocarbyl]. The colored curable resin composition as described in claim 1 of the patent application, wherein the R ¹ and R ² are each independently an alkanediyl group having 1 to 20 carbon atoms. The colored curable resin composition described in claim 1 of the patent application, wherein the R ¹ and R ² are each independently a divalent alicyclic hydrocarbon group with 1 to 20 carbon atoms. The colored curable resin composition described in item 1 of the scope of the patent application, wherein the R ¹ and R ² are each independently a divalent aromatic hydrocarbon group with 1 to 20 carbon atoms. The colored curable resin composition as described in any one of items 1 to 4 of the patent claims, wherein R ³ to R ¹⁰ are hydrogen atoms. A color filter formed of the colored curable resin composition described in any one of the first to fifth claims of the patent application. A display device comprising the color filter described in item 6 of the patent application.