TWI811481B - Colored curable resin composition, color filter and display device - Google Patents

Abstract

The present invention provides a colored composition excellent in heat resistance. A coloring composition includes a colorant and a resin, wherein the colorant includes a compound represented by formula (I) and a fluorescent dye, and the fluorescent dye includes a compound having a structure different from the compound represented by formula (I).

Description

Colored curable resin compositions, color filters and display devices set

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

In the field of organic semiconductor materials, a material containing a perylenetetracarboxylic acid diimide compound is known (Patent Document 1).

[Prior art documents]

[Patent Document]

[Patent Document 1] International Publication No. 2011/105152

In the field of colorants, colorants containing fluorescent dyes are used, and improvements in heat resistance are sought in colored compositions containing such colorants.

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

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 contains It contains a compound represented by the following formula (I) and a fluorescent dye containing a compound having a different structure from the compound represented by the formula (I).

[In formula (I), R ¹ to R ⁴ independently represent an alkyl group having 5 to 10 carbon atoms.

R ⁵ to R ¹² independently represent a hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom, a halogen atom, or a nitro group which may have a substituent]

[2] The colored composition according to [1], wherein the compound having a different structure from the compound represented by the formula (I) is a red fluorescent dye.

[3] The colored composition according to [1] or [2], wherein the red fluorescent dye is a compound represented by the following formula (II).

[Chemicalization 2]

[In formula (II), Ar ¹ to Ar ⁶ independently represent an aryl group which may have a substituent.

R ¹⁵ to R ¹⁸ independently represent a hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom, a halogen atom, or a nitro group which may have a substituent]

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

[In formula (I), R ¹ to R ⁴ independently represent an alkyl group having 5 to 10 carbon atoms.

R ⁵ to R ¹² independently represent a hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom, a halogen atom, or a nitro group which may have a substituent]

[5] A color filter formed from the colored curable resin composition described in [4].

[6] A display device including the color filter according to [5].

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

(1) Coloring composition

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

The coloring agent (A) contains a compound represented by formula (I) (hereinafter also referred to as compound (I)) and a fluorescent dye (hereinafter also referred to as fluorescent dye (a)).

The fluorescent dye (a) contains a compound having a different structure from the compound represented by formula (I). The compound having a different structure means a compound preferably having a different structure (chemical structure) when represented by a chemical formula.

The compound having a different structure from the compound represented by formula (I) may be, for example, a red fluorescent dye.

The red fluorescent dye may be, for example, a compound represented by formula (II) (hereinafter also referred to as compound (II)).

The coloring agent (A) may contain a coloring agent other than the compound (I) and the fluorescent dye (a) (hereinafter also referred to as the coloring agent (A1)).

The colorant (A) may contain one or more colorants (A1).

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

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

<Compound (I)>

The alkyl group represented by R ¹ to R ⁴ has a carbon number of 5 to 10, preferably a carbon number of 5 to 8. The alkyl group represented by R ¹ to R ⁴ may be linear, branched or cyclic, and is preferably linear.

Examples of the linear alkyl group represented by R ¹ to R ⁴ include n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl. Among them, n-pentyl, n-hexyl, n-heptyl and n-octyl are preferred, and n-pentyl and n-hexyl are more preferred. From the viewpoint of solubility in a solvent and fluorescence intensity, these groups are preferred.

Examples of the branched chain alkyl group represented by R ¹ to R ⁴ include: 1-methylbutyl, 1-methylpentyl, 1-methylhexyl, 1-methylheptyl, 1-methyl Octyl, 1-methylnonyl, 1-ethylpropyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylhexyl, 1-ethylheptyl, 1-ethyloctyl base, 2-methylbutyl, 2-methylpentyl, 2-methylhexyl, 2-methylheptyl, 2-methyloctyl, 2-methylnonyl, 2-ethylpropyl, 2-ethylbutyl, 2-ethylpentyl, 2-ethylhexyl, 2-ethylheptyl, 2-ethyloctyl, etc.

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

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

R ¹ to R ⁴ may be the same species or different species, preferably the same species.

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

[Chemistry 5]

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

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

Examples of the saturated or unsaturated chain aliphatic hydrocarbon group represented by R ⁵ to R ¹² include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl , eleven bases, twelve bases, thirteen bases, fourteen bases, fifteen bases, sixteen bases, seventeen bases, eighteen bases, nineteen bases, twenty bases, twenty-one bases, twenty-two bases , twenty-three bases, twenty-four bases, twenty-five bases, twenty-six bases, twenty-seven bases, twenty-eight bases, twenty-nine bases, thirty bases, thirty-one bases, thirty-two bases, Straight-chain alkyl groups such as 33-33yl, 34-yl, 35-yl, 36-yl, 37-yl, 38-yl, 39-yl, 40-yl, etc.; isopropyl, Isobutyl, 2nd butyl, 3rd butyl, (2-ethyl)butyl, isopentyl, neopentyl, 3rd 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))vinyl, (1,2-dimethyl)propenyl, 2-pentenyl and other alkenyl groups; etc. The carbon number of the saturated or unsaturated chain aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10. Among them, a linear or branched chain alkyl group having 1 to 8 carbon atoms is more preferred, and a methyl group or an ethyl group is particularly preferred.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ⁵ to R ¹² 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 and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (such as cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl and cyclooctenyl; Norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc. The carbon number of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, more preferably 4 to 20, especially 4 to 15, more preferably 5 to 15, particularly preferably 5~10. Among them, the most preferred ones are cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl.

Examples of the aromatic hydrocarbon group represented by R ⁵ to R ¹² include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, and 4-ethylphenyl. base, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl base, 3,5-dimethylphenyl, 4-vinylphenyl, o-cumylphenyl, m-cumylphenyl, p-cumylphenyl, o-tert-butylphenyl, m- -Tertiary butylphenyl, p-tertiary butylphenyl, 3,5-di(tertiary butyl)phenyl, mesitylene, 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, anthryl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl and pyrenyl; etc. The carbon number of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 15.

The hydrocarbon group represented by R ⁵ to R ¹² may be a combination of two or more of the listed hydrocarbon groups. For example, it may be a combination of an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of groups that form a group include benzyl, phenethyl, 1-methyl-1-phenylethyl and other aralkyl groups; phenyl ethenyl (phenyl vinyl) ) and other aryl alkenyl groups; aryl alkynyl groups such as phenylethynyl group; biphenyl, terphenylyl (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 ⁵ to R ¹² 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, cyclohexylmethyl Alkyl groups having one or more alicyclic hydrocarbon groups bonded to them, such as hexylethyl group and adamantylmethyl group, etc.

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

Examples of substituents that the hydrocarbon group having 1 to 40 carbon atoms represented by R ⁵ to R ¹² may include a halogen atom, a formyl group, a carboxyl group, a formyloxy group, a hydroxyl group, a thiol group, and a sulfo group. , Aminosulfonyl group, pentafluorosulfanyl, carboxamide group, amine group, nitro group, cyano group, -COR ¹² , -COOR ¹³ , -OCOR ¹³ , -OR ¹³ , -SR ¹³ , -SOR ¹³ , -SO ₂ R ¹³ , -SO ₂ NHR ¹³ , -SO ₂ NR ¹³ R ¹⁴ , -CONHR ¹³ , -CONR ¹³ R ¹⁴ , -NHR ¹³ , -NR ¹³ R ¹⁴ , -NHCOR ¹³ , -NR ¹⁴ COR ¹³ wait.

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

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

The number of carbon atoms in the alkyl group represented by R ¹³ and R ¹⁴ is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 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, eighteen bases, nineteen bases, twenty bases, etc.

Examples of -COR ¹³ include: acetyl group, propyl group, butyl group, 2,2-dimethylpropyl group, pentyl group, hexyl group, (2-ethyl)hexyl group, and heptyl group , octyl group, nonyl group, decyl group, undecyl group, dodecyl group, twenty-one group, benzoyl group, etc.

Examples of -COOR ¹³ include: methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyloxycarbonyl) Base) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl , eicosyloxycarbonyl, etc.

Examples of -OCOR ¹³ include: acetyloxy, propionyloxy, butyloxy, 2,2-dimethylpropyloxy, pentyloxy, hexyloxy, (2 -Ethyl)hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, hexayloxy baseoxy group, benzyloxy group, vinylcarbonyloxy group, 2-propenylcarbonyloxy group, etc.

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

Examples of -SR ¹³ 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 ¹³ include: methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, butylsulfinyl group, pentylsulfinyl group, phenylsulfinyl group, Naphthyl sulfenyl, etc.

Examples of -SO ₂ R ¹³ include: methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, amylsulfonyl group, phenylsulfonyl group, and naphthylsulfonyl group Key et al.

Examples of -SO ₂ NHR ¹³ include: N-methylsulfamide group, N-ethylsulfamide group, N-propylsulfamide group, N-isopropylsulfamide group, and N-butyl group. Aminosulfonyl group, N-isobutylaminesulfonyl group, N-second butylaminesulfonyl group, N-tert-butylaminesulfonyl group, N-pentylaminesulfonyl group, N-( 1-ethylpropyl)aminesulfonyl, N-hexylaminesulfonyl, N-(2-ethyl)hexylaminesulfonyl, N-heptylaminesulfonyl, N-octylaminesulfonyl base, N-nonylamine sulfonyl group, N-decylamine sulfonyl group, N-undecylamine sulfonyl group, N-dodecylamine sulfonyl group, N-eicosylamine sulfonyl group, N-phenylaminosulfonyl, etc.

Examples of -SO ₂ NR ¹³ R ¹⁴ include: N,N-dimethylsulfamide group, N,N-ethylmethylsulfamide group, N,N-diethylsulfamide group, N ,N-propylmethylmethanesulfonyl, N,N-dipropylaminesulfonyl, N,N-isopropylmethylaminesulfonyl, N,N-diisopropylaminesulfonyl , N,N-tert-butylmethylmethanesulfonyl, N,N-diisobutylmethanesulfonyl, N,N-di-second-butylaminesulfonyl, N,N-di-tertiary Butylamine sulfonyl group, N,N-butylmethylamine sulfonyl group, N,N-dibutylamine sulfonyl group, N,N-dipentylamine sulfonyl group, N,N-di(1- Ethylpropyl)aminesulfonyl, N,N-dihexylaminesulfonyl, N,N-di(2-ethyl)hexylaminesulfonyl, N,N-diheptylaminesulfonyl, N,N-octylmethylaminesulfonyl, N,N-dioctylmethylaminesulfonyl, N,N-dinonylmethylaminesulfonyl, N,N-decylmethylaminesulfonyl, N,N-Undecylmethylsulfonamide, N,N-Dodecylmethylsulfonamide, N,N-eicosylmethylsulfonamide, N,N-phenylmethyl Aminosulfonyl, N,N-diphenylaminesulfonyl, etc.

Examples of -CONHR ¹³ include N-methylaminoformyl, N-ethylamineformyl, N-propylamineformyl, N-isopropylamineformyl, and N-butylamine. Formyl, N-isobutylamineformyl, N-second butylamineformyl, N-tert-butylamineformyl, N-pentylamineformyl, N-(1- Ethylpropyl)aminoformyl, N-hexylamineformyl, N-(2-ethyl)hexylamineformyl, N-heptylamineformyl, N-octylamineformyl, N-nonylaminemethyl, N-decylaminemethyl, N-undecylaminemethyl, N-dodecylaminemethyl, N-eicosylaminemethyl, N- Phenylamine formyl, etc.

Examples of -CONR ¹³ R ¹⁴ include: N,N-dimethylamineformyl group, N,N-ethylmethylamineformyl group, N,N-diethylamineformyl group, N,N -Propylmethylaminoformyl, N,N-dipropylamineformyl, N,N-isopropylmethylamineformyl, N,N-diisopropylamineformyl, N ,N-tert-butylmethylaminemethyl,N,N-diisobutylaminemethyl,N,N-di-second-butylaminemethyl,N,N-di-tert-butyl Aminoformyl, N,N-butylmethylaminoformyl, N,N-dibutylamineformyl, N,N-butyloctylamineformyl, N,N-dipentylamineformyl Cyl group, N,N-di(1-ethylpropyl)aminomethyl group, N,N-dihexylaminemethyl group, N,N-di(2-ethyl)hexylaminemethyl group, N ,N-diheptylaminemethyl, N,N-octylmethylaminemethyl, N,N-dioctylaminemethyl, N,N-dinonylaminemethyl, N, N-Decylmethylamineformyl, N,N-Undecylmethylamineformyl, N,N-Dodecylmethylamineformyl, N,N-Eicosylmethylamineformyl Cyl group, N,N-phenylmethylamine carboxyl group, N,N-diphenylamine carboxyl group, etc.

Examples of -NHR ¹³ include: N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, and N-isobutylamino group base, N-second butylamino group, N-tert-butylamino group, N-pentylamino group, N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamine group base, N-octylamine group, N-nonylamino group, N-decylamine group, N-undecylamine group, N-dodecylamine group, N-eicosylamine group, N-phenyl Amino group, etc.

Examples of -NR ¹³ R ¹⁴ include: N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, and N,N-propylmethylamine group base, N,N-dipropylamino group, N,N-isopropylmethylamino group, N,N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N- Diisobutylamino, N,N-di-second butylamino, N,N-di-tertiary butylamino, N,N-butylmethylamino, N,N-dibutylamine base, N,N-dipentylamino, N,N-di(1-ethylpropyl)amine, N,N-dihexylamine, N,N-di(2-ethyl)hexylamine base, N,N-diheptylamine group, N,N-dioctylamine group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylamine group Methylamine, N,N-dodecylmethylamine, N,N-eicosylmethylamine, N,N-phenylmethylamine, N,N-diphenylamine, etc. .

Examples of -NHCOR ¹³ include: acetylamine, propionylamine, butyrylamine, 2,2-dimethylpropylamine, pentylamine, hexylamine, ( 2-Ethyl)hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, twenty-one Cylamine group, benzyl acylamino group, etc.

Examples of -NR ¹⁴ COR ¹³ include N-methyl-N-acetylamine group and the like.

-CH _{2 -} contained in the hydrocarbon group having 1 to 40 carbon atoms represented by R ⁵ to R ¹² and not constituting a ring may be substituted with -O-, -CO-, -S(O) ₂ -, -NR ^x1 -. Among them, -COOH and -S(O) ₂ OH will not be 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, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, isobutyl, 2-butyl, isopentyl, and the like.

Examples of R ⁵ to R ¹² include groups represented by the following formulas. * indicates bonding.

[Chemical 7]

[Chemical 8]

[Chemical 9]

Preferred R ⁵ to R ¹² are hydrogen atom, halogen atom, hydroxyl group, nitro group, cyano group, -CH ₃ , formula (D-1) to formula (D-18), formula (E-1) to Groups represented by formula (E-27), formula (F-1) to formula (F-18), and formula (G-1) to formula (G-27). From the viewpoint of fluorescence intensity, R ⁵ to R ¹² are preferably hydrogen atoms.

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

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

Preferable embodiments of the compound (I) in the present invention include a compound represented by the following formula (I-1) (hereinafter also referred to as the compound (I-1)).

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

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 (n1) in a solvent.

[Chemical 12]

[In the formula, R ⁵ ~ R ¹² are the same as the definitions mentioned above]

H ₂ NCHR ¹ R ² (n1)

[In the formula, R ¹ and R ² are the same as the above definitions]

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

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

The usage amount of the compound represented by formula (n1) is usually 1 mole or more and 10 mole or less, preferably 1 mole or more and 8 mole or less, based on 1 mole of the compound represented by 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; propyl Ketone solvents such as ketone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichlorobenzene and other Solvents; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; styrene solvents such as dimethyl styrene.

The usage amount of the solvent is usually 1 to 1,000 parts by mass relative to 1 part by mass of the compound represented by formula (pt1).

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

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

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

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

<Fluorescent dye (a)>

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

The red fluorescent dye may be, for example, a compound represented by the following formula (II) (hereinafter also referred to as compound (II)).

[In formula (II), Ar ¹ to Ar ⁶ independently represent an aryl group which may have a substituent.

R ¹⁵ to R ¹⁸ independently represent a hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom, a halogen atom, or a nitro group which may have a substituent]

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

Examples of substituents that the aryl group represented by Ar ¹ to Ar ⁶ may have include a halogen atom, a nitrile group, a nitro group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms. , Alkenyl group with 2 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, aryloxy group, thiol group, alkylthio group with 1 to 10 carbon atoms, allylthio group, sulfo group ), alkylsulfo group, arylsulfo group, silyl group, boron group, arylamine group, aralkylamine group, alkylamine group having 1 to 10 carbon atoms, aryl group, aryl group having 1 to 10 carbon atoms. Substituents in the group consisting of alkyl groups, arylalkenyl groups, heterocyclic groups with 3 to 10 carbon atoms, and ethynyl groups. Among them, an alkyl group having 1 to 10 carbon atoms and a halogen atom are preferred.

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

As the alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 6 carbon atoms is preferred, and an alkyl group having 1 to 4 carbon atoms is more preferred.

The aryl groups represented by Ar ¹ to Ar ⁶ may have one, two or more substituents, or may have no substituents.

Examples of Ar ¹ to Ar ⁶ include groups represented by the following formulas. * indicates bonding.

[Chemical 14]

Preferred Ar ¹ to Ar ⁶ are formula (E-1), formula (E-4), formula (E-7), formula (E-9), formula (E-17), formula (E- 18), a group represented by formula (E-19). If these groups are used, the fluorescence intensity tends to be high. Ar ¹ and Ar ² are preferably the same. Ar ³ ~ Ar ⁶ may be of the same species or may be of different species.

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

[table 3]

[Table 4]

[table 5]

[Table 6]

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

Another preferred embodiment of compound (II) in the present invention includes compounds represented by the following formula (II-2) and formula (II-92) (hereinafter, also referred to as compound (II)). -2), compound (II-92)).

[Chemical 16]

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

[In the formula, R ⁵ ~ R ¹² are the same as the definitions mentioned above]

Ar-NH ₂ (AR1)

Ar-OH (AR2)

[In the formula, Ar has the same definition as Ar ¹ ~ Ar ⁶ mentioned above]

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

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

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

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

Examples of solvents include water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, and 2-ethyl Alcohol solvents such as 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 hydrocarbons such as hexane Solvents; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene and other amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; Trisene solvents such as dimethyl styrene, carboxylic acid solvents such as acetic acid, propionic acid, butyric acid, etc., imidazole, etc. Preferred are N-methylpyrrolidone, imidazole and propionic acid.

The usage amount of the solvent is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt2).

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

After the reaction is completed, the method of taking out compound (II) is not particularly limited, and can be taken out by various known methods. For example, compound (II) can be extracted by distilling off the solvent. Furthermore, after the solvent is distilled off, the obtained residue may be purified by column chromatography, recrystallization, or the like. In addition, after the reaction is completed, compound (II) can be taken out by filtration. In addition, after filtration, the obtained residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the obtained compound (II) can be analyzed by known analysis methods and conditions. The analysis method is not particularly limited, and examples include X-ray crystal structure analysis, mass spectrometry (LC), NMR analysis, elemental analysis, and the like. The X-ray crystal structure analysis method can be performed based on, for example, "Chemistry of Materials", 2012, Vol. 24, p. 4647-4652.

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

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

<Color(A)>

The lower limit of the content rate of the compound (I) in the colorant (A) may be, for example, 0.1% by mass or more relative to the total amount of the colorant (A), and specific examples thereof may be 0.5% by mass, 1% by mass. %, 5 mass%, 10 mass%, 20 mass%, 50 mass%, 70 mass%, 90 mass%, etc.

On the other hand, the upper limit of the content rate of the compound (I) in the colorant (A) may be, for example, 99.9% by mass or less with respect to the total amount of the colorant (A). The method can be 99.5 mass%, 99 mass%, 95 mass%, 90 mass%, 80 mass%, 50 mass%, 30 mass%, 10 mass%, etc.

For example, when the colorant (A) contains the compound (I) and the compound (II), the content rate of the compound (I) in the colorant (A) relative to the total amount of the colorant (A) may be, for example, 1 The content is not less than 99% by mass and not more than 99% by mass, preferably not less than 5% by mass and not more than 70% by mass, and more preferably not less than 10% by mass and not more than 50% by mass.

The lower limit of the content rate of the fluorescent dye (a) in the colorant (A) may be, for example, 0.1% by mass or more relative to the total amount of the colorant (A), and specific examples thereof may be 0.5% by mass, 1% by mass, 5% by mass, 10% by mass, 20% by mass, 50% by mass, 70% by mass, 90% by mass, etc.

On the other hand, the upper limit of the content rate of the fluorescent dye (a) in the colorant (A) may be, for example, 99.9% by mass or less relative to the total amount of the colorant (A). A specific example thereof may be 99.5 mass%, 99 mass%, 95 mass%, 90 mass%, 80 mass%, 50 mass%, 30 mass%, 10 mass% or less, etc.

For example, when the colorant (A) contains the compound (I) and the compound (II), the content rate of the compound (II) in the colorant (A) relative to the total amount of the colorant (A) may be, for example, 1 The content is from mass % to 99 mass%, preferably from 30 mass% to 95 mass%, and more preferably from 50 mass% to 90 mass%.

The content rate of the compound having a structure different from the compound represented by formula (I) in the fluorescent dye (a) may be, for example, 0.1% by mass or more, preferably 0.5% by mass, relative to the total amount of the fluorescent dye (a). or above, more preferably 1% by mass or more, still more preferably 5% by mass or more, particularly preferably 10% by mass or more, still more preferably 20% by mass or more. , further preferably, it is 50 mass % or more, extremely good, 70 mass % or more, and excellent, 90 mass % or more.

On the other hand, the content rate of the fluorescent dye (a) in the colorant (A) is usually less than 100% by mass, preferably 99.5% by mass or less, and more preferably 99% by mass, relative to the total amount of the colorant (A). Mass % or less, more preferably 95 mass % or less, particularly preferably 90 mass % or less, still more preferably 80 mass % or less, still more preferably 50 mass % or less, particularly preferably 30 mass % or less, and excellent 10 mass% or less.

When the compound having a structure different from that of the compound represented by formula (I) is compound (II), the content rate of compound (II) in colorant (A) relative to the total amount of colorant (A) is: The limit value may be, for example, 0.1 mass% or more, and specific examples thereof may be 0.5 mass%, 1 mass% or more, 5 mass% or more, 10 mass%, 20 mass%, 50 mass%, 70 mass%, 90 mass%, etc.

On the other hand, the upper limit of the content rate of the compound (II) in the colorant (A) may be, for example, 99.9% by mass or less relative to the total amount of the colorant (A), and specific examples thereof may be 99.5% by mass, 99 mass%, 95 mass%, 90 mass%, 80 mass%, 50 mass%, 30 mass%, 10 mass%, etc.

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

The mass ratio of the compound (I) and the fluorescent dye (a) in the colorant (A) can be, for example, 1:99 to 99:1, preferably 20:80 to 80:20, and more preferably 30: 70~70:30. Since the mass ratio of the compound (I) and the fluorescent dye (a) in the colorant (A) is within the above range, heat resistance and fluorescence intensity are achieved. Tendency to improve easily.

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

The content rate of the colorant (A) in the coloring composition may be, for example, 0.1 mass% or more and 99.9 mass% or less, preferably 0.5 mass% or more and 99 mass%, relative to the total amount of solid components in the coloring composition. or less, more preferably 1 mass % or more and 95 mass % or less, still more preferably 3 mass % or more and 90 mass % or less, still more preferably 10 mass % or more and 80 mass % or less, still more preferably 10 mass % or more and 90 mass % or less. 60 mass % or less, and more preferably 10 mass % or more and 35 mass % or less.

In this specification, "the total amount of solid content in the coloring composition" refers to the total amount of components after removing all solvent components from the coloring composition. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis method such as liquid chromatography or gas chromatography.

<Color(A1)>

The coloring agent (A1) may be a dye or a pigment. As the dye, well-known dyes can be used, and examples thereof include well-known dyes described in the Color Index (published by The Society of Dyers and Colourists) and Dyeing Notes (Shikisensha Co., Ltd.). of dyes. In addition, based on the chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, and hypoxic dyes. Methyl azo dye (azomethine dye), squarylium dye (squarylium dye), acridine dye, styrene dye, coumarin dye, quinoline dye, nitro dye, phthalocyanine dye, perylene dye, etc. These dyes can be used alone or in combination of two or more.

Specifically, dyes with the following dye index (C.I.) numbers can be cited.

C.I. Solvent Yellow (Solvent Yellow) 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167 , 189; C.I. Solvent Red 24, 45, 49, 90, 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 (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 and other 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 (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 (Acid Violet) 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24 , 25, 30, 34, 38, 49, 72, 102; C.I. Acid Blue (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 (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 dye, 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 )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 (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) 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 (Basic Violet) 2; C.I. Basic Red (Basic Red) 9; C.I. Basic Green (Basic Green)1; etc. C.I. basic dye, C.I. Reactive Yellow (Reactive Yellow) 2, 76, 116; C.I. Reactive Orange (Reactive Orange) 16; C.I. Reactive Red (Reactive Red) 36; etc. C.I. Reactive dyes, C.I. Mordant Yellow (Mordant Yellow) 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. 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 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26 , 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes, C.I. Vat Green (Vat Green) 1 and other C.I. vat dyes, etc.

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

As the pigment, well-known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). These may be used individually or in combination of 2 or more types.

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 pigments; 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.

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

When the colorant (A) further contains the colorant (A1), the content rate of the total amount of the compound (I) and the compound (II) in the colorant (A) relative to the total amount of the colorant (A) The lower limit is usually 1 mass% or more, preferably 2 mass% or more, more preferably 10 mass% or more, further preferably 25 mass% or more, and particularly preferably 50 mass% or more. On the other hand, the upper limit of the content rate of the total amount of compound (I) and compound (II) in colorant (A) is usually less than 100 mass % with respect to the total amount of colorant (A).

When the colorant (A) further contains the colorant (A1), the content rate of the colorant (A) in the coloring composition is usually 0.1 mass % or more relative to the total amount of solid content in the coloring composition. 99 mass % or less, for example, 0.1 mass % or more and 90 mass % or less, preferably 0.5 mass % or more and 80 mass % or less, more preferably 0.7 mass % or more and 70 mass % or less, particularly preferably 1 mass % More than 60% by mass.

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

The content rate of the solid content in the colorant-containing liquid is preferably 0.01 mass % or more and 99.99 mass % or less, more preferably 0.1 mass % or more and 99.9 mass % or less, and even more preferably 0.1 mass % or more and 99 mass % or less, particularly preferably 1 mass % or more and 90 mass % or less, still more preferably 1 mass % or more and 60 mass % or less, still more preferably 3 mass % or more and 50 mass % or less. , particularly good is 3 mass% or more and 30 mass% or less, and excellent is 5 mass% or more and 30 mass% or less.

The content rate of the colorant (A) in the colorant-containing liquid is usually less than 100% by mass based on the total amount of solid content in the colorant-containing liquid, and is preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.01 mass % or more and 99 mass % or less, more preferably 0.1 mass % or more and 99 mass % or less, particularly preferably 1 mass % or more and 99 mass % or less, still more preferably 2 mass % or more and 99 mass % or less.

In this specification, "the total amount of solid content in the colorant-containing liquid" refers to the total amount of components after removing the solvent (E) from the colorant-containing liquid. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis method such as liquid chromatography or gas chromatography.

The colorant (A1) can be brought into a state in which the colorant (A1) is uniformly dispersed in the liquid containing the colorant (A1) by containing a dispersant and performing a dispersion treatment. The colorant (A1) may be dispersed individually, or may be mixed and dispersed.

Examples of the dispersing agent include surfactants, and the dispersing agent may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specific examples thereof include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. As a dispersant, if expressed by a trade name, examples include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyeisha Chemical Co., Ltd.), Solsperse ( Registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Co., Ltd.), Ajisper (registered trademark) (Ajizhi Disperbyk (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by BYK-chemie Co., Ltd.), BYK (registered trademark) ) (manufactured by BYK-chemie Co., Ltd.), etc.

In order to prepare the colorant-containing liquid, when a dispersant is used, the usage amount of the dispersant (solid content) is usually 10,000 parts by mass or less, preferably 5,000 parts by mass relative to 100 parts by mass of the colorant (A). parts by mass or less, more preferably 1,000 parts by mass or less, still more preferably 500 parts by mass or less, even more preferably 300 parts by mass or less, still more preferably 100 parts by mass or less, still more preferably 5 parts by mass or more and 100 parts by mass or less, Particularly preferred is 5 parts by mass or more and 50 parts by mass or less. If the dispersant When the usage amount is within the above range, a colorant-containing liquid in a more uniform dispersed state tends 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 acid and unsaturated carboxylic anhydride. A polymer of structural units of body (a)").

The resin (B) preferably has a structural unit derived from a monomer (hereinafter, sometimes referred to as "monomer (b)") having a cyclic ether structure with a carbon number of 2 to 4 and an ethylenically unsaturated bond. , and copolymers of other structural units.

Examples of other structural units include monomers derived from monomers copolymerizable with monomer (a) (which are different from monomer (a) and monomer (b). Hereinafter, they may be referred to as "monomers"). Structural units of monomer (c)"), structural units having ethylenically unsaturated bonds, etc.

Examples of the monomer (a) include: acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; maleic acid, rich Malic acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1, Unsaturated dicarboxylic acids such as 2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid; methyl-5-norbornene-2 ,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxymethylbicyclo[2.2.1 ]Hept-2-ene and 5-carboxylic Bicyclic unsaturated compounds containing carboxyl groups such as ethyl bicyclo[2.2.1]hept-2-ene; carboxylic acid anhydrides such as anhydrides of the unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid; succinic acid mono[ Unsaturated mono[2-(meth)acryloxyethyl] ester and phthalic acid mono[2-(meth)acryloxyethyl] ester and other polyvalent carboxylic acids of two or more species (Meth)acryloxyalkyl] esters; unsaturated acrylic esters containing hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymeth)acrylic acid, etc.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred in terms of copolymerization reactivity or solubility of the obtained resin in an alkaline aqueous solution.

The monomer (b) refers to a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxetane ring, an oxetane ring, and a tetrahydrofuran ring) and A polymerizable compound with ethylenically unsaturated bonds. 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 oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as a “monomer (b1)”); A monomer having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)") and a monomer having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)") Measurement body (b3)"), etc.

Examples of the monomer (b1) include monomers having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1)"). -1)”) and those produced by epoxidation of alicyclic unsaturated hydrocarbons The unitary body of the structure (hereinafter, sometimes referred to as "single body (b1-2)").

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred.

Specific examples of the monomer (b1-1) include: (glycidylmeth)acrylate, β-methylglycidyl (meth)acrylate, and β-ethylglycidyl (meth)acrylate. , glycidyl vinyl ether, vinyl benzyl glycidyl ether, α-methyl vinyl benzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis (glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(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 monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000; Manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; Daicel Co., Ltd. Manufactured by), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Co., Ltd.), represented by formula (BI) Compounds and compounds represented by formula (BII), etc.

[Chemical 18]

[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 with 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 the bond with O]

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

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.

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

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

_{As X} ^{a and} _{_} , *-CH ₂ CH ₂ -O- (* represents the bond with O).

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

Examples of the compound represented by formula (BII) include compounds represented by any one of formula (BII-1) to formula (BII-15). Among them, preferred examples include formula (BII-1), The compounds represented by formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15) are more preferably Compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15) are listed.

Compounds represented by formula (BI) and compounds represented by formula (BII) The compound represented by formula (BI) and the compound represented by formula (BII) may be used individually or in combination. When these are used together, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10: on a molar basis. 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 preferred.

Examples of the monomer (b2) include: 3-methyl-3-methacryloxymethyloxetane, 3-methyl-3-acryloxymethyloxetane Cyclobutane, 3-ethyl-3-methacryloxymethyloxetane, 3-ethyl-3-propenyloxymethyloxetane, 3-methyl -3-Methacryloxyethyloxetane, 3-methyl-3-propenyloxyethyloxetane, 3-ethyl-3-methacryloxyethetane Oxyethyl oxetane, 3-ethyl-3-propenyloxyethyl oxetane, etc.

As the monomer (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloxy group is more preferred.

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.

As the unit body (b), the unit body (b1) is preferred in terms of further improving reliability such as heat resistance and chemical resistance of the obtained color filter. Furthermore, in terms of excellent storage stability of the colored composition, the monomer (b1-2) is more preferred.

Examples of the monomer (c) include: (meth)acrylic acid methyl ester, (meth)ethyl acrylate, (meth)acrylic acid n-butyl ester, (meth)acrylic acid second butyl ester, (meth)acrylic acid ethyl ester, and (meth)acrylic acid ethyl ester. )Tertiary 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 ]decan-8-yl (meth)acrylate, (Meth)acrylic acid tricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 ^2,6 ]decen-8-yl ester, (methyl) Tricyclo[5.2.1.0 ^2,6 ]decene-9-yl acrylate, dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantane (meth)acrylate (Meth)acrylate esters such as allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and benzyl (meth)acrylate ; (meth)acrylates containing hydroxyl groups 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-ene 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(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxy Carbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide Dicarbonyl imine derivatives such as lenimidyl caproate, N-succinimidyl-3-maleimide propionate and N-(9-acridinyl) 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-butan Dienes and other dienes; etc.

Among these, in terms of copolymerization reactivity and heat resistance, styrene, vinyltoluene, (meth)acrylic acid tricyclo[5.2.1.0 ^2,6 ]decan-8-yl ester, ( Meth)acrylic acid tricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 ^2,6 ]decen-8-yl ester, (meth)acrylic acid Tricyclo[5.2.1.0 ^2,6 ]decene-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)acrylyl group. Resins with such structural units can be obtained by The polymer addition of the structural unit of the monomer (a) or the monomer (b) has an ethylenic property on the group that can react with the group possessed by the monomer (a) or the monomer (b). Obtained from monomers of saturated bonds.

Examples of such structural units include: a structural unit obtained by adding glycidyl (meth)acrylate to a (meth)acrylic acid unit; and a structural unit obtained by adding 2-hydroxyethyl (meth)acrylate to a maleic anhydride unit. Structural units and structural units formed by adding (meth)acrylic acid to glycidyl (meth)acrylate units, etc. Moreover, when these structural units have a hydroxyl group, the structural unit which added carboxylic acid anhydride further can also be mentioned as a structural unit which has an ethylenically unsaturated bond.

The polymer having a structural unit derived from the monomer (a) can be produced, for example, by polymerizing the monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, solvent, etc. are not particularly limited, and those commonly used in 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 polymers. The oxide (benzoyl peroxide, etc.) may be used as a solvent as long as it dissolves each monomer.

In addition, the obtained polymer can be used directly as a solution after the reaction, as a concentrated or diluted solution, or as a solid (powder) taken out by reprecipitation or the like.

If necessary, a reaction catalyst (such as tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (such as hydroquinone, etc.) of carboxylic acid or carboxylic anhydride and cyclic ether may be used.

Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, and 3,4,5,6-tetrahydrophthalic anhydride. benzene Dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. .

Specific examples of the resin (B) include: (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[ 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, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleyl Imine copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide/(meth)acrylic acid 2-hydroxyethyl ester copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/vinyl toluene copolymer, (meth)acrylic acid 3 ,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/(meth)acrylic acid 2-ethylhexyl copolymer, (meth)acrylic acid 3,4-epoxytricyclo Cycl[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid tricyclo[5.2.1.0 ^2,6 ]decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3 -Methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, Styrene/(meth)acrylic acid copolymer and resins described in Japanese Patent Application Laid-Open Nos. 9-106071, 2004-29518 and 2004-361455, etc.

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

Resin (B) may be a combination of two or more types. In this case, resin (B) preferably contains at least one selected from the group consisting of (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ester/ (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 (meth)acrylic acid 2-hydroxyethyl acrylate copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/vinyl toluene copolymer, (meth)acrylic acid/vinyl toluene copolymer ) One or more types of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably from 1,000 to 100,000, more preferably from 1,000 to 50,000, further preferably from 1,000 to 30,000, particularly preferably from 3,000 to 30,000. the following.

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

The content of the resin (B) in the coloring composition may be, for example, 0.1 mass% or more and 99.9 mass% or less, preferably 0.5 mass% or more and 99 mass% or less, relative to the total amount of solid content in the coloring composition. More preferably, it is 1 mass % or more and 95 mass % or less, further preferably, it is 5 mass % or more and 90 mass % or less, especially 20 mass % or more and 90 mass % or less.

After the colorant-containing liquid is prepared in advance, when the colorant-containing liquid is used to prepare the colored composition of the present invention, the colorant-containing liquid may also contain in advance part or all of the resin (B) described below 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, 10,000 parts by mass or less, preferably 5,000 parts by mass or less, more preferably 1,000 parts by mass or less, based on 100 parts by mass of the colorant (A), and still more preferably The amount is 1 part by mass or more and 500 parts by mass or less, preferably 5 parts by mass or more and 200 parts by mass or less, and still more preferably 10 parts by mass or more and 100 parts by mass or less.

<Implementation Pattern 1>

The colored composition of Embodiment 1 is a colored composition containing a colorant (A) and a resin (B), and the colorant (A) contains the following formula (I-1) The compound represented by and the compound represented by the following formula (II-2).

[Chemistry 21]

<Implementation Pattern 2>

The colored composition of Embodiment 2 is a colored composition containing a colorant (A) and a resin (B), and the colorant (A) contains the following formula (I-2) The compound represented by and the compound represented by the following formula (II-2).

(2) Colored curable resin composition

The colored curable resin composition contains: compound (I), fluorescent dye (a) (hereinafter, these are also collectively referred to as colorant (A)), resin (B), polymerizable compound (hereinafter, sometimes It is called a polymerizable compound (C)), and a polymerization initiator (hereinafter, it may be called 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)), and a solvent (E). One of the groups formed.

The solid content content of the colored composition contained in the colored curable resin composition can be appropriately adjusted according to the chroma, brightness, film thickness, etc. required when curing the colored curable resin composition, and is therefore not particularly limited. , based on the total amount of solid content in the colored curable resin composition, for example, it can be 1 mass % or more and 99 mass % or less, preferably 1 mass % or more and 90 mass % or less, more preferably 2 mass % More than 80% by mass and less than 80% by mass, more preferably more than 3% by mass and less than 70% by mass or less, particularly preferably 4 mass % or more and 60 mass % or less, still more preferably 5 mass % or more and 50 mass % or less, particularly preferably 6 mass % or more and 45 mass % or less, extremely preferably 7 mass % or more and 7 mass % or less. 40% by mass or less.

Each content rate of the colorant (A) in the colored curable resin composition can be appropriately adjusted according to the chroma, brightness, film thickness, etc. required when curing the colored curable resin composition, and is therefore not particularly limited. The total amount of solid content in the curable resin composition may be, for example, 0.1 mass% or more and 99 mass% or less, preferably 1 mass% or more and 90 mass% or less, more preferably 2 mass% or more and 80 mass% % or less, more preferably 3 mass% or more and 70 mass% or less, particularly preferably 4 mass% or more and 20 mass% or less.

In this specification, "the total amount of solid content in the colored curable resin composition" means the total amount of components after removing the solvent (E) from the colored curable resin composition. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis method such as liquid chromatography or gas chromatography. The solid content content in the colored curable resin composition may be, for example, 0.01 mass % or more and less than 100 mass %, preferably 0.1 mass % or more and 99.9 mass %, relative to the total amount of the colored curable resin composition. or less, more preferably 0.1 mass % or more and 99 mass % or less, still more preferably 1 mass % or more and 90 mass % or less, still more preferably 1 mass % or more and 60 mass % or less, still more preferably 3 mass % or more and 90 mass % or less. 50 mass % or less, more preferably 3 mass % or more and 30 mass % or less, particularly preferably 5 mass % or more and 30 mass % or less.

The colored pattern described below formed from the colored curable resin composition of the present invention The pattern or colored coating film not only has excellent heat resistance, but also tends to have high fluorescence intensity at a wavelength of 610 nm. It is preferable to form a colored pattern or colored coating film with a colored curable resin composition containing the fluorescent dye (a) alone. Compared with the film, the fluorescence intensity at the wavelength of 610 nm tends to be higher. The fluorescence intensity can be measured, for example, using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba Manufacturing Co., Ltd.).

<Polymerizable compound (C)>

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

Examples of the polymerizable compound 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., as well as the monomer (a), monomer (b) and monomer (c).

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

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

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 50 or more and 3,500 or less, further preferably 50 or more and 3,000 or less, particularly preferably 150 or more and 2,900 or less, particularly 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 mass % or more and 99 mass % or less, preferably 2 mass % or more and 90 mass % or less, relative to the total solid content. , more preferably 5 mass % or more and 80 mass % or less, further preferably 10 mass % or more and 70 mass % or less, still more preferably 20 mass % or more and 70 mass % or less.

<Polymerization initiator (D)>

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

Examples of the polymerization initiator (D) include: O-acyl oxime compounds, phenyl alkanes Ketone compounds, biimidazole compounds, triazine compounds and acylphosphine oxide compounds, etc.

Examples of O-benzyl oxime compounds include N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine and N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine. Oxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)-3-cyclo Pentylpropane-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-dioxolylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzyl)-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, etc. In addition, as the O-acyl oxime compound, Irgacure OXE01 and OXE02 (above, manufactured by BASF Co., Ltd.) and N-1919 (manufactured by ADEKA Co., Ltd.) can also be used. and other commercially available products. Among them, the O-acyl oxime compound is preferably selected from the group consisting of N-benzoyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine, N-benzene Formyloxy-1-(4-phenylmercaptophenyl)octane-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.

Examples of phenylalkyl ketone compounds include: 2-methyl-2-morpholinyl-1-(4-methylmercaptophenyl)propan-1-one, 2-dimethylamino-1-(4 -Morpholinylphenyl)-2-benzyl Butane-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane- 1-Keto etc. As the phenylalkyl ketone compound, commercially available products such as Irgacure 369, 907, and 379 (above, manufactured by BASF Co., Ltd.) can also be used.

Examples of the phenylalkyl ketone compound include: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy hydroxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one oligomer, α,α-diethoxyacetophenone and benzyldimethyl 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'-tetrakis(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, refer to Japanese Patent Publication No. Sho 48-38403, Japanese Patent Laid-Open No. Sho 62-174204, etc.) and the phenyl group at the 4,4', 5, 5'-position is composed of an alkoxycarbonyl group (carboalkoxy ) substituted biimidazole compounds (for example, refer to Japanese Patent Application Laid-Open No. 7-10913, etc.).

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)vinyl]-1,3, 5-Triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine And 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, 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, and methyl o-benzoyl benzoate. , 4-phenylbenzophenone, 4-benzyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)diphenyl Benzophenone compounds such as methanone and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2- Chloroacridone, benzil, methyl phenylglyoxylate and titanocene compounds, etc.

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

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

The content rate of the polymerization initiator (D) relative to the total amount of all the resin (B) and the polymerizable compound (C) contained in the colored curable resin composition is, for example, It can be 0.01 mass % or more and 40 mass % or less, and is preferably 1 mass % or more and 35 mass % or less.

<Polymerization starting aid (D1)>

The polymerization starting aid (D1) is a compound or a sensitizer for accelerating the polymerization of the polymerizable compound started by the polymerization initiator. When a polymerization initiating aid (D1) is included, it is usually used in combination with a polymerization initiator (D).

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

Examples of the amine compound include: triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and 4-dimethyl 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 and the like, preferably 4,4'-bis(diethylamino)benzophenone. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

Examples of alkoxyanthracene compounds include: 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl- 9,10-diethoxyanthracene, 9,10-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 carboxylic acid compounds include: phenylthioglycolic acid, methylphenylthioglycolic acid, ethylphenylthioglycolic acid, methylethylphenylthioglycolic acid, dimethylphenylmercaptoacetic acid, and methoxyphenylmercaptoacetic acid. Acetic acid, dimethoxyphenylmercaptoacetic acid, chlorophenylmercaptoacetic acid, dichlorophenylmercaptoacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and Naphthoxyacetic acid, etc.

When these polymerization starting aids (D1) are used, the content rate may be, for example, 0.01 mass % or more and 40 mass % or less, relative to the total amount of the resin (B) and the polymerizable compound (C). Preferably, it is 0.1 mass % or more and 30 mass % or less.

<Solvent(E)>

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

Examples of the ester solvent 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 acetate acetate, Ethyl acetate acetate, Ring 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, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether , propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol di Methyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenylethyl ether and methyl anisole, etc.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethoxyethyl acetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, 2-methoxypropylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol mono Ethyl 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 acid 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, and 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 aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene. wait.

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

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

The content rate of the solvent (E) is usually 99.99 mass% or less, preferably 0.1 mass% or more and 99.9 mass% or less, more preferably 1 mass% or more and 99.9 mass% with respect to the total amount of the colored curable resin composition. or less, more preferably 10 mass % or more and 99 mass % or less, particularly preferably 40 mass % or more and 99 mass % or less, still more preferably 50 mass % or more and 97 mass % or less, particularly preferably 70 mass % or more and 97 mass % or less. 97 mass% or less, and excellent is 70 mass% or more and 90 mass% or less.

The colored curable resin composition of the present invention can also be used after dispersing all or a part of the compound (I) and the fluorescent dye (a) in all or a part of the solvent (E) to prepare a colorant-containing liquid. The agent contains liquid to prepare.

The content rate of the solid content in the colorant-containing liquid relative to the total amount of the colorant-containing liquid can be, for example, 0.01 mass % or more and 99.99 mass % or less, preferably 0.1 mass % or more and 99.9 mass % or less, and more preferably 0.1 mass % or more and 99 mass % or less, more preferably 1 mass % or more and 90 mass % or less, more preferably 1 mass % or more and 60 mass % or less, still more preferably 3 mass % or more and 50 mass % or less, Particularly preferred is 3 mass% or more and 30 mass% or less.

The total content rate of the compound (I) and the fluorescent dye (a) in the colorant-containing liquid can be, for example, 0.0001 mass% or more, preferably 0.01 mass% or more, based on the total solid content in the colorant-containing liquid. More preferably, it is 1 mass % or more, and still more preferably It is 5 mass % or more, more preferably 10 mass % or more, still more preferably 15 mass % or more. On the other hand, the upper limit of the total content rate of compound (I) and compound (II) in the colorant-containing liquid is usually less than 100% by mass, and may be, for example, 99% by mass based on the total amount of solid content in the colorant-containing liquid. the following.

When preparing a colorant-containing liquid by dispersing all or a part of the compound (I) and the fluorescent dye (a) in all or a part of the solvent (E), the colorant-containing liquid can be prepared by previously containing all or a part of the resin (B). to further improve the dispersion stability of the colorant-containing liquid. The content of the resin (B) in the colorant-containing liquid may be, for example, 10,000 parts by mass or less, preferably 5,000 parts by mass or less, and more preferably 1,000 parts by mass relative to 100 parts by mass of the compound (I) and the fluorescent dye (a) in total. Parts by mass or less, more preferably 1 part by mass or more and 500 parts by mass or less, particularly preferably 5 parts by mass or more and 200 parts by mass or less, still more preferably 10 parts by mass or more and 100 parts by mass or less.

Compound (I) and fluorescent dye (a) can also be subjected to rosin treatment, surface treatment using derivatives introducing acidic groups or basic groups, etc., and compound (I) and fluorescent dyes using polymer compounds, etc. if necessary. Grafting treatment on the surface of dye (a), micronization treatment using sulfuric acid micronization method, etc., cleaning treatment using organic solvents or water, etc. to remove impurities, removal treatment of ionic impurities using ion exchange method, etc., etc. . The particle diameters of compound (I) and fluorescent dye (a) are preferably substantially uniform.

The compound (I) and the fluorescent dye (a) can be brought into a state in which the compound (I) and the fluorescent dye (a) are uniformly dispersed in the colorant-containing liquid by containing a dispersant and performing a dispersion treatment. The compound (I) and the fluorescent dye (a) can be dispersed separately, or a plurality of them can be mixed and dispersed. By colorant(A) By including the compound (I), the fluorescent dye (a) and the dispersant, the dispersibility of the compound (I) is improved and the heat resistance tends to be easily improved.

Examples of the dispersing agent include surfactants, and the dispersing agent may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specific examples thereof include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. As a dispersant, if expressed by a trade name, examples include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyeisha Chemical Co., Ltd.), Solsperse ( Registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Co., Ltd.), Ajisper (registered trademark) (Ajizhi Disperbyk (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), BYK (registered trademark) (manufactured by BYK-chemie Co., Ltd.) ) (manufactured by BYK-chemie Co., Ltd.), etc.

When a dispersant is used, the usage amount of the dispersant (solid content) is 10,000 parts by mass or less, preferably 5,000 parts by mass or less, based on 100 parts by mass of the compound (I) and the fluorescent dye (a) in total. It is preferably 1000 parts by mass or less, more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, still more preferably 100 parts by mass or less, still more preferably 5 parts by mass or more and 100 parts by mass or less, particularly preferably 5 parts by mass. More than 50 parts by mass and less than 50 parts by mass. When the usage amount of the dispersant is within the above range, a colorant-containing liquid in a more uniform dispersed state tends to be obtained.

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

<Leveling agent (F)>

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

Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: Toray Dow Corning (Toray Dow Corning) ); KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Japanese Momentive Advanced Materials (Manufactured by Momentive Performance Materials Japan Co., Ltd.) etc.

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

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

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

<Antioxidant (G)>

From the viewpoint of improving the heat resistance of the colorant, it is preferred to use the antioxidant (G) alone or in combination of two or more antioxidants (G). The antioxidant is not particularly limited as long as it is an antioxidant commonly used in industry. Phenol can be used. Antioxidants, phosphorus antioxidants and sulfur antioxidants, etc.

Examples of the phenolic antioxidant include Irganox 1010 (pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], BASF (manufactured by BASF Co., Ltd.), Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, BASF (manufactured by Co., Ltd.), Irganox 1330: 3,3',3",5,5',5"-hexa-tert-butyl-α,α',α"-(mesitylene -2,4,6-tris-p-cresol, manufactured by BASF Co., Ltd.), Irganox 3114: 1,3,5-tris(3,5-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 Co., Ltd.), Irganox 1035 (Irganox 1035: thiodiethylenebis[3-(3,5-di-tertiary ketone) Butyl-4-hydroxyphenyl)propionate], manufactured by BASF Co., Ltd.), Irganox 1135 (Irganox 1135: phenylpropionic acid, 3,5-bis(1,1-dimethyl Ethyl)-4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF Co., Ltd.), Irganox 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-ortho Cresol, manufactured by BASF Co., Ltd.), Irganox 3125 (manufactured by BASF Co., Ltd.), Irganox 565 (Irganox 565: 2,4-bis(n-octane) methyl)-6-(4-hydroxy-3',5'-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF Co., Ltd.), Eddie Costabo (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-tetraxaspiro(5,5)eleven alkane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (manufactured by Sumitomo Chemical Co., Ltd.) ), Sumilizer GS (manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec Co., Ltd.) and Vitamin E (Eisai) (stock) manufacturing), 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: Tris[2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6 -yl]oxy]ethyl]amine, manufactured by BASF Co., Ltd., Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl) phosphorous acid) -6-Methylphenyl)ethyl ester, manufactured by BASF Co., Ltd.), Adekastab 329K (manufactured by ADEKA Co., Ltd.), Adekastab ( Adekastab) PEP36 (manufactured by ADEKA Co., Ltd.), Adekastab PEP-8 (manufactured by ADEKA Co., Ltd.), Sandstab P- EPQ (Clariant), Weston 618 (Weston 618, GE), Weston 619G (Weston 619G, GE), Ultranox 626 (Ultranox 626, GE) Manufacturing) and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra -Third-butyldibenzo[d,f][1.3.2]dioxaphosphepine) (manufactured by Sumitomo Chemical Co., Ltd.), etc.

Examples of the sulfur-based antioxidant include dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate. Acid dialkyl ester compounds and 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 optionally contain additives known in the technical field such as fillers, other polymer compounds, adhesion accelerators, light stabilizers, and chain transfer agents.

Examples of the close contact accelerator include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, and 3-glycidyloxypropyltrimethoxysilane. silane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethyl Oxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyl Trimethoxysilane, 3-mercapto(sulfanyl)propyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldi Methoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane Silane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.

<Production method of colored curable resin composition>

The colored curable resin composition can be further patterned by, for example, the colorant (A), the resin (B), the solvent (E), and the leveling agent (F) using photolithography. In the first step, the polymerizable compound (C), polymerization initiator (D), polymerization initiating assistant (D1) and other ingredients are mixed together to prepare.

The coloring curable resin composition can also be prepared by mixing the coloring agent (A) with the resin (B) and the solvent (E), and then polymerizing the coloring composition with the polymerizable compound (C). The initiator (D), polymerization starting aid (D1) and other ingredients are mixed and prepared. It is preferred to mix the colorant (A) with part or all of the solvent (E) in advance and disperse it using a bead mill or the like. Until the average particle diameter of the pigment becomes approximately 0.2 μm or less. At this time, part or all of the pigment dispersant and resin (B) may be prepared as necessary. By mixing the remaining components into the pigment dispersion obtained in this manner so as to have a predetermined concentration, the target colored curable resin composition can be prepared.

The dye may be dissolved in part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter this solution with a filter having a pore diameter of about 0.01 μm or more and 1 μm or less.

It is preferable to filter the mixed colored curable resin composition with a filter having a pore diameter of about 0.1 μm or more and 10 μm or less.

(3)Color filter

A color filter can be formed from the colored curable resin composition of the present invention. Examples of methods for forming a colored pattern include photolithography, inkjet, and printing. Among them, photolithography is preferred. The photolithography method is to apply the colored curable resin composition on a substrate, dry it to form a colored curable resin composition layer, and expose the colored curable resin composition layer through a light mask. Light and development methods. In the photolithography method, by not using a photomask during exposure and/or not performing development, 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 thus formed is the color filter of the present invention.

The film thickness of the produced color filter is not particularly limited and can be appropriately adjusted depending on the purpose or use. 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 still more preferably 0.5 μm or more and 30 μm or less. Below 6μm.

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

The formation of pixels of various colors using photolithography can be performed by known or conventional devices or conditions. For example, it can be produced as follows.

First, the colored curable resin composition is applied to a substrate, and is heated and dried (prebaked) and/or dried under reduced pressure to remove volatile components such as solvents and dry them to obtain smooth colored curable properties. Resin composition layer.

Examples of coating methods include spin coating, slit coating, slit and spin coating, and the like.

The temperature during heat drying is preferably from 30°C to 120°C, more preferably from 50°C to 110°C. In addition, the heating time is preferably not less than 10 seconds and not more than 60 minutes, more preferably not less than 30 seconds and not more than 30 minutes.

When drying under reduced pressure is performed, it is preferably performed under a pressure of 50 Pa or more and 150 Pa or less and in a temperature range of 20° C. or more and 25° C. 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 target 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 photomask 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 equipment such as stepper.

As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less may be used. For example, you can also use a filter that cuts off the wavelength range of less than 350 nm, or you can use a band pass filter that cuts out the light in those wavelength ranges near 436 nm, 408 nm, and 365 nm. filter) for selective removal. Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.

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

As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferred. The concentration of these basic compounds in the aqueous solution may be, for example, 0.01 mass% or more and 10 mass% or less. Furthermore, the developer may contain a surfactant.

The development method may be any one of liquid coating method, dipping method, spray method, etc. Furthermore, the substrate can be tilted to any angle during development.

The developed substrate is preferably washed with water.

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

(4)Display device

The color filter is used as a color filter used in display devices (for example, liquid crystal display devices, organic electroluminescence (EL) devices, electronic paper, etc.) and solid-state imaging elements. Among them, as a color filter used in organic EL Useful for color filters used in devices.

[Example]

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the present invention is not limited at all by the following Examples. Of course, the present invention can also be implemented with appropriate modifications within the scope that is suitable for the gist described and described later. These are all included in the technical scope of the present invention. In addition, in the following, unless otherwise specified, "part" means "mass part" and "%" means "mass %".

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

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

Device: HLC-8120GPC (manufactured by Tosoh Corporation)

Column: TSK-GELG2000HXL

Tube string temperature: 40℃

Solvent: Tetrahydrofuran

Flow rate: 1.0mL/minute

Solid content concentration of analysis sample: 0.001 mass%~0.01 mass%

Injection volume: 50μL

Detector: refractive index (RI)

Calibration standard materials: TSK standard polystyrene (STANDARD POLYSTYRENE) F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

The ratio (Mw/Mn) of the obtained polystyrene-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) was defined as the degree of dispersion.

Synthesis example 1

Added 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.7 parts of 6-aminoundecane (manufactured by Tokyo Chemical Industry Co., Ltd.), and zinc acetate (Kanto Chemical Co., Ltd.) 1.3 parts and 314 parts of imidazole (Tokyo Chemical Industry Co., Ltd.) were stirred at 150° C. for 3 hours. While maintaining the obtained mixture at 20° C. or below, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1,300 parts of water were added, 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 12 parts of the compound represented by formula (I-1) (yield 87%).

[Chemical 25]

<Identification of Compound I-1>

(Mass analysis) Ionization mode=ESI+: m/z=[M+H] ⁺ 699

Exact Mass: 698

Synthesis example 2

Added 8.0 parts of 3,4,9,10-perylenetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of 7-aminotridecane (manufactured by Tokyo Chemical Industry Co., Ltd.), and zinc acetate (Kanto Chemical Co., Ltd.) 1.3 parts and 314 parts of imidazole (Tokyo Chemical Industry Co., Ltd.) were stirred at 150° C. for 3 hours. While maintaining the obtained mixture at 20° C. or below, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 1,300 parts of water were added, 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 12 parts of the compound represented by formula (I-2) (yield 79%).

[Chemical 26]

<Identification of Compound I-2>

(Mass analysis) Ionization mode=ESI+: m/z=[M+H] ⁺ 755

Exact Mass: 754

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

Synthesis example 3

Add 10 parts of 1,6,7,12-tetrachloro-3,4,9,10-perylic dianhydride (manufactured by Combinatorial Chemistry Co., Ltd.) and 2,6-diisopropylaniline (Tokyo (manufactured by Chemical Industry Co., Ltd.) and 188 parts of propionic acid, and stirred under reflux for 20 hours. While maintaining the obtained mixture at 20° C. or lower, 50 parts of water was added, resulting in an orange precipitate. For mixtures containing the orange precipitate Filter, and wash the filtered residue with 200 parts of water and 100 parts of methanol. The obtained residue was dried under reduced pressure at 60° C. to obtain 12 parts of an intermediate compound (INT) (yield 75%).

<Identification of compound INT>

(Mass analysis) Ionization mode=ESI+: m/z=[M+H] ⁺ 847.9

Exact Mass: 848.6

Added 5.0 parts of manufactured INT, 1.5 parts of 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.1 parts of 4-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), and potassium carbonate (manufactured by Kanto Chemical Co., Ltd. ), and 295 parts of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Ltd.), and stirred at 130°C for 13 hours. While keeping the obtained mixture at 20° C. or below, 29 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 142 parts of water were added. As a result, a dark red precipitate was generated. The mixture containing the dark red precipitate was filtered, and the filtered residue was washed with 300 parts of water and 150 parts of methanol. The obtained residue was dried under reduced pressure at 60° C. to obtain 6.1 parts of the compound represented by formula (II-92) (yield 81%).

<Identification of Compound II-92>

(Mass analysis) Ionization mode=ESI+: m/z=[M+H] ⁺ 1237.8

Exact Mass: 1236.8

Synthesis example 4

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

[Chemical 30]

<Example 1>

(1) Preparation of coloring composition

Each component was mixed in the following ratio to obtain a colored composition 1.

(2) Preparation of colored curable resin composition

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

Coloring composition 1 478 parts

(C) Polymerizable compound: dipentaerythritol hexaacrylate

(KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 copies

(D) Polymerization initiator: N-benzyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; BASF

(manufactured by BASF) 2 copies

(F) Leveling agent: polyether modified silicone oil (Toray Silicone)

SH8400: Toray Dow Corning (Toray Dow Corning Co., Ltd.) 0.15 share

(3) Production of colored coating film

On a 5 cm square glass substrate (Eagle XG; manufactured by Corning Corporation), the colored curable resin composition is applied by spin coating so that the film thickness after baking becomes 1.7 μm to 2 μm. Then, it was prebaked at 100°C for 3 minutes to form a colored curable resin composition layer. After leaving it to cool, the colored curable resin composition layer formed on the substrate was exposed using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) at an exposure dose of 80 mJ/cm ² (365 nm) in an atmospheric environment. standard) for light irradiation. After light irradiation, post-baking is performed in an oven at 230° C. for 30 minutes to obtain a colored coating film.

(4)Heat resistance test

The xy chromaticity coordinates (x, y) and Y of the obtained colored coating film were measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS Corporation). In an oven, the colored coating film after measurement was heated at 230°C for 120 minutes in an air environment. The xy chromaticity coordinates (x, y) and Y after heating (at 230° C. for 120 minutes) were measured using a colorimeter. The color difference ΔE*ab was calculated based on the measured values before and after heating using the method described in Japanese Industrial Standards (JIS) Z 8730: 2009 (7. Calculation method of color difference).

In addition, a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba Manufacturing Co., Ltd.) (excitation side slit 5, fluorescence side slit 10, excitation wavelength 460 nm) was used to measure the addition. Fluorescence intensity of the colored curable resin composition film before heating (at 230° C. for 120 minutes). The fluorescence intensity at a wavelength of 610 nm was determined, and the ratio to the fluorescence intensity before heating in Comparative Example 1 was determined. The results are shown in Table 7.

Furthermore, a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba Manufacturing Co., Ltd.) (excitation side slit 5, fluorescence side slit 10, excitation wavelength 460 nm) was used to measure the temperature after heating (at 230° C. for 120 minutes). The fluorescence intensity of the colored curable resin composition film. The fluorescence intensity at a wavelength of 610 nm was determined, and the ratio to the fluorescence intensity after heating in Comparative Example 1 was determined. The results are shown in Table 7.

<Example 2>

Colored curable resin composition 2 was obtained in the same manner as in Example 1, except that the compound (I-2) was used instead of the compound (I-1) to prepare a colorant. The results are shown in Table 7.

<Example 3>

Colored curable resin composition 3 was obtained in the same manner as in Example 1 except that the compound (II-92) was used instead of the compound (II-2) to prepare a colorant.

The results are shown in Table 7.

<Example 4>

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

<Example 5>

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

<Comparative example 1>

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

<Comparative example 2>

The colored curable resin composition was obtained in the same manner as in Example 1 except that the compound (II-2) was changed from 2.6 parts to 3.9 parts and the colorant was prepared without using the compound (I-1). Object 7. The results are shown in Table 7.

<Comparative Example 3>

Colored curable resin composition 8 was obtained in the same manner as in Example 1, except that Coumarin 545T (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of compound (I-1) to prepare a colorant. The results are shown in Table 7.

<Comparative Example 4>

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

[Table 7]

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

Claims (5)

A colored curable resin composition comprising: a compound represented by the following formula (I), a fluorescent dye, a resin, a polymerizable compound, a polymerization initiator, and a solvent;

[In the formula (I), R ¹ to R ⁴ independently represent an alkyl group having 5 to 10 carbon atoms; R ⁵ to R ¹² independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a hydrogen atom, Halogen atom, or nitro group]. The colored curable resin composition described in claim 1, wherein the fluorescent dye is a compound having a different structure from the compound represented by the formula (I) and is a red fluorescent dye. The colored curable resin composition as described in item 2 of the patent application, wherein the red fluorescent dye is a compound represented by the following formula (II);

[In formula (II), Ar ¹ to Ar ⁶ independently represent an aryl group that may have a substituent; R ¹⁵ to R ¹⁸ independently represent a hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom, or a halogen that may have a substituent. atom, or nitro]. A color filter formed from the colored curable resin composition described in Item 1 of the patent application. A display device includes the color filter as described in item 4 of the patent application.