JP2015131937A - Coloring compositions - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide coloring compositions excellent in sensitivity and heat resistance and suitable for a cover glass integrated touch panel, a display device color filter, a liquid-crystal display panel and an organic EL display panel.SOLUTION: A coloring composition contains a latent antioxidant (A) and a coloring agent (B). Preferably, the coloring composition further contains a solvent (C), a resin (D) and/or a photopolymerizable unsaturated monomer (E). Further, it is also preferable that the latent antioxidant (A) is a compound represented by the general formula (I). (In the formula, A, R, R, R, n, d, k and Xare as defined in the specification.)

Description

  The present invention relates to a colorable composition containing a latent antioxidant.

  The coloring composition contains a pigment, a solvent, a dispersant, a photopolymerizable unsaturated compound, a photopolymerization initiator, and the like. Since the coloring composition containing a photopolymerization initiator can be polymerized and cured by irradiation with ultraviolet rays or an electron beam, it is useful for a filter segment constituting a color filter. The filter segment is formed by applying a photosensitive material to a glass substrate or the like, drying and removing excess solvent, and then irradiating with an active energy ray by exposure through a photomask for pixel formation, and curing (negative type) or It is formed by increasing the alkali solubility (positive type), removing the portion that is dissolved with an alkali solution, and heating to 230 ° C. or higher, which is post-baking.

  In recent years, high definition of display panels has been strongly demanded, reflecting the high quality of color imaging devices and color liquid crystal televisions, and materials with high sensitivity are being studied for high definition. However, if the components such as photopolymerization initiator and photopolymerizable monomer are increased in order to improve photocurability, yellowing occurs in the post-baking process at 230 ° C. or higher, and the brightness of the filter segment is reduced. There is a problem of becoming a factor.

In the following Patent Documents 1 to 4, the use of various antioxidants such as hindered phenolic antioxidants in the photosensitive resin composition used for forming the filter segment is studied.
However, using only these antioxidants is not sufficient to suppress yellowing in the post-baking process, and furthermore, when using the hindered phenol-based antioxidant, it suppresses photocuring. It has been difficult to make high-definition color filters.

JP 2010-276704 A JP 2011-57974 A JP 2011-99918 A JP2013-134321A

  Accordingly, an object of the present invention is to provide a coloring composition which is excellent in sensitivity and heat resistance and can obtain an appropriate pattern shape and fine pattern.

  As a result of intensive studies, the present inventors have found that a coloring composition containing a latent antioxidant (A) and a coloring agent (B), particularly a resin (D), a photopolymerizable unsaturated monomer. It has been found that a coloring composition to which a monomer (E) and a photopolymerization initiator (G) are added can achieve the above-mentioned purpose, and the coloring composition can be applied to a cover glass integrated touch panel and a color filter. As a result, the present invention was reached.

  Moreover, this invention provides the pigment paste using the said coloring composition.

  Moreover, this invention provides the cover glass integrated touch panel using the said coloring composition.

  Moreover, this invention provides the color filter using the said coloring composition.

  According to the present invention, the colorable composition containing the latent antioxidant is excellent in sensitivity and heat resistance. The cured product is suitable for a cover glass integrated touch panel, a color filter for a display device, a liquid crystal display panel, and an organic EL display panel.

  Hereinafter, the coloring composition of the present invention will be described based on preferred embodiments.

  The coloring composition of the present invention contains a latent antioxidant (A) and a coloring agent (B). Hereinafter, each component will be described in order.

<Latent antioxidant (A)>
The latent antioxidant (A) used in the coloring composition of the present invention is inactive in the prebaking step at room temperature or 150 ° C. and is heated at 100 to 250 ° C., or an acid / base catalyst is present. Under heating at 80 to 200 ° C., the protecting group is removed and becomes active. As the latent antioxidant (A), those represented by the following general formula (I) are preferable because synthesis is easy.

（式中、Ａは、五員環又は六員環の脂環、芳香環又は複素環を表し、
Ｒ^１及びＲ^２は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数１〜４０のアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアリールアルキル基又は炭素原子数２〜２０の複素環含有基を表し、
Ｒ^４は、炭素原子数１〜２０のアルキル基、炭素原子数２〜２０のアルケニル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアリールアルキル基、炭素原子数２〜２０の複素環含有基又はトリアルキルシリル基を表し、
Ｒ^１、Ｒ^２及びＲ^４で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素−炭素二重結合、−Ｏ−、−Ｓ−、−ＣＯ−、−Ｏ−ＣＯ−、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｏ−、−Ｓ−ＣＯ−、−ＣＯ−Ｓ−、−Ｓ−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｓ−、−ＣＯ−ＮＨ−、−ＮＨ−ＣＯ−、−ＮＨ−ＣＯ−Ｏ−、−ＮＲ^’−、＞Ｐ＝Ｏ、−Ｓ−Ｓ−又は−ＳＯ_２−から選ばれた基の１種又は２種以上の組み合わせで置き換わっていてもよく、Ｒ’は、水素原子又は炭素原子数１〜８のアルキル基を表し、
複数のＲ^２同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のＲ^２及びＲ^４はそれぞれ同じでも異なっていてもよく、
ｎは、１〜１０の整数を表し、
ｄは、１〜３の整数を表し、
ｋは、１〜３の整数を表し、
Ｘ^１は、直接結合、窒素原子、酸素原子、硫黄原子、リン原子、下記式（Ｉ−２）で表される基、＞Ｐ＝Ｏ、＞Ｃ＝Ｏ、−ＮＨ−ＣＯ−、−ＣＯ−ＮＨ−、＞ＮＲ¹⁰、＞ＰＲ¹⁰、−ＯＲ¹⁰、−ＳＲ¹⁰、−ＮＲ¹⁰Ｒ¹¹若しくは−ＰＲ¹⁰Ｒ¹¹又はｎと同数の価数を有する置換基を有していてもよい炭素原子数１〜１２０の脂肪族炭化水素基、置換基を有していてもよい炭素原子数６〜３５の芳香環含有炭化水素基若しくは置換基を有していてもよい炭素原子数２〜３５の複素環含有基を表し、Ｒ¹⁰及びＲ¹¹は、水素原子、置換基を有していてもよい炭素原子数１〜３５の脂肪族炭化水素基、置換基を有していてもよい炭素原子数６〜３５の芳香環含有炭化水素基又は置換基を有していてもよい炭素原子数２〜３５の複素環含有基を表し、該脂肪族炭化水素基、芳香環含有炭化水素基及び複素環含有基中のメチレン基は、炭素−炭素二重結合、−Ｏ−、−Ｓ−、−ＣＯ−、−Ｏ−ＣＯ−、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｏ−、−Ｓ−ＣＯ−、−ＣＯ−Ｓ−、−Ｓ−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｓ−、−ＣＯ−ＮＨ−、−ＮＨ−ＣＯ−、−ＮＨ−ＣＯ−Ｏ−、−ＮＲ^’−、＞Ｐ＝Ｏ、−Ｓ−Ｓ−、−ＳＯ_２−又は窒素原子から選ばれた基の１種又は２種以上の組み合わせで置き換わっていてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。但し、Ｘ^１が窒素原子、リン原子又は下記式（Ｉ−２）で表される基の場合、ｎは３であり、Ｘ^１が酸素原子又は硫黄原子の場合、ｎは２であり、Ｘ^１が直接結合、＞Ｐ＝Ｏ、＞Ｃ＝Ｏ、−ＮＨ−ＣＯ−、−ＣＯ−ＮＨ−、＞ＮＲ¹⁰又は＞ＰＲ¹⁰の場合、ｎは２であり、Ｘが−ＯＲ¹⁰、−ＳＲ¹⁰、−ＮＲ¹⁰Ｒ¹¹又は−ＰＲ¹⁰Ｒ¹¹の場合、ｎが１であり、Ｘ^１は、Ａと一緒になって環を形成していてもよい。）

(In the formula, A represents a 5-membered or 6-membered alicyclic, aromatic or heterocyclic ring;
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms An aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms;
R ⁴ is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to 2 carbon atoms. Represents 20 heterocycle-containing groups or trialkylsilyl groups,
The methylene group in the alkyl group or arylalkyl group represented by R ¹ , R ² and R ⁴ is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, — CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-,- CO-NH -, - NH- CO -, - NH-CO-O -, - NR '-,> P = O, -S-S- or -SO ₂ - 1 kinds of groups selected from or two R ′ may represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
A plurality of R ² may be bonded to each other to form a benzene ring or a naphthalene ring,
The plurality of R ² and R ⁴ may be the same or different,
n represents an integer of 1 to 10,
d represents an integer of 1 to 3,
k represents an integer of 1 to 3,
X ¹ is a direct bond, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following formula (I-2),>P═O,> C═O, —NH—CO—, —CO ^{-NH -,> NR 10,>} PR 10, -OR 10, -SR 10, which may have a -NR ¹⁰ R ¹¹ or -PR ¹⁰ R ^11, or n as many substituents having valence carbon C1-C120 aliphatic hydrocarbon group, C6-C35 aromatic ring-containing hydrocarbon group which may have a substituent or C2-C35 which may have a substituent Wherein R ¹⁰ and R ¹¹ are a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an optionally substituted carbon. Represents an aromatic ring-containing hydrocarbon group having 6 to 35 atoms or a heterocycle-containing group having 2 to 35 carbon atoms which may have a substituent. The methylene group in the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocyclic ring-containing group is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO. -O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO One of a group selected from —NH—, —NH—CO—, —NH—CO—O—, —NR ^′ —,> P═O, —S—S—, —SO ₂ — or a nitrogen atom; Two or more combinations may be substituted, and the aromatic ring or the heterocyclic ring may be condensed with another ring. However, if the group X ¹ is represented by a nitrogen atom, phosphorus atom or the following formula (I-2), n is 3, when X ¹ is an oxygen atom or a sulfur atom, n is 2, X ^{When 1} is a direct bond,>P═O,> C═O, —NH—CO—, —CO—NH—,> NR ¹⁰ or> PR ¹⁰ , n is 2, X is —OR ¹⁰ , — In the case of SR ¹⁰ , —NR ¹⁰ R ¹¹ or —PR ¹⁰ R ¹¹ , n is 1 and X ¹ may be combined with A to form a ring. )

Latent antioxidant represented by the above general formula (I), a particular atom or group of valence n which is represented by X ^1, having a structure in which n-number of a particular group is bonded. The n groups may be the same as or different from each other. The value of n is 1 to 10, and preferably 2 to 6 from the viewpoint of ease of synthesis.

Examples of the five-membered alicyclic ring represented by A in the general formula (I) include cyclopentyl, examples of the five-membered aromatic ring include cyclopentadiene, ferrocene, and the like, and a five-membered heterocyclic ring. Examples include furan, thiophene, pyrrole, pyrrolidine, pyrazolidine, pyrazole, imidazole, imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazole, isothiazolidine, and the six-membered alicyclic ring is cyclohexyl. Examples of the six-membered aromatic ring include benzene, naphthalene, anthracene, fluorene, perylene, and pyrene. Examples of the six-membered heterocyclic ring include piperidine, piperazine, morpholine, thiomorpholine, pyridine, Pyrazine, pyrimidine, pyridazine, triazine, etc. These rings may be condensed or substituted with other rings, and examples of the ring formed by the condensation or substitution include quinoline, isoquinoline, indole, urolidine, and benzoxazole. , Benzotriazole, azulene and the like.
Examples of the halogen atom represented by R ¹ and R ² include fluorine, chlorine, bromine and iodine.
Examples of the alkyl group having 1 to 40 carbon atoms represented by R ¹ and R ² and the alkyl group having 1 to 20 carbon atoms represented by R ⁴ include methyl, ethyl, propyl, iso-propyl, butyl, sec -Butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, adamantyl and the like,
Examples of the alkoxy group having 1 to 40 carbon atoms represented by R ¹ and R ² include methyloxy, ethyloxy, iso-propyloxy, butyloxy, sec-butyloxy, tert-butyloxy, iso-butyloxy, amyloxy, iso-amyloxy Tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, tert-heptyloxy, 1-octyloxy, iso-octyloxy, tert-octyloxy and the like,
R ¹ and 1 to 40 carbon atoms represented by ^{R 2} alkyl and alkoxy groups and aryl groups having 6 to 20 carbon atoms, arylalkyl groups and having 2 to 20 carbon atoms having 7 to 20 carbon atoms Examples of the substituent for substituting the heterocyclic group include ethylenically unsaturated groups such as vinyl, allyl, acrylic and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, Acyl groups such as acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl; Acetyl Acyloxy groups such as xyl and benzoyloxy; amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino , Naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, Morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octa Substituted amino groups such as decyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N, N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino; sulfonamide Group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, carbamoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group or carboxyl group, sulfo group, phosphonic acid group, Examples thereof include salts of phosphoric acid groups.
Examples of the alkenyl group having 2 to 20 carbon atoms represented by R ⁴ include vinyl, allyl, butenyl, propenyl and the like.
Examples of the aryl group having 6 to 20 carbon atoms represented by R ¹ , R ² and R ⁴ include phenyl, naphthyl, anthracenyl and the like,
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R ¹ , R ² and R ⁴ include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl group, etc.
Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R ¹ , R ² and R ⁴ include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, Triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidine-3-yl and the like,
Examples of the trialkylsilyl group represented by R ⁴ include trimethylsilane, triethylsilane, and ethyldimethylsilane.

The monovalent aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have the substituent represented by X ¹ in the general formula (I), and the substituent represented by R ¹⁰ and R ¹¹ Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have, for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, sec-butyl, isobutyl, amyl, isoamyl , Tertiary amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, first Alkyl groups such as trioctyl, 2-ethylhexyl, nonyl, isononyl, decyl; methyloxy, ethyloxy, propyloxy Si, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tert-heptyloxy, n-octyloxy, Alkoxy groups such as isooctyloxy, tert-octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy; methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, sec Triamylthio, hexylthio, cyclohexylthio, heptylthio, isoheptylthio, tertiary heptylthio, n-octylthio, isooctylthio, tertiary octylthio, -An alkylthio group such as ethylhexylthio; vinyl, 1-methylethenyl, 2-methylethenyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4- Alkenyl groups such as hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, tricosenyl, etc.
Examples of the divalent to 10-valent aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent represented by X ¹ include the groups exemplified as the monovalent aliphatic hydrocarbon group described above. And divalent to 10-valent groups corresponding to.
Examples of the monovalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms that may have a substituent represented by X ¹ and R ¹⁰ and R ¹¹ in the general formula (I) include benzyl, phenethyl, Arylalkyl groups such as diphenylmethyl, triphenylmethyl, styryl and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio;
Examples of the divalent to 10-valent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent represented by X ¹ are exemplified as the above-mentioned monovalent aromatic ring-containing hydrocarbon group. Examples thereof include divalent to 10-valent groups corresponding to the groups.
Examples of the monovalent heterocyclic-containing group having 2 to 35 carbon atoms which may have a substituent represented by X ¹ and R ¹⁰ and R ¹¹ in the general formula (I) include pyridyl, pyrimidyl, pyridazyl, Piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl , Indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidine-3-yl, benzotriazoyl and the like It is done.
Examples of the divalent to 10-valent heterocycle-containing group having 2 to 35 carbon atoms that may have a substituent represented by X ¹ include the groups exemplified as the monovalent aromatic ring-containing hydrocarbon group described above. Corresponding divalent to 10-valent groups are mentioned.
Examples of the substituent include ethylenically unsaturated groups such as vinyl, allyl, acrylic and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl and phenyl Acyl groups such as carbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl; acetyloxy, benzoyloxy An acyloxy group such as amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, Lorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N , N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxy Carbonylamino, sulfamoylamino, N, N-dimethylaminosulfonylamino, methylsulfonylamino, Substituted amino groups such as rusulfonylamino and phenylsulfonylamino; sulfonamide groups, sulfonyl groups, carboxyl groups, cyano groups, sulfo groups, hydroxyl groups, nitro groups, mercapto groups, imide groups, carbamoyl groups, sulfonamide groups, phosphonic acid groups , Phosphoric acid groups or carboxyl groups, sulfo groups, phosphonic acid groups, salts of phosphoric acid groups, and the like, and these groups may be further substituted. Moreover, the carboxyl group and the sulfo group may form a salt.

  Among the compounds represented by the general formula (I), those represented by the following general formulas (I-3) to (I-5) are preferable because they are easy to synthesize and have high heat resistance.

（式中、環Ａ^２は、六員環の脂環、芳香環又は複素環であり、Ｒ^１１１、Ｒ^１１２、Ｒ^１１３、Ｒ^１１４及びＲ^１１５は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数１〜４０のアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアリールアルキル基、炭素原子数２〜２０の複素環含有基又は−Ｏ−Ｒ^２を表し、Ｒ^１１１、Ｒ^１１２、Ｒ^１１３、Ｒ^１１４及びＲ^１１５のうち少なくとも１つは水素原子でなく、Ｒ^２及びＲ^４は、上記一般式（Ｉ）と同じである。）

(In the formula, ring A ² is a six-membered alicyclic ring, aromatic ring or heterocyclic ring, and R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ and R ¹¹⁵ are a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group. , A nitro group, a carboxyl group, an optionally substituted alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, the number of carbon atoms 2 to 20 heterocycle-containing groups or —O—R ² , wherein at least one of R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ and R ¹¹⁵ is not a hydrogen atom, and R ² and R ⁴ are (Same as general formula (I).)

（式中、Ｘ^１１は、下記一般式（１）で表される基であり、Ｒ^１１６、Ｒ^１１７、Ｒ^１１８及びＲ^１１９は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数１〜４０のアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアリールアルキル基又は炭素原子数２〜２０の複素環含有基を表し、Ｒ^１１６、Ｒ^１１７、Ｒ^１１８及びＲ^１１９のうち少なくとも１つは水素原子でなく、環Ａ^２は、上記一般式（Ｉ−３）と同じであり、Ｒ^２及びＲ^４は、上記一般式（Ｉ）と同じである。）

(In the formula, X ¹¹ is a group represented by the following general formula (1), and R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ and R ¹¹⁹ are a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group. Group, optionally substituted alkyl group having 1 to 40 carbon atoms, aryl group having 6 to 20 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, or complex having 2 to 20 carbon atoms Represents a ring-containing group, and at least one of R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ and R ¹¹⁹ is not a hydrogen atom, and ring A ² is the same as in the above general formula (I-3), and R ² and R ⁴ is the same as in the above general formula (I).)

（上記一般式（１）中、Ｘ¹は、−ＣＲ^１３０Ｒ^１３１−、−ＮＲ^１３２−、二価の炭素原子数１〜３５の脂肪族炭化水素基、炭素原子数６〜３５の芳香族炭化水素基若しくは炭素原子数２〜３５の複素環基、又は、下記式（イ）、（ロ）若しくは（ハ）で表されるいずれかの置換基を表し、該脂肪族炭化水素基は、−Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−又は−ＮＨ−、あるいは酸素原子が隣り合うことなしにこれらを組み合わせた結合基で中断されていてもよく、Ｒ^１３０及びＲ^１３１は、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、Ｚ^1１及びＺ^１２は、それぞれ独立に、直接結合、−Ｏ−、−Ｓ−、＞ＣＯ、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−、−ＳＯ₂−、−ＳＳ−、−ＳＯ−又は＞ＮＲ^１３３を表し、Ｒ^１３２及びＲ^１３３は、水素原子、置換基を有していてもよい炭素原子数１〜３５の脂肪族炭化水素基、置換基を有していてもよい炭素原子数６〜３５の芳香族炭化水素基又は置換基を有していてもよい炭素原子数２〜３５の複素環基を表す。）

(In the general formula (1), X ¹ represents —CR ¹³⁰ R ¹³¹ —, —NR ¹³² —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an aromatic group having 6 to 35 carbon atoms. A hydrocarbon group or a heterocyclic group having 2 to 35 carbon atoms, or any substituent represented by the following formula (A), (B) or (C), the aliphatic hydrocarbon group is: -O-, -S-, -CO-, -COO-, -OCO- or -NH-, or may be interrupted by a linking group that combines these without adjacent oxygen atoms, and R ¹³⁰ and R ¹³¹ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and Z ¹¹ and Z ¹² are each independently , Direct bond, -O-, -S-,> CO, -CO-O-,- Represents O—CO—, —SO ₂ —, —SS—, —SO— or> NR ¹³³ , and R ¹³² and R ¹³³ each have 1 to 35 carbon atoms which may have a hydrogen atom or a substituent. It represents an aliphatic hydrocarbon group, an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent, or a heterocyclic group having 2 to 35 carbon atoms which may have a substituent. )

（式中、ｍ＝２〜６であり、Ｘ^３は、ｍ＝２のとき上記一般式（１）で表される基であり、ｍ＝３のとき下記一般式（２）で表される基であり、ｍ＝４のとき下記一般式（３）で表される基であり、ｍ＝５のとき下記一般式（４）で表される基であり、ｍ＝６のとき下記一般式（５）で表される基であり、Ｒ^１２５、Ｒ^１２６、Ｒ^１２７及びＲ^１２８は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数１〜４０のアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアリールアルキル基又は炭素原子数２〜２０の複素環含有基を表し、Ｒ^１２５、Ｒ^１２６、Ｒ^１２７及びＲ^１２８のうち少なくとも１つは水素原子でなく、環Ａ^２は、上記一般式（Ｉ−３）と同じであり、Ｒ^２及びＲ^４は、上記一般式（Ｉ）と同じである。）

(In the formula, m = 2 to 6, and X ³ is a group represented by the general formula (1) when m = 2, and represented by the following general formula (2) when m = 3. A group represented by the following general formula (3) when m = 4, a group represented by the following general formula (4) when m = 5, and the following general formula when m = 6 In the group represented by (5), R ¹²⁵ , R ¹²⁶ , R ¹²⁷ and R ¹²⁸ may have a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group or a substituent. Represents an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms, R ¹²⁵ , R ¹²⁶ , at least one of ^{R 127} and ^{R 128} are not hydrogen atom, ring ^{a 2,} the above general formula ( -3) is the same as, ^{R 2} and ^{R 4} are as defined for general formula (I).)

（上記一般式（２）中、Ｙ^１１は、三価の炭素原子数３〜３５の脂肪族炭化水素基、炭素原子数３〜３５の脂環族炭化水素基、炭素原子数６〜３５の芳香族炭化水素基若しくは炭素原子数２〜３５の複素環基を表し、Ｚ^1１、Ｚ^１２及びＺ^１３は、それぞれ独立に、直接結合、−Ｏ−、−Ｓ−、＞ＣＯ、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−、−ＳＯ₂−、−ＳＳ−、−ＳＯ−、＞ＮＲ^１３２、＞ＰＲ^１３２又は置換基を有していてもよい炭素原子数１〜３５の脂肪族炭化水素基、置換基を有していてもよい炭素原子数６〜３５の芳香族炭化水素基又は置換基を有していてもよい炭素原子数２〜３５の複素環基を表し、Ｒ^１３２は、水素原子、置換基を有していてもよい炭素原子数１〜３５の脂肪族炭化水素基、置換基を有していてもよい炭素原子数６〜３５の芳香族炭化水素基又は置換基を有していてもよい炭素原子数２〜３５の複素環基を表し、該脂肪族炭化水素基は、炭素−炭素二重結合、−Ｏ−、−ＣＯ−、−Ｏ−ＣＯ−、−ＣＯ−Ｏ−又は−ＳＯ_２−で中断されていてもよい。）

(In the above general formula (2), Y ¹¹ is a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 to 35 carbon atoms. Represents an aromatic hydrocarbon group or a heterocyclic group having 2 to 35 carbon atoms, and Z ¹¹ , Z ¹² and Z ¹³ are each independently a direct bond, —O—, —S—,> CO, —CO—. O—, —O—CO—, —SO ₂ —, —SS—, —SO—,> NR ¹³² ,> PR ¹³² or an optionally substituted aliphatic hydrocarbon having 1 to 35 carbon atoms A group, an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent or a heterocyclic group having 2 to 35 carbon atoms which may have a substituent, and R ¹³² is A hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, and a carbon atom optionally having a substituent Represents an aromatic hydrocarbon group having 6 to 35 children or a heterocyclic group having 2 to 35 carbon atoms which may have a substituent, and the aliphatic hydrocarbon group includes a carbon-carbon double bond,- O -, - CO -, - O-CO -, - CO-O- or -SO ₂ - it may be interrupted by).

（上記一般式（３）中、Ｙ^１２は、炭素原子、又は、四価の炭素原子数１〜３５の脂肪族炭化水素基、炭素原子数６〜３５の芳香族炭化水素基若しくは炭素原子数２〜３５の複素環基を表し、該脂肪族炭化水素基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−で中断されていてもよく、Ｚ¹¹〜Ｚ¹⁴は、それぞれ独立に、上記一般式（２）におけるＺ¹¹〜Ｚ¹³で表される基と同じ範囲の基である。）

(In the general formula (3), Y ¹² represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or the number of carbon atoms. Represents a heterocyclic group of 2 to 35, and the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—, ^{11 to} Z ¹⁴ are each independently a group in the same range as the group represented by Z ^{11 to} Z ¹³ in the general formula (2).

（上記一般式（４）中、Ｙ^１３は、五価の炭素原子数２〜３５の脂肪族炭化水素基、炭素原子数６〜３０の芳香族炭化水素基又は炭素原子数２〜３０の複素環基を表し、該脂肪族炭化水素基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−で中断されていてもよく、Ｚ¹¹〜Ｚ¹⁵は、それぞれ独立に、上記一般式（２）におけるＺ¹¹〜Ｚ¹³で表される基と同じ範囲の基である。）

(In General Formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a complex having 2 to 30 carbon atoms. Represents a cyclic group, and the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—, wherein Z ^{11 to} Z ¹⁵ are And each independently a group in the same range as the group represented by Z ^{11 to} Z ¹³ in the general formula (2).)

（上記一般式（５）中、Ｙ^１４は、六価の炭素原子数２〜３５の脂肪族炭化水素基、炭素原子数６〜３５の芳香族炭化水素基又は炭素原子数２〜３５の複素環基を表し、該脂肪族炭化水素基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−で中断されていてもよく、Ｚ¹¹〜Ｚ¹⁵は、それぞれ独立に、上記一般式（２）におけるＺ¹¹〜Ｚ¹³で表される基と同じ範囲の基である。）

(In the general formula (5), Y ¹⁴ represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a complex having 2 to 35 carbon atoms. Represents a cyclic group, and the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—, wherein Z ^{11 to} Z ¹⁵ are And each independently a group in the same range as the group represented by Z ^{11 to} Z ¹³ in the general formula (2).)

Among the compounds represented by the above general formula (I), R ⁴ is an alkyl group having 1 to 20 carbon atoms, and a methylene group located at the terminal on the oxygen atom side is replaced by —CO—O—. In particular, those having —CO—O— bonded to the terminal on the oxygen atom side of an alkyl group having 1 to 8 carbon atoms are preferable because they effectively exhibit the function as a latent additive.
R ^{1 1} and / or R ² and R ^{111 to} R ¹¹⁹ and R ^{125 to} R ¹²⁸ in formulas I-3 to I-5 are hydrogen atoms or 1 to 40 carbon atoms, particularly 1 to 10, especially 1 to Those having 5 alkyl groups are also preferred.

  The method for producing the compound represented by the general formula (I) is not particularly limited. For example, JP-A-57-111375, JP-A-3-173843, JP-A-6-128195, JP-A-7-207771, JP-A-7 -252191, JP-A-2004-501128, phenolic compounds produced by the methods described in each publication, acid anhydrides, acid chlorides, Boc reagents, alkyl halide compounds, silyl chloride compounds, allyl ether compounds, etc. It can be obtained by reaction.

In the coloring composition of the present invention, the content of the latent antioxidant (A) is preferably 0.05 to 10% by mass, more preferably 0.1% in the solid content of the coloring composition. ˜5 mass%. If the content of the latent antioxidant (A) is more than 10% by mass, heat curing may be poor, and if it is less than 0.05% by mass, the antioxidant function may not work and the color characteristics may be deteriorated. .
Further, the content of the latent antioxidant (A) in the colorable composition of the present invention is preferably 0.01 to 2% by mass, more preferably 0. It is 02-1 mass%.

<Colorant (B)>
As the colorant (B) used in the colorable composition of the present invention, an inorganic color material or an organic color material can be used, and these can be used alone or in admixture of two or more.
Examples of the inorganic color material or organic color material include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds, and quinacridones. Compound, anthanthrone compound, perinone compound, perylene compound, diketopyrrolopyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compound, quinophthalone compound, naphthalenetetracarboxylic acid; azo dye, metal complex compound of cyanine dye; lake pigment; Carbon black obtained by the method, channel method, thermal method, or carbon black such as acetylene black, ketjen black or lamp black; -Bon black adjusted with epoxy resin, coated, carbon black previously dispersed with resin in solvent, 20-200 mg / g resin adsorbed, carbon black treated with acidic or alkaline surface, Graphite having an average particle size of 8 nm or more and a DBP oil absorption of 90 ml / 100 g or less, and a total oxygen amount calculated from CO and CO ₂ in the volatile content at 950 ° C. of 9 mg or more per 100 m2 of carbon black surface area; Graphite , Graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; synthetic iron black; titanium dioxide, potassium titanate, zircon oxide, Zinc sulfide, oxidation White pigments such as zinc, magnesium oxide, beryllium oxide; hydrophobic resin, chromium oxide green, miloli blue, cobalt green, cobalt blue, manganese-based, ferrocyanide, phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, Inorganic or organic pigments such as emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, and amber can be used.

  As the inorganic color material or organic color material, commercially available pigments can also be used. For example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 3, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; pigment violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, and the like.

  As the inorganic color material or organic color material, known dyes can be used. Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, Examples thereof include phthalocyanine dyes and cyanine dyes.

  When the colorant (B) is a black pigment, as described later, the colorable composition of the present invention can be used as a black matrix for a color filter for a display device for an image display device, etc. It is preferable because it can be used for a black paint. Moreover, when the said coloring agent (B) is a white pigment, it is preferable from the point which can be used for the white coating material for touchscreen cover glass.

  In the coloring composition of the present invention, the content of the colorant (B) is 100 parts by mass of the total amount of the component (A), the component (B), the component (D), and the component (E). On the other hand, it is preferably 0 to 350 parts by mass, more preferably 0 to 250 parts by mass. When it exceeds 350 parts by mass, the colorant tends to aggregate and storage stability is deteriorated.

  A solvent (C) can be further added to the coloring composition of the present invention. The solvent is usually a solvent capable of dissolving or dispersing each of the above components (the latent antioxidant (A) and the colorant (B) of the present invention) as necessary, such as methyl ethyl ketone and methyl amyl ketone. , Ketones such as diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, γ-butyrolactone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, Ether solvents such as dipropylene glycol dimethyl ether; ester solvents such as methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; ethylene glycol monomethyl Ete Cellosolve solvents such as ethylene glycol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate , Ether ester solvents such as propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl ether acetate, ethoxyethyl ether propionate; BTX such as benzene, toluene, xylene Solvents: Aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; Terpene charcoal such as turpentine oil, D-limonene and pinene Hydrocarbon oil; paraffinic solvents such as mineral spirit, Swazol # 310 (Cosmo Matsuyama Oil Co., Ltd.), Solvesso # 100 (Exxon Chemical Co., Ltd.); carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, 1,2- Halogenated aliphatic hydrocarbon solvents such as dichloroethane; Halogenated aromatic hydrocarbon solvents such as chlorobenzene; Carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water and the like can be mentioned, and these solvents can be used as one or a mixture of two or more. Among these, ketones, ether ester solvents and the like, particularly propylene glycol-1-monomethyl ether-2-acetate (PGMEA), cyclohexanone, and the like are preferable because the compatibility of the resist and the photopolymerization initiator in the colored composition is good.

  In the coloring composition of the present invention, the amount of the solvent used is preferably such that the concentration of the composition other than the solvent is 5 to 30% by mass, and if it is less than 5% by mass, it is difficult to increase the film thickness. It is not preferable because it cannot sufficiently absorb light of a desired wavelength, and when it exceeds 30% by mass, the storage stability of the composition due to precipitation of the composition is decreased, and the viscosity is improved, so that handling is decreased. Absent.

Resin (D) can be further added to the coloring composition of the present invention. The resin (D) can be used without any particular limitation, and examples thereof include a homopolymer or a copolymer containing a repeating unit derived from a photopolymerizable unsaturated monomer.
Among them, methacrylic acid ester copolymers, polyvinyl alcohol / polyvinyl ether / polyvinyl ester copolymers, unsaturated polyesters and the like are preferable because they have good compatibility with the photopolymerizable unsaturated monomer (D) described later, Those having a valence are preferable from the viewpoint of photographic properties.

  Examples of the resin (D) having an acid value (or a monomer thereof) include (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, highmic acid, crotonic acid, and isocrotone. Acid, vinyl acetate, allyl acetate, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ω-carboxyl Polymers having a carboxy group and a hydroxyl group at both ends, such as polycaprolactone mono (meth) acrylate, mono (meth) acrylate, hydroxyethyl (meth) acrylate / malate, hydroxypropyl (meth) acrylate / malate, dicyclopentadiene / malate Or one carboxyl group and two or more (meth) acryloyl groups Polyfunctional (meth) acrylates and other unsaturated polybasic acids having the following: unsaturated pentabasic acids such as dipentaerythritol penta (meth) acrylate and pentaerythritol tri (meth) acrylate and esters of polyhydric alcohols or polyphenols Unsaturated aromatic compounds such as 4-hydroxystyrene, vinyl benzoic acid, vinyl phenol, vinyl sulfonic acid, 4-vinyl benzene sulfonic acid and vinyl benzyl glycidyl ether; vinyl alcohols such as allyl alcohol and crotyl alcohol; pentaerythritol tris Reaction products of hydroxyl group-containing polyfunctional acrylates such as acrylate and dipentaerythritol pentaacrylate and dibasic anhydrides such as succinic anhydride, phthalic anhydride and tetrahydrophthalic anhydride; epoxy compounds represented by the following general formula (III) Reacted with unsaturated monobasic acid to the epoxy groups of the like, it may be used resins obtained by the action of further polybasic acid anhydride. These monomers can be used individually by 1 type or in mixture of 2 or more types. Moreover, it is preferable that resin (D) which has said acid value contains 0.2-1.0 equivalent of unsaturated groups.

（式中、Ｘ⁵は直接結合、メチレン基、炭素原子数１〜４のアルキリデン基、炭素原子数３〜２０の脂環式炭化水素基、−Ｏ−、−Ｓ−、−ＳＯ₂−、−ＳＳ−、−ＳＯ−、−ＣＯ−、−ＯＣＯ−又は下記式（イ）、（ロ）若しくは（ハ）で表される置換基を表し、該アルキリデン基はハロゲン原子で置換されていてもよく、Ｒ⁴¹、Ｒ⁴²、Ｒ⁴³及びＲ⁴⁴は、それぞれ独立に、水素原子、炭素原子数１〜５のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数２〜５のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、ｍは０〜１０の整数である。）

(Wherein X ⁵ is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO ₂ —, -SS-, -SO-, -CO-, -OCO- or a substituent represented by the following formula (I), (B) or (C), wherein the alkylidene group may be substituted with a halogen atom R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl having 2 to 5 carbon atoms. Represents a group or a halogen atom, and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and m is an integer of 0 to 10.)

（式中、Ｚ¹は水素原子、炭素原子数１〜１０のアルキル基又はアルコキシ基により置換されていてもよいフェニル基又は炭素原子数３〜１０のシクロアルキル基を表し、Ｙ¹は炭素原子数１〜１０のアルキル基、炭素原子数１〜１０のアルコキシ基、炭素原子数２〜１０のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、ｅは０〜５の整数である。）

(In the formula, Z ¹ represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group, or a cycloalkyl group having 3 to 10 carbon atoms, and Y ¹ is a carbon atom. Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, wherein the alkyl group, alkoxy group and alkenyl group are substituted with a halogen atom; And e is an integer from 0 to 5.)

（式中、Ｙ²及びＺ²は、それぞれ独立して、ハロゲン原子で置換されていてもよい炭素原子数１〜１０のアルキル基、ハロゲン原子で置換されていてもよい炭素原子数６〜２０のアリール基、ハロゲン原子で置換されていてもよい炭素原子数６〜２０のアリールオキシ基、ハロゲン原子で置換されていてもよい炭素原子数６〜２０のアリールチオ基、ハロゲン原子で置換されていてもよい炭素原子数６〜２０のアリールアルケニル基、ハロゲン原子で置換されていてもよい炭素原子数７〜２０のアリールアルキル基、ハロゲン原子で置換されていてもよい炭素原子数２〜２０の複素環基、又はハロゲン原子を表し、上記アルキル基及びアリールアルキル基中のアルキレン部分は、不飽和結合、−Ｏ−又は−Ｓ−で中断されていてもよく、Ｚ²は、隣接するＺ²同士で環を形成していてもよく、ｐは０〜４の整数を表し、ｑは０〜８の整数を表し、ｒは０〜４の整数を表し、ｓは０〜４の整数を表し、ｒとｓの数の合計は２〜４の整数である。）

Wherein Y ² and Z ² are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or 6 to 20 carbon atoms which may be substituted with a halogen atom. An aryloxy group having 6 to 20 carbon atoms which may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms which may be substituted with a halogen atom, or a halogen atom An arylalkenyl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms that may be substituted with a halogen atom, or a complex having 2 to 20 carbon atoms that may be substituted with a halogen atom ring group, or a halogen atom, the alkylene moiety in the alkyl group and arylalkyl group, an unsaturated bond, may be interrupted by -O- or -S-, Z ² , May form a ring with the adjacent Z ² together, p represents an integer of 0 to 4, q represents an integer of 0 to 8, r represents an integer of 0 to 4, s is 0 4 represents an integer, and the total number of r and s is an integer of 2 to 4.)

The unsaturated monobasic acid that acts on the epoxy group of the epoxy compound includes acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, hydroxyethyl acrylate / malate, hydroxypropyl methacrylate / malate. , Hydroxypropyl acrylate malate, dicyclopentadiene malate and the like.
In addition, the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride Maleic anhydride adduct, dodecenyl succinic anhydride, and anhydride and methyl high Mick acid.

The reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in the epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group of the epoxy adduct is 1 It is preferable that the acid anhydride structure of the polybasic acid anhydride has a ratio of 0.1 to 1.0.
Reaction of the said epoxy compound, the said unsaturated monobasic acid, and the said polybasic acid anhydride can be performed in accordance with a conventional method.

  In order to improve the developability of the coloring composition of the present invention by adjusting the acid value of the resin (D) having the acid value, a monofunctional or polyfunctional epoxy compound can be further used. The resin having the acid value preferably has a solid acid value in the range of 5 to 120 mgKOH / g, and the usage amount of the monofunctional or polyfunctional epoxy compound is selected so as to satisfy the acid value. preferable.

  Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl. Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, Allyl glycidylate , Propargyl glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxy glycidyl ether, p-butylphenol glycidyl ether, cresyl glycidyl ether, 2-methyl cresyl glycidyl ether, 4-nonylphenyl glycidyl ether, benzyl glycidyl Ether, p-cumylphenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylate, epoxidized soybean oil, epoxidized linseed oil, glycidyl butyrate, vinylcyclohexane monooxide, 1,2-epoxy-4-vinyl Cyclohexane, styrene oxide, pinene oxide, methylstyrene oxide, cyclohexene oxide, propylene oxide, the following compound No. A2, No. A3 etc. are mentioned.

As the polyfunctional epoxy compound, it is preferable to use one or more selected from the group consisting of bisphenol type epoxy compounds and glycidyl ethers because an alkali-developable photosensitive composition with better characteristics can be obtained. As the bisphenol type epoxy compound, an epoxy compound represented by the above general formula (III) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used. Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (glycidyloxymethyl) methane, 1,1,1,1- tetra (glycidyloxymethyl) include methane.
Other novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxies such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin and triglycidyl isocyanurate; Dioxide compounds such as cyclopentadiene dioxide; naphthalene type epoxy compounds, triphenylmethane type epoxy compounds, dicyclopentadiene type epoxy compounds and the like can also be used.

  Among the resins (D) having an acid value, unsaturated polybasic acids and polyfunctional acrylates having an acid value are preferable from the viewpoint of compatibility, alkali developability and heat resistance, and polyfunctional acrylates having an acid value are particularly preferable. preferable.

  Commercially available resins can be used as the resin (D) having an acid value, for example, SPC-1000, SPC-3000 (manufactured by Showa Denko KK), AX3-BX, AX3-RD1, AX3-RD2 (Nippon Shokubai). And JET2000 (manufactured by Osaka Organic Chemical Co., Ltd.).

  A photopolymerizable unsaturated monomer (E) can be further added to the coloring composition of the present invention. The photopolymerizable unsaturated monomer (E) is not particularly limited, and those conventionally used in photosensitive compositions can be used. For example, ethylene, propylene, butylene, isobutylene, chloride Unsaturated aliphatic hydrocarbons such as vinyl, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene; (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, highmic acid, crotonic acid , Isocrotonic acid, vinyl acetate, allyl acetate, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ω -Carboxy polycaprolactone mono (meth) acrylate and other polymer mono having a carboxy group and a hydroxyl group at both ends ( ) Acrylate; hydroxyethyl (meth) acrylate / malate, hydroxypropyl (meth) acrylate / malate, dicyclopentadiene / malate or polyfunctional (meta) having one carboxyl group and two or more (meth) acryloyl groups ) Unsaturated monobasic acids such as acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, the following compound No. A1-No. A4, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, (t-butyl) (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, (meta ) Ethylhexyl acrylate, (meth) acrylic acid Phenoxyethyl, tetrahydrofuryl (meth) acrylate, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol Di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylolethanetri (Meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol Unsaturated monobasic acids such as tra (meth) acrylate, pentaerythritol tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, tri [(meth) acryloylethyl] isocyanurate, polyester (meth) acrylate oligomers and the like Esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyl Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydro Phthalic anhydride-anhydrous Acid anhydrides of unsaturated polybasic acids such as rain acid adducts, dodecenyl succinic anhydride, methyl hymic anhydride; (meth) acrylamide, methylene bis- (meth) acrylamide, diethylenetriamine tris (meth) acrylamide, xylylene bis (meth) Unsaturated monobasic acids such as acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; unsaturated aldehydes such as acrolein; (meth) acrylonitrile, α-chloroacrylonitrile, cyanide Unsaturated nitriles such as vinylidene and allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinyl Unsaturated aromatic compounds such as ruphenol, vinyl sulfonic acid, 4-vinylbenzene sulfonic acid, vinyl benzyl methyl ether, vinyl benzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinyl amine, allyl amine, N-vinyl pyrrolidone, vinyl Unsaturated amine compounds such as piperidine; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, allyl glycidyl ether; maleimide, N-phenylmaleimide, N -Unsaturated imides such as cyclohexylmaleimide; Indenes such as indene and 1-methylindene; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene Macromolecules having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, polysiloxane, etc .; vinyl chloride, vinylidene chloride, divinyls Cuccinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomers and vinyl isocyanate compounds of polyisocyanate compounds, hydroxyl groups Examples thereof include vinyl monomers containing vinyl monomers and polyepoxy compounds.

  Among the various compounds mentioned as the photopolymerizable unsaturated monomer (E), it is particularly preferable to use unsaturated monobasic acid and polyhydric alcohol or polyhydric phenol ester. From the viewpoint of degree characteristics.

  In the coloring composition of the present invention, when the resin (D) and the photopolymerizable unsaturated monomer (E) are used in combination, the content of the photopolymerizable unsaturated monomer (E) is as described above. Resin (D): The photopolymerizable unsaturated monomer (E) is preferably 35 to 95: 5 to 65 parts by mass, and more preferably 40 to 90:10 to 60 parts by mass.

  Moreover, when using the said resin (D) and / or the said photopolymerizable unsaturated monomer (E), in the coloring composition of this invention, the said resin (D) and the said photopolymerizable unsaturated monomer are used. The total amount of (E) is preferably 20 to 80% by mass, more preferably 30 to 70% by mass, in the solid content of the coloring composition of the present invention. If the total content of both is less than 20% by mass, the cured film may not be sufficiently hardened. If it is more than 80% by mass, the colorant may be small and the color characteristics may be insufficient.

In the coloring composition of the present invention, when a pigment or an inorganic compound described later is used, a dispersant (F) can be added. As the dispersant, any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.
In the coloring composition of this invention, when it contains a dispersing agent (F), it is preferable that content of the solid content is 1-300 mass parts with respect to 100 mass parts of coloring agents (B). More preferably, it is -200 mass parts.

  A photoinitiator (G) can further be added to the coloring composition of the present invention. The photopolymerization initiator (G) is not particularly limited as long as it generates radicals by light irradiation, and conventionally known compounds can be used. For example, acetophenone compounds, benzyl compounds, benzophenone compounds can be used. Preferred examples include compounds, ketone compounds such as thioxanthone compounds, and oxime compounds.

  Examples of acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2. -Methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azidobenzal Acetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -Butanone-1, benzoy , Benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propane- 1-one etc. are mentioned.

  Examples of benzyl compounds include benzyl and anisyl.

  Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like. .

  As the oxime compound, a compound represented by the following general formula (II) is particularly preferable from the viewpoint of sensitivity and heat resistance.

（式中、Ｒ^２１及びＲ^２２は、それぞれ独立に、水素原子、シアノ基、炭素原子数１〜２０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は炭素原子数２〜２０の複素環基を表し、
Ｒ^２３びＲ^２４は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、Ｒ^２５、ＯＲ^２６、ＳＲ^２７、ＮＲ^２８Ｒ^２９、ＣＯＲ^３０、ＳＯＲ^３１、ＳＯ_２Ｒ^３２又はＣＯＮＲ^３３Ｒ^３４を表し、Ｒ^２３又はＲ^２４は、隣接するベンゼン環に結合してＸ^２を含む環を形成してもよく、
Ｒ^２５、Ｒ^２６、Ｒ^２７、Ｒ^２８、Ｒ^２９、Ｒ^３０、Ｒ^３１、Ｒ^３２、Ｒ^３３及びＲ^３４は、それぞれ独立に、水素原子、炭素原子数１〜２０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は炭素原子数２〜２０の複素環基を表し、
Ｘ^２は、酸素原子、硫黄原子、セレン原子、ＣＲ^３５Ｒ^３６、ＣＯ、ＮＲ^３７又はＰＲ^３８を表し、
Ｘ^３は、単結合又はＣＯを表し、
Ｒ³⁵、Ｒ³⁶、Ｒ³⁷及びＲ³⁸は、それぞれ独立に、水素原子、炭素原子数１〜２０のアルキル基、炭素原子数６〜３０のアリール基又は炭素原子数７〜３０のアリールアルキル基を表し、
上記のアルキル基、アリール基及びアリールアルキル基中の水素原子は、更に、水酸基、炭素原子数１〜２０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は炭素原子数２〜２０の複素環基で置換されていても良く、上記アルキル基及びアリールアルキル基中のメチレン基は、−Ｏ−で中断されていてもよく、
Ｒ^３５、Ｒ^３６、Ｒ^３７及びＲ^３８は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよく、
ａは、０〜４の整数を表し、
ｂは、１〜５の整数を表す。）

(In the formula, R ²¹ and R ²² are each independently a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl having 7 to 30 carbon atoms. Represents a group or a heterocyclic group having 2 to 20 carbon atoms,
R ^{23 and} R ²⁴ are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R ²⁵ , OR ²⁶ , SR ²⁷ , NR ²⁸ R ²⁹ , COR ³⁰ , SOR ³¹ , SO _2. R ³² or CONR ³³ R ³⁴ , R ²³ or R ²⁴ may be bonded to an adjacent benzene ring to form a ring containing X ² ;
R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a carbon atom. An aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms;
X ² represents an oxygen atom, a sulfur atom, a selenium atom, CR ³⁵ R ³⁶ , CO, NR ³⁷ or PR ³⁸ ,
X ³ represents a single bond or CO,
R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an arylalkyl group having 7 to 30 carbon atoms. Represents
The hydrogen atom in the above alkyl group, aryl group and arylalkyl group further includes a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arylalkyl having 7 to 30 carbon atoms. A methylene group in the alkyl group or arylalkyl group may be interrupted by -O-, and may be substituted with a group or a heterocyclic group having 2 to 20 carbon atoms,
R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ may each independently form a ring together with one of the adjacent benzene rings,
a represents an integer of 0 to 4,
b represents an integer of 1 to 5. )

  Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

  Other radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1-yl)] titanium. Etc.

  These radical photopolymerization initiators can be used alone or in combination of two or more according to the desired performance.

  When the photopolymerization initiator (G) is used, the content of the photopolymerization initiator in the colorable composition of the present invention is 0.1 to 30% by mass, particularly in the solid content of the colorable composition of the present invention. 0.5-10 mass% is preferable. When the content of the photopolymerization initiator is less than 0.1% by mass, curing by exposure may be insufficient, and when it is more than 30% by mass, the initiator may be precipitated in the composition.

  The coloring composition of the present invention can further contain an inorganic compound. Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable. In the coloring composition of the present invention, when an inorganic compound is used, the content thereof is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 100 parts by mass of the photopolymerizable unsaturated compound. It is -20 mass parts, and these inorganic compounds can use 1 type (s) or 2 or more types.

When the coloring composition of the present invention contains an inorganic compound, it can be used as a photosensitive paste composition. The photosensitive paste composition is used for forming a fired product pattern such as a filter segment of a color filter, a partition pattern of a plasma display panel, a dielectric pattern, an electrode pattern, and a black matrix pattern.
These inorganic compounds are also suitably used as, for example, fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellent agents, and the like.

  In addition, the coloring composition of the present invention includes, if necessary, a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; a plasticizer; an adhesion promoter; a filler; Foaming agent; Leveling agent; Surface conditioner; Antioxidant; Ultraviolet absorber; Dispersion aid; Aggregation inhibitor; Catalyst; Effect accelerator; Cross-linking agent; Thickener; be able to.

  In the colorable composition of the present invention, the latent antioxidant (A), the colorant (B), the solvent (C), the resin (D), the photopolymerizable unsaturated monomer (E), the dispersant (F ), And the content of optional components other than the photopolymerization initiator (G) is appropriately selected according to the purpose of use and is not particularly limited. Preferably, the content of the component (D) and the component (E) is 100. The total amount is 50 parts by mass or less with respect to parts by mass.

  Further, a chain transfer agent, a sensitizer, a surfactant, melamine and the like can be used in combination with the coloring composition of the present invention.

  As the chain transfer agent and sensitizer, a sulfur atom-containing compound is generally used. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3- [N- ( 2-mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol , 2-me Captoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3- Mercapto compounds such as mercaptopropionate), disulfide compounds obtained by oxidizing the mercapto compounds, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid, etc. Alkyl compound, trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, Karenz PE1, NR1 manufactured by Showa Denko KK and the like.

  Examples of the surfactant include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.

Examples of the melamine compound include all or part of active methylol groups (CH ₂ OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other. Moreover, the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used. Among these, alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.

  The coloring composition of the present invention is dispersed and used by kneading using a bead mill, or by known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, etc. It can be applied to a supporting substrate such as soda glass, quartz glass, a semiconductor substrate, metal, paper, and plastic. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base | substrate, There is no restriction | limiting in the application method.

  In addition, as the light source of the active light used when the coloring composition of the present invention is cured, one that emits light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, carbon An arc, a xenon arc, or the like can be used.

  Furthermore, by using laser light as the exposure light source, the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy. As the laser light, light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.

  The coloring composition of the present invention includes paints, coating agents, lining agents, inks, resists, liquid resists, adhesives, printing plates, insulating varnishes, insulating sheets, laminates, printed boards, semiconductor devices and LED packages. Sealants, molding materials, putty, glass fiber impregnants, and sealants for liquid crystal inlets, liquid crystal displays, organic EL, touch panels, optical elements, electrical insulation, electronic components, and separation membranes It can be used for passivation films for semiconductors and solar cells, interlayer insulating films, protective films and the like.

In addition to the latent antioxidant (A) and the colorant (B), the colorable composition of the present invention comprises a solvent (C), a resin (D), a photopolymerizable unsaturated monomer (if necessary) Any component of E) and dispersant (F) can be mixed to obtain a pigment paste.

  The colorable composition of the present invention can be used to form a frame of various colors on a tempered glass substrate by a photolithography process when various pigments are used as a colorant, and can suppress discoloration at a high temperature. Since it is excellent, through a process such as ITO sputtering, it is possible to form a light touch panel with high design as a sensor-integrated cover glass in a projected capacitive touch panel.

  The sensor-integrated cover glass comprises (1) a step of forming a coating film of the coloring composition of the present invention on a tempered glass substrate, and (2) active light through a mask having a predetermined pattern shape on the coating film. (3) a step of developing the exposed film with a developer (particularly an alkali developer), (4) a step of heating the film after development, (5) an ITO sputtering step, (6) It is preferably formed by an overcoat process. The coloring composition of the present invention is also useful as a screen printing system composition without a development step.

  The colorable composition of the present invention is used for the purpose of forming a black matrix when a black pigment is used as a colorant, and the black matrix is a color filter for a display device especially for an image display device such as a liquid crystal display panel. Useful for.

The black matrix includes (1) a step of forming a coating film of the coloring composition of the present invention on a substrate, (2) a step of irradiating the coating film with active light through a mask having a predetermined pattern shape, (3) It is preferably formed by a step of developing the exposed film with a developer (particularly an alkali developer), and (4) a step of heating the film after development. The colored composition of the present invention is also useful as an ink jet composition without a development process.
Manufacture of color filters for use in liquid crystal display panels, etc. is made by repeating the above steps (1) to (4) using the present invention or other colored compositions and combining patterns of two or more colors. Can do.

  EXAMPLES Hereinafter, although an Example etc. are given and this invention is demonstrated further in detail, this invention is not limited to these Examples.

[Production Example 1] Resin No. Preparation of 1 30.0 g of 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane, 7.52 g of acrylic acid, 0.080 g of 2,6-di-t-butyl-p-cresol Then, 0.183 g of tetrabutylammonium chloride and 11.0 g of PGMEA were charged and stirred at 90 ° C. for 1 hour, 105 ° C. for 1 hour and 120 ° C. for 17 hours. After cooling to room temperature, 8.11 g of succinic anhydride, 0.427 g of tetrabutylammonium chloride and 11.1 g of PGMEA were added, and the mixture was stirred at 100 ° C. for 5 hours. Further, 12.0 g of 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane, 0.080 g of 2,6-di-t-butyl-p-cresol and 0.600 g of PGMEA were added. After stirring at 90 ° C. for 90 minutes and at 120 ° C. for 5 hours, 24.0 g of PGMEA was added to obtain a PGMEA solution as resin no. 1 was obtained (Mw = 4900, Mn = 2250, acid value (solid content) 47 mg · KOH / g).

[Production Example 2] Resin No. Preparation of 2 184 g of 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane, 58 g of acrylic acid, 0.26 g of 2,6-di-tert-butyl-p-cresol, tetra-n -0.11 g of butylammonium bromide and 23 g of PGMEA were charged and stirred at 120 ° C for 16 hours. The reaction solution was cooled to room temperature, 35 g of PGMEA, 59 g of biphthalic anhydride and 0.24 g of tetra-n-butylammonium bromide were added, and the mixture was stirred at 120 ° C. for 4 hours. Furthermore, after adding 20 g of tetrahydrophthalic anhydride, stirring at 120 ° C. for 4 hours, 100 ° C. for 3 hours, 80 ° C. for 4 hours, 60 ° C. for 6 hours, and 40 ° C. for 11 hours, PGMEA 90 g was added to add PGMEA solution Resin No. 2 (Mw = 5000, Mn = 2100, acid value (solid content) 92.7 mgKOH / g).

[Production Example 3] Resin No. Preparation of 3 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane 43 g, acrylic acid 11 g, 2,6-di-tert-butyl-p-cresol 0.05 g, tetrabutylammonium acetate 0.11 g and PGMEA 23 g were charged and stirred at 120 ° C. for 16 hours. After cooling to room temperature, 35 g of PGMEA and 9.4 g of biphenyltetracarboxylic dianhydride were added and stirred at 120 ° C. for 8 hours. Further, 6.0 g of tetrahydrophthalic anhydride was added and stirred at 120 ° C. for 4 hours, at 100 ° C. for 3 hours, at 80 ° C. for 4 hours, at 60 ° C. for 6 hours, and at 40 ° C. for 11 hours, and then added with PGMEA 29 g to obtain a PGMEA solution Resin No. 3 (Mw = 4000, Mn = 2100, acid value (solid content) 86 mgKOH / g).

[Production Example 4] Resin No. Production of 4 9,9-bis (4-glycidyloxyphenyl) fluorene 75.0 g, acrylic acid 23.8 g, 2,6-di-t-butyl-p-cresol 0.273 g, tetrabutylammonium chloride 0.585 g And PGMEA 65.9 g, and stirred at 90 ° C. for 1 hour, 100 ° C. for 1 hour, 110 ° C. for 1 hour and 120 ° C. for 14 hours. After cooling to room temperature, 25.9 g of succinic anhydride, 0.427 g of tetrabutylammonium chloride, and 1.37 g of PGMEA were added, and the mixture was stirred at 100 ° C. for 5 hours. Further, 90.0 g of 9,9-bis (4-glycidyloxyphenyl) fluorene, 0.269 g of 2,6-di-t-butyl-p-cresol and 1.50 g of PGMEA were added, and 90 minutes at 90 ° C. After stirring at 120 ° C. for 4 hours, 93.4 g of PGMEA was added to obtain the resin No. 1 as the target product as a PGMEA solution. 4 (Mw = 4190, Mn = 2170, acid value (solid content) 52 mg · KOH / g).

[Production Example 5] Synthesis of 1 A phenol compound (0.01 mol), di-tert-butyl dicarbonate (0.05 mol) and pyridine (30 g) were mixed. Under a nitrogen atmosphere, 0.025 mol of 4-dimethylaminopyridine was added at room temperature, and the mixture was stirred at 60 ° C for 3 hours. . After cooling to room temperature, the reaction solution was poured into 150 g of ion-exchanged water, and 200 g of chloroform was added to perform oil / water separation. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and 100 g of methanol was added to the residue for crystallization. The obtained white powdery crystals were dried under reduced pressure at 60 ° C. for 3 hours to obtain the target compound No. 1. 1 was obtained. It was confirmed by ¹ H-NMR and IR that the obtained white powdery crystals were the target product. The results are shown in Table A and Table B.

[Production Examples 6 to 7] The following compound No. Synthesis of 2 to 4 In the same manner as in Production Example 5, the following compound Nos. 2-No. 4 was synthesized. It was confirmed by ¹ H-NMR and IR that the obtained compound was the target product. The results are shown in Table A and Table B.

[Example 1-1] Preparation of coloring composition A (A) The following compound No. which is a component 0.1 g of 1 and 8 g of MA-100 (carbon black; manufactured by Mitsubishi Chemical Corporation) as component (B) are added to 80 g of γ-butyrolactone as component (C), and 30 g at 7000 rpm using a homogenizer with 200 g of glass beads. After dispersing for minutes, the glass beads were filtered and removed to obtain a coloring composition A.

[Example 1-2] Preparation of coloring composition B (A) The following compound No. which is a component 0.1 g of 1, MA-100 (carbon black; manufactured by Mitsubishi Chemical Corporation) as component (B), 80 g of PGMEA as component (C), cyclomer ACA250 (acrylic polymer; Daicel Chemical Company) as component (D) (Product made) 6.5g, (F) component BYK-182 (Bic Chemie company made) 1.5g was stirred and mixed, zirconia beads 40g was added and dispersed for 6 hours in a bead mill to obtain a coloring composition B. .

[Examples 2-1 to 2-14 and Comparative Examples 2-1 to 2-12] Coloring composition No. 1-No. 14 and comparative coloring composition No. 1-No. Preparation of No. 12 According to the composition of [Table 1] to [Table 4], the coloring composition No. 1-No. 14 and comparative coloring composition No. 1-No. 12 was obtained. In addition, the number of the line of A-1 to G-1 represents a mass part.

A-1: The following compound No. 1
A-2: The following compound No. 2
A-3: The following compound No. 3
A-4: The following compound No. 4
A′-1: The following compound No. 5
B-1: MA100 (Mitsubishi Chemical Corporation)
B-2: 13M-C (titanium black; manufactured by Mitsubishi Materials Corporation)
B-3: Titanium oxide C-1: PGMEA
D-1: Resin No. 1 (solid content 45.0% by mass)
D-2: Resin No. 2 (solid content 45.0% by mass)
D-3: Resin No. 3 (solid content 45.0% by mass)
D-4: JET2000 (Osaka Organic Chemical Co., Ltd., solid content: 40.0% by mass)
D-5: Resin No. 4 (solid content 55.0% by mass)
D-6: SPC-1000 (Showa Denko KK, solid content: 30.0% by mass)
D-7: SPC-3000 (manufactured by Showa Denko KK, solid content: 42.0% by mass)
G-1: NCI-831 (manufactured by ADEKA)
G-2: OXE-02 (manufactured by BASF)
E-1: Kayalad DPHA (polyfunctional acrylate; manufactured by Nippon Kayaku Co., Ltd.)
E-2: Aronix M-402 (polyfunctional acrylate; manufactured by Toagosei Co., Ltd.)

[Evaluation Examples 1 to 14 and Comparative Evaluation Examples 1 to 12]
The colored composition No. obtained in Examples 2-1 to 2-14 on glass (AN-100 manufactured by AGC, 100 × 100 × 0.7 mm) was used. 1-No. 14 and Comparative Coloring Composition Nos. Obtained in Comparative Examples 2-1 to 2-12. 1-No. 12 was spin-coated (500 rpm, 7 seconds) and dried. After pre-baking at 90 ° C. for 2 minutes, the entire surface of the substrate was exposed through a mask having a predetermined pattern shape using an ultrahigh pressure mercury lamp as a light source. During exposure, from 0 mJ / cm ² to 400 mJ / cm ^2, and changing the exposure amount in 40 mJ / cm ² intervals. After exposure, the pattern was fixed by baking at 230 ° C. for 30 minutes.
For the obtained pattern, the following chromaticity, OD value, and sensitivity were measured. The results are shown in [Table 1] to [Table 4].
(Chromaticity)
About the obtained board | substrate, (DELTA) _Eab before and behind baking for 30 minutes at 230 _degreeC was investigated using the chromaticity meter (Konica Minolta CM-5). This ΔE _ab measurement was performed on a substrate with exposure amounts set to values shown in [Table 1] to [Table 4].
(OD value)
The OD value of the obtained film was measured using a Macbeth transmission densitometer D-200II, and the OD value per unit film thickness was calculated by dividing the OD value by the film thickness after post-baking. The measurement of the OD value per film thickness was performed on the film having the exposure amount as shown in [Table 1] to [Table 4].
(sensitivity)
Sensitivity was defined as the minimum exposure amount required for the line width after patterning to reach 30 μm or more with respect to the photomask line width of 30 μm. Specifically, the exposure amount of the film having the lowest exposure amount among the films having the line width after patterning of 30 μm or more was set as the minimum exposure amount.

  From the above results, the coloring composition of the present invention containing a latent antioxidant is excellent in sensitivity and heat resistance. Therefore, the coloring composition of the present invention is useful for a cover glass integrated touch panel and a color filter.

Claims (13)

  A coloring composition containing a latent antioxidant (A) and a coloring agent (B).   Furthermore, the coloring composition of Claim 1 containing a solvent (C).   Furthermore, the coloring composition of Claim 1 or 2 containing resin (D) and / or a photopolymerizable unsaturated monomer (E).   Furthermore, the coloring composition as described in any one of Claims 1-3 containing a dispersing agent (F). The coloring composition according to any one of claims 1 to 4, wherein the latent antioxidant (A) is a compound represented by the following general formula (I).

(In the formula, A represents a 5-membered or 6-membered alicyclic, aromatic or heterocyclic ring;
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms An aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms;
R ⁴ is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to 2 carbon atoms. Represents 20 heterocycle-containing groups or trialkylsilyl groups,
The methylene group in the alkyl group or arylalkyl group represented by R ¹ , R ² and R ⁴ is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, — CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-,- CO-NH -, - NH- CO -, - NH-CO-O -, - NR '-,> P = O, -S-S- or -SO ₂ - 1 kinds of groups selected from or two R ′ may represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
A plurality of R ² may be bonded to each other to form a benzene ring or a naphthalene ring,
The plurality of R ² and R ⁴ may be the same or different,
n represents an integer of 1 to 10,
d represents an integer of 1 to 3,
k represents an integer of 1 to 3,
X ¹ is a direct bond, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following formula (I-2),>P═O,> C═O, —NH—CO—, —CO ^{-NH -,> NR 10,>} PR 10, -OR 10, -SR 10, which may have a -NR ¹⁰ R ¹¹ or -PR ¹⁰ R ^11, or n as many substituents having valence carbon C1-C120 aliphatic hydrocarbon group, C6-C35 aromatic ring-containing hydrocarbon group which may have a substituent or C2-C35 which may have a substituent Wherein R ¹⁰ and R ¹¹ are a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an optionally substituted carbon. Represents an aromatic ring-containing hydrocarbon group having 6 to 35 atoms or a heterocycle-containing group having 2 to 35 carbon atoms which may have a substituent. The methylene group in the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocyclic ring-containing group is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO. -O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO One of a group selected from —NH—, —NH—CO—, —NH—CO—O—, —NR ^′ —,> P═O, —S—S—, —SO ₂ — or a nitrogen atom; Two or more combinations may be substituted, and the aromatic ring or the heterocyclic ring may be condensed with another ring. However, if the group X ¹ is represented by a nitrogen atom, phosphorus atom or the following formula (I-2), n is 3, when X ¹ is an oxygen atom or a sulfur atom, n is 2, X ^{When 1} is a direct bond,>P═O,> C═O, —NH—CO—, —CO—NH—,> NR ¹⁰ or> PR ¹⁰ , n is 2, X is —OR ¹⁰ , — In the case of SR ¹⁰ , —NR ¹⁰ R ¹¹ or —PR ¹⁰ R ¹¹ , n is 1 and X ¹ may be combined with A to form a ring. )

  The said coloring agent (B) is a black pigment or a white pigment, The coloring composition as described in any one of Claims 1-5 characterized by the above-mentioned.   The coloring composition according to claim 3, wherein the resin (D) is a homopolymer or a copolymer containing a repeating unit derived from a photopolymerizable unsaturated monomer.   The coloring composition according to claim 3, wherein the photopolymerizable unsaturated monomer (E) is an unsaturated monobasic acid and an ester of a polyhydric alcohol or a polyhydric phenol. The coloring composition as described in any one of Claims 1-8 contains a photoinitiator (G) further, The coloring composition characterized by the above-mentioned. The coloring composition according to claim 9, wherein the photopolymerization initiator (G) is represented by the following general formula (II).

(In the formula, R ²¹ and R ²² are each independently a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl having 7 to 30 carbon atoms. Represents a group or a heterocyclic group having 2 to 20 carbon atoms,
R ^{23 and} R ²⁴ are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R ²⁵ , OR ²⁶ , SR ²⁷ , NR ²⁸ R ²⁹ , COR ³⁰ , SOR ³¹ , SO _2. R ³² or CONR ³³ R ³⁴ , R ²³ or R ²⁴ may be bonded to an adjacent benzene ring to form a ring containing X ² ;
R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a carbon atom. An aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms;
X ² represents an oxygen atom, a sulfur atom, a selenium atom, CR ³⁵ R ³⁶ , CO, NR ³⁷ or PR ³⁸ ,
X ³ represents a single bond or CO,
R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an arylalkyl group having 7 to 30 carbon atoms. Represents
The hydrogen atom in the above alkyl group, aryl group and arylalkyl group further includes a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arylalkyl having 7 to 30 carbon atoms. A methylene group in the alkyl group or arylalkyl group may be interrupted by -O-, and may be substituted with a group or a heterocyclic group having 2 to 20 carbon atoms,
R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ may each independently form a ring together with one of the adjacent benzene rings,
a represents an integer of 0 to 4,
b represents an integer of 1 to 5. )   The pigment paste formed by containing the coloring composition as described in any one of Claims 1-8.   It is a touch panel which has a resin cured material on a cover glass board | substrate, Comprising: This resin cured material is formed with the coloring composition of Claim 9 or 10, The cover glass integrated touch panel characterized by the above-mentioned. A color filter having a resin cured product on a substrate, wherein the resin cured product is formed of the coloring composition according to claim 9 or 10.