KR102316645B1 - Photosensitive compositions and novel compounds - Google Patents

Abstract

(식 중, R¹ 및 R²는, 각각 독립적으로 수소 원자, 할로겐 원자, 시아노기, 수산기, 니트로기, 카복실기, 치환기를 가지고 있는 경우도 있는 탄소 원자 수 1~40의 알킬기, 탄소 원자 수 6~20의 아릴기, 탄소 원자 수 7~20의 아릴알킬기, 탄소 원자 수 2~20의 복소환함유기, 또는 트리알킬실릴기를 나타내고, j는 1~3의 수를 나타내며, *는 *부분에서 인접하는 기와 결합하는 것을 의미한다.)The photosensitive composition containing the compound which has a substituent represented by following General formula (1).

(Wherein, 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, and the number of carbon atoms An aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a heterocycle-containing group having 2 to 20 carbon atoms, or a trialkylsilyl group, j represents a number from 1 to 3, * is a * part means to combine with an adjacent group in

Description

Photosensitive compositions and novel compounds

The present invention relates to a photosensitive composition containing a compound having a specific structure, which is inactive at room temperature, and which is activated by heating to a predetermined temperature to express a function, and a novel compound. Moreover, this invention relates to the coloring photosensitive composition which added the coloring agent to the said photosensitive composition, and the color filter using the said coloring photosensitive composition.

In order to improve the weather resistance and heat resistance of a photosensitive composition, the method of adding and stabilizing a ultraviolet absorber and antioxidant is known (patent documents 1-4).

Since phenolic antioxidants and ultraviolet absorbers have a function of trapping radicals that greatly affect polymer degradation, when they are added to a polymerization system, they generally act as so-called polymerization inhibitors and cause curing inhibition. Since it becomes a problem, a latent additive has been developed (patent document 5).

However, the composition using the conventional latent additive has a problem that there are many outgases, and therefore a heating apparatus is contaminated or the physical property of a composition falls. There is a problem of contamination of the device or reduction of physical properties. Moreover, the composition using the conventional latent additive has a low solvent resistance of the hardened|cured material, and therefore the hardened|cured material elution occurs, for example, there also exists a problem that the brightness|luminance of a color filter is reduced.

Moreover, although the triallyl phenol compound useful as a hardening|curing agent is disclosed by patent document 6, the photosensitive composition containing the said triallyl phenol compound is not suggested.

Japanese Patent Laid-Open No. 2011-048382 Specification of US Patent Application Publication No. 2016/016919 Japanese Laid-Open Patent Publication No. 2015-108649 Japanese Laid-Open Patent Publication No. 2015-132791 International Publication No. 2014/021023 Japanese Patent Application Laid-Open No. 3-232832

Accordingly, it is an object of the present invention to provide a photosensitive composition with little outgas and high solvent resistance of the cured product, using a compound that is inert at room temperature and activated by heating to a predetermined temperature to exhibit a function as an antioxidant or ultraviolet absorber. Moreover, the other objective of this invention is providing the coloring photosensitive composition which added the coloring agent to the said photosensitive composition, especially the coloring photosensitive composition suitable for a color filter.

As a result of intensive studies, the present inventors found that the photosensitive composition using a compound having a specific protecting group has little outgas and has high solvent resistance of the cured product, and the colored photosensitive composition obtained by adding a colorant to the photosensitive composition is optical Without reducing the luminance of the filter (especially a color filter), it was found that it is suitable for a color filter for an image display device such as a liquid crystal display panel, and thus the present invention has been reached.

The present invention has been made based on the above findings, and an object of the present invention is to provide a photosensitive composition containing a compound having a substituent represented by the following general formula (1).

(Wherein, 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, and a substituent An aryl group having 6 to 20 carbon atoms in some cases, an arylalkyl group having 7 to 20 carbon atoms in some cases having a substituent, a heterocyclic group having 2 to 20 carbon atoms in some cases having a substituent, or represents a trialkylsilyl group,

The ^{methylene group in the alkyl group or arylalkyl group represented by R 1} and R ² is -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S- CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR'-, A group selected from -SS- or -SO ₂ - may be substituted with a group in which oxygen atoms are not adjacent to each other, R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,

j represents a number from 1 to 3,

* means to combine with an adjacent group in the * part.)

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail based on preferable embodiment.

The photosensitive composition of this invention contains the compound which has a substituent represented by the said general formula (I).

Among the compounds having a substituent represented by the general formula (I), those represented by the following general formula (I-A) are particularly preferred because of high heat resistance and little outgassing.

(wherein n represents an integer from 1 to 10,

X ¹ represents an n-valent bonding group,

R ¹ , R ² and j are the same as in the general formula (I).)

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 20 carbon atoms represented by R 1} and R ² 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, etc. are mentioned,

Examples ^{of the aryl group having 6 to 20 carbon atoms represented by R 1} and R ² include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinyl Phenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl , 4-(2-ethylhexyl)phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethyl Phenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert- Pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1'-biphenyl)-4 -yl, 2,4,5-trimethylphenyl, ferrocenyl, etc. are mentioned,

Examples ^{of the arylalkyl group having 7 to 20 carbon atoms represented by R 1} and R ² include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenylmethyl, 9-fluorenyl, 3-phenyl propyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl, and the like;

Examples of the heterocyclic ring-containing group having 2 to 20 carbon atoms represented by R ¹ and R ² include a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, a triazine ring, and a pyridine ring. Roline ring, quinoline ring, isoquinoline ring, imidazoline ring, benzoimidazoline ring, triazoline ring, furan ring, benzofuran ring, thiadiazoline ring, thiazoline ring, benzothiazoline ring, thiophene ring, and a group combining a methylene chain with a heterocyclic ring, such as an oxazoline ring, a benzoxazoline ring, an isothiazoline ring, an isoxazoline ring, an indole ring, a pyrrolidine ring, a piperidone ring, and a dioxane ring;

Examples of the trialkylsilyl group represented by R ¹ and R ² include a silyl group substituted with an alkyl group having 1 to 6 carbon atoms (the three alkyl groups are the same or different), such as trimethylsilane, triethylsilane, and ethyldimethylsilane.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R' include those satisfying a predetermined number of carbon atoms among the alkyl groups represented ^{by R 1 .}

A substituent for substituting 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 heterocyclic group having 2 to 20 carbon atoms represented by R ¹ and R ^{2 .} Examples include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; Acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, jade acyl groups such as saloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl and carbamoyl; acyloxy groups such as acetyloxy 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- Octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N,N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonyl substituted amino groups such as amino; 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 group and salts of acid groups and phosphoric acid groups.

As R<^1> and R<^2> , since there is little outgas, a hydrogen atom, a C1-C8 alkyl group, and a C6-C12 aryl group are preferable. Since R<^1> and R<^2> are a hydrogen atom or a branched C1-C8 alkyl group, especially a t-butyl group, since there is little outgas, it is more preferable.

In the above general formula (IA), X ¹ represents an n-valent bonding group, specifically, for example, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and the following (Ia) or (Ib) a group represented by, -CO-, -NH-CO-, -CO-NH-, -NR ³ -, -OR ³ , -SR ³ , -NR ³ R ⁴ , or the same number of valences as n Branch is an aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent, or a carbon atom which may have a substituent. represents a heterocyclic ring-containing group having a number of 2 to 35, R ³ and R ⁴ are a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aliphatic hydrocarbon group having 6 to carbon atoms which may have a substituent An aromatic ring-containing hydrocarbon group of 35 or a heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a substituent, and an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group and a heterocycle-containing group are a carbon-carbon double bond, -O -, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR'-, -SS-, -SO ₂ - or It may be substituted with a group selected from a nitrogen atom.

However, when X ¹ is a nitrogen atom, a phosphorus atom, or a bonding group represented by the following (Ia) or (Ib), n is 3, and X ¹ is an oxygen atom or a sulfur atom, -CO-, -NH-CO-, - When CO-NH- or -NR ³ -, n is 2, and when X ¹ is a hydrogen atom, -OR ³ , -SR ³ or -NR ³ R ⁴ , n is 1 and X ¹ is one with a benzene ring. In some cases, it becomes a ring and forms a ring.

(* means combining with an adjacent group in the * part.)

The compound represented by the general formula (IA) has a structure in which n specific groups are bonded to the n-valent bonding group represented ^{by X 1 .} These n groups are the same or different from each other. The value of n is 1-10, Preferably it is 2-6 from a viewpoint of a low outgas.

^{As an aliphatic hydrocarbon group having 1 to 120 carbon atoms, which is represented by X 1} in the general formula (IA), has the same number of valences as n, and may have a substituent, n is monovalent, for example, methyl , ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bi Cyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, decyl, etc. an alkyl group; Methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tertiary amyloxy, hexyloxy, cyclohexyloxy alkoxy groups such as , heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, and decyloxy; Methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, tertiary amylthio, hexylthio, cyclohexylthio, heptyl alkylthio groups such as thio, isoheptylthio, tertiary heptylthio, n-octylthio, isooctylthio, tertiary octylthio, and 2-ethylhexylthio; vinyl, 1-methylethenyl, 2-methylethenyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, alkenyl groups such as 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, and tricosenyl; and groups in which these groups are substituted by a substituent to be described later, and the like;

As what n is divalent, alkylene, such as methylene, ethylene, propylene, a butylene, and a butyldiyl; wherein the methylene chain of the alkylene is substituted with -O-, -S-, -CO-O-, -O-CO-; residues of diols such as ethanediol, propanediol, butanediol, pentanediol, and hexanediol; residues of dithiols such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol and hexanedithiol; and groups in which these groups are substituted by a substituent to be described later, and the like;

As what n is trivalent, For example, alkylidines, such as propylidine and 1,1, 3- butylidine; and groups in which these groups are substituted by a substituent described later.

Examples of the aromatic ring-containing hydrocarbon group having the same number of valences as n and optionally having a substituent having 6 to 35 carbon atoms, n is monovalent, benzyl, phenethyl, diphenylmethyl, triphenylmethyl, sty arylalkyl groups such as reel and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio; and groups in which these groups are substituted by a substituent to be described later, and the like;

As what n is divalent|divalent, Arylene groups, such as phenylene and naphthylene; residues of bifunctional phenols such as catechol and bisphenol; 2,4,8,10-tetraoxaspiro[5,5]undecane and the like; and groups in which these groups are substituted by a substituent to be described later,

Examples of n being trivalent include phenyl-1,3,5-trimethylene and a group in which these groups are substituted by a substituent described later.

As a heterocyclic ring-containing group having 2 to 35 carbon atoms, which has the same number of valences as n and may have a substituent, n is monovalent, pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl , pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadia Jolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinone-1-yl, 2-piperidon-1-yl, 2,4- deoxyimidazolidin-3-yl, 2,4-deoxyoxazolidin-3-yl, benzotriazoyl and the like; and groups in which these groups are substituted by a substituent to be described later, and the like;

a group in which n is divalent and has a pyridine ring, a pyrimidine ring, a piperidine ring, a piperazine ring, a triazine ring, a furan ring, a thiophene ring, an indole ring or the like; and groups in which these groups are substituted by a substituent to be described later,

Examples of n being trivalent include a group having an isocyanul ring, a group having a triazine ring; and groups in which these groups are substituted by a substituent described later.

As the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by ^{R 3} and R ⁴ , a predetermined number of carbon atoms among the aliphatic hydrocarbon group represented by ^{X 1 and the combination of the aliphatic hydrocarbon group and the substituent} can be said to satisfy

As the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent and the heterocyclic ring containing group having 2 to 35 carbon atoms which may have a substituent represented by ^{R 3} and R ^{4 , X 1 among} the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, the heterocyclic ring-containing group having 2 to 35 carbon atoms, and groups in which these groups and a substituent described later are combined, those satisfying a predetermined number of carbon atoms are mentioned. have.

Examples of the substituent include ethylenically unsaturated groups such as vinyl, allyl, acryl, and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; Acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, jade acyl groups such as saloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl and carbamoyl; acyloxy groups such as acetyloxy 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- Octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N,N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonyl substituted amino groups such as amino; 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 group and salts of an acid group and a phosphoric acid group, and these groups may be further substituted in some cases. Moreover, a carboxyl group and a sulfo group may form the salt.

In the general formula (IA), when n is 2 to 6, X ¹ may be represented by the following general formulas (1) to (5), respectively.

(In the general formula (1), Y ¹ is a single bond, -CR ⁵ R ⁶ -, -NR ⁷ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an aromatic hydrocarbon having 6 to 35 carbon atoms. a group or a heterocyclic ring-containing group having 2 to 35 carbon atoms, or any substituent represented by the following (1-1) to (1-3);

The aliphatic hydrocarbon group is, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or oxygen atoms are not adjacent to each other and these It may be substituted with a combined bonding group,

Z ¹ and Z ² are each independently a direct bond, -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -SS-, -SO-, -NR ⁷ - or -PR ⁷ -,

R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic hydrocarbon having 6 to 35 carbon atoms which may have a substituent Represents a heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a group or a substituent,

* means to combine with an adjacent group in the * part.)

(In the formula, R ⁸ represents a hydrogen atom or a optionally substituted phenyl group or a cycloalkyl group having 3 to 10 carbon atoms,

R ⁹ 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 have a substituent In some cases,

f is an integer from 0 to 5,

* means to combine with an adjacent group in the * part.)

(* means combining with an adjacent group in the * part.)

(Wherein, R ¹⁰ and R ¹¹ are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and a substituent An aryloxy group having 6 to 20 carbon atoms which may have a substituent, an arylthio group having 6 to 20 carbon atoms which may have a substituent, and an arylalkyl group having 6 to 20 carbon atoms which may have a substituent represents a nyl group, an arylalkyl group having 7 to 20 carbon atoms which may have a substituent, a heterocycle-containing group having 2 to 20 carbon atoms or a halogen atom which may have a substituent;

The methylene group in the alkyl group and the arylalkyl group may be substituted with an unsaturated bond, -O- or -S-,

R ¹⁰ may form a ring with adjacent R ^{10 ,}

p represents a number from 0 to 4,

q represents a number from 0 to 8,

g represents a number from 0 to 4,

h represents a number from 0 to 4,

The sum of the numbers g and h is 2-4,

* means to combine with an adjacent group in the * part.)

(In the 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, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a carbon atom represents a heterocycle-containing group of numbers 2-35,

Z ¹ , Z ² and Z ³ are each independently a direct bond, -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -SS-, - SO-, -NR _12- or -PR ₁₂ -,

R ¹² is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent or carbon which may have a substituent represents a heterocyclic-containing group having 2 to 35 atoms,

The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or oxygen atoms are mutually It may be substituted with a bonding group that is not adjacent to each other and combines them,

* means to combine with an adjacent group in the * part.)

(In the general formula (3), Y ¹² is a carbon atom, or a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic ring having 2 to 35 carbon atoms. represents the flag,

The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,

Z ¹ to Z ⁴ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),

* means to combine with an adjacent group in the * part.)

(In the general formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,

The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,

Z ¹ to Z ⁵ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),

* means to combine with an adjacent group in the * part.)

(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 heterocycle-containing group having 2 to 35 carbon atoms,

The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,

Z ¹ to Z ⁶ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),

* means to combine with an adjacent group in the * part.)

In the general formula (1), the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by ^{R 5} , R ⁶ and R ^{7 is represented by X 1 in the general formula (IA).} A predetermined number of carbon atoms among monovalent aliphatic hydrocarbon groups exemplified as n-valent bonding groups, and groups substituted by those exemplified as substituents of groups in which these groups represent an n-valent bonding group represented by ^{X 1 in the above general formula (IA)} It can be mentioned that it satisfies

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, which may have a substituent, represented by R ⁵ , R ⁶ and R ⁷ are exemplified as the n-valent bonding group represented by ^{X 1 in the above general formula (IA).} Among the monovalent aromatic ring-containing hydrocarbon groups, and groups substituted by those exemplified as substituents of the groups in which these groups represent an n-valent bonding group represented by ^{X 1 in the general formula (IA), those satisfying a predetermined number of carbon atoms} and the like,

As the heterocyclic-containing group having 2 to 35 carbon atoms, which may have a substituent, represented by ^{R 5} , R ⁶ and R ⁷ , is one exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA).} Among the valent heterocyclic-containing groups and groups substituted by those exemplified as substituents of the groups representing the n-valent bond represented by ^{X 1 in the general formula (IA), those satisfying a predetermined number of carbon atoms, etc.} can be heard

In addition, as the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented ^{by Y 1} in the general formula (1), the divalent aliphatic hydrocarbon group exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA).} groups and groups substituted by those exemplified as substituents of the groups in which ^{these groups represent an n-valent bonding group represented by X 1} in the general formula (IA) above, those satisfying a predetermined number of carbon atoms;

Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹ include the divalent aromatic ring-containing hydrocarbon groups ^{exemplified as the n-valent bonding group represented by X 1 in the general formula (IA), and these groups are} Among the groups substituted by those exemplified as the substituent of the group representing the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms are exemplified;

As the divalent heterocyclic ring-containing group having 2 to 35 carbon atoms represented by ^{Y 1} , the divalent aromatic ring-containing hydrocarbon group exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these groups are the general} Among the groups substituted by those exemplified as the substituent of the group representing the n-valent bonding group represented by ^{X 1} in the formula (IA), those satisfying a predetermined number of carbon atoms are exemplified.

In the substituent represented by (1-1) above, examples of the cycloalkyl group having 3 to 10 carbon atoms represented by ^{R 8 include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl and cyclooctyl;}

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ⁹ include groups satisfying a predetermined number of carbon atoms among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by ^{R 1} and R ^{2 ,} ,

Examples ^{of the alkoxy group having 1 to 10 carbon atoms represented by R 9} include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyl Oxy, tertiary amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyl oxy and decyloxy;

The substituents of the phenyl group, the cycloalkyl group, the alkyl group, the alkoxy group and the alkenyl group are the same as those exemplified as the substituents of the n-valent bonding group represented by ^{X 1 in the general formula (IA).}

In the group represented by (1-3) above, the alkyl group having 1 to 10 carbon atoms which may have a substituent represented by ^{R 10} and R ¹¹ includes 1 to 40 carbon atoms represented by ^{R 1} and R ^{2 .} Among the groups exemplified as the alkyl group of

Examples of the optionally substituted aryl group having 6 to 20 carbon atoms represented by R ¹⁰ and R ¹¹ include groups exemplified as the aryl group having 6 to 20 carbon atoms represented by ^{R 1} and R ^{2 .} there is,

Examples of the ^{optionally substituted aryloxy group having 6 to 20 carbon atoms represented by R 10} and R ¹¹ include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4 -Vinylphenyloxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hexylphenyloxy, 4-cyclohexylphenyloxy, 4- Octylphenyloxy, 4-(2-ethylhexyl)phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2.6-dimethylphenyloxy, 3.4-dimethylphenyloxy , 3.5-dimethylphenyloxy, 2,4-di-tert-butylphenyloxy, 2,5-di-tert-butylphenyloxy, 2,6-di-tert-butylphenyloxy, 2.4-di-tert-pentyl and groups such as phenyloxy, 2,5-tert-amylphenyloxy, 4-cyclohexylphenyloxy, 2,4,5-trimethylphenyloxy, and ferrocenyloxy;

As the ^{optionally substituted arylthio group having 6 to 20 carbon atoms represented by R 10} and R ¹¹ , the oxygen atom of the optionally substituted aryloxy group having 6 to 20 carbon atoms is replaced with sulfur and groups substituted with atoms;

As the ^{optionally substituted arylalkenyl group having 8 to 20 carbon atoms represented by R 10} and R ¹¹ , the oxygen atom of the optionally substituted aryloxy group having 6 to 20 carbon atoms is and groups substituted with alkenyl groups such as vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, and 2-octenyl;

Examples of the optionally substituted arylalkyl group having 7 to 20 carbon atoms represented by R ¹⁰ and R ¹¹ include the groups exemplified as the arylalkyl group having 7 to 20 carbon atoms represented ^{by R 1} and R ^{2 .} there is,

Examples of the heterocyclic group having 2 to 20 carbon atoms which may have a substituent represented by R ¹⁰ and R ¹¹ include the groups exemplified as the heterocyclic group having 2 to 20 carbon atoms represented ^{by R 1} and R ^{2 , etc.} can be heard

Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by ^{Y 11} in the general formula (2) include the trivalent aliphatic hydrocarbon group exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA);} Among the groups substituted by the substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms, etc., are substituted with ^{Z 1} , Z ² and Z ^{3 .} and trivalent groups that have been

^{Examples of the trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by Y 11} in the general formula (2) include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2 -Adamantyl, noradamantyl, 2-methyladamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo[1.1.0]butyl, bicyclo[1.1. 1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[3.1.0]hexyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.0]hexyl, bicyclo[4.1.0]heptyl, bi Cyclo[3.2.0]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[5.1.0]octyl, bicyclo[4.2.0]octyl, bicyclo[4.1.1 ]octyl, bicyclo[3.3.0]octyl, bicyclo[3.2.1]octyl, bicyclo[2.2.2]octyl, spiro[4,4]nonanyl, spiro[4,5]decanyl, decalin, and trivalent groups derived from groups such as tricyclodecanyl, tetracyclododecanyl, cedrol and cyclododecanyl;

As the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by ^{Y 11} , the trivalent aromatic ring-containing hydrocarbon group exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these groups are the general} Among the groups substituted by those exemplified as the substituent of the n-valent bonding group represented by ^{X 1} in the formula (IA), those satisfying a predetermined number of carbon atoms are exemplified;

As the trivalent heterocycle-containing group having 2 to 35 carbon atoms represented by ^{Y 11} , the trivalent heterocycle-containing group exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these groups are represented by the general formula (} Among the groups substituted by those exemplified as the substituent of the n-valent bonding group represented by ^{X 1} in IA), those satisfying a predetermined number of carbon atoms are exemplified.

In addition, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent, and a substituent represented by ^{R 12 , which may have a substituent} Examples of the heterocycle-containing group having 2 to 35 carbon atoms include the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocycle-containing group exemplified in the description ^{of R 5} , R ⁶ and R ^{7 in the above general formula (1), respectively.} can be heard

Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented ^{by Y 12} in the general formula (3) include the monovalent to trivalent aliphatic groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA).} Among hydrocarbon groups and tetravalent groups derived from groups substituted by those exemplified as substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms, etc. can,

Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹² include monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these} Among the tetravalent groups derived from the group substituted by those exemplified as the substituent of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms, etc. are mentioned;

Examples of the tetravalent heterocycle-containing group having 2 to 35 carbon atoms represented by Y ¹² include the monovalent to trivalent heterocycle-containing groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these groups are} Among the tetravalent groups derived from the groups substituted by those exemplified as the substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms are exemplified.

Examples of the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by ^{Y 13} in the general formula (4) include the monovalent to trivalent aliphatic groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA).} Among hydrocarbon groups and pentavalent groups derived from groups substituted by those exemplified as substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms, etc. are mentioned. can,

Examples of the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹⁴ include monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these} Among the pentavalent groups derived from the group substituted by those exemplified as the substituent of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms are exemplified;

Examples of the pentavalent heterocycle-containing group having 2 to 35 carbon atoms represented by Y ¹⁴ include the monovalent to trivalent heterocyclic-containing groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these groups are} Among the pentavalent groups derived from the groups substituted by those exemplified as the substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms are exemplified.

Examples of the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by ^{Y 14} in the general formula (5) include the monovalent to trivalent aliphatic groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA).} Among hydrocarbon groups and hexavalent groups derived from groups substituted by those exemplified as substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms, etc. are mentioned. can,

Examples of the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹⁴ include monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the n-valent bonding group represented by ^{X 1 in the general formula (IA), and these} Among the hexavalent groups in which the group is derived from a group substituted by those exemplified as a substituent of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms are exemplified;

Examples of the hexavalent heterocyclic-containing group having 2 to 35 carbon atoms represented by Y ¹⁴ include the monovalent to trivalent heterocyclic-containing groups exemplified as the n-valent bonding group represented by ^{X 1 in the above general formula (IA), and these groups are} Among the hexavalent groups derived from the groups substituted by those exemplified as the substituents of the n-valent bonding group represented by ^{X 1} in the general formula (IA), those satisfying a predetermined number of carbon atoms are exemplified.

Among the compounds represented by the general formula (I-A), those represented by the following general formulas (II-1) to (II-3) are preferable because their heat resistance increases.

(Wherein, R ⁸² , R ⁸³ and R ⁸⁴ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms which may have a substituent. , 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 ¹ and R ² are the same as those of the general formula (I). )

(wherein, r=2 to 6, X ² is a group represented by the general formula (1) when r=2, a group represented by the general formula (2) when r=3, and r=4 a group represented by the above general formula (3) when, r = the fifth day, and the formula (4), r = 6 days when the formula (5) and, r ⁹² and r ⁹³ are each independently hydrogen An atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms, or an aryl group having 7 to 20 carbon atoms represents an arylalkyl group or a heterocycle-containing group having 2 to 20 carbon atoms, and R ¹ and R ² are the same as in the above general formula (I).)

(Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , and R ²⁰⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, and a substituent the number is also carbon atom to which the case has 1 to 40 alkyl group, a heterocyclic ring of carbon atoms from 6 to 20 aryl group, a carbon atom number of 7-20 arylalkyl group or 2 to 20 carbon atoms of the monovalent contained, Y ¹ , Z ¹ and Z ² are the same as in General Formula (1).)

^{A halogen atom represented by R 82} , R ⁸³ and R ⁸⁴ in the general formula (II-1), an optionally substituted alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and carbon Examples of the arylalkyl group having 7 to 20 atoms and the heterocyclic group having 2 to 20 carbon atoms include those exemplified in the description ^{of R 1} and R ^{2 in the general formula (I).}

^{A halogen atom represented by R 92} and R ⁹³ in the general formula (II-2), an alkyl group having 1 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms, and 7 carbon atoms Examples of the -20 arylalkyl group and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified in the description ^{of R 1} and R ^{2 in the general formula (I).}

^{A halogen atom represented by R 201} , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ in the general formula (II-3), optionally having a substituent, having 1 to carbon atoms As the alkyl group of 40, the aryl group of 6 to 20 carbon atoms, the arylalkyl group of 7 to 20 carbon atoms, and the heterocycle-containing group of 2 to 20 carbon atoms, R ¹ and R ^{2 in the above general formula (I)} those exemplified in the description of

Among the compounds represented by the general formula (II-1),

R ¹ is a branched alkyl group having 1 to 8 carbon atoms, particularly t-butyl group, and R ² is a hydrogen atom; R ⁸² , R ⁸³ and R ⁸⁴ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, 1 to carbon atoms It is preferable that it is a 10 heterocyclic ring-containing group, especially, ^{that any one of R 82} , R ⁸³ and R ⁸⁴ is a C1-C4 alkyl group or a C1-C10 heterocyclic-containing group.

Among the compounds represented by the general formula (II-2),

R ¹ is a branched alkyl group having 1 to 8 carbon atoms, particularly t-butyl group, and R ² is a hydrogen atom; R ⁹² and R ⁹³ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or a compound having 1 to 10 carbon atoms It is preferable that it is a ring-containing group, in particular, that R ⁹² or R ⁹³ is an alkyl group having 1 to 4 carbon atoms or a heterocyclic group containing 1 to 10 carbon atoms.

When X ² is the general formula (1), Y ¹⁰ is a sulfur atom, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, and 2 to carbon atoms A divalent heterocyclic-containing group of 21, a divalent group derived from 2,4,8,10-tetraoxaspiro[5,5]undecane, in particular, an alkylene group having 1 to 15 carbon atoms, 6 carbon atoms It is preferable that it is a divalent group derived from a divalent aromatic ring-containing hydrocarbon group of 15, 2,4,8,10-tetraoxaspiro[5,5]undecane,

Z ¹ and Z ² are a direct bond, -CO-O-, -O-CO-, or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 10 carbon atoms, particularly It is preferable that it is a C1-C8 aliphatic hydrocarbon group which may have a substituent.

When X ² is the formula (2), Y ¹¹ is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or 1 carbon atom. A trivalent group derived from a ˜10 heterocyclic group, in particular, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 9 carbon atoms, or 3 derived from a heterocyclic group having 1 to 6 carbon atoms It is preferable that it is a group of

Z ¹ , Z ² and Z ³ are preferably the same as ^{Z 1} and Z ^{2 ,}

When X ² is the above general formula (3), Y ¹² is preferably a tetravalent group corresponding to the group mentioned above as ^{Y 11 preferred,}

Z ¹ to Z ⁴ are preferably the same as ^{Z 1} and Z ^{2 ,}

When X ² is the above general formula (4), Y ¹³ is preferably a pentavalent group corresponding to the group mentioned above as ^{Y 11 ,}

Z ¹ to Z ⁵ are preferably the same as ^{Z 1} and Z ^{2 ,}

When X ² is represented by the general formula (5), Y ¹⁴ is preferably a hexavalent group corresponding to the above-mentioned group as preferred Y ^{11 ,}

Z ¹ to Z ⁶ are preferably the same as ^{Z 1} and Z ^{2 .}

Among the compounds represented by the general formula (I), compounds represented by the following formula are preferable, but the present invention is not limited to these compounds.

Although the manufacturing method of the compound which has a substituent represented by the said general formula (I) is not specifically limited, For example, Unexamined-Japanese-Patent No. 57-111375, Unexamined-Japanese-Patent No. 3-173843, Unexamined-Japanese-Patent No. 6-128195. No. 7-206771, Japanese Patent Application Laid-Open No. Hei 7-252191, and Japanese Patent Application Laid-Open No. 2004-501128 can be obtained by reacting a phenol-based compound prepared by the method described in each of the publications, and an allyl halide compound. have.

The compound which has a substituent represented by the said general formula (I) can be used as a latent additive in the photosensitive composition of this invention.

The latent additive is inert in the pre-baking process at room temperature or 150° C. or less, for example, 150° C. or less, and is heated to 100-250° C. or heated to 80-200° C. in the presence of an acid/base catalyst By doing so, the protecting group is released and becomes active.

In the photosensitive composition of the present invention, the content of the compound having a substituent represented by the general formula (I) as a latent additive is preferably 0.001 to 20 mass%, more preferably 0.005 to 5 mass%, in the solid content of the composition of the present invention. desirable.

The photosensitive composition of the present invention is a composition whose properties change by irradiation with light, a positive resist for being soluble to a chemical reaction, and a negative for being insoluble to a chemical reaction There is a type resist. The photosensitive composition of the present invention contains, as a latent antioxidant, a compound having a substituent represented by the general formula (I), a polymerizable compound having an ethylenically unsaturated bond having an acid value, and a radical photopolymerization initiator as essential components include as

Examples of the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth)acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, and vinylacetic acid. , allylacetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono[2-(meth)acryloyloxyethyl], phthalic acid mono[2-(meth)acryloyloxyethyl], ω-carboxypolycaprolactone mono(meth) ) Polymer mono (meth) acrylate, hydroxyethyl (meth) acrylate maleate, hydroxypropyl (meth) acrylate maleate, dicy Unsaturated polybasic acids, such as polyfunctional (meth)acrylate which has clopentadiene maleate or one carboxyl group and two or more (meth)acryloyl groups; Novolak epoxy compounds, such as phenol and/or cresol novolac epoxy resins, novolac epoxy resins having a biphenyl skeleton and naphthalene skeleton, bisphenol A novolak epoxy compounds, and dicyclopentadien novolak epoxy compounds, polyfunctional A polyphenylmethane type epoxy resin having an epoxy group, a resin in which an unsaturated monobasic acid is made to act on an epoxy group of an epoxy resin such as an epoxy compound represented by the following general formula (III), an unsaturated monobasic acid is made to act on an epoxy group of an epoxy resin, and A resin obtained by reacting a polybasic acid anhydride, a hydroxyl group-containing polyfunctional acrylate such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate, and an acid value that is a reaction product of a dibasic acid anhydride such as succinic anhydride, phthalic anhydride, and tetrahydrophthalic anhydride and polyfunctional acrylates having

(wherein, X ⁴¹ is a direct bond, an alkylene group having 1 to 4 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, -O-, -S-, -SO ₂ -, -SS-, -SO-, -CO-, -OCO- or a substituent represented by the above (1-1) to (1-3);

R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms which may have a substituent, or an alkoxy group having 1 to 8 carbon atoms which may have a substituent Represents an alkenyl group or halogen atom having 2 to 5 carbon atoms which may have a group or a substituent,

m is an integer from 0 to 10.)

The polymeric compound which has an ethylenically unsaturated bond which has these acid values can be used individually or in mixture of 2 or more types, Moreover, it can use in combination with the polymeric compound which has an ethylenically unsaturated bond which does not have an acid value. When using 2 or more types in mixture, you may copolymerize them beforehand and you may use them as a copolymer.

In the photosensitive composition of the present invention, the content of the polymerizable compound having an ethylenically unsaturated bond having an acid value is preferably 20 to 80 mass %, more preferably 30 to 70 mass % in the solid content of the composition of the present invention. .

Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include (meth)acrylic acid-2-hydroxyethyl, (meth)acrylic acid-2-hydroxypropyl, (meth)acrylic acid glycidyl. , the following compounds No. A1 to No. A4, (meth) methyl acrylate, (meth) acrylate, (meth) acrylate isobutyl, (meth) acrylic acid-t-butyl, (meth) acrylic acid cyclohexyl, (meth) acrylic acid n-octyl, (meth) acrylate isooctyl, (meth) acrylate isononyl, (meth) acrylate stearyl, (meth) acrylate lauryl, (meth) acrylate methoxyethyl, (meth) acrylate dimethylaminomethyl, ( Dimethylaminoethyl (meth)acrylate, aminopropyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, ethoxyethyl (meth)acrylate, poly(ethoxy)ethyl (meth)acrylate, butoxyethoxyethyl (meth)acrylate , (meth) ethylhexyl acrylate, (meth) acrylate phenoxyethyl, (meth) acrylate tetrahydrofuryl, (meth) acrylate vinyl, (meth) acrylate allyl, (meth) acrylate benzyl, 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, trimethylolethane tri (meth) acrylate, trimethylol propane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, tricyclodecanedimethyloldi(meth)acrylate, tri[(meth)acryloylethyl]isocyanu esters of unsaturated monobasic acids and polyhydric alcohols or polyhydric phenols such as esters and polyester (meth)acrylate oligomers; metal salts of unsaturated polybasic acids such as zinc (meth)acrylate and magnesium (meth)acrylate; Maleic anhydride, itaconic anhydride, citraconic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3 - Acid anhydrides of unsaturated polybasic acids, such as cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride, dodecenyl succinic anhydride, and methylhimic anhydride; (meth)acrylamide, methylenebis-(meth)acrylamide, diethylenetriaminetris(meth)acrylamide, xylylenebis(meth)acrylamide, α-chloroacrylamide, N-2-hydroxyethyl ( amides of unsaturated monobasic acids and polyvalent amines such as meth)acrylamide; unsaturated aldehydes such as acrolein; unsaturated nitriles such as (meth)acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, and allyl cyanide; Styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzenesulfonic acid unsaturated aromatic compounds such as vinyl benzyl methyl ether and vinyl benzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; unsaturated amine compounds such as vinylamine, allylamine, N-vinylpyrrolidone and vinylpiperidine; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, and allyl glycidyl ether; unsaturated imides such as maleimide, N-phenylmaleimide, and N-cyclohexylmaleimide; indene, such as indene and 1-methylindene; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; macromonomers having a mono(meth)acryloyl group at the terminal of the polymer molecular chain, such as polystyrene, polymethyl(meth)acrylate, poly-n-butyl(meth)acrylate, and polysiloxane; Other vinyl compounds such as (meth)acrylonitrile, ethylene, propylene, butylene, vinyl chloride, and vinyl acetate, and macromonomers such as polymethylmethacrylate macromonomer and polystyrene macromonomer, tricyclodecane skeleton mono Copolymers of methacrylate, N-phenylmaleimide, methacryloyloxymethyl-3-ethyloxetane, etc., and (meth)acrylic acid A copolymer of (meth)acrylic acid reacted with an isocyanate compound having a bond, vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphite, triallyl isocyanurate, vinyl thioether, vinyl Imidazole, vinyloxazoline, vinylcarbazole, vinylpyrrolidone, vinylpyridine, vinylurethane compounds of hydroxyl group-containing vinyl monomers and polyisocyanate compounds, vinylepoxy compounds of hydroxyl group-containing vinyl monomers and polyepoxy compounds, pentaerythritol tri The reaction product of polyfunctional acrylates containing hydroxyl groups, such as acrylate and dipentaerythritol pentaacrylate, and polyfunctional isocyanate, such as tolylene diisocyanate and hexamethylene diisocyanate, etc. are mentioned.

In order to improve the developability of the photosensitive composition of this invention by adjusting an acid value, with the polymeric compound which has an ethylenically unsaturated bond which has the said acid value, a monofunctional or polyfunctional epoxy compound can also be used. The polymerizable compound having an ethylenically unsaturated bond having the acid value is preferably in the range of 5 to 120 mgKOH/g with an acid value of solid content, and the amount of monofunctional or polyfunctional epoxy compound used is selected to satisfy the acid value it is 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, Dil 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 Cidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether Cydyl ether, propargyl glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxy glycidyl ether, p-butylphenol glycidyl ether, crezyl glycidyl ether Dil ether, 2-methylcrezyl 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-vinylcyclohexane, styrene oxide, pinene oxide, methylstyrene oxide , cyclohexene oxide, propylene oxide, and the like.

As said polyfunctional epoxy compound, when 1 or more types chosen from the group which consists of a bisphenol-type epoxy compound and glycidyl ethers are used, since the photosensitive composition with a further favorable characteristic can be obtained, it is preferable. As said bisphenol-type epoxy compound, besides being able to use the epoxy compound represented by the said General formula (III), bisphenol-type epoxy compounds, such as a hydrogenated bisphenol-type epoxy compound, can also be used, for example. 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, tri Ethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri(glycidyl ether) Dyloxymethyl) propane, 1,1,1-tri(glycidyloxymethyl)ethane, 1,1,1-tri(glycidyloxymethyl)methane, 1,1,1,1-tetra(glycy diloxymethyl)methane.

In addition, novolak-type epoxy compounds, such as a phenol novolak-type epoxy compound, a biphenyl novolak-type epoxy compound, a cresol novolak-type epoxy compound, a bisphenol A novolak-type epoxy compound, and a dicyclopentadien novolak-type epoxy compound; 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl alicyclic epoxy compounds such as -3,4-epoxycyclohexane; glycidyl esters such as phthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester and dimer acid glycidyl ester; glycidylamines such as tetraglycidyldiaminodiphenylmethane, 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 dicyclopentadienedioxide; A naphthalene type epoxy compound, a triphenylmethane type epoxy compound, a dicyclopentadiene type epoxy compound, etc. can also be used.

The radical photopolymerization initiator may be any compound capable of initiating radical polymerization upon exposure to light, for example, ketone compounds such as acetophenone compounds, benzyl compounds, benzophenone compounds, and thioxanthone compounds. , an oxime-based compound, and the like can be exemplified as preferable.

Examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 4'-isopropyl-2-hydroxy-2-methylpropiophenone. , 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, p-dimethylaminoacetophenone, p-tertiary butyldichloroaceto Phenone, p-tertbutyltrichloroacetophenone, p-azidebenzalacetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinoff Ropanone-1,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin phosphorus-n-butyl ether, benzoin isobutyl ether, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, and the like. have.

Benzyl, anisyl, etc. are mentioned as a benzyl-type compound.

Examples of the benzophenone compound include benzophenone, o-benzoyl methyl benzoate, Michler ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 4-benzoyl-4 '-methyldiphenyl sulfide, etc. are mentioned.

As thioxanthone-based compounds, thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, etc. can be heard

As the oxime-based compound, a compound represented by the following general formula (IV) or (V) is particularly preferred in terms of sensitivity and heat resistance.

(Wherein, R ⁵¹ and R ⁵² are each independently a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkyl group having 6 to 30 carbon atoms which may have a substituent an aryl group, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, or a heterocyclic ring-containing group having 2 to 20 carbon atoms which may have a substituent;

R ⁵³ and R ⁵⁴ are each independently a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R ⁵⁵ , OR ⁵⁶ , SR ⁵⁷ , NR ⁵⁸ R ⁵⁹ , COR ⁶⁰ , SOR ⁶¹ , SO ₂ R ⁶² or CONR ⁶³ R ⁶⁴ , R ⁵³ and R ⁵⁴ may be bonded to each other to form a ring,

R ⁵⁵ , R ⁵⁶ , R ⁵⁷ , R ⁵⁸ , R ⁵⁹ , R ⁶⁰ , R ⁶¹ , R ⁶² , R ⁶³ and R ⁶⁴ are each independently an optionally substituted alkyl group having 1 to 20 carbon atoms; An aryl group having 6 to 30 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, or a heterocyclic ring having 2 to 20 carbon atoms which may have a substituent represents a containing group,

X ³ represents an oxygen atom, a sulfur atom, a selenium atom, CR ⁷⁵ R ⁷⁶ , CO, NR ⁷⁷ or PR ⁷⁸ ;

X ⁴ represents a single bond or CO,

R ⁷⁵ to R ⁷⁸ represent 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, and the methylene group in the alkyl group or arylalkyl group is a halogen atom; It may be substituted with a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, or may be substituted with -O-;

R ⁵³ and R ⁵⁴ may each independently form a ring with one of the adjacent benzene rings,

a represents an integer of 0 to 4,

b represents an integer of 0-5.)

(Wherein, R ¹⁰¹ and R ¹⁰² each independently represent R ¹¹¹ , OR ¹¹¹ , COR ¹¹¹ , SR ¹¹¹ , CONR ¹¹² R ¹¹³ or CN,

R ¹¹¹ , R ¹¹² and R ¹¹³ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an arylalkyl group having 2 to carbon atoms 20 represents a heterocycle-containing group,

The hydrogen atom of the group represented by R ¹¹¹ , R ¹¹² and R ^{113 is further R 121} , OR ¹²¹ , COR ¹²¹ , SR ¹²¹ , NR ¹²² R ¹²³ , CONR ¹²² R ¹²³ , -NR ¹²² -OR ¹²³ , -NCOR ¹²² - OCOR ¹²³ , NR ¹²² COR ¹²¹ , OCOR ¹²¹ , COOR ¹²¹ , SCOR ¹²¹ , OCSR ¹²¹ , COSR ¹²¹ , CSOR ¹²¹ , may be substituted with a hydroxyl group, a nitro group, CN or a halogen atom;

R ¹²¹ , R ¹²² and R ¹²³ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an arylalkyl group having 2 to carbon atoms 20 represents a heterocycle-containing group,

The hydrogen atom of the group represented by R ¹²¹ , R ¹²² and R ¹²³ may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group,

The ^{alkylene moiety of the group represented by R 111} , R ¹¹² , R ¹¹³ , R ¹²¹ , R ¹²² and R ¹²³ is -O-, -S-, -COO-, -OCO-, -NR ¹²⁴ -, -NR ¹²⁴ In some cases, oxygen atoms are substituted 1 to 5 times by COO-, -OCONR ¹²⁴ -, -SCO-, -COS-, -OCS- or -CSO- under the condition that they are not adjacent to each other,

R ¹²⁴ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,

The alkyl moiety of the group represented by R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹²¹ , R ¹²² , R ¹²³ and R ¹²⁴ may have a branched side chain or may be cyclic alkyl,

R ¹⁰³ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms, R ^{The alkyl portion of the group represented by 103} may have a branched chain or may be cyclic alkyl, and R ¹⁰³ and R ¹⁰⁷ , R ¹⁰³ and R ¹⁰⁸ , R ¹⁰⁴ and R ¹⁰⁵ , R ¹⁰⁵ and R ¹⁰⁶ and R ¹⁰⁶ and R ¹⁰⁷ may each become one to form a ring,

The hydrogen atom of the group represented by R ^{103 is further R 121} , OR ¹²¹ , COR ¹²¹ , SR ¹²¹ , NR ¹²² R ¹²³ , CONR ¹²² R ¹²³ , -NR ¹²² -OR ¹²³ , -NCOR ¹²² -OCOR ¹²³ , NR ¹²² COR ¹²¹ , OCOR ¹²¹ , COOR ¹²¹ , SCOR ¹²¹ , OCSR ¹²¹ , COSR ¹²¹ , CSOR ¹²¹ , a hydroxyl group, a nitro group, CN, a halogen atom, or may be substituted with ^{COOR 121 ,}

R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ are each independently R ¹¹¹ , OR ¹¹¹ , SR ¹¹¹ , COR ¹¹⁴ , CONR ¹⁵¹ R ¹¹⁶ , NR ¹¹² COR ¹¹¹ , OCOR ¹¹¹ , COOR ¹¹⁴ , SCOR ¹¹¹ , OCSR ¹¹¹ , COSR ¹¹⁴ , CSOR ¹¹¹ , a hydroxyl group, CN or a halogen atom, R ¹⁰⁴ and R ¹⁰⁵ , R ¹⁰⁵ and R ^{106 ,} and R ¹⁰⁶ and R ¹⁰⁷ may each form a ring as one,

R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

R ¹⁰⁸ is R ¹¹¹ , OR ¹¹¹ , SR ¹¹¹ , COR ¹¹¹ , CONR ¹¹² R ¹¹³ , NR ¹¹² COR ¹¹¹ , OCOR ¹¹¹ , COOR ¹¹¹ , SCOR ¹¹¹ , OCSR ¹¹¹ , COSR ¹¹¹ , CSOR ¹¹¹ , hydroxyl group, CN or halogen atom represents,

w represents 0 or 1.)

Examples of other radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(cyclopentadienyl)-bis[2,6-difluoro-3-(pil-1-yl) ]Titanium etc. are mentioned.

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

As for content of the above radical photopolymerization initiators, 0.1-30 mass %, especially 0.5-10 mass % is preferable in solid content of the photosensitive composition of this invention. When content of the said radical photopolymerization initiator is smaller than 0.1 mass %, hardening by exposure may become inadequate, and when larger than 30 mass %, an initiator may precipitate in the photosensitive composition.

The photosensitive composition of this invention can also add a coloring agent and can also be set as a coloring photosensitive composition. The hardened|cured material of the said coloring photosensitive composition is used suitably as a color filter.

The coloring photosensitive composition of this invention WHEREIN: 0.01-50 mass % is preferable in solid content of the coloring photosensitive composition of this invention, and, as for the addition amount of a coloring agent, 0.1-30 mass % is more preferable. When content of the said coloring agent is less than 0.01 mass %, desired chromaticity may not be acquired, and when larger than 50 mass %, a coloring agent may precipitate in the coloring photosensitive composition.

Dyes or pigments may be mentioned as the colorant.

The dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm, and for example, an azo compound, an anthraquinone compound, an indigoid compound, a triarylmethane compound, a xanthene compound, an alizarin compound, an acridine compound , stilbene compound, thiazole compound, naphthol compound, quinoline compound, nitro compound, indamine compound, oxazine compound, phthalocyanine compound, cyanine compound, diimmonium compound, cyanoethenyl compound, dicyanostyrene compound, rhodamine compound , perylene compound, polyennaphtholactam compound, coumarin compound, squarium compound, croconium compound, spiropyran compound, spirooxazine compound, merocyanine compound, oxonol compound, styryl compound, pyrylium compound, rhodanine compound, oxazolone compound, phthalimide compound, cinnoline compound, naphthoquinone compound, azaanthraquinone compound, porphyrin compound, azaporphyrin compound, pyromethene compound, quinacridone compound, diketopyrrolopyrrole compound, indigo compound, and dyes such as acridine compound, azine compound, azomethine compound, aniline compound, quinacridone compound, quinophthalone compound, quinoneimine compound, iridium complex compound, europium complex compound, etc. may be used.

An inorganic pigment or an organic pigment can be used as the pigment, for example, a nitroso compound, a nitro compound, an azo compound, a diazo compound, a xanthene compound, a quinoline compound, an anthraquinone compound, a coumarin compound, a phthalocyanine compound, isoin Dolinone compound, isoindoline compound, quinacridone compound, ananthrone compound, perinone compound, perylene compound, diketopyrrolopyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compound, quinophthalone compound, naphthalenetetracarboxylic acid; metal complex compounds of azo dyes and cyanine dyes; lake pigment; carbon black obtained by a furnace method, a channel method, or a thermal method, or carbon black such as acetylene black, ketjen black, or lamp black; The carbon black is adjusted and coated with an epoxy resin, the carbon black is previously dispersed with a resin in a solvent, and 20 to 200 mg/g of the resin is adsorbed, and the carbon black is surface-treated with an acidic or alkaline surface , having an average particle size of 8 nm or more and a DBP oil absorption of 90 ml/100 g or less, CO in volatile matter at 950° C., _{and the total oxygen content calculated from CO 2} is 9 mg or more per 100 m 2 of surface area of carbon black; graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon airgel, fullerene; Aniline Black, Pigment Black 7, Titanium Black; Hydrophobic resin, chromium oxide green, milory blue, cobalt green, cobalt blue, manganese, ferrocyanide, phosphate ultramarine blue, blue blue, ultramarine, cerulean blue, viridian, emerald green, lead sulfate, yellow Inorganic or organic pigments such as lead, zinc sulfur, bengala (red iron (III) oxide), cadmium red, synthetic iron black, and amber can be used. These pigments can be used individually or in mixture of two or more.

A commercially available pigment may be used as the inorganic or organic pigment, 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, 93, 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, etc. are mentioned.

A solvent can be further added to the photosensitive composition and coloring photosensitive composition of this invention. The solvent is usually a solvent capable of dissolving or dispersing each of the above components as needed, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone. ketones such as , cyclohexanone and 2-heptanone; ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, and dipropylene glycol dimethyl ether; ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, and diacetone alcohol; Ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate, ether ester solvents such as 1-t-butoxy-2-propanol, 3-methoxybutyl acetate, and cyclohexanol acetate; BTX solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as hexane, heptane, octane, and cyclohexane; terpene hydrocarbon oils such as turpentine, D-limonene and pinene; Paraffinic solvents, such as mineral spirit, Swasol #310 (Cosmo Matsuyama Sekiyu Co., Ltd.), and Solvesso #100 (Exxon Chemical Co., Ltd.); halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; Carbitol solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, water, etc. and these solvents may be used as one type or a mixed solvent of two or more types. Among these, ketones, ether ester solvents, etc., especially propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, etc. are preferable because they have good compatibility between the resist and the radical photopolymerization initiator in the photosensitive composition. do. When using a solvent, it is preferable from a viewpoint of handling etc. to use it in the quantity used as 25-35 mass % of solid content of the photosensitive composition or coloring photosensitive composition of this invention.

The photosensitive composition and colored photosensitive composition of the present invention may 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; Layered clay mineral, milori blue, calcium carbonate, magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfide, selenide, aluminum silicate, calcium A silicate, aluminum hydroxide, platinum, gold|metal|money, silver, copper, etc. are mentioned.

In the photosensitive composition and colored photosensitive composition of the present invention, when a colorant such as a pigment and/or an inorganic compound is used, a dispersing agent may be added. The dispersant is not particularly limited as long as it is capable of dispersing and stabilizing colorants and inorganic compounds, and commercially available dispersants such as Bikk Chemie, BYK series, etc. can be used, and polyesters and polyethers having a basic functional group Polymer dispersing agent made of 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 is preferably used.

Moreover, to the photosensitive composition and coloring photosensitive composition of this invention, thermal polymerization inhibitors, such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, and phenothiazine, as needed; plasticizer; adhesion promoter; filler; antifoam; leveling agent; surface conditioning agent; antioxidants such as phenolic antioxidants, phosphite antioxidants and thioether antioxidants; UV absorbers; dispersing aid; anti-aggregation agents; catalyst; effect promoter; crosslinking agent; Conventional additives, such as a thickener, can be added.

In addition, by using another organic polymer together with the polymerizable compound having an ethylenically unsaturated bond having an acid value, properties of the cured product of the photosensitive composition and the colored photosensitive composition of the present invention can be improved. Examples of the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene-(meth) acrylic acid copolymer, (meth) acrylic acid-methyl Methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, poly Acrylamide, saturated polyester, phenol resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, etc. are mentioned, Among these, polystyrene, (meth)acrylic acid-methyl methacrylate copolymer, and epoxy resin are mentioned. desirable.

A chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound, etc. can be used together with the photosensitive composition and colored photosensitive composition of this invention.

As the chain transfer agent and the sensitizer, a compound containing a sulfur atom 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-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzoimidazole, 2-mercapto-3-pyridinol, 2 - Mercapto compounds such as mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropanetris (3-mercaptopropionate), and pentaerythritol tetrakis (3-mercaptopropionate), and the mercapto compound Disulfide compounds obtained by oxidation, iodine acetic acid, iodopropionic acid, 2-iodethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid, etc. alkyl iodide compounds, trimethylolpropanetris(3-mercaptoisobutyrate), butanediol Bis(3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylol Propane tristhioglycolate, butanediolbisthiopropionate, trimethylolpropane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakistioglycolate, tris Aliphatic polyfunctional thiol compounds, such as hydroxyethyl tristhiopropionate, following compound No. C1, trimercaptopropionate tris(2-hydroxyethyl) isocyanurate, Showa Denko company make Karenz MT BD1, PE1 , NR1, and the like.

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

As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used, and among them, KBE-9007, KBM-502, KBE-403, etc., having an isocyanate group, a methacryloyl group, and an epoxy group A silane coupling agent is suitably used.

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

The photosensitive composition and colored photosensitive composition of the present invention can be prepared by using known means such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing and immersion, such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic. It can be applied on a support such as In addition, once coated on a support such as a film, it may be transferred onto another support, and the application method is not limited.

Moreover, as a light source of the actinic light used when hardening the photosensitive composition and colored photosensitive composition of this invention, what emits light with a wavelength of 300-450 nm can be used, For example, ultra-high pressure mercury, a mercury vapor arc, a carbon arc , a xenon arc, etc. can be used.

In addition, by using laser light as the exposure light source, the laser direct drawing method, which directly forms an image from digital information such as a computer without using a mask, can improve not only productivity but also resolution and positional accuracy. Therefore, it is useful, and as the laser beam, light having a wavelength of 340 to 430 nm is suitably used. Argon ion laser, helium neon laser, YAG laser, and semiconductor laser, etc. emit light in the visible to infrared region. is also used In the case of using these lasers, a sensitizing dye that absorbs the above-mentioned region from visible to infrared is added.

The photosensitive composition and coloring photosensitive composition of this invention can also be patterned through the double patterning process of dividing into two times and patterning using two photosensitive compositions or coloring photosensitive composition.

The method of curing the photosensitive composition or the colored photosensitive composition of the present invention is a method for curing the photosensitive composition or the colored photosensitive composition using a known method such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing and immersion, such as soda glass, quartz glass, a semiconductor substrate, It includes a step of forming a coating film by applying it on a support such as metal, paper, plastic, and the like, and a step of curing the coating film by exposing the active light to light.

The photosensitive composition and colored photosensitive composition (or cured product thereof) of the present invention can be used for photocurable paints or varnishes, adhesives such as photocurable adhesives, printed circuit boards, or color TVs, PC monitors, portable information terminals, digital cameras, etc. color filter in liquid crystal display panel, color filter of CCD image sensor, photo spacer, black column spacer, electrode material for plasma display panel, touch panel, touch sensor, powder coating, printing ink, printing plate, dental composition, stereolithography Resins, gel coats, photoresists for electronics, electroplating resists, etching resists, both liquid and dry films, solder resists, for manufacturing color filters for various display applications or for plasma display panels, electroluminescent displays, and LCDs Resists for forming structures in the manufacturing process, compositions for encapsulating electrical and electronic components, solder resists, magnetic recording materials, micromechanical components, waveguides, optical switches, plating masks, etching masks, Color test system, glass fiber cable coating, stencil for screen printing, material for manufacturing three-dimensional objects by stereolithography, material for holographic recording, image recording material, microelectronic circuit, decolorizing material, decolorizing material for image recording material, micro Discoloration materials for image recording materials using capsules, photoresist materials for printed wiring boards, photoresist materials for UV and visible laser direct imaging systems, photoresist materials for dielectric layer formation in successive lamination of printed circuit boards, 3D It can be used for various uses, such as a photoresist material for mounting or a protective film, and there is no restriction|limiting in particular in the use.

The photosensitive composition of the present invention can be used as a transparent structure by curing. As a transparent structure, For example, the casting material called a photo spacer (PS) and a column spacer (CS); (nano) fine patterns of imprints; The inkjet receiving layer used for manufacture of a large-size advertising signboard, etc., and the manufacture of electronic devices, such as the printing of color filters for liquid crystal displays, and an alignment film, etc. are mentioned. The transparent structure of this invention is used suitably for a display device.

The photosensitive composition of the present invention can be used for a transparent conductive film, a reflective film, a polarizing plate, a protective film, etc., and each desired layer is sequentially applied to a transparent substrate, irradiated with actinic light through a mask having a predetermined pattern shape, and the film after exposure It can be used as a transparent laminate laminated|stacked by developing with a developing solution and heating the film after image development. Examples of the transparent laminate include a transparent substrate in which a transparent thin film layer and a metal thin film layer made of a complex oxide of indium oxide and cerium oxide are alternated. The photosensitive composition of this invention which contains the compound which has a substituent represented by general formula (I) in each of the above-mentioned layers as a latent additive may be used, and the said photosensitive composition may be used for either layer. In addition, the transparent laminate is suitably used for a display device.

The coloring photosensitive composition of this invention is used for the purpose of forming the pixel of a color filter, and is useful especially as a photosensitive composition for forming the color filter for display devices for image display apparatuses, such as a liquid crystal display panel.

The color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition of the present invention on a substrate, (2) a step of irradiating the coating film with actinic light through a mask having a predetermined pattern shape, (3) ) It is formed preferably by the process of developing the coating film after exposure with a developing solution, and (4) the process of heating the said coating film after development. Moreover, the coloring photosensitive composition of this invention is useful also as a coloring photosensitive composition of the inkjet system without a developing process.

As the mask, a multi-gradation mask such as a halftone mask or a gray scale mask can also be used.

Next, the novel compound of the present invention will be described. The novel compound of the present invention is represented by any one of the following structures.

Although the manufacturing method of the novel compound of this invention is not specifically limited, For example, Unexamined-Japanese-Patent No. 57-111375, Unexamined-Japanese-Patent No. 3-173843, Unexamined-Japanese-Patent No. 6-128195, Unexamined-Japanese-Patent No. Hei 7, for example. It can be obtained by reacting a phenol-based compound prepared by the methods described in -206771, Japanese Unexamined Patent Publication No. Hei 7-252191, and Japanese Unexamined Patent Publication No. 2004-501128, with an allyl halide compound or the like.

The novel compound of the present invention can be used as a latent antioxidant, a latent ultraviolet absorber, a dissolution modifier, and the like.

Example

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples and the like.

[Example 1-1] Synthesis of compound No. 1

Potassium carbonate (2 equivalents per one phenol group) was added to a dimethylacetamide solution of 1 equivalent of the phenol compound of Compound No. 1' (3 times the theoretical amount), followed by stirring at room temperature for 30 minutes. Allyl bromide (1.5 equivalents per one phenol group) was added, and the mixture was stirred at 60° C. for 5 hours. After adding ethyl acetate, washing with a 1% hydrochloric acid solution, oil-water separation was performed, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and crystallization was performed. The obtained solid was dried under reduced pressure at 60°C for 3 hours to obtain the target product. ^{It was confirmed by 1} H-NMR and IR that the obtained solid was the target product. A result is shown to [Table 1] - [Table 2].

[Examples 1-2 to 1-6] Synthesis of compounds No. 2 to 6

In Example 1-1, in the same manner as in Example 1-1, except that the phenolic compounds of the following compounds No.2' to 6' were used instead of the phenolic compounds of the following compound No.1', the target compound No.2 ~6 was synthesized. ^{It was confirmed by 1} H-NMR and IR that the obtained solid was the target product. A result is shown to [Table 1] - [Table 2].

[Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-3] Preparation of photosensitive compositions No.1 to No.2 and comparative photosensitive compositions No.1 to No.3

SPC-1000 (Showa Denko Co., Ltd., PGMEA solution with a solid content of 29%) 50.0 g, Aronix M-450 (Toagosei Co., Ltd.) 11.6 g, NCI-930 (ADEKA Co., Ltd.) 0.3 g, PGMEA 34.7 g, FZ2122 (Toray Dow Corning Co., Ltd., PGMEA solution with a solid content of 1%) 2.9 g and 0.81 g of the compound described in Table 3 were mixed, stirred until insoluble matter disappeared, and photosensitive compositions No. 1 to No. 2 and comparative photosensitivity Compositions No. 1 to No. 3 were obtained.

[Evaluation Example 1-1 and Comparative Evaluation Example 1-1] Outgas evaluation

5 mg of each of compound No. 1, compound No. 2 and comparative compound No. 2 were weighed and put in, and the temperature was raised from room temperature to 230 ° C (20 ° C./min.) with a thermal mass measurement device, and then maintained at 230 ° C. for 30 minutes. The weight loss rate at one time point was measured and it was set as outgas evaluation of photosensitive composition No.1-No.2 and comparative photosensitive composition No.2. It shows that there are few outgass, so that a weight loss is small. A result is shown in [Table 4].

From the above results, it is clear that the compound according to the present invention has less outgas, and the photosensitive composition of the present invention containing the compound according to the present invention has less outgas.

[Evaluation Example 2-1 and Comparative Evaluation Examples 2-1 to 2-2] Solvent resistance evaluation

The photosensitive composition No. 1 obtained in Example 2-1 and Comparative Photosensitive composition No. 1 and No. 3 obtained in Comparative Examples 2-1 and 2-3 were coated on a glass substrate under the conditions of 410 rpm × 7 seconds, respectively, and hot The plate was dried (90° C.×90 seconds). The obtained coating film was exposed (40 mJ/cm<2>) with an ultra-high pressure mercury lamp. The coating film after exposure was baked under the conditions of 230 degreeC x 30 minutes. After measuring the film thickness of the obtained coating film, it was made to immerse in PGMEA, cyclohexanone, N-methylpyrrolidone, N-ethylpyrrolidone at room temperature for 30 minutes, and the film thickness after immersion was measured. It evaluated that the solvent resistance was so high that the film thickness ratio (film thickness after immersion x 100/film thickness before immersion) before and behind immersion was close to 100 %.

From [Table 5], compared with the cured product of Comparative Photosensitive Composition No. 3 containing no antioxidant, the cured product of Comparative Photosensitive Composition No. 1 containing the conventional phenolic antioxidant has lowered solvent resistance, It is clear that the photosensitive composition No. 1 using the compound according to the present application as a latent additive maintains the same solvent resistance as the case where the antioxidant is not contained.

From the above result, it is clear that the photosensitive composition which used the compound of this invention as a latent additive has little outgas, and that the hardened|cured material is excellent in solvent resistance.

ADVANTAGE OF THE INVENTION According to this invention, the photosensitive composition with little outgas and high solvent resistance of hardened|cured material can be provided using the compound which is inert at normal temperature and is activated by heating to a predetermined temperature and expresses a function as an antioxidant or a ultraviolet absorber.

Claims (11)

A photosensitive composition containing a compound represented by the following general formula (IA).

(wherein n represents an integer of 2 to 6,
X ¹ represents a divalent to hexavalent bonding group represented by the following general formulas (1) to (5),
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 a substituent which may have a substituent An aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms which may have a substituent, a heterocyclic group or a trialkylsilyl group having 2 to 20 carbon atoms which may have a substituent indicate,
The ^{methylene group in the alkyl group or arylalkyl group represented by R 1} and R ² is -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S- CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR'-, A group selected from -SS- or -SO ₂ - may be substituted with a group in which oxygen atoms are not adjacent to each other, R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
j represents a number from 1 to 3.)

(In the general formula (1), Y ¹ is a single bond, -CR ⁵ R ⁶ -, -NR ⁷ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an aromatic hydrocarbon having 6 to 35 carbon atoms. a group or a heterocyclic ring-containing group having 2 to 35 carbon atoms, or any substituent represented by the following (1-1) to (1-3);
The aliphatic hydrocarbon group is, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or oxygen atoms are not adjacent to each other and these It may be substituted with a combined bonding group,
Z ¹ and Z ² are each independently a direct bond, -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -SS-, -SO-, -NR ⁷ - or -PR ⁷ -,
R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic hydrocarbon having 6 to 35 carbon atoms which may have a substituent Represents a heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a group or a substituent,
* means to combine with an adjacent group in the * part.)

(In the formula, R ⁸ represents a hydrogen atom or a optionally substituted phenyl group or a cycloalkyl group having 3 to 10 carbon atoms,
R ⁹ 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 have a substituent In some cases,
f is an integer from 0 to 5,
* means to combine with an adjacent group in the * part.)

(* means combining with an adjacent group in the * part.)

(Wherein, R ¹⁰ and R ¹¹ are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and a substituent An aryloxy group having 6 to 20 carbon atoms which may have a substituent, an arylthio group having 6 to 20 carbon atoms which may have a substituent, and an arylalkyl group having 6 to 20 carbon atoms which may have a substituent represents a nyl group, an arylalkyl group having 7 to 20 carbon atoms which may have a substituent, a heterocycle-containing group having 2 to 20 carbon atoms or a halogen atom which may have a substituent;
The methylene group in the alkyl group and the arylalkyl group may be substituted with an unsaturated bond, -O- or -S-,
R ¹⁰ may form a ring with adjacent R ^{10 ,}
p represents a number from 0 to 4,
q represents a number from 0 to 8,
g represents a number from 0 to 4,
h represents a number from 0 to 4,
The sum of the numbers g and h is 2-4,
* means to combine with an adjacent group in the * part.)

(In the general formula (2), Y ¹¹ represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or a heterocyclic group containing 2 to 35 carbon atoms,
Z ¹ , Z ² and Z ³ are each independently a direct bond, -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -SS-, - SO-, -NR ¹² - or -PR ¹² -,
R ¹² is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent or carbon which may have a substituent represents a heterocyclic-containing group having 2 to 35 atoms,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or oxygen atoms are mutually It may be substituted with a bonding group that is not adjacent to each other and combines them,
* means to combine with an adjacent group in the * part.)

(In the general formula (3), Y ¹² is a carbon atom, or a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic ring having 2 to 35 carbon atoms. represents the flag,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,
Z ¹ to Z ⁴ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),
* means to combine with an adjacent group in the * part.)

(In the general formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,
Z ¹ to Z ⁵ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),
* means to combine with an adjacent group in the * part.)

(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 heterocycle-containing group having 2 to 35 carbon atoms,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,
Z ¹ to Z ⁶ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),
* means to combine with an adjacent group in the * part.) A photosensitive composition containing a compound represented by the following general formula (II-1), (II-2) or (II-3).

(Wherein, R ¹ is a t-butyl group,
R ² is a hydrogen atom,
R ⁸² , R ⁸³ and R ⁸⁴ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an optionally substituted alkyl group having 1 to 40 carbon atoms, the number of carbon atoms represents an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.)

(Wherein, R ¹ is a t-butyl group,
R ² is a hydrogen atom,
r = 2 to 6, X ² is a group represented by the following general formula (1) when r = 2, a group represented by the following general formula (2) when r = 3, and the following general formula (2) when r = 4 It is a group represented by formula (3), when r=5, it is the following general formula (4), when r=6, it is the following general formula (5), R ⁹² and R ⁹³ are each independently a hydrogen atom and a halogen atom , a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or carbon It represents a heterocycle-containing group having 2 to 20 atoms.)

(In the general formula (1), Y ¹ is a single bond, -CR ⁵ R ⁶ -, -NR ⁷ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an aromatic hydrocarbon having 6 to 35 carbon atoms. a group or a heterocyclic ring-containing group having 2 to 35 carbon atoms, or any group represented by the following (1-1) to (1-3);
The aliphatic hydrocarbon group is, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or oxygen atoms are not adjacent to each other and these It may be substituted with a combined bonding group,
Z ¹ and Z ² are each independently a direct bond, -O-, -S-, >CO, -CO-O-, -O-CO-, -SO ₂ -, -SS-, -SO-, - NR ⁷ - or -PR ⁷ -,
R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic hydrocarbon having 6 to 35 carbon atoms which may have a substituent Represents a heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a group or a substituent,
* means to combine with an adjacent group in the * part.)

(In the formula, R ⁸ represents a hydrogen atom or a optionally substituted phenyl group or a cycloalkyl group having 3 to 10 carbon atoms,
R ⁹ 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 have a substituent In some cases,
f is an integer from 0 to 5,
* means to combine with an adjacent group in the * part.)

(* means combining with an adjacent group in the * part.)

(Wherein, R ¹⁰ and R ¹¹ are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and a substituent An aryloxy group having 6 to 20 carbon atoms which may have a substituent, an arylthio group having 6 to 20 carbon atoms which may have a substituent, and an arylalkyl group having 6 to 20 carbon atoms which may have a substituent represents a nyl group, an arylalkyl group having 7 to 20 carbon atoms which may have a substituent, a heterocyclic ring-containing group having 2 to 20 carbon atoms which may have a substituent, or a halogen atom;
The methylene group in the alkyl group and the arylalkyl group may be substituted with an unsaturated bond, -O- or -S-,
R ¹⁰ may form a ring with adjacent R ^{10 ,}
p represents a number from 0 to 4,
q represents a number from 0 to 8,
g represents a number from 0 to 4,
h represents a number from 0 to 4,
The sum of the numbers g and h is 2-4,
* means to combine with an adjacent group in the * part.)

(In the general formula (2), Y ¹¹ is a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a carbon atom represents a heterocycle-containing group of number 2-35,
Z ¹ , Z ² and Z ³ are each independently a direct bond, -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -SS-, - SO-, -NR ¹² _- or -PR ¹² -,
R ¹² is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent or carbon which may have a substituent represents a heterocyclic-containing group having 2 to 35 atoms,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or oxygen atoms are mutually It may be substituted with a bonding group that is not adjacent to each other and combines them,
* means to combine with an adjacent group in the * part.)

(In the general formula (3), Y ¹² is a carbon atom, or a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic ring having 2 to 35 carbon atoms. represents the flag,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,
Z ¹ to Z ⁴ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),
* means to combine with an adjacent group in the * part.)

(In the general formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,
Z ¹ to Z ⁵ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),
* means to combine with an adjacent group in the * part.)

(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 heterocycle-containing group having 2 to 35 carbon atoms,
The aliphatic hydrocarbon group is a carbon-carbon double bond, -O-, -S-, -CO-, -COO-, -OCO-, -NH-, -SO ₂ -, -CONH- or -NHCO-, or an oxygen valence In some cases, they are not adjacent to each other and are substituted with a bonding group that combines them,
Z ¹ to Z ⁶ are each independently a group in the same range as the group represented by ^{Z 1} to Z ³ in the general formula (2),
* means to combine with an adjacent group in the * part.)

(Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , and R ²⁰⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, and a substituent the number is also carbon atom to which the case has 1 to 40 alkyl group, a heterocyclic ring of carbon atoms from 6 to 20 aryl group, a carbon atom number of 7-20 arylalkyl group or 2 to 20 carbon atoms of the monovalent contained, Y ¹ , Z ¹ and Z ² are the same as in General Formula (1).) The photosensitive composition containing the compound of the structure shown in any one of the following.

Hardened|cured material of the photosensitive composition in any one of Claims 1-3. A display device comprising at least a part of the transparent laminate or transparent structure formed using the cured product according to claim 4 . The coloring photosensitive composition formed by making the photosensitive composition in any one of Claims 1-3 further contain a coloring agent. A cured product of the colored photosensitive composition according to claim 6 . A color filter formed using the cured product according to claim 7. Claims 1 to 3, comprising a step of applying the photosensitive composition according to any one of claims 1 to 3 on a support to form a coating film, and a step of exposing the coating film to curing by exposure to actinic light. The method of hardening the photosensitive composition in any one of Claims. A method of curing the colored photosensitive composition according to claim 6, comprising a step of applying the colored photosensitive composition according to claim 6 on a support to form a coating film, and a step of exposing the coating film to curing with actinic light. A compound represented by any one of the following structures (B) to (O).