KR20180123003A - Photosensitive composition - Google Patents

Abstract

A photosensitive composition which gives a cured product having high heat resistance and high solvent resistance is provided. A photosensitive composition comprising a latent additive (A), a polymer (B) having an ethylenically unsaturated bond and a hydrophilic group in one molecule and a double bond equivalent of 200 to 1000, an acrylic monomer (C) and a photo radical polymerization initiator (D) . In the photosensitive composition, the content of the latent additive (A) is preferably 0.001 to 20% by mass. The photosensitive composition of the present invention can be cured by irradiation with active energy rays.

Description

Photosensitive composition

The present invention relates to a polymerizable composition comprising a latent additive which is inert at room temperature and activated by being heated to a predetermined temperature to function, a polymer having an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a constant double bond equivalent, an acrylic monomer and a photo radical polymerization The present invention relates to a photosensitive composition containing an initiator. Further, the present invention relates to a colored photosensitive composition capable of being polymerized by an energy ray using the composition and a color filter using the colored photosensitive composition.

In order to improve the weather resistance and heat resistance of the resin composition, there is known a method of stabilizing by adding an ultraviolet absorber or an antioxidant (Patent Document 1).

Further, in the photosensitive composition, it is known that a fine pattern is formed by keeping the double bond equivalent of the resin within a certain range, or the contrast of the cured product is improved. However, it is not known to improve the solvent resistance by keeping the double bond equivalent of the resin within a certain range (Patent Documents 2 to 5).

Since the phenol-based antioxidant has a function of trapping radicals which greatly affect the deterioration of the polymer, when the antioxidant is added to the polymerization system, it generally becomes a so-called polymerization inhibitor and causes curing inhibition Therefore, latent additives have been developed (Patent Document 6).

Japanese Patent Application Laid-Open No. 2002-097224 Japanese Laid-Open Patent Publication No. 2009-134078 Japanese Laid-Open Patent Publication No. 2013-037272 U.S. Patent Application Publication No. 2015/254210 Japanese Patent Publication No. 5460179 U.S. Patent Application Publication No. 2015/291772

Accordingly, an object of the present invention is to provide a latent additive which is inert at room temperature and is activated by heating at a predetermined temperature to exhibit a function, a polymer having an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a constant double bond equivalent, And to provide a photosensitive composition containing a radical polymerization initiator.

As a result of intensive investigations, the present inventors have found that, as a result of intensive studies, the present inventors have found that a composition comprising a latent additive which is inert at room temperature and which is activated by heating to a predetermined temperature to exhibit a function, a polymer having a certain double bond equivalent with an ethylenically unsaturated bond and a hydrophilic group in one molecule, The present inventors have found that a cured product of a photosensitive composition containing a monomer and a photo radical polymerization initiator has high heat resistance and solvent resistance and is suitable for a color filter for an image display apparatus such as a liquid crystal display panel.

The present invention provides a latent additive (A) (hereinafter also referred to as a latent additive (A)) that is inert at room temperature and is activated by heating at a predetermined temperature to exhibit a function, an ethylenically unsaturated (B) (hereinafter, also referred to as a polymer (B)), an acrylic monomer (C) and a photoradical polymerization initiator (D) having a bonding and hydrophilic group in one molecule and having a double bond equivalent of 200 to 1000 To provide a composition.

Hereinafter, the present invention will be described in detail based on preferred embodiments.

The photosensitive composition of the present invention comprises a polymer (B) having a latent additive (A), an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a double bond equivalent of 200 to 1000, an acrylic monomer (C) and a photo radical polymerization initiator D). Hereinafter, each component will be described in order.

≪ Latent additive (A) >

The latent additive (A) used in the photosensitive composition of the present invention is inert at room temperature or in the prebake step, and is heated at 100 to 250 ° C or heated at 80 to 200 ° C in the presence of an acid / So that it becomes active. The activity of the latent additive (A) means that the additive (A) has reactivity to the radical, and the inertness means that the additive (A) does not react with the radical or has extremely low reactivity. In the photosensitive composition of the present invention, the latent additive (A) is preferably one having a skeleton represented by the following general formula (I) since it is easy to synthesize and has high heat resistance.

(Wherein Ring A ¹ represents a 5-membered or 6-membered hydrocarbon ring or a heterocyclic ring or condensed ring,

R ⁶¹ independently represents 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, an alkyl group having 6 to 20 carbon atoms An arylalkyl group having 7 to 20 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 ⁶² each independently represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, A heterocyclic ring-containing group or a trialkylsilyl group,

The methylene group in the alkyl group or arylalkyl group represented by R ⁶¹ and R ^{62 may} be a carbon-carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO- -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, , -NH-CO-O-, -NR'-, -SS-, or -SO ₂ - may be substituted with groups in which oxygen atoms are not adjacent to each other, and R 'is a hydrogen atom or a carbon atom An alkyl group having a number of 1 to 8,

A plurality of R < ⁶¹ > may be bonded to each other to form a benzene ring or a naphthalene ring,

d represents an integer of 0 to 4,

k represents an integer of 1 to 5, the sum of d and k is smaller than the number of substituents that the ring A ¹ can take,

* Means combining with adjacent groups in the * part.)

Among those having a skeleton represented by the above general formula (I), those represented by the following general formula (I-A) are particularly preferable because of high heat resistance.

(Wherein ring A ¹ , R ⁶¹ , R ⁶² , d and k are the same as in formula (I)

m represents an integer of 1 to 10,

And X < ¹ > represents an organic group of m.

In the present specification, the heterocyclic ring-containing group having 2 to 20 carbon atoms means a group containing at least one heterocyclic ring and having 2 to 20 carbon atoms throughout the group. Similarly, the heterocyclic ring-containing group having 2 to 10 carbon atoms described below means a group containing at least one heterocyclic ring and having 2 to 10 carbon atoms in the whole group. The heterocyclic ring-containing group having 2 to 35 carbon atoms described later means a group containing at least one heterocyclic ring and having 2 to 35 carbon atoms in the whole group. When the heterocyclic ring in the group containing these heterocyclic rings has a substituent, the number of carbon atoms in the whole group may exceed the upper limit value of each group. When the heterocyclic ring in the group containing a heterocyclic ring has a substituent, examples of the substituent include those exemplified as substituents which may be substituted for a group represented by X ¹ described below.

Examples of the 5-membered ring hydrocarbon ring represented by A ¹ in the general formula (I) include cyclopentadiene, and examples of the 5-membered heterocyclic ring include furan, thiophene, pyrrole, pyrrolidine, pyrazolidine, Isoxazole, thiazole, isothiazole, isothiazolidine and the like. Examples of the 6-membered ring hydrocarbon ring include benzene, Examples of the 6-membered heterocyclic ring include piperidine, piperazine, morpholine, thiomorpholine, pyridine, pyrazine, pyrimidine, pyridazine and triazine. These rings may be condensed or substituted with other rings Examples of the condensed rings include quinoline, isoquinoline, indole, julolidine, benzoxazole, benzotriazole, azulene, naphthalene, anthracene, fluorene, perylene, .

Examples of the halogen atom represented by R ⁶¹ in the above general formula (I) include fluorine, chlorine, bromine and iodine. (In the following description, all the halogen atoms are the same as described above.)

Examples of the alkyl group having 1 to 40 carbon atoms represented by R ⁶¹ in the general formula (I) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, Heptyl, iso-heptyl, tert-heptyl, 1-octyl, 2-heptyl, iso-octyl, tert-octyl, adamantyl and the like,

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 ring having 2 to 20 carbon atoms represented by R ⁶¹ in the general formula (I) As the substituent for substituting the containing group, an ethylenic unsaturated group such as vinyl, allyl, acryl or methacryl; Halogen atoms such as fluorine, chlorine, bromine and iodine; Wherein R is selected from the group consisting of acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, Acyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, Acyloxy groups such as acetyloxy and benzoyloxy; Amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, Wherein the alkyl moiety is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n- N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, N, N-dimethylaminosulfonylamino, N, N-dimethylaminosulfonylamino, N, N-dimethylaminocarbonylamino, N-methylmethoxycarbonylamino, phenoxycarbonylamino, A substituted amino group such as amino; A carboxyl group, a sulfonyl group, a sulfone group, a sulfonyl group, a carboxyl group, a cyano group, a sulfo group, a hydroxyl group, a nitro group, a mercapto group, an imide group, a carbamoyl group, Acid, and phosphoric acid.

Examples of the aryl group having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the general formula (I) include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2- Methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6 Dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6- Tert-butylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, 2,4-dicumylphenyl, , 1'-biphenyl) -4-yl, 2,4,5-trimethylphenyl, and ferrocenyl.

Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the general formula (I) include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, Phenyl-propyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like.

Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the general formula (I) include a pyridine ring, a pyrimidine ring, a pyridazin ring, a piperidine ring, a pyran ring, a pyrazoline ring, A thiazoline ring, a thiazoline ring, a benzothiazoline ring, a thiazoline ring, a thiazoline ring, a thiazoline ring, a thiazoline ring, a thiazolidine ring, A group obtained by combining a methylene chain with a heterocyclic ring such as an octane ring, 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 .

The alkyl group having 1 to 20 carbon atoms represented by R ⁶² in the general formula (I) includes those satisfying the predetermined number of carbon atoms in the alkyl group represented by R ⁶¹ .

Examples of the alkenyl group having 2 to 20 carbon atoms represented by R ⁶² in the general formula (I) include vinyl, 1-methylethen-1-yl, propen-1-yl, Butene-2-yl, 2-methylpropene-3-yl, 1,1-dimethylethen-2-yl, 1,1-dimethylpropene- Butene, isobutyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl , Eicosane, tricosene, and the like.

Examples of the trialkylsilyl group represented by R ⁶² in the general formula (I) include an alkyl group having 1 to 6 carbon atoms such as trimethylsilane, triethylsilane, and ethyldimethylsilane (the three alkyl groups may be the same or different) Silyl groups.

The alkyl group having 1 to 8 carbon atoms represented by R 'in the above general formula (I) includes those satisfying the predetermined number of carbon atoms in the alkyl group represented by R ⁶¹ .

In the general formula (I), R ⁶¹ is preferably a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group having 6 to 12 carbon atoms since it is easy to synthesize.

In the general formula (I), it is preferable that R ⁶² is bonded to -CO-O- at the terminal of the oxygen atom side of the alkyl group having 1 to 8 carbon atoms since it functions efficiently as a latent additive.

In the general formula (IA), X ¹ represents an organic group having a valence of m and specifically includes a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following formula (Ia) ,>C═O,> NR ⁶³ , -OR ⁶³ , -SR ⁶³ , -NR ⁶³ R ⁶⁴ , or an aliphatic hydrocarbon group having 1 to 120 carbon atoms and having a valence of the same number as m, which may have a substituent, An aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and having the same number of m as the number of carbon atoms optionally having a substituent, a heterocyclic ring having 2 to 35 carbon atoms having a valence of the same number as m, R ⁶³ and R ^{64 each} represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 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 group having a substituent A methylene group of the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group and the heterocyclic ring-containing group is a carbon-carbon double bond, -O-, -S-, -CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O -CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NH-CO-O-, -NR '-, - SS-, -SO 2 - or a nitrogen atom , And R 'represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

Provided that when X ¹ is a nitrogen atom, a phosphorus atom or a group represented by the following formula (Ia) or (Ib), m is 3 and X ¹ is an oxygen atom or a sulfur atom,> C═O, In the case of -CO-NH- or > NR ⁶³ , m is 2, and when X ¹ is -OR ⁶³ , -SR ⁶³ or -NR ⁶³ R ⁶⁴ , m is 1 and X ¹ is taken together with A ¹ to form a ring In some cases.

(* Means combining with adjacent groups in the * part.)

The latent additive represented by the general formula (IA) has a structure in which m specific groups are bonded to a specific atom or group of m, represented by X ¹ . These m groups are the same or different from each other. The value of m is 1 to 10, preferably 2 to 6, since it is easy to synthesize.

Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms and having the same number of moles as the group represented by X ¹ in the general formula (IA) include monovalent aliphatic hydrocarbon groups such as methyl, ethyl, propyl, isopropyl, But are not limited to, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tertiary amyl, cyclopentyl, hexyl, , Heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isonyl and decyl; But are not limited to, methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert -butyloxy, isobutyloxy, amyloxy, isoamyloxy, tertiary amyloxy, hexyloxy, Alkoxy groups such as heptyloxy, isoheptyloxy, heptyloxy, n-octyloxy, isooctyloxy, tert-octyloxy, 2-ethylhexyloxy, nonyloxy and decyloxy; Examples of the alkylthio include methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, tertiary amylthio, hexylthio, cyclohexylthio, heptyl An alkylthio group such as thio, isoheptylthio, tert-pentylthio, n-octylthio, isooctylthio, tert-octylthio, or 2-ethylhexylthio; Propyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutyl, 3-pentenyl, Alkenyl groups such as 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosyl, and tricosenyl, and groups substituted by substituents .

Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms and having the same number of moles as the group represented by X ¹ in the general formula (IA) include divalent aliphatic hydrocarbon groups such as methylene, ethylene, propylene, butylene, Alkylene; The methylene chain of the alkylene being substituted with -O-, -S-, -CO-O-, -O-CO-; Diol residues such as ethanediol, propanediol, butanediol, pentanediol, and hexanediol; And residues of dithiol such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol, and hexanedithiol, and groups in which these groups are substituted by substituents which will be described later.

Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms and having the same number of moieties as m represented by X ¹ in the general formula (IA) include trivalent aliphatic hydrocarbon groups such as propylidene, 1,1,3- Alkylidines such as butylidene and the like, and groups in which these groups are substituted by substituents which will be described later.

The formula (IA) as have a substituent having a valence of m and equal numbers represented by X ¹ is also a hydrocarbon group containing an aromatic ring of carbon atoms 6-35 in the case that in, as valence and m is 1, benzyl, phenethyl , Arylalkyl groups such as diphenylmethyl, triphenylmethyl, styryl and cinnamyl; Aryl groups such as phenyl and naphthyl; An aryloxy group such as phenoxy, naphthyloxy and the like; Arylthio groups such as phenylthio, naphthylthio and the like, and groups in which these groups are substituted by substituents which will be described later.

As the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and having the same number of m as the number of the substituent represented by X ¹ in the general formula (IA), m is a divalent group, and phenylene, An arylene group such as tylene; 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 the substituents described below.

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and having the same number of moieties as m, which may have a substituent represented by X ¹ in the general formula (IA), include those in which m is trivalent, 3,5-trimethylene, and groups in which these groups are substituted by the substituents described below.

Examples of the heterocyclic ring-containing group having 2 to 35 carbon atoms and having a valence of the same number as m, which may have a substituent represented by X ¹ in the general formula (IA), include those in which m is 1, pyridyl, pyrimidyl , Pyridyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl , Thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon- 3-yl, 2,4-dioxoimidazolidin-3-yl, benzotriazolyl, and the like, and these groups may be substituted by substituents described below And the like.

Examples of the heterocyclic ring-containing group having 2 to 35 carbon atoms and having the same number of m as the number of the substituent represented by X ¹ in the general formula (IA) include a pyridine ring, pyrimidine ring, A group having a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, a substituted piperazine group, a piperazine ring, a piperazine ring, a triazine ring, a furan ring, a thiophene ring and an indole ring;

Examples of the heterocyclic ring-containing group having 2 to 35 carbon atoms and having a valence of the same number as m, which may have a substituent represented by X ¹ in the general formula (IA), include those in which m is trivalent, A group having a triazine ring, and a group substituted by a substituent group described later.

Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R ⁶³ and R ⁶⁴ include an aliphatic hydrocarbon group having 1 to 120 carbon atoms represented by X ¹ or an aliphatic hydrocarbon group Among the combinations of the carbon atoms, the number of carbon atoms is satisfied.

R ⁶³ and as the group is also a heterocyclic ring of carbon atoms 2 to 35 contained in the case, which has a substituent represented by R ⁶⁴ contains the aromatic ring of Fig number of carbon atoms 6-35 in the case that has a hydrocarbon group or a substituent, wherein X ¹ An aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or a heterocyclic ring-containing group having 2 to 35 carbon atoms, or a group obtained by combining these groups with the substituents described later.

An aliphatic hydrocarbon group having 1 to 120 carbon atoms represented by X ¹ , an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and a heterocyclic ring-containing group having 2 to 35 carbon atoms, and R ⁶³ and Examples of the substituent which may be substituted for an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a heterocyclic ring-containing group having 2 to 35 carbon atoms represented by R ⁶ include vinyl, allyl , Ethylenic unsaturated groups such as acrylic and methacrylic groups; Halogen atoms such as fluorine, chlorine, bromine and iodine; Examples of the substituents are acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, An acyl group such as saloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl or carbamoyl; Acyloxy groups such as acetyloxy and benzoyloxy; Amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, Wherein the alkyl moiety is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n- N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, N, N-dimethylaminosulfonylamino, N, N-dimethylaminosulfonylamino, N, N-dimethylaminocarbonylamino, N-methylmethoxycarbonylamino, phenoxycarbonylamino, A substituted amino group such as amino; A carboxyl group, a sulfonyl group, a sulfone group, a sulfonyl group, a carboxyl group, a cyano group, a sulfo group, a hydroxyl group, a nitro group, a mercapto group, an imide group, a carbamoyl group, Acid group, and phosphoric acid group, and these groups may be further substituted. In addition, the carboxyl group and the sulfo group may form a salt.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R 'in the formula (IA) include those satisfying the predetermined number of carbon atoms in the alkyl group represented by R ⁶¹ described above.

When m is 2 in the formula (IA), X ¹ may be represented by the following general formula (1).

(In the general formula (1), Y ¹⁰ represents a single bond, -CR ⁶⁵ R ⁶⁶ -, -NR ⁶⁷ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms Or a heterocyclic ring-containing group having 2 to 35 carbon atoms, or any one substituent shown by the following (1-1) to (1-3)

The carbon atom adjacent to the aliphatic hydrocarbon group may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, or -NH-, or when the oxygen atom is not adjacent and is terminated by a bonding group combining these In addition,

The carbon atom at the terminal of the aliphatic hydrocarbon group may be substituted with -O-, -S-, -CO-, -COO-, -OCO- or -NH-,

The aliphatic hydrocarbon group may be substituted with a hydroxyl group, a halogen atom, a cyano group, a nitro group, a carboxyl group or an alkoxy group,

Z ¹ and Z ² are each independently a direct bond, -O-, -S-,> CO, -CO-O-, -O-CO-, -SO ₂ -, -SS-, NR ⁶⁷ or > PR ⁶⁷ ,

R ⁶⁵ , R ⁶⁶ and R ⁶⁷ each independently represents a hydrogen atom, a hydroxyl group, an aliphatic hydrocarbon group of 1 to 35 carbon atoms which may have a substituent, an aliphatic hydrocarbon group of 6 to 35 carbon atoms An aromatic hydrocarbon group or a heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a substituent,

* Means combining with the * adjacent to the * part.)

(Wherein R ⁷¹ represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group of 3 to 10 carbon atoms,

R ⁷² represents an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, or a halogen atom,

The alkyl group, alkoxy group and alkenyl group may have a substituent,

f is an integer from 0 to 5, and * means to combine with adjacent groups in the * portion.)

(* Means combining with adjacent groups in the * part.)

( ^Wherein R ⁷³ and R ⁷⁴ each independently represent 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, An aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, which may have a substituent, an aryloxy group having 6 to 20 carbon atoms, which may have a substituent, 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 ⁷³ may form a ring adjacent to R ⁷³ ,

p represents a number of 0 to 4,

q represents a number of 0 to 8, g represents a number of 0 to 4,

h represents a number of 0 to 4,

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

* Means combining with adjacent groups in the * part.)

In the general formula (IA), when m is 3, X ¹ may be represented by the following general formula (2).

(In the general formula (2), Y ¹¹ represents an aliphatic hydrocarbon group having 3 to 35 carbon atoms, a trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, An aromatic hydrocarbon group or a heterocyclic ring-containing group having 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 ⁶⁸ or > PR ⁶⁸ ,

R ⁶⁸ is a hydrogen atom, an aliphatic hydrocarbon group of 1 to 35 carbon atoms which may have a substituent, an aromatic hydrocarbon group of 6 to 35 carbon atoms which may have a substituent, or a carbon which may have a substituent A heterocyclic ring-containing group having 2 to 35 atoms,

The carbon atom adjacent to the aliphatic hydrocarbon group may be interrupted by a carbon-carbon double bond, -O-, -CO-, -O-CO-, -CO-O- or -SO ₂ -

The carbon atom at the terminal of the aliphatic hydrocarbon group may be substituted with a carbon-carbon double bond, -O-, -CO-, -O-CO-, -CO-O- or -SO ₂ -.

When m is 4 in the general formula (IA), X ¹ may be represented by the following general formula (3).

(3), Y ¹² represents a single bond, a carbon atom, or an aliphatic hydrocarbon group having 1 to 35 carbon atoms or an aromatic hydrocarbon group having 4 to 6 carbon atoms, or a tetravalent carbon atom number Containing heterocyclic group having 2 to 35 carbon atoms,

The carbon atom adjacent to the aliphatic hydrocarbon group may be interrupted by -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,

The carbon atom at the terminal of the aliphatic hydrocarbon group may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,

Z ¹ to Z ⁴ each independently represent a group in the same range as the group represented by Z ¹ to Z ³ in the general formula (2)).

In the formula (IA), when m is 5, X ¹ may be represented by the following general formula (4).

(4), Y ¹³ represents an aliphatic hydrocarbon group having a single bond, a pentavalent number of 2 to 35 carbon atoms, an aromatic hydrocarbon group having 5 to 20 carbon atoms, or an aromatic hydrocarbon group having 5 to 20 carbon atoms A heterocyclic-containing group,

The carbon atom adjacent to the aliphatic hydrocarbon group may be interrupted by -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,

The carbon atom at the terminal of the aliphatic hydrocarbon group may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,

Z ¹ to Z ⁵ each independently represent a group in the same range as the group represented by Z ¹ to Z ³ in the general formula (2)).

In the formula (IA), when m is 6, X ¹ may be represented by the following general formula (5).

(In the general formula (5), Y ¹⁴ represents an aliphatic hydrocarbon group of a single bond, hexavalent alcohols of 2 to 35 carbon atoms, an aromatic hydrocarbon group of 6 to 35 carbon atoms, or an aromatic hydrocarbon group of 6 to 35 carbon atoms A heterocyclic-containing group,

The carbon atom adjacent to the aliphatic hydrocarbon group may be interrupted by -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,

The carbon atom at the terminal of the aliphatic hydrocarbon group may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,

Z ¹ to Z ⁶ each independently represent a group in the same range as the group represented by Z ¹ to Z ³ in the general formula (2)).

The general formula (1) As R ^65, an aliphatic hydrocarbon group of even number of carbon atoms 1-35 in the case that has a substituent represented by R ⁶⁶ and R ⁶⁷ in, m represented by X ¹ in the general formula (IA) Aliphatic hydrocarbon groups of 1 to 120 carbon atoms exemplified as monovalent organic groups and monovalent groups represented by the substituent of these groups represented by X ¹ in formula (IA) one of a and of the group which is substituted by one exemplified as the substituent, and the like to meet the predetermined number of the carbon atoms, illustrated by way of m-valent organic group represented by X ¹ in these groups, or the general formula (IA) 2 A divalent group in which an aliphatic hydrocarbon group having 1 to 30 carbon atoms is substituted with Z ¹ and Z ² can be exemplified as a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y ¹⁰ .

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, which may have a substituent represented by R ⁶⁵ , R ⁶⁶ and R ⁶⁷ , include those exemplified as the organic groups represented by X ¹ in the general formula (IA) A monovalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and groups substituted by those exemplified as the substituent of the group representing the organic group represented by m ¹ represented by X ¹ in the formula (IA) And the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms exemplified as the organic group of these groups or the group represented by X ¹ in the general formula (IA) is a divalent group substituted with Z ¹ and Z ² , And an aromatic ring-containing hydrocarbon group having 6 to 35 divalent carbon atoms represented by Y < ¹⁰ >.

R ^65, R ^66, and if you have a substituent represented by R ⁶⁷ as the group is also a heterocyclic ring of carbon atoms 2 to 35 contained in, a first exemplified as the m-valent organic group represented by X ¹ in the general formula (IA) group of the monovalent heterocyclic ring of carbon atoms 2 to 35 containing group, and these can be exemplified by a group such as optionally substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula (IA), These divalent groups having 2 to 35 carbon atoms and having an aromatic ring-containing hydrocarbon group substituted with Z ¹ and Z ² , which are exemplified as an organic group of these groups or m ¹ represented by X ¹ in the general formula (IA) carbon atoms, a divalent shown by ¹⁰ can be given as containing heterocyclic group of 2 to 35.

Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R ⁷¹ in the substituent represented by the above (1-1) include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, and the like.

As the alkyl group having 1 to 10 carbon atoms represented by R ⁷² in the substituent represented by the above-mentioned (1-1), it is preferable that the number of carbon atoms in the group exemplified as the alkyl group having 1 to 40 carbon atoms represented by R ⁶¹ is And the like.

Examples of the alkoxy group having 1 to 10 carbon atoms represented by R ⁷² in the substituent represented by the above (1-1) include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, Isobutyloxy, isobutyloxy, amyloxy, isoamyloxy, tertiary amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, 3-octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy and the like.

The substituent of the phenyl group, the alkyl group, the alkoxy group and the alkenyl group in the substituent represented by the above-mentioned (1-1) is exemplified by those exemplified as the substituent of the group denoting the organic group having m value represented by X ¹ in the general formula (IA) same.

Examples of the alkyl group having 1 to 10 carbon atoms which may have a substituent represented by R ⁷³ and R ⁷⁴ in the group represented by the above formula (1-3) include those exemplified as the alkyl group having 1 to 40 carbon atoms represented by R ⁶¹ And a group which satisfies a predetermined number of carbon atoms in the period.

Examples of the aryl group having 6 to 20 carbon atoms, which may have a substituent represented by R ⁷³ and R ⁷⁴ in the group represented by (1-3), include those having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² A group exemplified as an aryl group, and the like.

Examples of the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R ⁷³ and R ⁷⁴ in the group represented by (1-3) include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3 Butylphenyloxy, 4-methylphenyloxy, 4-methylphenyloxy, 4-vinylphenyloxy, 3-isopropylphenyloxy, 4-isopropylphenyloxy, , 4-cyclohexylphenyloxy, 4-octylphenyloxy, 4- (2-ethylhexyl) phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2 Dimethylphenyloxy, 3,5-dimethylphenyloxy, 2,4-di-tert-butylphenyloxy, 2,5-di-tert-butylphenyloxy, 2,6 Butylphenyloxy, 2,4-di-tert-butylphenyloxy, 2,5-tert-amylphenyloxy, 4-cyclohexylphenyloxy, 2,4,5-trimethylphenyloxy, And the like.

Examples of the arylthio group having 6 to 20 carbon atoms, which may have a substituent represented by R ⁷³ and R ⁷⁴ in the group represented by (1-3), include an arylthio group having 6 to 20 carbon atoms, A group in which an oxygen atom of the 20th aryloxy group is substituted with a sulfur atom, and the like.

Examples of the arylalkenyl group having 6 to 20 carbon atoms which may have a substituent represented by R ⁷³ and R ⁷⁴ in the group represented by the above (1-3) include an arylalkenyl group having 6 to 20 carbon atoms, Substituted by an alkenyl group such as vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl or 2- And the like.

Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R ⁷³ and R ⁷⁴ in the group represented by (1-3) include groups exemplified as arylalkyl groups having 7 to 20 carbon atoms represented by R ⁶¹ and R ⁶² .

In the groups shown by (1-3), R ^73, and if you have a substituent represented by R ⁷⁴ as the group is also heterocycle having 2 to 20 carbon atoms contained in, the number of carbon atoms represented by R ⁶¹ and R ⁶² 2 ~ A group exemplified as a heterocyclic ring-containing group of 20, and the like.

Examples of the trivalent aliphatic hydrocarbon group represented by Y ¹¹ in the general formula (2) include a monovalent to trivalent aliphatic hydrocarbon group exemplified as an organic group represented by X ¹ in the general formula (IA) It includes groups of the aliphatic hydrocarbon group, and these will be to the meet the predetermined number of the carbon atoms of the group which is substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula (IA) Z ^1, Z < ^{2 >} and Z < ³ >.

Examples of the trivalent alicyclic hydrocarbon group represented by Y ¹¹ in the above general formula (2) include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2 Cyclohexyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclohexyl, cyclohexyl, cyclohexyl, cyclohexyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclohexyl, cyclohexyl, Bicyclo [2.1.0] pentyl, bicyclo [3.1.0] hexyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.0] Bicyclo [4.2.1] heptyl, bicyclo [3.1.1] heptyl, bicyclo [2.2.1] heptyl, bicyclo [5.1.0] octyl, bicyclo [4.2.0] octyl, ] 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, Tricyclodecanyl, tetracyclododecanyl, heptyl, cyclododecanyl, and the like are substituted with Z ¹ , Z ^2, and Z ³ , And the like.

Formula (2) As the hydrocarbon group containing an aromatic ring of a trivalent carbon atoms 6-35 represented by Y ¹¹ in, a 1 illustrates a m-valent organic group represented by X ¹ in the general formula (IA) ~ a trivalent aromatic ring-containing hydrocarbon group, and these groups are the groups such as optionally substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula (IA) Z ^1, Z ² and Z ³ And a substituted trivalent group.

Formula (2) The group-containing heterocyclic ring of a trivalent carbon atoms, 2 to 35 represented by Y ¹¹ in the general formula A 1 a to 3 exemplified as a m-valent organic group represented by X ¹ in (IA) Containing heterocyclic group and groups substituted by those groups represented by the substituent of the group representing the organic group of m in formula (IA) represented by X ¹ in the formula (IA) are substituted with Z ¹ , Z ² and Z ³ Trivalent group, and the like.

Further, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, which may have a substituent represented by R ⁶⁸ in the general formula (2), an aromatic hydrocarbon group having 6 to 35 carbon atoms which may have a substituent, Examples of the heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a substituent include the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group and the aromatic ring-containing hydrocarbon group exemplified in the description of R ⁶⁵ and R ⁶⁶ in the general formula (1) Containing group.

Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y ¹² in the general formula (3) include monovalent to trivalent aliphatic hydrocarbon groups exemplified as the organic groups represented by X ¹ in the general formula (IA) It includes groups of the aliphatic hydrocarbon group, and these will be to the meet the predetermined number of the carbon atoms of the group which is substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula (IA) Z ^1, Z ² , Z ³ and Z ⁴ , and the like.

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹² in the general formula (3) include monovalent to trivalent monovalent hydrocarbon groups exemplified as an organic group represented by X ¹ in the general formula (IA) aromatic ring-containing hydrocarbon group and a group such as optionally substituted by one exemplified as the substituent of the group represented those groups wherein an m-valent organic represented by X ¹ in the general formula ^{(IA) Z 1, Z 2} , Z 3 and Z ⁴ , And the like.

The general formula (3) Y ¹² carbon atoms tetravalent represents a heterocyclic ring of 2 to 35 containing group include, a monovalent to 3 exemplified as a m-valent organic group represented by X ¹ in the general formula (IA) in Containing heterocyclic group and groups in which these groups are substituted as exemplified as the substituent of the group representing the organic group of m in formula ( ¹ ) in which Z ¹ , Z ² , Z ³ and Z ⁴ , And the like.

Examples of the aliphatic hydrocarbon group having 5 to 30 carbon atoms represented by Y ¹³ in the above general formula (4) include monovalent to trivalent aliphatic hydrocarbon groups exemplified as an organic group represented by X ¹ in the general formula (IA) It includes groups of the aliphatic hydrocarbon group, and these will be to the meet the predetermined number of the carbon atoms of the group which is substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula (IA) Z ^1, Z ² , Z ³ , Z ⁴ and Z ⁵ , and the like.

Examples of the five-valent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹⁴ in the general formula (4) include monovalent hydrocarbon groups having 1 to 20 carbon atoms exemplified as an organic group represented by X ¹ in the general formula (IA) a trivalent aromatic ring-containing hydrocarbon group, and these groups are the one to the one group and the like optionally substituted exemplified as the substituent of the group represented an organic n-valent represented by X ¹ in the general formula ^{(IA) Z 1, Z 2} , Z 3, Z ⁴ and Z ⁵ , and the like.

The general formula (4) Y ¹⁴ as the pentavalent carbon atoms, a heterocyclic ring of 2 to 35 containing the group represented by, n valent indicated by X in the m represented by X ¹ in the general formula (IA) oil in Examples of the heterocyclic group having 1 to 3 hydrogen atoms and groups substituted by the groups exemplified as substituents of the groups of the group representing the organic group of m in formula (IA) represented by X ¹ in the general formula (IA) are Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , and the like.

Examples of the aliphatic hydrocarbon group having 6 to 6 carbon atoms and represented by Y ¹⁴ in the above general formula (5) include monovalent to trivalent aliphatic hydrocarbon groups exemplified as the organic groups represented by X ¹ in the general formula (IA) It includes groups of the aliphatic hydrocarbon group, and these will be to the meet the predetermined number of the carbon atoms of the group which is substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula (IA) Z ^1, Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ , and the like.

The general formula (5) Examples of the hydrocarbon group-containing aromatic ring, a 6-valent carbon atoms 6-35 represented by Y ¹⁴ in, a 1 illustrates a m-valent organic group represented by X ¹ in the general formula (IA) ~ a trivalent aromatic ring-containing hydrocarbon group, and those groups wherein the group or the like substituted by one exemplified as the substituent of the group represents an m-valent organic represented by X ¹ in the general formula ^{(IA) Z 1, Z 2} , Z 3, Z ⁴ , Z ⁵ and Z ⁶ , and the like.

The general formula (5) Y as the ^{14-containing} 6-valent carbon atoms, a heterocyclic ring of 2 to 35 represented by the groups of the general formula A 1 a to 3 exemplified as a m-valent organic group represented by X ¹ in (IA) on A substituted group represented by Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ as exemplified as the substituent of the substituted heterocyclic group having 1 to 6 carbon atoms, and the like.

In the general formula (IA), the sum of d and k is smaller than the number of substituents that the ring A ¹ can take. For example, when ring A ¹ is a six-membered aromatic ring, substituent A ¹ can take 6 and d + k? 5. Further, the ring A ¹ is the complex sun dog when the 5-membered ring, substituent (s) that can take the ring A ¹ is a 4, d + k≤3.

Specific examples of the compound represented by the formula (I-A) include those having the following structures.

Among the compounds represented by the general formula (I-A), the compounds represented by the following general formulas (II) to (IV) are preferable since they are easy to synthesize and have high heat resistance.

(Wherein ring A ² is an aliphatic, aromatic ring or heterocyclic six-membered ring, R ^81, R ^82, R ^83, R ⁸⁴ and R ⁸⁵ is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl 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, a heterocyclic ring-containing group having 2 to 20 carbon atoms, -OR ⁶² , and at least one of R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ and R ⁸⁵ is not a hydrogen atom, and R ⁶² is the same as in formula (I).

(Wherein X ² is a group represented by the above general formula (1), and R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ have a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, , An aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic ring-containing group having 2 to 20 carbon atoms, and R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ is not a hydrogen atom, R ⁶² is the same as in formula (I), and ring A ² is the same as in formula (II).

Wherein r is 2 to 6 and X ³ is a group represented by the general formula (1) when r = 2, r is a group represented by the general formula (2) when a group represented by the formula (3), r = the fifth day and the group represented by the general formula (4), a group r = time 6 days represented by the above-mentioned formula (5), r ^91, r ^92, R ⁹³ and R ^{94 each} represent 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, an aryl group having 6 to 20 carbon atoms, An arylalkyl group having 7 to 20 atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms, at least one of R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ is not a hydrogen atom, R ⁶² is a group represented by the general formula (I ), And ring A ² is the same as in formula (II).

Examples of the alicyclic, aromatic or heterocyclic ring of the 6-membered ring represented by the ring A ² in the general formula (II) include those exemplified for the explanation of A ¹ in the general formula (I).

A halogen atom represented by R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ and R ⁸⁵ in the general formula (II), an alkyl group having 1 to 40 carbon atoms which may have a substituent, an alkyl group having 6 to 20 carbon atoms Examples of the aryl group, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified for R ⁶¹ and R ⁶² in the general formula (I).

A halogen atom represented by R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ in the general formula (III), an alkyl group having 1 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms, Examples of the arylalkyl group having 7 to 20 carbon atoms and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified for R ⁶¹ and R ⁶² in the general formula (I).

A halogen atom represented by R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ in the general formula (IV), an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, Examples of the arylalkyl group having 7 to 20 carbon atoms and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified for R ⁶¹ and R ⁶² in the general formula (I).

Among the compounds represented by the general formula (II)

Preferably the ring A ² of benzene, naphthalene and the,

Of the groups represented by R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ and R ⁸⁵ , examples of the group other than the hydrogen atom include an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, An alkyl group and a heterocyclic ring-containing group having 2 to 10 carbon atoms are preferable, and it is particularly preferable that any one of R ⁸¹ to R ⁸⁵ is an alkyl group having 1 to 4 carbon atoms or a heterocyclic ring-containing group having 2 to 10 carbon atoms,

R ⁶² preferably has the following substituent group with -CO-O- interposed therebetween.

Is an alkyl group having 1 to 8 carbon atoms (particularly methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, Methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl)

An arylalkyl group having 7 to 10 carbon atoms (especially a benzyl group)

An alkenyl group having 2 to 6 carbon atoms (particularly, propen-1-yl group)

Among the compounds represented by the above general formula (III)

Preferably the ring A ² of benzene, naphthalene and the,

Of the groups represented by R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ , examples of the group other than the hydrogen atom include 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, A heterocyclic ring-containing group having 2 to 10 atoms, particularly an alkyl group having 1 to 8 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms,

R ⁶² preferably has the following substituent group with -CO-O- interposed therebetween.

Is an alkyl group having 1 to 8 carbon atoms (particularly methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, Methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl)

An arylalkyl group having 7 to 10 carbon atoms (especially a benzyl group)

An alkenyl group having 2 to 6 carbon atoms (particularly, propen-1-yl group)

In the general formula (1) representing X ¹¹ , Y ¹⁰ is preferably a sulfur atom, an aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, or a heterocyclic ring-containing group having 2 to 21 carbon atoms,

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, Is preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

Among the compounds represented by the general formula (IV)

Of the groups represented by R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , examples of the group other than the hydrogen atom include an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic ring containing 2 to 10 carbon atoms Group, in particular, any one of R ⁹¹ to R ⁹⁴ is preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic ring-containing group having 2 to 10 carbon atoms.

R ⁶² preferably has the following substituent group with -CO-O- interposed therebetween.

Is an alkyl group having 1 to 8 carbon atoms (particularly methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, Methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl)

An arylalkyl group having 7 to 10 carbon atoms (especially a benzyl group)

An alkenyl group having 2 to 6 carbon atoms (particularly, propen-1-yl group)

When r = 2 in the compound represented by the general formula (IV) and X ³ is the general formula (1), Y ¹⁰ represents a sulfur atom, an alkyl group having 1 to 20 divalent carbon atoms, An aromatic ring-containing hydrocarbon group having 6 to 25 atoms, a divalent heterocyclic ring-containing group having 2 to 21 carbon atoms, 2,4,8,10-tetraoxaspiro [5,5] undecane, particularly a divalent carbon atom An alkyl group having a number of 1 to 15, an aromatic ring-containing hydrocarbon group having 6 to 15 divalent carbon atoms, and 2,4,8,10-tetraoxaspiro [5,5] undecane,

Z ¹ and Z ² are each a direct bond, -CO-O-, -O-CO- or a divalent aliphatic hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, a divalent aliphatic hydrocarbon group of 6 to 10 carbon atoms An aromatic hydrocarbon group, particularly an aliphatic hydrocarbon group having 1 to 8 divalent carbon atoms which may have a substituent.

In the case where r = 3 in the compound represented by the general formula (IV) and X ³ is the general formula (2), Y ¹¹ is an alkyl group having 1 to 20 carbon atoms, An arylalkyl group having 7 to 12 carbon atoms, an arylalkyl group having 3 to 10 carbon atoms, a heterocyclic ring-containing group having 2 to 10 carbon atoms, particularly an alkyl group having 1 to 8 carbon atoms, An aryl group having 1 to 9 carbon atoms, or a heterocyclic ring-containing group having 1 to 6 carbon atoms,

Z ¹ , Z ² and Z ³ are each a direct bond, -CO-O-, -O-CO- or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, Preferably an aliphatic hydrocarbon group of 1 to 8 carbon atoms, more preferably an aromatic hydrocarbon group of 1 to 10 carbon atoms, particularly a divalent aliphatic hydrocarbon group of 1 to 8 carbon atoms, which may have a substituent.

In the case where r = 4 in the compound represented by the general formula (IV) and X ³ is the general formula (3), Y ¹² represents an alkyl group having 1 to 20 carbon atoms, A tetravalent arylalkyl group having 7 to 12 carbon atoms, a tetravalent heterocyclic ring-containing group having 2 to 10 carbon atoms, particularly a tetravalent alkyl group having 1 to 8 carbon atoms, an aryl group having 4 to 6 carbon atoms, An aryl group having 1 to 9 carbon atoms, or a heterocyclic ring-containing group having 1 to 6 carbon atoms,

Z ¹ to Z ^{4 each} independently represent a direct bond, -CO-O-, -O-CO- or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a divalent aliphatic hydrocarbon group having 6 to 10 carbon atoms An aromatic hydrocarbon group, particularly an aliphatic hydrocarbon group having 1 to 8 divalent carbon atoms which may have a substituent.

In the case where r = 5 in the compound represented by the general formula (IV) and X ³ is the general formula (4), Y ¹³ is an alkyl group having 1 to 20 carbon atoms, An arylalkyl group having 7 to 12 carbon atoms, an arylalkyl group having 5 to 5 carbon atoms, a heterocyclic ring-containing group having 5 to 6 carbon atoms, especially an alkyl group having 5 to 6 carbon atoms, An aryl group having 1 to 9 carbon atoms, and a heterocyclic ring-containing group having 1 to 6 carbon atoms,

Z ¹ to Z ^{5 each} represents a direct bond, -CO-O-, -O-CO-, or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a divalent aliphatic hydrocarbon group having 6 to 10 carbon atoms An aromatic hydrocarbon group, particularly an aliphatic hydrocarbon group having 1 to 8 divalent carbon atoms which may have a substituent.

When r = 6 in the compound represented by the general formula (IV) and X ³ is the general formula (5), Y ¹⁴ represents an alkyl group having 1 to 20 carbon atoms, 6 to 6 carbon atoms, An arylalkyl group having 6 to 6 carbon atoms, an arylalkyl group having 6 to 6 carbon atoms, a heterocyclic ring-containing group having 6 to 6 carbon atoms, in particular an alkyl group having 6 to 6 carbon atoms, an aryl group having 6 to 6 carbon atoms, An aryl group having 6 to 9 carbon atoms, and a heterocyclic ring-containing group having 1 to 6 carbon atoms,

Z ¹ to Z ^{6 each} independently represent a direct bond, -CO-O-, -O-CO-, or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a divalent aliphatic hydrocarbon group having 6 to 10 carbon atoms An aromatic hydrocarbon group, particularly an aliphatic hydrocarbon group having 1 to 8 divalent carbon atoms which may have a substituent.

Examples of the above-mentioned heterocyclic ring-containing group having 2 to 10 carbon atoms include heterocyclic ring-containing groups having 1 to 10 carbon atoms in the above-mentioned heterocyclic ring-containing groups having 2 to 35 carbon atoms and exemplified compounds.

In the photosensitive composition of the present invention, the content of the latent additive (A) is preferably 0.001 to 20 mass%, more preferably 0.005 to 5 mass%.

≪ Polymer (B) >

The polymer (B) used in the photosensitive composition of the present invention is not particularly limited as long as it is a polymer having an ethylenic unsaturated bond and a hydrophilic group in one molecule and a double bond equivalent of 200 to 1000, have.

Examples of the hydrophilic group possessed by the polymer (B) include a hydroxyl group, a thiol group, a carboxyl group, a sulfo group, an amino group, an amide group or a salt thereof and the hydroxyl group and the carboxyl group are preferable because the solubility of the polymer (B) Do.

The preferred functional group equivalent (the mass of the polymer containing one equivalent of the hydrophilic group) of the hydrophilic group in the polymer (B) is 50 to 10,000.

The preferred mass average molecular weight of the polymer (B) is 3000 to 50000.

Examples of the polymer (B) include (meth) acrylic acid,? -Chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, histamic acid, crotonic acid, isocrotonic acid, vinylacetic acid, allylacetic acid, cinnamic acid, sorbic acid, (Meth) acryloyloxyethyl] mono [2- (meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono Mono (meth) acrylate, hydroxyethyl (meth) acrylate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate or one carboxyl group of a polymer having a carboxyl group and a hydroxyl group Unsaturated polybasic acids such as polyfunctional (meth) acrylates having two or more (meth) acryloyl groups; Novolak type epoxy compounds such as phenol and / or cresol novolak epoxy resin, biphenyl skeleton, novolak epoxy resin having naphthalene skeleton, bisphenol A novolak type epoxy compound and dicyclopentadiene novolak type epoxy compound, polyfunctional A polyphenylmethane type epoxy resin having an epoxy group, an epoxy compound such as an epoxy compound represented by the following general formula (V), a resin obtained by reacting an unsaturated monobasic acid with an epoxy group, an epoxy resin such as an epoxy compound represented by the following general formula (V) A resin obtained by reacting an unsaturated monobasic acid with an epoxy group of a polyfunctional acrylic acid and reacting with a polybasic acid anhydride, a hydroxyl group-containing polyfunctional acrylate such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate, Acid anhydride which is a reactant of a dibasic acid anhydride such as tetrahydrophthalic anhydride. There may be mentioned the ability acrylate.

(Wherein X ⁴¹ represents 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-mentioned (1-1)

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

and n is an integer of 0 to 10.)

A unit represented by the following general formula (VI-2), a unit represented by the following general formula (VI-3), and a unit represented by the following general formula (VI-4) ) Is preferable because it has high developability and heat resistance.

Wherein R ¹ is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aryl group having 7 to 30 carbon atoms (wherein R ¹ is a hydrogen atom or a methyl group, X ⁴ is a divalent linking group, And the hydrogen atom of the alkyl group, aryl group and arylalkyl group may be substituted with a halogen atom, a hydroxyl group, a nitro group or an epoxy group, and the methylene group in the alkyl group and the arylalkyl group may be substituted with -O-, -S -, -CO-, -COO-, -OCO- or -NH-, or a combination thereof, and R ² , R ³ and R ⁴ are each independently a hydrogen atom or a methyl group. )

The divalent linking group represented by X ⁴ in the general formula (VI-2) is not particularly limited, but is preferably a structure represented by the general formula (1).

(VI-1) :( VI-2) :( VI-3) :( VI-4) = 0 to 0.65: 0.1 (VI-1) 1: 0.001 to 2: 0 to 1, and any arrangement such as random copolymerization, block copolymerization or graft copolymerization may be employed.

Among the polymers (B) having at least any one selected from the units represented by the general formulas (VI-1), (VI-2), (VI-3) and (VI-4) .

R ¹ is preferably an alkyl group having 1 to 8 carbon atoms and an arylalkyl group having 7 to 30 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms.

X ⁴ is a divalent, if the structure shown to the combiner general formula (1), Y ¹⁰ is preferably an alkylene carbon atoms, from 1 to 15 groups, and the cycloalkyl carbon atoms having an alkylene 7-15 alkylene group or It is more preferable to have a substituent having a carboxyl group. The hydrogen atom in the alkylene group may be substituted with a halogen atom, a hydroxyl group or a nitro atom, and the methylene group in the chain alkylene part in the alkylene group may be replaced by -O-, -S-, -CO-, -COO -, -OCO- or -NH- group.

Z ¹ and Z ² are preferably a direct bond.

The polymer (B) has an acid value of preferably 10 to 200 mg / KOH, more preferably 30 to 150 mg / KOH. When the acid value is less than 10 mg / KOH, the alkali developability may not be sufficiently obtained. When the acid value is more than 200 mg / KOH, there is a fear that the production of the polymer (B) becomes difficult.

Here, acid clogging is based on JIS K 0050 and JIS K 0211.

The polymer (B) has a double bond equivalent of 200 to 1000, preferably 300 to 500. If the double bond equivalent of the polymer (B) is less than 200, the preparation is difficult. If it is more than 1000, the durability is not sufficiently obtained.

The double bond equivalent is a weight average molecular weight per one double bond in the polymer (B), and can be calculated by the following formula. Double bond equivalent = (total mass of polymer (B)) / {(moles of polymer (B)) x (number of ethylenically unsaturated groups in polymer (B)

In the photosensitive composition of the present invention, the content of the polymer (B) is preferably 1 to 20% by mass, more preferably 5 to 15% by mass, in the photosensitive composition of the present invention. When the content of the polymer (B) is less than 1% by mass, resolution and durability may not be sufficiently obtained, and when it is more than 20% by mass, alkali developing property and curability may not be sufficiently obtained.

≪ Acrylic monomer (C) >

The acrylic monomer (C) used in the photosensitive composition of the present invention is not particularly limited and known ones can be used. Examples thereof include acrylic acid-2-hydroxyethyl acrylate, 2- hydroxypropyl acrylate, isobutyl acrylate, Octyl acrylate, isooctyl acrylate, isononyl acrylate, stearyl acrylate, methoxyethyl acrylate, dimethylaminoethyl acrylate, zinc acrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, methacryl 2-hydroxyethyl, 2-hydroxypropyl methacrylate, butyl methacrylate, tertiary butyl methacrylate, cyclohexyl methacrylate, trimethylolpropane trimethacrylate, dipentaerythritol pentaacrylate , Dipentaerythritol hexaacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, bisphenol A diglycidyl Ether (meth) acrylate, bisphenol F diglycidyl ether (meth) acrylate, bisphenol Z diglycidyl ether (meth) acrylate, tripropylene glycol di (meth) acrylate and the like.

Above all, a monomer having a plurality of unsaturated bonds is preferable because heat resistance can be improved.

In the photosensitive composition of the present invention, the content of the acrylic monomer (C) is preferably from 1 to 20% by mass, more preferably from 5 to 15% by mass, in the photosensitive composition of the present invention. If the content of the acrylic monomer (C) is less than 1% by mass, the curability and alkali developability may not be sufficiently obtained. If the content is more than 20% by mass, resolution and durability may not be sufficiently obtained.

≪ Photo radical polymerization initiator (D) >

The photo radical polymerization initiator (D) used in the photosensitive composition of the present invention may be any compound capable of initiating radical polymerization upon irradiation with light, and examples thereof include acetophenone compounds, benzyl compounds, A ketone-based compound such as a nonano-based compound, a thioxanthone-based compound, and an oxime-based compound.

Examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4'- 2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-on, p-dimethylaminoacetophenone, p- tertiarybutyldichloroacetophenone, p- 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1 , 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, Butyl ether, benzoin isobutyl ether and 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one.

Examples of the benzyl compound include benzyl and anisyl.

Examples of the benzophenone-based compound include benzophenone, methyl o-benzoylbenzoate, mihira ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, -Methyldiphenyl sulfide, and the like.

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

As the oxime-based compound, a compound represented by the following general formula (VII) or (VIII) is particularly preferable from the viewpoints of sensitivity and heat resistance.

(Wherein R ⁵¹ and R ⁵² each independently represent a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkyl group having 6 to 30 carbon atoms 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 each independently represent 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 each independently represent an 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 Containing group,

X ⁵ represents an oxygen atom, a sulfur atom, a selenium atom, CR ⁷⁵ R ⁷⁶ , CO, NR ⁷⁷ or PR ⁷⁸ ,

X < ⁶ > represents a single bond or CO,

^{R 51, R 52, R 55} , R 56, R 57, R 58, R 59, R 60, R 65, R 66, R 67 and R ⁶⁸ can be of the carbon atoms of 1 to 20 alkyl group, a carbon atom number of 6 to the A methylene group in the alkyl group or the arylalkyl group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, or a heterocyclic ring-containing group, -O-, < / RTI >

R ⁵³ and R ⁵⁴ may each independently form a ring together with any adjacent benzene ring,

a represents an integer of 0 to 4,

and b represents an integer of 0 to 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 each independently represent 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, A heterocyclic ring-containing group having 1 to 20 carbon atoms,

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

R ¹²¹ , R ¹²² and R ¹²³ each independently represent 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, A heterocyclic ring-containing group having 1 to 20 carbon atoms,

The hydrogen atom of the group represented by R ¹²¹ , R ¹²² and R ¹²³ may also be 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 preferably -O-, -S-, -COO-, -OCO-, -NR ¹²⁴ -, -NR ^{124 COO-, -OCONR 124 -, -SCO-,} -COS-, -OCS-, or -CSO- if by optionally substituted 1-5 times under the conditions that do not neighboring oxygen atoms, and also,

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 heterocyclic ring-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 branched side chains or may be cyclic alkyl,

R ¹⁰³ represents a group containing a hydrogen atom, a heterocyclic ring of carbon atoms of 1 to 20 alkyl group, a carbon atom number of 6 to 30 aryl group, a carbon atom number of 7 to 30 arylalkyl group or 2 to 20 carbon atoms of the, R ¹⁰³ , 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 form a ring together,

The hydrogen atoms of the group represented by R ^103, also ^{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 COOR ¹²¹ , OCOR ¹²¹ , COOR ¹²¹ , SCOR ¹²¹ , OCSR ¹²¹ , COSR ¹²¹ , CSOR ¹²¹ , hydroxyl, nitro, CN, halogen atoms, or COOR ¹²¹ ,

R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ are each independently selected from the group consisting of 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 , hydroxyl, CN or a halogen atom, and R ¹⁰⁴ and R ¹⁰⁵ , R ¹⁰⁵ and R ^106, and R ¹⁰⁶ and R ¹⁰⁷ may form a ring together,

R ¹¹⁴ , R ¹¹⁵ and R ^{116 each} represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; R ¹⁰⁸ represents 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 a halogen atom,

w represents 0 or 1.)

Examples of other photo radical polymerization initiators (D) include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro- Yl)] titanium, and the like.

These photo radical polymerization initiators (D) may be used alone or in combination of two or more thereof in accordance with the desired performance.

The photo-radical polymerization initiator (D) as described above is preferably 0.01 to 10% by mass, particularly preferably 0.1 to 1% by mass, in the photosensitive composition of the present invention. If the content of the photo radical polymerization initiator is less than 0.01% by mass, the curing by exposure may become insufficient. If the content is more than 10% by mass, the photo-radical polymerization initiator may precipitate in the photosensitive composition.

A coloring agent may also be added to the photosensitive composition to form a colored photosensitive composition. The cured product of the colored photosensitive composition is suitably used as a color filter.

In the colored photosensitive composition, the amount of the colorant to be added is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass. When the added amount of the coloring agent is less than 0.01% by mass, the color feeling is insufficient, and when it is more than 50% by mass, the coloring agent may precipitate in the photosensitive composition.

Examples of the colorant include a dye and a pigment.

The dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm, and examples thereof include azo compounds, anthraquinone compounds, indigoid compounds, triarylmethane compounds, xanthene compounds, alizarin compounds, A stilbene compound, a thiazole compound, a naphthol compound, a quinoline compound, a nitro compound, an indanamine compound, an oxazine compound, a phthalocyanine compound, a cyanine compound, a diimmonium compound, a cyanoethenyl compound, a dicyanostyrene compound, , A perylene compound, a polyene naphtholactam compound, a coumarin compound, a squarylium compound, a croconium compound, a spiropyran compound, a spirooxazine compound, a meloxic compound, an oxolin compound, a styryl compound, A naphthoquinone compound, an oxazolone compound, a phthalimide compound, a cinnoline compound, a naphthoquinone compound, A quinacridone compound, a diketopyrrolopyrrole compound, an indigo compound, an acridine compound, an azine compound, an azomethine compound, an aniline compound, a quinacridone compound, a quinacridone compound, Quinophthalone compounds, quinone imine compounds, iridium complex compounds, europium complex compounds and the like, and a plurality of these may be used in combination.

As the pigment, an inorganic pigment or an organic pigment can be used. Examples of the pigment include 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, A quinacridone compound, an anthanthrone compound, a perinone compound, a perylene compound, a diketopyrrolopyrrole compound, a thioindigo compound, a dioxazine compound, a triphenylmethane compound, a quinophthalone compound, Naphthalene tetracarboxylic acid; Azo dyes, metal complex compounds of cyanine dyes; Lake pigment; Carbon black obtained by a furnace method, a channel method, and a thermal method; carbon black such as acetylene black, Ketjen black or lamp black; The carbon black is coated with an epoxy resin, the carbon black is dispersed in a solvent in advance in a solvent to adsorb a resin of 20 to 200 mg / g, an acidic or alkaline surface-treated carbon black , An average particle diameter of 8 nm or more and a DBP oil absorption of 90 ml / 100 g or less, a total oxygen amount calculated from CO and CO ₂ in volatile matter at 950 ° C of 9 mg or more per 100 m 2 of the 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, milori blue, cobalt green, cobalt blue, manganese system, ferrocyanide, phosphate salt, persulfate, ultramarine, cerulian blue, viridian, emerald green, sulfuric acid Inorganic pigments such as lead, yellow lead, zinc sulfur, spinach (red iron oxide (III)), cadmium red, synthetic iron black, amber and the like or organic pigments can be used. These pigments may be used singly or in combination.

Examples of the inorganic pigments or organic pigments include commercially available pigments such as Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 180, 184, 185, 192, 200, 202, 209, 215, 216, 169, 169, 170, 171, 177, 179, 180, 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, , 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like.

Water resistance and heat resistance can also be improved by adding a crosslinking agent to the photosensitive composition of the present invention and reacting with the hydrophilic group of the polymer. Examples of the cross-linking agent include a polyoxazoline compound, a carbodiimide compound, an epoxy compound, a polyamine, a polyol, a dicyandiamide derivative, a hydrazine compound, a polyhydrazide compound (dihydrazide, trihydrazide), an aldehyde, A polyisocyanate compound, an alkylene carbonate compound of a phenol compound, a polyvalent metal salt, a silane coupling agent, and an organic titanium. Of these, the polyoxazoline compound and the carbodiimide compound are preferably used in an amount of 100 to 120 Lt; 0 > C.

As the crosslinking agent, commercially available products can be used. Examples of the crosslinking agent include Epocross WS-300, WS-500, WS-700 (manufactured by Nihon Shokubai Co., Ltd.); V-02, V-02-L2, SV-02, V-04, V-10, SW-12G, E-02, E-03A and E-05 (manufactured by Nisshinbo) have.

A solvent may also be added to the photosensitive composition and the colored photosensitive composition. As the solvent, a solvent capable of dissolving or dispersing the respective components may be used, if necessary. Examples of the solvent include methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, Ketones such as hexanone 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 tequil; Cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Alcohol-based solvents such as methanol, ethanol, iso-or n-propanol, iso- or n-butanol, amyl alcohol and diacetone alcohol; Ethylene glycol monomethyl ether acetate, 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-based solvents such as 1-t-butoxy-2-propanol, 3-methoxybutyl acetate and cyclohexanol acetate; BTX type solvents such as benzene, toluene and xylene; Aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; Terpenes such as terphenyl oil, D-limonene, and pinene; Paraffin type solvents such as mineral spirits, Swazol # 310 (Kosomo Matsuyama Chemicals Co., Ltd.), Solvesso # 100 (Exxon Gaku Co., Ltd.); Halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichlorethylene, methylene chloride, and 1,2-dichloroethane; Halogenated aromatic hydrocarbon solvents such as chlorobenzene; There may be used a solvent in which a solvent such as an organic solvent and a solvent such as an organic solvent such as an organic solvent, Dimethyl sulfoxide, water, and the like. These solvents can be used as one or a mixture of two or more solvents. Of these, ketones, ether ester solvents and the like, especially propylene glycol-1-monomethyl ether-2-acetate and cyclohexanone, are preferable because they have good compatibility with a photo-radical polymerization initiator in a photosensitive composition.

The colored photosensitive composition 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; Mica, talc, kaolin, ferrocyanide, various metal sulfates, sulphides, selenides, aluminum silicates, calcium silicates, aluminum hydroxides, calcium silicate, calcium carbonate, magnesium carbonate, cobalt, manganese, , Platinum, gold, silver, copper, and the like.

When a pigment and / or an inorganic compound is used in the colored photosensitive composition, a dispersant may be added. As the dispersing agent, any dispersant that can disperse and stabilize the coloring material and the inorganic compound may be used. A commercially available dispersing agent such as BYK series or BYK series may be used. Examples of the dispersing agent include polyesters, polyethers, polyurethanes , A functional group having a nitrogen atom as a basic functional group and having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g are suitably used.

The above-mentioned colored photosensitive composition may further contain, if necessary, a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol or phenothiazine; Plasticizers; Adhesion promoters; Fillers; Defoamer; Leveling agents; Surface modifiers; Antioxidants such as phenol-based antioxidants, phosphate-based antioxidants, and thioether-based antioxidants; Ultraviolet absorber; Dispersing aids; An anti-aggregation agent; catalyst; Effect promoters; A common additive such as a thickener may be added.

Further, by using another organic polymer together with a polymer having an ethylenically unsaturated bond having the acid value, the properties of the cured product of 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- Polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide , Saturated polyesters, phenol resins, phenoxy resins, polyamideimide resins, polyamic acid resins, and epoxy resins. Of these, polystyrene, (meth) acrylic acid-methyl methacrylate copolymer and epoxy resin are preferable .

A chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine, and the like may be used in combination in the colored photosensitive composition.

As the chain transfer agent and sensitizer, a sulfur atom-containing compound is generally used. 3-mercaptopropionic acid, N- (2-mercaptopropionyl) glycine, 2-mercapto nicotinic acid, 3-mercaptopropionic acid, 3-mercaptopropionic acid and the like are exemplified by thioglycolic acid, thioferric acid, thiosalicylic acid, 2- mercaptopropionic acid, - [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanol Mercaptoethanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercur Mercapto-2-butanol, mercaptophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzoimidazole, 2-mercapto-3- (3-mercaptopropionate), such as dicumyl peroxide, dicumyl peroxide, dicumyl peroxide, dicumyl peroxide, dicumyl peroxide, dicumyl peroxide, dicumyl peroxide, A disulfide compound obtained by oxidizing the mercapto compound, an iodide alkyl compound such as iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid or 3-iodopropanesulfonic acid, or an alkyl iodide compound such as trimethylolpropane tris 3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethylmercaptobenzene, butanediol bistyropropionate, butanediol bisthioglycolate , Ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bis-thiophosphate, trimethylolpropane tristhiopropionate, trimethylolpropane tris thioglycolate, pentaerythritol tetrakisthiopropionate, Pentaerythritol tetrakisthioglycolate, trishydroxyetilide Aliphatic polyfunctional thiol compounds such as styropropionate, the following compound No. C1, and tricercapto propionic acid tris (2-hydroxyethyl) isocyanurate, car lenses MT BD1, PE1, NR1 and the like manufactured by Showa Denko Co., .

Examples of the surfactant include fluorine surfactants such as perfluoroalkyl phosphoric acid esters and perfluoroalkylcarboxylic acid salts; Anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates and alkylsulfates; Cationic surfactants such as higher amine halides and quaternary ammonium salts; Nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides; Amphoteric surfactants; A surfactant such as a silicone surfactant may be used, or a combination thereof may be used.

Examples of the silane coupling agent include silane coupling agents such as KBE-9007, KBM-502, and KBE-403, and silane coupling agents having an isocyanate group, a methacryloyl group, and an epoxy group The ring agent is suitably used.

Examples of the melamine compound include compounds having an active methylol group (CH ₂ OH group) in a nitrogen compound such as (poly) methylol melamine, (poly) methylol glycoluryl, (poly) methylolbenzoguanamine, All or a part (at least two) of which are alkyl-etherified. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group and a butyl group, and they may be the same or different from each other. In addition, the methylol group which is not alkyl-etherified may self-condense in one molecule, and may condense between two molecules, resulting in the formation of an oligomer component. Specifically, hexamethoxymethylmelamine, hexabutoxymethylmelamine, tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril and the like can be used. Of these, alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferred.

The photosensitive composition and the colored photosensitive composition can be applied to a substrate such as a soda glass, a quartz glass, a semiconductor substrate, a metal, a paper, a plastic, etc. by a known means such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, Lt; / RTI > support. Furthermore, once transferred onto a support such as a film, there is no limitation on the application method thereof.

As the light source of the active energy ray used for curing the photosensitive composition and the colored photosensitive composition, those capable of emitting light having a wavelength of 300 to 450 nm can be used. For example, ultra violet mercury vapor, mercury vapor arc, carbon arc, Xenon arc and the like can be used.

In addition, since the laser direct writing method for forming an image directly from digital information such as a computer without using a mask by using laser light for the exposure light source can improve not only productivity but also resolution and positional accuracy As the laser light, light having a wavelength of 340 to 430 nm is suitably used. However, it is also used to emit light in the infrared region from the view of an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, or the like. In the case of using these lasers, a sensitizing dye which absorbs the corresponding infrared region is added from visible.

The photosensitive composition and the colored photosensitive composition of the present invention may be subjected to patterning through a double patterning process in which two photosensitive compositions or colored photosensitive compositions are used to divide and pattern two times.

The photosensitive composition and the colored photosensitive composition of the present invention can be temporarily cured by irradiating the active energy ray and cured by heating. Further, it is also possible to form a pattern by curing by irradiating the active energy ray, developing it, and then heating it.

The photosensitive composition and the colored photosensitive composition (or a cured product thereof) may be applied to a liquid crystal display panel of a color display such as a photo-curing paint or varnish, a photo-curing adhesive, a printed board, or a color TV, a PC monitor, a portable information terminal, A color filter of a CCD image sensor, a photo spacer, a black column spacer, an electrode material for a plasma display panel, a touch panel, a touch sensor, a powder coating, a printing ink, a printing plate, an adhesive, a dental composition, , A gel coat, a photoresist for electronic engineering, an electroplating resist, an etching resist, a liquid and a dry film, a solder resist, a color filter for various display applications, or a plasma display panel, an electroluminescence display, and an LCD A composition for enclosing resist, electric and electronic parts for forming a structure in a manufacturing process; Solder resist; Magnetic recording material; Micro machine parts; Waveguides; Optical switch; A plating mask; An etching mask; Color test system; Glass fiber cable coating; A stencil for screen printing; A material for producing a three-dimensional object by stereolithography; A material for holography recording; Image recording material; Microelectronic circuits; Decolorizing material; A decolorizing material for an image recording material; A decolorizing material for an image recording material using microcapsules; Photoresist materials for printed wiring boards; Photoresist materials for UV and visible laser direct imaging systems; And can be used for various uses such as a photoresist material used for forming a dielectric layer in successive lamination of a printed circuit board, a photoresist material for 3D mounting, a protective film, and the like, and there is no particular limitation on its use.

The photosensitive composition of the present invention can be used for a transparent conductive film, a reflective film, a polarizing plate, a protective film, and the like. The above-described respective layers are successively applied to a transparent substrate, active light is irradiated through a mask having a predetermined pattern shape, Is developed with a developing solution, and the developed coating is heated to be used as a transparent laminate. For example, a transparent thin film layer and a metal thin film layer alternately made of a composite oxide of indium oxide and cerium oxide are alternatively formed on a transparent substrate. The photosensitive composition containing the compound of the present invention as a latent additive may be used for each of the layers described above, and the photosensitive composition may be used for any one or more of the layers. Further, the transparent laminate is more suitably used for a display device.

The colored photosensitive composition is used for the purpose of forming a pixel of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel.

(2) a step of irradiating the coating film with active light through a mask having a predetermined pattern shape, (3) a step of irradiating the coating film with the active light through a mask having a predetermined pattern shape, A step of developing the film after exposure with a developer, and (4) a step of heating the film after development. Further, the colored photosensitive composition of the present invention is also useful as a colored photosensitive composition of an ink-jet system without a development process.

As the mask, a multi-tone mask such as a halftone mask or a gray scale mask may be used.

Example

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

[Preparation Example 1] Preparation of polymer B-3

142 g of glycidyl methacrylate, 8.3 g of styrene, 3.5 g of benzyl methacrylate, 1.0 g of azobisisobutyronitrile and 38.5 g of PGMEA were placed in a reaction vessel and stirred at 90 占 폚 for 9 hours. Thereafter, the reaction solution was cooled to room temperature, 150 g of PGMEA, 72 g of acrylic acid and 0.24 g of tetra-n-butylammonium bromide were added, and the mixture was stirred at 120 캜 for 4 hours. After adding 99.6 g of tetrahydrophthalic anhydride, the mixture was stirred at 100 占 폚 for 4 hours and at 60 占 폚 for 6 hours. Then, 136.5 g of PGMEA was added thereto to obtain a target polymer B-3 as a PGMEA solution (Mw = 22000, Mn = 6000, acid value (solid content) 101 mgKOH / g).

[Preparation Example 2] Preparation of polymer B-4

184 g of 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane, 58 g of acrylic acid, 0.26 g of 2,6-di-tert- 0.11 g of ammonium bromide and 105 g of PGMEA were added and the mixture was stirred at 120 占 폚 for 16 hours. Thereafter, the reaction solution was cooled to room temperature, 160 g of PGMEA, 59 g of biphthalic anhydride and 0.24 g of tetra-n-butylammonium bromide were added, and the mixture was stirred at 120 캜 for 4 hours. 20 g of tetrahydrophthalic anhydride was added and stirred at 120 占 폚 for 4 hours, at 100 占 폚 for 3 hours, at 80 占 폚 for 4 hours, at 60 占 폚 for 6 hours and at 40 占 폚 for 11 hours. Then, 128 g of PGMEA was added, To obtain polymer B-4 (Mw = 5000, Mn = 2100, acid value (solid content): 92.7 mgKOH / g).

[Examples 1 to 11 and Comparative Examples 1 to 2] Preparation of Photosensitive Composition Nos. 1 to 11 and Comparative Photosensitive Compositions Nos. 1 to 2

The photosensitive compositions Nos. 1 to 11 and the comparative photosensitive compositions Nos. 1 to 2 were prepared according to the blend of [Table 1] and [Table 2]. The values in [Table 1] and [Table 2] are parts by mass.

A-1 to A-4 in [Table 1] and [Table 2] show the following potential additives.

B-1 to B-4, B'-1, C-1 to C-2, D-1 to D-3, E-1 and F-1 in [Table 1] B-2 SPC-3000 (an acrylic resin manufactured by Showa Denko K.K., weight average molecular weight 7610 (trade name, manufactured by Showa Denko K.K.) , A double bond equivalent of 340) B-3 (weight average molecular weight 22,000, double bond equivalent 330) B-4 (weight average molecular weight 5600, double bond equivalent 434) obtained in Production Example 2 B'-1 C-2 ARONIX M450 (acrylic monomer, manufactured by Toagosei Co., Ltd.) C-2 KAYARAD DPHA (multifunctional acrylate; Nippon Kaya Co., D-3 TR-PBG-304 (manufactured by Tronly) E-1 Propylene glycol-1-monomethyl ether- 2-Acetate F-1 Blue pigment dispersion (CI. 15 parts by mass of Graft Blue 15: 6, 12.5 parts by mass (solid content concentration: 40% by mass) of BYK161 (manufactured by BYK) as a dispersant and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent, By a bead mill.)

[Evaluation Examples 1-1 to 1-11 and Comparative Evaluation Examples 1-1 to 1-2] Evaluation of heat resistance by firing

Comparative Photosensitive Compositions No.1 to No.2 prepared in Photosensitive Compositions No.1 to No.11 and Comparative Examples 1 to 2 prepared in Examples 1 to 11 were each coated on a glass substrate under the conditions of 410 rpm x 7 sec, The plate was dried (90 DEG C, 90 seconds). The resulting coating film was exposed (40 mJ / cm 2) with an ultra-high pressure mercury lamp. The coated film after the exposure was fired under the conditions of 230 DEG C x 90 minutes, and the transmittance of the coated film after firing was measured at 400 nm. The results are shown in Table 3.

[Evaluation Examples 2-1 to 2-11 and Comparative Evaluation Examples 2-1 to 2-2] Evaluation of solvent resistance

Comparative Photosensitive Compositions No.1 to No.2 obtained in Photosensitive Compositions Nos. 1 to 11 and Comparative Examples 1 to 2 obtained in Examples 1 to 10 were coated on a glass substrate under the conditions of 410 rpm x 7 sec. Dried (90 DEG C, 90 seconds). The obtained coating film was exposed (40 mJ / cm 2) with an ultra-high pressure mercury lamp, and immersed in cyclohexanone, PGMEA, N-methylpyrrolidone and N-ethylpyrrolidone for 30 minutes each. Thereafter, the film was washed and dried with ion-exchanged water, and the film thickness before and after the immersion test for each solvent was examined. A, B, or 8% when the swelling rate is less than 0 to 2%, A, less than 2 to 8%, and swelling rate (%) = (film thickness after test-film thickness before test) , The film thickness after the test was D, and the film thickness after the test was D before the test. The results are shown in Table 4.

From the above results, the photosensitive composition of the present invention is maintained in high transparency after firing, that is, it has high heat resistance and excellent solvent resistance.

According to the present invention, it is possible to provide a photosensitive composition giving a cured product having high heat resistance and solvent resistance.

Claims (3)

(A) containing a latent additive (A), an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a double bond equivalent of 200 to 1000, a photosensitive monomer (B) containing an acrylic monomer (C) Composition. A method of curing a photosensitive composition according to claim 1 by irradiating (irradiating) an active energy ray. A cured product of the photosensitive composition according to claim 1.