KR102429609B1 - Photosensitive resin composition - Google Patents

Abstract

(Project) A color filter comprising a photosensitive resin composition containing a chromatic colorant capable of forming a color filter with excellent luminance, a pattern forming method using the photosensitive resin composition, and a colored layer formed using the photosensitive resin composition; , to provide a display element provided with the color filter.
(Solution means) (A) alkali-soluble resin, (B) photopolymerizable monomer, (C) photoinitiator, and specific imidazole skeleton-containing photosensitive resin composition containing chromatic (E) coloring agent The compound of the structure is contained.

Description

Photosensitive resin composition {PHOTOSENSITIVE RESIN COMPOSITION}

The present invention relates to a photosensitive resin composition, a pattern forming method using the photosensitive resin composition, a color filter, and a display element.

The color filter used for a liquid crystal panel, an image sensor, etc. is generally manufactured by the lithographic method. In this lithographic method, after apply|coating a black photosensitive resin composition to a glass substrate first, it exposes and develops and forms a black matrix. Then, by repeating application|coating, exposure, and image development for every photosensitive resin composition to which the organic pigment of each color of green, blue, and red was added, the pattern of each color is formed in a predetermined position, and a color filter is manufactured.

Generally, it is calculated|required by the color filter formed using the photosensitive resin composition that it is excellent in heat resistance. For this reason, the photosensitive resin composition containing the compound which has a specific cyclic amidine structure, for example as a photosensitive resin composition which can form the color filter by which heat resistance was improved is proposed (patent document 1).

International Publication No. 2011/13318

On the other hand, general color filters WHEREIN: In order to improve the utilization efficiency of light emitted from light sources, such as a point of image quality of a display element, and a backlight, the improvement of a brightness|luminance is calculated|required.

However, in the photosensitive resin composition of patent document 1, there exists a problem that a color filter with a favorable brightness|luminance cannot necessarily be formed.

The present invention has been made in view of the above problems, a photosensitive resin composition containing a chromatic colorant capable of forming a color filter having excellent luminance, a pattern forming method using the photosensitive resin composition, and a photosensitive resin composition formed using the photosensitive resin composition It aims at providing the color filter provided with a colored layer, and the display element provided with the said color filter.

As a result of intensive research, the present inventors have already prepared a photosensitive resin composition containing (A) alkali-soluble resin, (B) photopolymerizable monomer, (C) photoinitiator, and chromatic (E) colorant. It discovered that the said subject could be solved by containing the compound of the specific structure containing dazole skeleton, and came to complete this invention.

A first aspect of the present invention comprises (A) an alkali-soluble resin, (B) a photopolymerizable monomer, (C) a photoinitiator, (D) a compound represented by the following formula (1), and a chromatic (E) colorant. It is the photosensitive resin composition to contain.

[Formula 1]

(In formula (1), R ¹ is a hydrogen atom or an alkyl group, R ² is an aromatic group which may have a substituent, R ³ is an alkylene group which may have a substituent, R ⁴ is a halogen atom, a hydroxyl group, or a mercap an earthenware group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphonato group, or an organic group, and n is an integer of 0 to 3)

A second aspect of the present invention is

A step of applying the photosensitive resin composition according to the first aspect on a substrate to form a coating film;

a step of positionally selectively exposing the coating film;

It is a formation method of a pattern including the process of developing the exposed coating film.

A 3rd aspect of this invention is a color filter provided with the colored layer formed using the photosensitive resin composition which concerns on a 1st aspect.

A 4th aspect of this invention is a display element provided with the color filter which concerns on a 3rd aspect.

According to the present invention, a color comprising a photosensitive resin composition containing a chromatic colorant capable of forming a color filter having excellent luminance, a pattern forming method using the photosensitive resin composition, and a colored layer formed using the photosensitive resin composition A filter and a display element provided with the color filter can be provided.

«Photosensitive resin composition»

The photosensitive resin composition of this invention contains (A) alkali-soluble resin, (B) a photopolymerizable monomer, (C) a photoinitiator, (D) the compound represented by Formula (1), and a chromatic (E) coloring agent do. First, these constituents will be described.

<(A) alkali-soluble resin>

(A) It does not specifically limit as alkali-soluble resin, Conventionally well-known alkali-soluble resin can be used. This (A) alkali-soluble resin may have an ethylenically unsaturated group, and may not have an ethylenically unsaturated group.

In addition, in this specification, (A) alkali-soluble resin forms a resin film with a film thickness of 1 micrometer on a glass substrate with the resin solution (solvent: propylene glycol monomethyl ether acetate) with a resin concentration of 20 mass %, 2.38 When it is made to be immersed in the mass % tetramethylammonium hydroxide (TMAH) aqueous solution for 1 minute, it means that it melt|dissolves with a film thickness of 0.01 micrometer or more.

As (A) alkali-soluble resin which has an ethylenically unsaturated group, resin obtained by making the reaction material of an epoxy compound and unsaturated carboxylic acid react with polybasic acid anhydride further can be used, for example.

Especially, resin represented by a following formula (a-1) is preferable. Resin represented by this formula (a-1) is preferable at the point itself with high photocurability.

[Formula 2]

In the formula (a-1), X ^a represents a group represented by the following formula (a-2).

[Formula 3]

In the formula (a-2), R ^a1 each independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a halogen atom, R ^a2 each independently represents a hydrogen atom or a methyl group, and W ^a is a single bond. Or group represented by the following formula (a-3) is shown.

[Formula 4]

Moreover, in said formula (a-1), Y ^a represents the residue which removed the acid anhydride group (-CO-O-CO-) from dicarboxylic acid anhydride. Examples of dicarboxylic anhydrides include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, chlorendic anhydride, methyltetrahydroanhydride Phthalic acid, glutaric anhydride, etc. are mentioned.

Moreover, in said Formula (a-1), Z ^a represents the residue which removed two acid anhydride groups from tetracarboxylic dianhydride. As an example of tetracarboxylic dianhydride, pyromellitic dianhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, biphenyl ether tetracarboxylic dianhydride, etc. are mentioned.

Moreover, in said formula (a-1), m represents the integer of 0-20.

Moreover, as (A) alkali-soluble resin which has an ethylenically unsaturated group, Polyester (meth)acrylate obtained by making (meth)acrylic acid react with the polyester prepolymer obtained by condensing polyhydric alcohol and monobasic acid or polybasic acid; Polyurethane (meth)acrylate obtained by making (meth)acrylic acid react, after making a polyol and the compound which has two isocyanate groups react; Bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol or cresol novolak type epoxy resin, resor type epoxy resin, triphenol methane type epoxy resin, polycarboxylic acid polyglycidyl ester, polyol An epoxy (meth)acrylate resin obtained by reacting (meth)acrylic acid with an epoxy resin such as polyglycidyl ester, aliphatic or alicyclic epoxy resin, amine epoxy resin, or dihydroxybenzene type epoxy resin may also be used. .

In addition, in this specification, "(meth)acrylic acid" means both acrylic acid and methacrylic acid. Similarly, "(meth)acrylate" means both an acrylate and a methacrylate.

On the other hand, as (A) alkali-soluble resin which does not have an ethylenically unsaturated group, resin obtained by copolymerizing an unsaturated carboxylic acid, the epoxy group containing unsaturated compound which does not have an alicyclic group, and an alicyclic group containing unsaturated compound at least can be used.

As an unsaturated carboxylic acid, Monocarboxylic acids, such as (meth)acrylic acid and a crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid; anhydrides of these dicarboxylic acids; and the like. Among these, (meth)acrylic acid and maleic anhydride are preferable from points, such as copolymerization reactivity, alkali solubility of resin obtained, and availability. These unsaturated carboxylic acids can be used individually or in combination of 2 or more types.

Examples of the epoxy group-containing unsaturated compound having no alicyclic group include glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 6,7-epoxy (meth)acrylic acid epoxy alkyl esters, such as heptyl (meth)acrylate and 3, 4- epoxycyclohexyl (meth)acrylate; α-alkyl acrylic acid epoxyalkyl esters such as α-ethyl acrylate glycidyl, α-n-propyl glycidyl acrylate, α-n-butyl acrylate glycidyl, and α-ethyl acrylic acid 6,7-epoxyheptyl; Glycidyl ethers, such as o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, and p-vinyl benzyl glycidyl ether; and the like. Among these, glycidyl (meth) acrylate, 2-methylglycidyl (meth) acrylate, 6,7-epoxyheptyl (meth) acrylate, -Vinylbenzylglycidylether, m-vinylbenzylglycidylether, and p-vinylbenzylglycidylether are preferable. These epoxy-group containing unsaturated compounds can be used individually or in combination of 2 or more types.

As an alicyclic group-containing unsaturated compound, if it is an unsaturated compound which has an alicyclic group, it will not specifically limit. The alicyclic group may be monocyclic or polycyclic. Examples of the monocyclic alicyclic group include a cyclopentyl group and a cyclohexyl group. Examples of the polycyclic alicyclic group include an adamantyl group, a norbornyl group, an isobornyl group, a tricyclononyl group, a tricyclodecyl group, and a tetracyclododecyl group. Specific examples of the alicyclic group-containing unsaturated compound include compounds represented by the following formula.

[Formula 5]

In the formula, R ^a3 represents a hydrogen atom or a methyl group, R ^a4 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, and R ^a5 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. As R ^a4 , a single bond, linear or branched alkylene group, for example, a methylene group, ethylene group, propylene group, tetramethylene group, ethylethylene group, pentamethylene group, or hexamethylene group is preferable. As R ^a5 , for example, a methyl group or an ethyl group is preferable.

It is preferable that it is 3-25 mass %, and, as for the ratio of the structural unit derived from the said unsaturated carboxylic acid in this (A) alkali-soluble resin, it is more preferable that it is 5-25 mass %. Moreover, it is preferable that it is 71-95 mass %, and, as for the ratio of the structural unit derived from the said epoxy-group containing unsaturated compound, it is more preferable that it is 75-90 mass %. Moreover, it is preferable that it is 1-25 mass %, as for the ratio of the structural unit derived from the said alicyclic group containing unsaturated compound, it is more preferable that it is 3-20 mass %, It is still more preferable that it is 5-15 mass %. By setting it as said range, the intensity|strength after hardening of the adhesiveness to the glass substrate of the photosensitive resin composition and the photosensitive resin composition can be raised, making alkali solubility of resin obtained suitable.

(A) It is preferable that it is 1000-40000, and, as for the mass average molecular weight of alkali-soluble resin, it is more preferable that it is 2000-30000. By setting it as said range, sufficient heat resistance and film strength can be acquired, obtaining favorable developability.

(A) It is preferable that it is 10-50 mass % with respect to solid content of the photosensitive resin composition, and, as for content of alkali-soluble resin, it is more preferable that it is 20-40 mass %. The solid content here is a component other than a solvent. (A) When there is too little content of alkali-soluble resin, for example, alkali developability may fall or there exists a possibility that the storage stability of the photosensitive resin composition obtained may fall, on the other hand, when there is too much, relatively (E) coloring agent Since the density is lowered, there is a fear that it may become difficult to achieve a target color density as a thin film.

<(B) photopolymerizable monomer>

The photosensitive resin composition of this invention contains (B) a photopolymerizable monomer. (B) As a photopolymerizable monomer, there exist a monofunctional monomer and a polyfunctional monomer.

Examples of the monofunctional monomer include (meth)acrylamide, methylol (meth)acrylamide, methoxymethyl (meth)acrylamide, ethoxymethyl (meth)acrylamide, propoxymethyl (meth)acrylamide, butoxymethyl Toxymethyl (meth) acrylamide, N-methylol (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, (meth) acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, Citraconic acid, citraconic anhydride, crotonic acid, 2-acrylamide-2-methylpropanesulfonic acid, tert-butylacrylamidesulfonic acid, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate , 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylic Rate, 2-phenoxy-2-hydroxypropyl (meth) acrylate, 2- (meth) acryloyloxy-2-hydroxypropyl phthalate, glycerin mono (meth) acrylate, tetrahydrofurfuryl (meth) Acrylate, dimethylamino (meth) acrylate, glycidyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) ) acrylate and half (meth)acrylate of a phthalic acid derivative. These monofunctional monomers can be used individually or in combination of 2 or more types.

On the other hand, as the polyfunctional monomer, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexane glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerin Di(meth)acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di(meth)acrylate, pentaerythritol Tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 2,2-bis (4- (meth) Acryloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxypolyethoxyphenyl)propane, 2-hydroxy-3-(meth)acryloyloxypropyl (meth)acrylate, ethylene Glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, phthalic acid diglycidyl ester di (meth) acrylate, glycerin triacrylate, glycerin polyglycy Diyl ether poly (meth) acrylate, urethane (meth) acrylate (i.e. tolylene diisocyanate), trimethylhexamethylene diisocyanate, hexamethylene diisocyanate and 2-hydroxyethyl (meth) acrylate reaction product, methylenebis ( Polyfunctional monomers, such as condensate of meth)acrylamide, (meth)acrylamide methylene ether, polyhydric alcohol, and N-methylol (meth)acrylamide, triacryl formal, etc. are mentioned. These polyfunctional monomers can be used individually or in combination of 2 or more types.

It is preferable that it is 10-50 mass % with respect to solid content of the photosensitive resin composition, and, as for content of the (B) photopolymerizable monomer in the photosensitive resin composition, it is more preferable that it is 20-40 mass %. In this case, when there is too little content of (B) photopolymerizable monomer, there exists a possibility that sufficient sclerosis|hardenability may not be obtained, and when there is too much content, alkali developability falls, on the glass substrate of an unexposed part, or on the light shielding layer There is a tendency for background soiling, film residue, and the like to easily occur.

<(C) Photoinitiator>

(C) It does not specifically limit as a photoinitiator, A conventionally well-known photoinitiator can be used.

(C) Specifically, as a photoinitiator, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy) ) Phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4- dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, bis(4-dimethylaminophenyl)ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 4-benzoyl-4'- Methyl dimethyl sulfide, 4-dimethylamino benzoic acid, 4-dimethylamino methyl benzoate, 4-dimethylamino ethyl benzoate, 4-dimethylamino butyl benzoate, 4-dimethylamino-2-ethylhexyl benzoic acid, 4-dimethylamino-2- Isoamylbenzoic acid, benzyl-β-methoxyethyl acetal, benzyldimethylketal, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, methyl o-benzoylbenzoate, 2,4- Diethyl thioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 1-chloro-4-propoxythioxanthone, thioxanthene, 2-chlorothioxanthene, 2,4-di Ethylthioxanthene, 2-methylthioxanthene, 2-isopropylthioxanthene, 2-ethylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-diphenylanthraquinone, azobis Isobutyronitrile, benzoyl peroxide, cumene peroxide, 2-mercaptobenzoimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-(o-chlorophenyl)-4,5- Diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimida Sol dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer, 2, 4,5-triarylimidazole dimer, benzophenone, 2-chlorobenzophenone, 4,4'-bisdimethylaminobenzophenone (ie Michler's ketone), 4,4'-bisdiethylaminobenzophenone (ie, ethyl michler ketone), 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone, benzyl, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl Ether, benzoin-n-butyl ether, benzoin isobutyl Ether, benzoinbutyl ether, acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, p-tert-butylacetophenone, p-dimethylaminoacetophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, α,α-dichloro-4-phenoxyacetophenone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, pentyl-4-dimethylaminobenzoate, 9-phenylacridine, 1,7-bis-(9-acridinyl)heptane, 1,5-bis- (9-acridinyl)pentane, 1,3-bis-(9-acridinyl)propane, p-methoxytriazine, 2,4,6-tris(trichloromethyl)-s-triazine, 2 -Methyl-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s -triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2- Methylphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl) -s-triazine, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxystyryl)-4,6-bis(trichloro Rhomethyl)-s-triazine, 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis-trichloromethyl-6-( 3-Bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)phenyl-s-triazine, 2,4 -Bis-trichloromethyl-6- (3-bromo-4-methoxy) styrylphenyl-s-triazine, 2,4-bis-trichloromethyl-6- (2-bromo-4-methyl Toxy) styrylphenyl-s-triazine, "IRGACURE OXE02", "IRGACURE OXE01", "IRGACURE 369", "IRGACURE 651", "IRGACURE 907" (product name: manufactured by BASF), "NCI-831" (brand name: ADEKA) etc. are mentioned. These (C) photoinitiators can be used individually or in combination of 2 or more types.

It is preferable that the photosensitive resin composition contains an oxime ester compound as a (C) photoinitiator among the compounds demonstrated above. An oxime ester compound is the compound which two organic groups couple|bonded through the oxime ester bond represented by =N-O-CO-. When mix|blending an oxime ester compound with the photosensitive resin composition as a (C) photoinitiator, it is easy to obtain the photosensitive resin composition excellent in exposure sensitivity.

(C) The oxime ester compound used as a photoinitiator is not specifically limited, A conventionally well-known thing can be used. In an oxime ester compound, the compound represented by a following formula (c1) is preferable.

[Formula 6]

In the formula (c1), R ^c1 represents an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted phenyl group, or an optionally substituted carbazolyl group. a is 0 or 1. R ^c2 represents an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted phenyl group, or an optionally substituted carbazolyl group. R ^c3 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group which may have a substituent.

When R ^c1 is an alkyl group having 1 to 10 carbon atoms which may have a substituent, the type of the substituent in the alkyl group is not particularly limited as long as the object of the present invention is not impaired.

As an example of a preferable substituent which the C1-C10 alkyl group may have, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkoxy group, carbon A saturated aliphatic acyl group having 2 to 20 atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a saturated aliphatic acyloxy group having 2 to 20 carbon atoms, a phenyl group which may have a substituent, a phenoxy group which may have a substituent, a substituent A phenylthio group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a benzoyloxy group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a substituent A naphthyl group which may have a substituent, a naphthoxy group which may have a substituent, a naphthoyl group which may have a substituent, a naphthoxycarbonyl group which may have a substituent, a naphthoyloxy group which may have a substituent, a carbon which may have a substituent A naphthylalkyl group having 11 to 20 atoms, a heterocyclyl group which may have a substituent, a heterocyclylcarbonyl group which may have a substituent, an amino group, an amino group substituted with an organic group of 1 or 2, a morpholin-1-yl group, and a pipette and a razin-1-yl group, a halogen, a nitro group, and a cyano group.

A C1-C10 alkyl group may be linear or a branched chain may be sufficient as it. In this case, 1-8 are preferable and, as for carbon atom number of an alkyl group, 1-5 are more preferable.

When R ^c1 is a phenyl group which may have a substituent, the type of the substituent is not particularly limited as long as the object of the present invention is not impaired. Preferred examples of the substituent which the phenyl group may have include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, a phenyl group which may have a substituent, and a phenoxy group which may have a substituent. Period, the benzoyl group which may have a substituent, the phenoxycarbonyl group which may have a substituent, the benzoyloxy group which may have a substituent, the phenylalkyl group which may have a substituent, the naphthyl group which may have a substituent, the naphthyl which may have a substituent Toxy group, naphthoyl group which may have a substituent, naphthoxycarbonyl group which may have a substituent, naphthoyloxy group which may have a substituent, naphthylalkyl group which may have a substituent, heterocyclyl group which may have a substituent, amino group , an amino group substituted with 1 or 2 organic groups, a morpholin-1-yl group, and a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When R ^c1 is a phenyl group which may have a substituent, and the phenyl group has a plurality of substituents, the plurality of substituents may be the same or different.

When the substituent which a phenyl group has is an alkyl group, 1-20 are preferable, as for the number of carbon atoms, 1-10 are more preferable, 1-6 are still more preferable, 1-3 are especially preferable, and 1 is the most preferable. do. Moreover, linear may be sufficient as an alkyl group, and branched chain may be sufficient as it. Specific examples when the substituent of the phenyl group is an alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group , isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isono A nyl group, an n-decyl group, an isodecyl group, etc. are mentioned. Moreover, the alkyl group may contain the ether bond (-O-) in a carbon chain. In this case, as a substituent which a phenyl group has, an alkoxyalkyl group and an alkoxyalkoxyalkyl group are mentioned, for example. When the substituent of the phenyl group is an alkoxyalkyl group, the group represented by -R ^c4 -OR ^c5 is preferable. R ^c4 is an alkylene group having 1 to 10 carbon atoms which may be linear or branched. R ^c5 is an alkyl group having 1 to 10 carbon atoms which may be linear or branched. 1-8 are preferable, as for carbon atom number of ^Rc4 , 1-5 are more preferable, and 1-3 are especially preferable. 1-8 are preferable, as for carbon atom number of R<^c5> , 1-5 are more preferable, 1-3 are especially preferable, and 1 is the most preferable. Examples of the alkyl group having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.

When the substituent which a phenyl group has is an alkoxy group, 1-20 are preferable and, as for the number of carbon atoms, 1-6 are more preferable. Moreover, linear may be sufficient as an alkoxy group, and branched chain may be sufficient as it. Specific examples when the substituent of the phenyl group is an alkoxy group include a methoxy group, an ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert- Butyloxy group, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec -octyloxy group, tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, isodecyloxy group, etc. are mentioned. Moreover, the alkoxy group may contain the ether bond (-O-) in a carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include methoxyethoxy group, ethoxyethoxy group, 2-methoxy-1-methylethoxy group, methoxyethoxyethoxy group, ethoxyethoxy group A oxy group, a propyloxyethoxyethoxy group, a methoxypropyloxy group, etc. are mentioned.

When the substituent which a phenyl group has is a cycloalkyl group or a cycloalkoxy group, 3-10 are preferable and, as for the number of carbon atoms, 3-6 are more preferable. Specific examples in the case where the substituent of the phenyl group is a cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Specific examples when the substituent of the phenyl group is a cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group. .

When the substituent which a phenyl group has is a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, 2-20 are preferable and, as for the number of carbon atoms, 2-7 are more preferable. Specific examples when the substituent of the phenyl group is a saturated aliphatic acyl group include an acetyl group, a propanoyl group, n-butanoyl group, 2-methylpropanoyl group, n-pentanoyl group, 2,2-dimethylpropanoyl group, n -hexanoyl group, n-heptanoyl group, n-octanoyl group, n-nonanoyl group, n-decanoyl group, n-undecanoyl group, n-dodecanoyl group, n-tridecanoyl group, n-tetradecano group diary, n-pentadecanoyl group, and n-hexadecanoyl group; and the like. Specific examples when the substituent of the phenyl group is a saturated aliphatic acyloxy group include an acetyloxy group, propanoyloxy group, n-butanoyloxy group, 2-methylpropanoyloxy group, n-pentanoyloxy group, 2,2- Dimethylpropanoyloxy group, n-hexanoyloxy group, n-heptanoyloxy group, n-octanoyloxy group, n-nonanoyloxy group, n-decanoyloxy group, n-undecanoyloxy group, n-dodecano group A yloxy group, n-tridecanoyloxy group, n-tetradecanoyloxy group, n-pentadecanoyloxy group, n-hexadecanoyloxy group, etc. are mentioned.

When the substituent which a phenyl group has is an alkoxycarbonyl group, 2-20 are preferable and, as for the carbon atom number, 2-7 are more preferable. Specific examples when the substituent of the phenyl group is an alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, and a sec-butyloxycarbonyl group. , tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, sec-pentyloxycarbonyl group, tert-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl group, n-octyloxycarbonyl group, isooctyl group and oxycarbonyl group, sec-octyloxycarbonyl group, tert-octyloxycarbonyl group, n-nonyloxycarbonyl group, isononyloxycarbonyl group, n-decyloxycarbonyl group, and isodecyloxycarbonyl group.

When the substituent which a phenyl group has is a phenylalkyl group, 7-20 are preferable and, as for the carbon atom number, 7-10 are more preferable. Moreover, when the substituent which a phenyl group has is a naphthylalkyl group, 11-20 are preferable and, as for the carbon atom number, 11-14 are more preferable. Specific examples in the case where the substituent of the phenyl group is a phenylalkyl group include a benzyl group, a 2-phenylethyl group, a 3-phenylpropyl group, and a 4-phenylbutyl group. Specific examples of the case where the substituent of the phenyl group is a naphthylalkyl group include an α-naphthylmethyl group, a β-naphthylmethyl group, a 2-(α-naphthyl)ethyl group, and a 2-(β-naphthyl)ethyl group. can When the substituent of the phenyl group is a phenylalkyl group or a naphthylalkyl group, the substituent may further have a substituent on the phenyl group or the naphthyl group.

When the substituent of the phenyl group is a heterocyclyl group, the heterocyclyl group is a 5-membered or 6-membered monocyclic ring containing one or more N, S, O, or a heterocycle in which these monocyclic rings or such a monocyclic ring and a benzene ring are condensed It's Lilgi When the heterocyclyl group is a condensed ring, it is assumed that the number of rings is up to 3. Heterocyclic rings constituting such a heterocyclyl group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, Pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzoimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, and quinoxaline; and the like. When the substituent which the phenyl group has is a heterocyclyl group, the heterocyclyl group may have a substituent further.

When the substituent of the phenyl group is an amino group substituted with an organic group of 1 or 2, preferred examples of the organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a cycloalkyl group having 2 to 20 carbon atoms. A saturated aliphatic acyl group, a saturated aliphatic acyloxy group having 2 to 20 carbon atoms, an optionally substituted phenyl group, an optionally substituted benzoyl group, an optionally substituted phenylalkyl group having 7 to 20 carbon atoms, a substituent The naphthyl group which you may have, the naphthoyl group which may have a substituent, a C11-C20 naphthylalkyl group which may have a substituent, a heterocyclyl group, etc. are mentioned. As a specific example of these preferable organic groups, the thing similar to what was mentioned above about the substituent which a phenyl group has is mentioned. Specific examples of the amino group substituted with 1 or 2 organic groups include methylamino group, ethylamino group, diethylamino group, n-propylamino group, di-n-propylamino group, isopropylamino group, n-butylamino group, di-n- Butylamino group, n-pentylamino group, n-hexylamino group, n-heptylamino group, n-octylamino group, n-nonylamino group, n-decylamino group, phenylamino group, naphthylamino group, acetylamino group, propanoylamino group, n- Butanoylamino group, n-pentanoylamino group, n-hexanoylamino group, n-heptanoylamino group, n-octanoylamino group, n-decanoylamino group, benzoylamino group, α-naphthoylamino group, β-naphthoylamino group, and N-acetyl-N-acetyloxyamino group, etc. are mentioned.

Examples of the substituent when the phenyl group, naphthyl group, and heterocyclyl group contained in the substituent of the phenyl group further have a substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and the number of carbon atoms. A monoalkylamino group having a saturated aliphatic acyl group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, and 1 carbon atom. and a dialkylamino group having an alkyl group of -6, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in the substituent of the phenyl group further have a substituent, the number of the substituents is not limited within a range that does not impair the object of the present invention, but preferably 1 to 4 . When the phenyl group, the naphthyl group, and the heterocyclyl group contained in the substituent which the phenyl group has have a plurality of substituents, the plurality of substituents may be the same or different.

As mentioned above, although the substituent in the case where R ^c1 is the phenyl group which may have a substituent was demonstrated, an alkyl group or an alkoxyalkyl group is preferable among these substituents.

When R ^c1 is a phenyl group which may have a substituent, the number of substituents and the bonding position of the substituents are not particularly limited as long as the object of the present invention is not impaired. When R ^c1 is a phenyl group which may have a substituent, it is preferable that the phenyl group which may have a substituent is an optionally substituted o-tolyl group from the viewpoint of excellent base generation efficiency.

When R ^c1 is a carbazolyl group which may have a substituent, the type of the substituent is not particularly limited as long as the object of the present invention is not impaired. As an example of a preferable substituent which the carbazolyl group may have on a carbon atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, C3 A cycloalkoxy group of 10 to 10 carbon atoms, a saturated aliphatic acyl group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a saturated aliphatic acyloxy group having 2 to 20 carbon atoms, a phenyl group which may have a substituent, a substituent A phenoxy group which may have a substituent, a phenylthio group which may have a substituent, a phenylcarbonyl group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a benzoyloxy group which may have a substituent, A phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoxy group which may have a substituent, a naphthylcarbonyl group which may have a substituent, a naphthoyl group which may have a substituent, naphthoxycarbonyl group which may have a substituent, naphthoyloxy group which may have a substituent, a naphthylalkyl group having 11 to 20 carbon atoms which may have a substituent, heterocyclyl group which may have a substituent, hetero which may have a substituent and a cyclylcarbonyl group, an amino group, an amino group substituted with 1 or 2 organic groups, a morpholin-1-yl group, and a piperazin-1-yl group, a halogen, a nitro group, and a cyano group.

When R ^c1 is a carbazolyl group which may have a substituent, examples of the preferable substituent which the carbazolyl group may have on the nitrogen atom include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, A saturated aliphatic acyl group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, and a substituent A phenylalkyl group having 7 to 20 carbon atoms, an optionally substituted naphthyl group, an optionally substituted naphthoyl group, an optionally substituted naphthoxycarbonyl group, an optionally substituted naphthyl having 11 to 20 carbon atoms A tylalkyl group, the heterocyclyl group which may have a substituent, the heterocyclylcarbonyl group which may have a substituent, etc. are mentioned. In these substituents, a C1-C20 alkyl group is preferable, a C1-C6 alkyl group is more preferable, and an ethyl group is especially preferable.

For specific examples of the substituent which the carbazolyl group may have, an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, a phenylalkyl group which may have a substituent, and a substituent As for the amino group substituted with the optionally naphthylalkyl group, the optionally substituted heterocyclyl group, and the organic group of 1 or 2, examples of the substituents the phenyl group has when R ^c1 is the phenyl group which may have a substituent include same.

Examples of the substituent when the phenyl group, naphthyl group, and heterocyclyl group contained in the substituent of the carbazolyl group for R ^c1 further have a substituent include an alkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; a saturated aliphatic acyl group having 2 to 7 carbon atoms; an alkoxycarbonyl group having 2 to 7 carbon atoms; a C2-C7 saturated aliphatic acyloxy group; phenyl group; naphthyl group; benzoyl group; naphthoyl group; a benzoyl group substituted with a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; monoalkylamino group which has a C1-C6 alkyl group; dialkylamino group which has a C1-C6 alkyl group; morpholin-1-yl group; piperazin-1-yl group; halogen ; nitro group; and cyano groups. When the phenyl group, naphthyl group, and heterocyclyl group contained in the substituent of the carbazolyl group further have a substituent, the number of the substituents is not limited within a range that does not impair the object of the present invention, but 1-4 desirable. When the phenyl group, the naphthyl group, and the heterocyclyl group have a plurality of substituents, the plurality of substituents may be the same or different.

R ^c2 is an alkyl group having 1 to 10 carbon atoms which may have a substituent, a phenyl group which may have a substituent, or a carbazolyl group which may have a substituent.

When R ^c2 is an alkyl group having 1 to 10 carbon atoms which may have a substituent, the alkyl group may be linear or branched. In this case, 1-8 are preferable and, as for carbon atom number of an alkyl group, 1-5 are more preferable.

In R ^c2 , the substituent included in the alkyl group or the phenyl group is not particularly limited as long as the object of the present invention is not impaired.

Examples of the preferable substituent which the alkyl group may have on a carbon atom include an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, and 2 carbon atoms. A saturated aliphatic acyl group of to 20, an alkoxycarbonyl group of 2 to 20 carbon atoms, a saturated aliphatic acyloxy group of 2 to 20 carbon atoms, a phenyl group which may have a substituent, a phenoxy group which may have a substituent, or a substituent A phenylthio group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a benzoyloxy group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, even if it has a substituent naphthyl group which may have a substituent, a naphthoxy group which may have a substituent, a naphthoyl group which may have a substituent, a naphthoxycarbonyl group which may have a substituent, a naphthoyloxy group which may have a substituent, 11 carbon atoms which may have a substituent to 20 naphthylalkyl group, optionally substituted heterocyclyl group, optionally substituted heterocyclylcarbonyl group, amino group, amino group substituted with 1 or 2 organic groups, morpholin-1-yl group, and piperazine-1 - a diyl group, a halogen group, a nitro group, and a cyano group etc. are mentioned.

As an example of the preferable substituent which the phenyl group may have on a carbon atom, in addition to the group illustrated above as a preferable substituent which an alkyl group may have on a carbon atom, a C1-C20 alkyl group is mentioned.

For specific examples of the substituent which the alkyl group or phenyl group may have, an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, a phenylalkyl group which may have a substituent, and a substituent As for the amino group substituted with the optionally naphthylalkyl group, the optionally substituted heterocyclyl group, and the organic group of 1 or 2, examples of the substituents the phenyl group has when R ^c1 is the phenyl group which may have a substituent include same.

Examples of the substituent when the phenyl group, naphthyl group, and heterocyclyl group contained in the substituent which the alkyl group or the phenyl group has in R ^c2 has a substituent include an alkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; a saturated aliphatic acyl group having 2 to 7 carbon atoms; an alkoxycarbonyl group having 2 to 7 carbon atoms; a C2-C7 saturated aliphatic acyloxy group; phenyl group; naphthyl group; benzoyl group; naphthoyl group; a benzoyl group substituted with a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; monoalkylamino group which has a C1-C6 alkyl group; dialkylamino group which has a C1-C6 alkyl group; morpholin-1-yl group; piperazin-1-yl group; halogen ; nitro group; and cyano groups. When the phenyl group, naphthyl group, and heterocyclyl group contained in the substituent group possessed by the alkyl group or the phenyl group further have a substituent, the number of the substituents is not limited within a range that does not impair the object of the present invention, but 1-4 desirable. When the phenyl group, the naphthyl group, and the heterocyclyl group have a plurality of substituents, the plurality of substituents may be the same or different.

When R ^c2 is a carbazolyl group which may have a substituent, the kind of the substituent which the carbazolyl group has is not particularly limited as long as the object of the present invention is not impaired. Preferred examples of the substituent which the carbazolyl group may have are the same as the examples of the substituent in the case where R ^c1 is the optionally substituted carbazolyl group.

In view of the reactivity of the compound represented by the formula (c1), as R ^c2 , the following formula (c2):

[Formula 7]

or the formula (c3):

[Formula 8]

A group represented by

In formula (c2), R ^c6 and R ^c7 are each a monovalent organic group, and b is 0 or 1. In formula (c3), R ^c8 is a group selected from the group consisting of a monovalent organic group, an amino group, a halogen, a nitro group, and a cyano group, A is S or O, and c is an integer of 0-4.

R ^c6 in formula (c2) can be selected from various organic groups within the range which does not impair the objective of this invention. Preferred examples of R ^c6 include a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a saturated aliphatic acyl group having 2 to 20 carbon atoms, and an alkoxycarbonyl group having 2 to 20 carbon atoms. , a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a substituent The naphthoyl group which may have, the naphthoxycarbonyl group which may have a substituent, a C11-C20 naphthylalkyl group which may have a substituent, the heterocyclyl group which may have a substituent, and the heterocyclyl which may have a substituent. A carbonyl group etc. are mentioned.

In R ^c6 , an alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and an ethyl group is particularly preferable.

R ^c7 in the formula (c2) is not particularly limited as long as the object of the present invention is not impaired, and can be selected from various organic groups. Specific examples of the group preferable as R ^c7 include a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an optionally substituted phenyl group, an optionally substituted naphthyl group, and an optionally substituted heterocyclyl group. have. As R ^c7 , among these groups, a phenyl group which may have a substituent and a naphthyl group which may have a substituent are more preferable, and a 2-methylphenyl group and a naphthyl group are particularly preferable.

Examples of the substituent when the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c6 or R ^c7 further have a substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a carbon atom. A monoalkylamino group having a saturated aliphatic acyl group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, the number of carbon atoms. and a dialkylamino group having an alkyl group of 1 to 6, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c6 or R ^c7 further have a substituent, the number of the substituents is not limited within a range that does not impair the object of the present invention, but preferably 1 to 4 do. When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c6 or R ^c7 have a plurality of substituents, the plurality of substituents may be the same or different.

When R ^c8 in the formula (c3) is an organic group, R ^c8 can be selected from various organic groups as long as the object of the present invention is not impaired. Preferred examples of when R ^c8 is an organic group in the formula (c3) include an alkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; a saturated aliphatic acyl group having 2 to 7 carbon atoms; an alkoxycarbonyl group having 2 to 7 carbon atoms; a C2-C7 saturated aliphatic acyloxy group; phenyl group; naphthyl group; benzoyl group; naphthoyl group; a benzoyl group substituted with a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; monoalkylamino group which has a C1-C6 alkyl group; dialkylamino group which has a C1-C6 alkyl group; morpholin-1-yl group; piperazin-1-yl group; halogen ; nitro group; cyano group; 2-methylphenylcarbonyl group; 4-(piperazin-1-yl)phenylcarbonyl group; 4-(phenyl)phenylcarbonyl group is mentioned.

In R ^c8 , a benzoyl group; naphthoyl group; a benzoyl group substituted with a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; A nitro group is preferable and a benzoyl group; naphthoyl group; 2-methylphenylcarbonyl group; 4-(piperazin-1-yl)phenylcarbonyl group; A 4-(phenyl)phenylcarbonyl group is more preferable.

Moreover, in Formula (c3), the integer of 0-3 is preferable, as for c, the integer of 0-2 is more preferable, It is especially preferable that it is 0 or 1. When c is 1, it is preferable that the position at which R ^c8 is bonded is para to the hand at which the phenyl group to which R ^c8 is bonded is bonded to a sulfur atom.

R ^c3 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group which may have a substituent. In the case of the phenyl group which may have a substituent, the substituent which the phenyl group may have is the same as the case where R ^c1 is the phenyl group which may have a substituent. As R ^c3 , a methyl group, an ethyl group, or a phenyl group is preferable, and a methyl group or a phenyl group is more preferable.

When a is 0, the oxime ester compound represented by the said Formula (c1) is compoundable by the method demonstrated below, for example. First, the ketone compound represented by R ^c2 -CO-R ^c1 is oximeated with hydroxylamine to obtain the oxime compound represented by R ^c2 -(C=N-OH)-R ^c1 . Next, the obtained oxime compound is acylized with an acid halide represented by R ^c3 -CO-Hal (Hal represents halogen) or an acid anhydride represented by (R ^c3 CO) ₂ O, the formula (c1) wherein a is 0 The oxime ester compound represented by ) is obtained.

Moreover, when a is 1, the oxime ester compound represented by the said Formula (c1) is compoundable by the method demonstrated below, for example. First, a ketone compound represented by R ^c2 -CO-CH ₂ -R ^c1 is reacted with a nitrite ester in the presence of hydrochloric acid to obtain an oxime compound represented by R ^c2 -CO-(C=N-OH)-R ^c1 . Next, the obtained oxime compound is acylized with an acid halide represented by R ^c3 -CO-Hal (Hal represents halogen) or an acid anhydride represented by (R ^c3 CO) ₂ O, the formula (c1) wherein a is 1 The oxime ester compound represented by ) is obtained.

As a compound represented by the said formula (c1), the compound represented by a following formula (c4) is mentioned.

[Formula 9]

In the formula (c4), a, R ^c2 , and R ^c3 are as described above. R ^c9 is a group selected from the group consisting of a monovalent organic group, an amino group, a halogen, a nitro group, and a cyano group, and d is an integer of 0-4.

In the formula (c4), R ^c9 is not particularly limited as long as the object of the present invention is not impaired, and in the case of an organic group, it is appropriately selected from various organic groups. Preferred examples of R ^c9 include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, an optionally substituted phenyl group, an optionally substituted phenoxy group, and a substituent The benzoyl group which may have, the phenoxycarbonyl group which may have a substituent, the benzoyloxy group which may have a substituent, the phenylalkyl group which may have a substituent, the naphthyl group which may have a substituent, the naphthoxy group which may have a substituent, a substituent A naphthoyl group which may have a substituent, a naphthoxycarbonyl group which may have a substituent, a naphthoyloxy group which may have a substituent, a naphthylalkyl group which may have a substituent, a heterocyclyl group which may have a substituent, an amino group, 1 or 2 and an amino group substituted with an organic group of , a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When s is an integer of 2 to 4, R ^c9 may be the same or different. In addition, the carbon atom number of the substituent which a substituent further has is not included in the carbon atom number of a substituent.

When R ^c9 is an alkyl group, 1 to 20 carbon atoms are preferable, and 1 to 6 carbon atoms are more preferable. Further, when R ^c9 is an alkyl group, it may be linear or branched. Specific examples when R ^c9 is an alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an iso pentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, etc. are mentioned. Moreover, when R ^c9 is an alkyl group, the alkyl group may contain an ether bond (-O-) in the carbon chain. Examples of the alkyl group having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.

When R ^c9 is an alkoxy group, it preferably has 1 to 20 carbon atoms, more preferably 1 to 6 carbon atoms. In addition, when R ^c9 is an alkoxy group, it may be linear or branched. Specific examples when R ^c9 is an alkoxy group include a methoxy group, an ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group Period, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec-ox and tyloxy group, tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, and isodecyloxy group. In addition, when R ^c9 is an alkoxy group, the alkoxy group may contain an ether bond (-O-) in the carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include a methoxyethoxy group, an ethoxyethoxy group, a methoxyethoxyethoxy group, an ethoxyethoxyethoxy group, a propyloxyethoxyethoxy group, and A methoxypropyloxy group etc. are mentioned.

When R ^c9 is a cycloalkyl group or a cycloalkoxy group, 3 to 10 carbon atoms are preferable, and 3 to 6 carbon atoms are more preferable. Specific examples when R ^c9 is a cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Specific examples of the case where R ^c9 is a cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.

When R ^c9 is a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, it preferably has 2 to 20 carbon atoms, more preferably 2 to 7 carbon atoms. Specific examples when R ^c9 is a saturated aliphatic acyl group include acetyl group, propanoyl group, n-butanoyl group, 2-methylpropanoyl group, n-pentanoyl group, 2,2-dimethylpropanoyl group, n-hexa noyl group, n-heptanoyl group, n-octanoyl group, n-nonanoyl group, n-decanoyl group, n-undecanoyl group, n-dodecanoyl group, n-tridecanoyl group, n-tetradecanoyl group, n-pentadecanoyl group, n-hexadecanoyl group, etc. are mentioned. Specific examples when R ^c9 is a saturated aliphatic acyloxy group include acetyloxy group, propanoyloxy group, n-butanoyloxy group, 2-methylpropanoyloxy group, n-pentanoyloxy group, and 2,2-dimethylpropoxy group. Panoyloxy group, n-hexanoyloxy group, n-heptanoyloxy group, n-octanoyloxy group, n-nonanoyloxy group, n-decanoyloxy group, n-undecanoyloxy group, n-dodecanoyloxy group , n-tridecanoyloxy group, n-tetradecanoyloxy group, n-pentadecanoyloxy group, and n-hexadecanoyloxy group.

When R ^c9 is an alkoxycarbonyl group, 2 to 20 carbon atoms are preferable, and 2 to 7 carbon atoms are more preferable. Specific examples when R ^c9 is an alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, tert -Butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, sec-pentyloxycarbonyl group, tert-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl group, n-octyloxycarbonyl group, isooctyloxycarbonyl group , sec-octyloxycarbonyl group, tert-octyloxycarbonyl group, n-nonyloxycarbonyl group, isononyloxycarbonyl group, n-decyloxycarbonyl group, and isodecyloxycarbonyl group.

When R ^c9 is a phenylalkyl group, 7 to 20 carbon atoms are preferable, and 7 to 10 carbon atoms are more preferable. Moreover, when R<^c9> is a naphthylalkyl group, C11-C20 is preferable, and C11-C14 is more preferable. Specific examples when R ^c9 is a phenylalkyl group include a benzyl group, a 2-phenylethyl group, a 3-phenylpropyl group, and a 4-phenylbutyl group. Specific examples when R ^c9 is a naphthylalkyl group include an α-naphthylmethyl group, a β-naphthylmethyl group, a 2-(α-naphthyl)ethyl group, and a 2-(β-naphthyl)ethyl group. . When R ^c9 is a phenylalkyl group or a naphthylalkyl group, R ^c9 may further have a substituent on the phenyl group or the naphthyl group.

When R ^c9 is a heterocyclyl group, the heterocyclyl group is a 5-membered or 6-membered monocyclic ring containing at least one N, S, O, or a heterocyclyl group in which these monocyclic rings are condensed with a benzene ring. When the heterocyclyl group is a condensed ring, it is assumed that the number of rings is up to 3. Heterocyclic rings constituting such a heterocyclyl group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, Pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzoimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, and quinoxaline; and the like. When R ^c9 is a heterocyclyl group, the heterocyclyl group may further have a substituent.

When R ^c9 is an amino group substituted with an organic group of 1 or 2, preferred examples of the organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a saturated aliphatic group having 2 to 20 carbon atoms. an acyl group, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoyl group which may have a substituent, A C11-C20 naphthylalkyl group which may have a substituent, a heterocyclyl group, etc. are mentioned. Specific examples of these preferred organic groups are the same as those of R ^c9 . Specific examples of the amino group substituted with 1 or 2 organic groups include methylamino group, ethylamino group, diethylamino group, n-propylamino group, di-n-propylamino group, isopropylamino group, n-butylamino group, di-n- Butylamino group, n-pentylamino group, n-hexylamino group, n-heptylamino group, n-octylamino group, n-nonylamino group, n-decylamino group, phenylamino group, naphthylamino group, acetylamino group, propanoylamino group, n- Butanoylamino group, n-pentanoylamino group, n-hexanoylamino group, n-heptanoylamino group, n-octanoylamino group, n-decanoylamino group, benzoylamino group, α-naphthoylamino group, and β-naphthoylamino group, etc. can be heard

Examples of the substituent when the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c9 further have a substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and 2 to carbon atoms. A monoalkylamino group having a saturated aliphatic acyl group of 7, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, an alkyl group having 1 to 6 carbon atoms, 1 to 6 carbon atoms and a dialkylamino group having an alkyl group of , a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c9 further have a substituent, the number of the substituents is not limited within a range that does not impair the object of the present invention, but preferably 1-4. When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c9 have a plurality of substituents, the plurality of substituents may be the same or different.

In R ^c9 , it is chemically stable, there are few steric hindrances, and the synthesis|combination of an oxime ester compound is easy, etc., A C1-C6 alkyl group, a C1-C6 alkoxy group, and a C2 The group selected from the group which consists of a saturated aliphatic acyl group of -7 is preferable, C1-C6 alkyl is more preferable, and a methyl group is especially preferable.

The position at which R ^c9 is bonded to the phenyl group is 4 when, with respect to the phenyl group to which R ^c9 is bonded, the bonding hand of the phenyl group and the main skeleton of the oxime ester compound is at position 1 and the position of the methyl group is at position 2, Position or position 5 is preferable, and position 5 is more preferable. Moreover, the integer of 0-3 is preferable, as for d, the integer of 0-2 is more preferable, 0 or 1 is especially preferable.

R ^c3 in the formula (c4) is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group which may have a substituent. Specific examples of R ^c3 are as described above for formula (c1). As R ^c3 in formula (c4), a methyl group, an ethyl group, and a phenyl group are preferable, and a methyl group and a phenyl group are more preferable.

Among oxime ester compounds, the following compounds are mentioned as a preferable example of the compound contained in Formula (c1) but not contained in Formula (c4).

[Formula 10]

Moreover, as a compound especially preferable among the oxime ester compounds represented by Formula (c4) especially preferable as an oxime ester compound, the compound of a following formula is mentioned.

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

When an oxime ester compound is contained as (C) a photoinitiator, the oxime ester compound demonstrated above may be used independently, may be used in combination of 2 or more types, You may use it in combination with photoinitiators other than an oxime ester compound. .

It is preferable that it is 1-20 mass % with respect to solid content of the photosensitive resin composition, and, as for content of the (C) photoinitiator in the photosensitive resin composition, it is more preferable that it is 1-10 mass %. In this case, when there is too little content of (C) photoinitiator, there exists a possibility that hardening by exposure may become inadequate, on the other hand, when there is too much, there exists a tendency for the formed colored layer to become easy to peel from a glass substrate at the time of image development.

<(D) compound represented by formula (1)>

The photosensitive resin composition contains the compound represented by (D) following formula (1). The photosensitive resin composition WHEREIN: The brightness|luminance of the color filter formed using the photosensitive resin composition improves by using together the chromatic (E) coloring agent mentioned later, and the compound represented by (D) Formula (1).

[Formula 18]

(In formula (1), R ¹ is a hydrogen atom or an alkyl group, R ² is an aromatic group which may have a substituent, R ³ is an alkylene group which may have a substituent, R ⁴ is a halogen atom, a hydroxyl group, or a mercap an earthenware group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphonato group, or an organic group, and n is an integer of 0 to 3.)

In Formula (1), R< ¹ > is a hydrogen atom or an alkyl group. When R ¹ is an alkyl group, the alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group. Although the number of carbon atoms of the said alkyl group is not specifically limited, 1-20 are preferable, 1-10 are preferable, and 1-5 are more preferable.

Specific examples of the alkyl group preferable as R ¹ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopene Tyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethyl-n-hexyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group , n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, and n-icosyl group. can

In Formula (1), R< ² > is the aromatic group which may have a substituent. The aromatic hydrocarbon group which may have a substituent may be sufficient as the aromatic group which may have a substituent, and the aromatic heterocyclic group which may have a substituent may be sufficient as it.

The kind of aromatic hydrocarbon group is not specifically limited in the range which does not impair the objective of this invention. The aromatic hydrocarbon group may be a monocyclic aromatic group, may be formed by condensing two or more aromatic hydrocarbon groups, or may be formed by bonding two or more aromatic hydrocarbon groups by a single bond. As an aromatic hydrocarbon group, a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, and a phenanthrenyl group are preferable.

The kind of aromatic heterocyclic group is not specifically limited in the range which does not impair the objective of this invention. The aromatic heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the aromatic heterocyclic group include a pyridyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, a thiazolyl group, an isoxazolyl group, an isothiazolyl group, a benzoxazolyl group, and a benzothiazolyl group. group, and a benzimidazolyl group are preferred.

Examples of the substituent which the phenyl group, polycyclic aromatic hydrocarbon group, or aromatic heterocyclic group may have include a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfino group, and a sulfonyl group. an agar, a sulfonato group, a phosphino group, a phosphinyl group, a phosphono group, a phosphonato group, an amino group, an ammonia group, and an organic group are mentioned. When a phenyl group, a polycyclic aromatic hydrocarbon group, or an aromatic heterocyclic group has a plurality of substituents, the plurality of substituents may be the same or different.

When the substituent which the aromatic group has is an organic group, an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, etc. are mentioned as the said organic group. The organic group may contain a bond or a substituent other than a hydrocarbon group such as a hetero atom in the organic group. Moreover, any of linear, branched, and cyclic|annular form may be sufficient as this organic group. This organic group is usually monovalent, but may be a divalent or higher organic group in the case of forming a cyclic structure.

When the aromatic group has a substituent on an adjacent carbon atom, two substituents bonded on the adjacent carbon atom may combine with each other to form a cyclic structure. Examples of the cyclic structure include an aliphatic hydrocarbon ring and an aliphatic ring containing a hetero atom.

When the substituent possessed by the aromatic group is an organic group, the bond contained in the organic group is not particularly limited as long as the effect of the present invention is not impaired, and the organic group is a bond containing a hetero atom such as an oxygen atom, a nitrogen atom, or a silicon atom. may contain Specific examples of the bond containing a hetero atom include an ether bond, a thioether bond, a carbonyl bond, a thiocarbonyl bond, an ester bond, an amide bond, a urethane bond, an imino bond (-N=C(-R)- , -C(=NR)-: R represents a hydrogen atom or an organic group), a carbonate bond, a sulfonyl bond, a sulfinyl bond, an azo bond, and the like.

As a bond containing the hetero atom which an organic group may have, an ether bond, a thioether bond, a carbonyl bond, a thiocarbonyl bond, an ester bond, an amide bond from a heat resistant viewpoint of the imidazole compound represented by Formula (1) , amino bond (-NR-: R represents a hydrogen atom or a monovalent organic group) urethane bond, imino bond (-N=C(-R)-, -C(=NR)-: R is a hydrogen atom or 1 valent organic group), a carbonate bond, a sulfonyl bond, and a sulfinyl bond are preferable.

When an organic group is a substituent other than a hydrocarbon group, the kind of substituents other than a hydrocarbon group is not specifically limited in the range which does not impair the objective of this invention. Specific examples of the substituent other than the hydrocarbon group include a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a cyano group, an isocyano group, a cyanato group, an isocyanato group, a thiocyanato group, an isothiocyanato group. , silyl group, silanol group, alkoxy group, alkoxycarbonyl group, amino group, monoalkylamino group, dialkylaluminum group, monoarylamino group, diarylamino group, carbamoyl group, thiocarbamoyl group, nitro group, nitroso group, carboxylate group, acyl group, acyloxy group, sulfino group, sulfonato group, phosphino group, phosphinyl group, phosphonato group, alkyl ether group, alkenyl ether group, alkylthioether group, alkenylthioether group, aryl An ether group, an arylthio ether group, etc. are mentioned. The hydrogen atom contained in the said substituent may be substituted by the hydrocarbon group. Further, the hydrocarbon group contained in the substituent may be any of linear, branched, and cyclic.

Examples of the substituent included in the phenyl group, polycyclic aromatic hydrocarbon group, or aromatic heterocyclic group include an alkyl group having 1 to 12 carbon atoms, an aryl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and number of carbon atoms. A 1-12 aryloxy group, a C1-C12 arylamino group, and a halogen atom are preferable.

As R ² , the imidazole compound represented by the formula (1) can be synthesized inexpensively and easily, and the solubility of the imidazole compound to water or an organic solvent is good, so the phenyl group and furyl group which may have a substituent, respectively. , a thienyl group is preferred.

In Formula (1), R< ³ > is the alkylene group which may have a substituent. The substituent which the alkylene group may have is not specifically limited in the range which does not impair the objective of this invention. Specific examples of the substituent which the alkylene group may have include a hydroxyl group, an alkoxy group, an amino group, a cyano group, and a halogen atom. A linear alkylene group may be sufficient as an alkylene group, and a branched chain alkylene group may be sufficient as it, and a linear alkylene group is preferable. Although carbon atom number of an alkylene group is not specifically limited, 1-20 are preferable, 1-10 are preferable, and 1-5 are more preferable. In addition, the carbon atom of the substituent couple|bonded with the alkylene group is not included in the carbon atom number of an alkylene group.

A straight-chain alkoxy group or a branched-chain alkoxy group may be sufficient as the alkoxy group as a substituent couple|bonded with an alkylene group. Although the number of carbon atoms of the alkoxy group as a substituent is not specifically limited, 1-10 are preferable, 1-6 are more preferable, 1-3 are especially preferable.

A monoalkylamino group or a dialkylamino group may be sufficient as the amino group as a substituent couple|bonded with an alkylene group. A linear alkyl group or a branched chain alkyl group may be sufficient as the alkyl group contained in a monoalkylamino group or a dialkylamino group. Although the number of carbon atoms of the alkyl group contained in a monoalkylamino group or a dialkylamino group is not specifically limited, 1-10 are preferable, 1-6 are more preferable, 1-3 are especially preferable.

Specific examples of the alkylene group preferable as R ³ include methylene group, ethane-1,2-diyl group, n-propane-1,3-diyl group, n-propane-2,2-diyl group, n-butane- 1,4-diyl group, n-pentane-1,5-diyl group, n-hexane-1,6-diyl group, n-heptane-1,7-diyl group, n-octane-1,8-diyl group , n-nonane-1,9-diyl group, n-decane-1,10-diyl group, n-undecane-1,11-diyl group, n-dodecane-1,12-diyl group, n-tri Decane-1,13-diyl group, n-tetradecane-1,14-diyl group, n-pentadecane-1,15-diyl group, n-hexadecane-1,16-diyl group, n-heptadecane- 1,17-diyl group, n-octadecane-1,18-diyl group, n-nonadecan-1,19-diyl group, and n-icosan-1,20-diyl group are mentioned.

R ⁴ is a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphonato group, or an organic group, n is an integer of 0 to 3. When n is an integer of 2-3, some R< ⁴ > may be same or different, respectively.

When R ⁴ is an organic group, the organic group is the same as the organic group which the aromatic group may have as a substituent with respect to R ² .

When R ⁴ is an organic group, the organic group is preferably an alkyl group, an aromatic hydrocarbon group, and an aromatic heterocyclic group. As an alkyl group, a C1-C8 linear or branched alkyl group is preferable, and a methyl group, an ethyl group, n-propyl group, and an isopropyl group are more preferable. As the aromatic hydrocarbon group, a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, and a phenanthrenyl group are preferable, a phenyl group and a naphthyl group are more preferable, and a phenyl group is particularly preferable. Examples of the aromatic heterocyclic group include a pyridyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, a thiazolyl group, an isoxazolyl group, an isothiazolyl group, a benzoxazolyl group, and a benzothiazolyl group. A group and a benzimidazolyl group are preferable, and a furyl group and a thienyl group are more preferable.

When R ⁴ is an alkyl group, the bonding position of the alkyl group on the imidazole ring is preferably at the 2-position, the 4-position, or the 5-position, and more preferably the 2-position. When R ⁴ is an aromatic hydrocarbon group or an aromatic heterocyclic group, the bonding position of these groups on imidazole is preferably at the 2-position.

Among the imidazole compounds represented by the formula (1), a compound represented by the following formula (1-1) is preferable, from the viewpoint of being inexpensive and easily synthesizable and having excellent solubility in water and organic solvents, 1-1) and R ³ is more preferably a methylene group.

[Formula 19]

(In formula (1-1), R ¹ , R ³ , R ⁴ and n are the same as in Formula (1), and R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen Atom, hydroxyl group, mercapto group, sulfide group, silyl group, silanol group, nitro group, nitroso group, sulfino group, sulfo group, sulfonato group, phosphino group, phosphinyl group, phosphono group, phosphonato group , an amino group, an ammonia group, or an organic group, provided that at least one of R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ is a group other than a hydrogen atom)

When R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are an organic group, the organic group is the same as the organic group that R ² in Formula (1) has as a substituent. R ⁵ , R ⁶ , R ⁷ and R ⁸ are preferably hydrogen atoms from the viewpoint of solubility of the imidazole compound in a solvent.

Among them, it is preferable that at least one of R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ is the following substituent, and it is particularly preferable that R ⁹ is the following substituent. When R ⁹ is the following substituent, R ⁵ , R ⁶ , R ⁷ and R ⁸ are preferably a hydrogen atom.

-OR ¹⁰

(R ¹⁰ is a hydrogen atom or an organic group)

When R< ¹⁰ > is an organic group, the said organic group is the same as the organic group which R< ² > in Formula (1) has as a substituent. As R ¹⁰ , an alkyl group is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, an alkyl group having 1 to 3 carbon atoms is particularly preferable, and a methyl group is most preferable.

Among the compounds represented by the formula (1-1), a compound represented by the following formula (1-1-1) is preferable.

[Formula 20]

(In Formula (1-1-1), R ¹ , R ⁴ and n are the same as in Formula (1), and R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are each independently a hydrogen atom or a hydroxyl group. , mercapto group, sulfide group, silyl group, silanol group, nitro group, nitroso group, sulfino group, sulfo group, sulfonato group, phosphino group, phosphinyl group, phosphono group, phosphonato group, amino group, an ammony group or an organic group, provided that at least one of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ is a group other than a hydrogen atom)

Among the compounds represented by formula (1-1-1), it is preferable that at least one of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ is a group represented by the above-mentioned -OR ¹⁰ , and R ¹⁵ is -OR ¹⁰ It is especially preferable that it is a group which represents. When R ¹⁵ is a group represented by -OR ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are preferably hydrogen atoms.

The synthesis method of the imidazole compound represented by said Formula (1) is not specifically limited. For example, by reacting a halogen-containing carboxylic acid derivative represented by the following formula (I) with an imidazole compound represented by the following formula (II) according to a conventional method to perform imidazolylation, the formula (1) The imidazole compound represented by ) can be synthesize|combined.

[Formula 21]

(In formulas (I) and (II), R ¹ , R ² , R ³ , R ⁴ and n are the same as in formula (1). In formula (I), Hal is a halogen atom.)

In addition, when the imidazole compound is a compound represented by the formula (1) and R ³ is a methylene group, that is, when the imidazole compound is a compound represented by the following formula (1-2), the Michael addition reaction described below The imidazole compound can also be synthesized by the method according to

[Formula 22]

(in formula (1-2), R ¹ , R ² , R ⁴ and n are the same as in formula (1))

Specifically, for example, the 3-substituted acrylic acid derivative represented by the following formula (III) and the imidazole compound represented by the formula (II) are mixed in a solvent to cause a Michael addition reaction, whereby the formula (1-2) The imidazole compound represented by ) is obtained.

[Formula 23]

(in formula (III), R ¹ , R ² , R ⁴ and n are the same as in formula (1))

Moreover, the imidazole compound represented by following formula (1-3) is obtained by adding the 3-substituted acrylic acid derivative containing the imidazolyl group represented by following formula (IV) to the solvent containing water.

[Formula 24]

(in formulas (IV) and (1-3), R ² , R ⁴ and n are the same as in formula (1))

In this case, the imidazole compound represented by the formula (II) and the 3-substituted acrylic acid represented by the following formula (V) are produced by hydrolysis of the 3-substituted acrylic acid derivative represented by the formula (IV). Then, a Michael addition reaction occurs between the 3-substituted acrylic acid represented by the following formula (V) and the imidazole compound represented by the formula (II) to produce an imidazole compound represented by the formula (1-3).

[Formula 25]

(in formula (V), R ² is the same as that of formula (1))

The following are mentioned as a preferable specific example of the imidazole compound represented by Formula (1).

[Formula 26]

In this invention, the compound represented by the said Formula (1) can be used individually or in mixture of 2 or more types.

Moreover, it is preferable that it is 1-100 mass parts with respect to 100 mass parts of said photoinitiators, and, as for content of the compound represented by said Formula (1), it is more preferable that it is 5-50 mass parts. By using the compound represented by the said Formula (1) in such a range, the brightness|luminance of the display element provided with the color filter formed using the photosensitive resin composition improves easily.

<(E) Colorant>

The photosensitive resin composition contains a chromatic (E) coloring agent. A display element capable of displaying a color image can be obtained by forming a color filter by combining different kinds of colors selected from chromatic colors. (D) The luminance of the display element provided with the color filter formed using the photosensitive resin composition improves by mix|blending with the photosensitive resin composition combining the compound and chromatic (E) coloring agent of Formula (1).

Examples of the color filters that have been widely used conventionally include a primary color filter of RGB (red, green, blue) and a filter of a complementary color system of CMYG (cyan, magenta, yellow, green) system.

(E) As a coloring agent, the point of the light resistance of a color filter and a weather resistance to an organic pigment is preferable. Although the organic pigment is not particularly limited, for example, a compound classified as a pigment in the color index (C.I.; issued by The Society of Dyers and Colorists), specifically, the color index ( C. I.) It is preferable to use the numbered ones.

Moreover, (E) coloring agent may contain a small amount of achromatic coloring agents, such as black and white, for the purpose of hue adjustment.

C. I. Pigment Yellow 1 (hereinafter, "C. I. Pigment Yellow" is the same and only the numbers are described), 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 86, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175, 180, 185;

C. I. Pigment Orange 1 (hereinafter, "C. I. Pigment Orange" is the same, and only the numbers are described), 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 55, 59, 61, 63, 64, 71, 73;

C. I. Pigment Violet 1 (hereinafter, “C. I. Pigment Violet” is the same and only numbers are described), 19, 23, 29, 30, 32, 36, 37, 38, 39, 40, 50;

C. I. Pigment Red 1 (hereinafter, “C. I. Pigment Red” is the same and only the numbers are described), 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 40, 41, 42, 48: 1, 48: 2, 48: 3, 48: 4, 49: 1, 49 : 2, 50 : 1, 52 : 1, 53 : 1, 57, 57 : 1, 57 : 2, 58 : 2, 58 : 4, 60 : 1, 63 : 1, 63 : 2, 64 : 1, 81: 1, 83, 88, 90: 1, 97, 101, 102, 104, 105, 106, 108, 112, 113, 114, 122, 123, 144, 146, 149, 150, 151, 155, 166, 168, 170, 171, 172, 174, 175, 176, 177, 178, 179, 180, 185, 187, 188, 190, 192, 193, 194, 202, 206, 207, 208, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 242, 243, 245, 254, 255, 264, 265;

C. I. Pigment Blue 1 (hereinafter, “C. I. Pigment Blue” is the same and only numbers are described), 2, 15, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 66;

C. I. Pigment Green 7, C. I. Pigment Green 36, C. I. Pigment Green 37, Pigment Green 58, Pigment Green 59, Pigment Green 60;

C. I. Pigment Brown 23, C. I. Pigment Brown 25, C. I. Pigment Brown 26, C. I. Pigment Brown 28;

C. I. Pigment Black 1, C. I. Pigment Black 7.

(E) The coloring agent may use dye. When a dye is used, it can be used alone, but it is more preferable to use it in combination with a pigment. As a dye which can be used, although solvent blue 35 is mentioned, for example, it is not limited to this.

(E) The colorant may be purified by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum superheating method, or a combination thereof.

It is preferable that content of (E) coloring agent in the photosensitive resin composition is 10-200 mass % with respect to solid content other than (E) coloring agent of the photosensitive resin composition from the point which forms the pixel excellent in transparency and color purity, and 50-150 It is more preferable that it is mass %.

Moreover, it is preferable to add (E) a coloring agent to the photosensitive resin composition, after setting it as the dispersion liquid disperse|distributed to the appropriate density|concentration using the dispersing agent. As a well-known dispersing agent, a polymer dispersing agent is preferable, For example, an acrylic copolymer dispersing agent, a polyurethane type dispersing agent, a polyester type dispersing agent, a polyethyleneimine type dispersing agent, a polyallylamine type dispersing agent, etc. are mentioned. Among them, a polyurethane-based dispersant is preferable. When these polymeric dispersants are used, the dispersibility and dispersion stability of the (E) colorant can be improved, and the color, contrast ratio, and heat resistance can be improved.

(D) the compound represented by the formula (1) is added to the dispersion together with the (E) colorant when preparing the dispersion liquid of (E) the colorant, and when preparing the photosensitive resin composition, (E) the dispersion liquid of the colorant or (E) You may mix|blend together with a coloring agent.

<(S) solvent>

The photosensitive resin composition can contain the (S) solvent. As a solvent, what is necessary is just to disperse|distribute or dissolve the compound represented by said (D) Formula (1), (E) a coloring agent, and other components mentioned later, and does not react with these components, and has moderate volatility.

Examples of the (S) solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and diethylene glycol monomethyl ether. Ethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl Ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n (poly)alkylene glycol monoalkyl ethers such as butyl ether, tripropylene glycol monomethyl ether, and tripropylene glycol monoethyl ether; (poly)alkylenes such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate glycol monoalkyl ether acetates; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; Ketones, such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; lactic acid alkyl esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; 2-hydroxy-2-methylpropionate ethyl, 3-methoxymethylpropionate, 3-methoxyethylpropionate, 3-ethoxymethylpropionate, 3-ethoxypropionate ethyl, ethoxyethyl acetate, ethyl hydroxyacetate, 2 -Hydroxy-3-methylbutanoate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-acetic acid Butyl, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, acetoacetic acid other esters such as methyl, ethyl acetoacetate, and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; Amides, such as N-methylpyrrolidone, N,N- dimethylformamide, and N,N- dimethylacetamide, etc. are mentioned. These solvents can be used individually or in combination of 2 or more types.

Among the above solvents, propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 3- Methoxybutyl acetate is preferable because the dispersibility of the said (E) coloring agent can be made favorable while showing the outstanding solubility with respect to the compound represented by the said (D) Formula (1).

(S) As for content of a solvent, the quantity from which the total density|concentration of the total solid of the photosensitive resin composition will be 5-30 mass % is preferable from viewpoints, such as applicability|paintability of the photosensitive resin composition obtained, stability, etc., 10-20 mass % The amount to be is more preferable.

<(F) other components>

In addition to the component demonstrated above, the photosensitive resin composition may contain various additives as needed.

As an additive, For example, fillers, such as glass and an alumina; high molecular compounds such as polyvinyl alcohol and poly(fluoroalkyl acrylate); Surfactants, such as a fluorine-type surfactant and a silicone type surfactant; Vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl) -3-Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclo) Hexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. adhesion promoter; antioxidants such as 2,2-thiobis(4-methyl-6-t-butylphenol) and 2,6-di-t-butylphenol; UV absorbers such as 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole and alkoxybenzophenones; Aggregation inhibitors, such as sodium polyacrylate; Malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, 2-aminoethanol, 3-amino-1-propanol, 5-amino-1-pentanol, 3-amino-1,2-propane and residue improving agents such as diol, 2-amino-1,3-propanediol, and 4-amino-1,2-butanediol.

«The preparation method of the photosensitive resin composition»

The photosensitive resin composition can be prepared by an appropriate method. Specifically, a photosensitive resin composition is obtained by uniformly mixing the predetermined components described above in a desired amount, respectively. When preparing the photosensitive resin composition, (E) the colorant is uniformly dispersed in the photosensitive resin composition, for example, using a bead mill, a roll mill, etc., while pulverizing the (E) colorant, the raw material of the photosensitive resin is uniformly dispersed. You may mix.

According to the photosensitive resin composition prepared in this way, the color filter which provides the favorable display element of a brightness|luminance can be formed. A display element will not be specifically limited if a color filter is used, A liquid crystal display element, organic electroluminescent element, etc. are mentioned.

≪Pattern Forming Method≫

The pattern forming method according to the present invention comprises a step of applying the above-described photosensitive resin composition on a substrate to form a coating film, a step of positionally exposing the formed coating film according to the shape of a pattern, and a step of developing the exposed coating film includes

First, in the step of forming a coating film, on a substrate on which a patterned cured product is to be formed, a contact transfer coating device such as a roll coater, a reverse coater, or a bar coater, or a non-contact application device such as a spinner (rotary coating device) or a curtain flow coater The photosensitive resin composition is apply|coated using the type|mold coating apparatus. After application, if necessary, the solvent is removed by drying to form a coating film.

Next, active energy rays, such as an ultraviolet-ray and an excimer laser beam, are irradiated to a coating film through a negative mask, and a coating film is partially exposed according to the shape of a pattern. For exposure, a light source emitting ultraviolet rays such as a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a xenon lamp, or a carbon arc lamp can be used. Although the exposure amount changes also with the composition of the photosensitive resin composition, about 10-600 mJ/cm<2> is preferable, for example.

By developing the regioselectively exposed coating film with a developer, a cured product is formed. The developing method is not specifically limited, An immersion method, a spray method, etc. can be used. Specific examples of the developer include organic substances such as monoethanolamine, diethanolamine, and triethanolamine, and aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and quaternary ammonium salts.

Then, as needed, it post-baking to the insoluble part of the coating film after image development, and the pattern which consists of the hardened|cured photosensitive resin composition is formed. As for a post-baking, 15 to 60 minutes are preferable at 150-250 degreeC.

Thus, the pattern of the hardened|cured photosensitive resin composition formed is useful as a color filter in a display element, and provides the display element excellent in brightness|luminance.

Example

Hereinafter, the present invention will be described more specifically based on Examples, but the present invention is not limited to these Examples at all.

[Examples 1 to 4 and Comparative Examples 1 to 5]

<(A) component>

In the Example and the comparative example, the acrylic resin of a following formula was used as (A) alkali-soluble resin. The mass average molecular weight of the acrylic resin of the following formula is 8000. The number at the lower right of each structural unit in the following formula is the molar ratio of each structural unit in all the structural units constituting the acrylic resin.

[Formula 27]

<(B) component>

In Examples and Comparative Examples, dipentaerythritol hexaacrylate was used as the photopolymerizable monomer (B).

<(C) component>

In Examples and Comparative Examples, (C) as the photopolymerization initiator, a compound of the following formula was used.

[Formula 28]

<(D) component or (D') component>

In the Examples, (D) As the compound represented by the formula (1), a compound of the following formula D-1 was used. In the comparative example, (D) a compound of the following formula D'-1 was used as the component (D'), which is a compound similar to the compound represented by the formula (1). The compound of Formula D-1 below was synthesized according to Synthesis Example 1 below.

[Formula 29]

[Synthesis Example 1]

Compound D-1 was synthesized according to the following method.

First, 30 g of a cinnamic acid derivative having a structure of the following formula was dissolved in 200 g of methanol, and then 7 g of potassium hydroxide was added to methanol. Then, the methanol solution was stirred at 40 degreeC. Methanol was distilled off, and the residue was suspended in 200 g of water. 200 g of tetrahydrofuran was mixed and stirred with the obtained suspension, and the aqueous phase was liquid-separated. After adding and stirring 4 g of hydrochloric acid under ice cooling, 100 g of ethyl acetate was mixed and stirred. After allowing the liquid mixture to stand still, the oil phase was fractionated. The target substance was crystallized from the oil phase, the precipitate was collect|recovered, and the imidazole compound (D-1) of the said structure was obtained.

[Formula 30]

The measurement result of < ¹ >H-NMR of the imidazole compound (D-1) of the said structure is as follows.

<(E) component>

In the Example and the comparative example, the following E-1 to E-6 were used as (E) coloring agent.

[Formula 31]

<Preparation of the photosensitive resin composition>

In Examples 1-4 and Comparative Example 1, (A) 100 parts by mass of alkali-soluble resin, (B) 60 parts by mass of a photopolymerizable monomer, (C) 14.8 parts by mass of a photoinitiator, and Table 1 Dispersion containing 3.2 parts by mass of component (D) or component (D') of the kind and (E) colorant of the kind shown in Table 1 (colorant concentration of 12 mass%, dispersant concentration of 4.2 mass%, solvent: propylene glycol monomethyl After mixing 81.8 mass parts of ether acetate) uniformly, it diluted to 15 mass % of solid content concentration with a solvent, and the photosensitive resin composition was obtained. As the solvent for dilution, a mixed solvent of propylene glycol monomethyl ether acetate (PM)/3-methoxybutyl acetate (MA)/cyclohexanone (AN) was used. The composition of the mixed solvent was PM/MA/AN = 75/10/15 as a mass ratio.

In Comparative Examples 2-5, except not using the (D)component or (D')component, it carried out similarly to Examples 1-4 and the comparative example 1, and obtained the photosensitive resin composition.

Using the obtained photosensitive resin composition, according to the method mentioned later, the hardened|cured colored film was formed, and the brightness|luminance of the colored film was evaluated.

<Luminance evaluation 1>

On the glass substrate of thickness 0.7mm, the photosensitive resin composition was apply|coated using the spin coater. Then, the coating film was heated on an 80 degreeC hotplate for 2 minutes. A cured colored film having a thickness of 2.0 µm was obtained by irradiating the coating film with ultraviolet rays of 1000 mJ/cm 2 using an ultra-high pressure mercury lamp. About the obtained colored film, using the color analyzer (MCPD2000 by Otsuka Electronics Co., Ltd.), the chromaticity coordinate value (x, y) in the CIE color space system was measured with C light source and 2 degree field of view. From the measurement results, the luminance (stimulus value Y) at the chromaticity coordinate values x shown in Table 1 was determined.

About each Example and Comparative Example, the brightness ratio of the colored film was calculated|required as follows, and the brightness|luminance of the coating film formed using the photosensitive resin composition containing (D)component or (D') component was evaluated. The case where the luminance ratio was more than 100% was determined as (circle), and the case where the luminance ratio was 100% or less was determined as x.

In addition, about Comparative Examples 2-5, and Comparative Example 7, since it was a reference|standard for calculating a luminance ratio, luminance evaluation was not implemented.

(Luminance ratio calculation formula)

Example 1: Luminance of Example 1 / Luminance of Comparative Example 2 × 100

Comparative Example 1: Luminance of Comparative Example 1 / Luminance of Comparative Example 2 × 100

Example 2: Luminance of Example 2 / Luminance of Comparative Example 3 × 100

Example 3: Luminance of Example 3 / Luminance of Comparative Example 4 × 100

Example 4: Luminance of Example 4 / Luminance of Comparative Example 5 × 100

<Luminance evaluation 2>

Except for baking the cured colored film after exposure at 230 degreeC for 140 minute(s), the brightness|luminance of the baked colored film was evaluated similarly to brightness evaluation 1 by brightness ratio.

<Luminance evaluation 3>

Except for baking the cured colored film after exposure at 250 degreeC for 140 minute(s), the brightness|luminance of the baked colored film was evaluated similarly to brightness evaluation 1 by brightness ratio.

According to the comparison of Example 1 and Comparative Example 2, the comparison of Example 2 and Comparative Example 3, the comparison of Example 3 and Comparative Example 4, and the comparison of Example 4 and Comparative Example 5, the photosensitive resin composition of the chromatic ( E) Coloring agent and (D) When containing the compound represented by Formula (1), the luminance of the colored film formed using the photosensitive resin composition does not contain the compound represented by (D) Formula (1) The photosensitive resin composition It can be seen that the luminance of the colored film formed using

According to Comparative Example 1, (D) instead of D-1, which is a compound represented by the formula (1), a nitrogen-containing organic compound similar to D-1, but containing compound D'-1 which does not contain an imidazole skeleton. Even if it forms a colored film using the photosensitive resin composition, it turns out that the effect of the brightness improvement with respect to the colored film formed using the photosensitive resin composition of the comparative example 2 is not observed.

From Examples 1 to 4, when the photosensitive resin composition contains the chromatic (E) coloring agent and (D) the compound represented by the formula (1), it can be seen that the effect of improving the luminance is obtained regardless of the color of the coloring agent. have.

Claims (4)

The photosensitive resin composition containing (A) alkali-soluble resin, (B) photopolymerizable monomer, (C) photoinitiator, (D) compound represented by following formula (1), and chromatic (E) coloring agent.
[Formula 1]

(In formula (1), R ¹ is a hydrogen atom or an alkyl group, R ² is an aromatic group which may have a substituent, R ³ is an alkylene group which may have a substituent, R ⁴ is a halogen atom, a hydroxyl group, or a mercap an earthenware group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphonato group, or an organic group, and n is an integer of 0 to 3) A step of applying the photosensitive resin composition according to claim 1 on a substrate to form a coating film;
a step of positionally selectively exposing the coating film;
A method of forming a pattern including a step of developing the exposed coating film. A color filter provided with the colored layer formed using the photosensitive resin composition of Claim 1. A display element provided with the color filter of Claim 3.