KR20140067913A - Photosensitive resin composition - Google Patents

Abstract

Provided in the present invention is a photosensitive resin composition comprising a binder resin (A), a polymerizable compound (B), a polymerizable initiator (C), an extender pigment (D), and a solvent (E), wherein the solvent (E) comprises 70-99 wt% of a solvent (E1) having 8.0-9.1 (cal/cm^3)^1/2 of the solubility parameter and 1-30 wt% of a solvent (E2) having 9.2-11.0 (cal/cm^3)^1/2 of the solubility parameter.

Description

[0001] PHOTOSENSITIVE RESIN COMPOSITION [0002]

The present invention relates to a photosensitive resin composition.

A pattern such as a color filter used in a display device such as a liquid crystal display panel, an electroluminescence panel, a plasma display panel, or an electronic paper is manufactured using a photosensitive resin composition. Specifically, a pattern is formed by applying a photosensitive resin composition on a substrate, followed by drying, selectively exposing the obtained dried film, and then developing.

As such a photosensitive resin composition, for example, Japanese Patent Laid-Open Publication No. 2011-221310 discloses a photosensitive resin composition comprising a binder resin, a polymerizable compound, a polymerization initiator, an extender pigment and a solvent, wherein the solvent is propylene glycol monomethyl An example using ether acetate is described.

The dry film obtained from the conventional photosensitive resin composition can not necessarily satisfy the low tackiness and the pattern obtained from the conventional photosensitive resin composition can not necessarily satisfy its hardness There was a case.

In order to solve the above problems, the present invention provides the following [1].

[1] A photosensitive resin composition comprising a binder resin (A), a polymerizable compound (B), a polymerization initiator (C), an extender pigment (D) and a solvent (E) 8.0 ~ 9.1 (cal / ㎤) 1/2 of the solvent (E1), the solvent (E) with respect to, and including 70 to 99% by weight, the solubility parameter is 9.2 ~ 11.0 (cal / ㎤) 1/2 of the solvent (E2) is contained in an amount of 1 to 30 mass% with respect to the solvent (E).

Further, the present invention provides the following [2] to [10].

[2] The photosensitive resin composition according to [1], wherein the polymerization initiator (C) is an oxime compound.

[3] The photosensitive resin composition according to [1] or [2], wherein the acid value of the binder resin (A) is 50 to 180 mg-KOH / g.

[4] The toner according to any one of [1] to [3], wherein the content of the binder resin (A) is 30 to 80 parts by mass relative to 100 parts by mass of the total amount of the binder resin (A) and the polymerizable compound (B) Wherein the photosensitive resin composition is a photosensitive resin composition.

[5] The photosensitive resin composition according to any one of [1] to [4], wherein the extender pigment (D) is silicon oxide.

[6] The photosensitive resin composition according to any one of [1] to [5], further comprising a colorant.

[7] The photosensitive resin composition according to [6], wherein the colorant is a colorant containing a pigment.

[8] The photosensitive resin composition according to [6] or [7], wherein the colorant is a colorant containing a dye.

[9] A pattern formed by the photosensitive resin composition according to any one of [1] to [8].

[10] A display device comprising a pattern according to [9].

INDUSTRIAL APPLICABILITY According to the present invention, it becomes possible to provide a photosensitive resin composition which gives a dry film having satisfactory low tackiness and which gives a pattern having satisfactory hardness.

The photosensitive resin composition of the present invention contains a binder resin (A), a polymerizable compound (B), a polymerization initiator (C), an extender pigment (D) and a solvent (E).

The binder resin (A) contains an unsaturated compound (b) having an epoxy group (hereinafter also referred to as " unsaturated compound (b) ") in an addition polymer (a) having a structural unit derived from an unsaturated carboxylic acid (B) ") is reacted with the binder resin (A).

(a2) having an unsaturated bond capable of addition-polymerizable addition with (a1) (hereinafter referred to as " (a2) " ) &Quot;) may be mentioned as an addition polymer.

(a1) include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid and p-vinylbenzoic acid;

Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;

5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept- 5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] hept- [2.2.1] hept-2-ene, and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;

(Meth) acryloyloxyalkyl (meth) acrylate of a divalent or higher polyvalent carboxylic acid such as mono [2- (meth) acryloyloxyethyl] succinate, mono [2- ] Esters;

and unsaturated compounds containing a hydroxyl group and a carboxyl group in the same molecule such as? - (hydroxymethyl) acrylic acid.

Of these, (meth) acrylic acid is preferably used in terms of copolymerization reactivity and alkali solubility.

In the present specification, the term "(meth) acrylic acid" means at least one kind selected from the group consisting of acrylic acid and methacrylic acid. Quot ;, " (meth) acryloyl ", and " (meth) acrylate "

(meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec- Alkyl acrylate esters;

Cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate (referred to in the art as dicyclo (Meth) acrylate cyclic alkyl esters such as dicyclopentanyloxyethyl (meth) acrylate and isobornyl (meth) acrylate;

Aryl (meth) acrylates or aralkyl esters such as phenyl (meth) acrylate and benzyl (meth) acrylate;

Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;

Hydroxyalkyl esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;

2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] (2'-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] hept- Ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept- 2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept- Cyclohexyl [2.2.1] hept-2-ene, 5,6-bis 2,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene and the like such as bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept- Cyclo-unsaturated compounds;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N- Dicarbonylimide derivatives such as N-succinimidyl-3-maleimidepropionate and N- (9-acridinyl) maleimide;

And examples thereof include styrene,? -Methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, Vinyl, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and the like.

(a2) is a compound having at least one skeleton selected from the group consisting of a tricyclodecane skeleton and a tricyclodecene skeleton and a compound (a2-1) having an ethylenically unsaturated bond [hereinafter referred to as "(a2-1)" ). (a2-1), it is possible to suppress film reduction of the pattern due to development.

Herein, the terms "tricyclodecane skeleton" and "tricyclodecene skeleton" in the present specification mean the following structures (each of which is an arbitrary position of the bond (bond)).

(meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, . These may be used alone or in combination of two or more.

(b-1) (hereinafter may be referred to as "(b-1)"] having an ethylenic unsaturated bond, a structure obtained by epoxidizing a cycloalkene and a structure obtained by epoxidizing a And a monomer (b-2) having an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b-2)"). (b-1) is preferable from the viewpoint of reactivity.

(meth) acrylate,? -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl (meth) acrylate, Vinylbenzyl glycidyl ether,? -Methyl-o-vinylbenzyl glycidyl ether,? -Methyl-o-vinylbenzyl glycidyl ether,? Methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5- Styrenes such as 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) styrene, Styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2,4,6-tris (glycidyloxymethyl) And compounds described in JP-A No. 7-248625.

(b-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane [e.g., Sucoxide 2000; (Manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl acrylate [e.g., CYRAMER A400; (Manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl methacrylate [for example, Cyclomer M100; (Manufactured by Daicel Co., Ltd.), a compound represented by the formula (I) and a compound represented by the formula (II).

In the formulas (I) and (II), R ¹ and R ² independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.

X ¹ and X ² independently represent a single bond, -R ³ -, -R ³ -O-, -R ³ -S- or -R ³ -NH-.

R ³ represents an alkanediyl group having 1 to 6 carbon atoms.

* Represents the number of bonds with O.]

The binder resin (Aa) can be produced through a two-step process. In this case, for example, a method described in "Experimental Method of Polymer Synthesis" (published by Otsu Takayuki Publishing Co., Ltd., 1st edition, 1st edition, published on Mar. 1, 1972), and Japanese Patent Laid-Open Publication No. 2001-89533 Can be produced by referring to the method described in the publication.

In the production of the binder resin (Aa), the addition polymer (a) of (a1) and (a2) is first obtained as a first step. Specifically, a method of injecting predetermined amounts (a1) and (a2), a polymerization initiator, a solvent and the like into a reaction vessel and substituting oxygen with nitrogen for stirring, heating, and keeping them in an atmosphere of deoxygenation is exemplified. The polymerization initiator, solvent and the like to be used herein are not particularly limited, and any of those commonly used in the relevant fields can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) and organic peroxides (such as benzoyl peroxide) The solvent may be any one which dissolves the respective monomers, and a solvent to be described later may be used as a solvent of the colored photosensitive resin composition.

The obtained addition polymer may be used as it is as the solution after the reaction, as a concentrated or diluted solution, or as a solid (powder) obtained by re-precipitation or the like.

the ratio of the structural units derived from (a1) and (a2) is preferably within the following range with respect to the total number of moles of the total structural units constituting the addition polymer (a).

a structural unit derived from the structural unit (a1); 5 to 50 mol%, more preferably 10 to 45 mol%

a structural unit derived from the structural unit (a2); 50 to 95 mol%, more preferably 55 to 90 mol%

Next, as a second step, a part of the carboxylic acid groups in the structural unit derived from (a1) of the obtained addition polymer is reacted with (b). (B) is preferably (b-1) in that the reactivity is high and unreacted (b) is hard to remain.

Specifically, the atmosphere in the flask is substituted with air in the flask, and the reaction catalyst (such as tris (dimethylaminomethyl) phenol, etc.) is added in an amount of 5 to 80 mol% based on the molar amount of (a1) (a1), (b) and (a2) in an amount of 0.001 to 5 mass% relative to the total amount of (a1), (b) and (a2), and a polymerization inhibitor (such as hydroquinone) %, In a flask, and usually at 60 to 130 ° C for 1 to 10 hours to obtain a binder resin (Aa). In addition, as in the case of the polymerization conditions, the injection method and the reaction temperature can be appropriately adjusted in consideration of the amount of heat generated by the production facility or polymerization.

In this case, the number of moles of (b) is preferably 10 to 75 mol%, and more preferably 15 to 70 mol% based on the number of moles of (a1). When the number of moles of (b) is within this range, balance between storage stability, solvent resistance and heat resistance tends to be improved.

Examples of the binder resin (Aa) include a resin obtained by reacting a copolymer of (meth) acrylic acid / dicyclopentanyl (meth) acrylate with glycidyl (meth) acrylate, a resin obtained by reacting (meth) acrylic acid / benzyl (Meth) acrylic acid / styrene (meth) acrylate, a resin obtained by reacting a copolymer of (meth) acrylic acid / cyclohexyl (meth) acrylate with glycidyl (Meth) acrylate, (meth) acrylic acid / N, N'-dicyclohexyl (meth) acrylate, a resin obtained by reacting a copolymer of (meth) acrylic acid / - a resin obtained by reacting a copolymer of crotonic acid / dicyclopentyl (meth) acrylate with glycidyl (meth) acrylate, a resin obtained by reacting a copolymer of cyclohexylmaleimide with glycidyl (meth) acrylate;

(Meth) acrylate is reacted with a copolymer of crotonic acid / cyclohexyl (meth) acrylate and a resin obtained by reacting a copolymer of crotonic acid / benzyl (meth) acrylate with glycidyl (Meth) acrylate on a copolymer of crotonic acid / styrene, a resin obtained by reacting a copolymer of crotonic acid / methyl crotonate with glycidyl (meth) acrylate, a crotonic acid / A resin obtained by reacting a copolymer of N-cyclohexylmaleimide with glycidyl (meth) acrylate;

(Meth) acrylate is added to a copolymer of maleic acid / dicyclopentanyl (meth) acrylate and a copolymer of maleic acid / benzyl (meth) acrylate with glycidyl (Meth) acrylate is reacted with a copolymer of maleic acid / cyclohexyl (meth) acrylate, glycidyl (meth) acrylate is allowed to react with a copolymer of maleic acid / styrene A resin obtained by reacting a copolymer of maleic acid / methyl maleic acid with glycidyl (meth) acrylate, or a resin obtained by reacting glycidyl (meth) acrylate with a copolymer of maleic acid / N-cyclohexylmaleimide ;

(Meth) acrylic acid / maleic anhydride / dicyclopentanyl (meth) acrylate, a resin obtained by reacting glycidyl (meth) acrylate with a copolymer of (meth) acrylic acid / maleic anhydride / dicyclopentanyl A resin obtained by reacting a copolymer of glycidyl (meth) acrylate with a copolymer of (meth) acrylic acid / maleic anhydride / cyclohexyl (meth) acrylate, (Meth) acrylic acid / maleic anhydride / methyl (meth) acrylate is copolymerized with a copolymer of a (meth) acrylic acid / maleic anhydride / styrene copolymer and a glycidyl (meth) (Meth) acrylic acid / maleic anhydride / N-cyclohexylmaleimide; a resin obtained by reacting glycidyl (meth) acrylate with a copolymer of (meth) acrylic acid / maleic anhydride / N-cyclohexylmaleimide;

(Meth) acrylic acid / dicyclopentanyl (meth) acrylate, a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of (meth) acrylic acid / Epoxy cyclohexylmethyl methacrylate, a resin obtained by reacting a copolymer of (meth) acrylic acid / cyclohexyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, a resin obtained by reacting (meth) acrylic acid / Styrene is reacted with 3,4-epoxycyclohexylmethyl methacrylate, and a copolymer of (meth) acrylic acid / methyl (meth) acrylate is reacted with 3,4-epoxycyclohexylmethyl methacrylate Resin, a resin obtained by reacting a copolymer of (meth) acrylic acid / N-cyclohexylmaleimide with 3,4-epoxycyclohexylmethyl methacrylate;

Epoxycyclohexylmethyl methacrylate on a copolymer of crotonic acid / dicyclopentanyl (meth) acrylate and a copolymer of crotonic acid / benzyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, Cyclohexylmethyl methacrylate, a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of crotonic acid / cyclohexyl (meth) acrylate, and a copolymer of crotonic acid / styrene with 3, 4-epoxycyclohexylmethyl methacrylate, a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of crotonic acid / methyl crotonate and a resin obtained by reacting crotonic acid / N-cyclohexylmaleimide A resin obtained by reacting a copolymer with 3,4-epoxycyclohexylmethyl methacrylate;

A resin obtained by reacting a copolymer of maleic acid / dicyclopentanyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, and a copolymer of maleic acid / benzyl (meth) acrylate with 3,4-epoxycyclo Maleic acid / cyclohexyl (meth) acrylate is reacted with 3,4-epoxycyclohexylmethyl methacrylate, a copolymer obtained by reacting maleic acid / cyclohexyl (meth) acrylate with 3,4- 4-epoxycyclohexylmethyl methacrylate, a resin obtained by reacting a copolymer of maleic acid / methyl maleic acid with 3,4-epoxycyclohexylmethyl methacrylate, a resin obtained by reacting maleic acid / N-cyclohexylmaleimide A resin obtained by reacting a copolymer with 3,4-epoxycyclohexylmethyl methacrylate;

(Meth) acrylic acid / maleic anhydride / benzyl (meth) acrylate, a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of (meth) acrylic acid / maleic anhydride / dicyclopentanyl (Meth) acrylic acid / maleic anhydride / cyclohexyl (meth) acrylate was added to a copolymer of 3,4-epoxycyclohexylmethyl methacrylate and 3,4-epoxycyclohexylmethyl methacrylate (Meth) acrylic acid / maleic anhydride / (meth) acrylic acid / maleic anhydride / styrene, a resin obtained by reacting a (meth) acrylic acid / maleic anhydride / (Meth) acrylic acid / maleic anhydride / N-cyclohexylmaleimide was added to a copolymer of 3,4-epoxycyclohexylmethyl methacrylate and 3,4-epoxycyclohexylmethyl methacrylate Krill There may be mentioned resins such as by reacting the site.

The binder resin (Aa) is more preferably a resin obtained by reacting (b) an addition polymer obtained by copolymerizing (a1), (a2-1) and (a2-1) . When the binder resin (Aa) has the above-mentioned constitution, the obtained pattern tends to have excellent adhesion with the substrate and excellent solvent resistance.

When the addition polymer (a1) is composed of (a2) other than (a2-1) and (a2-1) (The structural unit derived from (a2) other than the structural unit derived from (a2-1): the structural unit derived from (a2-1)) is preferably 10:90 to 60:40, : 60, and more preferably 10:90 to 30:70.

(meth) acrylate / dicyclopentanyl (meth) acrylate (b1) to the addition polymer obtained by copolymerizing (a1) other than the monomer (a1) (Meth) acrylic acid / dicyclopentanyl (meth) acrylate / cyclohexyl (meth) acrylate copolymerized with a copolymer of (meth) acrylic acid / dicyclopentanyl (Meth) acrylic acid / dicyclopentanyl (meth) acrylate / styrene, a resin obtained by reacting glycidyl (meth) acrylate with a copolymer of (meth) acrylic acid / (Meth) acrylic acid / dicyclopentanyl (meth) acrylate / N-cyclohexylmalei (meth) acrylate / methyl (meth) acrylate, a resin obtained by reacting glycidyl (Meth) < RTI ID = 0.0 >Acrylate;

A resin obtained by reacting a copolymer of crotonic acid / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate with glycidyl (meth) acrylate, a crotonic acid / dicyclopentanyl (meth) acrylate / cyclohexyl (Meth) acrylate is reacted with a copolymer of a crotonic acid / dicyclopentanyl (meth) acrylate / styrene copolymer and glycidyl (meth) (Meth) acrylate / dicyclopentanyl (meth) acrylate / methyl crotonate, a resin obtained by reacting glycidyl (meth) A resin obtained by reacting glycidyl (meth) acrylate with a copolymer of methyl methacrylate and methyl methacrylate;

A resin obtained by reacting a copolymer of maleic acid / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate with glycidyl (meth) acrylate, maleic acid / dicyclopentanyl (meth) acrylate / cyclohexyl (Meth) acrylate is reacted with a copolymer of maleic acid / dicyclopentanyl (meth) acrylate / styrene and a resin obtained by reacting glycidyl (meth) acrylate with a copolymer of maleic acid / dicyclopentanyl , A resin obtained by reacting a copolymer of maleic acid / dicyclopentanyl (meth) acrylate / methyl maleic acid with glycidyl (meth) acrylate, a resin obtained by reacting maleic acid / dicyclopentanyl (meth) acrylate / N-cyclohexylmale A resin obtained by reacting glycidyl (meth) acrylate with a copolymer of methyl methacrylate and methyl methacrylate;

(Meth) acrylic acid / maleic anhydride / maleic anhydride / maleic anhydride / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate, a resin obtained by reacting a copolymer of (meth) acrylic acid / maleic anhydride / (Meth) acrylate / maleic anhydride / dicyclopentanyl (meth) acrylate, a resin obtained by reacting a copolymer of dicyclopentanyl (meth) acrylate and cyclohexyl (meth) (Meth) acrylate in a copolymer of (meth) acrylic acid / maleic anhydride / dicyclopentanyl (meth) acrylate / methyl (meth) acrylate, a resin obtained by reacting glycidyl (Meth) acrylate, a resin obtained by reacting glycidyl (meth) acrylate with a copolymer of (meth) acrylic acid / maleic anhydride / dicyclopentanyl (meth) acrylate / N-cyclohexylmaleimide;

A resin obtained by reacting a copolymer of (meth) acrylic acid / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, a resin obtained by reacting (meth) acrylic acid / dicyclopentanil (Meth) acrylate / cyclohexyl (meth) acrylate, a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of (meth) acrylic acid / dicyclopentanyl (Meth) acrylic acid / dicyclopentanyl (meth) acrylate / methyl (meth) acrylate was added to a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate A resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of (meth) acrylic acid / dicyclopentanyl (meth) acrylate / N-cyclohexylmaleimide;

(Meth) acrylate / dicyclopentanyl (meth) acrylate / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate, a resin obtained by reacting 3,4- A copolymer obtained by reacting a copolymer of cyclohexyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, a copolymer of crotonic acid / dicyclopentanyl (meth) acrylate / styrene and 3,4-epoxycyclo A resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate with a copolymer of crotonic acid / dicyclopentanyl (meth) acrylate / methyl crotonate and a resin obtained by reacting crotonic acid / dicyclohexylmethyl methacrylate, A resin obtained by reacting a copolymer of fentanyl (meth) acrylate / N-cyclohexylmaleimide with 3,4-epoxycyclohexylmethyl methacrylate;

A resin obtained by reacting a copolymer of maleic acid / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, a resin obtained by reacting maleic acid / dicyclopentanyl (meth) Cyclohexyl (meth) acrylate is reacted with 3,4-epoxycyclohexylmethyl methacrylate, and a copolymer of maleic acid / dicyclopentanyl (meth) acrylate / styrene and 3,4-epoxycyclohexylmethyl methacrylate is added to a copolymer of maleic acid / Maleic acid / dicyclopentanyl (meth) acrylate / maleic acid methyl ester, maleic acid / dicyclopentanyl (meth) acrylate / maleic acid methyl ester and maleic acid / dicyclohexylmethyl methacrylate; a resin obtained by reacting 3,4- A resin obtained by reacting a copolymer of fentanyl (meth) acrylate / N-cyclohexylmaleimide with 3,4-epoxycyclohexylmethyl methacrylate;

A resin obtained by reacting a copolymer of (meth) acrylic acid / maleic anhydride / dicyclopentanyl (meth) acrylate / benzyl (meth) acrylate with 3,4-epoxycyclohexylmethyl methacrylate, a (meth) acrylic acid / maleic (Meth) acrylic acid / maleic anhydride / dicyclopentyl (meth) acrylate / dicyclohexyl (meth) acrylate / cyclohexyl (meth) (Meth) acrylic acid / maleic anhydride / dicyclopentanyl (meth) acrylate / (meth) acrylate / styrene copolymer, and a resin obtained by reacting 3,4-epoxycyclohexylmethyl methacrylate (Meth) acrylic acid / maleic anhydride / dicyclopentanyl (meth) acrylate / N-cyclohexylmaleimide copolymerized with 3,4-epoxycyclohexylmethyl methacrylate A resin or the like can be given by reacting a 3,4-epoxycyclohexylmethyl methacrylate.

These binder resins (A) may be used alone or in combination of two or more.

The weight average molecular weight (Mw) of the binder resin (A) in terms of polystyrene is preferably 8 × 10 ^{3 to} 100 × 10 ³ , more preferably 10 × 10 ^{3 to} 50 × 10 ³ . When the weight average molecular weight (Mw) of the binder resin (A) is within the above-mentioned range, the coating property of the photosensitive resin composition and the low sticking property of the dried film tend to be better. In addition, , And the removability of the non-pixel portion at the time of development tends to be good.

The acid value of the binder resin (A) is preferably 30 to 200 mg-KOH / g, more preferably 40 to 190 mg-KOH / g, and still more preferably 50 to 180 mg-KOH / g. Acid value is a value measured as the amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the binder resin (A), and can be determined by titration using an aqueous potassium hydroxide solution.

The binder resin (A) is preferably composed only of the above-mentioned binder resin (Aa), but other resins may be included. Examples of such a resin include an epoxy resin, an acrylic resin, a urethane resin, a polyester resin, a polyimide resin, a polyolefin resin, a novolak resin, and a polyamine resin.

When the binder resin (A) contains a resin other than the binder resin (Aa), the content of the binder resin (Aa) is preferably from 20 to 99 mass%, more preferably from 50 to 99 mass% Is more preferable.

The polymerizable compound (B) is not particularly limited as long as it is a compound capable of initiating polymerization by an active radical, acid, or the like generated from the polymerization initiator (C) by the action of light or heat. As the polymerizable compound (B), a compound having a polymerizable carbon-carbon unsaturated bond can be exemplified, and a monofunctional monomer, a bifunctional monomer, and a multifunctional monomer having three or more functionalities are preferably used. As the polymerizable compound (B), a compound having no acidic group is preferably used.

Examples of monofunctional monomers include nonylphenylcarbitol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-ethylhexylcarbitol (meth) acrylate, 2- ) Acrylate, and N-vinylpyrrolidone.

Examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) Bis (acryloyloxyethyl) ether, 3-methylpentanediol di (meth) acrylate, and tricyclodecanedimethanol di (meth) acrylate.

Examples of the multifunctional monomer having three or more functional groups include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (Meth) acrylate, a reaction product of pentaerythritol tri (meth) acrylate and an acid anhydride, a reaction product of dipentaerythritol penta (meth) acrylate and an acid anhydride, V # 1000 manufactured by Osaka Yuki Kagaku Kogyo Co., UA-306H, UA-306T, UA-306I, and New Frontier R-1150 manufactured by Daiichi Kogyo Seiyaku Co., Ltd., And the like. Among them, a bifunctional monomer and a multifunctional monomer having three or more functional groups are preferably used.

As the polymerizable compound (B), the following polymerizable compounds may be used.

These polymerizable compounds (B) may be used alone or in combination of two or more.

The content of the polymerizable compound (B) is preferably from 1 to 50 mass%, more preferably from 5 to 30 mass%, based on the solid content of the photosensitive resin composition. The content of the binder resin (A) is preferably 30 to 80 parts by mass based on 100 parts by mass of the total amount of the binder resin (A) and the polymerizable compound (B).

Here, the solid content refers to all components except for the solvent contained in the photosensitive resin composition.

When the content of the binder resin (A) is in the above-mentioned range, it is preferable because the tackiness of the dried film is further suppressed and a color filter free from color unevenness tends to be obtained.

The polymerization initiator (C) may be a photopolymerization initiator that generates an active radical, an acid, or the like by the action of light, which generates an active radical or acid for initiating polymerization of the polymerizable compound (B) May be a thermal polymerization initiator that generates an active radical or an acid by the action of a photo polymerization initiator. However, it is preferably a photopolymerization initiator and more preferably a photo radical polymerization initiator that generates an active radical by the action of light.

The polymerization initiator (C) is preferably an oxime compound. By using such a polymerization initiator, the photosensitive resin composition becomes highly sensitive, and the film formed by using the polymerization initiator is excellent in resolution and solvent resistance, so that the pattern becomes good. In addition, it is preferable to use the polymerization initiator (C-1) in combination, because the resultant photosensitive resin composition has a higher sensitivity and productivity when a color filter is formed using the same.

Examples of the oxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-acetoxy- 1- [ 3-yl] ethan-1-imine, N-acetoxy-1- [ Fentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethan-1-imine. Commercially available products such as Irgacure (registered trademark) OXE-01, OXE-02 (manufactured by BASF Japan) and N-1919 (manufactured by ADEKA) may be used. Among them, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (the following formula) is preferred.

Examples of the polymerization initiator other than the oxime compound include a nonimidazole compound, an alkylphenone compound, a triazine compound, and an acylphosphine oxide compound.

Examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- 4,4 ', 5,5'-tetraphenylbiimidazole (see, for example, JP-A 6-75372, JP-A 6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) ) Diimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (dialkoxyphenyl) 4,4 ', 5,5'-tetra (trialkoxyphenyl) bimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, , Imidazole compounds in which the phenyl group at the 4 ', 5, 5'-position is substituted by a carboalkoxy group (for example, see Japanese Patent Application Laid-open No. 7-10913). Preferred are 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl) ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole.

Examples of the alkylphenone compound include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan- (2-hydroxy-2-methyl-benzothiazol-2-yl) 2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenyl Ketone and oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propane-1-one and the like, (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one. Commercially available products such as Irgacure (registered trademark) 369, 907 (manufactured by BASF Japan Ltd.) may be used.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4- Methyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- 2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4,6-trichloromethyl- Bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- - [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like. A commercially available product such as Irgacure (registered trademark) 819 (manufactured by BASF Japan Ltd.) may be used.

Examples of the polymerization initiator (C) other than oxime compounds, imidazole compounds, alkylphenone compounds, triazine compounds and acylphosphine oxide compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether , Benzoin isobutyl ether; Benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert- butylperoxycarbonyl) benzophenone Benzophenone compounds such as 2,4,6-trimethylbenzophenone; Quinone compounds such as 9,10-phenanthrenequinone, 2-ethyl anthraquinone, and campquinone; Butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.

These polymerization initiators (C) may be used alone, or two or more of them may be used in combination.

The content of the polymerization initiator (C) is preferably 0.1 to 80 parts by mass, and more preferably 1 to 60 parts by mass, based on 100 parts by mass of the total amount of the resin (A) and the polymerizable compound (B). When the total amount of the polymerization initiator is within this range, a pattern can be formed with a high sensitivity, and the chemical resistance, mechanical strength and surface smoothness of the pattern tend to be improved.

The polymerization initiator (C) is preferably used in combination with the polymerization initiator (C-1) (particularly amines). The polymerization initiator (C-1) is a compound or a sensitizer used for promoting polymerization of the polymerizable compound initiated by the polymerization initiator (C).

Examples of the polymerization initiator (C-1) include an amine compound, a thiazoline compound, an alkoxyanthracene compound, a thioxanthone compound, a carboxylic acid compound, and a thiol compound.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethyl paratoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, '-Bis (ethylmethylamino) benzophenone, among which 4,4'-bis (diethylamino) benzophenone is preferable. EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) and the like may be used.

Examples of the thiazoline compound include compounds represented by the formulas (III-1) to (III-3).

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, Ethoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, and the like.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Oakstone, and the like.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, Diphenylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

Examples of the thiol compound include 2-sulfanyloxazole, 2-sulfanylthiazole, 2-sulfanylbenzimidazole, 2-sulfanylbenzothiazole, 2-sulfanylbenzoxazole, Sulfanylpyridine-N-oxide, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4-amino-6-hydroxy- Amino-2-sulfanylpyrimidine, 6-amino-5-nitroso-2-thiouracil, 4,5-diamino-6-hydroxy- 2-sulfanylpyrimidine, 2,4-diamino-6-sulfanylpyrimidine, 4,6-dihydroxy-2-sulfanylpyrimidine, 4,6-dimethyl- Sulfanyl-6-methylpyrimidine, 4-hydroxy-2-sulfanyl-6-propylpyrimidine, 2-sulfanyl-4-methylpyrimidine, 2 -Sulfanylimidazole, 2-thiouracil, 3,4,5,6-tetrahydropyrimidine-2-thiol, 4,5-diphenylimidazole- 2-sulfanyl-1-methylimidazole Amino-3-hydrazino-5-sulfanyl-1,2,4-triazole, 3-amino-5-sulfanyl-1,2,4-triazole, 2- Triazole-3-thiol, 4-methyl-4H-1,2,4-triazole-3-thiol, 3-sulfanyl-1H- Amino-5-sulfanyl-1,3,4-thiadiazole, 5-amino-1,3,4-thiadiazole-2-thiol, 2,5-disulfanyl- Thienylidene, 2-sulfanylthiazoline, 2-sulfanyl-4 (3H) -quinazolinone, 1-phenyl 2-sulfanyl-5-methylbenzimidazole, 2-sulfanyl-5-nitrobenzimidazole, 6-amino-2-sulfanylbenzothiazole 2-sulfanyl benzothiazole, 2-sulfanyl benzothiazole, 2-sulfanyl naphthoimidazole, 2- 2,4-d] pyridine, 2-amino-6-purin thiol, 6-sulfanyl-1,2,4-triazole, Panyl purine, 4-sulfanyl-1H- (Methylsulfanyl) benzene, butanediol bis (3-sulfanyl propionate), butanediol bis (3-sulfanyl) Acetate), ethylene glycol bis (3-sulfanyl acetate), trimethylolpropane tris (3-sulfanyl acetate), butanediol bis (3-sulfanylpropionate), trimethylolpropane tris (3-sulfanyl acetate), pentaerythritol tetrakis (3-sulfanyl propionate), pentaerythritol tetrakis (3-sulfanyl acetate), trishydroxyethyl tris (3-sulfanylbutyl) butane, 1,4-bis (3-sulfanylbutyloxy) butane, and the like.

When the polymerization initiator (C-1) is used, the content thereof is preferably 0.01 to 50 parts by mass, more preferably 0.1 to 50 parts by mass based on 100 parts by mass of the total amount of the resin (A) and the polymerizable compound (B) 40 parts by mass. It is preferably 0.01 to 10 moles, more preferably 0.01 to 5 moles, per 1 mole of the polymerization initiator (C). When the content of the polymerization initiator (C-1) is within this range, it is possible to form a pattern with higher sensitivity, and the productivity of the pattern tends to be improved.

The extender pigment (D) is not particularly limited, but at least one selected from the group consisting of silicon oxide, barium sulfate, titanium oxide, zinc oxide, aluminum oxide, magnesium oxide and calcium carbonate can be used. From the viewpoint of transparency, it is preferable that the extender pigment has an average particle diameter of 500 nm or less. Among them, silicon oxide is preferable from the viewpoints of reliability and low stickiness of the dried film.

The content of the extender pigment (D) is preferably 0.1 to 80 parts by mass, more preferably 1 to 30 parts by mass, based on 100 parts by mass of the total amount of the resin (A) and the polymerizable compound (B). When the content of the extender pigment is in this range, there is a tendency that the low stickiness and the solvent resistance of the dried film become good.

The photosensitive resin composition of the present invention, the solubility parameter is 8.0 ~ 9.1 (cal / ㎤) 1/2 of the solvent (E1) and the solubility parameter is 9.2 ~ 11.0 (cal / ㎤) 1/2 include solvents (E2) do. By using the photosensitive composition containing such a predetermined solvent, a dried film having satisfactory low tackiness can be obtained, and a pattern having satisfactory hardness can be obtained.

As the solvent (E1) having a solubility parameter of 8.0 to 9.1 (cal / cm3) ^1/2 , its solubility parameter (cal / cm3) ^1/2 is appended with parentheses, for example, ethylene glycol mono-i-butyl ether Propyl ether (8.8), dipropylene glycol mono n-butyl ether (8.5), tripropylene glycol mono n-propyl ether (8.5), diethylene glycol mono ), Tripropylene glycol mono n-butyl ether (8.2), ethylene glycol dimethyl ether (8.6), diethylene glycol dimethyl ether (8.6), diethylene glycol diethyl ether (8.6), diethylene glycol di- 8.3), triethylene glycol dimethyl ether (8.4), diethylene glycol ethyl methyl ether (8.6), diethylene glycol mono n-butyl ether acetate (9.0), propylene glycol monomethyl ether acetate (9.0), dipropylene glycol monomethyl Ether acetate (8.1), ethyl-3-ethoxypropionate (9.1), n-propyl acetate (8.6), n-propyl propionate (8.6), n-butyl propionate (8.3), n-pentyl propionate (8.4), ethyl acetate (9.1) and butyl acetate (8.3). Of these, acylates of monoethers of diols such as propylene glycol monomethyl ether acetate are preferable from the viewpoint of solubility, and alkaneates of alkylene glycol, dialkylene glycol or monoalkyl ether of trialkylene glycol are more preferable .

The solvent (E2) having a solubility parameter of 9.2 to 11.0 (cal / cm3) ^{1/2 has} its solubility parameter ((cal / cm3) ^1/2 ) parenthesized, for example, ethylene glycol monopropyl ether (10.6) , Ethylene glycol mono isopropyl ether (9.2), ethylene glycol mono n-butyl ether (10.2), ethylene glycol monohexyl ether (9.4), ethylene glycol monophenyl ether (10.9), ethylene glycol monobenzyl ether Diethylene glycol monoallyl ether (9.8), diethylene glycol monomethyl ether (10.7), diethylene glycol mono n-butyl ether (10.0), diethylene glycol monohexyl ether (9.7), diethylene glycol mono 2-ethylhexyl ether 9.2), diethylene glycol monobenzyl ether (9.6), triethylene glycol monomethyl ether (10.2), triethylene glycol monoethyl ether (9.9), triethylene glycol mono-n-butyl ether (9.3), polyethylene glycol monomethyl ether (9.2), propylene glycol monomethyl ether Propyleneglycol mono-n-butyl ether (9.3), propylene glycol mono-t-butyl ether (9.7), propylene glycol monophenyl ether (11.0), dipropylene glycol Propylene glycol monomethyl ether (9.6), tripropylene glycol monomethyl ether (9.4), ethylene glycol mono n-butyl ether acetate (10.3), propylene glycol diacetate (9.6), methyl-3-methoxypropionate (10.7), butyl lactate (9.8), cyclohexanone (9.9), 4-hydroxy-4-methyl-2-pentanone (alias diacetone alcohol) (10.0), chloroform (9.3), acetone (9.9), and 1,1,2,2-tetrachloroethane (9.7). Among them, a hydroxy compound is preferable from the viewpoint of solubility, and a monoether of a diol such as propylene glycol monomethyl ether and a hydroxy ketone such as 4-hydroxy-4-methyl-2-pentanone are more preferable, Monoalkyl ethers of glycols, dialkylene glycols or trialkylene glycols, and hydroxyalkanones are more preferred.

The content of the solvent (E1) having a solubility parameter of 8.0 to 9.1 (cal / cm3) ^1/2 is 70 to 99% by mass, preferably 70 to 97% by mass with respect to the solvent (E) The content of the solvent (E2) of 9.2 to 11.0 (cal / cm3) ^1/2 is 1 to 30 mass%, preferably 3 to 30 mass%, with respect to the solvent (E). When the ratio of the mass% of the solvent is in the above range, solubility and flatness at the time of coating tend to be improved. The solvent (E) may contain a solvent other than the solvents (E1) and (E2), but the content thereof is usually 20 mass% or less, preferably 10 mass% or less to be.

The solubility parameter can be determined by the following equation.

Solubility parameter = (? E / V) ^1/2

? E: cohesive energy (evaporation enthalpy), V: molar volume

The solvent (E) may be used in the synthesis of the binder resin (A).

The content of the solvent (E) is preferably 60 to 95% by mass, and more preferably 70 to 90% by mass, based on the photosensitive resin composition. In other words, the solid content of the photosensitive resin composition is preferably 5 to 40% by mass, and more preferably 10 to 30% by mass. When the content of the solvent (E) is in the above range, the flatness at the time of coating tends to be good.

The photosensitive resin composition of the present invention preferably further comprises a colorant (F). Examples of the colorant (F) include pigments and dyes. However, from the viewpoints of heat resistance and light resistance of the pattern, it is preferable to include a pigment, and from the viewpoint of light transmittance of the pattern, It is more preferable to include a dye.

Examples of the pigment include organic pigments and inorganic pigments, and compounds classified by pigment index (published by The Society of Dyers and Colourists) as pigments.

As the organic pigment, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139 , 147, 148, 150, 153, 154, 166, 173, 194 and 214;

C.I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Red pigments such as Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, ;

C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Green pigments such as Pigment Green 7, 36, and 58;

C.I. Brown pigments such as Pigment Brown 23 and 25;

C.I. Pigment black 1, pigment black 7, and the like.

Among them, C.I. Pigment Yellow 138, 139, 150, C.I. Pigment Red 177, 242, 254, C.I. Pigment Violet 23, C.I. Pigment Blue 15: 3, 15: 6, C.I. Pigment greens 7, 36 and 58 are preferred.

These pigments may be used singly or in combination of two or more kinds.

The pigment may be subjected to a surface treatment using a pigment derivative or a pigment dispersing agent to which a rosin treatment, an acidic group or a basic group is introduced, a graft treatment on a pigment surface with a polymer compound or the like, an atomization treatment using a sulfuric acid atomization method, A cleaning treatment with an organic solvent or water to remove impurities, a removal treatment with an ion exchange method of ionic impurities, or the like may be performed. It is preferable that the pigment has a uniform particle size. By containing a pigment dispersant and carrying out a dispersion treatment, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

As the above-mentioned pigment dispersant, commercially available surfactants can be used, and surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic, amphoteric, polyester, polyamine, . Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethyleneimines and the like (Manufactured by Shin-Etsu Chemical Co., Ltd.), fluorene (manufactured by Gyoe Shikagaku Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA Spur (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.) and Disperbyk (manufactured by Big-Mass). These may be used alone or in combination of two or more.

When a pigment dispersant is used, its amount to be used is preferably 100% by mass or less, and more preferably 5 to 50% by mass, based on the pigment. When the amount of the pigment dispersant is within the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

As the colorant (F), known dyes can also be used. Examples of the dyes include oil-soluble dyes and acid dyes.

These dyes are appropriately selected in accordance with the solubility in a solvent and the light discoloration resistance and spectral spectrum when a pattern of a color filter is formed using a colored curable resin composition containing the dye.

The dye is not particularly limited and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, mordant dyes and the like. Examples of the dyes include compounds classified by the color index (published by The Society of Dyers and Colourists) as having a color other than pigment, and known dyes described in dyeing notes (Shika Sensha). In addition, according to the chemical structure, it is possible to use azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, Acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

Specifically, C.I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

C.I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, Solvent dyes,

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 112, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 266, 268, 270, 274, 277, 280, 281, 272, 277, 278, 279, 252, 257, 258, 260, 261, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;

C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 90, 90, 91, 92, 93, 93, 1, 2, 3, 4, 5, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;

C.I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 104, 105, 106, 109, Acid dyes,

C.I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 136, 138, 141;

C.I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

C.I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 236, 237, 238, 242, 243, 244, 245, 246, 234, 236, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, Direct dyes,

C.I. Disperse Yellow 51, 54, 76;

C.I. Disperse Violet 26, 27;

C.I. Disperse Blue 1, 14, 56, 60, etc. C.I. Disperse dyes,

C.I. Basic red 1, 10;

C.I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;

C.I. Basic Violet 2;

C.I. Basic Red 9;

C.I. Basic Green 1; C.I. Basic dyes,

C.I. Reactive Yellow 2, 76, 116;

C.I. Reactive Orange 16;

C.I. Reactive red 36; C.I. Reactive dye

C.I. Modern Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

C.I. 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

C.I. Modern orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

C.I. Modern Violet 1, 1: 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

C.I. 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;

C.I. C.I., such as Modern Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, Modern dyes,

C.I. C.I. Vat dyes and the like.

These dyes may be suitably selected in accordance with the spectral spectrum of a desired color filter.

The dye preferably contains a compound having a xanthene skeleton in the molecule.

The content of the colorant (F) is preferably from 5 to 60 mass%, more preferably from 5 to 45 mass%, based on the solid content of the photosensitive resin composition. When the content of the colorant (F) is within the above range, desired spectral or color density can be obtained.

The photosensitive resin composition of the present invention may contain a surfactant. Examples of the surfactant include a silicone surfactant, a fluorine surfactant, and a silicon surfactant having a fluorine atom. The inclusion of the surfactant tends to improve the flatness at the time of application.

As the silicone surfactant, a surfactant having a siloxane bond can be mentioned. Specific examples thereof include TORAY silicone DC3PA, TORAY silicone SH7PA, TORAY silicone DC11PA, TORAY silicone SH21PA, TORAY silicone SH28PA, TORAY silicone SH29PA, TORAY silicone SH30PA, polyether-modified silicone oil SH8400 (Toray Dow Corning Co., Ltd.) , KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (Momentive Performance Materials (Manufactured by Japan Kogyo Co., Ltd.).

As the fluorochemical surfactant, a surfactant having a fluorocarbon chain can be mentioned. Specifically, there are used a flourine (registered trademark) FC430, Florinat FC431 (manufactured by Sumitomo 3M Ltd.), Megapack (registered trademark) F142D, Megapack F171, Megapack F172, Megapack F173, Megapack F177, (Registered trademark) EF301, EF TOP EF303, EF TOP EF351 and EF TOP EF352 (manufactured by Mitsubishi Materials Denshi Kasei Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Industries Co., Ltd.).

Examples of the silicone surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain. Specific examples thereof include Megapack (registered trademark) R08, Megapark BL20, Megapack F475, Megapack F477, Megapack F443 (manufactured by DIC Corporation) and the like. And preferably Megapak (registered trademark) F475.

The surfactant is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and particularly preferably 0.01 to 0.05% by mass, based on the photosensitive resin composition. When the surfactant is contained in this range, the flatness of the coating film can be improved.

The photosensitive resin composition of the present invention may contain various additives such as fillers, other polymer compounds, adhesion promoters, antioxidants, ultraviolet absorbers, light stabilizers, and chain transfer agents, if necessary.

The photosensitive resin composition of the present invention is a photosensitive resin composition containing a binder resin (A), a polymerizable compound (B), a polymerization initiator (C), an extender pigment (D), a solvent (E) and optionally a colorant (F) .

When the pigment is mixed as the colorant (F), it is preferable to prepare it in the following procedure, for example.

First, the pigment is mixed with the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, a part or all of the pigment dispersant and the binder resin (A) may be blended. To the pigment dispersion thus obtained, the remainder of the binder resin (A), the polymerizable compound (B), the polymerization initiator (C), the extender pigment (D) and other components as required, E) is added so as to have a predetermined concentration to obtain a photosensitive resin composition.

Examples of the method of applying the photosensitive resin composition of the present invention to a substrate include an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, a CAP coating method and a die coating method. In addition, even if a coating apparatus such as dip coater, roll coater, bar coater, spin coater, slit & spin coater, slit coater (die coater, curtain float coater, spunless coater) good. Among them, it is preferable to apply by using a slit coater, a spin coater, a roll coater or the like.

Examples of a drying method of a coating film obtained by applying a photosensitive resin composition to a substrate include heat drying, natural drying, air drying, and vacuum drying. A plurality of methods may be combined.

The drying temperature is preferably 10 ° C to 120 ° C, more preferably 25 ° C to 100 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

The reduced-pressure drying is preferably carried out under a pressure of 50 to 150 Pa at a temperature of 20 to 25 캜.

The film thickness of the dried film obtained by drying the coated film is not particularly limited and can be suitably adjusted according to the material to be used and the application, and is usually 0.1 to 20 탆, preferably 1 to 6 탆.

The dry film is exposed through a photomask for forming a desired pattern. The pattern shape on the photomask at this time is not particularly limited, and a pattern shape according to the intended use is used. When a thermal polymerization initiator is used as the polymerization initiator (C), the dry film is heated by exposure, and this heat acts on the thermal polymerization initiator.

As a light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light having a wavelength of less than 350 nm may be cut using a filter that cuts the wavelength region, or light having wavelengths around 436 nm, 408 nm, and 365 nm may be selectively extracted using a band- Or may be taken out. Examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.

It is preferable to use an apparatus such as a mask aligner or a stepper because it is possible to uniformly irradiate the entire exposure surface with a parallel light beam or to precisely align the mask with the substrate.

A pattern can be obtained by dissolving a predetermined portion, for example, an unexposed portion, and developing the exposed film obtained by exposing the dried film to a developing solution. As the developing solution, an organic solvent may be used. However, an aqueous solution of an alkaline compound is preferably used because an exposed portion of the exposed film is not easily dissolved or swelled by a developing solution and a pattern of a good shape can be obtained.

The developing method may be paddle method, dipping method, spray method, or the like. Further, the substrate may be inclined at an arbitrary angle at the time of development.

It is preferable to rinse after development.

Examples of the alkaline compound include sodium hydroxide, potassium hydroxide, disodium hydrogenphosphate, sodium dihydrogenphosphate, ammonium dihydrogenphosphate, ammonium dihydrogenphosphate, potassium dihydrogenphosphate, sodium silicate, potassium silicate, sodium carbonate, potassium carbonate, Inorganic alkaline compounds such as potassium hydrogen, sodium borate, potassium borate and ammonia;

Monoethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine, diisopropylamine, diisopropylamine, diisopropylamine, And organic alkaline compounds such as ethanolamine.

Among them, potassium hydroxide, sodium hydrogencarbonate and tetramethylammonium hydroxide are preferable.

The concentration of these inorganic and organic alkaline compounds in the aqueous solution is preferably 0.01 to 10 mass%, and more preferably 0.03 to 5 mass%.

The aqueous solution of the alkaline compound may contain a surfactant.

Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene aryl ethers, polyoxyethylene alkyl aryl ethers, other polyoxyethylene derivatives, oxyethylene / oxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid Nonionic surfactants such as esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene fatty acid esters and polyoxyethylene alkylamines;

Anionic surfactants such as sodium lauryl alcohol sulfate ester, sodium oleyl alcohol sulfate ester, sodium lauryl sulfate, ammonium lauryl sulfate, sodium dodecylbenzenesulfonate and sodium dodecylnaphthalenesulfonate;

Cationic surfactants such as stearylamine hydrochloride and lauryltrimethylammonium chloride, and the like.

The concentration of the surfactant in the aqueous solution of the alkaline compound is preferably 0.01 to 10 mass%, more preferably 0.05 to 8 mass%, and particularly preferably 0.1 to 5 mass%.

By baking the pattern obtained as described above, a thermally cured pattern can be obtained. The baking temperature is usually 25 ° C or higher and 230 ° C or lower, preferably 25 ° C or higher and 200 ° C or lower, more preferably 25 ° C or higher and 160 ° C or lower, and further preferably 25 ° C or higher and 120 ° C or lower. The baking time is usually 1 to 300 minutes, preferably 1 to 180 minutes, and more preferably 1 to 60 minutes.

The pattern thus obtained is useful as, for example, a photo-spacer used in a liquid crystal display, a patternable overcoat, and a color filter. The photosensitive resin composition of the present invention can be suitably used for forming a film or a pattern to be a pixel of a liquid crystal display device or an image sensor and can be suitably used as a color filter, An array substrate, and a display device including these color filters and / or array substrates, for example, a liquid crystal display device, an organic EL device, and a solid-state imaging device.

Example

Hereinafter, the colored photosensitive resin composition of the present invention will be described in more detail by examples. In the examples, "% " and " part " are by mass% and mass part, unless otherwise specified.

<Synthesis of Binder Resin (A1) Solution>

67 parts of propylene glycol monomethyl ether acetate and 33 parts of propylene glycol monomethyl ether were placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, stirred while replacing nitrogen and heated to 120 deg. Subsequently, Perbutyl O was added to the monomer mixture consisting of 11 parts of dicyclopentanyl acrylate, 31 parts of benzyl methacrylate and 23 parts of methacrylic acid in a ratio of 1 part based on 100 parts of the monomer mixture. This was dropped from the dropping funnel into the flask over 2 hours and further stirred at 120 ° C for 2 hours to obtain a copolymer. Then, 10 parts of glycidyl methacrylate, 0.46 part of triphenylphosphine and 0.08 part of methylhydroquinone were added to the solution of the copolymer, and the reaction was continued at 120 캜 to obtain a copolymer having a solid content of acid value of 150 mg -KOH / g, the reaction was terminated and 75 parts of propylene glycol monomethyl ether acetate and 5 parts of propylene glycol monomethyl ether were added to obtain a copolymer having a weight average molecular weight (Mw) of 30 × 10 ³ and an acid value of 150 mg-KOH / g in 30% by mass of the binder resin (A1). The binder resin (A1) has the following structural units.

<Synthesis of Binder Resin (A2) Solution>

67 parts of propylene glycol monomethyl ether acetate and 33 parts of propylene glycol monomethyl ether were placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, stirred while replacing nitrogen and heated to 120 deg. Subsequently, Perbutyl O was added to the monomer mixture consisting of 10 parts of dicyclopentanyl acrylate, 34 parts of benzyl methacrylate and 20 parts of methacrylic acid in a ratio of 1 part based on 100 parts of the monomer mixture. This was dropped from the dropping funnel into the flask over 2 hours and further stirred at 120 ° C for 2 hours to obtain a copolymer. Then, 10 parts of glycidyl methacrylate, 0.44 part of triphenylphosphine and 0.08 part of methylhydroquinone were added to the solution of the copolymer, and the reaction was continued at 120 ° C to obtain a copolymer having a solid content of 130 mg -KOH / g, the reaction was terminated and 74 parts of propylene glycol monomethyl ether acetate and 5 parts of propylene glycol monomethyl ether were added to obtain a copolymer having a weight average molecular weight (Mw) of 30 × 10 ³ and an acid value of 130 mg-KOH / g of a binder resin (A2) in an amount of 30% by mass. The binder resin (A2) has the following structural unit.

<Synthesis of Binder Resin (A3) Solution>

413 parts of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a gas inlet tube. Thereafter, nitrogen gas was introduced into the flask through a gas inlet tube, the atmosphere in the flask was replaced with nitrogen gas, and 144 parts of benzyl methacrylate, 30 parts of dicyclopentanyl acrylate, 35 parts of methacrylic acid and 0.1 part of azobisisobutyl And 5.2 parts of ronitryl was added thereto, followed by stirring at 100 ° C for 5 hours. Thereafter, the solution was cooled to room temperature to obtain a solution containing 33.6% by mass of a binder resin (A3) having a weight average molecular weight (Mw) of 10 × 10 ³ and an acid value of 110 mg-KOH / g. The resin (A3) has the following structural units.

<Synthesis of Binder Resin (A4) Solution>

In a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer, a nitrogen stream was appropriately flowed, and the flask was purged with nitrogen atmosphere. 371 parts of propylene glycol monomethyl ether acetate was added and heated to 85 DEG C with stirring. Subsequently, 54 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan- Acrylate, 81 parts of vinyl toluene (isomer mixture) and 80 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. On the other hand, a solution prepared by dissolving 30 parts of polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the end of the dropwise addition of the initiator solution, the mixture was kept at the same temperature for 4 hours, and then cooled to room temperature to obtain 37.5 mass parts of a binder resin (A4) having a weight average molecular weight (Mw) of 10 x 10 &lt; ³ & %, And a B-type viscosity (23 ° C) of 246 mPas. The binder resin (A4) has the following structural units.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin obtained in Synthesis Example were measured by the GPC method under the following conditions.

Apparatus: K2479 (manufactured by Shimadzu Corporation)

Column: SHIMADZU Shim-pack GPC-80M

Column temperature: 40 DEG C

Solvent: THF (tetrahydrofuran)

Flow rate: 1.0 ml / min

Detector: RI

&Lt; Synthesis of Compound Represented by Formula (F1) >

40.5 parts of the compound represented by the formula (IV-1) and 60.5 parts of 2,6-xylidine (manufactured by Tokyo Kasei Corporation) were mixed under light shielding conditions, and the mixture was heated in 150 parts of N-methylpyridone Lt; / RTI &gt; The obtained reaction solution was cooled to room temperature, added to a mixed solution of 1200 parts of water and 75 parts of 35% hydrochloric acid, and stirred at room temperature for 1 hour to precipitate crystals. The precipitated crystals were collected as a residue of suction filtration, washed with 100 parts of methanol, and dried under reduced pressure at 60 DEG C overnight to obtain 49 parts of a compound represented by the formula (IV-2). The yield was 85%.

Subsequently, 28.8 parts of the compound represented by the formula (IV-2), 21.6 parts of 1-bromopropane and 24.2 parts of potassium carbonate were added to 144 parts of N-methylpyridone, and the mixture was stirred at 90 ° C for 4 hours. The obtained reaction solution was cooled to room temperature, concentrated, and added to 560 parts of water. The mixture was stirred at 10 to 15 DEG C for 1 hour, and crystals were precipitated. The precipitated crystals were collected as a residue of suction filtration, dried, washed with 1000 parts of ion-exchanged water, and dried under reduced pressure at 60 ° C overnight to obtain 30.0 parts of a compound represented by the formula (F1). The yield was 91%.

Identification of the compound represented by the formula (F1)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 659.3

                        Exact Mass: 658.3

Example  One

[Preparation of photosensitive resin composition 1]

Colorant (F): C.I. Pigment Red 242 15 parts,

Colorant (F): C.I. Pigment Red 177 20 parts,

14 parts of an acrylic pigment dispersant,

33.3 parts of a binder resin (A1) solution

(Binder resin (A1) 10 parts), and

Solvent (E): Propylene glycol monomethyl ether acetate 191 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

254 parts of the binder resin (A1) solution

(76.2 parts of binder resin (A1));

Polymerizable compound (B): glycerol 1,3-diglycerolate diacrylate

(GDDA; manufactured by Aldrich) 37 parts;

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; Manufactured by BASF Japan Ltd.) 3.7 parts;

Polymerization initiator (C): bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide

[Irgacure (R) 819; Manufactured by BASF Japan Ltd.) 7.4 parts;

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; (Manufactured by Nippon Kayaku Co., Ltd.) 3.7 parts;

Extender pigment (D) Dispersion: PMA-ST; Manufactured by Nissan Kagaku Co., Ltd.

(30 mass% of silicon oxide, 69.5 mass% of propylene glycol monoethyl ether acetate and 0.5 mass% of methanol) (hereinafter the same) 41 parts;

Solvent (E): 398 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; 0.5 part (manufactured by Toray Dow Corning Co., Ltd.)

To obtain a photosensitive resin composition 1.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 1 was 93.3% by mass and the ratio of propylene glycol monomethyl ether (solvent (E2) Respectively. The mass ratio (binder resin (A1) / polymerizable compound (B)) of the binder resin (A1) and the polymerizable compound (B) was 70/30.

Example  2

[Preparation of photosensitive resin composition 2]

Colorant (F): C.I. Pigment Green 58 43 parts,

Colorant (F): C.I. Pigment Yellow 138 24 parts

12 parts of an acrylic pigment dispersant,

86.7 parts of a binder resin (A1) solution

(Binder resin (A1) 26 parts), and

Solvent (E): Propylene glycol monomethyl ether acetate 390 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

117 parts of the binder resin (A1) solution

(Binder resin (A1) 35.1 parts);

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; 41 parts (manufactured by Nippon Kayaku Co., Ltd.);

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; 10 parts by BASF Japan Co., Ltd.);

Polymerization initiator (C): bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide

[Irgacure] (R) 819; Manufactured by BASF Japan Ltd.) 8.1 parts;

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; 10 parts by weight (manufactured by Nippon Kayaku Co., Ltd.);

Extender pigment (D) Dispersion: PMA-ST; 34 parts by Nissan Kagaku KK;

Solvent (E): 307 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Doraikon SH8400; 0.5 part (manufactured by Toray Dow Corning Co., Ltd.)

To obtain a photosensitive resin composition 2.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 2 was 96.9 mass%, the proportion of propylene glycol monomethyl ether (solvent (E2) Respectively. The mass ratio (binder resin (A1) / polymerizable compound (B)) of the binder resin (A1) and the polymerizable compound (B) was 60/40.

Example  3

[Preparation of photosensitive resin composition 3]

Colorant (F): C.I. Pigment Blue 15: 6 27 parts,

Colorant (F): C.I. 0.5 parts of Pigment Violet 23,

10 parts of an acrylic pigment dispersant,

27.7 parts of a binder resin (A1) solution

(Binder resin (A1) 8.3 parts), and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

227 parts of the binder resin (A1) solution

(68.1 parts of binder resin (A1));

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; (Manufactured by Nippon Kayaku Co., Ltd.);

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; Manufactured by BASF Japan Ltd.) 5.4 parts;

Polymerization initiator (C): bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide

[Irgacure (R) 819; Manufactured by BASF Japan Ltd.) 8.6 parts;

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; (Manufactured by Nippon Kayaku) 4.3 parts;

Extender pigment (D) Dispersion: PMA-ST; 36 parts, manufactured by Nissan Kagaku Co., Ltd.;

Solvent (E): 497 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; 0.5 part (manufactured by Toray Dow Corning Co., Ltd.)

To obtain a photosensitive resin composition 3.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 3 was 94.2 mass%, the proportion of propylene glycol monomethyl ether (solvent (E2)) was 5.8 mass% Respectively. The mass ratio (binder resin (A1) / polymerizable compound (B)) of the binder resin (A1) and the polymerizable compound (B) was 70/30.

Example  4

[Preparation of photosensitive resin composition 4]

Colorant (F): C.I. Pigment Blue 15: 6 27 parts,

Colorant (F): C.I. 0.5 parts of Pigment Violet 23,

10 parts of an acrylic pigment dispersant,

24.7 parts of a binder resin (A2) solution

(Binder resin (A2), 7.4 parts), and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

Binder resin (A2) solution 191 parts

(Binder resin (A2) 57.3 parts);

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; 43 parts manufactured by Nippon Kayaku Co., Ltd.;

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; Manufactured by BASF Japan Ltd.) 5.4 parts;

Polymerization initiator (C): bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide

[Irgacure (R) 819; Manufactured by BASF Japan Ltd.) 8.6 parts;

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; (Manufactured by Nippon Kayaku) 4.3 parts;

Extender pigment (D) Dispersion: PMA-ST; 36 parts, manufactured by Nissan Kagaku Co., Ltd.;

Solvent (E): 530 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; 0.5 part (manufactured by Toray Dow Corning Co., Ltd.)

To obtain a photosensitive resin composition 4.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition was 95.1 mass% and the ratio of propylene glycol monomethyl ether (solvent (E2)) was 4.9 mass% . The mass ratio (binder resin (A2) / polymerizable compound (B)) of the binder resin (A2) and the polymerizable compound (B) was 60/40.

Example  5

[Preparation of photosensitive resin composition 5]

Colorant (F): C.I. Pigment Blue 15: 6 27 parts,

Colorant (F): C.I. 0.5 parts of Pigment Violet 23,

10 parts of an acrylic pigment dispersant,

24.7 parts of a binder resin (A1) solution

(Binder resin (A1), 7.4 parts), and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

245 parts of the binder resin (A1) solution

(Binder resin (A1) 73.5 parts);

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; (Manufactured by Nippon Kayaku Co., Ltd.);

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; Manufactured by BASF Japan Ltd.) 5.4 parts;

Polymerization initiator (C): bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide

[Irgacure (R) 819; Manufactured by BASF Japan Ltd.) 8.6 parts;

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; (Manufactured by Nippon Kayaku) 4.3 parts;

Extender pigment (D) Dispersion: PMA-ST; 36 parts, manufactured by Nissan Kagaku Co., Ltd.;

Solvent (E): 494 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; 0.5 part (manufactured by Toray Dow Corning Co., Ltd.)

To obtain a photosensitive resin composition 5.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition was 93.8 mass% and the proportion of propylene glycol monomethyl ether (solvent (E2)) was 6.2 mass% . The mass ratio (binder resin (A1) / polymerizable compound (B)) of the binder resin (A1) and the polymerizable compound (B) was 75/25.

Example  6

[Preparation of photosensitive resin composition 6]

Colorant (F): C.I. Pigment Blue 15: 6 27 parts,

Colorant (F): C.I. 0.5 parts of Pigment Violet 23,

10 parts of an acrylic pigment dispersant,

27.7 parts of a binder resin (A1) solution

(Binder resin (A1) 8.3 parts), and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

227 parts of the binder resin (A1) solution

(68.1 parts of binder resin (A1));

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; (Manufactured by Nippon Kayaku Co., Ltd.);

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; BASF Japan Ltd.) 5.8 parts;

Polymerization initiator (C): bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide

[Irgacure (R) 819; 9.4 parts; manufactured by BASF Japan Co., Ltd.);

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; 4.7 parts; manufactured by Nippon Kayaku Co., Ltd.);

Extender pigment (D) Dispersion: PMA-ST; 36 parts, manufactured by Nissan Kagaku Co., Ltd.;

Solvent (E): Propylene glycol monomethyl ether 190 parts

Solvent (E): 317 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; 0.5 part (manufactured by Toray Dow Corning Co., Ltd.)

To obtain a photosensitive resin composition 6.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 6 was 71.2 mass%, the proportion of propylene glycol monomethyl ether (solvent (E2)) was 28.9 mass% Respectively. The mass ratio (binder resin (A1) / polymerizable compound (B)) of the binder resin (A1) and the polymerizable compound (B) was 70/30.

Comparative Example  One

[Preparation of photosensitive resin composition 7]

Japanese Patent Application Laid-Open No. 2011-221310 A photosensitive resin composition 7 was obtained in accordance with Example 1.

Example  7

[Preparation of photosensitive resin composition 8]

Colorant (F): C.I. Pigment Blue 15: 6 26 parts,

Colorant (F): 6.4 parts of a compound represented by the formula (F1)

9.0 parts of an acrylic pigment dispersant,

Binder resin (A4) solution 26.7 parts

(10 parts of binder resin (A4)),

Solvent (E): 31 parts of 4-hydroxy-4-methyl-2-pentanone, and

Solvent (E): Propylene glycol monomethyl ether acetate 282 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

108 parts of the binder resin (A3) solution

(36.3 parts of binder resin (A3));

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; (Manufactured by Nippon Kayaku Co., Ltd.);

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; 9.3 parts by BASF Japan Co., Ltd.);

Polymerization initiator (C): 2-Methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-

[Irgacure 907; 1.9 parts; manufactured by BASF Japan Ltd.);

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; 5.6 parts; manufactured by Nippon Kayaku Co., Ltd.);

Extender pigment (D) Dispersion: PMA-ST; 37 parts, manufactured by Nissan Kagaku Co., Ltd.;

Solvent (E): 168 parts of 4-hydroxy-4-methyl-2-pentanone

Solvent (E): 260 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; (Manufactured by Toray Dow Corning Co., Ltd.) 0.1 part

To obtain a photosensitive resin composition 8.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 8 was 75.7% by mass, and the content of 4-hydroxy- )) Was 24.3% by mass. The mass ratio (binder resin (A3) / binder resin (A4) / polymerizable compound (B)) of the binder resin (A3), the binder resin (A4) and the polymerizable compound (B) was 11/39/50 .

Example  8

[Preparation of photosensitive resin composition 9]

Colorant (F): C.I. Pigment Blue 15: 6 26 parts,

Colorant (F): 6.4 parts of a compound represented by the formula (F1)

9.0 parts of an acrylic pigment dispersant,

Binder resin (A4) solution 26.7 parts

(10 parts of binder resin (A4)),

Solvent (E): 31 parts of 4-hydroxy-4-methyl-2-pentanone and

Solvent (E): Propylene glycol monomethyl ether acetate 282 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

Binder resin (A4) solution 97 parts

(36.4 parts of binder resin (A4));

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; (Manufactured by Nippon Kayaku Co., Ltd.);

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; 9.3 parts by BASF Japan Co., Ltd.);

Polymerization initiator (C): 2-Methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-

[Irgacure 907; 1.9 parts; manufactured by BASF Japan Ltd.);

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; 5.6 parts; manufactured by Nippon Kayaku Co., Ltd.);

Extender pigment (D) Dispersion: PMA-ST; 37 parts, manufactured by Nissan Kagaku Co., Ltd.;

Solvent (E): 168 parts of 4-hydroxy-4-methyl-2-pentanone

Solvent (E): 272 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; (Manufactured by Toray Dow Corning Co., Ltd.) 0.1 part

To obtain a photosensitive resin composition 9.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 9 was 75.7% by mass, and the content of 4-hydroxy- )) Was 24.3% by mass. The mass ratio of the binder resin (A4) to the polymerizable compound (B) (binder resin (A4) / polymerizable compound (B)) was 50/50.

Comparative Example  2

[Preparation of photosensitive resin composition 10]

Colorant (F): C.I. Pigment Blue 15: 6 26 parts,

Colorant (F): 6.4 parts of a compound represented by the formula (F1)

4.3 parts of an acrylic pigment dispersant,

Binder resin (A4) solution 32 parts

(Binder resin (A4) 12 parts),

Solvent (E): 29 parts of 4-hydroxy-4-methyl-2-pentanone and

Solvent (E): Propylene glycol monomethyl ether acetate 243 parts

A pigment dispersion in which the pigment is sufficiently dispersed by using a bead mill;

Binder resin (A4) solution 121 parts

(Binder resin (A4) 45.4 parts);

Polymerizable compound (B): dipentaerythritol hexaacrylate

[KAYARAD (TM) DPHA; 52 parts manufactured by Nippon Kayaku Co., Ltd.;

Polymerization initiator (C): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-

[Irgacure (R) OXE-01; 11 parts by BASF Japan Ltd.);

Polymerization initiator (C): 2-Methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-

[Irgacure 907; 2.1 parts by BASF Japan Co., Ltd.);

Polymerization initiator (C): Diethyl thioxanthone

[KAYACURE (TM) DETX-S; (Manufactured by Nippon Kayaku Co., Ltd.);

Solvent (E): 168 parts of 4-hydroxy-4-methyl-2-pentanone

Solvent (E): 320 parts of propylene glycol monomethyl ether acetate; And

Surfactant: polyether-modified silicone oil

[Toray Silicone SH8400; (Manufactured by Toray Dow Corning Co., Ltd.) 0.1 part

To obtain a photosensitive resin composition 10.

The proportion of propylene glycol monomethyl ether acetate (solvent (E1)) in the total solvent (E) in the obtained photosensitive resin composition 10 was 75.8 mass%, and the content of 4-hydroxy-4-methyl- )) Was 24.2% by mass. The mass ratio of the binder resin (A4) to the polymerizable compound (B) (binder resin (A4) / polymerizable compound (B)) was 50/50.

<Fabrication of pattern>

The photosensitive resin composition was coated on a square glass substrate having one side of 2 inches by spin coating, and then prebaked at 100 캜 for 3 minutes to form a dried film. After cooling, the resist film was exposed to a dry film formed on the substrate through a quartz glass photomask so that the distance between the film and the dry film was 100 mu m, using an exposure machine (TME-150 RSK; (Manufactured by Topcon Co., Ltd.) at an exposure amount of 50 mJ / cm &lt; 2 &gt; (based on 365 nm) in an air atmosphere. As the photomask, a 50 占 퐉 line and space pattern was formed. After the light irradiation, the obtained exposure film was immersed in an aqueous developer containing 0.12% of a nonionic surfactant and 2% of sodium carbonate at 24 DEG C for 60 seconds for development, rinsed and postbaked in an oven at 230 DEG C for 30 minutes And a pattern was obtained.

<Evaluation of resolution>

The obtained pattern was observed with a laser microscope (manufactured by Carl Zeiss, Axio Imager MAT), and the minimum resolution was determined as the resolution. The higher the resolution, the more usable for the production of high-definition color filters.

&Lt; Evaluation of development unevenness &

The obtained pattern was observed with a laser microscope (Axio Imager MAT manufactured by Carl Zeiss Co.), and those having no water unevenness were evaluated as &amp; cir &amp; (no developing unevenness was observed) and those having water unevenness were evaluated as x (developing unevenness). When development unevenness is seen, color unevenness occurs when used for manufacturing a color filter.

<Evaluation of solvent resistance>

One milliliter of propylene glycol monomethyl ether acetate was added dropwise to the pattern formed on the substrate, and the mixture was kept at rest for 30 seconds and then rotated at a rotation speed of 1000 rpm for 10 seconds using a spin coater to remove the patterned propylene glycol monomethyl ether acetate .

The film thickness retention ratio was calculated from the film thickness values measured before and after the contact with propylene glycol monomethyl ether acetate according to the following formula. The higher the film thickness retention ratio is, the better the curability is, and when used in the production of a color filter, the color mixing can be prevented and the development unevenness is improved.

(Film thickness retention) (%) = (film thickness after contact) / (film thickness before contact)

&Lt; Fabrication of front exposure film &

A PET film (Lumira 75-T60 manufactured by Toray Industries, Inc.) was bonded to a square glass plate having a side of 2 inches on each side to prepare a substrate. On the PET film side of the substrate, the photosensitive resin composition was applied by a spin coat method and prebaked on a hot plate at 80 DEG C for 2 minutes. After cooling down, on the entire surface of the dried film formed on the substrate, an exposure machine (TME-150RSK; (Manufactured by Topcon Co., Ltd.) at an exposure amount of 150 mJ / cm &lt; 2 &gt; (based on 365 nm) in an air atmosphere. After light irradiation, the resist film was immersed in an aqueous developing solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 DEG C for 50 seconds, developed and washed with pure water to obtain a front exposure film. The obtained front exposure developing film was measured with a film thickness measuring device [DEKTAK3; (Manufactured by ULVAC Co., Ltd.), and found to be 2 탆.

&Lt; Crosscut test >

The obtained front exposure film was subjected to a tape peeling test (cross-cut test) in accordance with JIS K5600-5-6 to evaluate the adhesion to the PET film. The results are shown in Table 1.

<Pencil hardness>

The obtained pencil hardness according to JIS-K5400 was measured using a pencil scratch hardness tester (manufactured by Yasuda Seiki Seisakusho Co., Ltd.). The load was 1,000 g.

&Lt; Evaluation of stickiness &

A photosensitive resin composition was applied to a square PET film (Rumira 75-T60, manufactured by Toray Co., Ltd.) having a side length of 5 cm using a film applicator (AP75 manufactured by Tai Yuki Kaisha K.K.) Lt; / RTI &gt; for 2 minutes. After cooling, a PET film (Lumira 75-T-60 manufactured by Toray Industries, Inc.) having another 5 cm side was pressed onto the dried film formed on the square PET film with the side of 5 cm on one side, The film was peeled off. (No stickiness was observed), no dried film was uneven and no peeling was observed on the peeled PET film, and the peeling of the peeled PET film was evaluated as x (stickiness) Respectively. When stickiness is seen, color unevenness occurs when used in the production of color filters.

INDUSTRIAL APPLICABILITY According to the present invention, it becomes possible to provide a photosensitive resin composition which gives a dry film having satisfactory low tackiness and which gives a pattern having satisfactory hardness.

By using the photosensitive resin composition of the present invention, it is possible to obtain a pattern with high resolution and improved unevenness in development. The pattern obtained by the present invention is useful as a display color filter for use in a liquid crystal display, an organic EL display, an electronic paper display, or the like.

Claims (10)

A photosensitive resin composition comprising a binder resin (A), a polymerizable compound (B), a polymerization initiator (C), an extender pigment (D) and a solvent (E), wherein the solvent (E) has a solubility parameter of 8.0 to 9.1 solvents (E2) (cal / ㎤) 1/2 of the solvent (E1) for, with respect to the solvent (E), and contains 70 to 99% by weight, the solubility parameter is 9.2 ~ 11.0 (cal / ㎤) 1/2 Is contained in an amount of 1 to 30% by mass with respect to the solvent (E). The photosensitive resin composition according to claim 1, wherein the polymerization initiator (C) is an oxime compound. The photosensitive resin composition according to claim 1 or 2, wherein the acid value of the binder resin (A) is 50 to 180 mg-KOH / g. The toner according to any one of claims 1 to 3, wherein the content of the binder resin (A) is 30 to 80 mass% (based on 100 parts by mass of the total amount of the binder resin (A) Lt; / RTI &gt; The photosensitive resin composition according to any one of claims 1 to 4, wherein the extender pigment (D) is silicon oxide. The photosensitive resin composition according to any one of claims 1 to 5, further comprising a colorant. The photosensitive resin composition according to claim 6, wherein the coloring agent is a coloring agent comprising a pigment. The photosensitive resin composition according to claim 6 or 7, wherein the colorant is a colorant comprising a dye. A pattern formed by the photosensitive resin composition according to any one of claims 1 to 8. A display device comprising the pattern according to claim 9.