TW202307033A - Photosensitive resin composition, cured product, color filter, and member for display device or display device - Google Patents

Abstract

The present invention provides a photosensitive resin composition having excellent storage stability, excellent curing reactivity, and excellent solvent resistance of cured products. The photosensitive resin composition includes an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The alkali-soluble resin is a copolymer including a structural unit (A) derived from an unsaturated carboxylic acid or an anhydride thereof, and a structural unit (B) derived from an epoxy compound represented by the following formula (b1).

Description

Photosensitive resin composition, cured product, color filter, and member for display device or display device

The present invention relates to a photosensitive resin composition, a cured product, a color filter, and a member for a display device or a display device. This application claims the priority of Japanese Patent Application No. 2021-063808 and Japanese Patent Application No. 2021-063809 filed in Japan on April 2, 2021, and the contents thereof are incorporated herein.

As a photosensitive resin composition used for producing an insulating film, a color filter protective film, a microlens, etc., a resin composition containing an alkali-soluble resin, a photopolymerizable compound, and a photopolymerization initiator is known. In addition, as a colored photosensitive resin composition used in the production of color filters, a resin composition containing an alkali-soluble resin, a colorant (pigment or dye), a photopolymerizable compound, and a photopolymerization initiator is known.

Patent Document 1 discloses a photosensitive resin composition containing, as an alkali-soluble resin, a copolymer containing methacrylic acid and glycidyl methacrylate as constituent monomers. Patent Document 2 discloses a photosensitive resin composition containing, as an alkali-soluble resin, a copolymer comprising methacrylic acid and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate as constituent monomers. .

In addition, Patent Document 3 discloses a colored photosensitive resin composition containing, as an alkali-soluble resin, a copolymer containing methacrylic acid and benzyl methacrylate as constituent monomers. Patent Document 4 discloses a colored photosensitive resin composition containing, as an alkali-soluble resin, a copolymer containing methacrylic acid and glycidyl methacrylate as constituent monomers. Patent Document 5 discloses a colored photosensitive resin composition containing ^, as an alkali-soluble resin. Prior Art Documents Patent Documents

Patent Document 1: Japanese Patent Laid-Open No. 11-133600 Patent Document 2: Japanese Patent Laid-Open No. 2006-171160 Patent Document 3: Japanese Patent Application Laid-Open No. 9-134004 Patent Document 4: Japanese Patent Laid-Open No. 2011-237728 Patent Document 5: Japanese Patent Laid-Open No. 2007-333847

The problem to be solved by the invention

However, the photosensitive resin composition disclosed in Patent Document 1 has the disadvantages of low stability and increased viscosity (viscosity) over time. Furthermore, the solvent resistance of the cured product is not sufficient. The photosensitive resin composition disclosed in Patent Document 2 has excellent storage stability, but has poor reactivity with carboxylic acid, and requires a curing temperature of 230° C. or higher.

In addition, the colored photosensitive resin composition disclosed in Patent Document 3 has the disadvantage of low solvent resistance of its cured product. The colored photosensitive resin composition disclosed in Patent Document 4 has the following disadvantages: low stability, and viscosity increases (viscosity) with time. Furthermore, the solvent resistance of the cured product is not sufficient. The colored photosensitive resin composition disclosed in Patent Document 5 has excellent storage stability, but has poor reactivity with carboxylic acid, and requires a curing temperature of 230° C. or higher.

Therefore, an object of the present invention is to provide a photosensitive resin composition which is excellent in storage stability and curing reactivity, and which can obtain a cured product excellent in solvent resistance by curing. In addition, another object of the present invention is to provide a cured product of the photosensitive resin composition having the above characteristics, a color filter as the cured product, and a member for a display device or a display device including the color filter. means of solving problems

The inventors of the present invention have made diligent research in order to achieve the above object, and as a result, found that if the photosensitive resin composition using a copolymer comprising a specific structural unit as an alkali-soluble resin has excellent storage stability, even at a relatively low temperature. Hardened, and the hardened product has excellent solvent resistance. The invention of the present invention was accomplished based on these findings.

That is, the present invention provides a photosensitive resin composition comprising an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent,

（式中，R ^b1表示氫原子或碳數1至7之烷基。R ^b2表示可含有雜原子之2價烴基。R ^b3表示具有2個以上之環氧基之2價有機基。） The said alkali-soluble resin is a copolymer containing the structural unit (A) derived from an unsaturated carboxylic acid or its anhydride, and the structural unit (B) derived from the epoxy compound represented by following formula (b1). ◎[Chemical Formula 1]

(In the formula, R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. ^{R b2} represents a divalent hydrocarbon group that may contain a heteroatom. R ^b3 represents a divalent organic group having two or more epoxy groups.)

（式中，R ^b1表示氫原子或碳數1至7之烷基。R ^b2表示可含有雜原子之2價烴基。R ^b5相同或不同地表示氫原子或碳數1至6之烷基。R ^b6相同或不同地表示單鍵或可含有雜原子之2價烴基。nb2及nb3分別表示0以上之整數，nb2與nb3之和為2以上。另外，環氧乙烷環可具有碳數1至6之烷基。[ ]內之2種基不一定必須按照式(b3)所示之順序排列。） ◎[化學式3]

（式中，R ^b1表示氫原子或碳數1至7之烷基。R ^b2表示可含有雜原子之2價烴基。R ^b7相同或不同地表示氫原子或碳數1至6之烷基。R ^b8為鍵結於環Z上之基，且相同或不同地表示單鍵或可含有雜原子之2價烴基。m表示1至3之整數。環Z表示碳數3至20之脂環式烴環。nb4表示2以上之整數。另外，環氧乙烷環可具有碳數1至6之烷基。另外，環Z可具有碳數1至6之烷基作為R ^b7及R ^b8以外之基。） The aforementioned epoxy compound is preferably at least one selected from the group consisting of compounds represented by the following formula (b3) and compounds represented by the following formula (b4). ◎[Chemical Formula 2]

(wherein, R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. R ^b2 represents a divalent hydrocarbon group which may contain a heteroatom. R ^b5 identically or differently represents a hydrogen atom or an alkyl group having 1 to 6 carbons. R ^b6 identically or differently represent a single bond or a divalent hydrocarbon group that may contain a heteroatom. nb2 and nb3 each represent an integer of 0 or more, and the sum of nb2 and nb3 is 2 or more. In addition, the oxirane ring may have a carbon number of 1 to 6. The two groups in [ ] do not necessarily have to be arranged in the order shown in formula (b3).) ◎[Chemical formula 3]

(wherein, R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. R ^b2 represents a divalent hydrocarbon group which may contain a heteroatom. R ^b7 identically or differently represents a hydrogen atom or an alkyl group having 1 to 6 carbons. R ^b8 is a group bonded to the ring Z, and the same or different represents a single bond or a divalent hydrocarbon group that may contain a heteroatom. m represents an integer from 1 to 3. Ring Z represents an alicyclic formula with 3 to 20 carbon atoms Hydrocarbon ring. nb4 represents an integer of 2 or more. In addition, the oxirane ring may have an alkyl group having 1 to 6 carbons. In addition, the ring Z may have an alkyl group having 1 to 6 carbons as other than R ^b7 and R ^b8 base.)

（式中，R ¹¹表示氫原子或碳數1至7之烷基。R ¹²表示可含有雜原子之1價烴基。X表示雜原子。） The aforementioned copolymer preferably further includes a structural unit (C) derived from at least one compound selected from the group consisting of the following (c1) to (c4). (c1) Styrene which may be substituted with an alkyl group (c2) N-substituted maleimide (c3) N-vinyl compound (c4) Unsaturated carboxylic acid derivative represented by the following formula (2) ◎[Chemical Formula 4]

(In the formula, ^R11 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. ^R12 represents a monovalent hydrocarbon group that may contain a heteroatom. X represents a heteroatom.)

The aforementioned copolymer is preferably such that the content of the structural unit (A) relative to all structural units of the copolymer is 2 to 50% by weight, the content of the structural unit (B) is 10 to 98% by weight, and the content of the structural unit (C) is 0 to 80% by weight.

It is preferable that the said photosensitive resin composition further contains a colored material.

The aforementioned colored materials are preferably pigments and/or dyes.

In addition, the present invention provides a cured product of the aforementioned photosensitive resin composition.

In addition, the present invention provides a color filter as the aforementioned cured product.

Moreover, this invention provides the member for display devices or a display device provided with the said color filter. Invention effect

According to the invention of the present invention, a photosensitive resin composition having excellent storage stability, excellent curing reactivity, and excellent solvent resistance of a cured product can be provided. In addition, a cured product of the photosensitive resin composition having the above characteristics, a color filter as the cured product, and a member for a display device or a display device including the above color filter can be provided.

The photosensitive resin composition of the present invention contains an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The application of the aforementioned photosensitive resin composition is not particularly limited, for example, it can be used as a material for forming an insulating film, a color filter protective film, a microlens, etc., especially a transparent film. It is preferable that the said photosensitive resin composition further contains a colored material. The application of the photosensitive resin composition containing a colored material (sometimes referred to as "colored photosensitive resin composition") is not particularly limited, for example, it is used as a colored pattern forming material. ＜Alkali-soluble resin＞

In this invention, the copolymer containing the structural unit (A) derived from an unsaturated carboxylic acid or its anhydride, and the structural unit (B) derived from the epoxy compound represented by said formula (b1) is used as alkali-soluble resin. The aforementioned copolymer may further include a structural unit (C) derived from at least one compound selected from the group consisting of the aforementioned (c1) to (c4). In addition, a structural unit (D) described later may be further included as a structural unit other than the structural units (A) to (C). [Structural unit (A)]

The structural unit (A) can be introduced into the copolymer by polymerizing an unsaturated carboxylic acid or its anhydride (a) and the epoxy compound (b) represented by the aforementioned formula (b1).

The unsaturated carboxylic acid or its anhydride (a) is not particularly limited, and examples thereof include: α,β-unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; itaconic acid, maleic acid , fumaric acid and other α, β-unsaturated dicarboxylic acids; methacrylic anhydride and other α, β-unsaturated monocarboxylic acid anhydrides; maleic anhydride, itaconic anhydride and other α, β-unsaturated Anhydrides of dicarboxylic acids. Among these, acrylic acid and methacrylic acid are particularly preferable from the viewpoint of copolymerizability and developability. The unsaturated carboxylic acid or its anhydride (a) can be used individually or in combination of 2 or more types.

The ratio (content) of the structural unit (A) in the copolymer is not particularly limited, for example, it is preferably 2 to 50% by weight, more preferably 3 to 40% by weight, relative to all the structural units constituting the copolymer, It is further preferably 5 to 25% by weight, especially preferably 10 to 20% by weight. There exists a tendency for the solvent resistance of hardened|cured material to be excellent by making the ratio of a structural unit (A) into the said range. Since excessive image development can be suppressed by making the ratio of a structural unit (A) below the said upper limit, it exists in the tendency which is excellent in solvent resistance. In addition, in the present invention, the proportion of the structural unit in the copolymer is based on the weight of the compound (monomer) used for the copolymerization. For example, the ratio of the structural unit (A) in the copolymer refers to the ratio of the amount of unsaturated carboxylic acid or its anhydride (a) used to the total amount (100% by weight) of the compounds used for copolymerization. [Structural unit (B)]

式(b1)中，R ^b1表示氫原子或碳數1至7之烷基。R ^b2表示可含有雜原子之2價烴基。R ^b3表示具有2個以上之環氧基之2價有機基。 The structural unit (B) can be introduced into a copolymer by polymerizing an epoxy compound (b) represented by the following formula (b1) and an unsaturated carboxylic acid or its anhydride (a). ◎[Chemical formula 5]

In formula (b1), R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R ^b2 represents a divalent hydrocarbon group which may contain a heteroatom. R ^b3 represents a divalent organic group having two or more epoxy groups.

As an alkyl group having 1 to 7 carbon atoms in R ^b1 , for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, pentyl, hexyl, heptyl base. From the viewpoint of copolymerizability and reactivity, R ^b1 is preferably a hydrogen atom, a methyl group or an ethyl group.

In the divalent hydrocarbon group of R ^b2 which may contain a heteroatom, the heteroatom may be bonded to the terminal of the hydrocarbon group or interposed between the carbon atoms constituting the hydrocarbon group. The hetero atom is not particularly limited, and examples thereof include a nitrogen atom, an oxygen atom, and a sulfur atom. R ^b2 may have a substituent.

As a divalent hydrocarbon group that may contain a heteroatom in R ^b2 , for example, straight chains such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, trimethylene, etc. Or a branched chain alkylene group (preferably an alkylene group with 1 to 12 carbons, more preferably an alkylene group with 1 to 6 carbons, especially an alkylene group with 1 to 3 carbons); 1, 2-cyclopentyl, 1,3-cyclopentyl, cyclopentylene, 1,2-cyclohexyl, 1,3-cyclohexyl, 1,4-cyclohexyl, cyclohexylene, etc. Cycloalkyl (preferably cycloalkylene with 3 to 12 carbons, more preferably cycloalkylene with 4 to 10 carbons, especially cycloalkylene with 5 to 8 carbons); oxymethylene oxyalkylene group, oxyethylene group, oxypropylidene group and other oxyalkylene groups (preferably an oxyalkylene group with 1 to 12 carbons, more preferably an oxyalkylene group with 1 to 6 carbons); sulfomethylene , thioethylene, thiopropyl and other thioalkylene groups (preferably a thioalkylene group with 1 to 12 carbon atoms, more preferably a thioalkylene group with a carbon number of 1 to 6); aminomethylene , aminoethylene, aminopropylidene and other aminoalkylene groups (preferably an aminoalkylene group with 1 to 12 carbons, more preferably an aminoalkylene group with 1 to 6 carbons); and 2 of these A 2-valent group formed by more than one bond. Among them, from the viewpoint of storage stability, a straight-chain alkylene group having 1 to 3 carbon atoms is preferable, and an ethylylene group is more preferable.

R ^b3 is a divalent organic group having two or more epoxy groups. That is, it is a divalent organic group, and it is a group which has at least 2 epoxy groups. The aforementioned epoxy group is preferably an epoxy group other than an alicyclic epoxy group. The reason is that the general epoxy group (epoxy group other than alicyclic epoxy group) has excellent reactivity compared with alicyclic epoxy group, so the copolymer of the present invention exhibits a Good hardening. In addition, in the epoxy compound (b) represented by formula (b1), when the structure around the epoxy group is crowded, the reactivity of the epoxy group decreases, so by using an epoxy group other than an alicyclic epoxy group To improve hardening, so as to achieve good solvent resistance and hardening. The alicyclic epoxy group refers to a group composed of two adjacent carbon atoms and an oxygen atom constituting an alicyclic ring, such as an epoxycyclohexyl group. The aforementioned at least two epoxy groups may be the same or different. R ^b3 may have a substituent.

By making the divalent organic group in R ^b3 have two or more epoxy groups, the amount of epoxy groups per molecule of the acrylic monomer will increase, so the hardened product of the copolymer containing the aforementioned monomers as structural units The crosslink density becomes higher. Therefore, it is considered that the formed cured film has a fine structure to improve solvent resistance. In addition, the number of epoxy groups contained in the epoxy compound (b) represented by formula (b1), that is, the number of epoxy groups contained in the divalent organic group in R ^b3 , is, for example, preferably 2 to 10, more preferably Preferably, it is 2-6, More preferably, it is 2-4. Being within the above range tends to exhibit good solvent resistance and curability.

Examples of the organic group in R ^b3 include a hydrocarbon group, a heterocyclic group, and a group in which two or more of these are bonded via a single bond or a linking group.

As the aforementioned hydrocarbon group, for example, straight or branched chain alkylene groups such as methylene, methylmethylene, dimethylmethylene, ethylidene, propylene, trimethylene, etc. 1 to 12 alkylene); 1,2-cyclopentyl, 1,2-cyclohexyl and other monocyclic or polycyclic cycloalkylenes (for example, cycloalkylenes with 3 to 12 carbons) ; Extended aryl such as phenylene. As the aforementioned heterocyclic group, for example, 5 to 10-membered heterocycloalkylene and heteroarylene containing at least one heteroatom selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom can be exemplified. (For example, a group obtained by removing two hydrogen atoms from the structural formula of a heterocycle containing an oxygen atom such as a furan ring; a heterocycle containing a nitrogen atom such as a pyrrole ring and a pyridine ring; a heterocycle containing a sulfur atom such as a thiophene ring) . Examples of the linking group include heteroatoms such as nitrogen atoms, oxygen atoms, and sulfur atoms (e.g., ether bonds (-O-), thioether bonds (-S-), etc.), carbonyl groups (-CO-), esters, etc. bond (-COO-), amide bond (-CONH-), carbonate bond (-OCOO-), etc.

That is, R ^b3 represents a divalent group in which at least two hydrogen atoms in these organic groups are substituted with epoxy groups.

R ^b3 is preferably a group having two or more epoxy groups and two or more hydrocarbon groups bonded via a linking group (especially an ether bond) containing an oxygen atom. At this time, two or more hydrocarbon groups other than epoxy groups are preferably linear or branched chain alkylene groups (especially alkylene groups with 1 to 4 carbon atoms in the main chain), and may have an alkyl group Monocyclic or polycyclic cycloalkylene groups such as substituents (especially cycloalkylene groups with 5 to 8 carbon atoms), more preferably ethylene groups, cyclohexenyl groups, and norbornenyl groups that may have substituents . The above two or more hydrocarbon groups may be the same or different. In addition, the carbon number of the main chain in the alkylene group refers to the number of the shortest carbon chain in the alkylene group formed from the carbon atom bonded to R ^b2 -O- to the carbon atom bonded to OH.

As said epoxy compound (b), the compound represented by following formula (b2) is mentioned, for example. ◎[Chemical Formula 6]

In formula (b2), R ^b1 is the same as described as R ^b1 in formula (b1), and represents a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R ^b2 is the same as that described as R ^b2 in the formula (b1), and represents a divalent hydrocarbon group which may contain a heteroatom. R ^b4 identically or differently represent a divalent hydrocarbon group which has an epoxy group and may contain a heteroatom. nb1 represents an integer of 2 or more.

The divalent hydrocarbon group having an epoxy group and optionally containing a heteroatom in R ^b4 refers to a divalent hydrocarbon group optionally containing a heteroatom in which at least one hydrogen atom is substituted with an epoxy group. The above-mentioned epoxy group is preferably an epoxy group other than an alicyclic epoxy group. R ^b4 may have a substituent.

As the divalent hydrocarbon group that may contain a heteroatom in R ^b4 , for example, it can be exemplified by linear or branched alkylene groups such as methylene, methylmethylene, dimethylmethylene, and ethylidene ( It is preferably an alkylene group with 1 to 8 carbons, more preferably an alkylene group with 2 to 4 carbons); 1,2-cyclopentyl and other monocyclic or polycyclic cycloalkylene groups (preferably A cycloalkylene group with 3 to 12 carbons, more preferably a cycloalkylene group with 4 to 10 carbons, especially a cycloalkylene group with 5 to 8 carbons); oxymethylene, oxyethylene, Oxyalkylene groups such as oxypropylidene; thioalkylene groups such as thiomethylene, thioethylidene, and thiopropylidene; aminomethylene, aminoethylidene, and aminopropylidene and other aminoalkylene groups ; and a divalent group formed by two or more of these bonds. That is, R ^b4 represents a group in which at least one hydrogen atom of these divalent hydrocarbon groups which may contain heteroatoms is substituted with an epoxy group.

As divalent hydrocarbon groups that may contain heteroatoms other than epoxy groups in R ^b4 , linear or branched chain alkylene groups (especially alkylene groups with 1 to 4 carbon atoms in the main chain) are preferred. ), a monocyclic or polycyclic cycloalkylene group (especially a cycloalkylene group with 5 to 8 carbon atoms) that may have a substituent such as an alkyl group, more preferably an ethylene group that may have a substituent, cyclohexene base, nor camphenyl. In addition, R ^b4 in two or more parentheses added with nb1 may be the same or different.

From the viewpoint of storage stability, the epoxy compound (b1) is preferably a compound represented by the following formula (b3) or a compound represented by the following formula (b4). Moreover, the said epoxy compound (b1) can be used individually or in combination of 2 or more types.

◎[Chemical Formula 7]

In formula (b3), R ^b1 is the same as described as R ^b1 in formula (b1), and represents a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R ^b2 is the same as that described as R ^b2 in the formula (b1), and represents a divalent hydrocarbon group which may contain a heteroatom. R ^b5 identically or differently represent a hydrogen atom or an alkyl group having 1 to 6 carbons. R ^b6 identically or differently represent a single bond or a divalent hydrocarbon group which may contain a heteroatom. nb2 and nb3 each represent an integer of 0 or more, and the sum of nb2 and nb3 is 2 or more. The oxirane ring may have an alkyl group having 1 to 6 carbons.

The two groups in [ ] in the formula do not necessarily have to be arranged in the order shown in formula (b3). That is, the compound represented by the formula (b3) represents that there are nb2 and nb3 of the two groups (structural units) in [] in the formula respectively, and the arrangement of the aforementioned groups can be in the order shown in the formula (b3), or Instead, they may be alternately arranged, or may be arranged consecutively by a certain number. More specifically, the group represented by -C(R ^b5 ) ₂ -C(R ^b5 )(R ^b6 -C ₂ H ₃ O)- as the two groups in [] (hereinafter referred to as "L group") ) and -C(R ^b5 )(R ^b6 -C ₂ H ₃ O)-C(R ^b5 ) ₂ - (hereinafter referred to as "R group") can be -L as in the above formula (b3) _nb2 -R _nb3 - may also be -R _nb3 -L _nb2 -.

In addition, when nb2 and nb3 are each 2 or more, they may be arranged alternately like -LRRL _... , or may be arranged consecutively by a certain number.

◎[Chemical Formula 8]

In formula (b4), R ^b1 is the same as that described as R ^b1 in formula (b1), and represents a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R ^b2 is the same as that described as R ^b2 in the formula (b1), and represents a divalent hydrocarbon group which may contain a heteroatom. R ^b7 identically or differently represent a hydrogen atom or an alkyl group having 1 to 6 carbons. R ^b8 is a group bonded to the ring Z, and represents a single bond or a divalent hydrocarbon group which may contain a heteroatom, identically or differently. m represents an integer of 1 to 3; Ring Z represents an alicyclic hydrocarbon ring having 3 to 20 carbon atoms. nb4 represents an integer of 2 or more. The oxirane ring may have an alkyl group having 1 to 6 carbons. Ring Z may have an alkyl group having 1 to 6 carbon atoms as a group other than ^Rb7 and ^Rb8 .

The alkyl group having 1 to 6 carbon atoms in R ^b5 and R ^b7 is not particularly limited, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl base, pentyl, hexyl, etc.

The divalent hydrocarbon groups that may contain heteroatoms in R ^b6 and R ^b8 can be, for example, methylene, methyl methylene, dimethyl methylene, ethylene, propylene, trimethylene, Butyl, pentyl, hexyl and other linear or branched alkylene groups (preferably alkylene groups with 1 to 18 carbons, more preferably alkylene groups with 2 to 12 carbons, especially carbon 3 to 8 alkylene); 1,2-cyclopentyl, 1,3-cyclopentyl, cyclopentylene, 1,2-cyclohexyl, 1,3-cyclohexyl, 1 , 4-cyclohexylene, cyclohexylene and other cycloalkylene groups (preferably a cycloalkylene group with 3 to 12 carbons, more preferably a cycloalkylene group with 4 to 10 carbons, especially preferably a cycloalkylene group with 5 carbons to 8 cycloalkylene groups); oxymethylene, oxyethylidene, oxypropylidene and other oxyalkylene groups (preferably oxyalkylene groups with 1 to 12 carbons, more preferably 1 to 12 carbons) 6’s oxyalkylene group); thiomethylene, thioethylene, thiopropyl and other thioalkylene groups (preferably thioalkylene with 1 to 12 carbons, more preferably 1 to 6 carbons) thioalkylene); aminomethylene, aminoethylidene, aminopropylidene and other aminoalkylene groups (preferably aminoalkylene groups with 1 to 12 carbons, more preferably 1 to 6 carbons) amino alkylene group); and a divalent group formed by bonding two or more of these.

From the viewpoint of storage stability, R ^b6 is preferably a straight chain or branched chain alkylene group having 1 to 18 carbons, more preferably a straight chain or branched chain alkylene group having 3 to 8 carbons. In addition, R ^b8 is preferably a single bond from the viewpoint of storage stability.

As the alicyclic hydrocarbon ring having 3 to 20 carbon atoms in the aforementioned ring Z, for example, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cyclooctane ring, etc. 3 to 20 member (preferably 3 to 15 members, especially preferably 5 to 12 members) cycloalkane ring; cyclopropene ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, etc. 3 to 20 members (preferably 3 to 15 members, preferably 5 to 10 members) cycloalkene ring and other monocyclic alicyclic hydrocarbon ring; adamantane ring; norbornane ring, norbornane ring, camphane ring, isobornane ring, Tricyclo[5.2.1.0 ^2,6 ]decane rings, tetracyclo[4.4.0.1 ^2,5 .1 ^7,10 ]dodecane rings and other rings containing norbornane or norbornene rings; perhydroindene Polycyclic aromatic condensed rings such as perhydronaphthalene ring, decahydronaphthalene ring (perhydronaphthalene ring), perhydrogenene ring (tricyclo[7.4.0.0 ^3,8 ]tridecane ring), perhydroanthracene ring, etc. are hydrogenated (preferably a fully hydrogenated ring); tricyclic [4.2.2.1 ^2,5 ] undecane ring and other cross-linked hydrocarbon rings of 2-ring, 3-ring, 4-ring systems (for example, carbon number 6 to 20 cross-linked hydrocarbon ring) and other cross-linked cyclic hydrocarbon rings with 2 to 6 rings. Among them, a cycloalkane ring or a norbornane ring with 5 to 12 members is preferable from the viewpoint of storage stability.

nb2 and nb3 are integers of 0 or more. As long as the sum of nb2 and nb3 is 2 or more, it is not particularly limited, for example, preferably 2 to 20, more preferably 2 to 12, further preferably 2 to 8, especially preferably 2 to 4, most preferably 3 .

As long as nb4 is an integer of 2 or more, it is not particularly limited. For example, it is preferably 2-20, more preferably 2-12, further preferably 2-8, particularly preferably 2-4, most preferably 3. It will not specifically limit as long as m is an integer of 1-3, For example, 1 is preferable.

In the compound represented by the formula (b3) and the compound represented by the formula (b4), the alkyl group having 1 to 6 carbons that the oxirane ring may have is not particularly limited, for example, it may be an alkyl group having 1 to 6 carbons alkyl. Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, pentyl, hexyl and the like.

Examples of alkyl groups having 1 to 6 carbon atoms that ring Z may have include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, pentyl, hexyl, etc. .

In the compound represented by the formula (b3) and the compound represented by the formula (b4), it is preferable that a hydrocarbon chain having a certain number of carbon atoms exists between the main chain of the polyethylene oxide group and the epoxy group. That is, in the compound represented by the formula (b3), when R ^b6 is a linear or branched chain alkylene group having 1 to 18 carbons (more preferably 3 to 8 carbons), the storage stability becomes good. In addition, among the compounds represented by the formula (b4), the storage stability becomes good because the ring Z has a cycloalkane ring or a norbornane ring having 5 to 12 members. The reason for this is considered to be that when the hydrocarbon chain between the main chain of the polyethylene oxide group and the epoxy group is the above, the structure around the epoxy group is crowded, thereby reducing the reactivity and improving the storage stability. On the other hand, the aforementioned compounds are characterized in that they harden even at relatively low temperatures in the hardening stage.

◎[化學式10]

Specific examples of the compound represented by the formula (b3) include compounds represented by the following formula (b3-1) and compounds represented by the formula (b3-2). ◎[Chemical Formula 9]

◎[Chemical Formula 10]

◎[化學式12]

◎[化學式13]

Specific examples of the compound represented by the formula (b4) include compounds represented by the following formula (b4-1), compounds represented by the formula (b4-2), and compounds represented by the formula (b4-3). compound. ◎[Chemical Formula 11]

◎[Chemical Formula 12]

◎[Chemical Formula 13]

The ratio (content) of the structural unit (B) in the copolymer is not particularly limited, and is preferably 10 to 98% by weight, more preferably 50 to 95% by weight, and even more preferably 70% by weight relative to all structural units. to 92% by weight, preferably 80 to 90% by weight. When the ratio of the structural unit (B) is more than the above-mentioned lower limit value, the amount of epoxy group contained in the copolymer becomes suitable for hardening, so it is hardened even at a relatively low temperature, and the crosslinking of the hardened product Since the structure becomes dense, it tends to be excellent in solvent resistance. When the ratio of a structural unit (B) is below the said upper limit, since the hydroxyl group contained in a copolymer becomes a suitable quantity, it exists in the tendency which is excellent in the solvent resistance with respect to the highly polar solvent especially. In addition, since the copolymer becomes hydrophilic, it tends to be excellent in developability (fast developing speed, less residue). [Structural unit (C)]

The structural unit (C) is derived from styrene (c1), N-substituted maleimide (c2), N-vinyl compound (c3), and the aforementioned formula (2) which may be substituted by an alkyl group. A structural unit of at least one compound in the group consisting of unsaturated carboxylic acid derivatives (c4) represented by ). The structural unit (C) has the function of imparting hardness to the cured product (cured film), the function of smoothing the copolymerization reaction, the function of improving the solubility to the solvent, the function of improving the adhesion to the base material, and the like.

The structural unit (C) is formed by making at least one compound selected from the group consisting of the aforementioned (c1) to (c4) and an unsaturated carboxylic acid or its anhydride (a) and the epoxy compound represented by the aforementioned formula (b1) The compounds are polymerized together and can be introduced into the copolymer. (styrene (c1))

The alkyl group in the styrene (c1) which may be substituted by an alkyl group is not particularly limited, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, C1-7 alkyl such as hexyl. Among these, an alkyl group having 1 to 4 carbon atoms such as a methyl group or an ethyl group is preferred, and a methyl group is more preferred. The aforementioned alkyl group may be bonded to either the vinyl group of styrene or the benzene ring.

Representative examples of styrene (c1) which may be substituted with an alkyl group include styrene, α-methylstyrene, vinyltoluene (o-vinyltoluene, m-vinyltoluene, p-vinyltoluene), etc. . Among them, styrene is preferred. The styrene (c1) which may be substituted with an alkyl group can be used individually or in combination of 2 or more types. (N-substituted maleimide (c2))

As N-substituted maleimide (c2), the compound represented by following formula (3) is mentioned, for example. ◎[Chemical Formula 14]

In formula (3), R ²¹ represents a monovalent organic group.

As said monovalent organic group, a hydrocarbon group and a heterocyclic group are mentioned, for example. Examples of hydrocarbon groups include: methyl, ethyl, propyl, isopropyl, butyl, hexyl and other alkyl groups (for example, alkyl groups having 1 to 6 carbon atoms); cyclopentyl, cyclohexyl, cyclooctyl cycloalkyl groups such as adamantyl, norbornyl; aryl groups such as phenyl; aralkyl groups such as benzyl; groups formed by bonding two or more of these, etc. Examples of the heterocyclic group include 5 to 10-membered heterocycloalkyl and heteroaryl groups containing at least one heteroatom selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms.

There are no particular limitations on the N-substituted maleimide (c2), for example, N-methylmaleimide, N-ethylmaleimide, N - N-alkylmaleimide such as propylmaleimide; N-cyclopentylmaleimide, N-cyclohexylmaleimide, N- Cyclooctylmaleimide, N-adamantylmaleimide, N-norcamylmaleimide, etc. N-cycloalkylmaleimide; N- N-arylmaleimides such as phenylmaleimide; N-aralkylmaleimides such as N-benzylmaleimide; and the like. Among them, N-cyclohexylmaleimide is preferred. N-substituted maleimide (c2) can be used individually or in combination of 2 or more types. (N-vinyl compound (c3))

The N-vinyl compound (c3) is not particularly limited, and examples thereof include N-vinylformamide, N-vinylacetamide, N-vinylisoacrylamide, N-vinyl- N-methylacetamide, N-vinylpyrrolidone, N-vinylcarbazole, N-vinylpiperidone, N-vinylcaprolactam, and the like. The N-vinyl compound (c3) can be used alone or in combination of two or more. (unsaturated carboxylic acid derivatives (c4))

The unsaturated carboxylic acid derivative (c4) can be represented by following formula (2). ◎[Chemical Formula 15]

In formula (2), R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R ¹² represents a monovalent hydrocarbon group which may contain a heteroatom. X represents a heteroatom.

Examples of the alkyl group having 1 to 7 carbon atoms in R ¹¹ include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, hexyl and the like. R ¹¹ is particularly preferably a hydrogen atom or a methyl group.

As the monovalent hydrocarbon group that may contain a heteroatom in R ¹² , for example, an alkyl group, a heteroalkyl group, an alkenyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a combination of two or more of these can be exemplified. The foundation of success. In addition, the carbon atom in ^R12 is bonded to X.

As the aforementioned alkyl group, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, hexyl, octyl, decyl, dodecyl, isodecyl C1-23 alkyl groups such as lauryl, stearyl, etc.

As the aforementioned heteroalkyl group, for example, it can be exemplified by: -(R ¹³ -O)pR ¹⁴ group (in the formula, R ¹³ represents an alkylene group with 1 to 12 carbons. ^{R 14} represents a hydrogen atom or an alkylene group with 1 to 12 carbons Alkyl group. p represents an integer of 1 or more), -R ¹⁵ -NR ¹⁶ R ¹⁷ group (in the formula, R ¹⁵ represents an alkylene group with 1 to 12 carbon atoms. ^{R 16} and R ¹⁷ represent a hydrogen atom respectively identically or differently or an alkyl group with 1 to 4 carbon atoms).

Examples of the alkenyl group include alkenyl groups having 2 to 23 carbon atoms such as allyl, 3-butenyl, and 5-hexenyl.

Examples of the cycloalkyl group include cyclopentyl groups, cyclohexyl groups, cyclooctyl groups, adamantyl groups, and norbornyl groups having 3 to 12 carbon atoms.

As the aforementioned heterocycloalkyl group, for example, a group including a cyclic ether structure such as an oxetane ring, an oxolane ring, a α-alkane ring, and an oxepane ring (for example, a group containing three or more membered rings) The base of the cyclic ether) and so on.

Examples of the aryl group include aryl groups having 6 to 12 carbon atoms such as phenyl and naphthyl.

Examples of hetero atoms in X include nitrogen atoms, oxygen atoms, and sulfur atoms.

The unsaturated carboxylic acid derivative (c4) represented by the formula (2) is not particularly limited, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propylene (meth)acrylate ester, isopropyl (meth)acrylate, butyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, etc. Meth)acrylates; N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-di (Meth)acrylates with alkylamine groups such as isopropylaminoethyl, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-(meth)acrylate Hydroxybutyl, 4-hydroxybutyl (meth)acrylate and other hydroxyl-containing (meth)acrylates, methoxydiethylene glycol (meth)acrylate, ethoxydiethylene glycol (methyl) Acrylate, Isooctyloxydiethylene glycol (meth)acrylate, Phenoxytriethylene glycol (meth)acrylate, Methoxytriethylene glycol (meth)acrylate, Methoxy poly (meth)acrylates with heteroalkyl groups such as polyalkylene glycol (meth)acrylates, etc.; (meth)acrylates with alkenyl groups such as allyl (meth)acrylate Acrylates; cyclohexyl (meth)acrylate, 1-adamantyl (meth)acrylate, isobornyl (meth)acrylate, tricyclo[5,2,1,0 ^2,6 ]dec-8 -Alcohol (meth)acrylate and other (meth)acrylates with monocyclic or polycyclic cycloalkyl groups; glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, ( 2-Ethylglycidyl methacrylate, 2-glycidyloxyethyl (meth)acrylate, 3-glycidyloxypropyl (meth)acrylate, glycidyloxybenzene (meth)acrylate Ester, etc. (meth)acrylate with epoxy group (oxirane group), oxetanyl (meth)acrylate, 3-methyl-3-oxetane (meth)acrylate Alkyl esters, 3-ethyl-3-oxetanyl (meth)acrylate, (3-methyl-3-oxetanyl)methyl (meth)acrylate, (methyl )(3-ethyl-3-oxetanyl)methyl acrylate, 2-(3-methyl-3-oxetanyl)ethyl (meth)acrylate, (meth)acrylic acid 2-(3-Ethyl-3-oxetanyl)ethyl ester, 2-[(3-methyl-3-oxetanyl)methoxy]ethyl (meth)acrylate, 2-[(3-Ethyl-3-oxetanyl)methoxy]ethyl (meth)acrylate, 3-[(3-methyl-3-oxetane)(meth)acrylate Alkyl)methoxy]propyl, 3-[(3-ethyl-3-oxetanyl)methoxy]propyl (meth)acrylate, etc. base) acrylate, tetrahydrofurylmethyl (meth)acrylate and other (meth)acrylates with oxolyl groups, 3,4-epoxycyclohexyl (meth)acrylate, (meth)acrylic acid 3 , 4-epoxycyclohexyl methyl ester, 2-(3,4-epoxycyclohexyl)ethyl (meth)acrylate, 2-(3,4-epoxycyclohexylmethyl)acrylate Oxy)ethyl ester, 3-(3,4-epoxycyclohexylmethoxy)propyl (meth)acrylate, etc. (meth)acrylates containing alicyclic epoxy groups, etc., have heterocycloalkyl groups (meth)acrylates (such as cyclic ether groups containing more than 3-membered rings); (meth)acrylates with aryl groups such as phenyl (meth)acrylate and benzyl (meth)acrylate; 3 -(Meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyl Diethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 8-(meth)acryloxyoctyltrimethoxysilane, etc. base) acrylate. The unsaturated carboxylic acid derivative (c4) represented by formula (2) can be used individually or in combination of 2 or more types. Among them, methyl (meth)acrylate is preferred.

The ratio (content) of the structural unit (C) in the copolymer is not particularly limited, and is preferably 0 to 80% by weight, more preferably 1 to 60% by weight, and even more preferably 5% by weight relative to all structural units. to 40% by weight, preferably 10 to 30% by weight, most preferably 15 to 25% by weight. When the ratio of the structural unit (C) is 1% by weight or more (especially 5% by weight or more), the function of imparting hardness to the cured product (hardened film) and the function of smoothing the copolymerization reaction can be effectively exhibited, and the effect on the The function of the solubility of the solvent, the function of improving the adhesion to the base material, etc. Since the ratio of the structural units (A) and (B) will increase relatively when the ratio of a structural unit (C) is below the said upper limit, the function of a structural unit (A) and (B) will be exhibited effectively. [Structural unit (D)]

The copolymer of the present invention may contain structural units (D) other than the aforementioned structural units (A) to (C). As a structural unit (D), the structural unit derived from (meth)acrylamide, (meth)acrylonitrile is mentioned, for example.

When the copolymer of the present invention comprises structural unit (A) and structural unit (B), and does not comprise structural unit (C), the total amount of structural unit (A) and structural unit (B) is relative to all structural units, relatively It is preferably at least 90% by weight, more preferably at least 95% by weight, further preferably at least 99% by weight, and may be substantially 100% by weight. In addition, when the copolymer of the present invention comprises a structural unit (A), a structural unit (B) and a structural unit (C), the total amount of structural units (A) to (C) is preferably 90% relative to all structural units. % by weight or more, more preferably 95% by weight or more, further preferably 99% by weight or more, and may be substantially 100% by weight.

The weight average molecular weight (Mw) of the copolymer is not particularly limited, for example, it is preferably 6,000 to 60,000, more preferably 7,000 to 30,000, further preferably 8,000 to 20,000, and especially preferably 8,500 to 15,000. The molecular weight distribution of the copolymer (ratio of weight average molecular weight to number average molecular weight: Mw/Mn) is not particularly limited, for example, it is preferably 6.0 or less (such as 1.5 to 6.0), more preferably 2.0 to 5.0, and even more preferably 3.0 to 4.0. The weight-average molecular weight (Mw) and the number-average molecular weight (Mn) can be measured by, for example, GPC using polystyrene as a standard substance, and are preferably measured by the method used in the examples.

The copolymer of this invention functions as a binder resin of the photosensitive resin composition of this invention. ＜Production method of copolymer＞

The copolymer among the present invention can be by unsaturated carboxylic acid or its acid anhydride (a), the epoxy compound (b) shown in aforementioned formula (b1), and optionally selected from aforementioned (c1) to (c4) It is produced by copolymerizing at least one compound in the formed group with a compound corresponding to the aforementioned structural unit (D). Hereinafter, compounds that can be introduced into copolymers, such as unsaturated carboxylic acids or their anhydrides (a), may be collectively referred to as "monomers".

In the method for producing the copolymer of the present invention, copolymerization may be performed in the presence of a polymerization initiator. As the aforementioned polymerization initiator, a customary or well-known free radical polymerization initiator can be used, for example, 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4- Dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylpropanoic acid) di Azo compounds such as methyl ester, 2,2'-azobis(2-methylpropionate) diethyl ester, 2,2'-azobis(2-methylpropionate) dibutyl ester, benzene peroxide Organic peroxides such as formyl, lauryl peroxide, tertiary butyl peroxypivalate, 1,1-bis(tertiary butylperoxy)cyclohexane, hydrogen peroxide, etc. When using a peroxide as a radical polymerization initiator, a reducing agent may be combined as a redox type initiator. Among them, azo compounds are preferred, and 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis Nitrobis(2-methylpropionate) dimethyl ester.

The amount of the polymerization initiator used is not particularly limited as long as it is within the range that does not hinder the smooth copolymerization reaction. For example, it is preferably 1 to 20 parts by weight relative to the total amount of monomers (100 parts by weight), more preferably 5 to 15 parts by weight.

The copolymerization reaction of the present invention can be carried out by conventional methods used for producing acrylic polymers or styrene polymers, such as solution polymerization, block polymerization, suspension polymerization, block-suspension polymerization, and emulsion polymerization. The monomer and the polymerization initiator may be supplied to the reaction system at a time, respectively, or part or all of them may be dropped into the reaction system. For example, a method of polymerizing by dropping a solution of a polymerization initiator dissolved in a polymerization solvent in a monomer or a mixture of a monomer and a polymerization solvent kept at a certain temperature; A method in which a solution of an initiator dissolved in a polymerization solvent is dripped into a polymerization solvent kept at a constant temperature to polymerize (dropping polymerization method), etc.

The copolymer of the present invention is preferably obtained by performing a copolymerization reaction in a polymerization solvent. The polymerization solvent can be appropriately selected according to the monomer composition, for example, ether (diethyl ether; ethylene glycol mono or dialkyl ether, diethylene glycol mono or dialkyl ether, propylene glycol mono or dialkyl ether , propylene glycol mono or diaryl ether, dipropylene glycol mono or dialkyl ether, tripropylene glycol mono or dialkyl ether, 1,3-propylene glycol mono or dialkyl ether, 1,3-butanediol mono or dialkyl ether chain ethers such as base ethers, 1,4-butanediol mono- or di-alkyl ethers, glycerol mono-, di-, or tri-alkyl ethers and other glycol ethers; tetrahydrofuran, di-ane and other cyclic ethers, etc.), esters ( Methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, C _5-6 cycloalkanediol mono or diacetate, C _5-6 cycloalkane dimethanol mono or diacetate and other carboxylic acid esters; ethylene glycol monoalkyl ether acetate, ethylene glycol mono or diacetate, diethylene dimethanol Alcohol monoalkyl ether acetate, diethylene glycol mono or diacetate, propylene glycol monoalkyl ether acetate, propylene glycol mono or diacetate, dipropylene glycol monoalkyl ether acetate, dipropylene glycol mono or diacetate, 1,3-propanediol monoalkyl ether acetate, 1,3-propanediol mono or diacetate, 1,3-butanediol monoalkyl ether acetate, 1,3- Butanediol mono or diacetate, 1,4-butanediol monoalkyl ether acetate, 1,4-butanediol mono or diacetate, glycerol mono, di or triacetate, glycerin Mono- or di-C _1-4 alkyl ether di- or mono-acetate, tripropylene glycol mono-alkyl ether acetate, tripropylene glycol mono- or di-acetate and other glycol acetates or glycol ether acetates, etc.) , ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 3,5,5-trimethyl-2-cyclohexen-1-one, etc.), amides (N,N -Dimethylacetamide, N,N-dimethylformamide, etc.), oxonide (dimethylsulfide, etc.), alcohol (methanol, ethanol, propanol, C _5-6 cycloalkanediol, C _5-6 naphthenic dimethanol, etc.), hydrocarbons (aromatic hydrocarbons such as benzene, toluene, xylene, etc., aliphatic hydrocarbons such as hexane, alicyclic hydrocarbons such as cyclohexane, etc.), mixed solvents of these, etc.

The reaction temperature in the polymerization reaction can be appropriately selected according to the type and composition of the monomer, and is not particularly limited. For example, it is preferably 30 to 150°C.

烷等環狀醚）、酮（丙酮、甲基乙基酮、二異丁基酮等）、酯（乙酸乙酯、乙酸丁酯等）、碳酸酯（碳酸二甲酯、碳酸二乙酯、碳酸乙二酯、碳酸丙二酯等）、醇（甲醇、乙醇、丙醇、異丙醇、丁醇等）、羧酸（乙酸等）、及包含該等溶劑之混合溶劑等。 ＜有色材料＞ The reaction solution containing the copolymer obtained by the above method may be purified by performing precipitation or reprecipitation as necessary. The solvent used for precipitation or reprecipitation may be either an organic solvent or water, and may be a mixed solvent of these. Examples of organic solvents include: hydrocarbons (aliphatic hydrocarbons such as pentane, hexane, heptane, and octane; alicyclic hydrocarbons such as cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene); aliphatic hydrocarbons), halogenated hydrocarbons (dichloromethane, chloroform, carbon tetrachloride and other halogenated aliphatic hydrocarbons; chlorobenzene, dichlorobenzene and other halogenated aromatic hydrocarbons, etc.), nitro compounds (nitromethane, nitroethane, etc. ), nitriles (acetonitrile, benzonitrile, etc.), ethers (diethyl ether, diisopropyl ether, dimethoxyethane and other chain ethers; tetrahydrofuran, di

Alkanes and other cyclic ethers), ketones (acetone, methyl ethyl ketone, diisobutyl ketone, etc.), esters (ethyl acetate, butyl acetate, etc.), carbonates (dimethyl carbonate, diethyl carbonate, Ethylene carbonate, propylene carbonate, etc.), alcohols (methanol, ethanol, propanol, isopropanol, butanol, etc.), carboxylic acids (acetic acid, etc.), and mixed solvents containing these solvents, etc. ＜Colored materials＞

In the present invention, the photosensitive resin composition may contain a colored material. As a colored material (colorant), it is only necessary to have coloring properties, and the color and material can be appropriately selected according to applications such as color filters. Specifically, any of pigments, dyes, and natural pigments can be used as the colored material, but pigments and/or dyes are preferred for color filter applications requiring high color purity, brightness, and contrast.

The aforementioned pigments may be any of organic pigments and inorganic pigments, and examples of organic pigments include compounds classified as pigments in the Dye Index (C.I.; issued by The Society of Dyers and Colourists, Inc.). Concretely, one with a dye index (C.I.) name as described below can be exemplified.

C.I. Pigment Yellow 1, C.I. Pigment Yellow 3, C.I. Pigment Yellow 12, C.I. Pigment Yellow 13, C.I. Pigment Yellow 14, C.I. Pigment Yellow 16, C.I. Pigment Yellow 17, C.I. Pigment Yellow 20, C.I. C.I. Pigment Yellow 55, C.I. Pigment Yellow 83, C.I. Pigment Yellow 86, C.I. Pigment Yellow 93, C.I. Pigment Yellow 94, C.I. Pigment Yellow 109, C.I. Pigment Yellow 110, C.I. Pigment Yellow 117, C.I. C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 147, C.I. Pigment Yellow 148, C.I. Pigment Yellow 150, C.I. Pigment Yellow 153, C.I. Pigment Yellow 154, C.I. Pigment Yellow 155, C.I. C.I. Pigment Yellow 180, C.I. Pigment Yellow 194, C.I. Pigment Yellow 211, C.I. Pigment Yellow 214 and other yellow pigments.

C.I. Pigment Orange 5, C.I. Pigment Orange 13, C.I. Pigment Orange 14, C.I. Pigment Orange 24, C.I. Pigment Orange 31, C.I. Pigment Orange 34, C.I. Pigment Orange 36, C.I. Pigment Orange 38, C.I. Pigment Orange 40, C.I. C.I. Pigment Orange 43, C.I. Pigment Orange 46, C.I. Pigment Orange 49, C.I. Pigment Orange 51, C.I. Pigment Orange 55, C.I. Pigment Orange 59, C.I. Pigment Orange 61, C.I. Pigment Orange 64, C.I. Pigment Orange 65, C.I. C.I. Pigment Orange 70, C.I. Pigment Orange 71, C.I. Pigment Orange 72, C.I. Pigment Orange 73, C.I. Pigment Orange 74 and other orange pigments.

C.I. Pigment Red 1, C.I. Pigment Red 2, C.I. Pigment Red 5, C.I. Pigment Red 9, C.I. Pigment Red 17, C.I. Pigment Red 31, C.I. Pigment Red 32, C.I. Pigment Red 41, C.I. Pigment Red 97, C.I. Pigment Red 105, C.I. Pigment Red 122, C.I. Pigment Red 123, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 168, C.I. Pigment Red 170, C.I. Pigment Red 171, C.I. Pigment Red 175, C.I. C.I. Pigment Red 177, C.I. Pigment Red 178, C.I. Pigment Red 179, C.I. Pigment Red 180, C.I. Pigment Red 185, C.I. Pigment Red 187, C.I. Pigment Red 192, C.I. Pigment Red 202, C.I. Pigment Red 206, C.I. C.I. Pigment Red 209, C.I. Pigment Red 214, C.I. Pigment Red 215, C.I. Pigment Red 216, C.I. Pigment Red 220, C.I. Pigment Red 221, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red 243, C.I. C.I. Pigment Red 255, C.I. Pigment Red 262, C.I. Pigment Red 264, C.I. Pigment Red 265, C.I. Pigment Red 272 and other red pigments.

C.I. Pigment Violet 1, C.I. Pigment Violet 19, C.I. Pigment Violet 23, C.I. Pigment Violet 29, C.I. Pigment Violet 32, C.I. Pigment Violet 36, C.I. Pigment Violet 38 and other purple pigments.

C.I. Pigment Blue 15, C.I. Pigment Blue 15:3, C.I. Pigment Blue 15:4, C.I. Pigment Blue 15:6, C.I. Pigment Blue 60, C.I. Pigment Blue 80 and other blue pigments.

C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58 and other green pigments.

C.I. Pigment Brown 23, C.I. Pigment Brown 25 and other brown pigments.

C.I. Pigment Black 1, C.I. Pigment Black 7 and other black pigments.

In addition, examples of the aforementioned inorganic pigments include titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, red iron (red iron (III) oxide), cadmium red, ultramarine blue, iron Blue, chromium oxide green, cobalt green, umber, titanium black, synthetic iron black, carbon black, etc.

In the present invention, the pigment can also be used after being purified by recrystallization method, reprecipitation method, solvent washing method, sublimation method, vacuum heating method or a combination thereof. In addition, the pigment can be used after modifying the particle surface with a resin.

In addition, as said dye, it can select suitably from various oil-soluble dyes, direct dyes, acid dyes, metal complex dyes, etc., For example, the dye index (C.I.) name mentioned below is mentioned, for example.

Solvent yellow 4, C.I. solvent yellow 14, C.I. solvent yellow 15, C.I. solvent yellow 24, C.I. solvent yellow 82, C.I. solvent yellow 88, C.I. solvent yellow 94, C.I. solvent yellow 98, C.I. solvent yellow 162, C.I. solvent yellow 179, C.I. Acid Yellow 17, C.I. Acid Yellow 29, C.I. Acid Yellow 40, C.I. Acid Yellow 76 and other yellow dyes.

C.I. Solvent Orange 2, C.I. Solvent Orange 7, C.I. Solvent Orange 11, C.I. Solvent Orange 15, C.I. Solvent Orange 26, C.I. Solvent Orange 56, C.I. Acid Orange 51, C.I. Acid Orange 63 and other orange dyes.

C.I. Solvent Red 45, C.I. Solvent Red 49, C.I. Acid Red 91, C.I. Acid Red 92, C.I. Acid Red 97, C.I. Acid Red 114, C.I. Acid Red 138, C.I. Acid Red 151 and other red dyes.

C.I. Solvent Blue 35, C.I. Solvent Blue 37, C.I. Solvent Blue 59, C.I. Solvent Blue 67, C.I. Acid Blue 80, C.I. Acid Blue 83, C.I. Acid Blue 90 and other blue dyes.

C.I. Acid Green 9, C.I. Acid Green 16, C.I. Acid Green 25, C.I. Acid Green 27 and other green dyes.

In the present invention, the colored materials may be used alone or in combination of two or more.

When the photosensitive resin composition of the present invention contains a colored material, the content of the colored material is not particularly limited, for example, it is 1 to 30% by weight, preferably 3 to 15% by weight.

When the photosensitive resin composition of the present invention contains a colored material, the content of the colored material is not particularly limited, but relative to the solid content of the photosensitive resin composition, it is, for example, 1 to 30% by weight, preferably 3 to 15% by weight %. Here, the "solid content" refers to components other than the solvent that the photosensitive resin composition may contain, for example.

When the pigment is used as a colored material in the present invention, it may be used together with a pigment dispersant and a pigment dispersing aid if necessary. Examples of the aforementioned pigment dispersants include: cationic, anionic, nonionic, and amphoteric dispersants (surfactants); acrylic copolymers, polyesters, polyurethanes, polyethylene glycols, etc. Polymer dispersants such as imine and polyallylamine.

The above-mentioned pigment dispersant can be commercially available, for example, as an acrylic copolymer, for example, Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 (the above are manufactured by BYK-Chemie (BYK) company), as Polyester, for example, AJISPER PB821, AJISPER PB822, AJISPER PB880 (manufactured by Ajinomoto Fine-Techno Co., Ltd.), as polyurethane, for example, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-165, Disperbyk- 167. Disperbyk-170, Disperbyk-182 (manufactured by BYK-Chemie (BYK) Co.), Solsperse 76500 (manufactured by Lubrizol Co., Ltd.), as polyethyleneimine, Solsperse 24000 (manufactured by Lubrizol Co., Ltd. )wait.

These pigment dispersants can be used alone or in combination of two or more. The content of the pigment dispersant is not particularly limited, but relative to 100 parts by weight of the pigment, for example, it is less than 100 parts by weight, preferably 1 to 70 parts by weight, more preferably 10 to 70 parts by weight, and even more preferably 30 to 60 parts by weight share. When the content of the pigment dispersant is within the above-mentioned range, it tends to obtain a pigment dispersion liquid in a uniformly dispersed state, which is preferable.

Examples of the pigment dispersion aid include pigment derivatives, specifically, copper phthalocyanine, diketopyrrolopyrrole, sulfonic acid derivatives of quinoline yellow, and the like. The content of the pigment dispersion aid can be appropriately determined within the range that does not interfere with the object of the invention of the present invention. ＜Photopolymerizable compound＞

It does not specifically limit as a photopolymerizable compound of this invention, For example, a polyfunctional vinyl compound, a polyfunctional thiol compound, and a polyfunctional epoxy compound are mentioned.

The polyfunctional vinyl compound is not particularly limited as long as it is a compound having two or more vinyl groups, for example, di(meth)acrylates of alkanediols such as ethylene glycol and propylene glycol; polyethylene glycol; Two (meth)acrylates of polyalkylene glycols such as diol and polypropylene glycol; two-terminal hydroxylated polymers such as two-terminal hydroxyl polybutadiene, two-terminal hydroxyl polyisoprene, two-terminal hydroxyl polycaprolactone, etc. Two (meth)acrylates; glycerol, 1,2,4,-butanetriol, trimethylol alkane, tetramethylol alkane, neopentyl glycol, dipenteoerythritol, etc. Poly(meth)acrylates of alcohols; poly(meth)acrylates of polyalkylene glycol adducts of polyhydric alcohols with more than 3 valences; 1,4-cyclohexanediol, 1,4-benzenediol, etc. Poly(meth)acrylate of cyclic polyol; polyester (meth)acrylate, epoxy (meth)acrylate, urethane (meth)acrylate, silicone resin (meth)acrylate Oligomeric (meth)acrylates such as esters, etc. Among these, polyfunctional (meth)acrylates having two or more (meth)acryl groups are preferred. A polyfunctional vinyl compound can be used individually or in combination of 2 or more types.

The polyfunctional thiol compound is not particularly limited as long as it is a compound having two or more thiol groups, for example, hexanedithiol, decanedithiol, 1,4-butanediol dithiol Propionate, 1,4-Butanediol Dithioglycolate, Ethylene Glycol Dithioglycolate, Ethylene Glycol Dithiopropionate, Trimethylolpropane Trithioglycolate , Trimethylolpropane Trithiopropionate, Trimethylolpropane Tris(3-Mercaptobutyrate), Neopentylthritol Tetrathioglycolate, Neopentylthritol Tetrathiopropionate, Tris(2-hydroxyethyl)isocyanurate trimercaptopropionate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-tris, 2-(N,N-dibutyl Amino)-4,6-dimercapto-s-tris, tetraethylene glycol bis-3-mercaptopropionate, trimethylolpropane tris-3-mercaptopropionate, tris(3-mercaptopropynyloxyethyl ) isocyanurate, neopentylthritol tetra-3-mercaptopropionate, diperythritol tetra-3-mercaptopropionate, 1,4-bis(3-mercaptobutyryloxy)butane, 1 ,3,5-tris(3-mercaptobutoxyethyl)-1,3,5-tri-2,4,6(1H,3H,5H)-trione, neopentylthritol tetrakis(3- mercaptobutyrate), etc. The polyfunctional thiol compound can be used individually or in combination of 2 or more types.

The polyfunctional epoxy compound is not particularly limited as long as it is a compound having two or more epoxy groups, for example, glycidyl ether type epoxy compounds [by polyhydroxy compounds (bisphenols, Glycidyl ethers (such as ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, poly Ethylene glycol diglycidyl ether and other (poly) C _2-4 alkanediol diglycidyl ethers; diglycidyl ethers of polyphenols such as resorcinol and hydroquinone; cyclohexanediol, cyclohexanediol Diglycidyl ethers of alicyclic polyols such as methanol and hydrogenated bisphenols; bisphenols (4,4'-dihydroxybiphenyl, bis(hydroxyphenyl)alkanes such as bisphenol A, etc.) or their C Diglycidyl ether of _{2-3 alkylene oxide adducts} , etc.), novolak-type epoxy resins (phenol novolac-type or cresol-novolak-type epoxy resins, etc.), etc.], glycidyl ester-type epoxy compounds, Cycloaliphatic epoxy compounds (or cycloaliphatic epoxy resins), heterocyclic epoxy resins (triglycidyl isocyanurate (TGIC), hydantoin type epoxy resins, etc.), glycidylamine type Epoxy compounds [reaction products of amines and epichlorohydrin, such as N-glycidyl aromatic amines {tetraglycidyldiaminodiphenylmethane (TGDDM), triglycidylaminophenol (TGPAP, TGMAP etc.), diglycidyl aniline (DGA), diglycidyl toluidine (DGT), tetraglycidyl xylylenediamine (TGMXA, etc.), etc.}, N-glycidyl cycloaliphatic amine (tetraglycidyl base diaminocyclohexane, etc.), etc.] and so on.

A polyfunctional epoxy compound can be used individually or in combination of 2 or more types.

A photopolymerizable compound can be used individually or in mixture of 2 or more types. The content of the photopolymerizable compound is not particularly limited, but is, for example, preferably 1 to 100 parts by weight, more preferably 5 to 60 parts by weight, and further preferably 10 to 40 parts by weight relative to 100 parts by weight of the aforementioned alkali-soluble resin.

In addition, when the photosensitive resin composition of the present invention contains a colored material, the content of the photopolymerizable compound is not particularly limited, but relative to 100 parts by weight of the aforementioned colored material, for example, it is preferably 10 to 800 parts by weight, more preferably 50 parts by weight. to 500 parts by weight, more preferably 200 to 300 parts by weight. When content of a photopolymerizable compound is the said range, hardening will fully arise and favorable adhesiveness will be acquired. ＜Photopolymerization Initiator＞

In the present invention, the photopolymerization initiator is not particularly limited, and examples thereof include photoradical polymerization initiators and photocationic polymerization initiators.

The photoradical polymerization initiator is a compound that generates radicals by light irradiation and starts the hardening reaction (radical polymerization) of the photopolymerizable compound contained in the photosensitive resin composition. A photoradical polymerization initiator can be used individually or in mixture of 2 or more types.

系化合物、苯乙酮系化合物、聯咪唑系化合物、三系化合物、肟系化合物、鎓鹽系化合物、安息香系化合物、二苯甲酮系化合物、α-二酮系化合物、多核醌系化合物、重氮系化合物、醯亞胺磺酸鹽系化合物、蒽系化合物等。 As a photoradical polymerization initiator, for example, 9-oxosulfur

Acetophenone-based compounds, biimidazole-based compounds, tri-series compounds, oxime-based compounds, onium salt-based compounds, benzoin-based compounds, benzophenone-based compounds, α-diketone-based compounds, polynuclear quinone-based compounds , diazo compounds, imide sulfonate compounds, anthracene compounds, etc.

系化合物，例如可舉例為：9-氧硫

、2-氯9-氧硫

、2-甲基9-氧硫

、2-異丙基9-氧硫

、4-異丙基9-氧硫

、2,4-二甲基9-氧硫

、2,4-二乙基9-氧硫

、2,4-二異丙基9-氧硫

、2,4-二氯9-氧硫

、1-氯-4-丙氧基9-氧硫

等。 As the aforementioned 9-oxosulfur

series compounds, such as: 9-oxosulfur

, 2-chloro 9-oxysulfur

, 2-methyl 9-oxosulfur

, 2-isopropyl 9-oxosulfur

, 4-isopropyl 9-oxosulfur

, 2,4-Dimethyl 9-oxosulfur

, 2,4-Diethyl 9-oxosulfur

, 2,4-Diisopropyl 9-oxosulfur

, 2,4-dichloro-9-oxosulfur

, 1-Chloro-4-propoxy 9-oxosulfur

wait.

啉基丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-

啉基苯基)丁烷-1-酮、2-(2-甲基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(3-甲基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(4-甲基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-乙基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-丙基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-丁基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2,3-二甲基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2,4-二甲基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-氯苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-溴苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(3-氯苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(4-氯苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(3-溴苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(4-溴苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-甲氧基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(3-甲氧基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(4-甲氧基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-甲基-4-甲氧基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-甲基-4-溴苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-(2-溴-4-甲氧基苄基)-2-二甲基胺基-1-(4-

啉基苯基)-丁酮、2-羥基-2-甲基-1-[4-(1-甲基乙烯基）苯基]丙烷-1-酮之低聚物等。Examples of the aforementioned acetophenone-based compounds include: diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzoyldimethylketal, 2 -Hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropane-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methyl thiophenyl)-2-

Linyl propan-1-one, 2-benzyl-2-dimethylamino-1-(4-

Linylphenyl) butan-1-one, 2-(2-methylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(3-methylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(4-methylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-ethylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-propylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-butylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2,3-dimethylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2,4-dimethylbenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-chlorobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-bromobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(3-chlorobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(4-chlorobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(3-bromobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(4-bromobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-methoxybenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(3-methoxybenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(4-methoxybenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-methyl-4-methoxybenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-methyl-4-bromobenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, 2-(2-bromo-4-methoxybenzyl)-2-dimethylamino-1-(4-

Linylphenyl)-butanone, oligomers of 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1-one, etc.

As the aforementioned biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2, 3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl Biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl) base)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra (trialkoxyphenyl)biimidazole, imidazole compounds in which the phenyl at the 4,4'5,5'-position is substituted by an alkoxycarbonyl group, etc.

、2,4-雙(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三、2,4-雙(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三、2,4-雙(三氯甲基)-6-[2-(4-二乙基胺基-2-甲基苯基)乙烯基]-1,3,5-三、2,4-雙(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三等。 Examples of the aforementioned tris-series compounds include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-tris-series compounds, 2,4-bis (Trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-tri, 2,4-bis(trichloromethyl)-6-helianthyl-1,3,5 -Triple, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-tri

, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-tri, 2,4-bis(trichloro Methyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-tri, 2,4-bis(trichloromethyl)-6-[2-(4-di Ethylamino-2-methylphenyl)vinyl]-1,3,5-tri, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxy phenyl)vinyl]-1,3,5-tri and so on.

As said oxime compound, O-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one etc. are mentioned, for example.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

Examples of the aforementioned benzophenone-based compounds include: benzophenone, methyl o-phthalbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenone, Phenyl sulfide, 3,3',4,4'-tetrakis(tertiary butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, etc.

Examples of the aforementioned anthracene-based compounds include: 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl -9,10-diethoxyanthracene, etc.

The aforementioned photocationic polymerization initiator is a compound that generates an acid by light irradiation and initiates the hardening reaction (cationic polymerization) of the photopolymerizable compound contained in the photosensitive resin composition, and includes a cationic part that absorbs light and becomes The anion part of the source of acid generation. A photocationic polymerization initiator can be used individually or in combination of 2 or more types.

鹽系化合物、銨鹽系化合物、溴鎓鹽系化合物等。 As a photocationic polymerization initiator, for example, a diazonium salt-based compound, an iodonium salt-based compound, a perulium salt-based compound, a phosphonium salt-based compound, a selenium salt-based compound,

Salt-based compounds, ammonium-based compounds, bromium-based compounds, etc.

As the anion portion of the photocationic polymerization initiator, for example, it can be exemplified as: [(Y) _s B(Phf) _4-s ]-(wherein, Y represents a phenyl group or a biphenyl group. Phf represents that at least one hydrogen atom is At least one substituted phenyl group selected from perfluoroalkyl, perfluoroalkoxy, and halogen atoms. s is an integer from 0 to 3), BF ₄ ^- , [(Rf) _k PF _6-k ] ^- (Rf: an alkyl group in which more than 80% of hydrogen atoms are replaced by fluorine atoms, k: an integer from 0 to 5), AsF ₆ ^- , SbF ₆ ^- , SbF ₅ OH ^- , etc.

基硫基)苯基]苯基-2-硫9-氧硫

基鋶苯基三(五氟苯基)硼酸鹽、4-(苯基硫基)苯基二苯基鋶六氟銻酸鹽等。 As photocationic polymerization initiators, for example, (4-hydroxyphenyl) methylbenzyl percite tetrakis(pentafluorophenyl) borate, 4-(4-biphenylthio)phenyl-4 -Biphenylphenylpermetrakis tetrakis (pentafluorophenyl) borate, 4-(phenylsulfanyl)phenyldiphenylperjulyphenyl tris(pentafluorophenyl)borate, [4-(4-bi Phenylsulfanyl)phenyl]-4-biphenylphenylperzylphenyltris(pentafluorophenyl)borate base) trifluorophosphate, diphenyl[4-(phenylthio)phenyl]percitetetrakis(pentafluorophenyl)borate, diphenyl[4-(phenylthio)phenyl]percite Fluorophosphate, 4-(4-biphenylsulfanyl)phenyl-4-biphenylphenylsulfanyl tris(pentafluoroethyl)trifluorophosphate, bis[4-(diphenyldihydrogenthio) ) phenyl] sulfide phenyl tris(pentafluorophenyl) borate, [4-(2-sulfur 9-oxosulfur

Sulfuryl)phenyl]phenyl-2-sulfur 9-oxosulfur

phenyl percited tris(pentafluorophenyl)borate, 4-(phenylsulfanyl)phenyldiphenyl percited hexafluoroantimonate, etc.

As the photocationic polymerization initiator, can be used: trade names "Cyracure UVI-6970", "Cyracure UVI-6974", "Cyracure UVI-6990", "Cyracure UVI-950" (the above are manufactured by Union Carbide, USA), "Irgacure250", "Irgacure261", "Irgacure264" (the above are manufactured by BASF), "CG-24-61" (manufactured by Ciba-Geigy), "OPTMER SP-150", "OPTMER SP-151", "OPTMER SP-170", "OPTMER SP-171" (the above are manufactured by ADEKA Co., Ltd.), "DAICAT II" (manufactured by Daicel Co., Ltd.), "UVAC1590", "UVAC1591" (the above are manufactured by Daicel-Cytec Co., Ltd. ), "CI-2064", "CI-2639", "CI-2624", "CI-2481", "CI-2734", "CI-2855", "CI-2823", "CI-2758", "CIT-1682" (manufactured by Nippon Soda Co., Ltd. above), "PI-2074" (manufactured by Rhodia Corporation, toluylcumyl iodonium tetrakis(pentafluorophenyl) borate), "FFC509" (manufactured by 3M Company), "BBI-102", "BBI-101", "BBI-103", "MPI-103", "TPS-103", "MDS-103", "DTS-103", "NAT -103", "NDS-103" (manufactured by Midori Kagaku Co., Ltd.), "CD-1010", "CD-1011", "CD-1012" (manufactured by Sartomer, USA), "CPI-100P ", "CPI-101A" (manufactured by San-Apro Co., Ltd. above) and other commercially available products.

The content of the photopolymerization initiator (the total amount when two or more types are contained) is, for example, 0.1 to 10 parts by weight relative to 100 parts by weight of the photopolymerizable compound (total amount) contained in the photosensitive resin composition , preferably 0.5 to 5 parts by weight, more preferably 1 to 3 parts by weight. When content of a photoinitiator is less than the said range, it exists in the tendency for curability to fall. On the other hand, when the content of the photopolymerization initiator exceeds the above-mentioned range, the cured product tends to be easily colored. <Solvent>

As solvents, for example, ethers (diethyl ether; ethylene glycol mono- or dialkyl ethers, diethylene glycol mono- or dialkyl ethers, propylene glycol mono- or dialkyl ethers, propylene glycol mono- or diaryl ethers, Dipropylene glycol mono or dialkyl ether, tripropylene glycol mono or dialkyl ether, 1,3-propanediol mono or dialkyl ether, 1,3-butanediol mono or dialkyl ether, 1,4-butanediol Chain ethers such as alcohol mono- or dialkyl ethers, glycerin mono-, di- or tri-alkyl ethers and other glycol ethers; tetrahydrofuran, diane and other cyclic ethers, etc.), esters (methyl acetate, ethyl acetate, acetic acid Butyl ester, isoamyl acetate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, C _5-6 cycloalkanediol mono or diacetate, C _{5- 6} Naphthene dimethanol mono or diacetate and other carboxylic acid esters; ethylene glycol monoalkyl ether acetate, ethylene glycol mono or diacetate, diethylene glycol monoalkyl ether acetate, Diethylene glycol mono or diacetate, propylene glycol monoalkyl ether acetate, propylene glycol mono or diacetate, dipropylene glycol monoalkyl ether acetate, dipropylene glycol mono or diacetate, 1,3 - Propylene Glycol Monoalkyl Ether Acetate, 1,3-Propanediol Mono or Diacetate, 1,3-Butanediol Monoalkyl Ether Acetate, 1,3-Butanediol Mono or Diacetate , 1,4-butanediol monoalkyl ether acetate, 1,4-butanediol mono or diacetate, glycerol mono, di or triacetate, glycerol mono or di C _1-4 alkyl Ether di- or mono-acetate, tripropylene glycol monoalkyl ether acetate, tripropylene glycol mono- or diacetate and other glycol acetates or glycol ether acetates, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 3,5,5-trimethyl-2-cyclohexen-1-one, etc.), etc. These solvents may be used alone or in combination of two or more.

In addition to the above components, the photosensitive resin composition of the present invention may also contain resins such as novolac resins, phenol resins, imide resins, resins containing carboxyl groups, hardeners, hardening accelerators, additives (fillers, defoamers, etc.) additives, flame retardants, antioxidants, UV absorbers, colorants, stress reducing agents, flexibility imparting agents, waxes, resins, crosslinking agents, halogen scavengers, leveling agents, wetting modifiers, etc.) .

The content of the alkali-soluble resin in the photosensitive resin composition of the present invention is not particularly limited, for example, preferably 5 to 80% by weight, more preferably 10 to 70% by weight, further preferably 15 to 60% by weight, especially Preferably it is 20 to 55% by weight.

In addition, the content of the alkali-soluble resin is, for example, preferably 15 to 75% by weight, more preferably 20 to 70% by weight, further preferably 25 to 60% by weight, and especially preferably 30 to 55% by weight. At this time, it is preferable that the photosensitive resin composition does not contain a coloring material.

The nitrogen atom content of the hardening compound product is, for example, 5 to 70% by weight, preferably 10 to 60% by weight, more preferably 15 to 50% by weight, and most preferably 20 to 40% by weight. At this time, it is preferable that the photosensitive resin composition contains a colored material.

The content of the alkali-soluble resin in the photosensitive resin composition of the present invention is not particularly limited, for example, it is preferably 30 to 95% by weight, more preferably 40 to 90% by weight relative to the solid content of the photosensitive resin composition , further preferably from 50 to 85% by weight, especially preferably from 60 to 80% by weight. Here, the "solid content" refers to components other than the solvent that the photosensitive resin composition may contain, for example.

In addition, the content of the alkali-soluble resin is, for example, preferably 40 to 90% by weight, more preferably 50 to 85% by weight, and even more preferably 60 to 80% by weight relative to the solid content of the photosensitive resin composition. At this time, it is preferable that the photosensitive resin composition does not contain a coloring material.

In addition, the content of the alkali-soluble resin is, for example, preferably 40 to 90% by weight, more preferably 50 to 80% by weight, and even more preferably 60 to 75% by weight relative to the solid content of the photosensitive resin composition. At this time, it is preferable that the photosensitive resin composition contains a colored material.

The content of the photopolymerizable compound in the photosensitive resin composition of the present invention is not particularly limited, for example, preferably 1 to 60% by weight, more preferably 2 to 40% by weight, further preferably 3 to 30% by weight, Especially preferred is 5 to 20% by weight.

In addition, the content of the photopolymerizable compound is, for example, preferably 3 to 40% by weight, more preferably 5 to 30% by weight, further preferably 8 to 25% by weight, and especially preferably 10 to 20% by weight. At this time, it is preferable that the photosensitive resin composition does not contain a coloring material.

In addition, the content of the photopolymerizable compound is, for example, preferably from 2 to 30% by weight, more preferably from 3 to 20% by weight, further preferably from 5 to 15% by weight. At this time, it is preferable that the photosensitive resin composition contains a colored material.

The content of the photopolymerizable compound in the photosensitive resin composition of the present invention is not particularly limited, for example, it is preferably 3 to 60% by weight, more preferably 5 to 50% by weight relative to the solid content of the photosensitive resin composition %, more preferably 10 to 40% by weight, especially preferably 15 to 30% by weight.

In addition, the content of the photopolymerizable compound is, for example, preferably 5 to 50% by weight, more preferably 10 to 40% by weight, further preferably 15 to 30% by weight, and especially Preferably it is 18 to 25% by weight. At this time, it is preferable that the photosensitive resin composition does not contain a coloring material.

In addition, the content of the photopolymerizable compound is, for example, preferably 5 to 40% by weight, more preferably 10 to 30% by weight, and further preferably 15 to 25% by weight relative to the solid content of the photosensitive resin composition. At this time, it is preferable that the photosensitive resin composition contains a colored material.

As a method of preparing the photosensitive resin composition of this invention, the method of dissolving an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, and other additives as needed in a solvent, etc. are mentioned, for example.

In addition, when the photosensitive resin composition of the present invention contains a colored material, as a method of preparing the photosensitive resin composition, for example, the following method can be exemplified: in a solvent, if necessary, a pigment dispersant is coexisted and the pigment, etc. are colored. The material is dispersed, and the colored material dispersion is prepared, and the alkali-soluble resin, photopolymerizable compound, photopolymerization initiator, and other additives as necessary are dissolved in the solvent, and it is mixed with the aforementioned colored material dispersion, depending on Further addition of solvent is required.

The photosensitive resin composition of the present invention is usually enclosed in a container for distribution and storage. The photosensitive resin composition of the present invention is excellent in storage stability during distribution and storage. ＜hardened material＞

A cured product excellent in various physical properties is obtained by curing the aforementioned photosensitive resin composition of the present invention. For example, the above-mentioned photosensitive resin composition is applied to various substrates or substrates by conventional coating means such as spin coater, dip coater, roll coater, and slit coater to form a coating film. The aforementioned coating film is hardened, whereby a hardened product can be obtained. Curing can be performed, for example, by subjecting the photosensitive resin composition to light irradiation and/or heat treatment.

It is preferable to use, for example, a mercury lamp, a xenon lamp, a carbon arc lamp, a metal halide lamp, sunlight, an electron beam source, a laser light source, an LED light ^source , etc. for the aforementioned light irradiation. Internal exposure.

The aforementioned heat treatment is preferably performed at a temperature of, for example, 60 to 300° C. (preferably 100 to 250° C.) for 1 to 120 minutes (preferably 1 to 60 minutes).

As the base material or substrate, for example: silicon wafer, metal, plastic, glass, ceramics and the like. The thickness of the cured coating film is, for example, preferably 0.05 to 20 µm, more preferably 0.1 to 10 µm.

The cured product (coating film after curing) of the present invention is excellent in solvent resistance and has high insulation properties, so it can be used as a protective film (color filter protective film, etc.) and insulating film, or a material for forming microlenses, etc. . ＜Color Filter＞

The color filter of the present invention has a colored pattern formed of a photosensitive resin composition containing a colored material. A color filter can be manufactured, for example, through the step of forming a colored pattern using the aforementioned photosensitive resin composition on a substrate, and the step of post-baking the aforementioned colored pattern.

As a method of forming a pattern of a color filter using the above-mentioned photosensitive resin composition, for example, the following method can be exemplified: the above-mentioned photosensitive resin composition is applied to a substrate or substrate by a conventional coating means such as a spin coater. On other resin layers, volatile components such as solvents are removed to form colored layers, and the colored layers are exposed and developed through a photomask.

Examples of substrates include glass substrates, silicon substrates, polycarbonate substrates, polyester substrates, aramid substrates, polyamideimide substrates, polyimide substrates, Al substrates, GaAs substrates, etc. Substrates with flat surfaces, etc. These substrates may also undergo pretreatments such as chemical treatment using chemicals such as silane coupling agents, plasma treatment, ion plating treatment, sputtering treatment, gas phase reaction treatment, and vacuum evaporation treatment.

The thickness of the colored layer after drying is, for example, 0.6 to 8 µm, preferably 1 to 5 µm.

As the light source of radiation used for exposure, for example, light sources such as xenon lamps, halogen lamps, tungsten lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, medium-pressure mercury lamps, and low-pressure mercury lamps, and argon ion lasers, YAG laser, XeCl excimer laser, nitrogen laser and other laser light sources, etc. The wavelength of the radiation is preferably in the range of 190 to 450 nm. The exposure dose of radiation is generally preferably 10 to 10,000 J/m ² .

As an alkaline developer used for development, for example, sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo-[5.4.0]-7- Aqueous solutions of undecene, 1,5-diazabicyclo-[4.3.0]-5-nonene, etc.

The post-baking conditions are generally 120 to 280° C. for 10 to 60 minutes. The film thickness of the pixels thus formed is usually 0.5 to 5 µm, preferably 1 to 3 µm.

According to the photosensitive resin composition of the present invention, a colored pattern having excellent curing reactivity and sufficient solvent resistance can be obtained. <Members for display devices or display devices>

A member for a display device or a display device according to the present invention includes the aforementioned color filter. As the said display device member, a color liquid crystal display element is mentioned, for example. Moreover, as said display device, a color liquid crystal display device is mentioned, for example. The structure of the color liquid crystal display element or the color liquid crystal display is not particularly limited, and an appropriate structure can be adopted.

Furthermore, various aspects disclosed in this specification can also be combined with any other features disclosed in this specification. In addition, each structure in each embodiment, their combination, etc. are an example, and addition, omission, and other changes of a structure can be suitably made in the range which does not deviate from the summary of this invention. The present invention is not limited by the embodiments, but only by the scope of the patent application. Example

Hereinafter, although an Example demonstrates this invention in more detail, this invention is not limited to these Examples. In addition, the weight average molecular weight (polystyrene conversion) and molecular weight dispersion (weight average molecular weight Mw/number average molecular weight Mn) of a copolymer were measured with the following apparatus. Device: Detector: RID-20A (Shimadzu Corporation) Pump: LC-20AD (Shimadzu Corporation) System controller: CBM-20Alite (Shimadzu Corporation) Degassing unit: DGU-20A3 (Shimadzu Corporation) Autoinjector: SIL-20A HT (Shimadzu Corporation) String: Shodex KF-806L (Showa Denko) Eluent: THF (tetrahydrofuran) 0.8 ml/min Temperature: Oven: 40°C, RI: 40°C Detector: RI [Synthesis Example 1/Production of Monomer B1] (first step)

A solution containing 213 g of 1,2-epoxy-9-decene and 60 g of 2-hydroxyethyl methacrylate was kept at 38°C, and 1.9 g of boron trifluoride was added dropwise over 2 hours. A solution of 18 g of the ether complex in ethyl acetate was stirred for 3 hours. Thereafter, after adding 250 g of ethyl acetate and 220 g of water and stirring, the organic phase was recovered. The organic phase is 526 g. The concentrations of 2-hydroxyethyl methacrylate and ethyl acetate contained in the organic phase measured by gas chromatography were 0.9% by weight and 48.3% by weight, respectively. The remaining 50.8% by weight was regarded as a 1,2-epoxy-9-decene adduct (crude product) of 2-hydroxyethyl methacrylate, and was used in the next step. In addition, the average addition number of 1,2-epoxy-9-decene of the said adduct measured by ¹ H-NMR was 3.0. (second step)

140 mg of p-methoxyphenol was dissolved in 200 g of 2-hydroxyethyl methacrylate 1,2-epoxy-9-decene adduct (crude product) obtained in the first step. For the resulting solution, While maintaining the internal temperature at 50° C. or lower, 143 g of an ethyl acetate solution of 28% by weight of peracetic acid was added over 2 hours. Thereafter, it was stirred at 55°C for 7 hours. After confirming the disappearance of the raw material (1,2-epoxy-9-decene adduct of 2-hydroxyethyl methacrylate) by NMR, cool to room temperature, wash once with 340 g of water and separate the water layer . Then, after adding and washing 120 g of 10 weight% sodium hydroxide aqueous solution to the organic layer, the aqueous layer was isolate|separated, and the organic layer was wash|cleaned twice with water further, and the aqueous layer was isolate|separated. Then, low boiling point components, such as a solvent, were removed using the evaporator on conditions of 40 degreeC, 10 mmHg, and 2 hours, and 70 g of target monomers B1 were obtained. Also, the yield was 80%. The yield was calculated from the actually obtained yield of the monomer B1 relative to the theoretical yield calculated from the amount of the raw material (2-hydroxyethyl methacrylate) used. [Synthesis Example 2/Production of Monomer B2] (first step)

While maintaining a solution of 200 g of 1,2-epoxy-4-vinylcyclohexane and 70 g of 2-hydroxyethyl methacrylate at 38°C, 1.9 g of trifluoroethylene was added dropwise over 2 hours. A solution of 18 g of boron diethyl ether complex in ethyl acetate was stirred for 3 hours. Thereafter, after adding 252 g of ethyl acetate and 224 g of water and stirring, the organic phase was recovered. The organic layer was 524 g. The concentrations of 2-hydroxyethyl methacrylate and ethyl acetate contained in the organic phase measured by gas chromatography were 1.2% by weight and 47.8% by weight, respectively. The remaining 51% by weight was used in the next step as a 1,2-epoxy-4-vinylcyclohexane adduct (crude product) of 2-hydroxyethyl methacrylate. In addition, the average addition number of 1,2-epoxy-4-vinylcyclohexane of the said adduct measured by ¹ H-NMR was 3.0. (second step)

140 mg of p-methoxyphenol was dissolved in the crude product of 200 g of 2-hydroxyethyl methacrylate adducted with 1,2-epoxy-4-vinylcyclohexane obtained in the first step. To the solution, 182 g of an ethyl acetate solution of 28% by weight of peracetic acid was added over 2 hours while maintaining the internal temperature at 50° C. or lower. Thereafter, stirring was carried out at 55° C. for 7 hours. After confirming the disappearance of the raw material (1,2-epoxy-4-vinylcyclohexane adduct of 2-hydroxyethyl methacrylate) by NMR, cool to room temperature, wash once with 400 g of water and Separate the aqueous layer. Then, after adding and washing 132 g of 10 weight% sodium hydroxide aqueous solution to the organic layer, the aqueous layer was isolate|separated, and the organic layer was wash|cleaned twice with water further, and the aqueous layer was isolate|separated. Then, low boiling point components, such as a solvent, were removed using the evaporator on conditions of 40 degreeC, 10 mmHg, and 2 hours, and 94.0 g of target monomers B2 were obtained. Also, the yield was 84%. The yield was calculated from the actually obtained yield of the monomer B2 relative to the theoretical yield calculated from the amount of the raw material (2-hydroxyethyl methacrylate) used. [manufacturing example 1]

In a 1L flask equipped with a reflux cooler, a dropping funnel and a stirrer, flow an appropriate amount of nitrogen to form a nitrogen atmosphere, add 150 parts by weight of propylene glycol monomethyl ether acetate to the aforementioned flask, and heat to 80°C while stirring . Thereafter, in the aforementioned flask, 10 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) dissolved in 40 parts by weight of propylene glycol monohydrate was dropped for about 4 hours, respectively. A solution made of methyl ether acetate, and a solution made of 15 parts by weight of acrylic acid (AA) and 85 parts by weight of monomer B1 dissolved in 10 parts by weight of propylene glycol monomethyl ether acetate. After completion of the dropping, the same temperature was maintained for 4 hours, and then cooled to room temperature to obtain a copolymer solution having a solid content of 35.7% by weight. The resulting copolymer had a weight average molecular weight Mw of 10,500 and a molecular weight dispersion of 3.25. [Manufacturing example 2]

Except having used 15 weight part of acrylic acid (AA) and 85 weight part of monomer B2 as a monomer, the same operation as manufacture example 1 was performed, and the copolymer solution of 35.1 weight% of solid content was obtained. The resulting copolymer had a weight average molecular weight Mw of 10,300 and a molecular weight dispersion of 3.56. [Manufacturing example 3]

Except using 15 parts by weight of acrylic acid (AA), 65 parts by weight of monomer B2, and 20 parts by weight of styrene (ST) as monomers, the same operation as in Production Example 1 was carried out to obtain a solid content of 34.1 wt. % copolymer solution. The weight average molecular weight Mw of the resulting copolymer was 8,800, and the molecular weight dispersion was 3.18. [Manufacturing example 4]

Except using 15 parts by weight of acrylic acid (AA), 65 parts by weight of monomer B2, and 20 parts by weight of methyl methacrylate (MMA) as monomers, the same operation as in Production Example 1 was carried out to obtain a solid A copolymer solution with a composition of 34.8% by weight. The weight average molecular weight Mw of the resulting copolymer was 9,700, and the molecular weight dispersion was 3.10. [Manufacturing example 5]

Except using 15 parts by weight of acrylic acid (AA), 65 parts by weight of monomer B2, and 20 parts by weight of N-cyclohexylmaleimide as monomers, the same operation as in Production Example 1 was carried out, and A copolymer solution having a solid content of 35.2% by weight was obtained. The weight average molecular weight Mw of the resulting copolymer was 9,400, and the molecular weight dispersion was 3.20. [Manufacturing example 6]

In a 1L flask equipped with a reflux cooler, a dropping funnel and a stirrer, an appropriate amount of nitrogen gas was flowed into a nitrogen atmosphere, and 150 parts by weight of propylene glycol monomethyl ether acetate was added, and heated to 65°C while stirring. Thereafter, in the aforementioned flask, 10 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in 40 parts by weight of propylene glycol monomethanol in about 4 hours. A solution made of ether acetate, and as a monomer, 15 parts by weight of acrylic acid (AA), 65 parts by weight of glycidyl methacrylate (GMA), and 20 parts by weight of methyl methacrylate (MMA) A solution obtained by dissolving in 10 parts by weight of propylene glycol monomethyl ether acetate. After completion of the dropping, the same temperature was maintained for about 4 hours, and then cooled to room temperature to obtain a copolymer solution having a solid content of 34.5% by weight. The resulting copolymer had a weight average molecular weight Mw of 8,000 and a molecular weight dispersion of 1.90. [Manufacturing example 7]

In addition to using 15 parts by weight of acrylic acid (AA), 60 parts by weight of 3,4-epoxycyclohexylmethyl methacrylate (Cyclomer M100), and 20 parts by weight of methyl methacrylate (MMA) as monomers , The same operation as in Production Example 6 was carried out to obtain a copolymer solution with a solid content of 33.8% by weight. The weight average molecular weight Mw of the resulting copolymer was 8,200, and the molecular weight dispersion was 1.91. [Manufacturing example 8]

In addition to using 15 parts by weight of acrylic acid (AA), 60 parts by weight of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-9-yl ester and 3,4-epoxytricyclo[5.2 .1.0 ^2,6 ] Dec-8-yl ester mixture (monomer B3), 20 parts by weight of methyl methacrylate (MMA) as a monomer, the same operation as in Production Example 6 was carried out to obtain a solid A copolymer solution with a composition of 35.1% by weight. The resulting copolymer had a weight average molecular weight Mw of 9,300 and a molecular weight dispersion of 2.04.

Table 1 shows the copolymer composition, the weight average molecular weight of the copolymer, and the degree of dispersion in Production Examples 1 to 8. [Example 1]

8.09 g of the copolymer obtained in the above-mentioned Production Example 1 as an alkali-soluble resin, 2.25 g of DPHA as a photopolymerizable compound, and 0.20 g of 1-hydroxycyclohexylbenzene as a solution containing a copolymer were measured in a container. Photosensitive resin composition 1 was prepared by stirring for 30 minutes using ketone as a photopolymerization initiator and 6.83 g of MMPGAC as a solvent. [Example 2]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 2 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 1, and prepared the photosensitive resin composition 2. [Example 3]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 3 which was the solution containing a copolymer as an alkali-soluble resin, the same operation as Example 1 was performed, and the photosensitive resin composition 3 was prepared. [Example 4]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 4 which was the solution containing a copolymer as an alkali-soluble resin, the same operation as Example 1 was performed, and the photosensitive resin composition 4 was prepared. [Example 5]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 5 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 1, and prepared the photosensitive resin composition 5. [Comparative example 1]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 6 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 1, and prepared the photosensitive resin composition 6. [Comparative example 2]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 7 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 1, and prepared the photosensitive resin composition 7. [Comparative example 3]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 8 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 1, and prepared the photosensitive resin composition 8. [Example 6]

Measure 7.7g of C.I. Pigment Red 254 as the color material, 3.1g of DISPERBYK-2000 as the dispersant, and 36.0g of MMPGAC as the solvent in the container, add 45g of zirconia beads with a diameter of 1.0mm, and cover cover. This was shaken for 3 hours using a paint shaker. After 3 hours, the pigment dispersion liquid and the zirconia beads were separated, 45 g of 0.5 mm zirconia beads were added, and the paint shaker was further shaken for 3 hours. Thereafter, the pigment dispersion was separated from the zirconia beads, 45 g of 0.3 mm zirconia beads were added, and after further shaking for 3 hours using a paint shaker, the zirconia beads were separated to obtain a pigment dispersion. In a container, 8.09 g of the copolymer obtained in the above-mentioned Production Example 1 as an alkali-soluble resin and 2.25 g of DPHA as a photopolymerizable compound were measured for 4.68 g of the obtained pigment dispersion liquid as a solution containing a copolymer. , 0.20 g of 1-hydroxycyclohexyl phenyl ketone as a photopolymerization initiator, 18.8 g of MMPGAC as a solvent, and stirred for 30 minutes to prepare a colored photosensitive resin composition 1 . [Example 7]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 2 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and the colored photosensitive resin composition 2 was prepared. [Example 8]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 3 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and the colored photosensitive resin composition 3 was prepared. [Example 9]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 4 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and the colored photosensitive resin composition 4 was prepared. [Example 10]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 5 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and the colored photosensitive resin composition 5 was prepared. [Comparative example 4]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 6 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and prepared the colored photosensitive resin composition 6. [Comparative Example 5]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 7 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and prepared the colored photosensitive resin composition 7. [Comparative Example 6]

Except having used 8.09 g of the copolymer obtained in the said manufacture example 8 which is the solution containing a copolymer as an alkali-soluble resin, it carried out similarly to Example 6, and the colored photosensitive resin composition 8 was prepared.

In Table 2, the compositions of the photosensitive resin compositions of Examples and Comparative Examples are described. In addition, in Table 3, the composition of the colored photosensitive resin composition of an Example and a comparative example is described. ＜Evaluation test＞

The following evaluation tests were performed using each resin composition obtained in Examples and Comparative Examples. The results are shown in Tables 4 and 5. (1) Storage stability test

The photosensitive resin compositions and colored photosensitive resin compositions obtained in Examples and Comparative Examples were stored in an oven at 23° C. for one week. The viscosity immediately after polymerization and the viscosity after storage at 23°C for 1 week were measured. Use the following formula to calculate the viscosity increase rate. In addition, the viscosity (unit: mPa･s) was measured using a viscometer (trade name "LVDV2T", manufactured by Brookfield Corporation) at a rotation speed of 60 and a temperature of 23°C. P: Viscosity immediately after polymerization, Q: Viscosity after storage at 23°C for 1 week Viscosity increase rate={(Q/P)×100}-100 (2) Solvent resistance test-1

The photosensitive resin compositions and colored photosensitive resin compositions obtained in Examples and Comparative Examples were coated on glass plates using a spin coater, and then cured by heating at 150° C. for 30 minutes to prepare test pieces. The thickness of the cured coating film of the photosensitive resin composition is 3 µm. The thickness of the cured coating film of the colored photosensitive resin composition was 4 µm.

One drop of each of γ-butyrolactone (γ-BL) and N-methylpyrrolidone (NMP) was dropped on the test piece, and left to stand for 10 minutes. After washing with water, if there is no change in the part where the solvent was dropped, it is ◎; if there is only traces of solvent remaining but disappears after wiping, then it is ○; if traces of solvent remain and does not disappear even after wiping, then it is △; for ×. (3) Solvent resistance test-2

The solvent resistance test of the cured product was performed in the same manner as in the solvent resistance test-1 except that the curing temperature was set to 230° C. during preparation of the test piece.

The photosensitive resin composition of Examples 1 to 5 is not easy to thicken even at 23°C, and has good storage stability. In addition, even if the curing temperature is 150°C, it exhibits good solvent resistance similarly to the case of 230°C. On the other hand, the photosensitive resin compositions of Comparative Examples 1 and 2 were also poor in storage stability based on their gelation at 23°C. In addition, although the photosensitive resin composition of Comparative Example 3 has good storage stability by using the monomer B3 (E-DCPA), if the curing temperature is lowered from 230°C to 150°C, it is not sufficiently cured, so it is known that the photosensitive resin composition is resistant to Reduced solvent resistance.

The colored photosensitive resin compositions of Examples 6 to 10 are not easy to increase viscosity even at 23° C., and have good storage stability. In addition, even if the curing temperature is 150°C, it exhibits good solvent resistance similarly to the case of 230°C. On the other hand, the colored photosensitive resin compositions of Comparative Examples 4 and 5 also had poor storage stability based on their viscosity increase at 23°C. In addition, although the colored photosensitive resin composition of Comparative Example 6 has good storage stability by using the monomer B3 (E-DCPA), if the curing temperature is lowered from 230°C to 150°C, it is not sufficiently cured, so it can be seen that Reduced solvent resistance.

◎[Table 1] Manufacturing example 1 Manufacturing example 2 Manufacturing example 3 Manufacturing example 4 Manufacturing Example 5 Manufacturing example 6 Manufacturing example 7 Manufacturing example 8 Alkali soluble resin composition (A) Ingredients acrylic acid parts by weight 15 15 15 15 15 15 15 15 (B) Ingredients Monomer B1 parts by weight 85 Monomer B2 parts by weight 85 65 65 65 GMA parts by weight 65 Cyclomer M100 parts by weight 65 Monomer B3 parts by weight 65 (C) Ingredients ST parts by weight 20 MMA parts by weight 20 10 10 CHMI parts by weight 20 solvent MMPGAC parts by weight 200 200 200 200 200 200 200 200 character GPC mw - 10,500 10,300 8,800 9,700 9,400 8,000 8,200 9,300 Mw/Mn - 3.25 3.56 3.18 3.10 3.20 1.90 1.91 2.04

◎[Table 2] Example 1 Example 2 Example 3 Example 4 Example 5 Comparative example 1 Comparative example 2 Comparative example 3 Photosensitive resin composition Alkali soluble resin Manufacturing example 1 parts by weight 8.09 Manufacturing example 2 parts by weight 8.09 Manufacturing example 3 parts by weight 8.09 Manufacturing example 4 parts by weight 8.09 Manufacturing Example 5 parts by weight 8.09 Manufacturing example 6 parts by weight 8.09 Manufacturing example 7 parts by weight 8.09 Manufacturing example 8 parts by weight 8.09 photopolymerizable compound DHPA parts by weight 2.25 2.25 2.25 2.25 2.25 2.25 2.25 2.25 Photopolymerization initiator 1-Hydroxycyclohexyl phenyl ketone parts by weight 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 solvent MMPGAC parts by weight 6.83 6.83 6.83 6.83 6.83 6.83 6.83 6.83

◎[Table 3] Example 6 Example 7 Example 8 Example 9 Example 10 Comparative example 4 Comparative Example 5 Comparative Example 6 Colored photosensitive resin composition Alkali soluble resin Manufacturing example 1 parts by weight 8.09 Manufacturing example 2 parts by weight 8.09 Manufacturing example 3 parts by weight 8.09 Manufacturing example 4 parts by weight 8.09 Manufacturing Example 5 parts by weight 8.09 Manufacturing example 6 parts by weight 8.09 Manufacturing example 7 parts by weight 8.09 Manufacturing example 8 parts by weight 8.09 colored material PR 254 parts by weight 0.77 0.77 0.77 0.77 0.77 0.77 0.77 0.77 Pigment Dispersant DISPERBYK-2000 parts by weight 0.31 0.31 0.31 0.31 0.31 0.31 0.31 0.31 photopolymerizable compound DHPA parts by weight 2.25 2.25 2.25 2.25 2.25 2.25 2.25 2.25 Photopolymerization initiator 1-Hydroxycyclohexyl phenyl ketone parts by weight 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 solvent MMPGAC parts by weight 18.8 18.8 18.8 18.8 18.8 18.8 18.8 18.8

◎[Table 4] Example 1 Example 2 Example 3 Example 4 Example 5 Comparative example 1 Comparative example 2 Comparative example 3 Evaluate Storage Stability Test at 23°C Viscosity increase rate % 2 10 2 8 -3 gelation gelation 13 Solvent resistance test-1 (hardening temperature 150°C) NMP - 〇 〇 〇 〇 〇 △ 〇 △ γ-BL - ◎ ◎ ◎ ◎ ◎ 〇 〇 〇 Solvent resistance test-2 (hardening temperature 230°C) NMP - 〇 〇 〇 〇 〇 △ 〇 〇 γ-BL - ◎ ◎ ◎ ◎ ◎ 〇 〇 ◎

◎[Table 5] Example 6 Example 7 Example 8 Example 9 Example 10 Comparative example 4 Comparative Example 5 Comparative example 6 Evaluate Storage Stability Test at 23°C Viscosity increase rate % 2 10 2 8 -3 gelation gelation 13 Solvent resistance test-1 (hardening temperature 150°C) NMP - 〇 〇 〇 〇 〇 △ 〇 △ γ-BL - ◎ ◎ ◎ ◎ ◎ 〇 〇 〇 Solvent resistance test-2 (hardening temperature 230°C) NMP - 〇 〇 〇 〇 〇 △ 〇 〇 γ-BL - ◎ ◎ ◎ ◎ ◎ 〇 〇 ◎

Hereinafter, components used in the production examples, examples, and comparative examples will be described. Monomer B1: Refer to Synthesis Example 1 Monomer B2: Refer to Synthesis Example 2 GMA: Glycidyl methacrylate (manufactured by NOF Corporation) Cyclomer M100: 3,4-epoxycyclohexylmethyl methacrylate ( Daicel Co., Ltd.) Monomer B3: 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-9-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Dec-8-yl ester mixture (trade name "E-DCPA", manufactured by Daicel Co., Ltd.) ST: styrene (manufactured by FUJIFILM Wako Pure Chemical Corporation) MMA: methyl methacrylate (manufactured by FUJIFILM Wako Pure Chemical Corporation Manufactured by the company) CHMI: N-cyclohexylmaleimide (manufactured by Nippon Shokubai Co., Ltd.) MMPGAC: Propylene glycol monomethyl ether acetate (manufactured by Daicel Co., Ltd.) PR 254: CI Pigment Red 254 (Tokyo Manufactured by Chemical Industry Co., Ltd.) DISPERBYK-2000: amine value 4 mgKOH/g, non-volatile content 40% (manufactured by BYK-Chemie Japan) DHPA: Dineopentylthritol hexaacrylate (trade name "KAYARAD DPHA"; Nippon Chemical Pharmaceutical Co., Ltd.) 1-Hydroxycyclohexyl phenyl ketone (manufactured by FUJIFILM Wako Pure Chemical Corporation) To sum up, the configuration and modifications of the present invention will be described below.

[1] A photosensitive resin composition comprising an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the alkali-soluble resin has a structure derived from an unsaturated carboxylic acid or its anhydride (a) A copolymer of unit (A) and structural unit (B) derived from the epoxy compound (b) shown in the aforementioned formula (b1) (wherein, R ^b1 represents a hydrogen atom or an alkyl group with 1 to 7 carbon atoms. R ^b2 represents a divalent hydrocarbon group which may contain a heteroatom. R ^b3 represents a divalent organic group having two or more epoxy groups).

[2] The photosensitive resin composition according to [1], wherein the unsaturated carboxylic acid or its anhydride (a) contains an α,β-unsaturated monocarboxylic acid selected from acrylic acid, methacrylic acid, and crotonic acid; α, β-unsaturated dicarboxylic acids such as itaconic acid, maleic acid, and fumaric acid; anhydrides of α, β-unsaturated monocarboxylic acids such as methacrylic anhydride; and maleic anhydride, At least one of the group consisting of anhydrides of α,β-unsaturated dicarboxylic acids such as itaconic anhydride.

[3] The photosensitive resin composition as described in [1] or [2], wherein the content of the structural unit (A) relative to all structural units of the copolymer is 2 to 50% by weight, 3 to 40% by weight, 5 to 25% by weight, or 10 to 20% by weight.

[4] The photosensitive resin composition according to any one of [1] to [3], wherein the epoxy group contained in the divalent organic group in R ^b3 is a ring other than an alicyclic epoxy group Oxygen.

[5] The photosensitive resin composition according to any one of [1] to [4], wherein the number of epoxy groups contained in the divalent organic group in R ^b3 is 2 to 10, 2 to 6 , or 2 to 4.

[6] The photosensitive resin composition as described in any one of [1] to [5], wherein the organic group in R ^b3 is a hydrocarbon group, a heterocyclic group, or two or more of them via a single bond Or the base formed by linking bases.

[7] The photosensitive resin composition as described in any one of [1] to [6], wherein the aforementioned epoxy compound (b) is a compound represented by the aforementioned formula (b2) (wherein, R ^b1 represents hydrogen Atoms or alkyl groups with 1 to 7 carbons. R ^b2 represents a divalent hydrocarbon group that may contain a heteroatom. R ^b4 may be identical or different and represents a divalent hydrocarbon group that has an epoxy group and may contain a heteroatom. nb1 represents an integer of 2 or more ).

[8] The photosensitive resin composition as described in any one of [1] to [7], wherein the aforementioned epoxy compound (b) is a compound represented by the aforementioned formula (b3) (wherein, R ^b1 represents hydrogen atom or an alkyl group with 1 to 7 carbons. ^{R b2} represents a divalent hydrocarbon group that may contain a heteroatom. R ^b5 identically or differently represents a hydrogen atom or an alkyl group with 1 to 6 carbon atoms. ^{R b6} identically or differently represents a single A bond or a divalent hydrocarbon group that may contain a heteroatom. nb2 and nb3 represent an integer of 0 or more, and the sum of nb2 and nb3 is 2 or more. The oxirane ring can have an alkyl group with 1 to 6 carbons. [ ] The two bases do not necessarily have to be arranged in the order shown in formula (b3)).

Shown compound, and aforementioned formula (b4) (wherein, R ^b1 represents the alkyl group of hydrogen atom or carbon number 1 to 7. R ^b2 represents the divalent hydrocarbon group that can contain heteroatom. R ^b7 represents hydrogen identically or differently atom or an alkyl group with 1 to 6 carbons. R ^b8 is a group bonded to the ring Z, and the same or different represents a single bond or a divalent hydrocarbon group that may contain a heteroatom. m represents an integer from 1 to 3. Ring Z represents an alicyclic hydrocarbon ring with 3 to 20 carbons. nb4 represents an integer of 2 or more. The oxirane ring may have an alkyl group with 1 to 6 carbons. Ring Z may have an alkyl group with 1 to 6 carbons as at least one of the group consisting of compounds represented by groups other than R ^b7 and R ^b8 ).

[9] The photosensitive resin composition as described in [8], wherein in the compound represented by the aforementioned formula (b3), R ^b6 is a linear or branched chain having 1 to 18 carbons or 3 to 8 carbons. Alkyl group, in the compound represented by the aforementioned formula (b4), the ring Z is a cycloalkane ring or a norbornane ring with 5 to 12 members.

[10] The photosensitive resin composition as described in [8] or [9], wherein the compound represented by the aforementioned formula (b3) is the compound represented by the aforementioned formula (b3-1) or the aforementioned formula (b3-2) Compounds shown.

[11] The photosensitive resin composition as described in any one of [8] to [10], wherein the compound represented by the aforementioned formula (b4) is a compound represented by the aforementioned formula (b4-1), the aforementioned formula ( A compound represented by b4-2), or a compound represented by the aforementioned formula (b4-3).

[12] The photosensitive resin composition according to any one of [1] to [11], wherein the content of the structural unit (B) is 10 to 98% by weight, 50 to 95% by weight, 70 to 92% by weight, or 80 to 90% by weight.

[13] The photosensitive resin composition according to any one of [1] to [12], which further contains a compound derived from at least one compound selected from the group consisting of the aforementioned (c1) to (c4). Structural unit (C): (c1) styrene which may be substituted by an alkyl group (c2) N-substituted maleimide (c3) N-vinyl compound (c4) the aforementioned formula (2) (wherein, R ¹¹ represents a hydrogen atom or an alkyl group with a carbon number of 1 to 7. R ¹² represents a monovalent hydrocarbon group that may contain a heteroatom. X represents a heteroatom) The unsaturated carboxylic acid derivative shown

[14] The photosensitive resin composition according to any one of [1] to [13], wherein the content of the structural unit (C) is 0 to 80% by weight, 1 to 60% by weight, 5 to 40% by weight, 10 to 30% by weight, or 15 to 25% by weight.

[15] The photosensitive resin composition as described in any one of [1] to [14], wherein the content of the structural unit (A) is 2 to 50% by weight relative to all the structural units of the copolymer, and the structural unit The content of (B) is 10 to 98% by weight, and the content of the structural unit (C) is 0 to 80% by weight.

[16] The photosensitive resin composition according to any one of [1] to [15], wherein the copolymer contains structural unit (A) and structural unit (B) but does not contain structural unit (C) In this case, the total amount of the structural unit (A) and the structural unit (B) is 90% by weight, 95% by weight or more, 99% by weight or more, or substantially 100% by weight with respect to all the structural units.

[17] The photosensitive resin composition as described in any one of [13] to [15], wherein when the aforementioned copolymer includes a structural unit (A), a structural unit (B) and a structural unit (C), the structure The total amount of units (A) to (C) is 90% by weight or more, 95% by weight or more, 99% by weight or more, or substantially 100% by weight with respect to all structural units.

[18] The photosensitive resin composition according to any one of [1] to [17], wherein the weight average molecular weight (Mw) of the copolymer is 6000 to 60000, 7000 to 30000, 8000 to 20000, or 8500 to 15000.

[19] The photosensitive resin composition according to any one of [1] to [18], wherein the molecular weight distribution (ratio of weight average molecular weight to number average molecular weight: Mw/Mn) of the copolymer is 6.0 or less, 1.5 to 6.0, 2.0 to 5.0, or 3.0 to 4.0.

[20] The photosensitive resin composition according to any one of [1] to [19], which further contains a colored material.

[21] The photosensitive resin composition according to [20], wherein the colored material is a pigment and/or a dye.

[22] The photosensitive resin composition according to any one of [20] or [21], wherein the content of the aforementioned colored material is 1 to 30% by weight or 3% by weight relative to the solid content of the photosensitive resin composition. to 15% by weight.

[23] The photosensitive resin composition according to any one of [1] to [22], wherein the photopolymerizable compound is selected from polyfunctional vinyl compounds, polyfunctional thiol compounds, and polyfunctional epoxy compounds. At least one of the group consisting of compounds.

[24] The photosensitive resin composition according to any one of [1] to [23], wherein the content of the photopolymerizable compound is 1 to 100 parts by weight relative to 100 parts by weight of the alkali-soluble resin, 5 to 60 parts by weight, or 10 to 40 parts by weight.

[25] The photosensitive resin composition according to any one of [20] to [24], wherein when the photosensitive resin composition contains a colored material, the content of the photopolymerizable compound is 100% of the colored material. The parts by weight are 10 to 800 parts by weight, 50 to 500 parts by weight, or 200 to 300 parts by weight.

[26] The photosensitive resin composition according to any one of [1] to [25], wherein the content of the alkali-soluble resin is 5 to 80% by weight, 10 to 70% by weight, 15 to 60% by weight, or 20 to 55% by weight.

[27] The photosensitive resin composition according to any one of [1] to [25], wherein when the photosensitive resin composition does not contain a coloring material, the content of the alkali-soluble resin is 15 to 75% by weight, 20 to 70% by weight, 25 to 60% by weight, or 30 to 55% by weight.

[28] The photosensitive resin composition according to any one of [20] to [25], wherein when the photosensitive resin composition contains a colored material, the content of the alkali-soluble resin is 5 to 70% by weight, 10 to 60% by weight, 15 to 50% by weight, or 20 to 40% by weight.

[29] The photosensitive resin composition according to any one of [1] to [28], wherein the content of the alkali-soluble resin is 30 to 95% by weight, 40 to 90% by weight, 50 to 85% by weight, or 60 to 80% by weight.

[30] The photosensitive resin composition according to any one of [1] to [28], wherein when the photosensitive resin composition does not contain a coloring material, the content of the alkali-soluble resin relative to the photosensitive resin composition The solid content is 40 to 90% by weight, 50 to 85% by weight, or 60 to 80% by weight.

[31] The photosensitive resin composition according to any one of [20] to [28], wherein when the photosensitive resin composition contains a colored material, the content of the alkali-soluble resin relative to the solid content of the photosensitive resin composition 40 to 90% by weight, 50 to 80% by weight, or 60 to 75% by weight of the material components.

[32] The photosensitive resin composition according to any one of [1] to [31], wherein the content of the photopolymerizable compound is 1 to 60% by weight, 2 to 40% by weight, 3 to 30% by weight, or 5 to 20% by weight.

[33] The photosensitive resin composition according to any one of [1] to [31], wherein when the photosensitive resin composition does not contain a coloring material, the content of the photopolymerizable compound is 3 to 40% by weight, 5 to 30% by weight, 8 to 25% by weight, or 10 to 20% by weight.

[34] The photosensitive resin composition according to any one of [20] to [31], wherein when the photosensitive resin composition contains a colored material, the content of the photopolymerizable compound is 2 to 30% by weight, 3 to 20% by weight, or 5 to 15% by weight.

[35] The photosensitive resin composition according to any one of [1] to [34], wherein the content of the photopolymerizable compound is 3 to 60% by weight relative to the solid content of the photosensitive resin composition, 5 to 50% by weight, 10 to 40% by weight, or 15 to 30% by weight.

[36] The photosensitive resin composition according to any one of [1] to [34], wherein when the photosensitive resin composition does not contain a coloring material, the content of the photopolymerizable compound relative to the photosensitive resin composition The solid content is 5 to 50% by weight, 10 to 40% by weight, 15 to 30% by weight, or 18 to 25% by weight.

[37] The photosensitive resin composition according to any one of [20] to [34], wherein when the photosensitive resin composition contains a colored material, the content of the photopolymerizable compound is The solid content is 5 to 40% by weight, 10 to 30% by weight, or 15 to 25% by weight.

[38] A cured product of the photosensitive resin composition according to any one of [1] to [37].

[39] A color filter, which is a hardened product as described in [38].

[40] A member for a display device or a display device comprising the color filter according to [39]. Industrial availability

According to the invention of the present invention, a photosensitive resin composition having excellent storage stability, excellent curing reactivity, and excellent solvent resistance of a cured product can be provided. In addition, a cured product of the photosensitive resin composition having the above characteristics, a color filter as the cured product, and a member for a display device or a display device including the above color filter can be provided.

There is no pattern in this case.

Claims (9)

A photosensitive resin composition comprising an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the alkali-soluble resin comprises a structural unit (A) derived from an unsaturated carboxylic acid or an anhydride thereof and a source A copolymer of structural units (B) derived from epoxy compounds represented by the following formula (b1), ◎[Chemical Formula 1]

(In the formula, R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. ^{R b2} represents a divalent hydrocarbon group which may contain a heteroatom. R ^b3 represents a divalent organic group having two or more epoxy groups). The photosensitive resin composition according to Claim 1, wherein the aforementioned epoxy compound is at least one selected from the group consisting of compounds represented by the following formula (b3) and compounds represented by the following formula (b4), ◎[Chemical Formula 2]

(wherein, R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. R ^b2 represents a divalent hydrocarbon group which may contain a heteroatom. R ^b5 identically or differently represents a hydrogen atom or an alkyl group having 1 to 6 carbons. R ^b6 identically or differently represents a single bond or a divalent hydrocarbon group that may contain a heteroatom. nb2 and nb3 each represent an integer of 0 or more, and the sum of nb2 and nb3 is 2 or more. The oxirane ring may have 1 to 6 carbon atoms The two groups in [ ] do not necessarily have to be arranged in the order shown in formula (b3)) ◎[Chemical formula 3]

(wherein, R ^b1 represents a hydrogen atom or an alkyl group having 1 to 7 carbons. R ^b2 represents a divalent hydrocarbon group which may contain a heteroatom. R ^b7 identically or differently represents a hydrogen atom or an alkyl group having 1 to 6 carbons. R ^b8 is a group bonded to the ring Z, and the same or different represents a single bond or a divalent hydrocarbon group that may contain a heteroatom. m represents an integer from 1 to 3. Ring Z represents an alicyclic formula with 3 to 20 carbon atoms Hydrocarbon ring. nb4 represents an integer of 2 or more. The oxirane ring may have an alkyl group having 1 to 6 carbons. Ring Z may have an alkyl group having 1 to 6 carbons as a group other than R ^b7 and R ^b8 ). The photosensitive resin composition according to claim 1 or 2, which further comprises a structural unit (C) derived from at least one compound selected from the group consisting of the following (c1) to (c4): (c1) may Alkyl-substituted styrene (c2) N-substituted maleimide (c3) N-vinyl compound (c4) Unsaturated carboxylic acid derivative represented by the following formula (2) ◎[Chemical formula 4 ]

(In the formula, R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. ^{R 12} represents a monovalent hydrocarbon group that may contain a heteroatom. X represents a heteroatom). Such as the photosensitive resin composition of claim 3, wherein the content of the structural unit (A) relative to all structural units of the copolymer is 2 to 50% by weight, and the content of the structural unit (B) is 10 to 98% by weight, and the structure The content of the unit (C) is 0 to 80% by weight. The photosensitive resin composition according to any one of Claims 1 to 4, which further contains a colored material. The photosensitive resin composition according to claim 5, wherein the aforementioned colored material is a pigment and/or a dye. A cured product, which is a cured product of the photosensitive resin composition according to any one of claims 1 to 6. A color filter, which is the hardened product as claimed in item 7. A member for a display device or a display device, comprising the color filter according to Claim 8.