TW202024792A - Photosensitive resin composition, method for producing a patterned cured film, and cured film - Google Patents

Abstract

The present invention relates to a photosensitive resin composition, a method for producing a patterned cured film, and a cured film. An object of the present invention is to provide a photosensitiveresin composition excellent in patterning characteristics, a method for producing a cured film, and a cured product. The solution of the present invention is a photosensitive resin composition comprising an alkali-soluble resin (A), a cross-linking agent (B), and a photopolymerization initiator (C). The aforementioned crosslinking agent (B) contains a monofunctional (meth) acrylic monomer (B1), and the monofunctional (meth) acrylic monomer (B1) contains a biphenyl skeleton which may have a substituent or a terphenyl skeleton which may have a substituent.

Description

Photosensitive resin composition, method for producing patterned cured film, and cured film

The present invention relates to a photosensitive resin composition, a method for producing a patterned cured film, and a cured film.

Since the photolithography method can be used to easily form a patterned cured film of a specific shape, a photosensitive resin composition containing an alkali-soluble resin can be used, for example, in display devices such as liquid crystal displays, semiconductor devices, and other fields. widely used.

In the photosensitive composition, the photopolymerization initiator contained as a part of its components generates radicals by exposure. This radical polymerizes the polymerizable compound contained in the photosensitive composition, and the photosensitive composition is cured. In addition, in the photosensitive resin composition, the radicals generated by the photopolymerization initiator are used to polymerize the polymerizable compound, and on the other hand, the adhesiveness of the photosensitive resin composition to the substrate and the photosensitive resin composition are improved. For the purpose of strength after curing, a crosslinking agent is formulated. This crosslinking agent component has conventionally used polyfunctional monomers having ethylenically unsaturated groups for the purpose described above, especially dipentaerythritol penta- and hexaacrylates and other pentafunctional or higher (methyl ) Acrylic monomers.

In recent years, from the viewpoint of improving productivity, there is an urgent need for a photosensitive resin composition with high sensitivity that can be patterned with a low exposure amount. On the other hand, in the case of a cured film patterned in a complicated shape, a film made of a photosensitive resin composition as an exposure object may be a trigger for curing the photosensitive resin composition The exposure light source does not penetrate more areas. At this time, in the case of the photosensitive resin composition of the above-mentioned composition, it is easy to cause the defect that the part is not sufficiently cured after exposure. In addition, the state of applying the photosensitive resin composition to a cured film to obtain a thicker film of several tens of μm or more has also been extensively reviewed. However, in the case of forming such a thick cured film, the following problems are likely to occur: the exposure light source does not sufficiently reach the far side of the film formed of the photosensitive resin composition that is far from the light source. That is, usually, in the vicinity of the contact surface between the substrate and the photosensitive resin layer, a portion where the curing is insufficient is formed in the cured film. Moreover, in the aspect in which the photosensitive resin composition contains a coloring agent, the problem of the formation of an insufficiently cured portion in the cured film due to the absorption of the exposure light source by the coloring agent is significant.

Patent Document 1 proposes a photosensitive resin composition with a specific composition for the purpose of curing a region in the photosensitive resin composition that cannot be directly reached by the activation energy even at a low exposure amount. In Patent Document 1, specifically, it is proposed to contain an aromatic group-containing monofunctional (meth)acrylic monomer (A), other than components (A), having an average of at least one polymerizable carbon-carbon in the molecule A curable composition of a double bond compound (B) and (C) a photopolymerization initiator. As the (A) component, specifically, o-phenylphenoxyethyl acrylate or the like is used, and as the (B) component, specifically, an acrylate-based polymer or the like is used. Prior art literature Patent literature

Patent Document 1: JP 2014-51618

Problems to be solved by the invention

However, even a curable composition as described in Patent Document 1 may not be able to adequately cope with a situation where the problem of insufficient curing is formed in the cured film. In addition, even if the formation of insufficiently cured parts can be suppressed, in this case, although the rectangularity (taperity) of the formed line pattern can be improved to a certain extent, on the other hand, regarding the linear travel of the line pattern ( Reproducibility) or resolution, further improvement is desired. Therefore, a photosensitive resin composition with more excellent sensitivity is required.

The present invention was completed in view of the above-mentioned problems of the prior art. The object of the present invention is to provide a photosensitive resin composition with high sensitivity and excellent patterning characteristics such as line width stability, resolution, and rectangularity. The manufacturing method of the patterned cured film of this photosensitive resin composition and the cured film are described. Means to solve the problem

The inventors of the present invention have found that the photosensitive resin composition has high sensitivity by mixing the photosensitive resin composition with a monofunctional (meth)acrylate compound containing a specific structure. For example, even when the cured film is formed into a thick film Or the active energy rays that form the cured film of complex shapes can not directly reach the parts, which can also be cured well. The rectangularity (taperity) of the pattern is good, and the resolution is high and the linear travel of the pattern (reproducibility) is also good. , Can improve the patterning characteristics, and complete the present invention. That is, the present invention is as follows.

The first aspect of the present invention is a photosensitive resin composition comprising an alkali-soluble resin (A), a crosslinking agent (B), and a photopolymerization initiator (C), wherein: The aforementioned crosslinking agent (B) contains a monofunctional (meth)acrylate monomer (B1), and the aforementioned monofunctional (meth)acrylate monomer (B1) contains a biphenyl skeleton which may have a substituent or may be substituted The terphenyl skeleton of the base.

The second aspect of the present invention is a method for manufacturing a patterned cured film, which includes the steps of: coating the photosensitive resin composition of the first aspect on a substrate to form a photosensitive resin layer; The step of exposing the aforementioned photosensitive resin layer in a position-selective manner; and the step of developing the exposed photosensitive resin layer with a developing solution.

The third aspect of the present invention is a cured film obtained by curing the photosensitive resin composition of the first aspect. Effect of invention

According to the present invention, it is possible to provide a photosensitive resin composition having high sensitivity and excellent patterning characteristics such as line width stability, resolution and rectangularity, and a patterned cured film using the photosensitive resin composition The manufacturing method and cured film. Form of invention

Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments at all, and can be implemented with appropriate modifications within the scope of the object of the present invention.

≪Photosensitive resin composition≫ The photosensitive resin composition contains alkali-soluble resin (A), crosslinking agent (B), and photoinitiator (C). In the photosensitive resin composition, as the crosslinking agent (B), a monofunctional (meth)acrylate monomer (B1) is contained, and the monofunctional (meth)acrylate monomer (B1) contains an optionally substituted group The biphenyl skeleton or the terphenyl skeleton which may have substituents. The components contained in the photosensitive resin composition are explained in order below.

＜Alkali-soluble resin (A)＞ The photosensitive resin composition contains alkali-soluble resin (A). Here, in the present specification, the (A) alkali-soluble resin refers to a resin having a functional group (for example, a phenolic hydroxyl group, a carboxyl group, a sulfonic acid group, etc.) that makes it alkali-soluble in the molecule. The type of alkali-soluble resin (A) is not particularly limited, and various alkali-soluble resins conventionally formulated in photosensitive resin compositions can be used. Hereinafter, as a preferable specific example of the alkali-soluble resin (A), the resin (A1) having the Cardo structure, the acrylic resin (A2), and the novolac resin (A3) will be described.

[Resin with Cardo structure (A1)] In the photosensitive resin composition, as the alkali-soluble resin (A), a resin (A1) having a Cardo structure (hereinafter, also referred to as "Cardo resin (A1)") may be contained.

As the Cardo resin (A1), a resin having a Cardo skeleton in its structure and having desired alkali solubility can be used. The so-called Cardo skeleton refers to a skeleton in which the second cyclic structure and the third cyclic structure are bonded to one ring carbon atom constituting the first cyclic structure. In addition, the second cyclic structure and the third cyclic structure may be the same structure or different structures. As a representative example of the Cardo skeleton, a skeleton in which two aromatic rings (for example, a benzene ring) are bonded to the carbon atom at the 9th position of the chrysanthemum ring is mentioned.

(式(a-1)中，X^a 表示下述式(a-2)表示的基團。m1表示0以上且20以下的整數)。There are no particular limitations on the Cardo resin (A1), and conventionally known resins can be used. Among them, a resin represented by the following formula (a-1) is preferred.

(In formula (a-1), X ^a represents ^{a group} represented by the following formula (a-2). m1 represents an integer of 0 or more and 20 or less).

(式(a-2)中，R^a1 各自獨立地表示氫原子、碳原子數為1以上且6以下的烴基、或鹵素原子，R^a2 各自獨立地表示氫原子或甲基，R^a3 各自獨立地表示直鏈或支鏈的伸烷基，m2表示0或1，W^a 表示下述式(a-3)表示的基團)。

(In formula (a-2), R ^a1 each independently represents a hydrogen atom, a hydrocarbon group having from 1 to 6 carbon atoms, or a halogen atom, R ^a2 each independently represents a hydrogen atom or a methyl group, and R ^a3 each independently Ground represents a linear or branched alkylene group, m2 represents 0 or 1, and Wa represents ^{a group} represented by the following formula (a-3)).

(式(a-3)中的環A表示可與芳香族環縮合且可具有取代基的脂肪族環。脂肪族環可為脂肪族烴環，也可為脂肪族雜環)。

(The ring A in the formula (a-3) represents an aliphatic ring that may be condensed with an aromatic ring and may have a substituent. The aliphatic ring may be an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring).

In formula (a-2), ^{Ra3 is} preferably an alkylene having 1 or more and 20 or less carbon atoms, more preferably an alkylene having 1 or more and 10 or less carbon atoms, and particularly preferably carbon The alkylene group having 1 to 6 atoms is most preferably ethane-1,2-diyl, propane-1,2-diyl, and propane-1,3-diyl.

Regarding the ring A in the formula (a-3), examples of the aliphatic ring include monocycloalkanes, bicycloalkanes, tricycloalkanes, and tetracycloalkanes. Specifically, monocyclic alkanes such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane can be mentioned. The aromatic ring that can be condensed with the aliphatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and is preferably an aromatic hydrocarbon ring. Specifically, a benzene ring and a naphthalene ring are preferable.

As a preferable example of the divalent group represented by formula (a-3), the following groups can be mentioned.

The divalent group X ^a in the formula (a-1) can be introduced into (A1) by reacting the tetracarboxylic dianhydride that provides the residue Z ^a with the diol compound represented by the following formula (a-2a) Cardo resin.

In the formula (a-2a), R ^a1 , R ^a2 , R ^a3 , and m2 are the same as described for the formula (a-2). Regarding the ring A in the formula (a-2a), it is the same as described for the formula (a-3).

The diol compound represented by formula (a-2a) can be produced by the following method, for example. First, if necessary, according to a conventional method, after replacing the hydrogen atom in the phenolic hydroxyl group of the diol compound represented by the following formula (a-2b) with a group represented by -R ^a3 -OH, epichlorohydrin is used The etc. are glycidylated to obtain an epoxy compound represented by the following formula (a-2c).

Next, by reacting the epoxy compound represented by the formula (a-2c) with acrylic acid or methacrylic acid, the diol compound represented by the formula (a-2a) is obtained. In formula (a-2b) and formula (a-2c), R ^a1 , R ^a3 , and m2 are the same as described for formula (a-2). Regarding the ring A system in the formula (a-2b) and the formula (a-2c), it is the same as the description for the formula (a-3).

In addition, the method for producing the diol compound represented by formula (a-2a) is not limited to the above-mentioned method.

As a preferable example of the diol compound represented by Formula (a-2b), the following diol compounds can be mentioned.

In the above formula (a-1), ^Ra0 is a hydrogen atom or ^a group represented by -CO-Y ^a -COOH. Here, Y ^a represents the residue after removing the acid anhydride group (-CO-O-CO-) from the dicarboxylic anhydride. Examples of dicarboxylic acid anhydrides include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl endomethylene tetrahydro Phthalic anhydride, Chlorendic Anhydride, methyltetrahydrophthalic anhydride, glutaric anhydride, etc.

Further, in the above formula ^(a-1), Z a represents a residue obtained by removing two acid anhydride groups in the tetracarboxylic dianhydride. Examples of tetracarboxylic dianhydride include tetracarboxylic dianhydride, pyromellitic dianhydride, benzophenone tetracarboxylic dianhydride, and biphenyl tetracarboxylic dianhydride represented by the following formula (a-4) , Diphenyl ether tetracarboxylic dianhydride, etc. In addition, in the above formula (a-1), m1 represents an integer of 0 or more and 20 or less.

(式(a-4)中，R^a4 、R^a5 、及R^a6 各自獨立地表示選自由氫原子、碳原子數為1以上且10以下的烷基及氟原子所組成的群組中的1種，m3表示0以上且12以下的整數)。

(In formula (a-4), R ^a4 , R ^a5 , and R ^a6 each independently represent 1 selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms and a fluorine atom Species, m3 represents an integer from 0 to 12).

The alkyl group that can be selected as R ^a4 in the formula (a-4) is an alkyl group having 1 to 10 carbon atoms. By setting the number of carbon atoms of the alkyl group to the above range, the heat resistance of the resulting carboxylic acid ester can be further improved. When R ^a4 is an alkyl group, the number of carbon atoms is preferably 1 or more and 6 or less, more preferably 1 or more and 5 or less, and even more preferably 1 or more and 4 or less from the viewpoint of easily obtaining a Cardo resin having excellent heat resistance. Especially preferably, it is 1 or more and 3 or less. When R ^a4 is an alkyl group, the alkyl group may be linear or branched.

Formula (a4) in R ^a4, easily obtained from the viewpoint of excellent heat resistance of the resin Cardo, more preferably are each independently 1 or more and 10 or less a hydrogen atom or an alkyl group carbon atoms. R ^a4 in the formula (a-4) is more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group or an isopropyl group, and particularly preferably a hydrogen atom or a methyl group. From the viewpoint of easy preparation of high-purity tetracarboxylic dianhydride, a plurality of ^Ra4 in the formula (a-4) are preferably the same group.

M3 in formula (a-4) represents an integer of 0 or more and 12 or less. By setting the value of m3 to 12 or less, the tetracarboxylic dianhydride can be easily purified. From the viewpoint of easy purification of tetracarboxylic dianhydride, the upper limit of m3 is preferably 5, more preferably 3. From the viewpoint of the chemical stability of tetracarboxylic dianhydride, the lower limit of m3 is preferably 1, and more preferably 2. In formula (a-4), m3 is particularly preferably 2 or 3.

The alkyl group having 1 or more and 10 or less carbon atoms that can be selected as ^Ra5 and ^Ra6 in the formula (a-4) is the same as the alkyl group having 1 or more and 10 or less carbon atoms that can be selected as R ^a4 . From the standpoint of easy purification of tetracarboxylic dianhydride, R ^a5 and R ^{a6 are} preferably hydrogen atoms, or carbon atoms of 1 or more and 10 or less (preferably 1 or more and 6 or less, more preferably 1 or more and 5 Below, more preferably 1 or more and 4 or less, particularly preferably 1 or more and 3 or less) alkyl group, particularly preferably a hydrogen atom or a methyl group.

Examples of the tetracarboxylic dianhydride represented by the formula (a-4) include norbornane-2-spiro-α-cyclopentanone-α'-spiro-2"-norbornane-5,5", 6,6"-tetracarboxylic dianhydride (alias "norbornane-2-spiro-2'-cyclopentanone-5'-spiro-2"-norbornane-5,5",6,6"- Tetracarboxylic dianhydride”), methylnorbornane-2-spiro-α-cyclopentanone-α'-spiro-2”-(methylnorbornane)-5,5”,6,6”-tetra Formic acid dianhydride, norbornane-2-spiro-α-cyclohexanone-α'-spiro-2"-norbornane-5,5",6,6"-tetracarboxylic dianhydride (alias "norbornane" Alkyl-2-spiro-2'-cyclohexanone-6'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic dianhydride”), methylnorbornane-2- Spiro-α-cyclohexanone-α'-spiro-2”-(methylnorbornane)-5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-ring Acetone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclobutanone-α'-spiro-2” -Norbornane-5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cycloheptanone-α'-spiro-2”-norbornane-5,5” ,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclooctanone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic acid Anhydride, norbornane-2-spiro-α-cyclononanone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro -α-Cyclodecanone (Decanone)-α'-Spiro-2”-Norbornane-5,5”,6,6”-Tetracarboxylic dianhydride, Norbornane-2-Spiro-α-Cycloundecane Alkanone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclododecanone-α'-spiro -2”-Norbornane-5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclotridecylone-α'-spiro-2”-norbornane -5,5”,6,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclotetradecylone-α'-spiro-2”-norbornane-5,5”,6 ,6”-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclopentadecanone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic acid Anhydride, norbornane-2-spiro-α-(methylcyclopentanone)-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic dianhydride, norbornane -2-Spiro-α-(methylcyclohexanone)-α'-spiro-2"-norbornane-5,5",6,6"-tetracarboxylic dianhydride, etc.

The weight average molecular weight of the Cardo resin (A1) is preferably 1,000 or more and 40,000 or less, more preferably 2,000 or more and 30,000 or less. By setting it as the above-mentioned range, good developability can be obtained, and sufficient heat resistance and film strength can be obtained at the same time.

[Acrylic resin (A2)] As the alkali-soluble resin (A), an acrylic resin (A2) can also be preferably used. When the acrylic resin (A2) is used, various characteristics of the photosensitive resin composition can be easily adjusted by appropriately adjusting the type of monomer, the ratio of structural units, and the like.

As the acrylic resin (A2), a resin containing a structural unit derived from (meth)acrylic acid and/or a structural unit derived from other monomers such as (meth)acrylate can be used. (Meth)acrylic acid is acrylic acid or methacrylic acid. The (meth)acrylate is a compound represented by the following formula (a-5), and is not particularly limited as long as it does not interfere with the purpose of the present invention.

In the above formula (a-5), R ^a7 is a hydrogen atom or a methyl group, and R ^a8 is a monovalent organic group. This organic group may contain a bond or substituent other than a hydrocarbon group such as a hetero atom in the organic group. In addition, the organic group may be any of linear, branched, and cyclic.

As the substituent other than the organic group for R ^a8 in the hydrocarbon group defined as long as not impairing the effect of the present invention is not particularly limited, and may include a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a cyano group, an isocyano group, Cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, silyl group, silanol group, alkoxy group, alkoxycarbonyl group, aminomethanyl group, thioaminomethanyl group , Nitro group, nitroso group, carboxyl group, carboxylate/ester group (carboxylate group), acyl group, oxo group, sulfinyl group, sulfo group, sulfonato group (sulfonato group), phosphino group (phosphino group), Phosphinyl group, phosphinyl group, phosphonato group, hydroxyimino group, alkyl ether group, alkyl sulfide group, aryl ether group, aryl sulfide group, amine group (- NH ₂ , -NHR, -NRR': R and R'each independently represent a hydrocarbon group) and the like. The hydrogen atom contained in the above substituent may be substituted by a hydrocarbon group. In addition, the hydrocarbon group contained in the substituent may be any of linear, branched, and cyclic.

R ^{a8 is} preferably an alkyl group, an aryl group, an aralkyl group, or a heterocyclic group, and these groups may be substituted with a halogen atom, a hydroxyl group, an alkyl group, or a heterocyclic group. In addition, when these groups contain an alkylene moiety, the alkylene moiety may be interrupted by an ether bond, a thioether bond, or an ester bond.

When the alkyl group is linear or branched, the number of carbon atoms is preferably 1 or more and 20 or less, more preferably 1 or more and 15 or less, and particularly preferably 1 or more and 10 or less. Examples of preferred alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec Pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, n-decyl, isodecyl, etc.

When the alkyl group is an alicyclic group or a group containing an alicyclic group, preferred alicyclic groups included in the alkyl group include monocyclic groups such as cyclopentyl and cyclohexyl. Alicyclic groups or polycyclic alicyclic groups such as adamantyl, norbornyl, isobornyl, tricyclononyl, tricyclodecyl, and tetracyclododecyl.

The compound represented by the formula (a-5) is preferably an epoxy group-containing unsaturated compound having an epoxy group in ^Ra8 . Preferred examples of the epoxy group-containing unsaturated compound represented by the formula (a-5) include glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, (methyl) ) Epoxyalkyl (meth)acrylates such as 3,4-epoxybutyl acrylate, 6,7-epoxyheptyl (meth)acrylate, etc.; α-ethyl glycidyl acrylate, α-normal Alpha-alkyl acrylates such as glycidyl acrylate, glycidyl α-n-butyl acrylate, 6,7-epoxyheptyl α-ethyl acrylate, etc.; etc. Among these, from the viewpoints of copolymerization reactivity, the strength of the cured resin, etc., glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, and (meth)acrylic acid 6 are preferred. ,7-Epoxyheptyl ester. These epoxy group-containing unsaturated compounds may be used alone or in combination of two or more kinds.

In addition, the acrylic resin (A2) may be a resin obtained by polymerizing a monomer other than (meth)acrylate. Examples of such monomers include (meth)acrylamides, unsaturated carboxylic acids, allyl compounds, vinyl ethers, vinyl esters, and styrenes. These monomers can be used individually or in combination of 2 or more types.

Examples of (meth)acrylamides include (meth)acrylamide, N-alkyl(meth)acrylamide, N-aryl(meth)acrylamide, N,N-di Alkyl(meth)acrylamide, N,N-aryl(meth)acrylamide, N-methyl-N-phenyl(meth)acrylamide, N-hydroxyethyl-N-methyl Group (meth)acrylamide and the like.

Examples of unsaturated carboxylic acids include monocarboxylic acids such as crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid; anhydrides of these dicarboxylic acids; and the like.

Examples of allyl compounds include allyl acetate, allyl hexanoate, allyl octoate, allyl laurate, allyl palmitate, allyl stearate, allyl benzoate, Allyl esters such as allyl acetate and allyl lactate; allyloxyethanol; etc.

Examples of vinyl ethers include hexyl vinyl ether, octyl vinyl ether, decyl vinyl ether, ethylhexyl vinyl ether, methoxyethyl vinyl ether, and ethoxyethyl vinyl ether. , Chloroethyl vinyl ether, 1-methyl-2,2-dimethylpropyl vinyl ether, 2-ethylbutyl vinyl ether, hydroxyethyl vinyl ether, diethylene glycol vinyl ether , Dimethylaminoethyl vinyl ether, diethylaminoethyl vinyl ether, butylaminoethyl vinyl ether, benzyl vinyl ether, tetrahydrofurfuryl vinyl ether and other alkyl ethylene Base ether; vinyl phenyl ether, vinyl tolyl ether, vinyl chlorophenyl ether, vinyl-2,4-dichlorophenyl ether, vinyl naphthyl ether, vinyl anthracenyl ether and other vinyl aromatics Base ether; etc.

Examples of vinyl esters include vinyl butyrate, vinyl isobutyrate, trimethyl vinyl acetate, diethyl vinyl acetate, vinyl valerate, vinyl caproate, and vinyl chloroacetate. Ester, vinyl dichloroacetate, vinyl methoxyacetate, vinyl butoxyacetate, phenyl vinyl acetate, vinyl acetate, vinyl lactate, vinyl β-phenylbutyrate, vinyl benzoate Ester, vinyl salicylate, vinyl chlorobenzoate, vinyl tetrachlorobenzoate, vinyl naphthoate, etc.

Examples of styrenes include styrene; methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, isopropyl styrene, butyl styrene, Among hexyl styrene, cyclohexyl styrene, decyl styrene, benzyl styrene, chloromethyl styrene, trifluoromethyl styrene, ethoxy methyl styrene, acetoxy methyl styrene, etc. Alkylstyrene; Alkoxystyrene such as methoxystyrene, 4-methoxy-3-methylstyrene, dimethoxystyrene, etc.; Chlorostyrene, dichlorostyrene, trichlorostyrene , Tetrachlorostyrene, pentachlorostyrene, bromostyrene, dibromostyrene, iodostyrene, fluorostyrene, trifluorostyrene, 2-bromo-4-trifluoromethylstyrene, 4-fluoro- Halogenated styrenes such as 3-trifluoromethylstyrene; etc.

(A3) The amount of structural units derived from (meth)acrylic acid and the amount of structural units derived from other monomers in the acrylic resin are not particularly limited within a range that does not hinder the purpose of the present invention. (A3) The amount of structural units derived from (meth)acrylic acid in the acrylic resin is preferably 5% by mass or more and 50% by mass or less, more preferably 10% by mass or more relative to the mass of the acrylic resin And 30% by mass or less.

The weight average molecular weight of the acrylic resin (A2) is preferably 2,000 or more and 50,000 or less, more preferably 5,000 or more and 30,000 or less. By setting it as the said range, there exists a tendency for the balance of the film forming ability of a photosensitive resin composition and the developability after exposure to be easily acquired.

[Novolac (Novolac) resin (A3)] The alkali-soluble resin (A) may include Novolac resin (A3). When the alkali-soluble resin (A) contains Novolac resin (A3), it is easy to form a cured film with good heat resistance that is not easily deformed by heating.

As the Novolac resin (A3), various Novolac resins conventionally compounded in photosensitive resin compositions can be used. The Novolac resin (A3) is preferably a Novolac resin obtained by addition condensation of an aromatic compound having a phenolic hydroxyl group (hereinafter referred to as "phenols") and aldehydes under an acid catalyst.

(Phenols) Examples of phenols that can be used in the production of Novolac resin (A3) include phenol; cresols such as o-cresol, m-cresol, and p-cresol; 2,3-xylenol, 2,4-dimethylphenol Phenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol and other xylenols; o-ethylphenol, m-ethylphenol, Ethyl phenols such as p-ethylphenol; 2-isopropylphenol, 3-isopropylphenol, 4-isopropylphenol, o-butylphenol, m-butylphenol, p-butylphenol, and p-tert Alkylphenols such as butylphenol; trialkylphenols such as 2,3,5-trimethylphenol and 3,4,5-trimethylphenol; resorcinol, catechol, Polyphenols such as hydroquinone, hydroquinone monomethyl ether, pyrogallol, and phloroglucinol; alkyl resorcinol, alkyl catechol, and alkyl hydroquinone Alkyl polyphenols such as phenols (the number of carbon atoms in all alkyl groups is 1 to 4); α-naphthol; β-naphthol; hydroxydiphenyl; and bisphenol A, etc. These phenols may be used individually or in combination of 2 or more types.

Among these phenols, m-cresol and p-cresol are preferred, and the combined use of m-cresol and p-cresol is more preferred. In this case, by adjusting the blending ratio of the two, it is possible to adjust various characteristics such as heat resistance of the cured film formed using the photosensitive resin composition. The blending ratio of m-cresol and p-cresol is not particularly limited, but the molar ratio of m-cresol/p-cresol is preferably 3/7 or more and 8/2 or less. By using m-cresol and p-cresol in a ratio in this range, it is easy to obtain a photosensitive resin composition capable of forming a cured film having excellent heat resistance.

In addition, a Novolac resin produced by using metacresol and 2,3,5-trimethylphenol in combination is also preferable. When such a Novolac resin is used, it is particularly easy to obtain a photosensitive resin composition that can form a cured film that is less likely to flow excessively due to heating during post-baking. The blending ratio of m-cresol and 2,3,5-trimethylphenol is not particularly limited, and the molar ratio of m-cresol/2,3,5-trimethylphenol is preferably 70/30 or more and 95 Below /5.

(Aldehydes) Examples of aldehydes that can be used when producing Novolac resin (A3) include formaldehyde, paraformaldehyde, furfural, benzaldehyde, nitrobenzaldehyde, and acetaldehyde. These aldehydes may be used alone or in combination of two or more kinds.

(Acid catalyst) Examples of acid catalysts that can be used in the production of Novolac resin (A3) include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and phosphorous acid; formic acid, oxalic acid, acetic acid, diethyl sulfate, and p-toluenesulfonic acid And other organic acids; and metal salts such as zinc acetate. These acid catalysts may be used alone or in combination of two or more kinds.

(Molecular weight) Regarding the weight average molecular weight (Mw; hereafter, also referred to as "weight average molecular weight") in terms of polystyrene of Novolac resin (A3), the resistance of the cured film formed from the photosensitive resin composition to flow due to heating From a viewpoint, as the lower limit value, it is preferably 2000, more preferably 5000, particularly preferably 10000, still more preferably 15000, most preferably 20000, and as the upper limit value, it is preferably 50000, more preferably 45000, and more The best is 40,000, and the best is 35,000.

As the Novolac resin (A3), at least two types of resins having different weight average molecular weights in terms of polystyrene can be used in combination. By combining resins with different weight average molecular weights, the developability of the photosensitive resin composition and the heat resistance of the cured film formed using the photosensitive resin composition can be balanced.

The content of the alkali-soluble resin (A) is preferably 30% by mass or more and 90% by mass or less, and more preferably 40% by mass or more and 80% by mass or less with respect to the mass of the entire solid content of the photosensitive resin composition. By setting it as the said range, it becomes easy to obtain the photosensitive resin composition excellent in developability.

＜(B) Crosslinking agent＞ (Monofunctional (meth)acrylic monomer (B1)) The photosensitive resin composition contains a crosslinking agent (B), and as the crosslinking agent (B), a monofunctional (meth)acrylic monomer (B1) and the monofunctional (meth)acrylic monomer ( B1) It contains a biphenyl skeleton which may have a substituent or a terphenyl skeleton which may have a substituent. In addition, the "(meth)acrylic monomer" refers to an acrylic and/or methacrylic monomer that can be derived from (meth)acrylic acid.

As a specific example of the monofunctional (meth)acrylic monomer (B1), the compound of the following formula can be mentioned.

In the above formula, R ^x is a hydrogen atom or a methyl group. BP is a biphenyl group which may have substituents, and the specific skeleton is 1,1'-biphenyl-4-yl, 1,1'-biphenyl-3-yl, or 1,1'-biphenyl-2- The group is preferably 1,1'-biphenyl-2-yl or 1,1'-biphenyl-4-yl. TP is a terphenyl which may have a substituent, and a specific skeleton is any of the groups represented by the following formula.

The monofunctional (meth)acrylic monomer (B1) is particularly preferably a monofunctional (meth)acrylic monomer (B1a) containing a biphenyl skeleton that may have a substituent.

In the monofunctional (meth)acrylic monomer (B1), the substituents that the biphenyl skeleton and the terphenyl skeleton may have include alkyl groups having 1 to 12 carbon atoms, and 1 or more carbon atoms And an alkoxy group having 12 or less carbon atoms, an alkoxycarbonyl group having 2 or more and 12 or less carbon atoms, an acyl group having 1 or more and 12 or less carbon atoms, an alkoxy group having 1 or more and 12 or less carbon atoms, Hydroxyl group, halogen atom, cyano group or nitro group.

(式(B1-1)中，R^b1 為氫原子或甲基，R^b2 為碳原子數為1以上且4以下的伸烷基，BP為可具有取代基的聯苯基，t1為0以上且10以下的整數，t1為0時，X^b1 為-O-或-NH-，t1為1以上且10以下的整數時，X^b1 為選自由單鍵、-O-、 -NH-、-O-CO-*、-NH-CO-*、-O-CO-O-、及-NH-CO-O-*所組成之群組中的連接基團，連接基團中之非對稱的連接基團中的標有*的鍵結鍵為與BP鍵結的鍵結鍵)。As the monofunctional (meth)acrylic monomer (B1a), a compound represented by the following formula (B1-1) is preferably used.

(In formula (B1-1), R ^b1 is a hydrogen atom or a methyl group, R ^b2 is an alkylene group having 1 or more and 4 or less carbon atoms, BP is an optionally substituted biphenyl group, and t1 is 0 or more And an integer of 10 or less, when t1 is 0, X ^b1 is -O- or -NH-, and when t1 is an integer of 1 to 10, X ^b1 is selected from a single bond, -O-, -NH-,- The linking group in the group consisting of O-CO-*, -NH-CO-*, -O-CO-O-, and -NH-CO-O-*, the asymmetric connection in the linking group The bonding bond marked with * in the group is the bonding bond with BP).

The substituents that the biphenyl group may have are the same as those exemplified above regarding the substituents that the biphenyl skeleton and the terphenyl skeleton may have.

The number of carbon atoms of the alkylene group as R ^b2 is 1 or more and 4 or less, preferably 2 or 3. Examples of the alkylene group include methylene group, ethylene group, 1,3-trimethylene group, 1,2-propylene group, and butane-1,2- Diyl and other linear or branched alkylene groups. Among these, ethylene group, 1,3-propylene group, and 1,2-propylene group are preferred.

t1 is preferably 0, 1, or 2.

There are no particular limitations on the compound represented by the above formula (B1-1). As preferable examples of the compound represented by formula (B1-1), the following compounds may be mentioned.

The compound represented by the above formula (B1-1) is preferably B1-1-a, B1-1-c, B1-1-e, B1-1-f, B1-1-i, B1-1-m , Particularly preferred are B1-1-a and B1-1-c.

(Multifunctional (meth)acrylic monomer (B2)) The photosensitive resin composition may contain a crosslinking agent (B) other than the above-mentioned monofunctional (meth)acrylic monomer (B1). As the crosslinking agent (B) other than the monofunctional (meth)acrylic monomer (B1), for example, a polyfunctional (meth)acrylic monomer (B2) can be given.

(式(B2-1)中，R^b3 為氫原子、或碳原子數為1以上且4以下的烷基，R^b4 為將多元醇R^b5 (OH)_m 之m個羥基中t2個羥基供予式(B2-1)中之酯鍵而得的t2價的殘基，m及t2各自獨立地為2以上且20以下的整數，m為t2以上)。As the polyfunctional (meth)acrylic monomer (B2), preferably, a polyfunctional (meth)acrylate represented by the following formula (B2-1) is used.

(In formula (B2-1), R ^b3 is a hydrogen atom, or an alkyl group having 1 or more and 4 or less carbon atoms, and R ^b4 is a polyol R ^b5 (OH) _m of m hydroxyl groups for t2 hydroxyl groups. For the t2-valent residue obtained by the ester bond in the formula (B2-1), m and t2 are each independently an integer of 2 or more and 20 or less, and m is t2 or more).

As specific examples of the polyfunctional (meth)acrylic monomer represented by the formula (B2-1), for example, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol Ethylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate Acrylate, butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, trimethylolpropane tri(methyl) )Acrylate, ethylene oxide modified trimethylolpropane tri(meth)acrylate, propylene oxide modified trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate Base) acrylate, glycerol di(meth)acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(methyl) )Acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate Acrylic ester, caprolactone modified pentaerythritol tri(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, caprolactone modified dipentaerythritol hexa(meth)acrylate, 2,2- Bis(4-(meth)acryloyloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypolyethoxyphenyl)propane, (methyl) Acrylic acid 2-hydroxy-3-(meth)acryloxy propyl ester, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate , Diglycidyl phthalate di(meth)acrylate, epichlorohydrin modified hexahydrophthalic di(meth)acrylate, glycerol triacrylate, glycerol polyglycidyl ether poly(methyl) Group) acrylate, urethane (meth)acrylate (ie, toluene diisocyanate, trimethyl-1,6-hexamethylene diisocyanate, or 1,6-hexamethylene diisocyanate, etc.) and (meth)acrylic acid The reactant of 2-hydroxyethyl), hydroxypivalate neopentyl glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, ethylene oxide modified neopentyl glycol di(meth) Meth) acrylate, propylene oxide modified neopentyl glycol di(meth)acrylate, ethylene oxide modified trimethylolpropane tri(meth)acrylate, propylene oxide modified trimethylol Tris(meth)acrylate, trimethylolpropane benzoate (meth)acrylate, tris((meth)acryloyloxyethyl) isocyanurate, alkoxy modified Trimethylolpropane tri(meth)acrylate, dipentaerythritol poly(meth)acrylate, alkyl modified dipentaerythritol tri(meth)acrylate, and ditrimethylolpropane tetra(meth)acrylic acid (Meth)acrylate, methylene bis(meth)acrylamide, (meth)acrylamide methylene ether, polyol and N-methylol Yl) Multifunctional monomers such as condensates of acrylamide, or triacryl formal, etc. These polyfunctional monomers can be used individually or in combination of 2 or more types.

Among the specific examples of the polyfunctional (meth)acrylate monomer represented by the above formula (B2-1), the tendency is to improve the adhesiveness of the photosensitive resin composition to the substrate and the strength of the photosensitive resin composition after curing From the viewpoint of the above, a polyfunctional monomer having trifunctional or higher functionality is preferred, a polyfunctional monomer having tetrafunctional or higher functionality is more preferred, and a polyfunctional monomer having pentafunctional or higher functionality is still more preferred. Particularly preferred are dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and mixtures thereof.

The content of the (B) crosslinking agent in the photosensitive resin composition is preferably 10% by mass or more and 60% by mass or less, and more preferably 15% by mass relative to the mass of the entire solid content of the photosensitive resin composition Above and below 50% by mass. By setting it in the above range, it tends to be easy to obtain a balance of sensitivity, developability, and resolution.

In addition, relative to the total mass of the (B) crosslinking agent, the content of the monofunctional (meth)acrylic monomer (B1) is 1% by mass or more and 100% by mass or less of the entire crosslinking agent component (B) , Preferably 3 mass% or more and 70 mass% or less, more preferably 5 mass% or more and 50 mass% or less. By setting the content of the (meth)acrylic monomer (B1) within the above-mentioned range, the photosensitive resin composition can accelerate the curing of the part that cannot be directly reached by the active energy during the position selective exposure of the photosensitive resin composition, thereby forming a thick film Specifically, for example, in the case of a cured film having a thickness of 5 μm or more and 50 μm or less, the curing can be sufficiently performed even in the vicinity of the substrate side located far from the exposure side.

As a still more preferable aspect, relative to the total mass of the (B) crosslinking agent, the (B) crosslinking agent preferably contains 1% by mass or more and 99% by mass or less of a monofunctional (meth)acrylic monomer (B1), and 1% by mass or more and 99% by mass or less of the polyfunctional (meth)acrylic monomer (B2), preferably containing 3% by mass or more and 50% by mass or less (B1), and 50% by mass The above and 97% by mass or less of the polyfunctional (meth)acrylic monomer (B2). In this case, the form of the above-mentioned thick coating film formed from the photosensitive resin composition is also as described above , The entire coating film is fully cured. Therefore, it is easy to make the taper angle of the patterned cured film formed by position-selective exposure and development a good angle close to vertical.

＜Photoinitiator (C)＞ The photosensitive resin composition further contains a photoinitiator (C). The photopolymerization initiator (C) is not particularly limited, and conventionally known photopolymerization initiators can be used.

Specific examples of the photopolymerization initiator (C) include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-[4- (2-Hydroxyethoxy)phenyl)-2-hydroxy-2-methyl-1-propane-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane -1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropane-1-one, 2,2-dimethoxy-1,2-diphenylethane -1-one, bis(4-dimethylaminophenyl) ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino (morpholino) propane-1 -Ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one, O-acetyl-1-[6-(2-methyl Benzyl)-9-ethyl-9H-carbazol-3-yl]ethanone oxime, (9-ethyl-6-nitro-9H-carbazol-3-yl)[4-(2 -Methoxy-1-methylethoxy)-2-methylphenyl]methanone O-acetoxime, 2-(benzylhydroxyimino)-1-[4-(phenyl Thio)phenyl)-1-octanone, 1-[9-ethyl-6-(pyrrol-2-ylcarbonyl)-9H-carbazol-3-yl]ethanone, 2,4,6-tri Methylbenzyl diphenyl phosphine oxide, 4-benzyl-4'-methyl dimethyl sulfide, 4-dimethylaminobenzoic acid, 4-dimethylaminobenzoic acid methyl ester Ester, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 4-dimethylamino-2-ethylhexyl benzoic acid, 4-dimethylamino- 2-Isoamylbenzoic acid, benzyl-β-methoxyethyl acetal, benzyl dimethyl ketal, 1-phenyl-1,2-propanedione-2-(O-ethoxy Carbonyl) oxime, methyl phthalate, 2-ethylanthraquinone, octamethylanthraquinone, 1,2-benzoanthraquinone, 2,3-diphenylanthraquinone, azobisiso Butyronitrile, benzyl peroxide, cumene hydroperoxide, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-(o-chlorophenyl)-4,5 -Bis(m-methoxyphenyl)-imidazolyl dimer, benzophenone, 2-chlorobenzophenone, p,p'-bisdimethylaminobenzophenone, 4,4' -Bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone, diphenylethylenedione, benzene Azoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, benzoin butyl ether, phenethyl Ketones, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, p-tert-butylacetophenone , P-Dimethylaminoacetophenone, p-tert-butyl trichloroacetophenone, p-tert-butyl dichloroacetophenone, α,α-dichloro-4-phenoxyacetophenone, dibenzo Cycloheptanone (dibenzosuberone), 4-dimethylaminobenzoic acid pentyl ester, 9-phenyl acridine, 1,7-bis-(9- Acridinyl)heptane, 1,5-bis-(9-acridinyl)pentane, 1,3-bis-(9-acridinyl)propane, p-methoxytriazine, 2,4,6 -Tris(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)s-triazine, 2-[2-(5-methylfuran-2-yl) Vinyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-s -Triazine, 2-[2-(4-Diethylamino-2-methylphenyl)vinyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2 -(3,4-Dimethoxyphenyl)vinyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxyphenyl)-4,6- Bis(trichloromethyl)-s-triazine, 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-n-butyl Oxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-bistrichloromethyl-6-(3-bromo-4-methoxy)phenyl-s -Triazine, 2,4-bistrichloromethyl-6-(2-bromo-4-methoxy)phenyl-s-triazine, 2,4-bistrichloromethyl-6-(3- Bromo-4-methoxy)styrylphenyl-s-triazine, 2,4-bistrichloromethyl-6-(2-bromo-4-methoxy)styrylphenyl-s- Triazine and so on. These photoinitiators can be used individually or in combination of 2 or more types.

(R^c1 為選自由1價有機基團、胺基、鹵素、硝基、及氰基組成的群組中的基團， n1為0以上且4以下的整數， n2為0或1， R^c2 為可具有取代基的苯基、或可具有取代基的咔唑基， R^c3 為氫原子、或碳原子數為1以上且6以下的烷基)。As the photopolymerization initiator (C), an oxime compound represented by the following formula (c1) is preferably used.

(R ^c1 is a group selected from the group consisting of a monovalent organic group, an amine group, a halogen, a nitro group, and a cyano group, n1 is an integer from 0 to 4, n2 is 0 or 1, R ^c2 It is a phenyl group which may have a substituent or a carbazolyl group which may have a substituent, and R ^c3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).

In the formula (c1), R ^c1 is not particularly limited as long as it does not interfere with the purpose of the present invention, and can be appropriately selected from various organic groups. Preferred examples when R ^c1 is an organic group include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, a saturated aliphatic acyl group, an alkoxycarbonyl group, A phenyl group that may have a substituent, a phenoxy group that may have a substituent, a benzyl group that may have a substituent, a phenoxycarbonyl group that may have a substituent, a benzyloxy group that may have a substituent, and the Substituent phenylalkyl group, optionally substituted naphthyl group, optionally substituted naphthyloxy group, optionally substituted naphthyloxy group, optionally substituted naphthyloxycarbonyl group, optionally substituted group Naphthoxy, naphthylalkyl which may have substituents, heterocyclic groups which may have substituents, amino groups, amino groups substituted by one or two organic groups, morpholin-1-yl, and Piperazin-1-yl, halogen, nitro, and cyano, etc. When n1 is an integer of 2 or more and 4 or less, R ^c1 may be the same or different. In addition, the number of carbon atoms of a substituent group does not include the number of carbon atoms of a substituent group that the substituent group further has.

When R ^c1 is an alkyl group, the number of carbon atoms is preferably 1 or more and 20 or less, and more preferably 1 or more and 6 or less carbon atoms. In addition, when R ^c1 is an alkyl group, it may be linear or branched. Specific examples when R ^c1 is an alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isoamyl Base, sec-pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, n-decyl, and isodecyl, etc. . In addition, when R ^c1 is an alkyl group, the alkyl group may include an ether bond (-O-) in the carbon chain. Examples of alkyl groups having ether bonds in the carbon chain include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxy Ethoxyethyl, methoxypropyl, etc.

When R ^c1 is an alkoxy group, the number of carbon atoms is preferably 1 or more and 20 or less, and the number of carbon atoms is more preferably 1 or more and 6 or less. In addition, when R ^c1 is an alkoxy group, it may be linear or branched. Specific examples when R ^c1 is an alkoxy group include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, and sec-butyloxy. Oxy, tert-butyloxy, n-pentyloxy, isopentyloxy, sec-pentyloxy, tert-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, Isooctyloxy, sec-octyloxy, tert-octyloxy, n-nonyloxy, isononyloxy, n-decyloxy, isodecyloxy, etc. In addition, when R ^c1 is an alkoxy group, the alkoxy group may include an ether bond (-O-) in the carbon chain. Examples of alkoxy groups having ether bonds in the carbon chain include methoxyethoxy, ethoxyethoxy, methoxyethoxyethoxy, and ethoxyethoxyethoxy. Group, propyloxyethoxyethoxy, and methoxypropyloxy.

When R ^c1 is a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms is 3 or more and 10 or less, and the number of carbon atoms is 3 or more and 6 or less. Specific examples when R ^c1 is a cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Specific examples when R ^c1 is a cycloalkoxy group include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy Base etc.

When R ^c1 is a saturated aliphatic oxy group or a saturated aliphatic oxy group, the number of carbon atoms is preferably 2 or more and 20 or less, and more preferably 2 or more and 7 or less carbon atoms. Specific examples when R ^c1 is a saturated aliphatic group include acetyl group, propyl group, n-butyryl group, 2-methylpropionyl group, n-pentyl group, and 2,2-dimethylpropionyl group. N-hexyl, n-heptanyl, n-octyl, n-nonanyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl Group, n-pentadecyl acyl, and n-hexadecyl acyl, etc. As specific examples when R ^c1 is a saturated aliphatic oxy group, acetoxy group, propyloxy group, n-butoxy group, 2-methylpropoxy group, n-pentoxy group, 2 , 2-Dimethylpropionyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decanoyloxy, n-undecyloxy, n-decyloxy Dialkyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy and the like.

When R ^c1 is an alkoxycarbonyl group, the number of carbon atoms is preferably 2 or more and 20 or less, and more preferably 2 or more and 7 or less carbon atoms. Specific examples when R ^c1 is an alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyl Oxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, isopentyloxycarbonyl, sec-pentyloxycarbonyl, tert-pentyloxycarbonyl, n-hexyloxy Carbonyl, n-heptyloxycarbonyl, n-octyloxycarbonyl, isooctyloxycarbonyl, sec-octyloxycarbonyl, tert-octyloxycarbonyl, n-nonyloxycarbonyl, isononyloxycarbonyl , N-decyloxycarbonyl, and isodecyloxycarbonyl, etc.

When R ^c1 is a phenylalkyl group, the number of carbon atoms is preferably 7 or more and 20 or less, and more preferably 7 or more and 10 or less carbon atoms. In addition, when R ^c1 is a naphthylalkyl group, the number of carbon atoms is preferably 11 or more and 20 or less, and more preferably 11 or more and 14 or less carbon atoms. Specific examples when R ^c1 is a phenylalkyl group include benzyl, 2-phenylethyl, 3-phenylpropyl, and 4-phenylbutyl. Specific examples when R ^c1 is naphthylalkyl include α-naphthylmethyl, β-naphthylmethyl, 2-(α-naphthyl)ethyl, and 2-(β-naphthyl) Ethyl. When R ^c1 is phenylalkyl or naphthylalkyl, R ^c1 may further have a substituent on the phenyl or naphthyl group.

When R ^c1 is a heterocyclic group, the heterocyclic group is a monocyclic ring containing more than one of five or six members of N, S, O, or the condensation of these monocyclic rings with each other, or the condensation of this monocyclic ring with a benzene ring Heterocyclic group. When the heterocyclic group is a condensed ring, the number of rings is 3 or less. Examples of the heterocyclic ring constituting the heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, and pyrimidine. , Pyridazine, benzofuran, benzothiophene, indole, isoindole, indoleazine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, iso Quinoline, quinazoline, phthalazine, cinnoline, and quinoxaline, etc. When R ^c1 is a heterocyclic group, the heterocyclic group may further have a substituent.

When R ^c1 is an amino group substituted with one or two organic groups, preferable examples of the organic group include an alkyl group having 1 to 20 carbon atoms, and 3 or more carbon atoms. Cycloalkyl groups of 10 or less, saturated aliphatic aliphatic groups having 2 or more and 20 or less carbon atoms, phenyl groups that may have substituents, benzyl groups that may have substituents, and the number of carbon atoms that may have substituents 7 or more and 20 or less phenylalkyl groups, optionally substituted naphthyl groups, optionally substituted naphthylmethyl groups, optionally substituted naphthylalkyl groups having 11 or more and 20 carbon atoms, and Heterocyclic group and so on. Specific examples of these preferable organic groups are the same as R ^c1 . Specific examples of the amino group substituted with one or two organic groups include methylamino, ethylamino, diethylamino, n-propylamino, di-n-propylamino, Isopropylamino, n-butylamino, di-n-butylamino, n-pentylamino, n-hexylamino, n-heptylamino, n-octylamino, n-nonylamino, n-decyl Amino, phenylamino, naphthylamino, acetylamino, propionylamino, n-butyrylamino, n-pentanylamino, n-hexylamino, n-heptanylamino , N-octylamino, n-decanoylamino, benzylamino, α-naphthylamino, β-naphthylamino, etc.

^Examples of the substituent when the phenyl, naphthyl, and heterocyclic group contained in R ^c1 further have a substituent include an alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. The alkoxy group, the saturated aliphatic acyl group having 2 or more and 7 or less carbon atoms, the alkoxycarbonyl group having 2 or more and less than 7 carbon atoms, the saturated aliphatic acyl group having 2 or more and 7 or less carbon atoms An oxy group, a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl, piperidine Piperazin-1-yl, halogen, nitro, and cyano, etc. When the phenyl group, naphthyl group, and heterocyclic group contained in R ^c1 further have a substituent, the number of the substituent is not limited as long as it does not interfere with the purpose of the present invention, and it is preferably 1 or more and 4 or less. When the phenyl group, naphthyl group, and heterocyclic group contained in R ^c1 have multiple substituents, the multiple substituents may be the same or different.

R ^c1 is preferably selected from alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, in view of chemical stability, small steric obstacles, and easy synthesis of oxime ester compounds. The group consisting of saturated aliphatic acyl groups having 2 or more and 7 or less carbon atoms is more preferably an alkyl group having 1 or more and 6 or less carbon atoms, and particularly preferably a methyl group.

Regarding the phenyl group to which R ^c1 is bonded, the position of the bonding bond between the phenyl group and the main skeleton of the oxime ester compound is set to position 1, and the position of the methyl group is set to position 2, when R ^c1 is bound to the phenyl group , Preferably 4 or 5 positions, more preferably 5 positions. In addition, n1 is preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0 or 1.

R ^c2 is a phenyl group which may have a substituent or a carbazolyl group which may have a substituent. In addition, when R ^c2 is a carbazolyl group which may have a substituent, the nitrogen atom on the carbazolyl group may be substituted with an alkyl group having 1 to 6 carbon atoms.

In R ^c2 , the substituent which the phenyl group or the carbazolyl group has is not specifically limited in the range which does not interfere with the objective of this invention. Examples of preferable substituents that a phenyl group or a carbazolyl group may have on a carbon atom include an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, Cycloalkyl groups with 3 or more and 10 carbon atoms, cycloalkoxy groups with 3 or more and 10 carbon atoms, saturated aliphatic aliphatic groups with 2 or more and 20 carbon atoms, and 2 or more and 20 carbon atoms Alkoxycarbonyl group, saturated aliphatic acyloxy group having 2 or more and 20 carbon atoms, optionally substituted phenyl group, optionally substituted phenoxy group, optionally substituted phenylthio group, Substituent benzyl group, optionally substituted phenoxycarbonyl group, optionally substituted benzyloxy group, optionally substituted phenylalkyl group having 7 to 20 carbon atoms, Substituent naphthyl group, optionally substituted naphthyloxy group, optionally substituted naphthyloxycarbonyl group, optionally substituted naphthyloxycarbonyl group, optionally substituted naphthyloxycarbonyl group, optionally substituted Naphthylalkyl groups with 11 or more carbon atoms and 20 or less, heterocyclic groups which may have substituents, heterocyclic groups which may have substituents, carbonyl groups, amine groups, amines substituted with one or two organic groups Group, morpholin-1-yl, piperazin-1-yl, halogen, nitro, and cyano, etc.

When R ^c2 is a carbazolyl group, examples of preferable substituents that the carbazolyl group may have on the nitrogen atom include an alkyl group having 1 or more and 20 or less carbon atoms, and 3 or more and 10 or less carbon atoms. Cycloalkyl groups, saturated aliphatic acyl groups having 2 or more and 20 carbon atoms, alkoxycarbonyl groups having 2 or more and 20 carbon atoms, phenyl groups that may have substituents, and benzyl groups that may have substituents Group, optionally substituted phenoxycarbonyl group, optionally substituted phenylalkyl group having 7 or more and 20 carbon atoms, optionally substituted naphthyl group, optionally substituted naphthylmethyl group, available A substituted naphthyloxycarbonyl group, an optionally substituted naphthylalkyl group having 11 to 20 carbon atoms, an optionally substituted heterocyclic group, an optionally substituted heterocyclic carbonyl group, and the like. Among these substituents, an alkyl group having 1 or more and 20 or less carbon atoms is preferable, an alkyl group having 1 or more and 6 or less carbon atoms is more preferable, and an ethyl group is particularly preferable.

Regarding specific examples of substituents that a phenyl group or a carbazolyl group may have, an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, and a saturated aliphatic acyl group Oxy group, optionally substituted phenylalkyl group, optionally substituted naphthylalkyl group, optionally substituted heterocyclic group, and amino group substituted by one or two organic groups and R ^c1 same.

Examples of substituents when the phenyl group, naphthyl group, and heterocyclic group included in the substituent group of the phenyl group or the carbazolyl group further have a substituent group in R ^c2 include 1 to 6 carbon atoms Alkyl group having 1 to 6 carbon atoms; saturated aliphatic acyl group having 2 to 7 carbon atoms; alkoxycarbonyl having 2 to 7 carbon atoms; 2 carbon atoms Saturated aliphatic aliphatic oxy groups of more than 7 and less than 7; phenyl; naphthyl; benzyl; naphthyl; selected from alkyl groups having 1 to 6 carbon atoms, morpholin-1-yl, A benzyl group substituted by a group consisting of piperazin-1-yl and phenyl; a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms; having 1 carbon atom Dialkylamino groups of alkyl groups above and below 6; morpholin-1-yl; piperazin-1-yl; halogen; nitro; cyano. When the phenyl group, naphthyl group, and heterocyclic group included in the substituents of the phenyl group or the carbazolyl group further have a substituent, the number of the substituents is not limited within a range that does not interfere with the purpose of the present invention. Preferably it is 1 or more and 4 or less. When the phenyl group, naphthyl group, and heterocyclic group have multiple substituents, the multiple substituents may be the same or different.

^Among R ^c2 , from the viewpoint of easily obtaining a photopolymerization initiator excellent in sensitivity, a group represented by the following formula (c2) or (c3) is preferred, and a group represented by the following formula (c2) is more preferred, Especially preferably, it is a group represented by the following formula (c2), and A is a group of S.

(R^c4 為選自由1價有機基團、胺基、鹵素、硝基、及氰基所組成之群組中的基團，A為S或O，n3為0以上且4以下的整數)。

(R ^c4 is a group selected from the group consisting of a monovalent organic group, an amine group, a halogen, a nitro group, and a cyano group, A is S or O, and n3 is an integer of 0 to 4).

(R^c5 及R^c6 分別為1價有機基團)。

(R ^c5 and R ^c6 are each a monovalent organic group).

When R ^c4 in the formula (c2) is an organic group, it can be selected from various organic groups within a range that does not hinder the purpose of the present invention. As a preferable example when R ^c4 in the formula (c2) is an organic group, an alkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; and 2 carbon atoms are mentioned. Saturated aliphatic acyl group of more than 7 and less than 7; alkoxycarbonyl group having 2 to 7 carbon atoms; saturated aliphatic acyl group of more than 2 and less than 7 carbon atoms; phenyl group; naphthyl group; benzyl group Group; Naphthanoyl; substituted with a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl, piperazin-1-yl, and phenyl Benzyl; a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms; a dialkylamino group having an alkyl group having 1 to 6 carbon atoms; morpholin-1-yl; Piperazin-1-yl; halogen; nitro; cyano.

In R ^c4 , preferably benzyl; naphthyl; selected from alkyl groups having 1 to 6 carbon atoms, morpholin-1-yl, piperazin-1-yl, and phenyl Benzyl; nitro, more preferably benzyl; naphthyl; 2-methylphenylcarbonyl; 4-(piperazin-1-yl)benzene Carbonyl; 4-(phenyl)phenylcarbonyl.

In addition, in formula (c2), n3 is preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0 or 1. n3 is 1, R ^c4 of the bonding position, preferably with respect to the R ^c4 phenyl bonded to an oxygen atom or a sulfur atom is bonded to the para linkages.

R ^c5 in formula (c3) can be selected from various organic groups within a range that does not hinder the purpose of the present invention. Preferable examples of R ^c5 include alkyl groups having 1 or more and 20 carbon atoms, cycloalkyl groups having 3 or more and 10 carbon atoms, and saturated aliphatic aliphatic groups having 2 or more and 20 carbon atoms. , Alkoxycarbonyl groups with 2 or more and 20 carbon atoms, optionally substituted phenyl groups, optionally substituted benzyl groups, optionally substituted phenoxycarbonyl groups, optionally substituted carbon atoms A phenylalkyl group having a number of 7 or more and 20 or less, an optionally substituted naphthyl group, an optionally substituted naphthylmethyl group, an optionally substituted naphthyloxycarbonyl group, an optionally substituted carbon number of 11 The naphthyl alkyl group of above and 20 or less, the heterocyclic group which may have a substituent, the heterocyclic carbonyl group which may have a substituent, etc.,.

^Among R ^c5 , an alkyl group having 1 or more and 20 or less carbon atoms is preferable, an alkyl group having 1 or more and 6 or less carbon atoms is more preferable, and an ethyl group is particularly preferable.

R ^c6 in the formula (c3) is not particularly limited as long as it does not hinder the purpose of the present invention, and it can be selected from various organic groups. Specific examples of preferred groups as R ^c6 include alkyl groups having 1 to 20 carbon atoms, optionally substituted phenyl groups, optionally substituted naphthyl groups, and optionally substituted groups. Heterocyclic group. As R ^c6 , among these groups, a phenyl group which may have a substituent is more preferable, and a 2-methylphenyl group is particularly preferable.

^Examples of substituents when the phenyl, naphthyl, and heterocyclic groups contained in R ^c4 , R ^c5 or R ^c6 further have a substituent include an alkyl group having 1 to 6 carbon atoms, and the number of carbon atoms Alkoxy groups with 1 or more and 6 or less, saturated aliphatic acyl groups with 2 or more and 7 carbon atoms, alkoxycarbonyl groups with 2 or more and 7 carbon atoms, saturated fats with 2 or more and 7 carbon atoms Group acyloxy group, monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, dialkylamino group having an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl, Piperazin-1-yl, halogen, nitro, and cyano, etc. When the phenyl group, naphthyl group, and heterocyclic group contained in R ^c4 , R ^c5 or R ^c6 further have a substituent, the number of the substituent is not limited within a range that does not interfere with the purpose of the present invention, and is preferably 1 Above and below 4. When the phenyl group, naphthyl group, and heterocyclic group contained in R ^c4 , R ^c5 or R ^c6 have multiple substituents, the multiple substituents may be the same or different.

R ^c3 in the formula (c1) is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. As R ^c3 , methyl or ethyl is preferred, and methyl is more preferred.

Among the oxime ester compounds represented by the formula (c1), particularly preferred compounds include the following PI-1 to PI-42.

In addition, the photopolymerization initiator (C) is preferably an oxime ester compound represented by the following formula (c4).

(R^c7 為氫原子、硝基或1價有機基團，R^c8 及R^c9 各自為可具有取代基的鏈狀烷基、可具有取代基的環狀有機基團、或氫原子，R^c8 與R^c9 可相互鍵結形成環，R^c10 為1價有機基團，R^c11 為氫原子、可具有取代基的碳原子數1以上且11以下的烷基、或可具有取代基的芳基，n4為0以上且4以下的整數，n5為0或1)。

(R ^c7 is a hydrogen atom, a nitro group or a monovalent organic group, R ^c8 and R ^c9 are each a chain alkyl group which may have a substituent, a cyclic organic group which may have a substituent, or a hydrogen atom, R ^c8 It can be bonded with R ^c9 to form a ring, R ^c10 is a monovalent organic group, R ^c11 is a hydrogen atom, an optionally substituted alkyl group having 1 to 11 carbon atoms, or an optionally substituted aryl group , N4 is an integer from 0 to 4, and n5 is 0 or 1).

Here, as the oxime compound used for producing the oxime ester compound of the formula (c4), a compound represented by the following formula (c5) is preferred.

(R^c7 、R^c8 、R^c9 、R^c10 、n4、及n5與式(c4)同樣)。

(R ^c7 , R ^c8 , R ^c9 , R ^c10 , n4, and n5 are the same as the formula (c4)).

In formulas (c4) and (c5), R ^c7 is a hydrogen atom, a nitro group, or a monovalent organic group. R ^c7 is bonded to a six-membered aromatic ring different from the six-membered aromatic ring to which the group represented by -(CO) _n5 -is bonded to the sulphur ring in the formula (c4). In formula (c4), the bonding position of R ^c7 with respect to the sulphur ring is not particularly limited. When the compound represented by the formula (c4) has one or more R ^c7 , it is preferable to easily synthesize the compound represented by the formula (c4), etc., and one of the more than one R ^c7 is preferably bonded to the 2-position in the 茀 ring . R ^c7 is a plurality, the plurality of R ^c7 may be the same or different.

When R ^c7 is an organic group, R ^c7 is not particularly limited as long as it does not interfere with the purpose of the present invention, and can be appropriately selected from various organic groups. Preferred examples when R ^c7 is an organic group include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, a saturated aliphatic acyl group, an alkoxycarbonyl group, A phenyl group that may have a substituent, a phenoxy group that may have a substituent, a benzyl group that may have a substituent, a phenoxycarbonyl group that may have a substituent, a benzyloxy group that may have a substituent, and the Substituent phenylalkyl group, optionally substituted naphthyl group, optionally substituted naphthyloxy group, optionally substituted naphthyloxy group, optionally substituted naphthyloxycarbonyl group, optionally substituted group Naphthoxy, naphthylalkyl which may have substituents, heterocyclic groups which may have substituents, heterocyclic carbonyl groups which may have substituents, amine groups substituted with one or two organic groups, Lin-1-yl, piperazin-1-yl, etc.

When R ^c7 is an alkyl group, the number of carbon atoms of the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less. In addition, when R ^c7 is an alkyl group, it may be linear or branched. Specific examples when R ^c7 is an alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isoamyl Base, sec-pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, n-decyl, and isodecyl, etc. . In addition, when R ^c7 is an alkyl group, the alkyl group may include an ether bond (-O-) in the carbon chain. Examples of alkyl groups having ether bonds in the carbon chain include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxy Ethoxyethyl, methoxypropyl, etc.

When R ^c7 is an alkoxy group, the number of carbon atoms of the alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less. In addition, when R ^c7 is an alkoxy group, it may be linear or branched. Specific examples when R ^c7 is an alkoxy group include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, and sec-butyloxy. Oxy, tert-butyloxy, n-pentyloxy, isopentyloxy, sec-pentyloxy, tert-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, Isooctyloxy, sec-octyloxy, tert-octyloxy, n-nonyloxy, isononyloxy, n-decyloxy, isodecyloxy, etc. In addition, when R ^c7 is an alkoxy group, the alkoxy group may include an ether bond (-O-) in the carbon chain. Examples of alkoxy groups having ether bonds in the carbon chain include methoxyethoxy, ethoxyethoxy, methoxyethoxyethoxy, and ethoxyethoxyethoxy. Group, propyloxyethoxyethoxy, and methoxypropyloxy.

When R ^c7 is a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms of the cycloalkyl group or the cycloalkoxy group is preferably 3 or more and 10 or less, and more preferably 3 or more and 6 or less. Specific examples when R ^c7 is a cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Specific examples when R ^c7 is a cycloalkoxy group include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy Base etc.

When R ^c7 is a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, the saturated aliphatic acyl group or the saturated aliphatic acyloxy group preferably has 2 or more and 21 or less carbon atoms, more preferably 2 or more and 7 or less. Specific examples when R ^c7 is a saturated aliphatic group include acetyl group, propyl group, n-butyryl group, 2-methylpropionyl group, n-pentyl group, and 2,2-dimethylpropionyl group. N-hexyl, n-heptanyl, n-octyl, n-nonanyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl Group, n-pentadecyl acyl, and n-hexadecyl acyl, etc. Specific examples when R ^c7 is a saturated aliphatic oxy group include acetoxy group, propyloxy group, n-butoxy group, 2-methylpropoxy group, n-pentoxy group, 2 , 2-Dimethylpropionyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decanoyloxy, n-undecyloxy, n-decyloxy Dialkyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy and the like.

When R ^c7 is an alkoxycarbonyl group, the number of carbon atoms of the alkoxycarbonyl group is preferably 2 or more and 20 or less, more preferably 2 or more and 7 or less. Specific examples when R ^c7 is an alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyl Oxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, isopentyloxycarbonyl, sec-pentyloxycarbonyl, tert-pentyloxycarbonyl, n-hexyloxy Carbonyl, n-heptyloxycarbonyl, n-octyloxycarbonyl, isooctyloxycarbonyl, sec-octyloxycarbonyl, tert-octyloxycarbonyl, n-nonyloxycarbonyl, isononyloxycarbonyl , N-decyloxycarbonyl, and isodecyloxycarbonyl, etc.

When R ^c7 is a phenylalkyl group, the number of carbon atoms of the phenylalkyl group is preferably 7 or more and 20 or less, more preferably 7 or more and 10 or less. When R ^c7 is a naphthylalkyl group, the number of carbon atoms of the naphthylalkyl group is preferably 11 or more and 20 or less, and more preferably 11 or more and 14 or less. Specific examples when R ^c7 is a phenylalkyl group include benzyl, 2-phenylethyl, 3-phenylpropyl, and 4-phenylbutyl. Specific examples when R ^c7 is naphthylalkyl include α-naphthylmethyl, β-naphthylmethyl, 2-(α-naphthyl)ethyl, and 2-(β-naphthyl) Ethyl. When R ^c7 is phenylalkyl or naphthylalkyl, R ^c7 may further have a substituent on the phenyl or naphthyl group.

When R ^c7 is a heterocyclic group, the heterocyclic group is a five- or six-membered monocyclic ring containing more than one N, S, O, or the condensation of these monocyclic rings with each other, or the condensation of this monocyclic ring with a benzene ring Heterocyclic group. When the heterocyclic group is a condensed ring, the number of rings is 3 or less. The heterocyclic group may be an aromatic group (heteroaryl) or a non-aromatic group. Examples of the heterocyclic ring constituting the heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, and pyrimidine. , Pyridazine, benzofuran, benzothiophene, indole, isoindole, indoleazine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, iso Quinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran, etc. When R ^c7 is a heterocyclic group, the heterocyclic group may further have a substituent.

When R ^c7 is a heterocyclic carbonyl group, the heterocyclic group contained in the heterocyclic carbonyl group is the same as when R ^c7 is a heterocyclic group.

When R ^c7 is an amine group substituted with one or two organic groups, preferable examples of the organic group include an alkyl group having 1 to 20 carbon atoms, and 3 or more carbon atoms. Cycloalkyl groups of 10 or less, saturated aliphatic aliphatic groups having 2 or more and 21 or less carbon atoms, optionally substituted phenyl groups, optionally substituted benzyl groups, and optionally substituted carbon atoms 7 or more and 20 or less phenylalkyl groups, optionally substituted naphthyl groups, optionally substituted naphthylmethyl groups, optionally substituted naphthylalkyl groups having 11 or more and 20 carbon atoms, and Heterocyclic group and so on. Specific examples of these preferable organic groups are the same as R ^c7 . Specific examples of the amino group substituted with one or two organic groups include methylamino, ethylamino, diethylamino, n-propylamino, di-n-propylamino, Isopropylamino, n-butylamino, di-n-butylamino, n-pentylamino, n-hexylamino, n-heptylamino, n-octylamino, n-nonylamino, n-decyl Amino, phenylamino, naphthylamino, acetylamino, propionylamino, n-butyrylamino, n-pentanylamino, n-hexylamino, n-heptanylamino , N-octylamino, n-decanoylamino, benzylamino, α-naphthylamino, β-naphthylamino, etc.

^Examples of the substituent when the phenyl group, naphthyl group, and heterocyclic group contained in R ^c7 further have a substituent include an alkyl group having 1 to 6 carbon atoms, and a carbon number of 1 to 6 The alkoxy group, the saturated aliphatic acyl group having 2 or more and 7 or less carbon atoms, the alkoxycarbonyl group having 2 or more and less than 7 carbon atoms, the saturated aliphatic acyl group having 2 or more and 7 or less carbon atoms An oxy group, a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl, Piperazin-1-yl, halogen, nitro, and cyano, etc. When the phenyl group, naphthyl group, and heterocyclic group contained in R ^c7 further have a substituent, the number of the substituent is not limited as long as it does not interfere with the purpose of the present invention, and it is preferably 1 or more and 4 or less. When the phenyl group, naphthyl group, and heterocyclic group contained in R ^c7 have multiple substituents, the multiple substituents may be the same or different.

^{Among the} groups described above, when R ^c7 is a nitro group or a group represented by R ^c12 -CO-, the sensitivity tends to increase, so it is preferred. R ^c12 is not particularly limited as long as it does not interfere with the purpose of the present invention, and it can be selected from various organic groups. Examples of the group preferably as R ^c12 include an alkyl group having 1 to 20 carbon atoms, a substituted phenyl group, a substituted naphthyl group, and a substituted group The heterocyclic group. Among these groups, as R ^c12 , 2-methylphenyl, thiophen-2-yl, and α-naphthyl are particularly preferred. In addition, when R ^c7 is a hydrogen atom, the transparency tends to become better, so it is preferred. Moreover, when R ^c7 is a hydrogen atom and R ^c10 is a group represented by the formula (c4a) or (c4b) described later, there is a tendency that transparency becomes better.

In the formula (c4), R ^c8 and R ^c9 are each a linear alkyl group which may have a substituent, a cyclic organic group which may have a substituent, or a hydrogen atom. R ^c8 and R ^c9 can be bonded to each other to form a ring. Among these groups, R ^c8 and R ^{c9 are} preferably a chain alkyl group which may have a substituent. When R ^c8 and R ^c9 are a chain alkyl group which may have a substituent, the chain alkyl group may be a straight chain alkyl group or a branched chain alkyl group.

When R ^c8 and R ^c9 are unsubstituted chain alkyl groups, the number of carbon atoms of the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 6 the following. Specific examples when R ^c8 and R ^c9 are chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-butyl Pentyl, isopentyl, sec-pentyl, t-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, t-octyl, n-nonyl, isononyl, n-decyl, And isodecyl and so on. In addition, when R ^c8 and R ^c9 are an alkyl group, the alkyl group may include an ether bond (-O-) in the carbon chain. Examples of alkyl groups having ether bonds in the carbon chain include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxy Ethoxyethyl, methoxypropyl, etc.

When R ^c8 and R ^c9 are chain alkyl groups having substituents, the number of carbon atoms of the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 6 or less . In this case, the carbon number of the chain alkyl does not include the carbon number of the substituent. The chain alkyl group having a substituent is preferably linear. The substituent that the alkyl group may have is not particularly limited as long as it does not interfere with the purpose of the present invention. Preferred examples of the substituent include a cyano group, a halogen atom, a cyclic organic group, and an alkoxycarbonyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, and a bromine atom are preferable. Examples of cyclic organic groups include cycloalkyl groups, aromatic hydrocarbon groups, and heterocyclic groups. The specific examples of the cycloalkyl group are the same as the preferred examples when R ^c7 is a cycloalkyl group. Specific examples of aromatic hydrocarbon groups include phenyl, naphthyl, biphenyl, anthracenyl, and phenanthryl. Specific examples of the heterocyclic group are the same as the preferred examples when R ^c7 is a heterocyclic group. When R ^c7 is an alkoxycarbonyl group, the alkoxy group contained in the alkoxycarbonyl group may be linear or branched, and is preferably linear. The number of carbon atoms of the alkoxy group contained in the alkoxycarbonyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less.

When the chain alkyl group has a substituent, the number of substituents is not particularly limited. The number of preferred substituents varies according to the number of carbon atoms of the chain alkyl group. The number of substituents is typically 1 or more and 20 or less, preferably 1 or more and 10 or less, and more preferably 1 or more and 6 or less.

When R ^c8 and R ^c9 are cyclic organic groups, the cyclic organic group may be an alicyclic group or an aromatic group. Examples of cyclic organic groups include aliphatic cyclic hydrocarbon groups, aromatic hydrocarbon groups, and heterocyclic groups. When R ^c8 and R ^c9 are cyclic organic groups, the substituents that the cyclic organic group may have are the same as when R ^c8 and R ^c9 are chain alkyl groups.

When R ^c8 and R ^c9 are aromatic hydrocarbon groups, the aromatic hydrocarbon group is preferably: a phenyl group, or a group formed by bonding a plurality of benzene rings via a carbon-carbon bond, or a group formed by condensation of a plurality of benzene rings group. When the aromatic hydrocarbon group is a phenyl group or a group formed by bonding or condensing multiple benzene rings, the number of benzene rings contained in the aromatic hydrocarbon group is not particularly limited, but is preferably 3 or less, more preferably 2 or less, Especially preferred is 1. Preferable specific examples of the aromatic hydrocarbon group include phenyl, naphthyl, biphenyl, anthryl, and phenanthryl.

When R ^c8 and R ^c9 are aliphatic cyclic hydrocarbon groups, the aliphatic cyclic hydrocarbon groups may be monocyclic or polycyclic. The number of carbon atoms of the aliphatic cyclic hydrocarbon group is not particularly limited, but it is preferably 3 or more and 20 or less, and more preferably 3 or more and 10 or less. Examples of monocyclic cyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, isobornyl, tricyclononyl, Tricyclodecyl, tetracyclododecyl, adamantyl, etc.

When R ^c8 and R ^c9 are heterocyclic groups, the heterocyclic group is a five-membered or six-membered monocyclic ring containing at least one N, S, O, or the monocyclic rings are condensed with each other, or the monocyclic ring and A heterocyclic group formed by condensation of benzene ring. When the heterocyclic group is a condensed ring, the number of rings is 3 or less. The heterocyclic group may be an aromatic group (heteroaryl) or a non-aromatic group. Examples of the heterocyclic ring constituting the heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, and pyrimidine. , Pyridazine, benzofuran, benzothiophene, indole, isoindole, indoleazine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, iso Quinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran, etc.

R ^c8 and R ^c9 can be bonded to each other to form a ring. The group including the ring formed by R ^c8 and R ^c9 is preferably a cycloalkylidene group. When R ^c8 and R ^{c9 are} bonded to form a cycloalkylidene group, the ring constituting the cycloalkylidene group is preferably a five-membered ring to a six-membered ring, and more preferably a five-membered ring.

When the group formed by bonding R ^c8 and R ^c9 is a cycloalkylidene group, the cycloalkylidene group may be condensed with one or more other rings. Examples of rings that can be condensed with cycloalkylidene groups include benzene ring, naphthalene ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, furan ring, Thiophene ring, pyrrole ring, pyridine ring, pyrazine ring, and pyrimidine ring, etc.

^Among R ^c8 and R ^c9 described above, examples of preferable groups include groups represented by the formula -A ¹ -A ² . In the formula, A ¹ is a linear alkylene group, and A ² is an alkoxy group, a cyano group, a halogen atom, a halogenated alkyl group, a cyclic organic group, or an alkoxycarbonyl group.

The number of carbon atoms of the linear extended alkyl group of A ¹ is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less. When A ² is an alkoxy group, the alkoxy group may be linear or branched, preferably linear. The number of carbon atoms of the alkoxy group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less. When A ² is a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are preferable, and a fluorine atom, a chlorine atom, and a bromine atom are more preferable. When A ² is a halogenated alkyl group, the halogen atom contained in the halogenated alkyl group is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom. The halogenated alkyl group may be linear or branched, and is preferably linear. When A ² is a cyclic organic group, examples of the cyclic organic group are the same as the cyclic organic group that R ^c8 and R ^{c9 have} as substituents. When A ² is an alkoxycarbonyl group, examples of the alkoxycarbonyl group are the same as the alkoxycarbonyl group that R ^c8 and R ^{c9 have} as substituents.

Preferred specific examples of R ^c8 and R ^c9 include alkyl groups such as ethyl, n-propyl, n-butyl, n-hexyl, n-heptyl, and n-octyl; 2-methoxyethyl, 3-methoxy n-propyl, 4-methoxy n-butyl, 5-methoxy n-pentyl, 6-methoxy n-hexyl, 7-methoxy n-heptyl, 8-methoxy n Octyl, 2-ethoxyethyl, 3-ethoxy n-propyl, 4-ethoxy n-butyl, 5-ethoxy n-pentyl, 6-ethoxy n-hexyl, 7-ethoxy N-heptyl and 8-ethoxy n-octyl and other alkoxyalkyl groups; 2-cyanoethyl, 3-cyano n-propyl, 4-cyano n-butyl, 5-cyano n-pentyl Cyanoalkyl, such as 6-cyano n-hexyl, 7-cyano n-heptyl, and 8-cyano n-octyl; 2-phenylethyl, 3-phenyl n-propyl, 4-phenyl Phenylalkyl groups such as n-butyl, 5-phenyl n-pentyl, 6-phenyl n-hexyl, 7-phenyl n-heptyl, and 8-phenyl n-octyl; 2-cyclohexyl ethyl, 3- Cyclohexyl n-propyl, 4-cyclohexyl n-butyl, 5-cyclohexyl n-pentyl, 6-cyclohexyl n-hexyl, 7-cyclohexyl n-heptyl, 8-cyclohexyl n-octyl, 2-cyclopentyl Ethyl, 3-cyclopentyl n-propyl, 4-cyclopentyl n-butyl, 5-cyclopentyl n-pentyl, 6-cyclopentyl n-hexyl, 7-cyclopentyl n-heptyl, and 8- Cycloalkylalkyl such as cyclopentyl n-octyl; 2-methoxycarbonyl ethyl, 3-methoxycarbonyl n-propyl, 4-methoxycarbonyl n-butyl, 5-methoxycarbonyl n-pentyl Group, 6-methoxycarbonyl n-hexyl, 7-methoxycarbonyl n-heptyl, 8-methoxycarbonyl n-octyl, 2-ethoxycarbonyl ethyl, 3-ethoxycarbonyl n-propyl, 4-ethoxycarbonyl n-butyl, 5-ethoxycarbonyl n-pentyl, 6-ethoxycarbonyl n-hexyl, 7-ethoxycarbonyl n-heptyl, 8-ethoxycarbonyl n-octyl, etc. Alkoxycarbonylalkyl; 2-chloroethyl, 3-chloro-n-propyl, 4-chloro-n-butyl, 5-chloro-n-pentyl, 6-chloro-n-hexyl, 7-chloro-n-heptyl, 8-chloro N-octyl, 2-bromoethyl, 3-bromo-n-propyl, 4-bromo-n-butyl, 5-bromo-pentyl, 6-bromo-hexyl, 7-bromo-heptyl, 8-bromo-octyl , 3,3,3-trifluoropropyl, and 3,3,4,4,5,5,5-heptafluoro-n-pentyl and other halogenated alkyl groups.

As R ^c8 and R ^c9 , the preferred groups mentioned above are ethyl, n-propyl, n-butyl, n-pentyl, 2-methoxyethyl, 2-cyanoethyl, 2-phenylethyl Group, 2-cyclohexylethyl, 2-methoxycarbonylethyl, 2-chloroethyl, 2-bromoethyl, 3,3,3-trifluoropropyl, and 3,3,4,4, 5,5,5-Heptafluoro-n-pentyl.

Examples of preferable organic groups for R ^c10 include alkyl groups, alkoxy groups, cycloalkyl groups, cycloalkoxy groups, saturated aliphatic acyl groups, alkoxycarbonyl groups, and saturated fatty acids in the same way as R ^c7 . Group acyloxy group, optionally substituted phenyl group, optionally substituted phenoxy group, optionally substituted benzyl group, optionally substituted phenoxycarbonyl group, optionally substituted benzyl group Oxy group, optionally substituted phenylalkyl group, optionally substituted naphthyl group, optionally substituted naphthyloxy group, optionally substituted naphthyloxy group, optionally substituted naphthyloxycarbonyl group, An optionally substituted naphthyloxy group, an optionally substituted naphthylalkyl group, an optionally substituted heterocyclic group, an optionally substituted heterocyclic carbonyl group, substituted by one or two organic groups The amine group, morpholin-1-yl, and piperazin-1-yl and so on. Specific examples of these groups are the same as those explained for R ^c7 . Moreover, as R ^c10 , a cycloalkylalkyl group, a phenoxyalkyl group which may have a substituent on an aromatic ring, and a phenylthioalkyl group which may have a substituent on an aromatic ring are also preferable. The substituents that the phenoxyalkyl group and the phenylthioalkyl group may have are the same as the substituents that the phenyl group included in R ^c7 may have.

Among the organic groups, R ^{c10 is} preferably an alkyl group, a cycloalkyl group, a phenyl group or a cycloalkylalkyl group which may have a substituent, and a phenylthioalkyl group which may have a substituent on the aromatic ring. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, and particularly preferably an alkyl group having 1 to 4 carbon atoms. The most preferred group is methyl. Among the phenyl groups that may have a substituent, a methylphenyl group is preferred, and a 2-methylphenyl group is more preferred. The number of carbon atoms of the cycloalkyl group contained in the cycloalkylalkyl group is preferably 5 or more and 10 or less, more preferably 5 or more and 8 or less, and particularly preferably 5 or 6. The number of carbon atoms of the alkylene group contained in the cycloalkylalkyl group is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, particularly preferably 2. Among cycloalkylalkyls, cyclopentylethyl is preferred. The number of carbon atoms of the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, particularly preferably 2. Among the phenylthioalkyl groups which may have a substituent on the aromatic ring, 2-(4-chlorophenylthio)ethyl is preferred.

In addition, as R ^c10 , a group represented by -A ³ -CO-OA ⁴ is also preferred. A ³ is a divalent organic group, preferably a divalent hydrocarbon group, preferably an alkylene group. A ⁴ is a monovalent organic group, preferably a monovalent hydrocarbon group.

When A ³ is an alkylene group, the alkylene group may be linear or branched, and is preferably linear. When A ³ is alkylene, alkylene group having a carbon number of 1 or more and is preferably 10 or less, more preferably 1 or more and 6 or less, particularly preferably 1 or more and 4 or less.

A ⁴ is a preferred embodiment, include a number of 1 or more carbon atoms and 10 or less alkyl carbon atoms is 7 or more and 20 or less aralkyl group and having 6 or more carbon atoms and 20 or less aromatic Group hydrocarbon group. Preferred specific examples of A ⁴ include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, Phenyl, naphthyl, benzyl, phenethyl, α-naphthylmethyl, β-naphthylmethyl, etc.

Preferred specific examples of the group represented by -A ³ -CO-OA ⁴ include 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-n-propyloxycarbonylethyl Group, 2-n-butyloxycarbonylethyl, 2-n-pentyloxycarbonylethyl, 2-n-hexyloxycarbonylethyl, 2-benzyloxycarbonylethyl, 2-phenoxycarbonyl Ethyl, 3-methoxycarbonyl n-propyl, 3-ethoxycarbonyl n-propyl, 3-n-propyloxycarbonyl n-propyl, 3-n-butyloxycarbonyl n-propyl, 3-n Pentyloxycarbonyl n-propyl, 3-n-hexyloxycarbonyl n-propyl, 3-benzyloxycarbonyl n-propyl, 3-phenoxycarbonyl n-propyl, etc.

(式(c4a)及(c4b)中，R^c13 及R^c14 各自為有機基團，n6為0以上且4以下的整數，R^c13 及R^c14 存在於苯環上的相鄰位置時，R^c13 與R^c14 可相互鍵結而形成環，n7為1以上且8以下的整數，n8為1以上且5以下的整數，n9為0以上且(n8+3)以下的整數，R^c15 為有機基團)。As mentioned above, R ^c10 has been described, and R ^{c10 is} preferably a group represented by the following formula (c4a) or (c4b).

(In formulas (c4a) and (c4b), R ^c13 and R ^c14 are each an organic group, n6 is an integer from 0 to 4, and R ^c13 and R ^c14 are present at adjacent positions on the benzene ring, R ^c13 It can bond with R ^c14 to form a ring, n7 is an integer from 1 to 8; n8 is an integer from 1 to 5; n9 is an integer from 0 to (n8+3); R ^c15 is an organic group group).

Examples of organic groups related to R ^c13 and R ^c14 in the formula (c4a) are the same as those of R ^c7 . As R ^c13 , an alkyl group or a phenyl group is preferable. When R ^c13 is an alkyl group, the number of carbon atoms is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, particularly preferably 1 or more and 3 or less, and most preferably 1. That is, R ^{c13 is} most preferably a methyl group. When R ^c13 and R ^{c14 are} bonded to form a ring, the ring may be an aromatic ring or an aliphatic ring. Preferred examples of the group represented by formula (c4a) in which R ^c13 and R ^c14 form a ring include naphth-1-yl, 1,2,3,4-tetrahydronaphthalen-5-yl and the like. In the above formula (c4a), n6 is an integer of 0 or more and 4 or less, preferably 0 or 1, and more preferably 0.

In the above formula (c4b), R ^c15 is an organic group. As an organic group, the same group as the organic group demonstrated about R ^c7 is mentioned. Among the organic groups, an alkyl group is preferred. The alkyl group may be linear or branched. The number of carbon atoms of the alkyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, and particularly preferably 1 or more and 3 or less. As R ^c15 , preferably, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, etc. are exemplified, and among these, a methyl group is more preferable.

In the above formula (c4b), n8 is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 3 or less, and more preferably 1 or 2. In the above formula (c4b), n9 is 0 or more and (n8+3) or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0. In the above formula (c4b), n7 is an integer of 1 or more and 8 or less, preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1 or 2.

In formula (c4), R ^c11 is a hydrogen atom, an optionally substituted alkyl group having 1 to 11 carbon atoms, or an optionally substituted aryl group. As the substituent which may be possessed when R ^c11 is an alkyl group, a phenyl group, a naphthyl group, etc. are preferably mentioned. In addition, as the substituent which may be possessed when R ^c7 is an aryl group, preferably, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a halogen atom, etc. are mentioned.

In formula (c4), R ^{c11 is} preferably a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, phenyl, benzyl, methylphenyl, naphthyl, etc. Among these, methyl or phenyl is more preferred.

The compound represented by the formula (c4) can be used including the step of converting the oxime group (>C=N-OH) contained in the compound represented by the aforementioned formula (c5) into the oxime ester group represented by>C=NO-COR ^c11 Method of manufacturing. The R ^c11-based formula (c4) R ^c11 same.

The pair of oxime groups (>C=N-OH)>C=NO-COR The conversion of the oxime ester group represented by ^c11 can be performed by reacting the compound represented by the aforementioned formula (c5) with an acylating agent. Examples of the acylating agent that provides the acyl group represented by -COR ^c11 include acid anhydrides represented by (R ^c11 CO) ₂ O, or halides represented by R ^c11 COHal (Hal is a halogen atom).

Preferred specific examples of the compound represented by formula (c4) include the following PI-43 to PI-83.

Among these, in terms of sensitivity, it is preferable to use an oxime-based photopolymerization initiator, and more preferably selected from the oxime-based compound represented by the formula (c1), the oxime ester compound represented by the formula (c4), or a quince skeleton or carbohydrate At least one of the group consisting of an oxime ester compound having an azole group skeleton and a nitro group.

In the photosensitive resin composition, the content of the photopolymerization initiator (C) is not particularly limited within a range that does not interfere with the purpose of the present invention. With respect to the mass of the solid content of the photosensitive resin composition, the photopolymerization is initiated The content of the agent (C) is preferably 0.1% by mass or more and 20% by mass or less, more preferably 0.3% by mass or more and 10% by mass or less.

＜(D) Sensitizer＞ The photosensitive resin composition may contain the above-mentioned (C) photopolymerization initiator and (D) sensitizer. The photosensitive resin composition contains both (C) a photopolymerization initiator and (D) a sensitizer, so that it can be cured satisfactorily even if a light source with low irradiation energy such as LED exposure is used.

As the (D) sensitizer, a compound conventionally used for the purpose of sensitizing a photopolymerization initiator in a photosensitive resin composition can be used without particular limitation.

(D) The sensitizer is preferably a compound having one or more substituents selected from the group consisting of an alkoxy group, a substituted carbonyloxy group (carbonyloxy), and an oxo group (=O). As the compound having this substituent, a condensed polycyclic aromatic hydrocarbon compound or a condensed polycyclic aromatic heterocyclic compound is preferred. The condensed polycyclic aromatic hydrocarbon compound or the condensed polycyclic aromatic heterocyclic compound may have a substituent other than an alkoxy group, a substituted carbonyloxy group, and an oxo group (=O), as examples of such substituents Examples include alkyl groups having 1 to 20 carbon atoms, haloalkyl groups having 1 to 20 carbon atoms, alkoxyalkyl groups having 2 to 20 carbon atoms, and alkoxyalkyl groups having 2 to 20 carbon atoms. 2 or more and 20 or less aliphatic acyl groups, aromatic acyl groups having 7 or more and 11 or less carbon atoms (aroyl group), cyano groups, nitro groups, nitroso groups, halogen atoms, hydroxyl groups, and Sulfhydryl and so on.

The alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 or more and 20 or less, more preferably 1 or more and 12 or less, and particularly preferably 1 or more and 6 or less. Preferred examples of alkoxy include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, N-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, 2-ethylhexyl, n-nonyloxy, n-decyloxy, etc.

The substituted carbonyloxy group is a group represented by -O-CO-A ^d . A ^{d is} not particularly limited, as long as the (D) sensitizer has a desired sensitizing effect, and may be various organic groups. A is preferably an alkyl group having 1 or more and 20 or less carbon atoms, an aryl group having 6 or more and 10 or less carbon atoms, an alkoxy group having 1 or more and 20 carbon atoms, and an alkoxy group having 1 or more and 20 carbon atoms. 6 or more and 10 or less aryloxy groups.

The aryl group or aryloxy group may have one or more substituents. The type of the substituent is not particularly limited as long as it does not interfere with the purpose of the present invention. When the aryl group or the aryloxy group has multiple substituents, the multiple substituents may be the same or different. Preferred examples of the substituent include an alkoxy group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 10 carbon atoms. Alkyloxy groups, aryloxy groups having 6 to 10 carbon atoms, aliphatic acyl groups having 2 to 7 carbon atoms, and aromatic acyl groups having 7 to 11 carbon atoms (aryloxy) Amino), cyano, nitro, nitroso, halogen, hydroxyl, and mercapto groups.

When A ^d is an alkyl group or an alkoxy group, these groups may be linear or branched. Preferred examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl. Group, and 2-ethylhexyl, etc. Preferred examples of aryl groups include phenyl, o-tolyl, m-tolyl, p-tolyl, α-naphthyl, β-naphthyl, and the like. Preferred examples of alkoxy include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, N-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, 2-ethylhexyloxy and the like.

One or more substituted condensed polycyclic aromatic hydrocarbon compounds or condensed polycyclic aromatic heterocycles selected from the group consisting of alkoxy, substituted carbonyloxy, and oxo (=O) In the compound, the number of rings constituting the condensed ring is not particularly limited, as long as the desired sensitization effect can be obtained. The number of rings is preferably 2 or more, more preferably 3 or more, particularly preferably 3 or more and 6 or less, and most preferably 3 or 4. In addition, the condensed polycyclic aromatic hydrocarbon compound or the condensed polycyclic aromatic heterocyclic compound may have aromaticity, and the monocyclic ring forming the condensed polycyclic ring does not need to be an aromatic ring.

Preferred examples of the condensed polycyclic aromatic hydrocarbon compound or the condensed polycyclic ring contained in the condensed polycyclic aromatic heterocyclic compound include an acenaphthylene ring, a phenanthrene ring, an anthracene ring, a fused tetraphenyl ring, and a xylene ring. Ton ring, and thioxanthene ring. Among these rings, an anthracene ring, a fused tetraphenyl ring, and a thioxanthene ring are preferred.

(D) Specific examples of anthracene ring-containing compounds suitable for use as the sensitizer include 9,10-bis(acetoxy)anthracene, 9,10-bis(propionoxy)anthracene, 9,10-bis(acetoxy)anthracene, 10-bis(n-propylcarbonyloxy)anthracene, 9,10-bis(isopropylcarbonyloxy)anthracene, 9,10-bis(n-butylcarbonyloxy)anthracene, 9,10-bis(iso Butylcarbonyloxy)anthracene, 9,10-bis(n-pentylcarbonyloxy)anthracene, 9,10-bis(n-hexylcarbonyloxy)anthracene, 9,10-bis(n-heptylcarbonyloxy) Anthracene, 9,10-bis(2-ethylhexyloxy)anthracene, 9,10-bis(n-octylcarbonyloxy)anthracene, 9,10-bis(n-nonylcarbonyloxy)anthracene, 9 ,10-bis(n-decylcarbonyloxy)anthracene, 9,10-bis(benzyloxy)anthracene, 9,10-bis(4-methylbenzyloxy)anthracene, 9,10- Bis(2-naphthyloxy)anthracene, 2-methyl-9,10-bis(acetoxy)anthracene, 2-methyl-9,10-bis(propionoxy)anthracene, 2- Methyl-9,10-bis(n-propylcarbonyloxy)anthracene, 2-methyl-9,10-bis(isopropylcarbonyloxy)anthracene, 2-methyl-9,10-bis(n Butylcarbonyloxy)anthracene, 2-methyl-9,10-bis(isobutylcarbonyloxy)anthracene, 2-methyl-9,10-bis(n-pentylcarbonyloxy)anthracene, 2- Methyl-9,10-bis(n-hexylcarbonyloxy)anthracene, 2-methyl-9,10-bis(benzyloxy)anthracene, 2-methyl-9,10-bis(4-methyl Benzyloxy)anthracene, 2-methyl-9,10-bis(2-naphthyloxy)anthracene, 1-methyl-9,10-bis(acetoxy)anthracene, 1- Methyl-9,10-bis(propionyloxy)anthracene, 1-methyl-9,10-bis(n-propylcarbonyloxy)anthracene, 1-methyl-9,10-bis(isopropyl) Carbonyloxy)anthracene, 1-methyl-9,10-bis(n-butylcarbonyloxy)anthracene, 1-methyl-9,10-bis(isobutylcarbonyloxy)anthracene, 1-methyl -9,10-bis(n-pentylcarbonyloxy)anthracene, 1-methyl-9,10-bis(n-hexylcarbonyloxy)anthracene, 1-methyl-9,10-bis(benzyloxy) Base) anthracene, 1-methyl-9,10-bis(4-methylbenzyloxy)anthracene, 1-methyl-9,10-bis(2-naphthyloxy)anthracene, 2- Ethyl-9,10-bis(acetoxy)anthracene, 2-ethyl-9,10-bis(propionoxy)anthracene, 2-ethyl-9,10-bis(n-propylcarbonyloxy) Yl)anthracene, 2-ethyl-9,10-bis(isobutylcarbonyloxy)anthracene, 2-ethyl-9,10-bis(n-butylcarbonyloxy)anthracene, 2-ethyl-9 , 10-bis(isobutylcarbonyloxy)anthracene, 2-ethyl-9,10-bis(n-pentylcarbonyloxy)anthracene, 2-ethyl-9,10-bis(n-hexylcarbonyloxy) )Anthracene, 2-ethyl-9,10-bis(benzyloxy)anthracene, 2-ethyl-9,10-bis(4-ethyl-benzyloxy)anthracene, 2-ethyl -9,10-bis(2-naphthyloxy)anthracene, 1-ethyl-9,10-bis(acetoxy)anthracene, 1-ethyl -9,10-bis(propionyloxy)anthracene, 1-ethyl-9,10-bis(n-propylcarbonyloxy)anthracene, 1-ethyl-9,10-bis(isopropylcarbonyloxy) Yl)anthracene, 1-ethyl-9,10-bis(n-butylcarbonyloxy)anthracene, 1-ethyl-9,10-bis(isobutylcarbonyloxy)anthracene, 1-ethyl-9 , 10-bis(n-pentylcarbonyloxy)anthracene, 1-ethyl-9,10-bis(n-hexylcarbonyloxy)anthracene, 1-ethyl-9,10-bis(benzyloxy) Anthracene, 1-ethyl-9,10-bis(4-ethyl-benzyloxy)anthracene, 1-ethyl-9,10-bis(2-naphthyloxy)anthracene, 1-( Tert-butyl)-9,10-bis(n-propylcarbonyloxy)anthracene, 1-(tert-butyl)-9,10-bis(isopropylcarbonyloxy)anthracene, 1-(tert-butyl) -9,10-bis(n-butylcarbonyloxy)anthracene, 1-(tert-butyl)-9,10-bis(isobutylcarbonyloxy)anthracene, 1-(tert-butyl)-9,10 -Bis(n-pentylcarbonyloxy)anthracene, 1-(tert-butyl)-9,10-bis(n-hexylcarbonyloxy)anthracene, 1-(tert-butyl)-9,10-bis(benzyl) Anthracene, 1-(tert-butyl)-9,10-bis(4-(tert-butyl)-benzyloxy)anthracene, 1-(tert-butyl)-9,10-bis( 2-naphthyloxy)anthracene, 2-(tert-butyl)-9,10-bis(n-propylcarbonyloxy)anthracene, 2-(tert-butyl)-9,10-bis(isopropyl) Carbonyloxy)anthracene, 2-(tert-butyl)-9,10-bis(n-butylcarbonyloxy)anthracene, 2-(tert-butyl)-9,10-bis(isobutylcarbonyloxy) Anthracene, 2-(tert-butyl)-9,10-bis(n-pentylcarbonyloxy)anthracene, 2-(tert-butyl)-9,10-bis(n-hexylcarbonyloxy)anthracene, 2-( Tert-butyl)-9,10-bis(benzyloxy)anthracene, 2-(tert-butyl)-9,10-bis(4-(tert-butyl)-benzyloxy)anthracene, 2 -(Tert-butyl)-9,10-bis(2-naphthyloxy)anthracene, 2-pentyl-9,10-bis(n-propylcarbonyloxy)anthracene, 2-pentyl-9, 10-bis(isopropylcarbonyloxy)anthracene, 2-pentyl-9,10-bis(n-butylcarbonyloxy)anthracene, 2-pentyl-9,10-bis(isobutylcarbonyloxy) )Anthracene, 2-pentyl-9,10-bis(n-pentylcarbonyloxy)anthracene, 2-pentyl-9,10-bis(n-hexylcarbonyloxy)anthracene, 2-pentyl-9,10 -Bis(benzyloxy)anthracene, 2-pentyl-9,10-bis(4-(tert-butyl)-benzyloxy)anthracene, and 2-pentyl-9,10-bis( 2-naphthyloxy)anthracene and the like.

Or (D) the sensitizer is preferably an anthracene compound substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

Specific examples of anthracene compounds substituted by halogen atoms, which are preferred as the sensitizer (D), include 2-chloro-9,10-bis(acetoxy)anthracene, 2-chloro-9,10-bis (Propyloxy)anthracene, 2-chloro-9,10-bis(n-propylcarbonyloxy)anthracene, 2-chloro-9,10-bis(isopropylcarbonyloxy)anthracene, 2-chloro- 9,10-bis(n-butylcarbonyloxy)anthracene, 2-chloro-9,10-bis(isobutylcarbonyloxy)anthracene, 2-chloro-9,10-bis(n-pentylcarbonyloxy) )Anthracene, 2-chloro-9,10-bis(n-hexylcarbonyloxy)anthracene, 2-chloro-9,10-bis(benzyloxy)anthracene, 2-chloro-9,10-bis(4 -Methylbenzyloxy)anthracene, 2-chloro-9,10-bis(2-naphthyloxy)anthracene, 1-chloro-9,10-bis(acetoxy)anthracene, 1- Chloro-9,10-bis(propionyloxy)anthracene, 1-chloro-9,10-bis(n-propylcarbonyloxy)anthracene, 1-chloro-9,10-bis(isopropylcarbonyloxy) )Anthracene, 1-chloro-9,10-bis(n-butylcarbonyloxy)anthracene, 1-chloro-9,10-bis(isobutylcarbonyloxy)anthracene, 1-chloro-9,10-bis (N-pentylcarbonyloxy)anthracene, 1-chloro-9,10-bis(n-hexylcarbonyloxy)anthracene, 1-chloro-9,10-bis(benzyloxy)anthracene, 1-chloro- 9,10-bis(4-methylbenzyloxy)anthracene, 1-chloro-9,10-bis(2-naphthyloxy)anthracene, 2-fluoro-9,10-bis(acetyl Oxy)anthracene, 2-fluoro-9,10-bis(propionyloxy)anthracene, 2-fluoro-9,10-bis(n-propylcarbonyloxy)anthracene, 2-fluoro-9,10-bis (Isopropylcarbonyloxy)anthracene, 2-fluoro-9,10-bis(n-butylcarbonyloxy)anthracene, 2-fluoro-9,10-bis(isobutylcarbonyloxy)anthracene, 2- Fluoro-9,10-bis(n-pentylcarbonyloxy)anthracene, 2-fluoro-9,10-bis(n-hexylcarbonyloxy)anthracene, 2-fluoro-9,10-bis(benzyloxy) )Anthracene, 2-fluoro-9,10-bis(4-methylbenzyloxy)anthracene, 2-fluoro-9,10-bis(2-naphthyloxy)anthracene, 1-fluoro-9 , 10-bis(acetoxy)anthracene, 1-fluoro-9,10-bis(propionoxy)anthracene, 1-fluoro-9,10-bis(n-propylcarbonyloxy)anthracene, 1- Fluoro-9,10-bis(isopropylcarbonyloxy)anthracene, 1-fluoro-9,10-bis(n-butylcarbonyloxy)anthracene, 1-fluoro-9,10-bis(isobutylcarbonyl) (Oxy)anthracene, 1-fluoro-9,10-bis(n-pentylcarbonyloxy)anthracene, 1-fluoro-9,10-bis(n-hexylcarbonyloxy)anthracene, 1-fluoro-9,10- Bis(benzyloxy)anthracene, 1-fluoro-9,10-bis(4-methylbenzyloxy)anthracene, 1-fluoro-9,10-bis(2-naphthyloxy) Anthracene, 2-bromo-9,10-bis(acetoxy)anthracene, 2-bromo-9,10-bis(propionyloxy)anthracene, 2-bromo-9,10-bis(n-propylcarbonyl) Oxy)anthracene, 2-bromo-9,10-bis(isopropylcarbonyloxy)anthracene, 2-bromo-9,10-bis(n-butylcarbonyloxy) )Anthracene, 2-bromo-9,10-bis(isobutylcarbonyloxy)anthracene, 2-bromo-9,10-bis(n-pentylcarbonyloxy)anthracene, 2-bromo-9,10-bis (N-hexylcarbonyloxy)anthracene, 2-bromo-9,10-bis(benzyloxy)anthracene, 2-bromo-9,10-bis(4-methylbenzyloxy)anthracene, 2 -Bromo-9,10-bis(2-naphthanoyloxy)anthracene, 1-bromo-9,10-bis(acetoxy)anthracene, 1-bromo-9,10-bis(propionyloxy) )Anthracene, 1-bromo-9,10-bis(n-propylcarbonyloxy)anthracene, 1-bromo-9,10-bis(isopropylcarbonyloxy)anthracene, 1-bromo-9,10-bis (N-butylcarbonyloxy)anthracene, 1-bromo-9,10-bis(isobutylcarbonyloxy)anthracene, 1-bromo-9,10-bis(n-pentylcarbonyloxy)anthracene, 1- Bromo-9,10-bis(n-hexylcarbonyloxy)anthracene, 1-bromo-9,10-bis(benzyloxy)anthracene, 1-bromo-9,10-bis(4-methylbenzyl) (Athoxy)anthracene, 1-bromo-9,10-bis(2-naphthoxy)anthracene, etc.

In addition, (D) the sensitizer is preferably an anthracene compound substituted with an alkoxy group. (D) Specific examples of anthracene compounds substituted with alkoxy groups as sensitizers include 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-bis( N-propoxy)anthracene, 9,10-bis(n-butoxy)anthracene, 9,10-bis(n-pentoxy)anthracene, 9,10-bis(isopentoxyoxy)anthracene, 9,10 10-bis(n-hexyloxy)anthracene, 9,10-bis(n-heptyloxy)anthracene, 9,10-bis(n-octyloxy)anthracene, 9,10-bis(2-ethylhexyloxy) Anthracene, 9-methoxyanthracene, 9-ethoxyanthracene, 9-(n-propoxy)anthracene, 9-(n-butoxy)anthracene, 9-(n-pentoxy)anthracene, 9-(iso Pentyloxyoxy)anthracene, 9-(n-hexyloxy)anthracene, 9-(n-heptyloxy)anthracene, 9-(n-octyloxy)anthracene, 9-(2-ethylhexyloxy)anthracene, 2-methyl-9,10-dimethoxyanthracene, 2-methyl-9,10-diethoxyanthracene, 2-methyl-9,10-bis(n-propoxy)anthracene, 2- Methyl-9,10-bis(n-butoxy)anthracene, 2-methyl-9,10-bis(n-pentoxy)anthracene, 2-methyl-9,10-bis(isopentoxy) Yl)anthracene, 2-methyl-9,10-bis(n-hexyloxy)anthracene, 2-methyl-9,10-bis(n-heptyloxy)anthracene, 2-methyl-9,10-bis( N-octyloxy)anthracene, 2-methyl-9,10-bis(2-ethylhexyloxy)anthracene, 2-ethyl-9,10-dimethoxyanthracene, 2-ethyl-9, 10-diethoxyanthracene, 2-ethyl-9,10-bis(n-propoxy)anthracene, 2-ethyl-9,10-bis(n-butoxy)anthracene, 2-ethyl-9 ,10-bis(n-pentyloxy)anthracene, 2-ethyl-9,10-bis(isopentyloxy)anthracene, 2-ethyl-9,10-bis(n-hexyloxy)anthracene, 2 -Ethyl-9,10-bis(n-heptyloxy)anthracene, 2-ethyl-9,10-bis(n-octyloxy)anthracene, 2-ethyl-9,10-bis(2-ethyl) Hexyloxy)anthracene, 2-methyl-9-methoxyanthracene, 2-methyl-9-ethoxyanthracene, 2-methyl-9-(n-propyloxy)anthracene, 2-methyl -9-(n-butoxy)anthracene, 2-methyl-9-(n-pentoxy)anthracene, 2-methyl-9-(isopentoxyoxy)anthracene, 2-methyl-9- (N-hexyloxy)anthracene, 2-methyl-9-(n-heptyloxy)anthracene, 2-methyl-9-(n-octyloxy)anthracene, 2-methyl-9-(2-ethyl) Hexyloxy)anthracene, 2-ethyl-9-methoxyanthracene, 2-ethyl-9-ethoxyanthracene, 2-ethyl-9-(n-propoxy)anthracene, 2-ethyl- 9-(n-butoxy)anthracene, 2-ethyl-9-(n-pentoxy)anthracene, 2-ethyl-9-(isopentoxyoxy)anthracene, 2-ethyl-9-( N-hexyloxy)anthracene, 2-ethyl-9-(n-heptyloxy)anthracene, 2-ethyl-9-(n-octyloxy)anthracene, 2-ethyl-9-(2-ethylhexyloxy) Yl)anthracene, 2-chloro-9,10-dimethoxyanthracene, 2-chloro-9,10-diethoxyanthracene, 2-chloro-9,10-bis(n-propoxy)anthracene, 2 -Chlorine-9, 10-bis(n-butoxy)anthracene, 2-chloro-9,10-bis(n-pentyloxy)anthracene, 2-chloro-9,10-bis(isopentyloxy)anthracene, 2-chloro -9,10-bis(n-hexyloxy)anthracene, 2-chloro-9,10-bis(n-heptyloxy)anthracene, 2-chloro-9,10-bis(n-octyloxy)anthracene, 2-chloro -9,10-bis(2-ethylhexyloxy)anthracene, 2-bromo-9,10-dimethoxyanthracene, 2-bromo-9,10-diethoxyanthracene, 2-bromo-9 ,10-bis(n-propoxy)anthracene, 2-bromo-9,10-bis(n-butoxy)anthracene, 2-bromo-9,10-bis(n-pentoxy)anthracene, 2-bromo- 9,10-bis(isopentoxyoxy)anthracene, 2-bromo-9,10-bis(n-hexoxy)anthracene, 2-bromo-9,10-bis(n-heptyloxy)anthracene, 2- Bromo-9,10-bis(n-octyloxy)anthracene, 2-bromo-9,10-bis(2-ethylhexyloxy)anthracene, 2-chloro-9-methoxyanthracene, 2-chloro- 9-ethoxyanthracene, 2-chloro-9-(n-propoxy)anthracene, 2-chloro-9-(n-butoxy)anthracene, 2-chloro-9-(n-pentoxy)anthracene, 2 -Chloro-9-(isopentyloxyoxy)anthracene, 2-chloro-9-(n-hexyloxy)anthracene, 2-chloro-9-(n-heptyloxy)anthracene, 2-chloro-9-(normal Octyloxy)anthracene, 2-chloro-9-(2-ethylhexyloxy)anthracene, 2-bromo-9-methoxyanthracene, 2-bromo-9-ethoxyanthracene, 2-bromo-9 -(N-propoxy)anthracene, 2-bromo-9-(n-butoxy)anthracene, 2-bromo-9-(n-pentoxy)anthracene, 2-ethyl-9-(isopentoxy) Anthracene, 2-bromo-9-(n-hexyloxy)anthracene, 2-bromo-9-(n-heptyloxy)anthracene, 2-bromo-9-(n-octyloxy)anthracene, and 2-bromo- 9-(2-ethylhexyloxy)anthracene and the like.

Among the anthracene compounds described above, from the viewpoints of ease of production and performance as a (D) sensitizer, 9,10-bis(acetoxy)anthracene, 9,10-bis(propionyl anthracene) Oxy)anthracene, 9,10-bis(n-propylcarbonyloxy)anthracene, 9,10-bis(isopropylcarbonyloxy)anthracene, 9,10-bis(n-butylcarbonyloxy)anthracene, 9,10-bis(isobutylcarbonyloxy)anthracene, 9,10-bis(n-hexyloxy)anthracene, 9,10-bis(n-heptyloxy)anthracene, 9,10-bis(n-octyloxy)anthracene ((2-ethylhexyloxy)anthracene, 9,10-bis(2-ethylhexoxy)anthracene, 9,10-bis(n-nonanoyloxy)anthracene, 9,10-diethoxyanthracene, 9,10 -Dipropoxyanthracene, and 9,10-dibutoxyanthracene.

Specific examples of compounds containing fused tetraphenyl ring suitable for use as (D) sensitizers include: 2-Methyl-5,11-dioxo-6,12-bis(acetoxy) fused tetrabenzene ( naphthacene), 2-methyl-5,11-dioxo-6,12-bis(propionyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis( N-propylcarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(isopropylcarbonyloxy) fused tetrabenzene, 2-methyl-5,11- Dioxo-6,12-bis(n-butylcarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(isobutylcarbonyloxy) fused tetrabenzene , 2-Methyl-5,11-dioxo-6,12-bis(n-pentylcarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis( N-hexylcarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(n-heptylcarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-di Oxo-6,12-bis(acetoxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(propionoxy) fused tetrabenzene, 2-ethyl -5,11-dioxo-6,12-bis(n-propylcarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(isopropylcarbonyloxy) Group) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(n-butylcarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6 ,12-bis(isobutylcarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(n-pentylcarbonyloxy) fused tetrabenzene, 2-ethyl -5,11-dioxo-6,12-bis(n-hexylcarbonyloxy) fused tetrabenzene, and 2-ethyl-5,11-dioxo-6,12-bis(n-heptylcarbonyloxy) Group) fused tetrabenzene and other alkylcarbonyloxy substituted fused tetrabenzene compounds; 2-Methyl-5,11-dioxo-6,12-bis(benzyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(o-toluene O-toluoyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(m-toluoyloxy) fused tetrabenzene, 2-methyl-5 ,11-dioxo-6,12-bis(p-tolyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(α-naphthoxy) ) Fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(β-naphthoxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6 ,12-bis(benzyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(o-tolyloxy) fused tetrabenzene, 2-ethyl- 5,11-dioxo-6,12-bis(m-tolyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(p-tolyloxy) ) Fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(α-naphthoxy) fused tetrabenzene, and 2-ethyl-5,11-dioxo- 6,12-bis(β-naphthoxy) fused tetrabenzene and other aryloxy substituted fused tetrabenzene compounds; 2-Methyl-5,11-dioxo-6,12-bis(methoxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(ethyl Oxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(n-propyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11 -Dioxo-6,12-bis(isopropyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(n-butoxycarbonyloxy) ) Fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(isobutoxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6 ,12-bis(n-pentyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(n-hexyloxycarbonyloxy) fused tetrabenzene, 2-methyl Group-5,11-dioxo-6,12-bis(n-heptyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(n-octyloxy) Carbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(methoxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-diox -6,12-bis(ethoxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(n-propoxycarbonyloxy) fused tetrabenzene, 2-Ethyl-5,11-dioxo-6,12-bis(isopropoxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis( N-butoxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(isobutoxycarbonyloxy) fused tetrabenzene, 2-ethyl-5, 11-dioxo-6,12-bis(n-pentyloxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(n-hexyloxycarbonyloxy) Fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(n-heptyloxycarbonyloxy) fused tetrabenzene, and 2-ethyl-5,11-dioxo-6 ,12-bis(n-octyloxycarbonyloxy) fused tetraphenyl and other alkoxycarbonyloxy substituted fused tetraphenyl compounds; and, 2-methyl-5,11-dioxo-6,12-bis(phenoxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(ortho Tolyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(m-tolyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11 -Dioxo-6,12-bis(p-tolyloxycarbonyloxy) fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(α-naphthyloxycarbonyloxy) ) Fused tetrabenzene, 2-methyl-5,11-dioxo-6,12-bis(β-naphthyloxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo- 6,12-bis(phenoxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(o-tolyloxycarbonyloxy) fused tetrabenzene, 2- Ethyl-5,11-dioxo-6,12-bis(m-tolyloxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(p-toluene Oxycarbonyloxy) fused tetrabenzene, 2-ethyl-5,11-dioxo-6,12-bis(α-naphthyloxycarbonyloxy) fused tetrabenzene, and 2-ethyl-5, 11-dioxo-6,12-bis(β-naphthyloxycarbonyloxy) fused tetrabenzene and other aryloxycarbonyloxy substituted fused tetrabenzene compounds.

Among the above-mentioned compounds containing fused tetraphenyl ring, 5,11-dioxo-6,12-bis(methoxycarbonyloxy) fused tetrabenzene, 5,11-dioxo-6,12 -Bis(ethoxycarbonyloxy) fused tetrabenzene, 5,11-dioxo-6,12-bis(isopropoxycarbonyloxy) fused tetrabenzene, 5,11-dioxo-6, 12-bis(isobutoxycarbonyloxy) fused tetrabenzene, 5,11-dioxo-6,12-bis(n-butylcarbonyloxy) fused tetrabenzene, 5,11-dioxo-6 ,12-bis(n-pentylcarbonyloxy) fused tetrabenzene, 5,11-dioxo-6,12-bis(n-heptanoyloxy) fused tetrabenzene. From the viewpoint of compatibility with (A) the photopolymerizable compound, 5,11-dioxo-6,12-bis(isopropoxycarbonyloxy) fused tetrabenzene, 5,11-di Oxo-6,12-bis(isobutoxycarbonyloxy) fused tetrabenzene, 5,11-dioxo-6,12-bis(n-butoxy) fused tetrabenzene, 5,11-bis Oxo-6,12-bis(n-pentyloxy) fused tetrabenzene, 5,11-dioxo-6,12-bis(heptanoyloxy) fused tetrabenzene.

(D) Specific examples of thioxanthene ring-containing compounds suitable for use as a sensitizer include thioxanthene-9-one, 2-methyl-9H-thioxanthene-9-one, and 2-isopropyl -9H-thioxanthene-9-one, 1,4-dimethylthioxanthene-9-one, and 3-methyl-9-oxo-9H-thioxanthene-2-yl acetate, etc.

The content of the sensitizer of the component (D) is preferably 5 parts by mass or more and 60 parts by mass or less relative to the total 100 parts by mass of the (C) photopolymerization initiator components in the photosensitive resin composition, more preferably It is 15 parts by mass or more and 50 parts by mass or less. When the photosensitive resin composition contains a sensitizer in the above-mentioned range, the curing reaction by exposure proceeds uniformly, and it is easy to form a patterned cured film with particularly good edge angles.

＜(E) Colorant＞ The photosensitive resin composition may be a substantially colorless and transparent composition without containing a colorant depending on its use. On the other hand, for other applications, the photosensitive resin composition may further contain (D) a colorant. Since the photosensitive resin composition contains, for example, a black pigment as the coloring agent of the component (D), it can be suitably used for forming a black matrix (or black bank) in a color filter of a display device, for example. ))the use of. In addition, a colored coloring agent can be suitably used, for example, for the purpose of forming a color filter of a display device.

The (D) colorant contained in the photosensitive resin composition is not particularly limited. When the colorant is used as the light-shielding agent, it is preferable to use a black pigment as the light-shielding agent. Examples of black pigments include carbon black, titanium black, copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, silver and other metal oxides, composite oxides, metal sulfides, metal sulfates, or metal carbonates. Various pigments such as salt (either organic or inorganic). Among these, it is preferable to use carbon black having high light-shielding properties.

As carbon black, channel black can be used , Furnace black, thermal black, lamp black, and other known carbon blacks, it is preferable to use channel black having excellent light-shielding properties. In addition, resin-coated carbon black can also be used.

Carbon black coated with resin has lower conductivity than carbon black without resin coating. Therefore, when used as a black matrix of a liquid crystal display element such as a liquid crystal display, it can produce less current leakage and high reliability. Its low power consumption display. Examples of black pigments other than carbon black include (D2a) perylene pigments and (D2b) endoamide pigments. These pigments can be used in combination of two or more kinds.

The (D2a) perylene-based pigment is not particularly limited, as long as it is formed of a compound having a perylene skeleton and exhibits a black color. As specific examples of (D2a) perylene pigments, perylene pigments represented by the following formula (d-1), perylene pigments represented by the following formula (d-2), and the following formula (d-3) ) Represents the perylene pigment. Among commercially available products, it is preferable to use product names K0084, K0086, and pigment black 21, 30, 31, 32, 33, and 34 manufactured by BASF Corporation as (D2a) perylene pigments.

式(d-1)中，R^d1 及R^d2 各自獨立地表示碳原子數為1以上且3以下的伸烷基，R^d3 及R^d4 各自獨立地表示氫原子、羥基、甲氧基、或乙醯基。

In the formula ^(d1), R d1 and R ^d2 each independently represent a number of 1 or more carbon atoms and 3 or less alkylene group, R ^d3 and R ^d4 each independently represents a hydrogen atom, a hydroxyl group, a methoxy group, or Acetyl.

式(d-2)中，R^d5 及R^d6 各自獨立地表示碳原子數為1以上且7以下的伸烷基。

In the formula (d-2), ^Rd5 and ^Rd6 each independently represent an alkylene group having 1 or more and 7 or less carbon atoms.

式(d-3)中，R^d7 及R^d8 各自獨立地為氫原子、碳原子數為1以上且22以下的烷基，也可包含N、O、S、或P的雜原子。R^d7 及R^d8 為烷基時，該烷基可為直鏈狀，也可為支鏈狀。

In formula (d-3), ^Rd7 and ^Rd8 are each independently a hydrogen atom, an alkyl group having 1 or more and 22 or less carbon atoms, and may include N, O, S, or P heteroatoms. When R ^d7 and R ^d8 are an alkyl group, the alkyl group may be linear or branched.

For the compound represented by the above formula (d-1), the compound represented by the formula (d-2), and the compound represented by the formula (d-3), for example, Japanese Patent Application Publication No. 62-1753 and Japanese Patent Publication No. 63- Synthesized by the method described in Bulletin No. 26784. That is, perylene-3,5,9,10-tetracarboxylic acid or its dianhydride and amines are used as raw materials, and a heating reaction is performed in water or an organic solvent. Then, the obtained crude product is reprecipitated in sulfuric acid, or recrystallized in water, an organic solvent, or a mixed solvent of these, thereby obtaining the target product.

In order to disperse the (D2a) perylene-based pigment in the photosensitive resin composition well and form a cured film with low transmittance to light in a wide wavelength range, the volume average particle diameter of the perylene-based pigment is preferably 10 nm or more and 1000 nm or less, more preferably 10 nm or more and 500 nm or less, particularly preferably 10 nm or more and 200 nm or less. In addition, when the volume particle diameter of the perylene-based pigment is within the above range, it is easy to stably form a cured film having a low arithmetic average roughness Ra and a smooth surface.

As (D2b) endoamide-based pigments, for example, compounds represented by the following formula (d-4) can be given.

In formula (d-4), X ^d represents a double bond, as geometric isomers, each independently is an E form or a Z form, and R ^d9 each independently represents a hydrogen atom, a methyl group, a nitro group, a methoxy group, and a bromine atom , A chlorine atom, a fluorine atom, a carboxyl group, or a sulfo group, R ^d10 each independently represents a hydrogen atom, a methyl group, or a phenyl group, and R ^d11 each independently represents a hydrogen atom, a methyl group, or a chlorine atom. The compound represented by formula (d-4) may be used alone or in combination of two or more kinds. From the viewpoint of easy production of the compound represented by formula (d-4), R ^{d9 is} preferably bonded to the 6-position of the indolinone ring, and R ^{d11 is} preferably 4 bonded to the indolinone ring. Bit. From the same viewpoint, R ^d9 , R ^d10 , and R ^{d11 are} preferably hydrogen atoms. The compound represented by formula (d-4) has EE form, ZZ form, and EZ form as geometric isomers, but it may be a single compound of any of these, or a mixture of these geometric isomers. The compound represented by formula (d-4) can be produced, for example, by the method described in International Publication No. 2000/24736 and International Publication No. 2010/081624.

In order to disperse the internal amine-based pigment in the photosensitive resin composition well, the volume average particle diameter of the internal amine-based pigment is preferably 10 nm or more and 1000 nm or less.

In addition, in order to adjust the hue of black pigments such as carbon black, the following organic pigments can be appropriately added as auxiliary pigments. In addition, instead of using black pigments such as carbon black, a plurality of organic pigments as shown below may be combined, for example, color materials of three primary colors are mixed to form black.

As the organic pigment, for example, it is preferable to use a compound classified as a pigment in the Dyestuff Index (CI; issued by The Society of Dyers and Colourists). Specifically, it is preferable to use a compound with a dye as described below. Index (CI) number of pigments.

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

Examples of orange pigments that can be suitably used include CI Pigment Orange 1 (hereinafter, "CI Pigment Orange", and only the number is also described), 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 55, 59, 61, 63, 64, 71, and 73.

Examples of purple pigments that can be suitably used include CI Pigment Violet 1 (hereinafter, "CI Pigment Violet" is also described with only a number), 19, 23, 29, 30, 32, 36, 37, 38, 39 , 40, and 50.

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

Examples of blue pigments that can be suitably used include CI Pigment Blue 1 (hereinafter, "CI Pigment Blue" is also described with only the number), 2, 15, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, and 66.

As examples of pigments of hue other than the above that can be suitably used, green pigments such as CI Pigment Green 7, CI Pigment Green 36, CI Pigment Green 37, CI Pigment Brown 23, CI Pigment Brown 25, CI Pigment Brown pigments such as Brown 26, CI Pigment Brown 28, CI Pigment Black 1, CI Pigment Black 7 and other black pigments.

In order to uniformly disperse the above-mentioned colorant in the photosensitive resin composition, a dispersant may be further used. As such a dispersant, it is preferable to use polyethyleneimine-based, polyurethane resin-based, and acrylic resin-based polymer dispersants. In particular, when carbon black is used as a colorant, it is preferable to use an acrylic resin-based dispersant as the dispersant.

In addition, inorganic pigments and organic pigments can be used alone or in combination of two or more. When used in combination, it is preferably 10 parts by mass to 80 parts by mass relative to 100 parts by mass of the total amount of inorganic pigments and organic pigments. The organic pigment is used in the range, and it is more preferable to use the organic pigment in the range of 20 parts by mass or more and 40 parts by mass or less.

The amount of the coloring agent used in the photosensitive resin composition may be appropriately determined according to the use of the photosensitive resin composition. For example, relative to 100 parts by mass of the total mass of components other than the solvent in the photosensitive resin composition , Preferably 1 part by mass or more and 50 parts by mass or less, more preferably 5 parts by mass or more and 30 parts by mass or less. By setting it in the above range, a black matrix or each colored layer can be formed in a desired pattern, which is preferable.

In particular, when a photosensitive resin composition is used to form a black matrix (or black bank), it is preferable to adjust the amount of the light-shielding agent in the photosensitive resin composition so that the OD value per 1 μm of the black matrix becomes 0.1 or more . When the OD value of the film per 1 μm of the black matrix is 0.1 or more, sufficient display contrast can be obtained when used for the black matrix of a display device.

The colorant is preferably added to the photosensitive resin composition after preparing a dispersion liquid dispersed at an appropriate concentration using a dispersant.

＜Solvent (S)＞ The photosensitive resin composition may contain or not contain the solvent (S). When the solvent (S) is included, as the solvent (S), for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol mono-n-butyl ether, di Ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol Monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl (Poly)alkylene glycol monoalkyl ethers such as dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc.; ethylene glycol monomethyl ether acetate, Ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether ethyl Acid esters and other (poly) alkylene glycol monoalkyl ether acetates; diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, etc. Ethers; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; alkyl lactates such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; 2- Ethyl hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate , Ethoxy ethyl acetate, hydroxy ethyl acetate, 2-hydroxy-3-methylbutyrate methyl ester, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methyl propionate Oxybutyl ester, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, N-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, 2-oxo Other esters such as ethyl butyrate; aromatic hydrocarbons such as toluene and xylene; N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amines Wait. These solvents may be used alone or in combination of two or more kinds.

The photosensitive resin composition can be prepared by dispersing and dissolving each component in a solvent. If the aforementioned (A) component is liquid, the solvent may not be used. When a solvent is included, as a solvent that can be used in the photosensitive resin composition, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol mono-n-butyl Base ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, Triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, two Propylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether and other (poly)alkylene glycol monoalkyl ethers; ethylene glycol monomethyl ether Acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol mono (Poly) alkylene glycol monoalkyl ether acetates such as ethyl ether acetate; diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether , Tetrahydrofuran and other ethers; methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone and other ketones; 2-hydroxypropionic acid methyl ester, 2-hydroxypropionic acid ethyl ester and other alkyl lactate Class; Ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, ethyl ethoxy acetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutyrate, 3-methyl-3-methoxybutyl acetate, 3-methyl propionate -3-Methoxybutyl, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isoamyl acetate, n-butyl propionate, butyl Ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, Other esters such as ethyl 2-oxobutyrate; aromatic hydrocarbons such as toluene and xylene; N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide And other amides. These solvents may be used alone or in combination of two or more kinds.

The solvent (S) may be appropriately determined according to the use of the photosensitive resin composition, and as an example, the solid content concentration in the photosensitive resin composition may be appropriately adjusted within the range of 1% by mass to 50% by mass.

＜(E) Hydrophobic agent＞ The photosensitive resin composition may further contain a hydrophobic agent. For example, in order to utilize hydrophobicity or even liquid repellency in areas such as lithographic printing plates and nozzle surfaces of inkjet heads to greatly improve printing quality, it is desirable to form a hydrophobic film having a pattern shape from a photosensitive resin composition.

式(1)中，X表示氫原子、氟原子、或三氟甲基，R^f 表示可具有醚性氧原子之至少1個氫原子被氟原子取代之碳原子數為20以下的氟烷基；或氟原子。 式(2)中，R^e1 、R^e2 、R^e3 及R^e4 獨立地表示氫原子、烷基、環烷基、或芳基，R^e5 表示氫原子或碳原子數為1～10的有機基團，n表示1～200的整數。 另外，可例舉包含具有含氟基團的水解性矽烷化合物及具有陽離子聚合性基團的水解性矽烷化合物的縮合物。作為一例，例如，可舉出下式表示的化合物等。

(式中，n為0以上且7以下的整數)。 n超過上述範圍時，感光性樹脂組合物中的相溶性下降，變得難以向被覆膜整體均勻地賦予疏水性。(E) The hydrophobizing agent is not particularly limited, but preferably contains a compound having fluorine. For example, as the hydrophobizing agent, a perfluoroalkyl composition having cationic polymerizability and a perfluoropolyether composition having cationic polymerizability can be mentioned. Specifically, it is preferably a composition containing an ink repellent agent having a side chain containing a group represented by the following formula (E-1) or a group represented by the following formula (E-2).

In the formula (1), X represents a hydrogen atom, a fluorine atom, or a trifluoromethyl group, and R ^f represents a fluoroalkyl group with at least one hydrogen atom substituted by a fluorine atom, which may have an etheric oxygen atom, with a carbon number of 20 or less ; Or fluorine atom. In formula (2), R ^e1 , R ^e2 , R ^e3 and R ^e4 independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and R ^e5 represents a hydrogen atom or an organic group having 1 to 10 carbon atoms Group, n represents an integer of 1 to 200. In addition, a condensate containing a hydrolyzable silane compound having a fluorine-containing group and a hydrolyzable silane compound having a cationic polymerizable group can be mentioned. As an example, for example, a compound represented by the following formula and the like can be given.

(In the formula, n is an integer of 0 or more and 7 or less). When n exceeds the above-mentioned range, the compatibility in the photosensitive resin composition decreases, and it becomes difficult to uniformly impart hydrophobicity to the entire coating film.

In the photosensitive resin composition, the blending ratio of the hydrophobic agent is not particularly limited, and it is preferably 20 parts by mass or less, more preferably 0.05 with respect to 100 parts by mass of the total mass of components other than the solvent in the photosensitive resin composition Parts by mass or more and 10 parts by mass or less. When the amount of the hydrophobizing agent in the above range is used, the alkali-soluble resin (A) and the hydrophobizing agent are well compatible, and it is easy to achieve good hardness of the cured film, good hydrophobicity of the cured film, and good balance. Good edge angle characteristics of the cured film.

＜Other ingredients＞ The photosensitive resin composition may contain other various additives other than this if necessary. Specifically, dispersion aids, fillers, fillers, adhesion promoters, antioxidants, ultraviolet absorbers, anti-agglomeration agents, thermal polymerization inhibitors, defoamers, surfactants, etc. may be mentioned.

Examples of the thermal polymerization inhibitor that can be used in the photosensitive resin composition include hydroquinone, hydroquinone monoethyl ether, and the like. In addition, as the antifoaming agent, a silicone-based compound, a fluorine-based compound, etc. may be exemplified, respectively, and as the surfactant, an anionic, cationic, nonionic, or the like compound may be exemplified.

[Preparation method of photosensitive resin composition] The photosensitive resin composition can be prepared by mixing all the above-mentioned components using a blender. Moreover, when the prepared photosensitive resin composition does not contain insoluble components, such as a pigment, in order to make the photosensitive resin composition uniform, it can filter using a filter.

≪Curing film formation method≫ The manufacturing method of the cured film includes the following steps: a step of applying a photosensitive resin composition to a substrate to form a photosensitive resin layer (hereinafter, also simply referred to as "resin layer forming step"), and placing the above-mentioned resin layer in position The step of selectively exposing (hereinafter, also referred to as "exposure step") and the step of developing the exposed photosensitive resin layer with a developer to form a pattern (hereinafter, also referred to as "developing step"). .

The substrate (substrate or support) can be selected according to various applications, such as quartz, glass, optical film, ceramic material, vapor-deposited film, magnetic film, reflective film, metal substrates such as Ni, Cu, Cr, Fe, paper, SOG (Spin On Glass), polyester film, polycarbonate film, polyimide film and other polymer substrates, TFT array substrates, PDP electrode plates, glass, transparent plastic substrates, ITO, metals, etc. Non-restricted substrates, such as flexible substrates, insulating substrates, silicon, silicon nitride, polycrystalline silicon, silicon oxide, amorphous silicon and other semiconductor substrates. In addition, for example, when a laminated structure is formed on a substrate, any layer that has been formed on the substrate and becomes a lower structure is also included in the concept as a base material to which the photosensitive resin layer is applied. In addition, the shape of the substrate is also not particularly limited, and may be a plate shape or a roll shape. The substrate may further have irregularities on the surface, for example, by various patterns. In addition, as the aforementioned substrate, a translucent or non-translucent substrate can be selected.

First, in the resin layer forming step, for example, a roller coater, a reverse coater, a bar coater, etc. contact transfer type coating device, spin coater (rotary coating device), dispenser (dispenser) , Inkjet, spray, screen printing, curtain flow coater (curtain flow coater) and other non-contact coating devices, apply the photosensitive resin composition to the substrate to be cured, and dry (pre- Baking) The solvent is removed to form a photosensitive resin layer.

The thickness of the photosensitive resin layer is not particularly limited, but is preferably 0.05 μm or more, more preferably 1 μm or more, still more preferably 7 μm or more, and particularly preferably 10 μm or more. The upper limit is not particularly limited. For example, it is 50 μm or less, preferably 20 μm or less. As described above, for the photosensitive resin composition, curing can be promoted even in the portion where the active energy does not directly reach during exposure. Therefore, for example, a photosensitive resin layer having a thickness of 1 μm or more and 15 μm or less is formed. In the aspect, even in the vicinity of the substrate side located farther from the exposure side, sufficient curing can be performed.

In addition, for the liquid droplets accumulated on the substrate, the photosensitive resin composition filled in the recesses of the substrate with irregularities, or the photosensitive resin composition filled in the recesses of the mold, it is for convenience. It is called "photosensitive resin layer".

Next, the formed photosensitive resin layer can be cured by exposure. The exposure method is not particularly limited, as long as it is a method capable of curing the photosensitive resin composition, and if necessary, it may be combined with heat treatment.

For exposure, the light source is not particularly limited, and examples thereof include high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, carbon arc lamps, and LEDs. Such a light source can be used to irradiate the coating film with ArF excimer laser, KrF excimer laser, F ₂ excimer laser, extreme ultraviolet (EUV), vacuum ultraviolet (VUV), electron beam, X-ray, soft X-ray, g-ray , I-ray, h-ray, j-ray, k-ray and other radiation or electromagnetic waves to expose the coating film. The exposure of the coating film can be performed in a position selective manner through a negative mask. The exposure amount varies depending on the composition of the curable composition. For example, it is preferably 10 mJ/cm ² or more and 2000 mJ/cm ² or less, more preferably 100 mJ/cm ² or more and 1500 mJ/cm ² or less, and still more preferably 200 mJ /cm ² or more and 1200 mJ/cm ² or less. The exposure illuminance varies depending on the composition of the photosensitive resin composition, and is preferably in the range of 1 mW/cm ² or more and 50 mW/cm ² or less. The temperature during heating is not particularly limited, but is preferably 180°C or higher and 280°C or lower, more preferably 200°C or higher and 260°C or lower, and particularly preferably 220°C or higher and 250°C or lower. The heating time is typically preferably 1 minute or more and 60 minutes or less, more preferably 10 minutes or more and 50 minutes or less, and particularly preferably 20 minutes or more and 40 minutes or less.

The step of curing the photosensitive resin layer is performed by position-selective exposure, and the photosensitive resin layer that has been exposed in a position-selective manner is developed to obtain a patterned cured film. The aforementioned curable composition is unlikely to be excessively dissolved in a developer after exposure. Therefore, by using the aforementioned curable composition, it is possible to form a cured product patterned in a good shape in which the exposed part becomes a convex part and the unexposed part becomes a concave part.

In the developing step, by developing the exposed coating film with a developing solution, a cured product patterned in a desired shape can be formed. The development method is not particularly limited, and a dipping method, a spray method, a puddle method, a dynamic dispense method, etc. can be used. As a specific example of a developer containing an organic solvent, alcohol solvents such as PE (propylene glycol monomethyl ether) or glycol ether solvents, ether solvents such as tetrahydrofuran, ester solvents such as butyl acetate, acetone, methyl ether, etc. Ketone-based solvents such as pentyl ketone. Specific examples of alkali developable solutions include organic developing solutions such as monoethanolamine, diethanolamine, and triethanolamine, and aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and quaternary ammonium salts.

Furthermore, if necessary, the cured product after exposure or the patterned cured product after development can be post-baked, and further heated and cured. The temperature of the post-baking is preferably 150°C or higher and 270°C or lower.

≪Cured product≫ The cured product is formed by curing the aforementioned curable composition. Therefore, the cured product can also have a good fine pattern, and the heat resistance and transparency are also good. When the cured product is a cured film, the thickness of the cured film is not particularly limited, but it is preferably 0.05 μm or more and 50 μm or less. In addition, since the patterned cured film is formed of the above-mentioned cured product, it can have the above-mentioned good fine pattern.

The aforementioned cured product can be used for the purpose of a bank formed in the form of partitioning the surface of the substrate into a plurality of regions for forming dots. It should be noted that the dot represents the smallest area in the optical element where light can be modulated. In organic EL elements, quantum dot displays, TFT arrays, and thin-film solar cells, in the case of black and white display, 1 dot = 1 picture element, in the case of color display, for example, 3 dots (R (red) , G (green), B (blue), etc.) = 1 picture element.

The aforementioned cured product is formed of a photosensitive resin composition with excellent patterning characteristics, and therefore, when used for optical elements (especially organic EL elements produced by inkjet methods, quantum dot displays, TFT arrays, or thin-film solar cells) , Ink can be evenly applied to the openings to form dots with high precision.

When the aforementioned cured product is used for bank applications, the width of the bank is preferably, for example, 100 μm or less, and particularly preferably 20 μm or less. In addition, the distance between adjacent banks (the width of the pattern) is preferably 300 μm or less, particularly preferably 100 μm or less. The height of the bank is preferably 0.05 to 50 μm, particularly preferably 0.2 to 20 μm.

Hereinafter, an example in which the above-mentioned cured product is used for bank applications and the inkjet method is used to form dots in the opening of the bank in order to obtain an optical element will be described, but it is not limited to this.

A method of manufacturing a quantum dot display as an example of an optical element using banks formed on a substrate (for example, forming a grid-like bank) will be described.

Here, the bank on the substrate is formed so that the opening portion matches the dot pattern of the quantum dot display to be manufactured.

In addition, the substrate is a film in which a translucent electrode such as ITO is formed on a translucent substrate such as glass by a sputtering method or the like. The translucent electrode can be patterned if necessary.

In the opening surrounded by the bank, ink is dropped from the inkjet head, and a specific amount of ink is injected into the opening. As the ink, it is possible to appropriately select the known inks for quantum dot displays according to the function of the dots (for example, hole injection layer, hole transport layer, quantum dot layer, hole barrier layer, and electron injection are used. Layer materials such as ink, etc.) are used.

Next, depending on the type of ink used, for example, in order to remove or solidify the solvent, treatments such as drying and/or heating are performed to form a desired dot layer adjacent to the bank. Then, a reflective electrode such as aluminum or a translucent electrode such as ITO is formed by a vapor deposition method or the like to obtain a quantum dot display.

In addition, the quantum dot display may be a blue light conversion type quantum dot display. In this case, on a translucent substrate such as glass, a flat grid-like bank is formed along the contour of each point. Next, in the opening for dot formation, a nanoparticle solution that converts blue light into green light, a nanoparticle solution that converts blue light into red light, and blue color ink as needed are applied by inkjet method. Dry and make a module. By using a light source that develops blue as a backlight, and using the aforementioned module as a substitute for a color filter, a display with excellent color reproducibility can be obtained.

By using the bank formed by the cured product of the present invention, the ink can be uniformly applied to the openings partitioned by the cured product (bank) with high pattern accuracy during the manufacturing process, thereby obtaining Optical elements (organic EL elements, quantum dot displays, TFT arrays, or thin-film solar cells) that are formed with high precision.

Example

Hereinafter, examples are shown to further specifically illustrate the present invention, but the scope of the present invention is not limited by these examples.

In Examples 1 to 23 and Comparative Examples 1 to 5 shown below, as the alkali-soluble resin (A), resins (a-1-1) and (a- Any one of 1-2) and (a-2-1).

First, in a 500ml four-necked bottle, 235g of bisphenol phenolic epoxy resin (epoxy equivalent 235), 110mg of tetramethylammonium chloride, and 100mg of 2,6-di-tert-butyl-4-methylphenol , And 72.0 g of acrylic acid, while blowing air into it at a rate of 25 ml/min, heating and dissolving at 90°C to 100°C. Next, the temperature is gradually raised while the solution remains cloudy and heated to 120°C to completely dissolve it. Here, the solution gradually becomes transparent and viscous, and stirring is continued while maintaining this state. During this period, the acid value is measured, and heating and stirring are continued until the acid value becomes less than 1.0 mgKOH/g. It takes 12 hours to reach the target acid value. Then, it is cooled to room temperature to obtain a bisphenol phenolic epoxy acrylate.

Next, 600 g of 3-methoxybutyl acetate was added to 307.0 g of the bisphenol phenolic epoxy acrylate obtained above, and after dissolving it, 80.5 g of biphenyltetracarboxylic dianhydride and brominated Tetraethylammonium 1g, the temperature is gradually increased, and the reaction is carried out at 110°C to 115°C for 4 hours. After confirming that the acid anhydride disappeared, 38.0 g of 1,2,3,6-tetrahydrophthalic anhydride was mixed and reacted at 90°C for 6 hours to obtain resin (a-1-1) (weight average molecular weight: 3400). The disappearance of acid anhydride was confirmed by IR spectroscopy.

Except that 80.5 g of biphenyltetracarboxylic dianhydride in the production of the above resin (a-1-1) was changed to 59.7 g of pyromellitic dianhydride, it was the same as the production of resin (a-1-1) Operate carefully to obtain resin (a-1-2). The weight average molecular weight is 2500.

(丙烯酸系樹脂a-2-1的上述式中，各單元之右下方的數位表示鹼可溶性樹脂中之各單元的含量(質量%))。 上述鹼可溶性樹脂的重均分子量為7000。

(In the above formula of acrylic resin a-2-1, the digits on the lower right of each unit represent the content (mass %) of each unit in the alkali-soluble resin). The weight average molecular weight of the alkali-soluble resin is 7,000.

In addition, in each Example and Comparative Example, dipentaerythritol hexaacrylate (b-2-1) was used as the crosslinking agent (B) as the polyfunctional (meth)acrylic monomer (B2).

In addition, with regard to the monofunctional (meth)acrylic monomers as the crosslinking agent (B), the following formulae (b-1-1) to (b-1-4) were used in the blending amounts shown in Table 1. The compound shown.

In each Example and Comparative Example, as the photopolymerization initiator (C), the compounds c1 to c2 represented by the following formulae were used.

In addition, in each of the Examples and Comparative Examples, 2-isopropylthioxanthone (compound d1: 2-isopropyl-9H-thioxanthone-9-one) was used as the sensitizer (D).

In addition, in each of Examples 1 to 18, 22 to 26, and Comparative Examples 1 to 4, carbon was used in the blending amount shown in Table 1 (the blending amount of only the colorant component in each dispersion liquid converted into a number). Black dispersion (in PGMEA solvent, furnace carbon black is 27% by mass) (e1), or organic pigment mixed black ( In the PGMEA solvent, the organic pigment is 20% by mass (Red-256/Violet-23/Blue-156=40/20/40 (mass ratio)) (e2) as the colorant (E).

In each of the Examples and Comparative Examples, as additives (F), active agents (f1: BYK310) and (f3) fluorine-based surfactants (including perfluorobutyl ethyl methacrylate, polyethylene glycol methyl A copolymer of structural units derived from methyl acrylate and n-butyl methacrylate, weight average molecular weight: 20000), and as an additive, N-phenyl-3-aminopropyl trimethoxysilane (f2) is added .

In the examples, the above-mentioned active agents (f1), (f3) and additives (f2) are all added. However, in the photosensitive resin composition, even if these active agents and additives are not essential components, and the rest is the same composition, the same evaluation results as the examples disclosed here can be obtained. .

In each of the Examples and Comparative Examples, 3-methoxybutyl acetate (g1) and propylene glycol monomethyl ether acetate (g2) were used as solvents in a ratio of 15/85 (mass ratio).

[Examples 1 to 26 and Comparative Examples 1 to 5] At room temperature (25°C±2°C), the type and amount of alkali-soluble resin (A), crosslinking agent (B), photopolymerization initiator (C), The sensitizer (D), the coloring agent (E), the additive (E), and the solvent (G) were uniformly mixed, respectively, to obtain the photosensitive resin composition of each Example and Comparative Example. In addition, in Examples 19 to 21 and Comparative Example 5, the coloring agent (E) was not formulated, and it was a transparent resin composition.

[Line pattern evaluation] The photosensitive resin compositions of Examples 1 to 26 and Comparative Examples 1 to 5 were coated on a glass substrate (100mm×100mm) using a spin coater, and prebaked at 100°C for 120 seconds to form a coating membrane. Next, using a proximity exposure machine (product name: TME-150RTO, manufactured by TOPCON CORPORATION), the coating film was irradiated with ultraviolet rays through a negative mask in which a line pattern with a width of 20 μm was formed with an exposure gap of 50 μm. . Set the exposure level to 200mJ/cm ² . The exposed coating film was developed for 50 seconds using a 0.04% by mass KOH aqueous solution at 26° C., and then post-baked at 230° C. for 30 minutes, thereby forming a line pattern with a film thickness of 10 μm as a cured film.

(Evaluation of pattern linear travel) The formed line pattern was observed by an optical microscope to evaluate the linear travel of the pattern. The pattern linear travel property was evaluated as "good" when there was no undulation on the edge of the line, and "bad" when there was undulation on the edge of the line.

(Taper Angle) The taper angle was evaluated for the line pattern formed with an exposure amount of 200 mJ/cm ² . The taper angle was measured using a scanning electron microscope as the bonding angle between the pattern and the substrate. The measured cone angles are shown in Table 1. The closer the taper angle is to 90°, the closer the shape of the pattern cross-section is to the desired rectangular shape. When the taper angle is much smaller than 90°, the shape of the cross section of the pattern is not the desired rectangular shape. In addition, based on the measurement result of the taper angle, the cross-sectional shape of the line pattern was determined based on the following determination criteria. The results are shown in Table 1 together. ◎: The taper angle is 80° or more and 90° or less. ○: The taper angle is 70° or more and less than 80°. △: The taper angle is 50° or more and less than 70°. ×: The taper angle is less than 50°.

[Evaluation of OD value] The photosensitive resin compositions of Examples 1 to 26 and Comparative Examples 1 to 5 were coated on a glass substrate (100mm×100mm) using a spin coater, and prebaked at 100°C for 120 seconds to form Coating film. Next, a proximity exposure machine (product name: TME-150RTO, manufactured by TOPCON CORPORATION) was used to expose the photosensitive resin layer with an exposure amount of 200 mJ/cm ² and an exposure gap of 50 μm. The exposed photosensitive resin layer was post-baked at 230°C for 30 minutes, thereby forming a cured film. The thickness of the formed light-shielding film was 10 μm. The OD value per 10 μm of the formed light-shielding film was measured using a transmittance measuring device (D-200II, manufactured by GretagMacbeth), and the OD value per 1 μm was calculated using a fitting curve. Table 1 shows the measurement results of the OD value. The cured films formed using the photosensitive resin compositions of Examples 1 to 18, 22 to 26 and Comparative Examples 1 to 4 containing a black coloring agent all had an OD value of 0.45/μm, indicating that a cured film with excellent light-shielding properties was formed . On the other hand, the OD value of the cured film formed using the photosensitive resin composition of Examples 19-21 and Comparative Example 5 which does not contain a coloring agent is 0.01/micrometer, and it turns out that the cured film with high transmittance was formed.

Claims (13)

A photosensitive resin composition comprising: Alkali-soluble resin (A), Crosslinking agent (B), and Photopolymerization initiator (C); The crosslinking agent (B) includes a monofunctional (meth)acrylic monomer (B1), and the monofunctional (meth)acrylic monomer (B1) contains a biphenyl skeleton that may have a substituent or may Terphenyl skeleton with substituents. The photosensitive resin composition according to claim 1, wherein the monofunctional (meth)acrylic monomer (B1) contains a biphenyl skeleton-containing monofunctional (meth)acrylic monomer (B1a). The photosensitive resin composition according to claim 2, wherein the monofunctional (meth)acrylic monomer (B1a) contains a compound represented by the following formula (B1-1),

(In formula (B1-1), R ^b1 is a hydrogen atom or a methyl group, R ^b2 is an alkylene group having 1 or more and 4 or less carbon atoms, BP is an optionally substituted biphenyl group, and n1 is 0 or more And an integer of 10 or less, when n1 is 0, X ^b1 is -O- or -NH-, and when n1 is an integer of 1 to 10, X ^b1 is selected from -O-, -NH-, -O-CO -*, -NH-CO-*, -O-CO-O-, and -NH-CO-O-* linking groups in the group consisting of one of the asymmetric linking groups in the foregoing linking groups The bonding bond marked with * is the bonding bond with BP. The photosensitive resin composition according to any one of claims 1 to 3, wherein the crosslinking agent (B) further contains a polyfunctional (meth)acrylic monomer (B2). The photosensitive resin composition according to claim 4, wherein the polyfunctional (meth)acrylic monomer (B2) is bifunctional or more. The photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin (A) contains a resin having a Cardo structure. The photosensitive resin composition according to any one of claims 1 to 3, wherein the amount of the monofunctional (meth)acrylic monomer (B1) relative to the total mass of the crosslinking agent (B) The content is 5% by mass or more and 50% by mass or less. The photosensitive resin composition according to any one of claims 1 to 3, which further contains a sensitizer (D). The photosensitive resin composition according to any one of claims 1 to 3, which further contains a colorant (E). The photosensitive resin composition according to claim 9, wherein the colorant (E) is a black pigment. The photosensitive resin composition according to any one of claims 1 to 3, which further contains a hydrophobic agent (F). A method for manufacturing a patterned cured film, which includes the following steps: The step of coating the photosensitive resin composition of any one of claims 1 to 11 on a substrate to form a photosensitive resin layer, The step of exposing the aforementioned photosensitive resin layer in a position-selective manner, and The step of developing the aforementioned photosensitive resin layer after exposure with a developing solution. A cured film obtained by curing the photosensitive resin composition according to any one of claims 1 to 11.