TWI529486B - Photosensitive resin composition, photosensitive element, method for producing resist pattern, and method for producing printed wiring board - Google Patents

Description

Photosensitive resin composition, photosensitive element, method for producing photoresist pattern, and method for producing printed wiring board

The present invention relates to a photosensitive resin composition, a photosensitive element using the photosensitive resin composition, a method for producing a photoresist pattern, and a method for producing a printed wiring board.

In the field of the production of printed wiring boards, as a photoresist material used for etching treatment, plating treatment, etc., a photosensitive resin composition has been widely used, and a support and a protective film are used for the photosensitive resin composition. The photosensitive element obtained.

The printed wiring board is formed by laminating a photosensitive element on a circuit-forming substrate, exposing it to a pattern, and removing the unexposed part by a developing solution to form a photoresist pattern, and using the photoresist pattern as a mask. After the etching treatment or the plating treatment is performed to form a circuit, the method of removing and removing the hardened portion from the substrate is performed.

From the standpoint of environmental protection and safety, an alkali developing type using sodium carbonate or the like as a developing solution for removing the photoresist of the unexposed portion has become mainstream. The developer can be used as long as it has a certain ability to dissolve the photosensitive resin composition layer, and the photosensitive resin composition is dissolved or dispersed in the developer at the time of development.

Here, in the case where the through hole provided on the circuit formation substrate is covered with the photoresist film, it is required that the photosensitive resin composition used has a photoresist film capable of covering the through hole without being washed by the developer or the water. Burst of spray pressure The capping property, that is, the reliability of the cap hole.

A photosensitive resin composition containing a bifunctional monomer or a trifunctional monomer having a urethane bond has been proposed as a photosensitive resin composition having excellent cap hole reliability (see, for example, Patent Documents 1 and 2). Further, a photosensitive resin composition of a isocyanuric acid ring monomer modified with polycaprolactone is also disclosed (for example, see Patent Document 3).

[Previous Technical Literature] [Patent Literature]

Patent Document 1: Japanese Patent Publication No. Hei 10-142789

Patent Document 2: Japanese Patent Publication No. 2001-117224

Patent Document 3: Specification No. WO2007/049519

However, the photosensitive resin composition containing a bifunctional monomer having a urethane bond described in Patent Documents 1 and 2 may not provide sufficient capping reliability; and further, it contains a trifunctional monomer having a urethane bond. In the photosensitive resin composition, the cured film is likely to be hard and brittle. Further, the photosensitive resin composition described in Patent Document 3 needs to be further improved in terms of resolution.

The present invention has been made in view of such actual circumstances, and an object of the present invention is to provide a photosensitive resin composition which is excellent in resolution and excellent in mechanical strength of a cured film and has flexibility, that is, a photosensitive tree having excellent cover hole reliability. A lipid composition, a photosensitive element using the photosensitive resin composition, a method for producing a photoresist pattern, and a method for producing a printed wiring board.

The first aspect of the present invention is a photosensitive resin composition comprising the following components: (A) component: a binder polymer, and (B) component: a polymerizable compound having at least one ethylenically unsaturated bond, and C) component: a photopolymerization initiator, and the component (B) contains a compound represented by the following formula (I). (wherein R ¹ represents a divalent organic group, and R ² represents a group represented by the following formula (II)), (wherein R ³ represents a hydrogen atom or a methyl group, X represents an alkylene group, and n represents an integer of 10 to 25).

By including the compound represented by the above formula (I) in the photosensitive resin composition, the reliability and resolution of the lid hole can be improved.

Further, a second aspect of the present invention is a photosensitive resin composition comprising the following components: (A) component: a binder polymer, and (B) component: a polymerizable compound having at least one ethylenically unsaturated bond, And (C) component: a photopolymerization initiator, and the component (B) contains a reaction product of a compound represented by the following formula (III) and a compound represented by the following formula (IV). (wherein R ³ represents a hydrogen atom or a methyl group, X represents an alkylene group, and n represents an integer of 10 to 25), (wherein R ¹ represents a divalent organic group).

By allowing the photosensitive resin composition to contain the reaction product of the urethanization reaction of the above formula (III) with the above formula (IV), the lid hole reliability and resolution can be improved.

Further, a third aspect of the invention is a photosensitive element comprising a support and a photosensitive resin layer, wherein the photosensitive resin layer is a coating film of the photosensitive resin composition formed on the support.

Further, a fourth aspect of the present invention is a method for producing a resist pattern having a photosensitive resin layer forming step of forming a photosensitive resin layer on a circuit forming substrate, wherein the photosensitive resin layer is as described above a coating film of the photosensitive resin composition; at least a part of the photosensitive resin layer An exposure step of irradiating the active light to photoharden the exposed portion; and a developing step of removing the uncured portion of the photosensitive resin layer from the circuit-forming substrate by development.

Further, a fifth aspect of the present invention provides a method of manufacturing a printed wiring board, comprising the steps of: etching a substrate for forming a circuit having a photoresist pattern formed by the method for manufacturing a photoresist pattern; Or plating treatment to form a conductor pattern.

According to the present invention, it is possible to provide a photosensitive resin composition which is excellent in resolution and excellent in mechanical strength of a cured film and has flexibility, that is, a photosensitive resin composition excellent in lid hole reliability, and a photosensitive resin composition using the same A photosensitive element, a method for producing a photoresist pattern, and a method for producing a printed wiring board.

The invention is described in detail below. Further, (meth)acrylic acid in the present invention means acrylic acid and its corresponding methacrylic acid, (meth)acrylate means acrylate and its corresponding methacrylate, and (meth)acryloyl group means Acryl sulfhydryl and its corresponding methacryl fluorenyl group.

In addition, in this specification, the term "step" is not only an independent step, but even if it is not clearly distinguishable from other steps, it is included in the term as long as the intended effect of the step is achieved. In addition, in this specification, the numerical range indicated by "~" indicates that the inclusion is "~ The values described before and after are the minimum and maximum ranges. Further, in the present specification, when referring to the amount of each component in the composition, when a plurality of substances corresponding to the respective components are present in the composition, unless otherwise specified, it means the plurality of substances present in the composition. Total measurement.

<Photosensitive resin composition>

The photosensitive resin composition of the present invention contains (A) a component: a binder polymer, (B) a component: a polymerizable compound having at least one ethylenically unsaturated bond, and (C) a component: a photopolymerization initiator. In the photosensitive resin composition, the component (B) contains a compound represented by the following formula (I) or a compound represented by the following formula (III) and a urethane of a compound represented by the following formula (IV). The reaction product of the reaction.

In the formula (I) and the formula (II), R ¹ represents a divalent organic group, and R ² represents a group represented by the above formula (II). R ³ represents a hydrogen atom or a methyl group, X represents an alkylene group, and n represents an integer of 10 to 25.

In the general formula (III) and the general formula (IV), R ³ , X and n are respectively synonymous with R ³ , X and n in the above formula (II), and R ¹ and R in the formula (I) ¹ synonymous.

By containing the above specific compound as a polymerizable compound, a photosensitive resin composition having excellent lid hole reliability and resolution can be formed. Therefore, the photosensitive resin composition can be suitably used for producing a multilayer printed wiring board having a fine circuit layer, and is particularly suitable for use in a cover hole.

[Component (B): a polymerizable compound having at least one ethylenically unsaturated bond]

In the photosensitive resin composition of the present invention, the compound represented by the above formula (I) or the compound represented by the above formula (III) and the compound represented by the above formula (IV) are contained as the component (B). The reaction product of the urethanization reaction of the compound is an essential component.

In the above formula (I) and formula (IV), R ¹ represents a divalent organic group.

The divalent organic group represented by R ¹ is not particularly limited as long as it contains a carbon atom and is capable of linking an isocyanurate ring and a guanamine group. For example, an alkylene group having 1 to 10 carbon atoms and an extended aryl group having 6 to 10 carbon atoms may be mentioned. Further, the alkylene group having 1 to 10 carbon atoms may be linear or branched. Further, three R ¹ in the general formula (I) and the general formula (IV) may be the same or different.

Specific examples of the alkylene group having 1 to 10 carbon atoms include a methylene group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an extended butyl group. Base, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, 2-ethyl-extension hexyl group, hydrazine group and hydrazine group. Examples of the aryl group having 6 to 10 carbon atoms include a stretching phenyl group and the like.

In the present invention, R ^{1 is} preferably an alkylene group having 2 to 10 carbon atoms, more preferably an alkylene group having 3 to 8 carbon atoms, from the viewpoint of reliability and resolution of the lid hole.

The three R ² in the above formula (I) may be the same or different from each other.

In the above formula (II) and formula (III), X represents an alkylene group. The carbon number of the alkylene group is not particularly limited, but from the viewpoint of reliability and resolution of the cap hole, it is preferably an alkylene group having 2 to 7 carbon atoms, more preferably an alkylene group having 2 to 4 carbon atoms. .

Specific examples of the alkylene group in X include an ethyl group, a propyl group, a butyl group, a pentyl group and a hexyl group. Further, the above alkylene group may be linear or branched. Further, 10 or more Xs in the formula (II) may be the same or different from each other, but are preferably the same as each other.

Further, although n represents an integer of 10 to 25, it is preferably 15 to 25 from the viewpoint of reliability and strength of the cover hole.

The compound represented by the above formula (I) can be produced, for example, by a transesterification reaction of a compound represented by the following formula (III) with a compound represented by the following formula (IV). The reaction conditions are not particularly limited as long as the reaction conditions are usually such that a urethane bond is formed, and the reaction may be carried out using a suitable catalyst or the like.

[Chemical 5]

R ³ , X and n are respectively synonymous with R ³ , X and n in the above formula (II), and preferred embodiments are also the same. Further, R ¹ has the same meaning as R ¹ in the formula (I), and the preferred form is also the same.

The compound represented by the formula (I) is a compound obtained by subjecting three molecules of the compound represented by the formula (III) to the three isocyanate groups of the compound represented by the formula (IV).

In the reaction product of the compound represented by the above formula (III) and the compound represented by the above formula (IV), in addition to the compound represented by the formula (I), one molecule or two molecules may be contained. A compound produced by the addition reaction of a compound represented by the formula (III) and a compound represented by the formula (IV) in one molecule. In addition, reaction products other than these may also be included.

The content of the compound represented by the formula (I) contained in the reaction product of the compound represented by the above formula (III) and the compound represented by the above formula (IV) is not particularly limited. From the viewpoint of the reliability and strength of the lid hole, it is preferably 15% by mass or more, and more preferably 25% by mass or more.

In the photosensitive resin composition, the content of the reaction product of the compound represented by the above formula (I) or the compound represented by the above formula (III) and the compound represented by the above formula (IV) is not Special restrictions. From the viewpoint of the reliability of the lid hole, the mechanical strength of the cured film, and the flexibility, the photosensitive resin composition is preferably from 1% by mass to 25% by mass, and more preferably from 5% by mass to 20% by mass.

In the photosensitive resin composition, the compound represented by the above formula (I) or the compound represented by the above formula (III) and the compound represented by the above formula (IV) are reacted as the component (B). The product is preferably a compound containing 1% by mass to 25% by mass of R ¹ as an alkylene group having 1 to 10 carbon atoms, X being an alkylene group having 2 to 4 carbon atoms, and n being 10 to 25; The reaction product of the compound represented by the formula (I) or the compound represented by the above formula (III) and the compound represented by the above formula (IV) is more preferably contained in an amount of 5% by mass to 20% by mass of R ¹ . X is a compound having a C 2 to 4 alkyl group and n is 15 to 25.

Further, in the present invention, the component (B) is reacted with a compound represented by the above formula (I) or a compound represented by the above formula (III) and a compound represented by the above formula (IV) as an essential component. In addition to the product, a polymerizable compound having at least one ethylenically unsaturated bond (hereinafter sometimes referred to as "other polymerizable compound") may be contained.

Examples of the other polymerizable compound include a compound obtained by subjecting an α,β-unsaturated carboxylic acid to a condensation reaction with a polyhydric alcohol, and a compound obtained by adding an α,β-unsaturated carboxylic acid to a compound containing a glycidyl group. a compound, an alkyl (meth)acrylate, a phthalate of a (meth)acrylic acid derivative, a (meth) acrylate compound having a urethane bond, and a bisphenol A (meth) acrylate Compound.

Examples of the compound obtained by subjecting the α,β-unsaturated carboxylic acid to a polycondensation reaction with a polyhydric alcohol include polyethylene glycol di(meth)acrylate having a number of ethylene oxide groups of 2 to 14 and stretching. The number of polypropylene glycol di(meth) acrylate and ethoxy group having a number of propoxy groups of 2 to 14 is 2 to 14 Polyethylene glycol polypropylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate having a number of propoxy groups of 2 to 14 Ester, trimethylolpropane ethoxylated tri(meth) acrylate, trimethylolpropane diethylene ethoxy tri(meth) acrylate, trimethylolpropane triethylene ethoxy tris Acrylate, trimethylolpropane tetraethyleneoxytri(meth)acrylate, trimethylolpropane pentaerythritol tris(meth)acrylate, tetramethylolmethanetris(methyl) ) acrylate, tetramethylol methane tetra(meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.

Examples of the compound obtained by adding an α,β-unsaturated carboxylic acid to a compound containing a glycidyl group include bisphenol A dioxoethyl di(meth)acrylate and bisphenol A trioxane. Bisphenol A polyoxyethylidene di(meth)acrylate, trimethylolpropane tricondensate, such as ethyl di(meth)acrylate, bisphenol A decahydroethylidene di(meth)acrylate A (meth) acrylate adduct of glyceryl ether and a (meth) acrylate adduct of bisphenol A diglycidyl ether.

Examples of the alkyl (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate. Wait.

Examples of the phthalic acid ester of the (meth)acrylic acid derivative include γ-chloro-β-hydroxypropyl-β ′ -(meth)acryloxyethyl-phthalate. β-Hydroxyethyl-β ' -(meth)acrylomethoxyethyl-phthalate and β-hydroxypropyl-β ' -(methyl)propenyloxyethyl-o-phenylene Formate and so on.

Examples of the (meth) acrylate compound having a urethane bond include a (meth)acrylic acid derivative having an OH group at the β-position, isophorone diisocyanate, 2,6-toluene diisocyanate, and 2,4. Addition reaction of diisocyanate compound such as toluene diisocyanate or 1,6-hexamethylene diisocyanate, tris((meth)acryloxytetraethyleneethylene glycol isocyanate) hexamethylene isocyanurate EO modified urethane di(meth) acrylate and EO, PO modified urethane di(meth) acrylate, and the like.

Further, EO represents ethylene oxide, and the EO-modified compound has a block structure of an ethoxy group. Further, PO represents propylene oxide, and the PO-modified compound has a block structure in which a propoxy group is extended. Examples of the EO-modified urethane di(meth)acrylate include a product name UA-11 manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and the like. Further, examples of the EO and PO-modified urethane di(meth)acrylate include the product name UA-13 manufactured by Shin-Nakamura Chemical Industry Co., Ltd.

Examples of the bisphenol A-based (meth) acrylate compound include 2,2-bis(4-((meth) propylene oxy) ethoxy) phenyl) propane, 2, 2-double. (4-((Methyl)propenyloxypolypropoxy)phenyl)propane, and 2,2-bis(4-((meth)propenyloxy) ethoxylated poly(propoxy) Base) phenyl)propane and the like. These compounds may be used singly or in combination of two or more.

Among these compounds, at least one of a bisphenol A-based (meth) acrylate compound and a (meth)acrylic acid derivative phthalate is preferably used from the viewpoint of chemical resistance. More preferably, it contains both.

The content of the other polymerizable compound is not particularly limited, but is preferably 50% by mass to 90% by mass based on 100% by mass of the total amount of the component (B) from the viewpoint of the reliability of the cap hole and the resolution. More preferably, it is 60% by mass to 80% by mass.

Further, the content of the polymerizable compound having at least one ethylenically unsaturated bond in the above (B) is preferably 20% by mass to 60% by mass based on 100% by mass of the total of the components (A) and (B). More preferably, it is 30% by mass to 55% by mass. When the content is 20% by mass or more, the light sensitivity tends to be improved, and when it is 60% by mass or less, the flexibility of the cured film tends to be further improved.

[(A) component: binder polymer]

Examples of the component (A) which can be used in the present invention include a acryl resin, a styrene resin, an epoxy resin, a guanamine resin, a guanamine epoxy resin, and an alkyd resin. And phenolic resin and the like. From the standpoint of alkali developability, an acrylic resin is preferred. The above resins may be used alone or in combination of two or more.

The (A) binder polymer can be produced, for example, by radical polymerization of a polymerizable monomer. Examples of the polymerizable monomer include a polymerizable styrene derivative substituted with an α-position or an aromatic ring such as styrene, vinyl toluene, and α-methylstyrene, and diacetone acrylamide. An ester of a vinyl alcohol such as acrylamide, acrylonitrile or vinyl-n-butyl ether; an alkyl (meth)acrylate; a benzyl (meth)acrylate; a tetrahydrofurfuryl (meth)acrylate; Methyl) dimethylaminoethyl acrylate, ( Diethylaminoethyl methacrylate, glycidyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetra(meth)acrylate Fluoropropyl ester, (meth)acrylic acid, α-bromoacrylic acid, α-chloroacrylic acid, β-furyl (meth)acrylic acid, β-styryl (meth)acrylic acid, maleic acid, maleic anhydride, horse Maleic acid monoester, fumaric acid, cinnamic acid, α-cyano cinnamic acid, itaconic acid, crotonic acid and propyne, such as monomethyl ester, monoethyl maleate, monoisopropyl maleate acid. These may be used alone or in combination of two or more.

The (meth)acrylic acid alkyl ester may, for example, be a compound represented by the following formula (V): H ₂ C=C(R ⁶ )-COOR ⁷ (V) [in the formula (V), R ⁶ A hydrogen atom or a methyl group, R ⁷ represents an alkyl group having 1 to 12 carbon atoms, and a compound in which an alkyl group of the compound is substituted with a hydroxyl group, an epoxy group, a halogen group or the like.

Examples of the alkyl group having 1 to 12 carbon atoms represented by R ⁷ in the above formula (V) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. , mercapto, decyl, undecyl, dodecyl and structural isomers of such groups.

Examples of the monomer represented by the above formula (V) include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, and butyl (meth)acrylate. Amyl methacrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, decyl (meth) acrylate , (meth) methacrylate, undecyl (meth) acrylate, and Dodecyl (meth)acrylate. These may be used alone or in combination of two or more.

Further, from the standpoint of alkali developability, the binder polymer of the component (A) in the present invention preferably contains a carboxyl group. The carboxyl group-containing binder polymer can be produced, for example, by radically polymerizing a polymerizable monomer having a carboxyl group with another polymerizable monomer.

Examples of the polymerizable monomer having a carboxyl group include acrylic acid and methacrylic acid, and methacrylic acid is preferred.

From the standpoint of the balance between the alkali developability and the alkali resistance, the content ratio of the structural unit derived from the polymerizable monomer having a carboxyl group in the (A) binder polymer (polymerizable monomer having a carboxyl group is used with respect to the use) The ratio of all the polymerizable monomers is preferably from 12% by mass to 50% by mass, more preferably from 12% by mass to 40% by mass, still more preferably from 15% by mass to 30% by mass, particularly preferably from 15% by mass to the mass%. 25 mass%.

When the content is 12% by mass or more, the alkali developability tends to be improved. Moreover, when it is 50% by mass or less, alkali resistance tends to be excellent.

Further, from the standpoint of flexibility, the binder polymer of the component (A) in the present invention preferably contains a structural unit derived from styrene or a styrene derivative.

The content of the structural unit derived from the styrene or the styrene derivative is not particularly limited, but from the viewpoint of good adhesion and peeling properties, it is preferable to contain 0.1% by mass in the binder polymer. ~30% by mass, more preferably 1% by mass to 28% by mass, particularly preferably 1.5% by mass %~27% by mass.

When the content is 0.1% by mass or more, the adhesion tends to be improved. Moreover, by making it 30 mass % or less, it can suppress that a peeling sheet becomes large, and can suppress the extension of peeling time.

These binder polymers may be used alone or in combination of two or more. Examples of the binder polymer when two or more types are used in combination include two or more kinds of binder polymers composed of different copolymerized components, two or more kinds of binder polymers having different weight average molecular weights, and different dispersions. Two or more kinds of binder polymers, etc.

The weight average molecular weight of the above (A) binder polymer is preferably from 20,000 to 300,000, more preferably from 30,000 to 150,000, still more preferably from 40,000 to 110,000, from the standpoint of balance of mechanical strength and alkali developability.

When the weight average molecular weight is 20,000 or more, the development liquid resistance tends to be further improved. Further, by making it 300,000 or less, the development time can be suppressed from being prolonged.

Further, the weight average molecular weight in the present invention is a value obtained by gel permeation chromatography and converted from a calibration curve prepared using standard polystyrene.

The content of the (A) binder polymer is preferably 30% by mass to 80% by mass, and more preferably 50% by mass to 70% by mass based on 100% by mass of the total of the components (A) and (B). .

When the content of the component (A) is 30% by mass or more, the flexibility of the cured film can be further improved. In addition, when it is 80% by mass or less, there is a tendency to exhibit better light sensitivity.

[(C) component: photopolymerization initiator]

The photopolymerization initiator as the component (C) may, for example, be benzophenone or N,N'-tetramethyl-4,4'-diaminobenzophenone (Michler's ketone). )), N,N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, 2-benzyl-2 -dimethylamino-1-(4-morpholinylphenyl)-butanone-1, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylacetone-1, etc. Aromatic ketones; 2-ethyl hydrazine, phenanthrenequinone, 2-tert-butyl fluorene, octamethyl hydrazine, 1,2-benzopyrene (1,2-Benzanthraquinone), 2,3- Benzopyrene, 2-phenylindole, 2,3-diphenylanthracene, 1-chloroindole, 2-methylindole, 1,4-naphthoquinone, 9,10-phenanthrenequinone, 2 - anthracene such as methyl-1,4-naphthoquinone or 2,3-dimethylhydrazine; benzoin ether compounds such as benzoin methyl ether, benzoin ethyl ether, and benzoin phenyl ether Benzene-caine compounds such as benzoin, methyl benzene, ethyl benzoate; benzyl derivatives such as benzyl dimethyl ketal; 2-(o-chlorophenyl)-4,5-diphenyl Imidazole dimer, 2-(o-chlorophenyl)-4,5-bis(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazolium a polymer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer, etc. 2,4,5-triarylimidazole dimer; acridine derivative such as 9-phenyl acridine, 1,7-bis(9,9'-acridinyl)heptane; N-phenylglycine , N-phenylglycine derivative; coumarin compound; oxazole compound.

These may be used alone or in combination of two or more.

In addition, two of the above 2,4,5-triarylimidazole dimers are 2,4,5-three The substituent of the aryl group of the aryl imidazole may be a compound which is symmetrical to each other, or may be an asymmetric compound.

Further, a thioxanthone-based compound may be combined with a tertiary amine compound as in the combination of diethylthioxanthone and dimethylaminobenzoic acid.

From the standpoint of adhesion and sensitivity, the photosensitive resin composition preferably contains at least one of 2,4,5-triarylimidazole dimer as a photopolymerization initiator, more preferably At least one of the 2,4,5-triarylimidazole dimer and at least one of the aromatic ketones are used as a photopolymerization initiator.

The content of the (C) photopolymerization initiator is preferably from 0.01% by mass to 20% by mass, more preferably from 0.2% by mass to 5% by mass based on 100% by mass of the total of the components (A) and (B). %.

When the content is 0.01% by mass or more, the light sensitivity tends to be better, and when it is 20% by mass or less, the absorption at the surface of the photosensitive resin layer during exposure is suppressed from increasing. The tendency to make the internal light hardening better.

[Other ingredients]

Further, other components may be contained in the photosensitive resin composition as needed. Examples of other components include sensitizing dyes such as coumarin and pyrazoline, dyes such as malachite green, photochromic agents such as tribromophenylhydrazine and colorless crystal violet, and thermal coloring preventive agents and p-toluenesulfonamide. Plasticizers, pigments, fillers, defoamers, flame retardants, stabilizers, adhesion imparting agents, leveling agents, release promoters, antioxidants, perfumes, imaging agents, and thermal crosslinking agents.

As for the content of other ingredients, relative to (A) and (B) The total amount of the fractions is 100% by mass, and may be contained in an amount of about 0.01% by mass to 20% by mass. These components may be used singly or in combination of two or more.

The photosensitive resin composition may contain at least one organic solvent as needed. The organic solvent is not particularly limited as long as it is an organic solvent which is usually used. Specific examples thereof include solvents such as methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N,N-dimethylformamide, and propylene glycol monomethyl ether. And such mixed solvents.

For example, the (A) binder polymer, the (B) polymerizable compound, and the (C) photopolymerization initiator may be dissolved in the organic solvent to prepare a solid content of about 30% by mass to 60% by mass. The solution (hereinafter referred to as "coating liquid") is used.

In addition, the solid component means a component remaining after removing a volatile component from the solution (photosensitive resin composition).

The coating liquid can be used for the formation of a photosensitive resin layer, for example, as follows. The coating liquid is applied onto the surface of a support such as a support film or a metal plate to be described later and dried, whereby a photosensitive resin layer derived from the photosensitive resin composition can be formed on the support.

Examples of the metal plate include iron-based alloys such as copper, copper-based alloys, nickel, chromium, iron, and stainless steel, and copper, copper-based alloys, and iron-based alloys are preferable.

The thickness of the photosensitive resin layer to be formed varies depending on the application, but it is preferably from about 1 μm to 100 μm in terms of the thickness after drying, and the surface of the opposite side of the photosensitive resin layer opposite to the support may be covered with a protective film (surface) ). The protective film may, for example, be a polymer film such as polyethylene or polypropylene.

<Photosensitive element>

The photosensitive element of the present invention has a support and a photosensitive resin layer which is a coating film of the photosensitive resin composition formed on the support, and has other layers such as a protective film provided as needed. .

[support]

As the support, for example, a polymer film having heat resistance and solvent resistance such as polyethylene terephthalate, polypropylene, polyethylene, or polyester can be used.

The thickness of the support (hereinafter sometimes referred to as "support film") is preferably from 1 μm to 100 μm, more preferably from 1 μm to 50 μm, still more preferably from 1 μm to 30 μm. By making the thickness of the support 1 μm or more, it is possible to suppress cracking of the support film when the support film is peeled off. Further, by setting it to 100 μm or less, the decrease in resolution can be suppressed.

[protective film]

The photosensitive element may have a protective film covering a surface (surface) of the photosensitive resin layer opposite to the surface opposite to the support, as needed.

The protective film is preferably a protective film having a lower adhesive force to the photosensitive resin layer than the support film to the photosensitive resin layer, and is preferably a fish eye film.

Here, "fisheye" means heating and melting a material constituting a protective film. When a film is produced by kneading, extrusion molding, biaxial stretching, casting, or the like, foreign matter, an unmelted material, an oxidative degradation product, or the like of the material is contained in the film. That is to say, "low fisheye" means that the above-mentioned foreign matter or the like in the film is small.

The thickness of the protective film is preferably from 1 μm to 100 μm, more preferably from 5 μm to 50 μm, still more preferably from 5 μm to 30 μm, particularly preferably from 15 μm to 30 μm. When the thickness of the protective film is 1 μm or more, cracking of the protective film can be suppressed when the protective film is peeled off and the photosensitive resin layer and the support film are laminated on the substrate. Further, by making it 100 μm or less, productivity can be improved.

〔Production method〕

The photosensitive element of the present invention can be produced, for example, as described below. It can be produced by a production method comprising the steps of: (A) component: a binder polymer, (B) component: a polymerizable compound, and (C) a photopolymerization initiator dissolved in the above organic solvent to prepare a coating. a step of applying a coating liquid onto the support to form a coating layer; and a step of drying the coating layer to form a photosensitive resin layer.

The details of the component (A) constituting the coating liquid: the binder polymer, the component (B): the polymerizable compound, the (C) photopolymerization initiator, and the organic solvent, and the details of the coating liquid are as described above. Further, the coating liquid may be a commercially available coating liquid or may be prepared by a conventional method.

The step of applying the above coating liquid onto the support can be carried out by using a roll coater, a notch coater, a gravure coater, an air knife coater, a die coater, and a wiper strip. Conventional methods such as cloth machines and sprayers are carried out.

Further, the coating layer is not particularly limited as long as it can remove at least a part of the organic solvent from the coating layer. For example, it can be carried out at 70 ° C to 150 ° C for about 5 minutes to 30 minutes.

From the viewpoint of preventing the diffusion of the organic solvent in the subsequent step, the amount of the residual organic solvent in the photosensitive resin layer after drying is preferably 2% by mass or less.

The thickness of the photosensitive resin layer in the photosensitive element can be appropriately selected depending on the use. The thickness of the photosensitive resin layer is preferably from 1 μm to 200 μm, more preferably from 5 μm to 100 μm, particularly preferably from 10 μm to 50 μm, in terms of thickness after drying. When the thickness of the photosensitive resin layer is 1 μm or more, industrial coating can be facilitated and productivity can be improved. When it is 200 μm or less, the effect of the present invention can be sufficiently obtained, the light sensitivity is high, and the photocurability of the bottom of the photoresist tends to be excellent.

The photosensitive element of the present invention may have an intermediate layer such as a buffer layer, an adhesive layer, a light absorbing layer, or a gas barrier layer, etc., as needed.

In the present invention, the intermediate layer can be applied, for example, to the intermediate layer described in Japanese Patent Laid-Open Publication No. 2006-098982.

The form of the photosensitive element of the present invention is not particularly limited. For example, it may be in the form of a sheet or may be wound into a roll shape on a winding core.

In the case of winding in a roll shape, it is preferable to wind the support film so as to be outside. Examples of the winding core include plastics such as a polyethylene resin, a polypropylene resin, a polystyrene resin, a polyvinyl chloride resin, and an ABS (acrylonitrile-butadiene-styrene copolymer).

From the standpoint of protecting the end face, it is preferred to obtain the roll-like feeling thus obtained The end face of the optical element is provided with an end face spacer, and from the standpoint of edge fusion resistance, it is preferable to provide a moisture-proof end face spacer. Further, as the packing method, it is preferably packaged in a black sheet having a small moisture permeability.

The photosensitive element of the present invention can be suitably used, for example, in a production method of a resist pattern described later.

<Method of Manufacturing Photoresist Pattern>

The method for producing a photoresist pattern of the present invention includes: (i) a photosensitive resin layer forming step of forming a photosensitive resin layer on a circuit forming substrate, wherein the photosensitive resin layer is a coating film of the photosensitive resin composition; (ii) an exposure step of irradiating at least a part of the photosensitive resin layer with an active light to cure the exposed portion; and (iii) developing the uncured portion of the photosensitive resin layer by developing the substrate for circuit formation Steps; and include additional steps as needed.

(i) Photosensitive resin layer forming step

In the photosensitive resin layer forming step, a photosensitive resin layer is formed on the circuit-forming substrate (hereinafter sometimes simply referred to as "substrate"), and the photosensitive resin layer is a coating film of the photosensitive resin composition. The circuit formation substrate usually has an insulating layer and a conductor layer formed on the insulating layer. The surface of the circuit-forming substrate that the photosensitive resin layer is in contact with is usually a metal surface, but the material thereof is not particularly limited.

As a method of forming a photosensitive resin layer on a substrate, for example, on In the case where the photosensitive element has a protective film, the photosensitive resin layer of the photosensitive element can be pressure-bonded to the circuit-forming substrate while heating as needed after removing the protective film. Thereby, a laminate having a circuit formation substrate, a photosensitive resin layer, and a support in this order can be obtained.

The photosensitive resin layer forming step is preferably carried out under reduced pressure from the standpoint of adhesion and compliance. The heating at the time of pressure bonding is preferably carried out at a temperature of from 70 ° C to 130 ° C. Further, the pressure bonding is preferably carried out at a pressure of about 0.1 MPa to 1.0 MPa (about 1 kgf/cm ² to 10 kgf/cm ² ), but these conditions can be appropriately selected as needed.

Further, pre-heat treatment of the substrate for circuit formation may be performed as needed. When the photosensitive resin layer is heated to 70° C. to 130° C., it is not necessary to preheat the circuit for forming a circuit board in advance. However, by performing preheating of the substrate for circuit formation, adhesion and compliance can be further improved. .

(ii) Exposure step

In the exposure step, at least a part of the photosensitive resin layer grease formed on the circuit-forming substrate is irradiated with the active light, and the exposed portion irradiated with the active light is photo-cured to form a latent image.

At this time, when the support (support film) existing on the photosensitive resin layer is transparent to the active light, the active light can be irradiated through the support film. On the other hand, when the support film is non-penetrating to the active light, the photosensitive resin layer is irradiated with the active light after the support film is removed.

As an exposure method, a method of irradiating an active ray as an image through a negative or positive mask pattern called a ART WORK can be cited. Method (mask exposure method). Further, a method of directly irradiating the active light into an image by a direct drawing exposure method such as LDI (Laser Direct Imaging) exposure method or DLP (Digital Light Processing) exposure method may be employed.

As a light source of the active light, a conventional light source such as a carbon arc lamp, a mercury vapor arc lamp, an ultrahigh pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, an argon laser gas laser or the like, a YAG laser or the like can be used. , semiconductor lasers, and gallium nitride-based blue-violet lasers that emit ultraviolet light. Further, a illuminating light source such as a photographic floodlight or a fluorescent lamp can be used.

(iii) development step

In the developing step, the uncured portion of the photosensitive resin layer is removed from the substrate for forming a substrate, and the photoresist formed by the cured product of the photosensitive resin layer is cured on the circuit-forming substrate. Graphic type.

When the support film is present on the photosensitive resin layer, after the support film is removed, the unexposed portion other than the exposed portion is removed (developed). Development methods include wet development and dry development.

In the case of wet development, development is carried out by a conventional development method using a developer corresponding to the photosensitive resin composition. Examples of the development method include a method using an immersion method, a paddle method, a spray method, a brushing method, a slapping method, a scapping, a shaking immersion, etc., from the viewpoint of improving the resolution, and a high-pressure spray method. for most suitable. It is also possible to develop two or more of the above methods in combination.

The component of the developer can be appropriately selected depending on the components of the photosensitive resin composition. For example, an alkaline aqueous solution, an aqueous developing solution, an organic solvent developing solution, and the like can be given.

When an alkaline aqueous solution is used as the developing solution, it is safer and more stable, and the workability is good. As the base of the alkaline aqueous solution, for example, an alkali hydroxide such as a hydroxide of lithium, sodium or potassium, a carbonate such as lithium, sodium, potassium or ammonium carbonate or a hydrogencarbonate, or an alkali metal such as potassium phosphate or sodium phosphate can be used. An alkali metal pyrophosphate such as phosphate, sodium pyrophosphate or potassium pyrophosphate.

The alkaline aqueous solution used for development is preferably 0.1% by mass to 5% by mass of a thin solution of sodium carbonate, 0.1% by mass to 5% by mass of a dilute solution of potassium carbonate, and 0.1% by mass to 5% by mass of a dilute solution of sodium hydroxide. 0.1% by mass to 5% by mass of a diluted solution of sodium tetraborate. Further, the pH of the alkaline aqueous solution used for development is preferably in the range of 9 to 11, and the temperature thereof can be adjusted according to the developability of the photosensitive resin layer. Further, a surfactant, an antifoaming agent, a small amount of an organic solvent for promoting development, and the like may be mixed in the alkaline aqueous solution.

The aqueous developing solution is, for example, a developing solution comprising water or an alkaline aqueous solution and one or more organic solvents. Here, as the base of the alkaline aqueous solution, in addition to the above, for example, borax, sodium metasilicate, tetramethylammonium hydroxide, ethanolamine, ethylenediamine, diethylenetriamine, and 2-amine may be mentioned. Alkyl-2-hydroxymethyl-1,3-propanediol, 1,3-diaminopropanol-2, morpholine, and the like. The pH of the aqueous developing solution is preferably as small as possible within a range in which development is sufficiently performed, and is preferably pH 8 to 12, more preferably pH 9 to 10.

Examples of the organic solvent used in the aqueous developing solution include, for example, 3- Acetyl alcohol, acetone, ethyl acetate, alkoxyethanol having an alkoxy group having 1 to 4 carbon atoms, ethanol, isopropanol, butanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, two Ethylene glycol monobutyl ether and the like. These solvents may be used alone or in combination of two or more. The content of the organic solvent in the aqueous developing solution is usually preferably from 2% by mass to 90% by mass. Further, the temperature thereof can be adjusted in accordance with the developability of the photosensitive resin layer. A small amount of a surfactant, an antifoaming agent, or the like may be mixed into the aqueous developing solution.

Examples of the organic solvent-based developing solution include 1,1,1-trichloroethane, N-methylpyrrolidone, N,N-dimethylformamide, cyclohexanone, and methyl isobutyl ketone. Γ-butyrolactone and the like. In order to prevent ignition, it is preferred to add water in an amount of 1% by mass to 20% by mass in these organic solvents.

In the present invention, after the unexposed portion is removed in the developing step, it may be subjected to heat treatment at about 60 ° C to 250 ° C or exposure treatment at about 0.2 mJ/cm ² to 10 mJ/cm ² as needed. The step of further hardening the pattern.

<Method of Manufacturing Printed Wiring Board>

The method for producing a printed wiring board according to the present invention includes the steps of forming a conductor pattern by performing an etching treatment or a plating treatment on a circuit formation substrate on which a resist pattern is formed by the above-described photoresist pattern type manufacturing method; Other steps such as a photoresist removal step are required.

In the etching process, a photoresist pattern formed on a substrate is used as a mask, and a conductor layer of a substrate for circuit formation not covered with a photoresist is etched away to form a conductor pattern.

The etching treatment method can be appropriately selected depending on the conductor layer to be removed. For example, examples of the etching liquid include a copper chloride solution, a ferric chloride solution, an alkali etching solution, and a hydrogen peroxide-based etching liquid. From the viewpoint of a good etching factor, a ferric chloride solution is preferably used.

On the other hand, in the plating process, a photoresist pattern formed on a substrate is used as a mask, and copper, solder, or the like is plated on the conductor layer of the circuit-forming substrate which is not covered with the photoresist. After the plating treatment, the hardened photoresist is removed, and the conductor layer covered by the photoresist is etched to form a conductor pattern.

As a method of the plating treatment, it may be an electrolytic plating treatment or an electroless plating treatment. Examples of the plating treatment include copper plating such as copper sulfate plating and copper pyrophosphate plating, solder plating such as high-throw solder plating, and Watt bath (nickel sulfate-nickel chloride). Nickel plating such as plating and nickel sulfonate plating, hard gold plating, and gold plating such as soft gold plating.

After the etching treatment and the plating treatment, the photoresist pattern on the substrate is removed. The removal of the photoresist pattern can be carried out, for example, by using an alkaline aqueous solution which is more alkaline than the alkaline aqueous solution used in the above development step. As the strongly alkaline aqueous solution, for example, a 1% by mass to 10% by mass aqueous sodium hydroxide solution, a 1% by mass to 10% by mass aqueous potassium hydroxide solution, or the like can be used. Among them, a 1% by mass to 10% by mass aqueous sodium hydroxide solution or a potassium hydroxide aqueous solution is preferably used, and a 1% by mass to 5% by mass aqueous sodium hydroxide solution or a potassium hydroxide aqueous solution is more preferably used.

Examples of the method of removing the photoresist pattern include a dipping method and a spraying method. These methods may be used singly or in combination.

In the case where the photoresist pattern is removed after the plating treatment, the conductor layer covered with the photoresist may be further etched by an etching process to form a conductor pattern, thereby producing a desired printed wiring board. The etching treatment method can be appropriately selected depending on the conductor layer to be removed. For example, the above etching liquid can be applied.

The method for producing a printed wiring board of the present invention can be applied not only to the manufacture of a single-layer printed wiring board but also to the manufacture of a multilayer printed wiring board, and can also be applied to a printed wiring board having a small-diameter through hole or the like. Manufacturing.

[Examples]

The invention will be specifically described below by way of examples. However, the present invention is not limited by the embodiments as long as it does not depart from the technical idea of the present invention. And, unless otherwise specified, "parts" and "%" are quality benchmarks.

<Examples 1 to 4, Comparative Examples 1 to 2>

The components of the types and the amounts (unit: g) shown in Table 1 were mixed to obtain a solution of the photosensitive resin compositions of Examples 1 to 4 and Comparative Examples 1 and 2.

The abbreviations of the components in Table 1 are as follows.

[component A]

‧(A-1): methacrylic acid/methyl methacrylate/butyl acrylate/styrene (25/50/20/5 (mass ratio)), weight average molecular weight=80,000, 50% by mass methylcellulose Agent / toluene = 6 / 4 (mass ratio) solution

‧(A-2): methacrylic acid/methyl methacrylate/ethyl acrylate (20/55/25 (mass ratio)), weight average molecular weight=80,000, 50% by mass methyl cellosolve/toluene=6 /4 (mass ratio) solution

Further, the weight average molecular weight was measured by a gel permeation chromatography (GPC) method and calculated using a standard polystyrene calibration curve. The GPC conditions and the acid value measurement steps are as follows.

(GPC condition)

Pump: Hitachi L-6000 type [manufactured by Hitachi, Ltd.]

Pipe column: Gelpack GL-R420+Gelpack GL-R430+Gelpack GL-R440 (3 in total) [above by Hitachi Chemical Co., Ltd. Made, product name]

Effervescent solution: tetrahydrofuran

Measuring temperature: 40 ° C

Flow rate: 2.05mL/min

Detector: Hitachi L-3300 RI [manufactured by Hitachi, Ltd., product name]

[Component B]

‧BPE-500: 2,2-bis(4-(methacryloxypentadecane)phenyl)[manufactured by Shin-Nakamura Chemical Industry Co., Ltd.]

‧FA-MECH: γ-chloro-β-hydroxypropyl-β'-methacryloxyethyl-phthalate [Manufactured by Hitachi Chemical Co., Ltd.]

‧ Sample A: a compound of the above formula (I), and R ¹ is -C ₆ H ₁₂ -, R ² is n=10 in the formula (II), X is an exoethyl group, and R ³ is an Base compound

‧ Sample B: a compound of the formula (I), and R ¹ is -C ₆ H ₁₂ -, R ² is n = 15 in the formula (II), X is an exoethyl group, and R ³ is a methyl group Compound

JTX0309: a compound represented by the following formula (VI), wherein R ⁵¹ and R ⁵² are a group represented by the following formula (VIIa), and R ⁵³ is a group represented by the following formula (VIIb) ( Manufactured by Cytec Industries Inc., Japan, sample name: JTX0309)

[Chemical 6]

‧UA-21: Tris(methacryloxytetramethylene glycol isocyanate hexamethylene)isocyanurate [manufactured by Shin-Nakamura Chemical Industry Co., Ltd.]

[Component C]

B-CIM: 2-(o-chlorophenyl)-4,5-diphenylimidazole 2mer

‧EAB: N,N'-tetraethyl-4,4'-diaminobenzophenone

[Other ingredients]

‧MKG: Malachite Green

‧LCV: colorless crystal violet

A solution of the photosensitive resin composition obtained by the above method was uniformly applied onto a 16 μm-thick polyethylene terephthalate film (trade name: G2-16, manufactured by Teijin Co., Ltd.) as a support film, and After drying in a hot air convection dryer at 100 ° C for 10 minutes to form a photosensitive resin layer, a protective film made of polyethylene (trade name: NF-13, manufactured by Tamapoly Co., Ltd.) is adhered to the photosensitive resin layer to protect it. A photosensitive resin composition laminate was obtained. The film thickness after drying of the photosensitive resin layer was 40 μm.

Next, on a 1.6 mm-thick copper-clad laminate (manufactured by AIN) having 35 μm thick copper foil on both sides, as shown in Fig. 1, four dies were used, respectively. The machine has three independent circular holes 41 and three three-holes 42 in which the circular holes are gradually spaced apart by the respective apertures of 4, 5, and 6 mm in diameter. The burrs generated when the round holes 41 and the third holes 42 are formed are removed by using a grinder (manufactured by Sanken Co., Ltd.) having a brush corresponding to #600, and this is used as the hole crack number measuring substrate 40.

The substrate for measuring the number of fractures of the obtained pores was heated to 80 ° C, and the photosensitive resin composition laminate obtained by the above method was peeled off from the protective film, and the photosensitive resin layer was opposed to the copper surface at 120 ° C and 0.4 MPa. Laminated to obtain a laminated plate in which a photosensitive resin layer and a polyethylene terephthalate film were laminated on a substrate for measuring the number of cracks in the hole. After lamination, the substrate for measuring the number of cracks in the hole is cooled, and when the temperature of the substrate for measuring the number of cracks of the hole is lowered to 23 ° C, the Stouffer 21-stage stage is closely adhered on the surface of the polyethylene terephthalate film. The exposure meter was used, and an exposure machine HMW-201B (manufactured by OAK Co., Ltd.) having a high-pressure mercury lamp was used to photoharden the exposure amount of the 8.0-stage photohardening.

(cover hole reliability)

After the exposure, the film was allowed to stand at room temperature for 15 minutes, and then the polyethylene terephthalate film was peeled off from the substrate for measuring the number of holes to be broken, and developed by spraying 30 ° C and a 1% by weight aqueous sodium carbonate solution for 60 seconds. After the development, the number of hole breaks in the three-joined hole was measured, and the crack rate of the abnormal shape cap hole was calculated to evaluate the reliability of the cap hole.

Next, a cylindrical material having a diameter of 1.5 mm was used for the cured film covering the circular hole portion, and a rheometer (manufactured by RHEOTECH Co., Ltd.) was used. The strength and elongation at the time of breaking were measured. The larger the value of the strength and the elongation, the better the reliability of the cap hole. These results are shown in Table 2.

(resolution)

Further, the resolution was evaluated as follows.

A photo tool having a Stouffer 21-stage stage exposure meter and a wiring pattern having a width/line width of 30/400 to 200/400 (unit: μm) as a negative type negative film for resolution evaluation The photomask was closely adhered and exposed to an energy of 8.0 in the Stouffer 21-stage stage exposure meter after development.

Here, the resolution is evaluated by the development processing capable of completely removing the minimum value (unit: μm) of the interval width between the line widths of the portions which are not photocured. Further, the smaller the numerical value in the evaluation of the resolution, the better.

As can be seen from Table 2, the abnormal shape of the cover holes of Examples 1 to 4 was low, and the values of strength and elongation were large. On the other hand, in Comparative Example 1, the abnormal shape cap hole breaking rate was high, and the values of the strength and the elongation were small. Further, in terms of resolution, Comparative Examples 1 and 2 were inferior to Examples 1 to 4.

Therefore, according to the present invention, it is possible to provide a photosensitive resin composition which is excellent in mechanical strength of a cured film and has flexibility, that is, a photosensitive resin composition excellent in lid hole reliability, and photosensitivity using the photosensitive resin composition. Manufacturing method of component, photoresist pattern, and manufacturing method of printed wiring board.

40‧‧‧Substrate for measuring the number of holes broken

41‧‧‧ round hole

42‧‧3 holes

Fig. 1 is a schematic plan view showing a substrate for measuring the number of cracks in the hole in the embodiment of the present invention.

Fig. 2 is an enlarged view of three connecting holes in the area indicated by A in Fig. 1.

Claims (6)

A photosensitive resin composition containing the following components: (A) component: a binder polymer, (B) component: a polymerizable compound having at least one ethylenically unsaturated bond, and (C) component: photopolymerization initiation And the component (B) contains a compound represented by the following formula (I), (wherein R ¹ represents a divalent organic group, and R ² represents a group represented by the following formula (II)), (wherein R ³ represents a hydrogen atom or a methyl group, X represents an alkylene group, and n represents an integer of 10 to 25). A photosensitive resin composition containing the following components: (A) component: a binder polymer, (B) component: a polymerizable compound having at least one ethylenically unsaturated bond, and (C) component: photopolymerization initiation And the component (B) contains a reaction product of a compound represented by the following formula (III) and a compound represented by the following formula (IV). (wherein R ³ represents a hydrogen atom or a methyl group, X represents an alkylene group, and n represents an integer of 10 to 25), (wherein R ¹ represents a divalent organic group). A photosensitive element comprising: a support, and a photosensitive resin layer formed on the support by a photosensitive resin composition according to claim 1 or 2 of the patent application. A method for producing a resist pattern having a photosensitive resin layer forming step of forming a photosensitive resin layer on a circuit for forming a substrate, the photosensitive resin layer being photosensitive according to claim 1 or 2 The coating film of the resin composition, the active light ray is irradiated to at least a portion of the photosensitive resin layer, the exposure step of the exposed portion is photohardened, and the photosensitive resin layer is removed from the substrate for circuit formation by development The development step of the uncured portion. A method of manufacturing a printed wiring board, comprising: performing an etching treatment or a plating treatment on a circuit for forming a circuit pattern having a photoresist pattern by a manufacturing method of the photoresist pattern of claim 4; The steps of the conductor pattern. A printed wiring board manufactured by the method of manufacturing a printed wiring board according to claim 5 of the patent application.