JP2014196475A - Photosensitive resin composition and cured product of the same, and optical component - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a photosensitive resin composition which can be fast cured by irradiation with light after being applied on a coating target surface to form a cured product having excellent light-shielding property, initial adhesiveness and reflow heat resistance.SOLUTION: A photosensitive resin composition comprises the following components (A), (B) and (C). The component (A): a cationic polymerizable compound containing a compound having an alicyclic epoxy group and no ester bond; the component (B): a photo-cation polymerization initiator comprising an anion moiety having a fluorinated alkyl group and a cation moiety; and the component (C): a light-shielding material.

Description

  The present invention relates to a photosensitive resin composition, a cured product thereof, and an optical component. More specifically, the present invention relates to a photosensitive resin composition and a cured product that can quickly form a light-shielding film or a light-shielding layer by applying light to an optical component such as a lens and irradiating light, and an optical component including the cured product. .

  Currently, demand for portable electronic devices such as mobile phones and smartphones is increasing. Such an electronic apparatus is equipped with a small and thin imaging unit, and the imaging unit is generally composed of a solid-state imaging device (CCD type image sensor, CMOS type image sensor, etc.) and optical components such as a lens. ing. A plurality of lenses are used for the purpose of improving the resolution, and a light shielding film is provided between the plurality of lenses for the purpose of preventing ghosts and flares caused by unnecessary light entering from the outside. . In addition, with the increase in the amount of information transmitted, the role of optical transmission lines such as optical fibers has increased in importance, and in the production of optical modules, by using thermosetting resins and ultraviolet curable resins as adhesives, The connection between the optical core (optical fiber) and the substrate is firmly held. In addition, an adhesive used in manufacturing an optical module (for example, in joining and assembling members) is required to have light shielding properties in addition to excellent adhesiveness.

  Patent Document 1 describes a light-shielding sealant containing a light-shielding material, a curable resin having an unsaturated double bond such as epoxy (meth) acrylate and urethane (meth) acrylate, a polymerization initiator, and a thermosetting agent. ing. However, since the light-shielding sealant contains the light-shielding material that prevents the inside of the curable resin from being irradiated with ultraviolet rays, the curing rate is slow only by ultraviolet irradiation, and it is necessary to perform a long-time heat treatment in addition to ultraviolet irradiation. For example, it took a long time to cure.

  Patent Document 2 describes a light-shielding film obtained by curing a light-shielding paint containing a light-shielding material, an epoxy resin, and an amine curing agent. However, as with the invention described in Patent Document 1, the light-shielding paint cannot be cured quickly by ultraviolet irradiation, and after drying at room temperature for 60 minutes, it is further heated at 80 ° C. for 120 minutes. It was a problem that it took too much.

JP 2006-99027 A JP 2011-186437 A

Accordingly, an object of the present invention is to provide a photosensitive resin composition that can be applied to the surface of an adherend and quickly cured by light irradiation to form a cured product having excellent light shielding properties and initial adhesiveness. Is to provide.
Another object of the present invention is to provide a cured product obtained by curing the photosensitive resin composition, and an optical component including the cured product.

As a result of intensive studies to solve the above problems, the present inventors have found that when a cationically polymerizable compound having an alicyclic epoxy group and having no ester bond is used as the curable compound, an epoxy compound having an ester bond is obtained. It has been found that it is excellent in curability as compared with the case of use and can be cured rapidly by light irradiation.
Further, it has been found that when a specific photocationic polymerization initiator is used, a cured product can be rapidly formed only by light irradiation even when a light-shielding material is contained. The present invention has been completed based on these findings.

That is, this invention provides the photosensitive resin composition containing the following component (A), component (B), and component (C).
Component (A): Cationic polymerizable compound containing a compound having an alicyclic epoxy group and no ester bond Component (B): Photocationic polymerization initiator comprising an anion portion and a cation portion containing a fluorinated alkyl group Component (C): Light-shielding material

［式中、Ｒ¹〜Ｒ¹⁸は同一又は異なって、水素原子、ハロゲン原子、酸素原子若しくはハロゲン原子を含んでいてもよい炭化水素基、又は置換基を有していてもよいアルコキシ基を示す。Ｘは、単結合又は連結基（エステル結合を含む連結基を除く）を示す］ The present invention also provides the photosensitive resin, wherein the compound having an alicyclic epoxy group and not having an ester bond in the component (A) is a compound represented by the following formula (a-1-1): A composition is provided.

[Wherein, R ^{1 to} R ¹⁸ are the same or different and each represents a hydrogen atom, a halogen atom, an oxygen atom, a hydrocarbon group that may contain a halogen atom, or an alkoxy group that may have a substituent. . X represents a single bond or a linking group (excluding a linking group containing an ester bond)]

In the present invention, the anion part of the component (B) is represented by the following formula (b)
[(Rf) _n PF _6-n ] ^- (b)
(In the formula, Rf represents an alkyl group having 1 to 4 carbon atoms in which 80% or more of hydrogen atoms are substituted with fluorine atoms, and n represents an integer of 1 to 5)
The photosensitive resin composition is a fluorinated alkyl fluorophosphate ion represented by:

  The present invention also provides the above photosensitive resin composition, wherein the component (C) is carbon black.

  The present invention also provides a cured product obtained by curing the photosensitive resin composition.

  The present invention also provides an optical component including the cured product.

  Since the photosensitive resin composition of the present invention has the above-described configuration, it can be rapidly cured when applied to the surface of the adherend and irradiated with light to form a cured product having excellent light shielding properties and initial adhesiveness. . Therefore, when the photosensitive resin composition of the present invention is used as an adhesive, the lens and the lens are quickly bonded and fixed by applying between the plurality of lenses constituting the imaging unit of the electronic device and irradiating light. At the same time, a light shielding layer can be formed between the lenses. Moreover, when the photosensitive resin composition of this invention is used for manufacture of an electronic device, a work process can be shortened and productivity can be improved remarkably. In addition, conventionally, the light shielding film was bonded to the lens through the adhesive layer. However, when the photosensitive resin composition of the present invention is used, a cured product having the functions of the light shielding film and the adhesive layer is formed. Therefore, it is possible to achieve further slimming of the photographing unit.

The photosensitive resin composition of this invention contains the following component (A), component (B), and component (C).
Component (A): Cationic polymerizable compound containing a compound having an alicyclic epoxy group and no ester bond Component (B): Photocationic polymerization initiator comprising an anion portion and a cation portion containing a fluorinated alkyl group Component (C): Light-shielding material

(Component (A): Cationic polymerizable compound)
The component (A) of the present invention is one of the curable compounds contained in the photosensitive resin composition, and is a compound having one or more alicyclic epoxy groups in one molecule and having no ester bond (hereinafter referred to as “ester”). , Sometimes referred to as “alicyclic epoxy compound”). Since the photosensitive resin composition of this invention contains a component (A), it is excellent in sclerosis | hardenability. In the present specification, the “alicyclic epoxy group” is a group in which two adjacent carbon atoms constituting an alicyclic ring form a ring together with one oxygen atom. The alicyclic epoxy compound is excellent in curability.

  As said alicyclic epoxy group, the epoxy group etc. which are comprised by two adjacent carbon atoms and oxygen atoms which comprise a cyclohexane ring can be mentioned, for example.

  The said alicyclic epoxy compound should just have 1 or more (for example, 1-6) of alicyclic epoxy groups in 1 molecule, and it has 2-5 pieces, especially 2 in particular. Is preferred.

As said alicyclic epoxy compound, the compound represented by a following formula (a-1-1) can be mentioned, for example. In the formula, R ^{1 to} R ¹⁸ are the same or different and each represents a hydrogen atom, a halogen atom, an oxygen atom, a hydrocarbon group that may contain a halogen atom, or an alkoxy group that may have a substituent. X represents a single bond or a linking group (excluding a linking group containing an ester bond).

As a halogen atom in R < ¹ > -R < ¹⁸ >, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. can be mentioned, for example.

Examples of the hydrocarbon group in R ^{1 to} R ¹⁸ include an aliphatic hydrocarbon group (an alkyl group, an alkenyl group, an alkynyl group, etc.), an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a combination of two or more thereof. The group which was made can be mentioned.

Examples of the alkyl group include C _1-20 alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, hexyl, octyl, isooctyl, decyl and dodecyl groups (preferably C _1-10 alkyl groups, particularly preferably C _1-4 alkyl group). Examples of the alkenyl group include vinyl, allyl, methallyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 5 A C _2-20 alkenyl group such as a hexenyl group (preferably a C _2-10 alkenyl group, particularly preferably a C _2-4 alkenyl group). Examples of the alkynyl group include C _2-20 alkynyl groups (preferably C _2-10 alkynyl groups, particularly preferably C _2-4 alkynyl groups) such as ethynyl and propynyl groups.

Examples of the alicyclic hydrocarbon group include C _3-12 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclododecyl groups; C _3-12 cycloalkenyl groups such as cyclohexenyl groups; and bicycloheptanyl. And a C _4-15 bridged cyclic hydrocarbon group such as a bicycloheptenyl group.

Examples of the aromatic hydrocarbon group include C _6-14 aryl groups (preferably C _6-10 aryl groups) such as phenyl and naphthyl groups.

Examples of the group in which two or more groups selected from the above aliphatic hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group are bonded include, for example, C _3-12 cyclohexane such as cyclohexylmethyl group. Alkyl substituted C _1-20 alkyl group; C _1-20 alkyl substituted C _3-12 cycloalkyl group such as methylcyclohexyl group; C _7-18 aralkyl group such as benzyl group and phenethyl group (especially C _7-10 aralkyl group) C _6-14 aryl substituted C _2-20 alkenyl group such as cinnamyl group; C _1-20 alkyl substituted C _6-14 aryl group such as tolyl group; C _2-20 alkenyl substituted C _6-14 such as styryl group An aryl group etc. can be mentioned.

Examples of the hydrocarbon group that may contain an oxygen atom or a halogen atom in R ^{1 to} R ¹⁸ include a group in which at least one hydrogen atom in the above-described hydrocarbon group is substituted with a group having an oxygen atom or a halogen atom, etc. Can be mentioned. Examples of the group having an oxygen atom include hydroxyl group; hydroperoxy group; C _1-10 alkoxy group such as methoxy, ethoxy, propoxy, isopropyloxy, butoxy, isobutyloxy group; C _2-10 such as allyloxy group. An alkenyloxy group; a C _6-14 aryloxy group optionally having a substituent selected from a C _1-10 alkyl group, a C _2-10 alkenyl group, a halogen atom, and a C _1-10 alkoxy group (for example, C _7-18 aralkyloxy groups such as benzyloxy and phenethyloxy groups; C _1-10 acyloxy groups such as acetyloxy, propionyloxy, (meth) acryloyloxy and benzoyloxy groups; methoxy carbonyl, ethoxycarbonyl, propoxycarbonyl, C _1-10 aralkyl such as a butoxycarbonyl group Alkoxycarbonyl group; C _1-10 alkyl group, C _2-10 alkenyl group, a halogen atom, and C _1-10 may have a substituent group selected from an alkoxy group C _6-14 aryloxycarbonyl group ( For example, phenoxycarbonyl, tolyloxycarbonyl, naphthyloxycarbonyl group, etc.); C _7-18 aralkyloxycarbonyl group such as benzyloxycarbonyl group; epoxy group-containing group such as glycidyloxy group; oxetanyl group such as ethyloxetanyloxy group Groups: C _1-10 acyl groups such as acetyl, propionyl and benzoyl groups; isocyanate groups; sulfo groups; carbamoyl groups; oxo groups; and two or more of these via or without C _1-10 alkylene groups Examples thereof include a bonded group.

Examples of the alkoxy group in R ^{1 to} R ¹⁸ include C _1-10 alkoxy groups such as methoxy, ethoxy, propoxy, isopropyloxy, butoxy, and isobutyloxy groups.

Examples of the substituent that the alkoxy group may have include, for example, a halogen atom, a hydroxyl group, a C _1-10 alkoxy group, a C _2-10 alkenyloxy group, a C _6-14 aryloxy group, a C _1-10 Acyloxy group, mercapto group, C _1-10 alkylthio group, C _2-10 alkenylthio group, C _6-14 arylthio group, C _7-18 aralkylthio group, carboxyl group, C _1-10 alkoxycarbonyl group, C _{6- 14} aryloxycarbonyl group, C _7-18 aralkyloxycarbonyl group, amino group, mono or di C _1-10 alkylamino group, C _1-10 acylamino group, epoxy group-containing group, oxetanyl group-containing group, C _1-10 Examples include an acyl group, an oxo group, and a group in which two or more of these are bonded through or without a C _1-10 alkylene group.

R ^{1 to} R ¹⁸ are preferably hydrogen atoms.

X in the above formula (a-1-1) represents a single bond or a linking group (a divalent group having one or more atoms). However, groups containing an ester bond are excluded from the linking group. Examples of the linking group include a divalent hydrocarbon group, a carbonyl group, an ether bond, an amide group, and a group in which a plurality of these are linked. Examples of the divalent hydrocarbon group include linear or branched C _1-18 alkylene groups such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, and trimethylene groups; 1,2-cyclopentylene, A divalent C _3-12 cycloalkylene group such as 1,3-cyclopentylene, cyclopentylidene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, cyclohexylidene group; And a divalent C _3-12 cycloalkylidene group.

  As the compound represented by the above formula (a-1-1), (3,4,3 ′, 4) is particularly preferable in that the steric hindrance is small and the curing reaction can proceed rapidly by light irradiation. '-Diepoxy) bicyclohexyl is preferred.

  The alicyclic epoxy compound is, for example, a carbon-carbon unsaturated disulfide of a corresponding olefin compound (an olefin compound having the same number of carbon-carbon unsaturated double bonds as the alicyclic epoxy group of the alicyclic epoxy compound). It can be produced by epoxidizing heavy bonds. The epoxidation reaction can be carried out by a known or conventional method. Commercially available alicyclic epoxy compounds may be used.

For example, the compound represented by the above formula (a-1-1) can be produced by epoxidizing the olefin represented by the formula (a-1-1 ′). Incidentally, R ¹ to R ^18, X in formula (a-1-1 ') is the same as R ¹ to R ^18, X in formula (a-1-1).

  As the epoxidizing agent used in the epoxidation reaction, a known or conventional oxidizing agent (for example, organic percarboxylic acids, hydroperoxides, etc.) can be used. Examples of the organic percarboxylic acids include performic acid, peracetic acid, perpropionic acid, perbenzoic acid, trifluoroperacetic acid, and perphthalic acid. Examples of the hydroperoxides include hydrogen peroxide, tertiary butyl hydroperoxide, cumene hydroperoxide, and the like.

  In addition to the compound represented by the above formula (a-1-1), the alicyclic epoxy compound of the present invention has, for example, an alicyclic epoxy group in the molecule, and further has a siloxane bond (Si— And a compound having a siloxane skeleton composed of (O—Si) (= siloxane compound).

  Examples of the siloxane skeleton include a cyclic siloxane skeleton and a polysiloxane skeleton [for example, linear or branched silicone (linear or branched polysiloxane), cage-type or ladder-type polysilsesquioxane. Etc.].

  As the siloxane compound of the present invention, among them, a compound having a cyclic siloxane skeleton represented by the following formula (a-1-2) is preferable in that it is excellent in curability and the resulting cured product is particularly excellent in heat resistance. .

In the above formula (a-1-2), R ¹⁹ and R ²⁰ represent a monovalent group or an alkyl group containing an alicyclic epoxy group. However, at least one of t R ¹⁹ and t R ^{20 in} the compound represented by the formula (a-1-2) is a monovalent group containing an alicyclic epoxy group. Moreover, t in Formula (a-1-2) represents an integer of 3 or more. R ¹⁹ and R ²⁰ in the compound represented by the formula (a-1-2) may be the same or different. The plurality of R ¹⁹ may be the same or different, and the plurality of R ²⁰ may be the same or different.

  In the formula (a-1-2), t represents an integer of 3 or more. Among them, an integer of 3 to 6 is preferable in that the curability of the photosensitive resin composition and the heat resistance and mechanical strength of the cured product are excellent. preferable.

  The number of alicyclic epoxy groups in the molecule of the siloxane compound is preferably 2 to 6 in view of curability of the photosensitive resin composition, heat resistance of the cured product and mechanical strength, and particularly preferably 2 to 4 , Most preferably 3-4.

  The epoxy equivalent (based on JIS K7236) of the siloxane compound is preferably 180 to 400, particularly preferably 240 to 400, most preferably 240 to 400 in terms of excellent curability of the photosensitive resin composition and heat resistance of the cured product. 350.

  Examples of the siloxane compound include 2,4-di [2- (3- {oxabicyclo [4.1.0] heptyl}) ethyl] -2,4,6,6,8,8-hexamethyl-cyclotetra. Siloxane, 4,8-di [2- (3- {oxabicyclo [4.1.0] heptyl}) ethyl] -2,2,4,6,6,8-hexamethyl-cyclotetrasiloxane, 2,4 -Di [2- (3- {oxabicyclo [4.1.0] heptyl}) ethyl] -6,8-dipropyl-2,4,6,8-tetramethyl-cyclotetrasiloxane, 4,8-di [2- (3- {Oxabicyclo [4.1.0] heptyl}) ethyl] -2,6-dipropyl-2,4,6,8-tetramethyl-cyclotetrasiloxane, 2,4,8-tri [2- (3- {Oxabicyclo [4.1.0] heptyl }) Ethyl] -2,4,6,6,8-pentamethyl-cyclotetrasiloxane, 2,4,8-tri [2- (3- {oxabicyclo [4.1.0] heptyl}) ethyl]- 6-propyl-2,4,6,8-tetramethyl-cyclotetrasiloxane, 2,4,6,8-tetra [2- (3- {oxabicyclo [4.1.0] heptyl}) ethyl]- Examples include 2,4,6,8-tetramethyl-cyclotetrasiloxane and silsesquioxane having an alicyclic epoxy group.

More specifically, a compound having a cyclic siloxane skeleton represented by the following formula can be exemplified.

  In addition, in the photosensitive resin composition of this invention, a siloxane compound can be used individually by 1 type or in combination of 2 or more types. As the siloxane compound, for example, commercially available products such as trade names “X-40-2678”, “X-40-2670”, “X-40-2720” (manufactured by Shin-Etsu Chemical Co., Ltd.) are used. You can also.

  In a component (A), an alicyclic epoxy compound can be used individually by 1 type or in combination of 2 or more types.

  Component (A) may contain one or more cationically polymerizable compounds other than the above alicyclic epoxy compounds (hereinafter may be referred to as “other cationically polymerizable compounds”). Examples of other cationic polymerizable compounds include compounds containing, for example, an epoxy group, an oxetanyl group, a vinyl ether group, etc. as the cationic polymerizable group. That is, examples of other cationically polymerizable compounds include epoxy compounds other than the above alicyclic epoxy compounds, compounds having one or more oxetanyl groups in the molecule, compounds having one or more vinyl ether groups in the molecule, and the like. be able to. Other cationic polymerizable compounds may have, for example, a hydroxyl group, a carboxyl group, an ether bond, an ester bond, and the like in addition to the cationic polymerizable functional group.

  Other epoxy compounds include, for example, epoxy compounds having an alicyclic structure in the molecule; aromatic glycidyl ether type epoxy compounds such as bisphenol A type epoxy compounds and bisphenol F type epoxy compounds; mono or poly of aliphatic polyhydric alcohols Aliphatic glycidyl ether-based epoxy compounds such as glycidyl ether; glycidyl ester-based epoxy compounds; glycidyl amine-based epoxy compounds; compounds in which a part of the double bond of a molecular chain having a polybutadiene skeleton or a polyisoprene skeleton is epoxidized be able to.

  The epoxy compound having an alicyclic structure in the molecule includes (i) a compound in which an epoxy group is directly bonded to the alicyclic ring with a single bond (for example, a compound represented by the following formula (a-2)) (Ii) a hydrogenated glycidyl ether epoxy compound obtained by hydrogenating an aromatic glycidyl ether epoxy compound, and (iii) a compound having an alicyclic epoxy group and an ester bond.

R ′ in the formula (a-2) represents a group obtained by removing p —OH from a p-valent alcohol. P and k each represent a natural number. p is preferably 1 to 6, and k is preferably 1 to 30. Examples of the p-valent alcohol [R ′-(OH) _p ] include C _1-15 polyhydric alcohols such as 2,2-bis (hydroxymethyl) -1-butanol. When p is 2 or more, k in the group in parentheses may be the same or different. Examples of the compound represented by the formula (a-2) include 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol [for example, trade name “EHPE3150” (manufactured by Daicel Corporation) and the like can be suitably used.

  As a compound in which a part of the double bond of the molecular chain having the polybutadiene skeleton or the polyisoprene skeleton is epoxidized, for example, a trade name “Epolide PB3600” (manufactured by Daicel Corporation) is available as a commercial product. is there.

  Moreover, when using the epoxy compound which contains an ester bond in a molecule | numerator as another epoxy compound, the usage-amount of the epoxy compound which contains an ester bond in a molecule | numerator is 40 weight% or less of a component (A) whole quantity (100 weight%) ( It is preferably 30% by weight or less, particularly preferably less than 10% by weight, and most preferably less than 5% by weight. If the content of the epoxy compound containing an ester bond in the molecule exceeds the above range, the curability tends to decrease and the heat resistance of the resulting cured product tends to decrease. Moreover, since the epoxy compound which contains an ester bond in a molecule | numerator is easy to be hydrolyzed, there exists a tendency for the water resistance of the hardened | cured material obtained to fall.

  Examples of the compound having one or more oxetanyl groups in the molecule include 3,3-bis (vinyloxymethyl) oxetane, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3- (2-ethylhexyl). Oxymethyl) oxetane, 3-ethyl-3-[(phenoxy) methyl] oxetane, 3-ethyl-3- (hexyloxymethyl) oxetane, 3-ethyl-3- (chloromethyl) oxetane, 3,3-bis ( Chloromethyl) oxetane, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, bis ([1-ethyl (3-oxetanyl)] methyl) ether, 4,4′-bis [(3 -Ethyl-3-oxetanyl) methoxymethyl] bicyclohexyl, 1,4-bis [(3-ethyl-3-oxetanyl) me Xylmethyl] cyclohexane, 1,4-bis ([(3-ethyl-3-oxetanyl) methoxy] methyl) benzene, 3-ethyl-3 ([(3-ethyloxetan-3-yl) methoxy] methyl) oxetane, xyl Renbisoxetane and the like can be mentioned. In the present invention, for example, commercially available products such as trade names “OXT221” and “OXT121” (manufactured by Toagosei Co., Ltd.) can be used.

  Examples of the compound having one or more vinyl ether groups in the molecule include 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 2-hydroxypropyl vinyl ether, 2-hydroxyisopropyl vinyl ether, 4-hydroxybutyl vinyl ether, 3- Hydroxybutyl vinyl ether, 2-hydroxybutyl vinyl ether, 3-hydroxyisobutyl vinyl ether, 2-hydroxyisobutyl vinyl ether, 1-methyl-3-hydroxypropyl vinyl ether, 1-methyl-2-hydroxypropyl vinyl ether, 1-hydroxymethylpropyl vinyl ether, 4 -Hydroxycyclohexyl vinyl ether, 1,6-hexanediol monovinyl ether, 1,4-cyclohexane Methanol monovinyl ether, 1,3-cyclohexanedimethanol monovinyl ether, 1,2-cyclohexanedimethanol monovinyl ether, p-xylene glycol monovinyl ether, m-xylene glycol monovinyl ether, o-xylene glycol monovinyl ether, diethylene glycol monovinyl ether, tri Ethylene glycol monovinyl ether, tetraethylene glycol monovinyl ether, pentaethylene glycol monovinyl ether, oligoethylene glycol monovinyl ether, polyethylene glycol monovinyl ether, dipropylene glycol monovinyl ether, tripropylene glycol monovinyl ether, tetrapropylene glycol monovinyl ether, pentapropylene Glycol monovinyl ether, oligo propylene glycol monomethyl ether, polypropylene glycol monovinyl ether, and may be derivatives thereof.

  As the component (A) of the present invention, it is particularly preferable to contain a compound having one or more oxetanyl groups in the molecule together with the alicyclic epoxy compound from the viewpoint that the initial adhesive force can be improved. .

  In addition, as the component (A) of the present invention, as another epoxy compound, an epoxy compound having an alicyclic structure in the molecule and not having an aromatic ring structure and an ester bond and / or a polybutadiene skeleton or a polyisoprene skeleton are used. It is preferable that a part of the double bond of the molecular chain has an epoxidized compound from the viewpoint that the degree of crosslinking of the resulting cured product can be increased and the mechanical strength can be improved.

  The content of the component (A) in the total amount (100% by weight) of the photosensitive resin composition of the present invention is, for example, about 40 to 99% by weight, preferably 50 to 98% by weight, particularly preferably 60 to 97% by weight. . When content of a component (A) is less than the said range, sclerosis | hardenability will fall and it will become difficult to obtain initial adhesiveness. On the other hand, when content of a component (A) exceeds the said range, there exists a tendency for sclerosis | hardenability to fall and it becomes difficult to obtain sufficient adhesiveness.

  The content of the alicyclic epoxy compound in the total amount (100% by weight) of component (A) (the total amount when containing two or more types) is, for example, about 20 to 95% by weight, preferably 30 to 90% by weight. Particularly preferred is 35 to 85% by weight. When content of an alicyclic epoxy compound is less than the said range, sclerosis | hardenability will fall and there exists a tendency for initial stage adhesiveness to become difficult to be obtained.

  The content of other epoxy compounds in the total amount (100% by weight) of component (A) (the total amount when containing two or more) is, for example, about 10 to 70% by weight, preferably 15 to 65% by weight, Preferably it is 20 to 60 weight%. When other epoxy compounds are contained in the above range, flexibility and toughness can be imparted to the resulting cured product.

  The content of the compound having one or more oxetanyl groups in the molecule in the total amount (100% by weight) of component (A) is, for example, about 1 to 35% by weight, preferably 5 to 30% by weight, particularly preferably 10 to 25%. % By weight.

(Ingredient (B))
Component (B) of the present invention is a cationic photopolymerization initiator that generates an acid upon irradiation with light and initiates the curing reaction of the cationically polymerizable compound contained in the photosensitive resin composition, and is a cation that absorbs light. Part and an anion part which is a source of acid.

  In the present invention, a photocationic polymerization initiator composed of an anion portion and a cation portion containing a fluorinated alkyl group is used. Therefore, even when the cationic polymerizable compound coexists with the light-shielding material, the curing reaction can be promptly accelerated by light irradiation, and a cured product having excellent light-shielding properties and initial adhesiveness can be formed. Can do. A photocationic polymerization initiator can be used individually by 1 type or in combination of 2 or more types.

Examples of the anion part containing a fluorinated alkyl group in the photocationic polymerization initiator include the following formula (b):
[(Rf) _n PF _6-n ] ^- (b)
(In the formula, Rf represents an alkyl group having 1 to 4 carbon atoms in which 80% or more of hydrogen atoms are substituted with fluorine atoms, and n represents an integer of 1 to 5)
And fluorinated alkyl fluorophosphate ions, CF ₃ SO ₃ ⁻ , C ₄ F ₉ SO ₃ ⁻ , B (C ₆ F ₅ ) ₄ ^{− and the} like. In the present invention, the fluorinated alkyl fluorophosphate ion represented by the formula (b) is particularly preferable in terms of excellent safety and cationic polymerization activity.

In the formula (b), Rf is an alkyl group having 1 to 4 carbon atoms in which 80% or more of hydrogen atoms are substituted with fluorine atoms, and among them, CF ₃ , C ₂ F ₅ , (CF ₃ ) ₂ CF , C ₃ F ₇ , C ₄ F ₉ , (CF ₃ ) ₂ CFCF ₂ , CF ₃ CF ₂ (CF ₃ ) CF, (CF ₃ ) ₃ C, etc., 100% of hydrogen atoms were replaced with fluorine atoms A linear or branched C _1-4 alkyl group is preferred.

Therefore, the anionic part of the photocationic polymerization initiator is particularly [(C ₂ F ₅ ) ₃ PF ₃ ] ⁻ , [(C ₃ F ₇ ) ₃ PF ₃ ] ⁻ , [((CF ₃ ) ₂ CF). ₃ PF ₃ ] ⁻ , [((CF ₃ ) ₂ CF) ₂ PF ₄ ] ⁻ , [((CF ₃ ) ₂ CFCF ₂ ) ₃ PF ₃ ] ⁻ , and [((CF ₃ ) ₂ CFCF ₂ ) ₂ PF _4] ^-, and the like are preferable.

  As a cation part in a photocationic polymerization initiator, an iodonium ion, a sulfonium ion, etc. can be mentioned, for example.

  Among the iodonium ions, aryl iodonium ions are preferable, and bisaryl iodonium ions are particularly preferable. The sulfonium ion is preferably an arylsulfonium ion, and particularly preferably a triarylsulfonium ion.

  Examples of the iodonium ion include diphenyliodonium ion, di-p-tolyliodonium ion, bis (4-dodecylphenyl) iodonium ion, bis (4-methoxyphenyl) iodonium ion, and (4-octyloxyphenyl) phenyliodonium ion. Bis (4-decyloxy) phenyliodonium ion, 4- (2-hydroxytetradecyloxyphenyl) phenyliodonium ion, 4-isopropylphenyl (p-tolyl) iodonium ion, and 4-isobutylphenyl (p-tolyl) iodonium ion Aryliodonium ions such as bisaryliodonium ions.

  Examples of the sulfonium ion include arylsulfonium ions (particularly, triarylsulfonium ions) such as triphenylsulfonium ions, diphenyl [4- (phenylthio) phenyl] sulfonium ions, and tri-p-tolylsulfonium ions. it can.

  Examples of the photocationic polymerization initiator of the present invention include 4-isopropylphenyl (p-tolyl) iodonium tris (pentafluoroethyl) trifluorophosphate, [1,1′-biphenyl] -4-yl [4- (1,1 '-Biphenyl) -4-ylthiophenyl] phenyl tris (pentafluoroethyl) trifluorophosphate, diphenyl (4-phenylthio) phenylsulfonium tetrakis (pentafluorophenyl) phosphate, and the like can be suitably used.

  The content of the component (B) is, for example, about 0.1 to 30 parts by weight, preferably 0.5 to 25 parts by weight, particularly 100 parts by weight of the cationically polymerizable compound contained in the photosensitive resin composition. Preferably it is 1-20 weight part. When content of a component (B) is less than the said range, there exists a tendency for sclerosis | hardenability to fall. On the other hand, when content of a component (B) exceeds the said range, there exists a tendency for the storage stability of a composition to fall. The photosensitive resin composition of the present invention may contain a photopolymerization initiator other than the component (B), but the content of the other photopolymerization initiator is in the photosensitive resin composition. In the total photopolymerization initiator (100% by weight) contained, for example, it is 70% by weight or less, preferably 60% by weight or less, particularly preferably 50% by weight or less. When the content of other photopolymerization initiators exceeds the above range, curability tends to decrease.

(Ingredient (C))
Component (C) of the present invention is a light-shielding material, and is a material that imparts light-shielding properties by being dispersed in the photosensitive resin composition and its cured product. In the present invention, pigments and dyes can be preferably used.

  Examples of the pigment include inorganic pigments [carbon black, chromium oxide, iron oxide, titanium black, acetylene black, lamp black, bone black, graphite, iron black, copper chrome black, copper iron manganese black, cobalt iron chrome. Black, ruthenium oxide, graphite, metal fine particles, metal oxide fine particles, composite oxide fine particles, metal sulfide fine particles, metal nitride fine particle and other black inorganic pigments], organic pigments [perylene black, cyanine black, aniline black, etc. Black organic pigments: pigments exhibiting red, blue, green, purple, yellow, cyan, magenta, etc. (for example, azo pigments, phthalocyanine pigments, quinacridone pigments, benzimidazolone pigments, isoindolinone pigments) , Dioxazine pigments, indanthrene pigments, perylene pigments ) Two or more color mixing to pseudo blackened color mixing organic pigments obtained]; the surface of the inorganic pigments such as carbon black or titanium black and pigment coated with an organic material such as resin. These can be used alone or in combination of two or more.

  Examples of the dye include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinoneimine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methine dyes. These can be used alone or in combination of two or more.

  In the present invention, among them, a pigment (particularly carbon black) is preferable in terms of excellent dispersibility, light shielding properties, and durability.

  The average particle diameter of the light-shielding material (by the dynamic light scattering measurement method) is preferably about 5 to 500 nm, for example. When the average particle diameter exceeds the above range, the light shielding property tends to be lowered. On the other hand, when the average particle size is below the above range, aggregation tends to occur and it tends to be difficult to achieve high dispersion.

  The content of the component (C) is, for example, about 0.05 to 50 parts by weight, preferably 0.1 to 30 parts by weight, particularly preferably 0.3 to 20 parts by weight with respect to 100 parts by weight of the curable compound. is there. When the content of the component (C) is below the above range, sufficient light shielding properties tend to be difficult to obtain. On the other hand, when content of a component (C) exceeds the said range, there exists a tendency for the viscosity of a composition to rise and for workability | operativity to fall.

  The photosensitive resin composition of the present invention may contain other components in addition to the components (A) to (C) as long as the effects of the present invention are not impaired.

  The photosensitive resin composition of this invention may contain compounds other than the said component (A) as a sclerosing | hardenable compound, for example, containing 1 type, or 2 or more types of hydroxyl-containing compounds is reflow heat resistance. It is preferable at the point which can obtain the hardened | cured material which has. The hydroxyl group-containing compound is a compound containing 2 or more (particularly preferably 2) hydroxyl groups in one molecule. For example, (i) a hydroxyl group-containing compound having a polycarbonate skeleton in the molecule, and (ii) a polyester in the molecule. A hydroxyl group-containing compound having a skeleton, (iii) a hydroxyl group-containing compound having a polydiene skeleton in the molecule, (iv) a hydrocarbon skeleton in the molecule, or two or more hydrocarbon skeletons, a nitrogen atom, a sulfur atom, and an oxygen atom And a hydroxyl group-containing compound having a skeleton bonded through a heteroatom selected from the group consisting of

  The hydroxyl group-containing compound has a curing accelerating action, imparts reflow heat resistance and flexibility to the resulting cured product, and follows the surface shape of the adherend well, improving the adhesion to the adherend. Has the effect of

  (I) A hydroxyl group-containing compound having a polycarbonate skeleton in the molecule is a phosgene method, or a transesterification reaction between a dialkyl carbonate (for example, dimethyl carbonate, diethyl carbonate, etc.) or diphenyl carbonate and a polyol (Japanese Patent Laid-Open No. 62-187725, (See JP-A-2-175721, JP-A-2-49025, JP-A-3-220233, JP-A-3-252420).

  Examples of the polyol used in the transesterification include 1,6-hexanediol, ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 2,3- Butanediol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,4-cyclohexanedimethanol, 1,12-dodecanediol, polybutadienediol, neopentyl glycol, tetramethylene glycol, propylene glycol, Dipropylene glycol, glycerin, trimethylolpropane, 1,3-dihydroxyacetone, hexylene glycol, 1,2,6-hexanetriol, ditrimethylolpropane, trimethylolethane, trimethyloloctane, Mention may be made of pentaerythritol and the like. Also, ester glycol (manufactured by Mitsubishi Gas Chemical Co., Inc.), polyester polyol, and polyether polyol can be used.

  Examples of the hydroxyl group-containing compound having a polycarbonate skeleton in the molecule include, for example, trade names “Placcel CD205”, “Plaxel CD205PL”, “Plaxel CD205HL”, “Plaxel D210”, “Plaxel CD210PL”, “Plaxel CD210HL”, “Plaxel CD220” ", Plaxel CD220PL", "Plaxel CD220HL", "Plaxel CD220EC", "Plaxel CD221T" (manufactured by Daicel Corporation) and trade names "UM-CARB90 (1/3)", "UM-CARB90 (1 / 1) "," UC-CARB100 "(manufactured by Ube Industries, Ltd.) and the like are commercially available.

  (Ii) A hydroxyl group-containing compound having a polyester skeleton in the molecule can be synthesized by reacting a polyol and a carboxylic acid. In addition, it can be synthesized by ring-opening polymerization of lactones.

  Examples of the polyol used as a raw material for the hydroxyl group-containing compound having a polyester skeleton in the molecule include the same examples as the polyol used in the transesterification reaction.

  Examples of the carboxylic acid used as a raw material for the hydroxyl group-containing compound having a polyester skeleton in the molecule include oxalic acid, adipic acid, sebacic acid, fumaric acid, malonic acid, succinic acid, glutaric acid, azelaic acid, citric acid, 2 , 6-Naphthalenedicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid, citraconic acid, 1,10-decanedicarboxylic acid, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride Products, pyromellitic anhydride, trimellitic anhydride, lactic acid, malic acid, glycolic acid, dimethylolpropionic acid, dimethylolbutanoic acid and the like.

  Examples of the lactones include ε-caprolactone, δ-valerolactone, γ-butyrolactone, and the like.

  Examples of the hydroxyl group-containing compound having a polyester skeleton in the molecule include trade names “Placcel 205U”, “Plaxel L205AL”, “Plaxel L208AL”, “Plaxel L212AL”, “Plaxel L220AL”, “Plaxel L230AL”, “Plaxel” 220ED "," Placcel 220EC "," Placcel 220EB "," Placcel 303 "," Placcel 305 "," Placcel 308 "," Placcel 312 "," Placcel L312AL "," Placcel 320 "," Placcel L320AL "," Placcel " 320ML ”,“ Plaxel 410 ”,“ Plaxel 410D ”,“ Plaxel P3403 ”,“ Plaxel E227 ”,“ Plaxel DC2009 ”,“ Plaxel DC2016 ”,“ Placel ” Kuseru DC2209 "(or more, (Ltd.) manufactured by Daicel) is available as and, trade name" Kuraray Polyol P-510 "(manufactured by Kuraray Co., Ltd.) and the like are commercially available.

  As the hydroxyl group-containing compound having a polyester skeleton in the molecule, a hydroxyl group-containing compound obtained by ring-opening polymerization of a lactone (particularly, a hydroxyl group-containing compound having a caprolactone skeleton) is used. It is preferable at the point which can provide property and flexibility.

  (Iii) Examples of the hydroxyl group-containing compound having a polydiene skeleton in the molecule include compounds having a hydroxyl group at both ends of a molecular chain having a polybutadiene skeleton or a polyisoprene skeleton.

  As the hydroxyl group-containing compound having a polydiene skeleton in the molecule, for example, a trade name “Poly ip” (manufactured by Idemitsu Kosan Co., Ltd.) is available as a commercial product.

  (≡) Hydroxyl-containing compound having a skeleton in which a hydrocarbon skeleton or two or more hydrocarbon skeletons are bonded via a heteroatom selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom in the molecule As, for example, an alkyl chain, an alicyclic hydrocarbon skeleton, or a molecular chain having a skeleton in which these are bonded via a heteroatom selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom. The compound which has a hydroxyl group at the terminal can be mentioned.

  As the hydroxyl group-containing compound having a hydrocarbon skeleton in the molecule, for example, a trade name “DEG” (manufactured by Maruzen Petrochemical Co., Ltd.) is available as a commercial product.

  As the hydroxyl group-containing compound in the present invention, among others, (i) the use of a hydroxyl group-containing compound having a polycarbonate skeleton in the molecule may impart reflow heat resistance, flexibility, and toughness to the cured product. It is preferable in that it can be performed.

  The content of the hydroxyl group-containing compound in the total amount of the curable compound contained in the photosensitive resin composition of the present invention (for example, the total amount of the component (A) and the hydroxyl group-containing compound) (100 wt%) is, for example, about 5 to 35 wt%. Preferably it is 3 to 30 weight%, Most preferably, it is 1 to 25 weight%. When the hydroxyl group-containing compound is contained in the above range, an effect of improving initial adhesiveness can be obtained.

  The photosensitive resin composition of the present invention further includes, as other components, a polyhydric alcohol (for example, ethylene glycol, diethylene glycol, propylene glycol, glycerin and the like), a photosensitizer (for example, a thioxanthone compound), and an antifoaming agent. , Leveling agent, coupling agent (for example, silane coupling agent, etc.), surfactant, inorganic filler, flame retardant, ultraviolet absorber, ion adsorbent, phosphor, release agent, pigment dispersant, dispersion aid Conventional additives such as can be used.

  The content of other components (the total amount when two or more are included) is about 10% by weight or less of the total amount (100% by weight) of the photosensitive resin composition.

  In the photosensitive resin composition of the present invention, for example, the above components (A) to (C) and other components as necessary are stirred and mixed at a predetermined ratio, and defoamed under vacuum as necessary. Can be prepared. In order to improve the dispersibility of component (C) (especially pigment), a well-known method (for example, a method using a ball mill, a sand mill, a bead mill, a three roll, a paint shaker, an ultrasonic wave, a bubble homogenizer, etc.) You may perform the distributed processing by.

(Cured product)
The photosensitive resin composition of this invention can form hardened | cured material by irradiating light and advancing the cationic polymerization reaction of the cationically polymerizable compound in a composition. The light (active energy ray) for causing the polymerization reaction to proceed is not particularly limited, and for example, any of infrared rays, visible rays, ultraviolet rays, X rays, electron rays, α rays, β rays, γ rays, etc. are used. You can also Of these, ultraviolet rays are preferable in terms of excellent handleability.

The light irradiation conditions for forming the cured product can be adjusted as appropriate depending on the type and energy of the light to be irradiated, the shape and size of the cured product to be formed, and when irradiating ultraviolet rays, the irradiation intensity for example 0.1~1000mW / cm ² approximately (more preferably 1 to 500 mW / cm ²⁾ is preferable to be, the case of forming a cured product having a thickness of 20 [mu] m, irradiation time, for example, about 1 to 120 seconds, preferably Is 3 to 60 seconds, particularly preferably 5 to 20 seconds. For light irradiation, for example, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a xenon lamp, a carbon arc, a metal halide lamp, sunlight, an LED lamp, a laser, or the like can be used.

Since the photosensitive resin composition of the present invention has the above-described configuration, the curing rate is very fast even if it contains an amount of the component (C) that can provide sufficient light-shielding properties, and it is cured quickly by irradiation with light. And a cured product having excellent curability can be formed. Therefore, the adhesive strength (with respect to the glass plate) when it has excellent initial adhesive strength and irradiated with ultraviolet rays at 200 mW / cm ² for 15 seconds is, for example, 1 MPa or more, preferably 5 MPa or more, particularly preferably 7 MPa or more.

Moreover, the cured product obtained by curing the photosensitive resin composition of the present invention has high light shielding properties, and the light shielding rate of a molded product having a thickness of 20 μm is preferably 85% or more, more preferably 90% or more, Particularly preferred is 95% or more, and most preferred is 96% or more. The light-shielding rate was measured according to JIS K7105 (1981) except that a cured product having a thickness of 20 μm was used as a test piece and the D65 light source was used as the light source. Can be calculated.
Light blocking ratio [%] = 100 [%] − total light transmittance [%]

  The photosensitive resin composition of this invention can be apply | coated to the predetermined position of an optical component, and it hardens | cures rapidly by irradiating light after that, and can form a light shielding film or a light shielding layer. The application of the photosensitive resin composition can be performed by a known or common technique such as dispensing or transfer printing (gravure printing). The shape of the light shielding film or the light shielding layer can be appropriately selected and is not particularly limited.

  The photosensitive resin composition of the present invention can be used, for example, for printing ink, inkjet ink, photomask preparation material, printing proof preparation material, etching resist, solder resist, It can also be used for various applications such as partition walls of plasma display panels, dielectric patterns, electrode (conductor circuit) patterns, wiring patterns of electronic components, conductive pastes, conductive films.

  The photosensitive resin composition of the present invention is also used as an adhesive for optical communication in the assembly of an optical module, such as bonding an optical fiber and a substrate. Specifically, the photosensitive resin composition of the present invention is applied or filled in the gap between the substrate and the optical element, or the gap between the substrate and the optical fiber (optical core wire), and then quickly irradiated with light. It hardens | cures and it becomes possible to join a board | substrate and an optical fiber (optical core wire) firmly.

  The photosensitive resin composition of the present invention can form a cured product having high light-shielding properties quickly, inexpensively and simply by irradiation with light. Therefore, a light shielding film may be formed using the photosensitive resin composition of the present invention, and the obtained light shielding film may be bonded using an adhesive between a plurality of lenses constituting the imaging unit. When the photosensitive resin composition of the present invention is used as an adhesive, it is applied between a plurality of lenses constituting an imaging unit of an electronic device and irradiated with light to quickly adhere and fix the lenses to each other. At the same time, a light shielding layer can be formed between the lenses, so that the work process can be shortened and productivity can be dramatically improved. Furthermore, further slimming of the photographing unit can be achieved.

(Optical parts)
Since the optical component of the present invention contains a cured product having a high light shielding property formed by the photosensitive resin composition of the present invention (for example, as a light shielding film or a light shielding layer), it can exhibit excellent quality.

  The thickness of the cured product in the optical component (for example, the thickness of the light shielding film or the light shielding layer) can be appropriately selected according to the type, size, shape, etc. of the optical component, and is, for example, about 50 μm or less. Since the cured product of the present invention is formed using the above-described photosensitive resin composition, even if it is relatively thick, defects caused by poor curing of the photosensitive resin composition (for example, a decrease in initial adhesive force, heat resistance) Reduction, surface tack, etc.) will not occur.

  Examples of the optical component include known or commonly used optical components. For example, lenses, solid-state imaging devices (CCD image sensors, CMOS image sensors, etc.), touch panels, liquid crystals in the field of portable electronic devices such as mobile phones and smartphones. Examples include a display, a plasma display panel, an LED package, and various electronic components. When the cured product of the present invention is included in the optical component as a light-shielding film or a light-shielding layer, the light-shielding film or the light-shielding layer is, for example, between lenses (parts other than the lens), a part of the lens, or a color filter. It is formed as a light-shielding region in a pattern interval portion or a peripheral portion, a light-shielding region in an LED package, or the like.

  EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited by these Examples.

Examples 1-9, Comparative Examples 1-3
Each component was blended according to the blending composition (unit: parts by weight) shown in the table, and stirred and mixed with a rotation / revolution mixer to obtain a uniform photosensitive resin composition.
About the obtained photosensitive resin composition, the light-shielding property, sclerosis | hardenability, and initial stage adhesiveness were evaluated with the following method. The evaluation results are summarized in the following table.

(1) Evaluation of light shielding properties The photosensitive resin compositions obtained in Examples and Comparative Examples were applied on glass using an applicator, and the glass was covered thereon. Next, the applied photosensitive resin composition was irradiated with ultraviolet rays using an ultraviolet irradiation device (UV or UV-LED irradiation device) (irradiation intensity: 200 mW / cm ² , irradiation time: 15 seconds). A cured product (thickness: 20 μm) / glass laminate was produced.
The obtained glass / cured product / glass laminate was used as a sample, the total light transmittance of the sample was measured, and the light shielding rate was calculated from the following formula.
Light blocking ratio [%] = 100 [%] − total light transmittance [%]
The total light transmittance was measured using a turbidimeter (trade name “NDH2000”, light source: D65 light source, manufactured by Nippon Denshoku Industries Co., Ltd.).

(2) Evaluation of curability The photosensitive resin compositions obtained in Examples and Comparative Examples were applied on a glass with a thickness of 20 μm using an applicator. Next, the coated photosensitive resin composition was irradiated with ultraviolet rays using an ultraviolet irradiation device (UV-LED irradiation device) (irradiation intensity: 200 mW / cm ² , irradiation time: 15 seconds), and cured product / glass. (Thickness: 20 μm) A laminate was produced.
The obtained cured product / glass laminate was used as a sample (number of samples: 20), and the curability was evaluated based on whether or not the swab became black when the cured product surface was rubbed with a cotton swab.
Evaluation criteria ○: When the swab does not become black = sufficiently cured ×: When the swab becomes black = Insufficient curing

(3) Evaluation of initial adhesiveness First, a Teflon (registered trademark) sheet (sheet thickness: 20 μm) having an outer dimension of 45 mm in length × 55 mm in width is formed into a U-shape so that the vertical portion becomes an opening. A spacer (a Teflon (registered trademark) sheet spacer) having a cutout and an inner dimension of 40 mm long × 50 mm wide was formed.
Next, the spacer is sandwiched from above and below by two glass plates (external dimensions: length 45 mm × width 55 mm, thickness: 1 mm), and the photosensitivity obtained in the examples and comparative examples in the gap between the two glass plates. The conductive resin composition was poured and filled. Thereafter, the photosensitive resin composition is irradiated with ultraviolet rays using an ultraviolet irradiation device (UV-LED irradiation device) (irradiation intensity: 200 mW / cm ² , irradiation time: 15 seconds), and the photosensitive resin composition. Was cured, and the obtained glass plate / cured product (thickness: 20 μm) / glass plate laminate was used as a sample.
About the obtained sample, the tensile strength / compression tester (trade name “Tensilon RTF-1350”, manufactured by A & D Co., Ltd.) was used to determine the adhesive strength (adhesive strength) (MPa) in the shear direction between the cured product and the glass plate. And measured.
In addition, when the adhesive strength was strong and the glass plate broke during measurement, it was described as “> 15” (that is, a value exceeding 15 MPa) in the table.

In addition, the component used by the Example and the comparative example is as follows.
<Curable compound>
(Cationically polymerizable compound)
(3,4,3 ′, 4′-diepoxy) bicyclohexyl EHPE3150: 1,2-epoxy-4- (2-oxiranyl) cyclohexene adduct of 2,2-bis (hydroxymethyl) -1-butanol, ( YX8000 manufactured by Daicel Corporation, hydrogenated glycidyl ether type epoxy compound, Celoxide 2021: 3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexanecarboxylate, manufactured by Mitsubishi Chemical Corporation, trade name “Celoxide 2021”, ( OXT221 manufactured by Daicel Corporation: 3-ethyl-3-([(3-ethyloxetane-3-yl) methoxy] methyl) oxetane, manufactured by Toagosei Co., Ltd. PB3600: epoxidized polybutadiene, number average molecular weight: 5900, trade name "Epolide PB3600", manufactured by Daicel Corporation X-40 2670: cyclic siloxane with 2-4 alicyclic epoxy group in the molecule, trade name "X-40-2670", manufactured by Shin-Etsu Chemical Co., Ltd. (hydroxyl group-containing compound)
CD220PL: Polycarbonate diol, number average molecular weight: 2000, trade name “Placcel CD220PL”, manufactured by Daicel Corporation (others)
DEG: Diethylene glycol, trade name "DEG", Maruzen Petrochemical Co., Ltd.
<Photocationic polymerization initiator>
b-1: 4-Isopropylphenyl (p-tolyl) iodonium tris (pentafluoroethyl) trifluorophosphate b-2: [1,1′-biphenyl] -4-yl [4- (1,1′-biphenyl) -4-ylthiophenyl] phenyl tris (pentafluoroethyl) trifluorophosphate b-3: bis (4-tert-butylphenyl) iodonium hexafluorophosphate b-4: diphenyl (4-phenylthio) phenylsulfonium tetrakis (pentafluoro Phenyl) phosphate <Light-shielding material>
Carbon black: average particle size of 24 nm, trade name “MA100R”, manufactured by Mitsubishi Chemical Corporation

Claims (6)

The photosensitive resin composition containing the following component (A), a component (B), and a component (C).
Component (A): Cationic polymerizable compound containing a compound having an alicyclic epoxy group and no ester bond Component (B): Photocationic polymerization initiator comprising an anion portion and a cation portion containing a fluorinated alkyl group Component (C): Light-shielding material The photosensitive resin composition according to claim 1, wherein the compound having an alicyclic epoxy group and having no ester bond in the component (A) is a compound represented by the following formula (a-1-1): .

[Wherein, R ^{1 to} R ¹⁸ are the same or different and each represents a hydrogen atom, a halogen atom, an oxygen atom, a hydrocarbon group that may contain a halogen atom, or an alkoxy group that may have a substituent. . X represents a single bond or a linking group (excluding a linking group containing an ester bond)] The anion part of the component (B) is represented by the following formula (b)
[(Rf) _n PF _6-n ] ^- (b)
(In the formula, Rf represents an alkyl group having 1 to 4 carbon atoms in which 80% or more of hydrogen atoms are substituted with fluorine atoms, and n represents an integer of 1 to 5)
The photosensitive resin composition according to claim 1, which is a fluorinated alkyl fluorophosphate ion represented by the formula:   The photosensitive resin composition according to claim 1, wherein the component (C) is carbon black.   Hardened | cured material obtained by hardening | curing the photosensitive resin composition of any one of Claims 1-4.   An optical component comprising the cured product according to claim 5.