JP2019065175A - Curable composition, cured film, and method for producing cured product - Google Patents

Abstract

To provide a curable composition having excellent refractive indices and yellowing resistance, a cured film comprising a cured product of the curable composition, and a method for producing a cured product using the curable composition.SOLUTION: A cation-curable or anion-curable composition gives a cured film that contains (C) an ionic liquid with a melting point of 140°C or less, and has a refractive index of 1.60 or more and 2.20 or less with respect to light with a wavelength of 550 nm.SELECTED DRAWING: None

Description

  The present invention relates to a curable composition, a cured film comprising a cured product of the above-mentioned curable composition, and a method for producing a cured product using the above-mentioned curable composition.

  Conventionally, a cationically polymerizable curable composition containing a cationically polymerizable compound such as an epoxy compound as a curable component has been used in various applications.

  As such a curable composition, for example, a cationically polymerizable compound containing an aromatic ring-containing alicyclic epoxy compound, a cationically polymerizable compound other than an aromatic ring-containing alicyclic epoxy compound, and a thermal cationic polymerization initiator Thermosetting compositions are known (see Patent Document 1). By using such a curable composition, it is possible to form a cured product having a high glass transition temperature, excellent transparency (heat yellowing and less coloration), and excellent substrate adhesion.

JP, 2014-156522, A International Publication No. 2014/157675

  When the curable composition described in Patent Document 1 is used, it is possible to form a cured product exhibiting high glass transition temperature and having good heat resistance from the viewpoint of thermal deformation. However, there is still room for improvement in achieving both high refractive index and thermal yellowing, particularly thermal yellowing.

Also, conventionally, in order to form a cured product having a high refractive index, a material having a structure that contributes to the improvement of the refractive index, such as an aromatic hydrocarbon group or a triazine ring, has often been used (for example, patent documents 2).
On the other hand, in the case of a cured product formed using a curable composition containing a material containing an aromatic hydrocarbon group or a triazine ring, light or heat is generated due to the presence of the aromatic hydrocarbon group or the triazine ring or the like. Was apt to cause yellowing due to That is, for the conventional curable composition used to form a cured product having a high refractive index, there is a trade-off relationship in which one increases and the other decreases with respect to the refractive index of the cured product and the yellowing resistance of the cured product. There was a big problem in the

  This invention is made in view of said subject, Comprising: The curable composition which can form the cured | curing material which is excellent in a refractive index and yellowing resistance, and the cured film which consists of a cured | curing material of the said curable composition An object of the present invention is to provide a method for producing a cured product using the above-mentioned curable composition.

(C) The ionic liquid has good ionic conductivity, and by being liquid with a melting point of 140 ° C. or less, it can be uniformly diffused in the curable composition. The (C) ionic liquid also has a relatively high thermal decomposition temperature.
The present inventors have low dependency on whether it is cationic polymerization or anionic polymerization in the curable composition containing (C) ionic liquid, and can uniformly accelerate the curing reaction, as a result, We found that we could solve the problem of The present invention has been achieved based on the above findings. That is, the present invention is as follows.

A first aspect of the present invention is a cationic curable or anionic curable curable composition,
The curable composition is a curable composition containing (C) an ionic liquid having a melting point of 140 ° C. or less and giving a cured film having a refractive index of 1.60 or more and 2.20 or less for light having a wavelength of 550 nm. .

A second aspect of the present invention is a cationic curable or anionic curable curable composition, wherein
Curable composition containing (A) a curable compound having a functional group containing at least one element selected from the group consisting of N, O, S and Si, and (C) an ionic liquid having a melting point of 140 ° C. or less The curable composition according to claim 1, wherein the curable compound (A) comprises at least one selected from the group consisting of an aromatic group, a triazine ring structure, an isocyanuric ring structure and a cyclic siloxane structure.

  A third aspect of the present invention is a cured film comprising a cured product of the curable composition according to the first or second aspect.

The fourth aspect of the present invention is
Molding the curable composition according to the first aspect into a predetermined shape;
Heating, exposing, or performing exposure and heating on the formed curable composition;
A method of producing a cured product comprising

The curable composition of the present invention can form a cured product excellent in refractive index and yellowing resistance.
Moreover, according to this invention, the cured film which consists of hardened | cured material of the said curable composition, and the manufacturing method of the hardened | cured material using the above-mentioned curable composition can be provided. The above-mentioned cured product is suitable for various uses.

Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments at all, and can be implemented with appropriate modifications within the scope of the object of the present invention. .
Moreover, in this specification, "-" represents above from the following, unless there is particular notice.

«Curable composition»
The curable composition according to the first aspect is a cationic curable or anionic curable curable composition, wherein the curable composition contains (C) an ionic liquid having a melting point of 140 ° C. or less, and has a wavelength A cured film having a refractive index of 1.60 or more and 2.20 or less for light of 550 nm is provided.

The curable composition according to the second aspect is a cationic curable or anionic curable curable composition, which is a functional composition containing at least one element selected from the group consisting of N, O, S and Si. A curable composition containing (A) a curable compound having a group and (C) an ionic liquid having a melting point of 140 ° C. or less, wherein the (A) curable compound has an aromatic group, a triazine ring structure, It contains at least one selected from the group consisting of an isocyanuric ring structure and a cyclic siloxane structure.
The curable composition according to the second aspect preferably provides a cured film having a refractive index of 1.60 or more and 2.20 or less for light having a wavelength of 550 nm.
Hereinafter, the curable composition according to the first aspect and the curable composition according to the second aspect are collectively referred to simply as "curable composition".
The curable composition preferably gives a cured film having a refractive index of 1.65 or more and 2.10 or less with respect to a light beam having a wavelength of 550 nm, from the viewpoint of high refractive index, and curing is 1.70 or more and 2.00 or less More preferably, a membrane is provided.
In the present invention, the refractive index is based on the conditions measured in the following examples unless otherwise specified.

By including the (C) ionic liquid in the curable composition, the curing reaction can be uniformly promoted in the curable composition with low dependence on whether it is cationic polymerization or anionic polymerization, and as a result, the result is obtained. It is possible to form a cured product which is excellent in refractive index and resistance to yellowing (in particular, resistance to yellowing), and also good in heat resistance and adhesion to a substrate.
Hereinafter, essential or optional components contained in the curable composition will be described.

<(A) curable compound>
The curable composition according to the first aspect is at least selected from the group consisting of N, O, S and Si from the viewpoints of refractive index and resistance to yellowing and from the viewpoint of heat resistance and adhesion to a substrate. It is preferable to further include (A) a curable compound having a functional group containing one kind of element.

The curable compound (A) having a functional group containing at least one element selected from the group consisting of N, O, S and Si tends to have a relatively high refractive index.
From the viewpoint of high refractive index, the curable compound (A) preferably has a functional group containing at least one element selected from the group consisting of N, S and O, and is selected from the group consisting of N and S It is more preferable to have a functional group containing at least one element selected.

  Examples of the functional group containing N include a triazine ring structure, an isocyanuric ring structure, a carbazole group, an imide group and a nitrile group. As a (A) curable compound which has a functional group containing N, the polymer which has a triazine ring, the compound represented by the below-mentioned Formula (a1-I), polyvinylcarbazole (PVK), a polyimide etc. are mentioned. A polymer having a triazine ring is particularly preferable because of its relatively high refractive index (1.70 or more).

As a functional group containing O, an epoxy group, an isocyanuric ring structure, a carboxyl group, an ester group, a ketone group, a hydroxyl group etc. are mentioned.
Examples of the (A) curable compound having a functional group containing O include a compound represented by Formula (a1) described later, a compound represented by Formula (a1-I) described later, an epoxy compound described later, etc. .

The functional group containing S, thiirane group, a sulfonyl group (-SO 2 _-), a thiol group, such as a thioester group.
Examples of the (A) curable compound having a functional group containing S include a compound represented by the following formula (a1), polyethersulfone (PES), polysulfone, polyphenylsulfone and the like.
As a (A) curable compound which has a functional group containing Si, the siloxane compound etc. which have a siloxane skeleton comprised by the siloxane bond (Si-O-Si) are mentioned. Examples of the siloxane skeleton in the siloxane compound include a cyclic siloxane skeleton and a cage-type or ladder-type polysilsesquioxane skeleton.

The curable compound (A) is selected from the group consisting of an aromatic group, a triazine ring structure, an isocyanuric ring structure and a cyclic siloxane structure from the viewpoints of refractive index and yellowing resistance, and heat resistance and adhesion to a substrate. It is preferable to include at least one selected.
The curable composition according to the second aspect has a functional group containing at least one element selected from the group consisting of N, O, S and Si, and an aromatic group, a triazine ring structure, an isocyanuric ring structure And (A) a curable compound containing at least one selected from the group consisting of and cyclic siloxane structures.
The aromatic group is preferably an aromatic group forming a cardo structure from the viewpoints of refractive index and yellowing resistance, and heat resistance and adhesion to a substrate.

  (A) A curable compound is a compound represented by the following formula (a1), a polymer having a triazine ring structure, from the viewpoints of refractive index and yellowing resistance, and heat resistance and adhesion to a substrate, It is preferable to include at least one selected from the group consisting of a compound represented by the following formula (a1-I) and a siloxane epoxy compound represented by the following formula (a1-III).

（式（ａ１）中、Ｗ^１及びＷ^２は、それぞれ独立に、下記式（ａ２）：

で表される基であり、
式（ａ２）中、環Ｚは芳香族炭化水素環を示し、Ｘは単結合又は−Ｓ−で示される基を示し、Ｒ^０１は単結合、炭素原子数が１以上４以下であるアルキレン基、又は炭素原子数が１以上４以下であるアルキレンオキシ基を示し、Ｒ^０１がアルキレンオキシ基である場合、アルキレンオキシ基中の酸素原子が環Ｚと結合し、Ｒ^０２は１価炭化水素基、水酸基、−ＯＲ^４ａで示される基、−ＳＲ^４ｂで示される基、アシル基、アルコキシカルボニル基、ハロゲン原子、ニトロ基、シアノ基、メルカプト基、カルボキシ基、アミノ基、カルバモイル基、−ＮＨＲ^４ｃで示される基、−Ｎ（Ｒ^４ｄ）_２で示される基、スルホ基、又は１価炭化水素基、−ＯＲ^４ａで示される基、−ＳＲ^４ｂで示される基、アシル基、アルコキシカルボニル基、−ＮＨＲ^４ｃで示される基、もしくは−Ｎ（Ｒ^４ｄ）_２で示される基に含まれる炭素原子に結合した水素原子の少なくとも一部が１価炭化水素基、水酸基、−ＯＲ^４ａで示される基、−ＳＲ^４ｂで示される基、アシル基、アルコキシカルボニル基、ハロゲン原子、ニトロ基、シアノ基、メルカプト基、カルボキシ基、アミノ基、カルバモイル基、−ＮＨＲ^４ｃで示される基、−Ｎ（Ｒ^４ｄ）_２で示される基、メシルオキシ基、もしくはスルホ基で置換された基を示し、Ｒ^４ａ〜Ｒ^４ｄは独立に１価炭化水素基を示し、ｍは０以上の整数を示し、Ｒ^０３は、水素原子、ビニル基、チイラン−２−イルメチル基、又はグリシジル基であり、
Ｗ^１とＷ^２との双方がＲ^０３として水素原子を有することはなく、
環Ｙ^１及び環Ｙ^２は同一の又は異なる芳香族炭化水素環を示し、Ｒは単結合、置換基を有してもよいメチレン基、置換基を有してもよく、２個の炭素原子間にヘテロ原子を含んでもよいエチレン基、−Ｏ−で示される基、−ＮＨ−で示される基、又は−Ｓ−で示される基を示し、Ｒ^３ａ及びＲ^３ｂは独立にシアノ基、ハロゲン原子、又は１価炭化水素基を示し、ｎ１及びｎ２は独立に０以上４以下の整数を示す。） (Compound represented by formula (a1))

(In formula (a1), W ¹ and W ² are each independently represented by the following formula (a2):

Is a group represented by
In formula (a2), ring Z represents an aromatic hydrocarbon ring, X represents a single bond or a group represented by -S-, R ⁰¹ represents a single bond, and an alkylene group having 1 to 4 carbon atoms. Or an alkyleneoxy group having 1 or more and 4 or less carbon atoms, and when R ⁰¹ is an alkyleneoxy group, an oxygen atom in the alkyleneoxy group is bonded to ring Z, and R ⁰² is a monovalent hydrocarbon group , A hydroxyl group, a group represented by -OR ^4a , a group represented by -SR ^4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, -NHR ^4c a group represented by group represented by ^{-N (R} _{4d) 2,} sulfo group, or a monovalent hydrocarbon group, a group represented by ^{-OR 4a,} a group represented by ^{-SR 4b,} an acyl group, an alkoxycarbonyl group, At least a portion monovalent hydrocarbon group, a hydroxyl group, a group represented by ^{-OR 4a} of the hydrogen atoms bonded to carbon atoms contained in the group represented a group represented by NHR ^4c or by ^{-N (R} _{4d) 2,,} A group represented by -SR ^4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, a group represented by -NHR ^4c , -N (R ^4d ) a group represented by _2, shows a substituted group mesyloxy group or a sulfo group,, R ^4a to R ^4d represents a monovalent hydrocarbon radical independently, m represents an integer of 0 or more, R ⁰³ is hydrogen An atom, a vinyl group, a thiiran-2-ylmethyl group, or a glycidyl group,
Both W ¹ and W ² have no hydrogen atom as R ⁰³ ,
Ring Y ¹ and ring Y ² are the same or different aromatic hydrocarbon rings, R is a single bond, a methylene group which may have a substituent, may have a substituent, and 2 carbon atoms Represents an ethylene group which may contain a hetero atom, a group represented by -O-, a group represented by -NH- or a group represented by -S-, and R ^3a and R ^3b independently represent a cyano group or halogen An atom or a monovalent hydrocarbon group is shown, and n1 and n2 independently represent an integer of 0 or more and 4 or less. )

In the above formula (a2), as the ring Z, for example, a benzene ring, a fused polycyclic aromatic hydrocarbon ring [for example, a fused bicyclic hydrocarbon ring (for example, a C _8-20 fused bicyclic such as a naphthalene ring, etc. Fused hydrocarbon rings such as C _10-16 fused bicyclic hydrocarbon rings), fused tricyclic aromatic hydrocarbon rings (eg, anthracene ring, phenanthrene ring, etc.), etc. Hydrogen ring] and the like. The ring Z is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring. In addition, since W ¹ and W ² in the formula (a1) are each independently a group represented by the following formula (a2), W ¹ and W ² each include the ring Z. The ring Z contained in W ¹ and the ring Z contained in W ² may be the same or different, and for example, one ring may be a benzene ring and the other ring may be a naphthalene ring etc. It is particularly preferable that the ring of is also a naphthalene ring.

In addition, the substitution position of ring Z bonded via X to a carbon atom to which both W ¹ and W ² are directly bonded is not particularly limited. For example, when the ring Z is a naphthalene ring, the group corresponding to the ring Z bonded to the carbon atom may be a 1-naphthyl group, a 2-naphthyl group or the like.

  In the above formula (a2), X independently represents a single bond or a group represented by -S-, and is typically a single bond.

In the above formula (a2), R ⁰¹ is, for example, a single bond; alkylene having 1 to 4 carbon atoms, such as methylene, ethylene, trimethylene, propylene and butane-1,2-diyl. Groups include alkyleneoxy groups having 1 to 4 carbon atoms, such as methyleneoxy, ethyleneoxy and propyleneoxy groups; single bonds; _C.sub.2-4 alkylene (especially ethylene, propylene and the like) _C2-3 alkylene group); _C2-4 alkyleneoxy group (in particular, _C2-3 alkylene group such as ethyleneoxy group and propyleneoxy group) is preferable, and a single bond is more preferable. When R ⁰¹ is an alkyleneoxy group, an oxygen atom in the alkyleneoxy group bonds to ring Z. Further, since W ¹ and W ² in the formula (a1) are each independently a group represented by the following formula (a2), W ¹ and W ² are each a divalent group R ⁰¹ Including. The ^{R 01} contained in ^{R 01} and ^{W 2} included in W ^1, it may be the same or may be different.

In the above formula (a2), R ⁰² is, for example, an alkyl group (for example, a C _1-12 alkyl group such as methyl group, ethyl group, propyl group, isopropyl group or butyl group, preferably a C _1-8 alkyl group) , More preferably a C _1-6 alkyl group etc., a cycloalkyl group (C _5-10 cycloalkyl group such as cyclohexyl group, preferably a C _5-8 cycloalkyl group, more preferably a C _5-6 cycloalkyl group etc. ), Aryl groups (eg, C _6-14 aryl groups such as phenyl, tolyl, xylyl and naphthyl groups, preferably C _6-10 aryl groups, more preferably C _6-8 aryl groups, etc.), aralkyl groups hydroxyl; monovalent hydrocarbon group, (benzyl, _{C 6-10} aryl _{-C 1-4} alkyl group such as a phenethyl group) alkoxy group (methoxy , An ethoxy group, a propoxy group, _{C 1-12} alkoxy group or a butoxy group, preferably a _{C 1-8} alkoxy group, more preferably _{C 1-6} alkoxy group, etc.), _{C 5} such cycloalkoxy groups (cyclohexyloxy _-10 cycloalkoxy group etc., aryloxy group (C _6-10 aryloxy group such as phenoxy group), aralkyloxy group (eg C _6-10 aryl-C _1-4 alkyloxy group such as benzyloxy group) And the like, a group represented by -OR ^4a , wherein R ^4a is a monovalent hydrocarbon group (such as the monovalent hydrocarbon group exemplified above). Alkylthio group (C _1-12 alkylthio group such as methylthio group, ethylthio group, propylthio group, butylthio group, etc., preferably C _1-8 alkylthio group, more preferably C _1-6 alkylthio group etc.), cycloalkylthio group ( C _5-10 cycloalkylthio group such as cyclohexylthio group), arylthio group (C _6-10 arylthio group such as phenylthio group), aralkylthio group (eg, C _6-10 aryl-C _1-4 such as benzylthio group) A group represented by -SR ^4b , such as an alkylthio group) [wherein, R ^4b represents a monovalent hydrocarbon group (a monovalent hydrocarbon group as exemplified above, etc.)]. Acyl group (C _1-6 acyl group such as acetyl group etc.); alkoxycarbonyl group (C _1-4 alkoxy-carbonyl group such as methoxycarbonyl group etc.); halogen atom (fluorine atom, chlorine atom, bromine atom, Iodine atom etc .; nitro group; cyano group; mercapto group; carboxy group; amino group; carbamoyl group; alkylamino group (methylamino group, ethylamino group, propylamino group, _C1-12 alkylamino group such as butylamino group) Group, preferably a C _1-8 alkylamino group, more preferably a C _1-6 alkylamino group, etc., a cycloalkylamino group (C _5-10 cycloalkylamino group such as a cyclohexylamino group, etc.), an arylamino group (C _6-10 arylamino group such as phenylamino group), aralkylamino group (eg, benzylamine) A group represented by —NHR ^4c such as C _6-10 aryl-C _1-4 alkylamino group such as a group [wherein R ^4c is a monovalent hydrocarbon group (monovalent hydrocarbon group as exemplified above, etc.)] Indicates A dialkylamino group (a di (C _1-12 alkyl) amino group such as dimethylamino, diethylamino, dipropylamino, dibutylamino etc., preferably a di (C _1-8 alkyl) amino group, more preferably Di (C _1-6 alkyl) amino group etc., dicycloalkylamino group (di (C _5-10 cycloalkyl) amino group such as dicyclohexylamino group etc.), diarylamino group (diphenylamino group etc. _6-10 aryl) amino group), diaralkylamino group (for example, di (C _6-10 aryl-C _1-4 alkyl) amino group such as dibenzylamino group), and the like, represented by -N (R ^4d ) ₂ Wherein R ^{4 d} independently represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon group exemplified above). A (meth) acryloyloxy group; a sulfo group; a group represented by the above monovalent hydrocarbon group, a group represented by -OR ^4a , a group represented by -SR ^4b , an acyl group, an alkoxycarbonyl group, a group represented by -NHR ^4c Or at least a part of the hydrogen atoms bonded to the carbon atom contained in the group represented by -N (R ^4d ) ₂ is the above-mentioned monovalent hydrocarbon group, a hydroxyl group, a group represented by -OR ^4a , -SR ^4b Group represented by the following group, acyl group, alkoxycarbonyl group, halogen atom, nitro group, cyano group, mercapto group, carboxy group, amino group, carbamoyl group, group represented by -NHR ^4c , or -N (R ^4d ) ₂ Group, a group substituted with a (meth) acryloyloxy group, a mesyloxy group, or a sulfo group [eg, an alkoxyaryl group (eg, a methoxyphenyl group, etc. _1-4 alkoxy _{C 6-10} aryl group), an alkoxycarbonyl aryl group (e.g., methoxycarbonyl phenyl group, _{C 1-4} alkoxy such as ethoxy carbonyl phenyl - carbonyl _{C 6-10} aryl group)], and the like .

Among these, representatively, R ⁰² is a monovalent hydrocarbon group, a group represented by -OR ^4a , a group represented by -SR ^4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group And a group represented by -NHR ^4c , a group represented by -N (R ^4d ) ₂ or the like.

Preferable R ⁰² is a monovalent hydrocarbon group [eg, an alkyl group (eg, a C _1-6 alkyl group), a cycloalkyl group (eg, a C _5-8 cycloalkyl group), an aryl group (eg, C _{6− 10} aryl group), an aralkyl group (for example, C _6-8 aryl-C _1-2 alkyl group etc.), an alkoxy group (C _1-4 alkoxy group etc.) and the like. Particularly, R ⁰² is a monovalent hydrocarbon group such as an alkyl group [C _1-4 alkyl group (especially methyl group) etc.], an aryl group [eg C _6-10 aryl group (especially phenyl group) etc.] (especially And alkyl groups are preferred.

In addition, when m is an integer greater than or equal to 2, several R ⁰² may mutually differ and may be the same. Moreover, the ^{R 02} contained in ^{R 02} and ^{W 2} included in ^{W 1,} may be the same or may be different.

In the above formula (a2), the number m of R ⁰² can be selected according to the type of ring Z, and may be, for example, 0 or more and 4 or less, preferably 0 or more and 3 or less, more preferably 0 or more and 2 or less . Note that m in W ¹ and m in W ² may be the same or different.

In the above formula (a3), R ⁰³ is a hydrogen atom, a vinyl group, a thiiran-2-ylmethyl group, or a glycidyl group. Note that neither W ¹ nor W ² has a hydrogen atom as R ⁰³ .
The vinyloxy group, thiiran-2-ylmethyl group, and glycidyl group are all cationically polymerizable functional groups. Accordingly, the compound represented by the formula (a1) is a cationically polymerizable compound having one or two cationically polymerizable functional groups.
The R ⁰³ contained in R ⁰³ and W ² included in W ^1, as long as both are not hydrogen atoms, may be the same or may be different. The ^{R 03} contained in ^{R 03} and ^{W 2} included in W ^1, both a vinyl group, thiirane-2-ylmethyl group, or is preferably Ku glycidyl group, both a vinyl group, thiirane -2 It is more preferable that it is the same group selected from the group consisting of -ylmethyl group and glycidyl group.
As R ⁰³ , a vinyl group or a glycidyl group is preferable because synthesis and availability of a compound represented by formula (a1) are easy.

In the above formula (a1), as the ring Y ¹ and the ring Y ² , for example, a benzene ring, a fused polycyclic aromatic hydrocarbon ring [for example, a fused bicyclic hydrocarbon ring (for example, C ₈ such as a naphthalene ring, etc. _-20 fused bicyclic hydrocarbon ring, preferably C _10-16 fused bicyclic hydrocarbon ring), fused tricyclic aromatic hydrocarbon ring (eg, anthracene ring, phenanthrene ring, etc.), etc. Cyclic aromatic hydrocarbon ring] and the like. The ring Y ¹ and the ring Y ² are preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring. The ring Y ¹ and the ring Y ² may be the same or different, and for example, one ring may be a benzene ring, and the other ring may be a naphthalene ring or the like.

In the above formula (a1), R represents a single bond, a methylene group which may have a substituent, an ethylene group which may have a substituent, and may contain a hetero atom between two carbon atoms, A group represented by-, a group represented by -NH-, or a group represented by -S- is represented, and typically it is a single bond. Here, examples of the substituent include a cyano group, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, etc.), a monovalent hydrocarbon group [eg, an alkyl group (a methyl group, an ethyl group, a propyl group, an isopropyl group, And C _1-6 alkyl groups such as butyl and t-butyl), aryl groups (C _6-10 aryl groups such as phenyl and the like), etc., and the like, and examples of the hetero atom include an oxygen atom and a nitrogen atom And sulfur atoms, silicon atoms and the like.

In the above formula (a1), as R ^3a and R ^3b , usually, non-reactive substituents such as cyano group, halogen atom (fluorine atom, chlorine atom, bromine atom etc.), monovalent hydrocarbon group [eg, Examples thereof include an alkyl group and an aryl group (a C _6-10 aryl group such as a phenyl group etc.) and the like. Examples of the alkyl group include C _1-6 alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group and t-butyl group (for example, C _1-4 alkyl group, particularly methyl group) and the like . When n1 is an integer of 2 or more, R ^3a may be different from each other or may be the same. In addition, when n2 is an integer of 2 or more, R ^3b may be different from each other or may be the same. Furthermore, R ^3a and R ^3b may be the same or different. Further, the bonding position (substituting position) of R ^3a and R ^{3b to} the ring Y ¹ and the ring Y ² is not particularly limited. Preferred substitution numbers n1 and n2 are 0 or 1, in particular 0. Note that n1 and n2 may be the same as or different from each other.

The compound represented by the above formula (a1) has high reactivity because it has a cationically polymerizable functional group while maintaining excellent optical properties and thermal properties. In particular, when the ring Y ¹ and the ring Y ² are benzene rings and R is a single bond, the compound represented by the above formula (a1) has a fluorene skeleton, and the optical properties and thermal properties are further increased. Excellent.
Furthermore, the compound represented by the said Formula (a1) gives the hardened | cured material which has high hardness, and is preferable as a base-material component in a composition.

  Among the compounds represented by the above formula (a1), particularly preferable examples include 9,9-bis [4- [2- (glycidyloxy) ethoxy] phenyl] -9H-fluorene, 9,9-bis [ 4- [2- (glycidyloxy) ethyl] phenyl] -9H-fluorene, 9,9-bis [4- (glycidyloxy) -3-methylphenyl] -9H-fluorene, 9,9-bis [4- ( Glycidyloxy) -3,5-dimethylphenyl] -9H-fluorene, 9,9-bis (6-glycidyloxynaphthalen-1-yl) -9H-fluorene and 9,9-bis (5-glycidyloxynaphthalene-2 And epoxy group-containing fluorene compounds such as -yl) -9H-fluorene; and compounds represented by the following formula.

Among the compounds represented by the formula (a1) described above, the following compounds are particularly preferable.

  When the curable compound (A) contains a compound represented by the above formula (a1), the amount of the compound represented by the above formula (a1) in the curable compound (A) is preferably 50% by mass or more. 70 mass% or more is more preferable, 80 mass% or more is further more preferable, 90 mass% or more is especially preferable, and 100 mass% is the most preferable.

(Epoxy compound)
Examples of the above-mentioned epoxy compounds include bifunctional epoxy resins such as bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, bisphenol AD epoxy resin, naphthalene epoxy resin, and biphenyl epoxy resin; Novolac epoxy resin such as phenol novolac epoxy resin, brominated phenol novolac epoxy resin, ortho cresol novolac epoxy resin, bisphenol A novolac epoxy resin, and bisphenol AD novolac epoxy resin; Epoxide of dicyclopentadiene type phenol resin And cycloaliphatic epoxy resins; aromatic epoxy resins such as epoxidized naphthalene type phenolic resins; dimeric glycidyl esters; Glycidyl ester type epoxy resins such as ester esters; glycidyl amine type epoxy resins such as tetraglycidyl aminodiphenylmethane, triglycidyl-p-aminophenol, tetraglycidyl metaxylylenediamine, and tetraglycidyl bisaminomethyl cyclohexane; such as triglycidyl isocyanurate Heterocyclic epoxy resin; phlorogricinol triglycidyl ether, trihydroxybiphenyl triglycidyl ether, trihydroxyphenylmethane triglycidyl ether, glycerin triglycidyl ether, 2- [4- (2,3-epoxypropoxy) phenyl] -2 -[4- [1,1-bis [4- (2,3-epoxypropoxy) phenyl] ethyl] phenyl] propane, and 1,3-bis [4- [1- [1 -(2,3-Epoxypropoxy) phenyl] -1- [4- [1- [4- (2,3-epoxypropoxy) phenyl] -1-methylethyl] phenyl] ethyl] phenoxy] -2-propanol and the like Trifunctional epoxy resins; tetrahydroxyphenylethane tetraglycidyl ether, tetraglycidyl benzophenone, bisresorcinol tetraglycidyl ether, and tetrafunctional epoxy resins such as tetraglycidoxybiphenyl; 2, 2-bis (hydroxymethyl) -1 -1, 2-epoxy-4- (2-oxiranyl) cyclohexane adduct of butanol is mentioned. A 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol is commercially available as EHPE-3150 (manufactured by Daicel).

Further, oligomeric or polymeric polyfunctional epoxy compounds can also be preferably used as the (A) curable compound.
Typical examples include phenol novolac epoxy compounds, brominated phenol novolac epoxy compounds, ortho cresol novolac epoxy compounds, xylenol novolac epoxy compounds, naphthol novolac epoxy compounds, bisphenol A novolac epoxy compounds, bisphenol AD novolac Type epoxy compound, an epoxy compound of dicyclopentadiene type phenol resin, an epoxy compound of naphthalene type phenol resin, and the like.

  Other examples of suitable epoxy compounds include polyfunctional alicyclic epoxy compounds having an alicyclic epoxy group. (A) When a curable compound contains an alicyclic epoxy compound, it is easy to form the hardened | cured material which is excellent in transparency using a curable composition.

Specific examples of such alicyclic epoxy compounds include 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-meta-dioxane, bis (3,4-epoxycyclohexylmethyl) Adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexyl-3 ', 4'-epoxy-6'-methylcyclohexanecarboxylate, ε-caprolactone modified 3 , 4-Epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate, trimethylcaprolactone modified 3,4-epoxycyclohexylmethyl-3', 4'-epoxycyclohexanecarboxylate, β-methyl-δ-valerolactone modified 3 , 4-Epoxycyclohexyl Methyl-3 ', 4'-epoxycyclohexanecarboxylate, methylenebis (3,4-epoxycyclohexane), di (3,4-epoxycyclohexylmethyl) ether of ethylene glycol, ethylenebis (3,4-epoxycyclohexanecarboxylate) And polyfunctional epoxy compounds having a tricyclodecene oxide group, and compounds represented by the following formulas (a1-1) to (a1-5).
These alicyclic epoxy compounds may be used alone or in combination of two or more.

（式（ａ１−１）中、Ｚは単結合又は連結基（１以上の原子を有する二価の基）を示す。Ｒ^ａ１〜Ｒ^ａ１８は、それぞれ独立に、水素原子、ハロゲン原子、及び有機基からなる群より選択される基である。）

(In Formula (a1-1), Z represents a single bond or a linking group (a divalent group having one or more atoms). R ^{a1 to} R ^a18 each independently represent a hydrogen atom, a halogen atom, or an organic group A group selected from the group consisting of groups)

As the linking group Z, for example, a divalent hydrocarbon group, —O—, —O—CO—, —S—, —SO—, —SO ₂ —, —CBr ₂ —, —C (CBr ₃ ) _{2 -, - C (CF 3)} 2 -, and ^-R a19 -O-CO- 2 divalent group and which are selected from the group consisting of these can be exemplified a plurality bonded group.

  Examples of the divalent hydrocarbon group which is a linking group Z include a linear or branched alkylene group having 1 to 18 carbon atoms and a divalent alicyclic hydrocarbon group. Can. Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, a dimethylene group and a trimethylene group. Examples of the divalent alicyclic hydrocarbon group include a 1,2-cyclopentylene group, a 1,3-cyclopentylene group, a cyclopentylidene group, a 1,2-cyclohexylene group, and a 1,3-disubstituted cycloaliphatic hydrocarbon group. Cycloalkylene groups (including cycloalkylidene groups) such as cyclohexylene group, 1,4-cyclohexylene group, cyclohexylidene group and the like can be mentioned.

R ^a19 is an alkylene group having 1 to 8 carbon atoms, and is preferably a methylene group or an ethylene group.

(In formula (a1-2), R ^{a1 to} R ^a12 are a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group.)

（式（ａ１−３）中、Ｒ^ａ１〜Ｒ^ａ１０は、水素原子、ハロゲン原子、及び有機基からなる群より選択される基である。Ｒ^ａ２及びＲ^ａ８は、互いに結合してもよい。）

(In formula (a1-3), R ^{a1 to} R ^a10 are a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group. R ^a2 and R ^a8 may be bonded to each other. )

（式（ａ１−４）中、Ｒ^ａ１〜Ｒ^ａ１２は、水素原子、ハロゲン原子、及び有機基からなる群より選択される基である。Ｒ^ａ２及びＲ^ａ１０は、互いに結合してもよい。）

(In formula (a1-4), R ^{a1 to} R ^a12 are a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group. R ^a2 and R ^a10 may be bonded to each other. )

（式（ａ１−５）中、Ｒ^ａ１〜Ｒ^ａ１２は、水素原子、ハロゲン原子、及び有機基からなる群より選択される基である。）

(In formula (a1-5), R ^{a1 to} R ^a12 are a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group.)

Wherein (a1-1) ~ ^(a1-5), when R ^{a1 to R a18} is an organic group, the organic group is not particularly limited within a range not inhibiting the object of the present invention, it is a hydrocarbon radical Or a group consisting of a carbon atom and a halogen atom, or may be a group containing a halogen atom, an oxygen atom, a sulfur atom, a nitrogen atom, a hetero atom such as a silicon atom, as well as a carbon atom and a hydrogen atom . Examples of the halogen atom include chlorine atom, bromine atom, iodine atom, and fluorine atom.

  As an organic group, a group consisting of a hydrocarbon group, a carbon atom, a hydrogen atom and an oxygen atom, a halogenated hydrocarbon group, a group consisting of a carbon atom, an oxygen atom and a halogen atom, a carbon atom and a hydrogen atom And the group which consists of an oxygen atom and a halogen atom is preferable. When the organic group is a hydrocarbon group, the hydrocarbon group may be an aromatic hydrocarbon group, an aliphatic hydrocarbon group, or a group containing an aromatic skeleton and an aliphatic skeleton. The number of carbon atoms in the organic group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 5 or less.

  Specific examples of the hydrocarbon group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group and n-hexyl group , N-heptyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group And linear alkyl groups such as n-heptadecyl, n-octadecyl, n-nonadecyl and n-icosyl; vinyl, 1-propenyl, 2-n-propenyl (allyl), 1-n -Chain-like alkenyl groups such as butenyl group, 2-n-butenyl group and 3-n-butenyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group And cycloalkyl groups such as cycloheptyl group; phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, α-naphthyl group, β-naphthyl group, β-naphthyl group, biphenyl-4-yl group, biphenyl-3-yl group Aryl group such as biphenyl-2-yl group, anthryl group and phenanthryl group; benzyl group, phenethyl group, α-naphthylmethyl group, β-naphthylmethyl group, α-naphthylethyl group and β-naphthylethyl group And aralkyl groups such as

  Specific examples of the halogenated hydrocarbon group are chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, tribromomethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2, 2 , 2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluorooctyl group, perfluorononyl group, and Halogenated linear alkyl group such as perfluorodecyl group; 2-chlorocyclohexyl group, 3-chlorocyclohexyl group, 4-chlorocyclohexyl group, 2,4-dichlorocyclohexyl group, 2-bromocyclohexyl group, 3-bromocyclohexyl group , And 4- Halogenated cycloalkyl group such as mocyclohexyl group; 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2, 6 -Dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4- Halogenated aryl groups such as fluorophenyl group; 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2-bromophenylmethyl group, 3-bromophenylmethyl group, 4-bromophenylmethyl group, 2 -Fluorophenylmethyl group, 3-fluorophenyl Methyl group, a halogenated aralkyl group such as 4-fluorophenyl methyl group.

  Specific examples of the group consisting of carbon atom, hydrogen atom and oxygen atom are hydroxy chain such as hydroxymethyl group, 2-hydroxyethyl group, 3-hydroxy-n-propyl group and 4-hydroxy-n-butyl group Alkyl group; halogenated cycloalkyl group such as 2-hydroxycyclohexyl group, 3-hydroxycyclohexyl group, and 4-hydroxycyclohexyl group; 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 2, 3 -Hydroxyaryl groups such as dihydroxyphenyl group, 2,4-dihydroxyphenyl group, 2,5-dihydroxyphenyl group, 2,6-dihydroxyphenyl group, 3,4-dihydroxyphenyl group, and 3,5-dihydroxyphenyl group 2-hydroxyphenylmethyl group, 3-hydroxy Hydroxyaralkyl groups such as phenylmethyl group and 4-hydroxyphenylmethyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n-trioxy group Decyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-nonadecyloxy, n-icosyloxy, etc. Linear alkoxy group; vinyloxy group, 1-propenyl group A chain alkenyloxy group such as a cis group, 2-n-propenyloxy group (allyloxy group), 1-n-butenyloxy group, 2-n-butenyloxy group, and 3-n-butenyloxy group; phenoxy group, o-tolyloxy Group, m-tolyloxy group, p-tolyloxy group, α-naphthyloxy group, β-naphthyloxy group, biphenyl-4-yloxy group, biphenyl-3-yloxy group, biphenyl-2-yloxy group, anthryloxy group, And aryloxy groups such as phenanthryloxy groups; benzyloxy groups, phenethyloxy groups, α-naphthylmethyloxy groups, β-naphthylmethyloxy groups, α-naphthylethyloxy groups, β-naphthylethyloxy groups and the like Aralkyloxy group; methoxymethyl group, ethoxymethyl group, n-propoxymethyl group , 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 3-methoxy-n-propyl group, 3-ethoxy-n-propyl group, 3-n-propoxy-n-propyl group, Alkoxyalkyl groups such as 4-methoxy-n-butyl group, 4-ethoxy-n-butyl group, and 4-n-propoxy-n-butyl group; methoxymethoxy group, ethoxymethoxy group, n-propoxymethoxy group, 2 4-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propoxyethoxy group, 3-methoxy-n-propoxy group, 3-ethoxy-n-propoxy group, 3-n-propoxy-n-propoxy group, 4- Alkoxy alkoxy such as methoxy-n-butyloxy group, 4-ethoxy-n-butyloxy group, and 4-n-propoxy-n-butyloxy group Groups; alkoxyaryl groups such as 2-methoxyphenyl group, 3-methoxyphenyl group, and 4-methoxyphenyl group; alkoxyaryloxy groups such as 2-methoxyphenoxy group, 3-methoxyphenoxy group, and 4-methoxyphenoxy group Aliphatic acyl groups such as formyl group, acetyl group, propionyl group, butanoyl group, pentanoyl group, hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, and decanoyl group; benzoyl group, α-naphthoyl group, and β-naphthoyl Aromatic acyl groups such as groups; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, n-butyloxycarbonyl group, n-pentyloxycarbonyl group, n-hexylcarbonyl group, n-heptyloxycarbonyl group, n -Octyloxy Chain-like alkyloxycarbonyl groups such as rubonyl group, n-nonyloxycarbonyl group and n-decyloxycarbonyl group; and aryloxycarbonyl groups such as phenoxycarbonyl group, α-naphthoxy carbonyl group and β-naphthoxy carbonyl group Aliphatics such as formyloxy group, acetyloxy group, propionyloxy group, butanoyloxy group, pentanoyloxy group, hexanoyloxy group, heptanoyloxy group, octanoyloxy group, nonanoyloxy group, and decanoyloxy group Acyloxy groups; aromatic acyloxy groups such as benzoyloxy group, α-naphthoyloxy group, and β-naphthoyloxy group.

Each of R ^{a1 to} R ^a18 is independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms. It is more preferable that all of R ^{a1 to} R ^a18 be a hydrogen atom because a group is preferable, and in particular, a cured film having excellent mechanical properties can be easily formed.

Wherein ^{(a1-2) ~ (a1-5),} R a1 ~R a12 is the same as ^R a1 ^{to R a12} in equation (a1-1). Examples of the divalent group formed when R ^a2 and R ^a10 are bonded to each other in formula (a1-2) and formula (a1-4) include, for example, -CH ₂ -and -C (CH ₃ ) _2- . In Formula (a1-3), examples of the divalent group formed when R ^a2 and R ^a8 bond to each other include -CH ₂ -and -C (CH ₃ ) _2- .

Among the alicyclic epoxy compounds represented by the formula (a1-1), specific examples of a suitable compound include the following formula (a1-1a), the following formula (a1-1b), and the following formula (a1-1c) And cycloaliphatic epoxy compounds represented by 2), 2,2-bis (3,4-epoxycyclohexan-1-yl) propane [= 2,2-bis (3,4-epoxycyclohexyl) propane], etc. be able to.

Among the alicyclic epoxy compounds represented by the formula (a1-2), specific examples of preferable compounds include bicyclononadiene diepoxide represented by the following formula (a1-2a) or dicyclononadiene diepoxide Etc.

Among the alicyclic epoxy compounds represented by the formula (a1-3), specific examples of preferable compounds include Sspiro [3-oxatricyclo [3.2.1.0 ^2,4 ] octane-6. , 2′-oxirane] and the like.

  Among the alicyclic epoxy compounds represented by the formula (a1-4), specific examples of suitable compounds include 4-vinylcyclohexene dioxide, dipentene dioxide, limonene dioxide, 1-methyl-4- (3) And -methyl oxirane-2-yl) -7-oxabicyclo [4.1.0] heptane and the like.

  Among the alicyclic epoxy compounds represented by the formula (a1-5), specific examples of preferable compounds include 1,2,5,6-diepoxycyclooctane and the like.

（式（ａ１−Ｉ）中、Ｘ^ａ１、Ｘ^ａ２、及びＸ^ａ３は、それぞれ独立に、水素原子、又はエポキシ基を含んでいてもよい有機基であり、Ｘ^ａ１、Ｘ^ａ２、及びＸ^ａ３が有するエポキシ基の総数が２以上である。） (Compound represented by formula (a1-I))

(In the formula (a1-I), X ^a1 , X ^a2 and X ^a3 each independently represent a hydrogen atom or an organic group which may contain an epoxy group, and X ^a1 , X ^a2 and X ^a3 The total number of epoxy groups possessed is 2 or more.)

（式（ａ１−ＩＩ）中、Ｒ^ａ２０〜Ｒ^ａ２２は、直鎖状、分岐鎖状又は環状のアルキレン基、アリーレン基、−Ｏ−、−Ｃ（＝Ｏ）−、−ＮＨ−及びこれらの組み合わせからなる基であり、それぞれ同一であってもよいし、異なっていてもよい。Ｅ^１〜Ｅ^３は、エポキシ基、オキセタニル基、エチレン性不飽和基、アルコキシシリル基、イソシアネート基、ブロックイソシアネート基、チオール基、カルボキシ基、水酸基及びコハク酸無水物基からなる群より選択される少なくとも１種の置換基又は水素原子である。ただし、Ｅ^１〜Ｅ^３のうち少なくとも２つは、エポキシ基及びオキセタニル基からなる群より選択される少なくとも１種である。） As a compound represented by the said Formula (a1-I), the compound represented by a following formula (a1-II) is preferable.

(In formula (a1-II), R ^{a20 to} R ^{a22 each} represents a linear, branched or cyclic alkylene group, an arylene group, -O-, -C (= O)-, -NH-, and the like, E ^{1 to} E ³ may each be an epoxy group, an oxetanyl group, an ethylenically unsaturated group, an alkoxysilyl group, an isocyanate group, or a blocked isocyanate. At least one type of substituent or hydrogen atom selected from the group consisting of groups, thiol groups, carboxy groups, hydroxyl groups and succinic anhydride groups, provided that at least two of E ^{1 to} E ³ are epoxy groups And at least one selected from the group consisting of and oxetanyl groups)

In the formula (a1-II), at least two groups represented by R ^a20 and E ¹ , R ^a21 and E ² , and R ^a22 and E ³ , for example, are each represented by the following formula (a1-II a) Are preferably groups, and each is more preferably a group represented by the following formula (a1-IIa). It is preferable that the several group represented by Formula (a1-IIa) couple | bonded with one compound is the same group.
-L-C ^a (a1-IIa)
(In the formula (a1-IIa), L represents a linear, branched or cyclic alkylene group, an arylene group, -O-, -C (= O)-, -NH- and a combination thereof And C ^a is an epoxy group, and in the formula (a1-IIa), L and C ^a may combine to form a cyclic structure.)

  In the formula (a1-IIa), as the linear, branched or cyclic alkylene group as L, an alkylene group having 1 to 10 carbon atoms is preferable, and as the arylene group as L, An arylene group having 5 to 10 carbon atoms is preferable. In the formula (a1-IIa), L represents a linear alkylene group having 1 to 3 carbon atoms, a phenylene group, -O-, -C (= O)-, -NH- and a combination thereof And is preferably at least one of an alkylene group having a linear carbon number of 1 or more and 3 or less, such as a methylene group, or a phenylene group, or these, -O-, -C (= A group consisting of a combination of at least one of O)-and NH- is preferred.

（式（ａ１−ＩＩｂ）中、Ｒ^ａ２３は、水素原子又はメチル基である。） In the case where L and C ^a are combined to form a cyclic structure in the formula (a1-IIa), for example, a branched alkylene group and an epoxy group are combined to form a cyclic structure (alicyclic structure In the case where a structure having an epoxy group of (1) is formed, organic groups represented by the following formulas (a1-IIb) to (a1-IId) can be mentioned.

(In formula (a1-IIb), R ^a23 is a hydrogen atom or a methyl group.)

Hereinafter, although the example of the epoxy compound which has oxiranyl group or an alicyclic epoxy group is shown as an example of a compound represented by Formula (a1-II), it is not limited to these.

(Siloxane epoxy compound represented by the formula (a1-III))
Among the above-mentioned siloxane compounds, compounds having a cyclic siloxane skeleton represented by the following formula (a1-III) (hereinafter, sometimes simply referred to as “cyclic siloxane”) are preferable.

In formula (a1-III), R ^a24 and R ^{a25 each} represent a monovalent group containing an epoxy group or an alkyl group. However, at least two of x1 R ^a24 and x1 R ^{a25 in} the compound represented by the formula (a1-III) are monovalent groups containing an epoxy group. Moreover, x1 in Formula (a1-III) shows an integer greater than or equal to three. In the compounds represented by the formula (a1-III), R ^a24 and R ^a25 may be the same as or different from each other. Moreover, several Ra ²⁴ may be the same or different. The plurality of Ra ²⁵ may also be the same or different.
The alkyl group is, for example, having 1 to 18 carbon atoms such as methyl, ethyl, propyl and isopropyl (preferably 1 to 6 carbon atoms, particularly preferably 1 or more carbon atoms). 3 or less) A linear or branched alkyl group can be mentioned.

  In the formula (a1-III), x1 represents an integer of 3 or more, and in particular, an integer of 3 or more and 6 or less is preferable in terms of excellent crosslinking reactivity when forming a cured film.

  The number of epoxy groups that the siloxane compound has in the molecule is 2 or more, and 2 or more and 6 or less are preferable, and 2 or more and 4 or less are particularly preferable in terms of excellent crosslinking reactivity when forming a cured film. It is.

（上記式中、Ｄ^１及びＤ^２は、それぞれ独立にアルキレン基を表し、ｍｓは０以上２以下の整数を表し、＊は結合手を表す。）
上記アルキレン基としては、例えば、メチレン基、メチルメチレン基、ジメチルメチレン基、ジメチレン基、トリメチレン基等の炭素原子数が１以上１８以下である直鎖状又は分岐鎖状のアルキレン基等を挙げることができる。 Examples of the monovalent group containing an epoxy group include an alicyclic epoxy group and a glycidyl ether group, and an alicyclic epoxy group is preferable, and the following formula (a1-IIIa) or the following formula (a1) is preferable. It is more preferable that it is an alicyclic epoxy group represented by -IIIb).

(In the above formula, D ¹ and D ² each independently represent an alkylene group, ms represents an integer of 0 or more and 2 or less, and * represents a bond.)
Examples of the alkylene group include linear or branched alkylene groups having 1 to 18 carbon atoms, such as methylene, methylmethylene, dimethylmethylene, dimethylene and trimethylene groups. Can.

  The curable composition is, besides the siloxane compound represented by the formula (a1-III), an alicyclic epoxy group-containing cyclic siloxane, an alicyclic epoxy group-containing silicone resin described in JP-A-2008-248169, And a compound having a siloxane skeleton such as an organopolysilsesquioxane resin having at least two epoxy functional groups in one molecule described in JP-A-2008-19422.

  As a siloxane compound, although the cyclic siloxane etc. which have 2 or more epoxy groups in a molecule | numerator represented by a following formula more specifically can be mentioned, this invention is not limited to these. Moreover, as a siloxane compound, for example, trade names "X-40-2670", "X-40-2701", "X-40-2728", "X-40-2738", "X-40-2740" Commercial products such as (manufactured by Shin-Etsu Chemical Co., Ltd.) can be used.

(Episulfide compound)
The type of episulfide compound is not particularly limited as long as the object of the present invention is not impaired. As a preferable episulfide compound, the compound which substituted the oxygen atom in the epoxy group by the sulfur atom is mentioned about the above-mentioned epoxy compound.

(Vinyl ether compound)
The curable compound (A) may or may not contain a vinyl ether compound containing a vinyloxy group.
The vinyl ether compound is not particularly limited as long as it has a vinyloxy group and is a cationically polymerizable compound.
The vinyl ether compound may contain an aromatic group or may not contain an aromatic group.
The vinyl ether compound is preferably a compound having a vinyloxy group bonded to an aromatic group, from the viewpoint that the heat decomposition resistance of the cured product is good.

Preferred specific examples of the vinyl ether compound include vinyl phenyl ether, 4-vinyloxytoluene, 3-vinyloxytoluene, 2-vinyloxytoluene, 1-vinyloxy-4-chlorobenzene, 1-vinyloxy-3-chlorobenzene, and 1-vinylvinyl ether. Vinyloxy-2-chlorobenzene, 1-vinyloxy-2,3-dimethylbenzene, 1-vinyloxy-2,4-dimethylbenzene, 1-vinyloxy-2,5-dimethylbenzene, 1-vinyloxy-2,6-dimethylbenzene, 1-vinyloxy-3,4-dimethylbenzene, 1-vinyloxy-3,5-dimethylbenzene, 1-vinyloxynaphthalene, 2-vinyloxynaphthalene, 2-vinyloxyfluorene, 3-vinyloxyfluorene, 4-vinyloxy- 1,1'-biphenyl, 3-vinyloxy-1,1'- Aromatic monovinyl ether compounds such as phenyl, 2-vinyloxy-1,1'-biphenyl, 6-vinyloxytetralin, and 5-vinyloxytetralin; 1,4-divinyloxybenzene, 1,3-divinyloxybenzene 1,2-Divinyloxybenzene, 1,4-Divinyloxynaphthalene, 1,3-Divinyloxynaphthalene, 1,2-Divinyloxynaphthalene, 1,5-Divinyloxynaphthalene, 1,6- Divinyloxynaphthalene, 1,7-divinyloxynaphthalene, 1,8-divinyloxynaphthalene, 2,3-divinyloxynaphthalene, 2,6-divinyloxynaphthalene, 2,7-divinyloxynaphthalene, 1,2-divinyloxyfluorene, 3,4-divinyloxyfluorene, 2,7-divinyloxyfluorene, 4,4'-divinyloxybi Phenyl, 3,3'-divinyloxybiphenyl, 2,2'-divinyloxybiphenyl, 3,4'-divinyloxybiphenyl, 2,3'-divinyloxybiphenyl, 2,4'-divinyloxy Examples include biphenyl and aromatic divinyl ether compounds such as bisphenol A divinyl ether.
These vinyl ether compounds may be used in combination of two or more.

(Polymer having triazine ring structure)
The polymer having a triazine ring structure is preferably used in combination with the other (A) curable compound described above.
Examples of the above-described polymer having a triazine ring structure (hereinafter, also simply referred to as "triazine ring-containing polymer") include those represented by the following formulas (t1) to (t16).

上記式中、Ｒ及びＲ’は、それぞれ独立して、水素原子、アルキル基、アルコキシ基、アリール基又はアラルキル基を表し、屈折率をより高めるという観点から、ともに水素原子であることが好ましい。Ｒ^１〜Ｒ^３及びＲ^１’〜Ｒ^４’は、それぞれ独立して、水素原子、ハロゲン原子、カルボキシル基、スルホ基、炭素原子数１以上１０以下の分岐構造を有していてもよいアルキル基、または炭素原子数１以上１０以下の分岐構造を有していてもよいアルコキシ基を表し、Ｒ^１０２及びＲ^１０３は、互いに独立して炭素原子数１以上５以下のアルキル基を表す。）

In the above formulas, R and R ′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or an aralkyl group, and both are preferably hydrogen atoms from the viewpoint of further increasing the refractive index. R ^{1 to} R ³ and R ^{1 ′ to} R ^{4 ′} each independently represent a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, or an alkyl which may have a branched structure of 1 to 10 carbon atoms R ¹⁰² and R ¹⁰³ each independently represent an alkyl group having 1 to 5 carbon atoms, which is a group or an alkoxy group which may have a branched structure having 1 to 10 carbon atoms. )

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^３、Ｒ^１’〜Ｒ^４’、Ｒ^１０２及びＲ^１０３は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ³ , R ^{1 ′ to} R ^{4 ′} , R ¹⁰² and R ¹⁰³ have the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^３及びＲ^１’〜Ｒ^４’は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ³ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^３及びＲ^１’〜Ｒ^４’は上記と同じ意味を表し、Ｒ^４は水素原子、ハロゲン原子、カルボキシル基、スルホ基、炭素原子数１以上１０以下の分岐構造を有していてもよいアルキル基、または炭素原子数１以上１０以下の分岐構造を有していてもよいアルコキシ基を表し、Ｒ^１０２及びＲ^１０３は、互いに独立して炭素原子数１以上５以下のアルキル基を表す。）

(Wherein, R, R ′, R ^{1 to} R ³ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as above, and R ⁴ represents a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, one or more carbon atoms Represents an alkyl group which may have a branched structure of 10 or less, or an alkoxy group which may have a branched structure of 1 to 10 carbon atoms, and R ¹⁰² and R ¹⁰³ are each independently carbon Represents an alkyl group having 1 to 5 atoms)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^４、Ｒ^１’〜Ｒ^４’、Ｒ^１０２及びＲ^１０３は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ⁴ , R ^{1 ′ to} R ^{4 ′} , R ¹⁰² and R ¹⁰³ have the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^４及びＲ^１’〜Ｒ^４’は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ⁴ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^３及びＲ^１’〜Ｒ^４’は上記と同じ意味を表し、Ｒ^１０２及びＲ^１０３は、互いに独立して炭素原子数１以上５以下のアルキル基を表す。）

(Wherein, R, R ′, R ^{1 to} R ³ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as above, and R ¹⁰² and R ¹⁰³ are each independently an alkyl having 1 to 5 carbon atoms) Represents a group)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^３、Ｒ^１’〜Ｒ^４’、Ｒ^１０２及びＲ^１０３は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ³ , R ^{1 ′ to} R ^{4 ′} , R ¹⁰² and R ¹⁰³ have the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^３及びＲ^１’〜Ｒ^４’は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ³ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^４及びＲ^１’〜Ｒ^４’は上記と同じ意味を表し、Ｒ^１０２及びＲ^１０３は、互いに独立して炭素原子数１以上５以下のアルキル基を表す。）

(Wherein, R, R ′, R ^{1 to} R ⁴ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as above, and R ¹⁰² and R ¹⁰³ are each independently an alkyl having 1 to 5 carbon atoms) Represents a group)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^４、Ｒ^１’〜Ｒ^４’、Ｒ^１０２及びＲ^１０３は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ⁴ , R ^{1 ′ to} R ^{4 ′} , R ¹⁰² and R ¹⁰³ have the same meaning as described above.)

（式中、Ｒ、Ｒ’、Ｒ^１〜Ｒ^４及びＲ^１’〜Ｒ^４’は、上記と同じ意味を表す。）

(Wherein, R, R ′, R ^{1 to} R ⁴ and R ^{1 ′ to} R ^{4 ′} represent the same meaning as described above.)

The weight average molecular weight (Mw) of the triazine ring-containing polymer is not particularly limited, but is preferably 500 or more and 500,000 or less, more preferably 500 or more and 100,000 or less, and achieving the effects of the present invention From the viewpoint of enhancing the solubility and lowering the viscosity of the obtained solution, it is preferably 50,000 or less, more preferably 30,000 or less, and still more preferably 10,000 or less. .
In the present invention, Mw is an average molecular weight obtained in terms of standard polystyrene by gel permeation chromatography (hereinafter referred to as GPC) analysis.

  The triazine ring-containing polymer can be produced, for example, by the method disclosed in WO 2010/128661.

  The triazine ring-containing polymer has at least one diamine end, and at least one of the diamine ends is sealed with a carbonyl-containing group such as an acyl group, an alkoxycarbonyl group, an aralkyloxycarbonyl group or an aryloxycarbonyl group. Is preferred. Thus, coloration of the triazine ring-containing polymer can be suppressed by sealing the end with a carbonyl-containing group.

Specific examples of the acyl group include acetyl group, ethyl carbonyl group, acryloyl group, methacryloyl group, benzoyl group and the like.
Specific examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.
Examples of the aralkyloxycarbonyl group include benzyloxycarbonyl group and the like.
A phenoxy carbonyl group etc. are mentioned as a specific example of an aryloxy carbonyl group.
Among these, as the end capping group, an acyl group is preferable, and in consideration of availability of a reagent, an acryloyl group, a methacryloyl group, and an acetyl group are more preferable.

As the end-capping method, a known method may be adopted, and for example, it may be treated with an acid halide, an acid anhydride or the like.
In this case, the use amount of the end capping agent is preferably 0.05 equivalent or more and 10 equivalents or less, preferably 0.1 equivalent or more to 1 equivalent of amino group derived from the excess diamino compound not used in the polymerization reaction. Less than equivalent is more preferable, and 0.5 equivalent or more and 2 equivalents or less are still more preferable.

The curable compound (A) may be used alone or in combination of two or more.
The content of the curable compound (A) in the curable composition is not particularly limited as long as the object of the present invention is not impaired. The content of the curable compound (A) in the curable composition is preferably 60 parts by mass or more and 99.9 parts by mass or less, and 75 parts by mass or more, based on 100 parts by mass of the total solid content of the curable composition. 99.5 mass parts or less are more preferable, and 90 mass parts or more and 99 mass parts or less are especially preferable.

<(B) cationic polymerization initiator>
The curable composition may or may not contain a polymerization initiator, but preferably contains a polymerization initiator from the viewpoint of curing acceleration.
However, in the present invention, as a polymerization initiator, the one corresponding to the (C) ionic liquid described later is excluded.
The polymerization initiators may be used alone or in combination of two or more.
The above-mentioned polymerization initiator is preferably (B) a cationic polymerization initiator or an anionic polymerization initiator from the viewpoint that the curable composition is a cationic curing type or an anionic curing type, and (B) a cationic polymerization initiator It is more preferable that

（式（ｂ１）中、Ｒ^ｂ１、Ｒ^ｂ２、Ｒ^ｂ３及びＲ^ｂ４は、それぞれ独立に、置換基を有していてもよい、炭化水素基又は複素環基であり、Ｒ^ｂ１、Ｒ^ｂ２、Ｒ^ｂ３、及びＲ^ｂ４のうちの少なくとも１つが置換基を有してもよい芳香族炭化水素基である。） (Sulfonium salt (B1))
The cationic polymerization initiator (B) is preferably composed of a cationic part and an anionic part, and preferably contains a sulfonium salt (B1) which is an anion represented by the following formula (b1) from the viewpoint of curability.

(In formula (b1), R ^b1 , R ^b2 , R ^b3 and R ^b4 are each independently a hydrocarbon group or a heterocyclic group which may have a substituent, R ^b1 , R ^b2 , At least one of R ^b3 and R ^{b4 is} an aromatic hydrocarbon group which may have a substituent.)

About the said sulfonium salt (B1), the counter cation with respect to the anion represented by the said Formula (b1) which is a cation part is not specifically limited as long as a curable composition cure | hardens favorably. As a counter cation, the following formula (b2):
(R ^b5 ) _{t + 1} -R ^{b6 +} (b2)
(In formula (b2), R ^b5 is a monovalent organic group. R ^b6 is an element of Groups 15 to 17 (IUPAC notation) of valence t. T is an integer of 1 or more and 3 or less. A plurality of R ^b5 may be the same or different, and a plurality of R ^b5 may combine to form a ring with R ^b6 .)

The number of carbon atoms of the hydrocarbon group or heterocyclic group as R ^{b1 to} R ^b4 in the formula (b1) is not particularly limited, but is preferably 1 or more and 50 or less, more preferably 1 or more and 30 or less, and 1 or more and 20 or less Particularly preferred.
Specific examples of the hydrocarbon group as R ^{b1 to} R ^b4 include a linear or branched alkyl group, a linear or branched alkenyl group, a linear or branched alkynyl group, and an aromatic group Group hydrocarbon groups, alicyclic hydrocarbon groups, and aralkyl groups.
As described ^above, R b1 is at least one aromatic group which may have a substituent of a ^{to R b4,} aromatic also have three or more substituents of R b1 ^{to R b4} It is more preferable that it is a group, and it is particularly preferable that all of R ^{b1 to} R ^b4 be an aromatic group which may have a substituent.

As a substituent which the hydrocarbon group as R ^{b1 to} R ^b4 or the heterocyclic group may have, a halogenated alkyl group having 1 to 18 carbon atoms and a halogenated 3 to 18 carbon atoms Aliphatic cyclic group, nitro group, hydroxyl group, cyano group, alkoxy group having 1 to 18 carbon atoms, aryloxy group having 6 to 14 carbon atoms, aliphatic acyl group having 2 to 19 carbon atoms, An aromatic acyl group having 7 to 15 carbon atoms, an aliphatic acyloxy group having 2 to 19 carbon atoms, an aromatic acyloxy group having 7 to 15 carbon atoms, an alkylthio group having 1 to 18 carbon atoms, An arylthio group having 6 to 14 carbon atoms, an amino group in which one or two hydrogen atoms bonded to a nitrogen atom may be substituted with a hydrocarbon group having 1 to 18 carbon atoms, Androgenic atom, and the like.
When the hydrocarbon group as R ^{b1 to} R ^b4 is an aromatic hydrocarbon group, the aromatic hydrocarbon group is an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, And one or more substituents selected from the group consisting of alkynyl groups having 2 to 18 carbon atoms.

When the hydrocarbon group as R ^{b1 to} R ^b4 has a substituent, the number of substituents is not particularly limited, and may be one or more than one. When the number of substituents is plural, the plurality of substituents may be the same or different.

Preferred specific examples in the case where R ^{b1 to} R ^b4 are alkyl groups are methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, straight-chain alkyl groups such as n-nonadecyl group and n-icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, isohexyl group, 2-ethylhexyl And branched chain alkyl groups such as 1,1,3,3-tetramethylbutyl group.

When R ^{b1 to} R ^b4 is an alkenyl group or an alkynyl group, preferable examples thereof include an alkenyl group corresponding to the above group suitable as an alkyl group, and an alkynyl group.

Preferred examples of R ^{b1 to} R ^{b4 which} are aromatic hydrocarbon groups include phenyl group, α-naphthyl group, β-naphthyl group, biphenyl-4-yl group, biphenyl-3-yl group, biphenyl-2 -Yl group, anthryl group, phenanthryl group and the like.

Preferred examples of R ^{b1 to} R ^{b4 when they} are alicyclic hydrocarbon groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentyl group, cyclooctyl group, cyclononyl group, cyclodecyl group and the like. And cycloalkyl aliphatic cyclic hydrocarbon groups such as norbornyl group, adamantyl group, tricyclodecyl group, and pinanyl group.

Preferred examples of R ^{b1 to} R ^{b4 which} are aralkyl groups include benzyl group, phenethyl group, α-naphthylmethyl group, β-naphthylmethyl group, α-naphthylethyl group, and β-naphthylethyl group. It can be mentioned.

Preferred examples of R ^{b1 to} R ^{b4 when it} is a heterocyclic group include thienyl group, furanyl group, selenophenyl group, pyranyl group, pyrrolyl group, oxazolyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, Indolyl group, benzofuranyl group, benzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, acridinyl group, phenothiazinyl group, phenazinyl group, xanthenyl group, thianthrenyl group, phenoxazinyl group, phenoxathinyl group Chromanyl group, isochromanyl group, dibenzothienyl group, xanthonyl group, thioxanthonyl group, dibenzofuranyl group and the like can be mentioned.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is a halogenated alkyl group, preferred examples of the halogenated alkyl group include a trifluoromethyl group and trichloromethyl group. Group, pentafluoroethyl group, 2,2,2-trichloroethyl group, 2,2,2-trifluoroethyl group, 1,1-difluoroethyl group, heptafluoro-n-propyl group, 1,1-difluoro- n-propyl group, 3,3,3-trifluoro-n-propyl group, nonafluoro-n-butyl group, 3,3,4,4,4-pentafluoro-n-butyl group, perfluoro-n-pentyl group And a straight chain halogenated alkyl group such as perfluoro-n-octyl group; hexafluoroisopropyl group, hexachloroisopropyl group, hexafluoroisobu Group, and include branched chain halogenated alkyl groups such as nonafluoro -tert- butyl group.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is a halogenated aliphatic cyclic group, a preferred example of the halogenated aliphatic cyclic group is penta And fluorocyclopropyl group, nonafluorocyclobutyl group, perfluorocyclopentyl group, perfluorocyclohexyl group, perfluoroadamantyl group and the like.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an alkoxy group, preferred examples of the alkoxy group include a methoxy group, an ethoxy group, and an n-propyloxy group , N-butyloxy group, n-pentyloxy group, n-hexyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, n-trioxy group Straight-chain alkoxy groups such as decyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, and n-octadecyloxy; isopropyloxy, isobutyl Oxy group, sec-butyloxy group, tert-butyloxy group, isopentyloxy group, neopentyloxy group, t rt- pentyloxy group, iso-hexyloxy group, a 2-ethylhexyl group, and 1,1,3,3-branched chain alkoxy group such as tetramethyl-butyloxy group.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an aryloxy group, preferred examples of the aryloxy group include a phenoxy group, an α-naphthyloxy group, A beta-naphthyloxy group, a biphenyl-4-yloxy group, a biphenyl-3-yloxy group, a biphenyl-2-yloxy group, an anthryloxy group, and a phenanthryloxy group etc. are mentioned.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an aliphatic acyl group, preferred examples of the aliphatic acyl group include an acetyl group, a propanoyl group and a butanoyl group. Groups, pentanoyl group, hexanoyl group, heptanoyl group, octanoyl group and the like.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an aliphatic acyl group, preferred examples of the aliphatic acyl group include an acetyl group, a propanoyl group and a butanoyl group. Groups, pentanoyl group, hexanoyl group, heptanoyl group, octanoyl group and the like.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an aromatic acyl group, preferred examples of the aromatic acyl group include benzoyl group, α-naphthoyl group And β-naphthoyl group, biphenyl-4-ylcarbonyl group, biphenyl-3-ylcarbonyl group, biphenyl-2-ylcarbonyl group, anthrylcarbonyl group, phenanthrylcarbonyl group and the like.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an aliphatic acyloxy group, preferred examples of the aliphatic acyloxy group include an acetyloxy group and a propanoyloxy Groups, butanoyloxy group, pentanoyloxy group, hexanoyloxy group, heptanoyloxy group, octanoyloxy group and the like.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an aromatic acyloxy group, preferred examples of the aromatic acyloxy group include a benzoyloxy group and an α-naphtho group. Yloxy group, .beta.-naphthoyloxy group, biphenyl-4-ylcarbonyloxy group, biphenyl-3-ylcarbonyloxy group, biphenyl-2-ylcarbonyloxy group, anthrylcarbonyloxy group, and phenanthrylcarbonyloxy group And the like.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an alkylthio group or an arylthio group, preferable examples of the alkylthio group or the arylthio group include the alkoxy described above The group which substituted the oxygen atom in the group or the group suitable as an aryloxy group by the sulfur atom is mentioned.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is an amino group which may be substituted by a hydrocarbon group, even if it is substituted by a hydrocarbon group Preferred examples of the suitable amino group include amino group, methylamino group, ethylamino group, n-propylamino group, dimethylamino group, diethylamino group, methylethylamino group, di-n-propylamino group, and piperidino group. Etc.

When the hydrocarbon group as R ^{b1 to} R ^b4 or the substituent which the heterocyclic group may have is a halogen atom, preferred examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and An iodine atom etc. are mentioned.

Among the above-described substituents which may be possessed by the hydrocarbon group as R ^{b1 to} R ^b4 or the heterocyclic group, carbon atoms are preferred in that the sulfonium salt (B1) has high activity as an initiator. A halogenated alkyl group having 1 to 8 carbon atoms, a halogen atom, a nitro group, and a cyano group are preferable, and a fluorinated alkyl group having 1 to 8 carbon atoms is more preferable.

R ^b5 in the formula (b2) represents an organic group bonded to R ^b6 . It may be the same or different. As R ^b5 , an aromatic hydrocarbon group having 6 to 14 carbon atoms, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, and 2 to 18 carbon atoms And alkynyl groups.
The aromatic hydrocarbon group further includes an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, and an aryl having 6 to 14 carbon atoms. Group, nitro group, hydroxyl group, cyano group, alkoxy group having 1 to 18 carbon atoms, aryloxy group having 6 to 14 carbon atoms, aliphatic acyl group having 2 to 19 carbon atoms, 7 carbon atoms 15 or less aromatic acyl group, aliphatic acyloxy group having 2 to 19 carbon atoms, aromatic acyloxy group having 7 to 15 carbon atoms, alkylthio group having 1 to 18 carbon atoms, 6 carbon atoms An arylthio group having 14 or less, an amino group in which one or two hydrogen atoms bonded to a nitrogen atom may be substituted with a hydrocarbon group having 1 to 18 carbon atoms, It may be substituted with a halogen atom.
Preferred examples of these substituents are the same as the preferred examples of the hydrocarbon group as R ^{b1 to} R ^b4 in formula (b1), or the substituent which the heterocyclic group may have.

In the formula ^{(b2), if R b5} there are a plurality, the plurality of ^{R b5} may form a ring with ^{R b6.} The ring formed by a plurality of R ^b5 and R ^b6 is, in the meantime, in the structure, -O-, -S-, -SO-, -SO _2- , -NH-, -CO-, -COO-, and The bond may be one or more selected from the group consisting of -CONH-.

As a cation part in sulfonium salt (B1), the cation represented by above-mentioned Formula (b2) is preferable. R ^b6 in Formula (b2) is an element of Groups 15 to 17 (IUPAC notation) of valence t. t is an integer of 1 or more and 3 or less.
R ^b6 combines with the organic group R ^b5 to form an onium ion [R ^{b6 +} ]. Among the Group 15 to Group 17 elements, O (oxygen), N (nitrogen), P (phosphorus), S (sulfur), or I (iodine) is preferable. Corresponding onium ions are oxonium ions, ammonium ions, phosphonium ions, sulfonium ions and iodonium ions. Among them, ammonium ion, phosphonium ion, sulfonium ion, and iodonium ion which are stable and easy to handle are preferable, and sulfonium ion and iodonium ion are more preferable in that they are excellent in cationic polymerization performance and crosslinking reaction performance.

  Specific examples of the oxonium ion include oxonium such as trimethyloxonium, diethylmethyloxonium, triethyloxonium, tetramethylenemethyloxonium and the like; 4-methylpyrilinium, 2,4,6-trimethylpyrilinium, 2,6 -Pyririnium such as di-tert-butylpyrilinium and 2,6-diphenylpyrilinium; Chromenium such as 2,4-dimethylchromium, 1,3-dimethylisochromium, and isochromium.

  Specific examples of ammonium ion include tetramethyl ammonium, ethyl trimethyl ammonium, diethyl dimethyl ammonium, triethyl methyl ammonium, and tetra alkyl ammonium such as tetraethyl ammonium; N, N-dimethyl pyrrolidinium, N-ethyl-N-methyl pyrrolidine Pyrrolidinium such as N, N-diethylpyrrolidinium and the like; N, N'-dimethylimidazolinium, N, N'-diethylimidazolinium, N-ethyl-N'-methylimidazolinium, 1,3 Imidazolinium such as 2,4-trimethylimidazolinium and 1,2,3,4-tetramethylimidazolinium; tetrahydropyrimidinium such as N, N'-dimethyltetrahydropyrimidinium; N, N'- Dimethylmorpholinium Piperidinium such as N, N'-diethylpiperidinium; pyridinium such as N-methylpyridinium, N-benzylpyridinium, and N-phenacylpyridinium; imidazolium such as N, N'-dimethylimidazolium; N-methyl quinolium, N-benzyl quinolium and quinolium such as N-phenacyl quinolium; isoquinolium such as N-methyl isoquinolium; benzyl benzo thiazonium; and thiazonium such as phenacyl benzothiazonium; And acridium such as benzyl acridium and phenacyl acridium.

  Specific examples of the phosphonium ion include tetraarylphosphonium ions such as tetraphenylphosphonium, tetra-p-tolylphosphonium, tetrakis (2-methoxyphenyl) phosphonium, tetrakis (3-methoxyphenyl) phosphonium, and tetrakis (4-methoxyphenyl) phosphonium. Phosphonium; triaryl phosphonium such as triphenyl benzyl phosphonium, triphenyl phenacyl phosphonium, triphenyl methyl phosphonium, and triphenyl butyl phosphonium; triethyl benzyl phosphonium, tributyl benzyl phosphonium, tetraethyl phosphonium, tetrabutyl phosphonium, tetrahexyl phosphonium, triethyl phena Tetraphosphorus such as silphosphonium and tributylphenacyl phosphonium Kiruhosuhoniumu, and the like.

  Specific examples of the sulfonium ion include triphenylsulfonium, tri-p-tolylsulfonium, tri-o-tolylsulfonium, tris (4-methoxyphenyl) sulfonium, 1-naphthyldiphenylsulfonium, 2-naphthyldiphenylsulfonium, tris (4 (4) -Fluorophenyl) sulfonium, tri-1-naphthylsulfonium, tri-2-naphthylsulfonium, tris (4-hydroxyphenyl) sulfonium, 4- (phenylthio) phenyldiphenylsulfonium, 4- (p-tolylthio) phenyldi-p-tolyl Sulfonium, 4- (4-methoxyphenylthio) phenylbis (4-methoxyphenyl) sulfonium, 4- (phenylthio) phenylbis (4-fluorophenyl) sulfonium, 4- (phenyl) Thio) phenylbis (4-methoxyphenyl) sulfonium, 4- (phenylthio) phenyldi-p-tolylsulfonium, [4- (4-biphenylylthio) phenyl] -4-biphenylylphenylsulfonium, [4- (2-) Thioxanthonylthio) phenyl] diphenylsulfonium, bis [4- (diphenylsulfonio) phenyl] sulfide, bis [4- {bis [4- (2-hydroxyethoxy) phenyl] sulfonio} phenyl] sulfide, bis {4- [Bis (4-fluorophenyl) sulfonio] phenyl} sulfide, bis {4- [bis (4-methylphenyl) sulfonio] phenyl} sulfide, bis {4- [bis (4-methoxyphenyl) sulfonio] phenyl} sulfide, 4- (4-Benzoyl-2-chlorofe 4- (4-Fluorophenyl) sulfonium, 4- (4-benzoyl-2-chlorophenylthio) phenyldiphenylsulfonium, 4- (4-benzoylphenylthio) phenyl bis (4-fluorophenyl) sulfonium, 4- (4-fluorophenyl) sulfonium 4-Benzoylphenylthio) phenyldiphenylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium, 7-isopropyl-9-oxo-10-thia- 9,10-Dihydroanthracene-2-yldiphenylsulfonium, 2-[(di-p-tolyl) sulfonio] thioxanthone, 2-[(diphenyl) sulfonio] thioxanthone, 4- (9-oxo-9H-thioxanthene-2 -Yl) thiophenyl- 9-Oxo-9H-thioxanthen-2-ylphenylsulfonium, 4- [4- (4-tert-butylbenzoyl) phenylthio] phenyldi-p-tolylsulfonium, 4- [4- (4-tert-butylbenzoyl) Phenylthio] phenyldiphenylsulfonium, 4- [4- (benzoylphenylthio)] phenyldi-p-tolylsulfonium, 4- [4- (benzoylphenylthio)] phenyldiphenylsulfonium, 5- (4-methoxyphenyl) thiaanthrenium Triarylsulfonium such as 5-phenylthiaanthrenium, 5-tolylthiaanthrenium, 5- (4-ethoxyphenyl) thiaanthrenium, and 5- (2,4,6-trimethylphenyl) thiaanthrenium; Phenacyl sulfo Diarylsulfonium such as sodium, diphenyl 4-nitrophenacylsulfonium, diphenylbenzylsulfonium and diphenylmethylsulfonium; phenylmethylbenzylsulfonium, 4-hydroxyphenylmethylbenzylsulfonium, 4-methoxyphenylmethylbenzylsulfonium, 4-acetoxycarbonyloxyphenyl Methylbenzylsulfonium, 4-hydroxyphenyl (2-naphthylmethyl) methylsulfonium, 2-naphthylmethylbenzylsulfonium, 2-naphthylmethyl (1-ethoxycarbonyl) ethylsulfonium, phenylmethylphenacylsulfonium, 4-hydroxyphenylmethylphenacyl Sulfonium, 4-methoxyphenylmethylphenacylsulfonium, 4-acetocarboni Monoaryl sulfoniums such as oxyphenylmethyl phenacyl sulfonium, 2-naphthyl methyl phenacyl sulfonium, 2-naphthyl octadecyl phenacyl sulfonium, and 9-anthracenyl methyl phenacyl sulfonium; dimethyl phenacyl sulfonium, phenacyl tetrahydro thiophenium Dimethylbenzylsulfonium, benzyltetrahydrothiophenium, and trialkylsulfonium such as octadecylmethylphenacylsulfonium.

  In addition, the sulfonium salt (B1) may also include a sulfonium salt comprising an anion portion which is an anion represented by the above formula (b1) and a cation portion which is a sulfonium ion represented by the formula (c1) described later. preferable.

  Specific examples of the iodonium ion include diphenyliodonium, di-p-tolyliodonium, bis (4-dodecylphenyl) iodonium, bis (4-methoxyphenyl) iodonium, (4-octyloxyphenyl) phenyliodonium, bis (4- Examples include iodonium ions such as decyloxy) phenyliodonium, 4- (2-hydroxytetradecyloxy) phenylphenyliodonium, 4-isopropylphenyl (p-tolyl) iodonium, and 4-isobutylphenyl (p-tolyl) iodonium.

Preferred specific examples of the anion represented by the formula (b1) described above are
Tetrakis (4-nonafluorobiphenyl) gallate anion,
Tetrakis (1-heptafluoronaphthyl) gallate anion,
Tetrakis (pentafluorophenyl) gallate anion,
Tetrakis (3,4,5-trifluorophenyl) gallate anion,
Tetrakis (2-nonaphenylbiphenyl) gallate anion,
Tetrakis (2-heptafluoronaphthyl) gallate anion,
Tetrakis (7-nonafluoroanthryl) gallate anion,
Tetrakis (4 '-(methoxy) octafluorobiphenyl) gallate anion,
Tetrakis (2,4,6-tris (trifluoromethyl) phenyl) gallate anion,
Tetrakis (3,5-bis (trifluoromethyl) phenyl) gallate anion,
Tetrakis (2,3-bis (pentafluoroethyl) naphthyl) gallate anion,
Tetrakis (2-isopropoxy-hexafluoronaphthyl) gallate anion,
Tetrakis (9,10-bis (heptafluoropropyl) heptafluoroanthryl) gallate anion,
Tetrakis (9-nonafluorophenanthryl) gallate anion,
Tetrakis (4- [tri (isopropyl) silyl] -tetrafluorophenyl) gallate anion,
Tetrakis (9,10-bis (p-tolyl) -heptafluorophenanthryl) gallate anion,
Tetrakis (4- [dimethyl (t-butyl) silyl] -tetrafluorophenyl) gallate anion,
Monophenyl tris (pentafluorophenyl) gallate anion, monoperfluorobutyl tris (pentafluorophenyl) gallate anion and the like can be mentioned, and more preferably, the following anions can be mentioned.

Preferable specific examples of the counter cation represented by the formula (b2) described above are
4-isopropylphenyl (p-tolyl) iodonium,
Iodonium ions such as 4-isobutylphenyl (p-tolyl) iodonium;
[4- (2-thioxanthonylthio) phenyl] diphenyl sulfonium,
2-[(di-p-tolyl) sulfonio] thioxanthone,
2-[(diphenyl) sulfonio] thioxanthone,
Thioxanthone skeleton-containing sulfonium ions such as 4- (9-oxo-9H-thioxanthen-2-yl) thiophenyl-9-oxo-9H-thioxanthen-2-ylphenylsulfonium;
Sulfonium ion mentioned as a specific example of a cation represented by the below-mentioned formula (c1);
The sulfonium ion mentioned as a specific example of the cation part of the sulfonium salt represented by the below-mentioned formula (c1 ');
Other examples include sulfonium ions shown below.

  As the sulfonium salt (B1), the anion described above as a preferred specific example of the anion represented by the formula (b1) and the preferred specific example of a counter cation represented by the formula (b2) The salt which consists of said cation is preferable. Preferred specific examples of the counter cation represented by the formula (b2) may be two or more in combination.

The content of the (B) cationic polymerization initiator in the curable composition is not particularly limited as long as the object of the present invention is not impaired. The content of the (B) cationic polymerization initiator in the curable composition is the total of the sulfonium salt (B1) and the other cationic polymerization initiator (B2) described later with respect to 100 parts by mass of the (A) curable compound The amount is preferably 0.01 parts by mass or more and 5 parts by mass or less, more preferably 0.05 parts by mass or more and 3 parts by mass or less and particularly preferably 0.1 parts by mass or more and 2 parts by mass or less.
In addition, the content of the sulfonium salt (B1) is preferably 10% by mass or more, more preferably 50% by mass or more based on the total amount of the sulfonium salt (B1) and other cationic polymerization initiators (B2) described later. 70 mass% or more is still more preferable, 90 mass% or more is especially preferable, and 100 mass% is the most preferable.
By using the cationic polymerization initiator (B) in an amount within this range, a cured product excellent in refractive index and yellowing resistance can be formed, and heat resistance (heat decomposition resistance) and adhesion to a substrate are also good. It is easy to obtain a curable composition.

(Other cationic polymerization initiator (B2) different from sulfonium salt (B1))
(B) The cationic polymerization initiator is another cationic polymerization initiator (B2) (hereinafter, also simply referred to as "other cationic polymerization initiator (B2)") different from sulfonium salt (B1), sulfonium salt (also referred to as "other cationic polymerization initiator (B2)"). It may or may not be included together with B1) or alone.
A curable composition can form the hardened | cured material which is excellent in a refractive index and yellowing tolerance by including other cationic polymerization initiators (B2) with a sulfonium salt (B1), Moreover, heat resistance (heat-resistant degradability) And the adhesiveness to a board | substrate is also easy to obtain the curable composition which is favorable.

  The other cationic polymerization initiator (B2) may be a thermal cationic polymerization initiator (B2-1) or a photo cationic polymerization initiator (B2-2), and a photo cationic polymerization initiator (B2-). It is preferable that it is 2). Hereinafter, the heat cationic polymerization initiator (B2-1) and the photo cationic polymerization initiator (B2-2) will be described.

· Thermal cationic polymerization initiator (B2-1)
As the thermal cationic polymerization initiator (B2-1), for example, diphenyliodonium hexafluoroarsenate, diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, triphenylsulfonium tetrafluoroborate, tri-p-tolylsulfonium Hexafluorophosphate, tri-p-tolylsulfonium trifluoromethanesulfonate, bis (cyclohexylsulfonyl) diazomethane, bis (tert-butylsulfonyl) diazomethane, bis (p-toluenesulfonyl) diazomethane, triphenylsulfonium trifluoromethanesulfonate, diphenyl -4-Methylphenylsulfonium trifluoromethanesulfonate, diphenyl-2,4,6-trime Le triphenylsulfonium -p- toluenesulfonate, and diphenyl -p- phenylthiophenylsulfonium hexafluorophosphate, and the like. These may be used in combination of 2 or more types.

  Examples of commercially available thermal cationic polymerization initiators include diazonium salt type initiators such as AMERICURE series (manufactured by American Can), ULTRASET series (manufactured by Adeka), WPAG series (manufactured by Wako Pure Chemical Industries); UVE series Iodonium salt type initiators such as (made by General Electric), FC series (made by 3M), UV9310C (made by GE Toshiba Silicone), and WPI series (made by Wako Pure Chemical Industries); CYRACURE series (Union Carbide) UVI series (General Electric), FC series (3M), CD series (Sartmar), Optomer SP series (Adeka), Optomer CP series (Adeka), Sun Aid SI series (Manufactured by Sanshin Chemical Industries, Ltd.), CI Siri 'S (manufactured by Nippon Soda Co., Ltd.), WPAG series (manufactured by Wako Pure Chemical Industries, Ltd.), CPI series (manufactured by San-Apro Ltd.) sulfonium salt type initiators such as and the like.

（式（ｃ−Ｉ）中、Ｒ^ｃ０１、Ｒ^ｃ０２、及びＲ^ｃ０３は、それぞれ独立に炭素原子数が１以上６以下であるアルキル基である。） It is preferable that a thermal cationic polymerization initiator (B2-1) consists of a cation part and an anion part, and the said cation part contains the compound which is a cation represented by a following formula (c-I). By using such a thermal cationic polymerization initiator (B2-1), the above-mentioned (A) curable compound can be cured well to form a cured product excellent in refractive index and yellowing resistance, and heat resistance (heat decomposition) And the adhesion to the substrate are also easy to obtain a curable composition.

(In formula (c-I), R ^c01 , R ^c02 and R ^c03 each independently represent an alkyl group having 1 to 6 carbon atoms.)

Preferred examples of the alkyl group as R ^c01 , R ^c02 and R ^{c03 in the} formula (c-I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and an isobutyl group, and sec-butyl, tert-butyl, n-pentyl and n-hexyl groups. As an alkyl group, a methyl group or an ethyl group is preferable, and a methyl group is more preferable. It is particularly preferred that R ^c01 , R ^c02 and R ^c03 are all methyl groups.

That is, as a cation represented by Formula (c-I), the cation represented by a following formula (c-II) is preferable.

As the counter anion to the cation represented by the formula (c-I), for _{^{example, AsF 6 -, SbF 6 -}} , PF 6 -, and _{((C 6 F 5) 4} B) - and the like. Among these, ((C ₆ F ₅ ) ₄ B) ⁻ is preferable. Incidentally, _"C 6 _{F 5"} represents a pentafluorophenyl group.

  As a compound which consists of a cation part and an anion part which are represented by said Formula (c-I), the compound which can be obtained as a commercial item can be used. As a commercial item, CXC-1821 (made by King Industries) etc. are mentioned, for example.

And a cation portion made of a cation represented by the formula (c-I), as preferred examples of the compound comprising the anion portion, the cation represented by the formula _{(c-II), AsF 6} - consisting of a a cation represented by quaternary ammonium salts of the formula _{(c-II), SbF 6} - and the cation quaternary ammonium salt, represented by the formula (c-II) consisting of a, PF ₆ ^- consisting of a quaternary a cation represented by ammonium salts, and formula _{(c-II), ((} C 6 F 5) 4 B) - include consists of a quaternary ammonium salt. Among these, the cation represented by the formula _{(c-II), ((} C 6 F 5) 4 B) - the quaternary ammonium salts are more preferably composed of a.

  The compound which consists of a cation part which consists of a cation represented by Formula (c-I), and an anion part may be used individually by 1 type, and may be used in combination of 2 or more type.

. Photo cationic polymerization initiator (B2-2)
As a photocationic polymerization initiator (B2-2), polymerization initiators other than the sulfonium salt (B1) currently used in order to photocure a cationically polymerizable curable composition can be used without a restriction | limiting in particular. As a suitable example of a photocationic polymerization initiator (B2-2), an iodonium salt and a sulfonium salt are mentioned.

  Specific examples of the iodonium salt include, for example, diphenyliodonium tetrakis (pentafluorophenyl) borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, di (4-nonylphenyl) iodonium hexafluorophosphate and the like.

As a photocationic polymerization initiator (B2-2), a sulfonium salt is preferable. Among the sulfonium salts, it is also referred to as a sulfonium salt (hereinafter referred to as “sulfonium salt (Q)”) composed of a cation moiety consisting of a cation represented by the following formula (c1) and an anion moiety. When it is a sulfonium salt which has a cation part which consists of a cation represented by a following formula (c1), the said sulfonium salt is classified as a sulfonium salt (B1).) Is preferable.
When the curable composition contains a sulfonium salt (Q), the curing of the curable composition tends to proceed particularly well.

（式（ｃ１）中、Ｒ^ｃ１及びＲ^ｃ２は独立に、ハロゲン原子で置換されていてもよいアルキル基又は下記式（ｃ２）で表される基を示し、Ｒ^ｃ１及びＲ^ｃ２は相互に結合して式中の硫黄原子とともに環を形成してもよく、Ｒ^ｃ３は下記式（ｃ３）で表される基又は下記式（ｃ４）で表される基を示し、Ａ^ｃ１はＳ、Ｏ、又はＳｅを示し、但し、Ｒ^ｃ１及びＲ^ｃ２は、同時に、ハロゲン原子で置換されていてもよいアルキル基ではない。）

(In the formula (c1), R ^c1 and R ^c2 independently represent an alkyl group which may be substituted with a halogen atom or a group represented by the following formula (c2), and R ^c1 and R ^c2 are mutually bonded And R ^c3 may represent a group represented by the following formula (c3) or a group represented by the following formula (c4), and A ^c1 may be S, O, Or Se, provided that R ^c1 and R ^c2 are not simultaneously an alkyl group which may be substituted by a halogen atom)

（式（ｃ２）中、環Ｚ^ｃ１は芳香族炭化水素環を示し、Ｒ^ｃ４はハロゲン原子で置換されていてもよいアルキル基、ヒドロキシ基、アルコキシ基、アルキルカルボニル基、アルコキシカルボニル基、アシロキシ基、アルキルチオ基、チエニル基、チエニルカルボニル基、フラニル基、フラニルカルボニル基、セレノフェニル基、セレノフェニルカルボニル基、脂肪族複素環基、アルキルスルフィニル基、アルキルスルホニル基、ヒドロキシ（ポリ）アルキレンオキシ基、置換されていてもよいアミノ基、シアノ基、ニトロ基、又はハロゲン原子を示し、ｍ１は０以上の整数を示す。）

(In formula (c2), ring Z ^c1 represents an aromatic hydrocarbon ring, R ^c4 is an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an acyloxy group , Alkylthio group, thienyl group, thienyl carbonyl group, furanyl group, furanyl carbonyl group, selenophenyl group, selenophenyl carbonyl group, aliphatic heterocyclic group, alkylsulfinyl group, alkylsulfonyl group, hydroxy (poly) alkylene oxy group, It is an amino group which may be substituted, a cyano group, a nitro group or a halogen atom, and m1 is an integer of 0 or more.)

（式（ｃ３）中、Ｒ^ｃ５はヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、アリール基、複素環基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ（ポリ）アルキレンオキシ基、置換されていてもよいアミノ基、シアノ基、ニトロ基、もしくはハロゲン原子で置換されていてもよいアルキレン基又は下記式（ｃ５）で表される基を示し、Ｒ^ｃ６はヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、アリール基、複素環基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ（ポリ）アルキレンオキシ基、置換されていてもよいアミノ基、シアノ基、ニトロ基、もしくはハロゲン原子で置換されていてもよいアルキル基又は下記式（ｃ６）で表される基を示し、Ａ^ｃ２は単結合、Ｓ、Ｏ、スルフィニル基、又はカルボニル基を示し、ｍ２は０又は１を示す。）

In the formula (c3), R ^c5 represents a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, Heterocyclic group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy (poly) alkylene oxy group, amino group which may be substituted, cyano group, nitro group or halogen atom in substituted also represents a group represented by an alkylene group or the following formula (c5), R ^c6 is a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, Reylthiocarbonyl group, acyloxy group, arylthio group, alkylthio group, aryl group, heterocyclic group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy (poly) alkyleneoxy group, substituted is an amino group optionally, a cyano group, a nitro group or a group represented by even an alkyl group or the following formula substituted with a halogen atom (c6),, a ^c2 represents a single bond, S, O, A sulfinyl group or a carbonyl group, m 2 is 0 or 1)

（式（ｃ４）中、Ｒ^ｃ７及びＲ^ｃ８は独立に、ヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、アリール基、複素環基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ（ポリ）アルキレンオキシ基、置換されていてもよいアミノ基、シアノ基、ニトロ基、もしくはハロゲン原子で置換されていてもよいアルキレン基又は下記式（ｃ５）で表される基を示し、Ｒ^ｃ９及びＲ^ｃ１０は独立に、ハロゲン原子で置換されていてもよいアルキル基又は上記式（ｃ２）で表される基を示し、Ｒ^ｃ９及びＲ^ｃ１０は相互に結合して式中の硫黄原子とともに環を形成してもよく、Ａ^ｃ３は単結合、Ｓ、Ｏ、スルフィニル基、又はカルボニル基を示し、ｍ３は０又は１を示し、但し、Ｒ^ｃ９及びＲ^ｃ１０は、同時に、ハロゲン原子で置換されていてもよいアルキル基ではない。）

(In formula (c4), R ^c7 and R ^c8 independently represent a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, Alkylthio group, aryl group, heterocyclic group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy (poly) alkyleneoxy group, amino group which may be substituted, cyano group, A nitro group, or an alkylene group which may be substituted by a halogen atom or a group represented by the following formula (c5) is shown, and R ^c9 and R ^c10 are independently an alkyl group which may be substituted by a halogen atom or a group represented by the formula (c2), R ⁹ and R ^c10 may form a ring with the sulfur atom bonded to each other, A ^c3 represents a single bond, shows S, O, a sulfinyl group, or a carbonyl group, m3 represents 0 or 1 Provided that R ^c9 and R ^c10 are not simultaneously an alkyl group which may be substituted by a halogen atom.)

（式（ｃ５）中、環Ｚ^ｃ２は芳香族炭化水素環を示し、Ｒ^ｃ１１はハロゲン原子で置換されていてもよいアルキル基、ヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、アリール基、複素環基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ（ポリ）アルキレンオキシ基、置換されていてもよいアミノ基、シアノ基、ニトロ基、又はハロゲン原子を示し、ｍ４は０以上の整数を示す。）

（式（ｃ６）中、環Ｚ^ｃ３は芳香族炭化水素環を示し、Ｒ^ｃ１２はハロゲン原子で置換されていてもよいアルキル基、ヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、チエニルカルボニル基、フラニルカルボニル基、セレノフェニルカルボニル基、アリール基、複素環基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ（ポリ）アルキレンオキシ基、置換されていてもよいアミノ基、シアノ基、ニトロ基、又はハロゲン原子を示し、ｍ５は０以上の整数を示す。）

(In the formula (c5), ring Z ^c2 represents an aromatic hydrocarbon ring, R ^c11 represents an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group Group, aryloxycarbonyl group, arylthiocarbonyl group, acyloxy group, arylthio group, alkylthio group, aryl group, heterocyclic group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy ( It represents a poly) alkyleneoxy group, an amino group which may be substituted, a cyano group, a nitro group or a halogen atom, and m4 represents an integer of 0 or more.)

(In the formula (c6), ring Z ^c3 represents an aromatic hydrocarbon ring, R ^c12 represents an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group Group, aryloxycarbonyl group, arylthiocarbonyl group, acyloxy group, arylthio group, alkylthio group, thienylcarbonyl group, furanylcarbonyl group, selenophenylcarbonyl group, aryl group, heterocyclic group, aryloxy group, alkylsulfinyl group, An arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy (poly) alkyleneoxy group, an amino group which may be substituted, a cyano group, a nitro group or a halogen atom is shown, and m5 is an integer of 0 or more. )

(Sulfonium salt (Q))
The sulfonium salt (Q) will be described below. Sulfonium salts (Q), in a benzene ring in the formula (c1), characterized in that it is a methyl group is bonded to a carbon atom ortho to the carbon atom to which A ^c1 binds. Since the sulfonium salt (Q) has a methyl group at the above position, it is easy to generate a proton and has high sensitivity to active energy rays such as ultraviolet rays as compared to the conventional sulfonium salt.

In the above formula (c1), it is preferable that both R ^c1 and R ^c2 be a group represented by the above formula (c2). R ^c1 and R ^c2 may be the same or different.
In the above formula (c1), when R ^c1 and R ^c2 combine with each other to form a ring with a sulfur atom in the formula, the number of ring constituting atoms of the ring formed is 3 or more and 10 or less, including the sulfur atom Is preferable, and 5 or more and 7 or less are more preferable. The ring to be formed may be a polycyclic ring, and it is preferable that a 5- to 7-membered ring be condensed.
In the above formula (c1), both R ^c1 and R ^c2 are preferably phenyl groups.
In the above formula (c1), R ^c3 is preferably a group represented by the above formula (c3).
In the above formula (c1), A ^c1 is preferably S or O, and more preferably S.

In the above formula (c2), R ^c4 may be an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkylcarbonyl group, a thienyl carbonyl group, a furanyl carbonyl group, a selenophenyl carbonyl group, or may be substituted It is preferably an amino group or a nitro group, and more preferably an alkyl group which may be substituted by a halogen atom, an alkylcarbonyl group or a thienylcarbonyl group.
In the above formula (c2), m1 can be selected according to the type of ring Z ^{c1 and} is, for example, an integer of 0 or more and 4 or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less May be

In the above formula (c3), R ^c5 is an alkylene group; an hydroxy group, an amino group which may be substituted, or an alkylene group substituted with a nitro group; or a group represented by the above formula (c5) Are preferable, and a group represented by the above formula (c5) is more preferable.
In the above formula (c3), R ^c6 is an alkyl group; an hydroxy group, an amino group which may be substituted, or an alkyl group substituted with a nitro group; or a group represented by the above formula (c6) Are preferable, and a group represented by the above formula (c6) is more preferable.
In the above formula (c3), A ^c2 is preferably S or O, and more preferably S.
In the above formula (c3), m2 is preferably 0.

In the above formula (c4), R ^c7 and R ^c8 are independently represented by an alkylene group; an hydroxy group, an amino group which may be substituted, or a nitro group-substituted alkylene group; or the above formula (a5) Is more preferable than the group represented by the above formula (c5). R ^c7 and R ^c8 may be the same or different.
In the above formula (c4), both of R ^c9 and R ^c10 are preferably a group represented by the above formula (c2). R ^c9 and R ^c10 may be the same or different.
In the above formula (c4), when R ^c9 and R ^c10 combine with each other to form a ring with a sulfur atom in the formula, the number of ring-constituting atoms of the ring formed is 3 or more and 10 or less, including the sulfur atom Is preferable, and 5 or more and 7 or less are more preferable. The ring to be formed may be a polycyclic ring, and it is preferable that a 5- to 7-membered ring be condensed.
In the above formula (c4), A ^c3 is preferably S or O, and more preferably S.
In the above formula (c4), m3 is preferably 0.

In the above formula (c5), R ^c11 is preferably an alkyl group which may be substituted with a halogen atom, a hydroxy group, an amino group which may be substituted, or a nitro group, and is preferably substituted with a halogen atom It is more preferable that it may be an alkyl group.
In the above formula (c5), m4 can be selected according to the type of ring Z ^{c2 and} is, for example, an integer of 0 or more and 4 or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less May be

In the above formula (c6), R ^c12 is an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkylcarbonyl group, a thienyl carbonyl group, a furanyl carbonyl group, a selenophenyl carbonyl group, or may be substituted It is preferably an amino group or a nitro group, and more preferably an alkyl group which may be substituted by a halogen atom, an alkylcarbonyl group or a thienylcarbonyl group.
In the above formula (c6), m5 can be selected according to the type of ring Z ^{c3 and} is, for example, an integer of 0 or more and 4 or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less May be

The cation represented by the above-mentioned formula (c1) usually forms a salt with the monovalent anion X ⁻ . X ⁻ is a monovalent anion corresponding to an acid (HX) generated by irradiating sulfonium salt (Q) with active energy (heat, visible light, ultraviolet light, electron beam, X-ray and the like). As X ⁻ , a monovalent polyatomic anion is suitably mentioned, and MY _a ⁻ , (R f) _b PF _{6 − b} ⁻ , R ^{x 1} _c BY _4-c ⁻ , R ^{x 2} SO ₃ ⁻ , (R ^{x 2} SO ₂ ) An anion represented by ₃ C ⁻ or (R ^{x 2} SO ₂ ) ₂ N ⁻ is more preferable. Further, X ⁻ may be a halogen anion, and examples thereof include fluoride ion, chloride ion, bromide ion and iodide ion.

M represents a phosphorus atom, a boron atom, or an antimony atom.
Y represents a halogen atom (preferably a fluorine atom).

R f represents an alkyl group in which 80 mol% or more of hydrogen atoms are substituted with a fluorine atom (an alkyl group having 1 to 8 carbon atoms is preferable). Examples of the alkyl group to be Rf by fluorine substitution include linear alkyl groups (such as methyl, ethyl, propyl, butyl, pentyl and octyl), branched alkyl groups (such as isopropyl, isobutyl, sec-butyl and tert-butyl) and cyclo Alkyl groups (cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl etc.) and the like can be mentioned. The ratio at which the hydrogen atom of these alkyl groups in Rf is substituted by a fluorine atom is preferably 80 mol% or more, more preferably 90, based on the number of moles of hydrogen atoms contained in the original alkyl group. % Or more, particularly preferably 100%. When the substitution ratio by a fluorine atom is in these preferable ranges, the photosensitivity of the sulfonium salt (Q) is further improved. Particularly preferable Rf is CF ₃ −, CF ₃ CF ₂ ⁻ , (CF ₃ ) ₂ CF ⁻ , CF ₃ CF ₂ CF ₂ ⁻ , CF ₃ CF ₂ CF ₂ CF ₂ ⁻ , (CF ₃ ) ₂ CFCF ₂ ⁻ _{, CF 3 CF 2 (CF 3} ) CF - and _{(CF 3) 3} C ^- and the like. The b R f 's are independent of each other, and thus may be the same or different.

  P represents a phosphorus atom and F represents a fluorine atom.

R ^x1 is part of hydrogen atoms is a phenyl group substituted with at least one element or an electron withdrawing group. Examples of such one element include a halogen atom, and include a fluorine atom, a chlorine atom and a bromine atom. As an electron withdrawing group, a trifluoromethyl group, a nitro group, a cyano group, etc. are mentioned. Among these, a phenyl group in which at least one hydrogen atom is substituted with a fluorine atom or a trifluoromethyl group is preferable. The c R ^x1 are independent of each other, and thus may be the same or different.

  B represents a boron atom.

R ^x2 represents an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; The fluoroalkyl group may be linear, branched or cyclic, and the alkyl group, fluoroalkyl group or aryl group may be unsubstituted or may have a substituent. Examples of the substituent include a hydroxy group, an amino group which may be substituted (for example, those exemplified in the following description of the formulas (c2) to (c6)), a nitro group and the like. It can be mentioned.
In addition, the carbon chain in the alkyl group, fluoroalkyl group or aryl group represented by R ^x2 may have a heteroatom such as oxygen atom, nitrogen atom or sulfur atom. In particular, the carbon chain in the alkyl group or fluoroalkyl group represented by R ^x2 is a divalent functional group (eg, ether bond, carbonyl bond, ester bond, amino bond, amido bond, imide bond, sulfonyl bond, sulfonylamide) It may have a bond, a sulfonylimide bond, a urethane bond and the like).
When the alkyl group, fluoroalkyl group or aryl group represented by R ^x2 has the above substituent, hetero atom or functional group, the number of substituents, hetero atoms or functional groups may be one. It may be two or more.

S represents a sulfur atom, O represents an oxygen atom, C represents a carbon atom, and N represents a nitrogen atom.
a represents an integer of 4 or more and 6 or less.
b is preferably an integer of 1 or more and 5 or less, more preferably an integer of 2 or more and 4 or less, and particularly preferably 2 or 3.
c is preferably an integer of 1 or more and 4 or less, and more preferably 4.

The anion represented _{^{by, SbF 6 - - MY a,}} PF 6 - or BF ₄ ^- anion such as represented and the like.

_{(Rf) b PF 6-b} - as the anion represented by ^{_{the, (CF 3 CF 2) 2}} PF 4 -, (CF 3 CF 2) 3 PF 3 -, ((CF 3) 2 CF) 2 PF 4 ⁻ , ((CF ₃ ) ₂ CF) ₃ PF ₃ ⁻ , (CF ₃ CF ₂ CF ₂ ) ₂ PF ₄ ⁻ , (CF ₃ CF ₂ CF ₂ ) ₃ PF ₃ ⁻ , ((CF ₃ ) ₂ CFCF ₂ ) ₂ PF ₄ ⁻ , ((CF ₃ ) ₂ CFCF ₂ ) ₃ PF ₃ ⁻ , (CF ₃ CF ₂ CF ₂ CF ₂ ) ₂ PF ₄ ⁻ or (CF ₃ CF ₂ CF ₂ CF ₂ ) ₃ PF ₃ ⁻ Table And the like. Among these, (CF ₃ CF ₂ ) ₃ PF ₃ ⁻ , (CF ₃ CF ₂ CF ₂ ) ₃ PF ₃ ⁻ , ((CF ₃ ) ₂ CF) ₃ PF ₃ ⁻ , ((CF ₃ ) ₂ CF) ₂ An anion represented by PF ₄ ⁻ , ((CF ₃ ) ₂ CFCF ₂ ) ₃ PF ₃ ⁻ or ((CF ₃ ) ₂ CFCF ₂ ) ₂ PF ₄ ⁻ is preferable.

R ^x1 _c BY _4-c ^- As the anion represented by, preferably ^R _{x1 c BY 4-c} ^-
(Wherein, R ^x1 represents a phenyl group in which at least a part of hydrogen atoms is substituted with a halogen atom or an electron withdrawing group, Y represents a halogen atom, and c represents an integer of 1 or more and 4 or less).
For example, ((C ₆ F ₅ ) ₄ B) ⁻ , (((CF ₃ ) ₂ C ₆ H ₃ ) ₄ B) ⁻ , ((CF ₃ C ₆ H ₄ ) ₄ B) ⁻ , (( _{C 6 F 5) 2 BF 2} ) -, (C 6 F 5 BF 3) - or _{((C 6 H 3 F 2} ) 4 B) - an anion, and the like represented. Among these, the anion represented by ((C ₆ F ₅ ) ₄ B) ⁻ or (((CF ₃ ) ₂ C ₆ H ₃ ) ₄ B) ⁻ is preferable.

R ^x2 SO ₃ ^- as the anion represented by, trifluoromethanesulfonic acid anion, pentafluoroethanesulfonate anion, heptafluoropropanesulfonate acid anion, nonafluorobutanesulfonic acid anion, pentafluorophenyl sulfonate anion, p- toluene Examples thereof include sulfonic acid anion, benzenesulfonic acid anion, camphorsulfonic acid anion, methanesulfonic acid anion, ethanesulfonic acid anion, propanesulfonic acid anion and butanesulfonic acid anion. Among these, trifluoromethanesulfonic acid anion, nonafluorobutanesulfonic acid anion, methanesulfonic acid anion, butanesulfonic acid anion, camphorsulfonic acid anion, benzenesulfonic acid anion or p-toluenesulfonic acid anion is preferable.

The anion represented ^{_{by, (CF 3 SO 2) 3}} C - - (R x2 SO 2) 3 C, (C 2 F 5 SO 2) 3 C -, (C 3 F 7 SO 2) 3 C - or _{(C 4 F 9 SO 2)} 3 C - anion such as represented and the like.

The anion represented ^{_{by, (CF 3 SO 2) 2}} N - - (R x2 SO 2) 2 N, (C 2 F 5 SO 2) 2 N -, (C 3 F 7 SO 2) 2 N - or _{(C 4 F 9 SO 2)} 2 N - anion, and the like represented.

The monovalent polyatomic _{^{anion, MY a -, (Rf)}} b PF 6-b -, R x1 c BY 4-c -, R x2 SO 3 -, (R x2 SO 2) 3 C - or (R ^In addition to the anion represented by ^{x 2} SO ₂ ) ₂ N ⁻ , perhalogenate ions (ClO ₄ ⁻ , BrO ₄ ^−, etc.), halogenated sulfonate ions (FSO ₃ ⁻ , ClSO ₃ ^−, etc.), sulfate ions (CH 2) ₃ SO ₄ ⁻ , CF ₃ SO ₄ ⁻ , HSO ₄ ⁻ etc., carbonate ion (HCO ₃ ⁻ , CH ₃ CO ₃ ⁻ etc), aluminate ion (AlCl ₄ ⁻ , AlF ₄ ⁻ etc), hexafluorobismic acid ion (BiF ₆ ^-), carboxylate ion _{^{(CH 3 COO -, CF 3}} COO -, C 6 H 5 COO -, CH 3 C 6 H 4 COO -, C 6 F 5 COO -, CF 3 C H ₄ COO ^-, etc.), an aryl boronic acid ions _{^{(B (C 6 H 5)}} 4 -, CH 3 CH 2 CH 2 CH 2 B (C 6 H 5) 3 - , etc.), thiocyanate ion (SCN ^-) and nitrate ion (NO ₃ ^-) and the like can be used.

These X ^- of, in terms of cationic polymerization _{^{performance, MY a -, (Rf)}} b PF 6-b -, R x1 c BY 4-c -, and _{^{(R x2 SO 2) 3 C}} - is represented by Anions are preferable, and SbF ₆ ⁻ , PF ₆ ⁻ , (CF ₃ CF ₂ ) ₃ PF ₃ ⁻ , ((C ₆ F ₅ ) ₄ B) ⁻ , (((CF ₃ ) ₂ C ₆ H ₃ ) ₄ B ) ^-, and _{(CF 3 SO 2) 3 C} - is more preferable.

In the above formulas (c2), (c5), and (c6), as the aromatic hydrocarbon ring, a benzene ring, a fused polycyclic aromatic hydrocarbon ring [for example, a fused bicyclic hydrocarbon ring (for example, naphthalene, C _8-20 fused bicyclic hydrocarbon ring such as ring, preferably C _10-16 fused bicyclic hydrocarbon ring), fused tricyclic aromatic hydrocarbon ring (eg, anthracene ring, phenanthrene ring, etc.), etc. And a fused bicyclic to tetracyclic aromatic hydrocarbon ring] and the like. The aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring.

  In the above formulas (c1) to (c6), examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In the above formulas (c1) to (c6), as the alkyl group, a linear alkyl group having 1 to 18 carbon atoms (methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-octyl) , N-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl etc., branched alkyl groups having 3 to 18 carbon atoms (isopropyl, isobutyl, sec-butyl, tert-butyl) , Isopentyl, neopentyl, tert-pentyl, isohexyl and isooctadecyl etc., and cycloalkyl groups having 3 to 18 carbon atoms (eg cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 4-decylcyclohexyl) etc. It can be mentioned. In particular, in the above formulas (c1), (c2) and (c4) to (c6), the alkyl group which may be substituted by a halogen atom means an alkyl group and an alkyl group substituted by a halogen atom. . As the alkyl group substituted by a halogen atom, a group in which at least one hydrogen atom in the above-mentioned linear alkyl group, branched chain alkyl group or cycloalkyl group is substituted by a halogen atom (monofluoromethyl, difluoromethyl, tri And fluoromethyl and the like. Of the alkyl groups which may be substituted by a halogen atom, a trifluoromethyl group is particularly preferred for R ^c1 , R ^c2 , R ^c9 or R ^c10 , and for R ^c4 , R ^c6 , R ^c11 or R ^c12 Is particularly preferably a methyl group.

  In the formulas (c2) to (c6), as the alkoxy group, a linear or branched alkoxy group having 1 to 18 carbon atoms (methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy) , Tert-butoxy, hexyloxy, decyloxy, dodecyloxy, octadecyloxy and the like) and the like.

  In the above formulas (c2) to (c6), as the alkyl group in the alkylcarbonyl group, a linear alkyl group having 1 to 18 carbon atoms as described above, or a branched alkyl having 3 to 18 carbon atoms Group or a cycloalkyl group having 3 to 18 carbon atoms, and examples of the alkylcarbonyl group include linear, branched or cyclic alkylcarbonyl groups having 2 to 18 carbon atoms Acetyl, propionyl, butanoyl, 2-methylpropionyl, heptanoyl, 2-methylbutanoyl, 3-methylbutanoyl, octanoyl, decanoyl, dodecanoyl, octadecanoyl, cyclopentanoyl, cyclohexanoyl, etc. Be

  In the above formulas (c3) to (c6), examples of the arylcarbonyl group include arylcarbonyl groups having 7 to 11 carbon atoms (such as benzoyl and naphthoyl) and the like.

  In the above formulas (a2) to (a6), as the alkoxycarbonyl group, a linear or branched alkoxycarbonyl group having 2 to 19 carbon atoms (methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxy) having 2 to 19 carbon atoms And the like, carbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, octyloxycarbonyl, tetradecyloxycarbonyl, octadecyloxycarbonyl and the like) and the like.

  In the above formulas (c3) to (c6), examples of the aryloxycarbonyl group include aryloxycarbonyl groups having 7 to 11 carbon atoms (such as phenoxycarbonyl and naphthoxycarbonyl).

  In the above formulas (c3) to (c6), examples of the arylthiocarbonyl group include arylthiocarbonyl groups having 7 to 11 carbon atoms (phenylthiocarbonyl, naphthoxythiocarbonyl and the like) and the like.

  In the above formulas (c2) to (c6), as the acyloxy group, a linear or branched acyloxy group having 2 to 19 carbon atoms (acetoxy, ethyl carbonyloxy, propyl carbonyloxy, isopropyl carbonyloxy, butyl carbonyl) having 2 to 19 carbon atoms And oxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, octylcarbonyloxy, tetradecylcarbonyloxy, octadecylcarbonyloxy and the like) and the like.

  In the above formulas (c3) to (c6), as the arylthio group, an arylthio group having 6 to 20 carbon atoms (phenylthio, 2-methylphenylthio, 3-methylphenylthio, 4-methylphenylthio, 2 -Chlorophenylthio, 3-chlorophenylthio, 4-chlorophenylthio, 2-bromophenylthio, 3-bromophenylthio, 4-bromophenylthio, 2-fluorophenylthio, 3-fluorophenylthio, 4-fluorophenylthio, 2-hydroxyphenylthio, 4-hydroxyphenylthio, 2-methoxyphenylthio, 4-methoxyphenylthio, 1-naphthylthio, 2-naphthylthio, 4- [4- (phenylthio) benzoyl] phenylthio, 4- [4- (4- (phenylthio) benzoylthio] Phenylthio) phenoxy] phenylthio, 4- 4- (phenylthio) phenyl] phenylthio, 4- (phenylthio) phenylthio, 4-benzoylphenylthio, 4-benzoyl-2-chlorophenylthio, 4-benzoyl-3-chlorophenylthio, 4-benzoyl-3-methylthiophenylthio, 4-benzoyl-2-methylthiophenylthio, 4- (4-methylthiobenzoyl) phenylthio, 4- (2-methylthiobenzoyl) phenylthio, 4- (p-methylbenzoyl) phenylthio, 4- (p-ethylbenzoyl) phenylthio 4 And-(p-isopropylbenzoyl) phenylthio, 4- (p-tert-butylbenzoyl) phenylthio and the like) and the like.

  In the above formulas (c2) to (c6), as the alkylthio group, a linear or branched alkylthio group having 1 to 18 carbon atoms (methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec- And butylthio, tert-butylthio, pentylthio, isopentylthio, neopentylthio, tert-pentylthio, octylthio, decylthio, dodecylthio, isooctadecylthio and the like.

  In the above formulas (c3) to (c6), examples of the aryl group include aryl groups having 6 to 10 carbon atoms (such as phenyl, tolyl, dimethylphenyl and naphthyl).

  In the above formula (c2), as the aliphatic heterocyclic group, an aliphatic heterocyclic group (pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl) having 2 to 20 carbon atoms (preferably 4 to 20) as an aliphatic heterocyclic group Tetrahydropyranyl, tetrahydrothiopyranyl, morpholinyl and the like) and the like.

  In the above formulas (c3) to (c6), as a heterocyclic group, a heterocyclic group having 4 to 20 carbon atoms (thienyl, furanyl, selenophenyl, pyranyl, pyrrolyl, oxazolyl, thiazolyl, pyridyl, pyrimidyl, Pyrazinyl, indolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, acridinyl, phenothiazinyl, phenazinyl, xanthenyl, xanthenyl, phenoxazinyl, chromanyl, isochromanyl, isobenzonyl, dibenzothienyl, xanthonil, thionyl And the like.

  In the above formulas (c3) to (c6), examples of the aryloxy group include aryloxy groups having 6 to 10 carbon atoms (such as phenoxy and naphthyloxy).

  In the above formulas (c2) to (c6), as the alkylsulfinyl group, a linear or branched sulfinyl group having 1 to 18 carbon atoms (methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, Isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl, neopentylsulfinyl, tert-pentylsulfinyl, octylsulfinyl, isooctadecylsulfinyl and the like) and the like.

  In the above formulas (c3) to (c6), examples of the arylsulfinyl group include arylsulfinyl groups having 6 to 10 carbon atoms (phenylsulfinyl, tolylsulfinyl, naphthylsulfinyl and the like) and the like.

  In the above formulas (c2) to (c6), as the alkylsulfonyl group, a linear or branched alkylsulfonyl group having 1 to 18 carbon atoms (methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl) Isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, neopentylsulfonyl, tert-pentylsulfonyl, octylsulfonyl, octadecylsulfonyl and the like) and the like.

  In the above formulas (c3) to (c6), examples of the arylsulfonyl group include arylsulfonyl groups having 6 to 10 carbon atoms (phenylsulfonyl, tolylsulfonyl (tosyl group), naphthylsulfonyl and the like) and the like. .

In the above formulas (c2) to (c6), as the hydroxy (poly) alkyleneoxy group, HO (AO) _q- (wherein, AO independently represents an ethyleneoxy group and / or a propyleneoxy group, and q is 1) And the hydroxy (poly) alkyleneoxy group etc. which are represented by the integer of 5 or more are represented.

In the above formulas (c2) to (c6), examples of the amino group which may be substituted include an amino group (—NH ₂ ) and a substituted amino group (methylamino, dimethylamino) having 1 to 15 carbon atoms. Ethylamino, methylethylamino, diethylamino, n-propylamino, methyl-n-propylamino, ethyl-n-propylamino, n-propylamino, isopropylamino, isopropylmethylamino, isopropylethylamino, diisopropylamino, phenylamino, And diphenylamino, methylphenylamino, ethylphenylamino, n-propylphenylamino, isopropylphenylamino and the like) and the like.

  In the above formulas (c3) and (c4), as the alkylene group, a linear or branched alkylene group (methylene group, 1,2-ethylene group, 1,1-ethylene group) having 1 to 18 carbon atoms , Propane-1,3-diyl group, propane-1,2-diyl group, propane-1,1-diyl group, propane-2,2-diyl group, butane-1,4-diyl group, butane-1, 3-diyl group, butane-1,2-diyl group, butane-1,1-diyl group, butane-2,2-diyl group, butane-2,3-diyl group, pentane-1,5-diyl group, Pentane-1,4-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, 2-ethylhexane-1,6-diyl group, nonane- 1,9-diyl group, decane-1,10-diyl Undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, and hexadecane-1 , 16-diyl group etc.) and the like.

The sulfonium salt (Q) can be synthesized, for example, according to the following scheme. Specifically, 1-fluoro-2-methyl-4-nitrobenzene represented by the following formula (c1-1) is represented by the following formula (c1-2) in the presence of a base such as potassium hydroxide Compound is reacted to obtain a nitro compound represented by the following formula (c1-3), and then reduction is performed in the presence of reduced iron to obtain an amine compound represented by the following formula (c1-4) obtain. A diazo compound is obtained by reacting this amine compound with a nitrite (for example, sodium nitrite) represented by MaNO ₂ (wherein, Ma represents a metal atom, for example, an alkali metal atom such as a sodium atom). Then, this diazo compound and CuX ′ (in the formula, X ′ represents a halogen atom such as bromine atom, hereinafter the same) and the cuprous halide and the hydrogen halide represented by HX ′ The reaction is allowed to proceed to obtain a halide represented by the following formula (c1-5). A Grignard reagent is prepared from this halide and magnesium, and then this Grignard reagent is reacted with a sulfoxide compound represented by the following formula (c1-6) in the presence of chlorotrimethylsilane to give a compound of the following formula (c1- The sulfonium salt represented by 7) can be obtained. Further, this sulfonium salt is represented by Mb ⁺ X ′ ′ ⁻ (wherein, Mb ⁺ represents a metal cation, for example, an alkali metal cation such as potassium ion, and X ′ ′ ⁻ represents a monovalent anion represented by X ⁻ (wherein The salt reaction is carried out by reacting with a salt represented by the following formula) except for a halogen anion, whereby a sulfonium salt represented by the following formula (c1-8) can be obtained. In the following formulas (c1-2) to (c-8), R ^{c1 to} R ^c3 and A ^c1 are the same as the above formula (c1).

<Scheme>

Specific examples of the cation represented by the formula (c1), which is the cation part of the sulfonium salt (Q), include the following. As a specific example of the anion part of sulfonium salt (Q), a conventionally well-known thing, such as what was mentioned by description of said X < ^- >, can be mentioned. The sulfonium salt (Q) containing the cation moiety represented by the above formula (c1) can be synthesized according to the above scheme, and the cation moiety can be combined with the desired anion moiety by further salt exchange as necessary. In particular, R ^x1 _c BY _4-c ⁻ (wherein, R ^x1 represents a phenyl group in which at least a portion of hydrogen atoms is substituted with a halogen atom or an electron withdrawing group, Y represents a halogen atom, and c represents The combination with the anion represented by 1) or more and 4 or less is shown.) Is preferable.

In the group of the above-mentioned preferable cation parts, cation parts represented by the following formula are more preferable.

The other cationic polymerization initiator (B2) may contain, in addition to the above sulfonium salt (Q), another photo cationic polymerization initiator other than the sulfonium salt (Q).
The content of the sulfonium salt (Q) in the other cationic polymerization initiator (B2) is not particularly limited, but typically, 70% by mass or more is preferable, 80% by mass or more is more preferable, and 90% by mass or more is particularly preferable Preferably, 100% by weight is most preferred.

The photocationic polymerization initiator (B2-2) may further contain a photocationic polymerization initiator other than the sulfonium salt (B1) and the sulfonium salt (Q) described above, in addition to the sulfonium salt (Q) described above.
As cationic photopolymerization initiators other than the above-mentioned sulfonium salt (B1) and sulfonium salt (Q), various cationic polymerization initiators conventionally used for cationic polymerization can be used without particular limitation.
As the photocationic polymerization initiators other than the above sulfonium salt (B1) and sulfonium salt (Q), as described above, onium salts such as iodonium salts and sulfonium salts are preferable, and other sulfonium salts other than sulfonium salt (Q) Is more preferred.

Hereinafter, the sulfonium salt as a photocationic polymerization initiator other than the aforementioned sulfonium salt (B1) and sulfonium salt (Q) will also be referred to as "sulfonium salt (Q ')".
Sulfonium salts (Q '), as well as the sulfonium salt (Q), 1 monovalent anion X ^- include the aforementioned ^R _{x1 c BY 4-c} ^- preferably comprises.

Examples of the sulfonium salt (Q ′) having a monovalent anion represented by R ^x1 _c BY _4-c ^— include sulfonium salts represented by the following formula (c1 ′).

（式中、Ｒ^ｃ１、Ｒ^ｃ２、Ｒ^ｃ３、Ａ^ｃ１、Ｒ^ｘ１、Ｙ及びｃは上述の通り。）

(Wherein, R ^c1 , R ^c2 , R ^c3 , A ^c1 , R ^x1 , Y and c are as described above)

  Specific examples of the cation moiety of the sulfonium salt (Q ') represented by the above formula (c1') include the following.

Typical examples of the cation part of sulfonium salt (Q ′) also include the following.

The content of the other cationic polymerization initiator (B2) in the curable composition is not particularly limited as long as curing of the curable composition proceeds well. From the viewpoint of easily curing the curable composition, typically, the content of the other cationic polymerization initiator (B2) is (A) a curable compound 100 as the total amount of (B) cationic polymerization initiators. 0 mass part or more and 5 mass parts or less are preferable with respect to mass part, 0.01 mass part or more and 3 mass parts or less are more preferable, and 0.03 mass part or more and 2 mass parts or less are especially preferable.
Moreover, 90 mass% or less is preferable with respect to the total amount of (B) cationic polymerization initiator, as for content of another cationic polymerization initiator (B2), 70 mass% or less is more preferable, and 50 mass% or less is further more Preferably, 30% by mass or less is particularly preferable. It is also preferred that the curable composition does not contain other cationic polymerization initiator (B2).

<Anionic polymerization initiator>
The anionic polymerization initiator may be an anionic polymerization initiator by light or an anionic polymerization initiator by heat.
For example, when the above-mentioned epoxy compound is mixed with the anionic polymerization initiator into the curable composition, an anionic curable curable composition is obtained.
The anionic polymerization initiator by light is not particularly limited. For example, photoactive carbamates such as triphenylmethanol, benzyl carbamate and benzoin carbamate; O-carbamoyl hydroxylamide, O-carbamoyl oxime, aromatic sulfone Amides such as amide, alpha-lactam and N- (2-allylethynyl) amide, and other amides; oxime ester compounds, α-aminoacetophenone, cobalt complexes and the like can be mentioned. Among these, 2-nitrobenzyl cyclohexyl carbamate, triphenylmethanol, o-carbamoyl hydroxylamide, o-carbamoyl oxime, [[(2,6-dinitrobenzyl) oxy] carbonyl] cyclohexylamine, bis [[(2-nitrobenzyl) ) Oxy] carbonyl] hexane 1,6-diamine, 4- (methylthiobenzoyl) -1-methyl-1-morpholinoethane, (4-morpholinobenzoyl) -1-benzyl-1-dimethylaminopropane, N- (2- Nitrobenzyloxycarbonyl) pyrrolidine, hexaamminecobalt (III) tris (triphenylmethyl borate), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone etc. are mentioned as a preferable thing.
Preferred examples other than the above include compounds which are decomposed by the action of light (and / or heat) to generate an imidazole compound.
As the heat-induced anionic polymerization initiator, conventionally used compounds can be used without particular limitation. For example, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-l. Amine-epoxy adduct thermal anion polymerization initiators, thermal base generators comprising amine-isocyanate compounds, or anionic polymerizable curing agents such as dicyandiamides, hydrazines, or aromatic diamines, or different types Examples thereof include composite type anionic polymerization type curing agents comprising a curing agent. Examples of the amine-epoxy adduct thermal anion polymerization initiators include “Amique PN-23”, “Amica PN-40”, Amica PN-50 ”, and“ Amica PN-H ”(all of which are products of Ajinomoto Fine Techno Co., Ltd.) Name), "Hardener X-3661S" (trade name of AC R Inc.), "Hardner X-3670S" (trade name of AC R Co., Ltd.), "Novacua HX-3742" (product of Asahi Kasei Corp.) Name), “Novacua HX-3721” (trade name of Asahi Kasei Corp.), etc. Moreover, as a thermal base generator consisting of an amine-isocyanate compound, for example, “Fujicure FXE-1000” (Fuji Kasei Corp. Trade name), "Fuji Cure FXR-1030" (trade name of Fuji Kasei Co., Ltd.), and the like. Incidentally, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one can also function as an anionic polymerization initiator by the action of light.

  The content of the anionic polymerization initiator in the curable composition is not particularly limited as long as the object of the present invention is not impaired. 0.01 mass part or more and 5 mass parts or less are preferable with respect to 100 mass parts of (A) curable compounds, and, as for content of the anionic polymerization initiator in a curable composition, 0.05 mass part or more and 3 mass parts or less Is more preferably 0.1 parts by mass or more and 2 parts by mass or less.

<(C) ionic liquid having a melting point of 140 ° C. or less (hereinafter, also simply referred to as “(C) ionic liquid”)>
The (C) ionic liquid is a salt that can melt in a temperature range of 140 ° C. or less, and is preferably a stable salt that becomes a liquid at 140 ° C. or less.
The melting point of the ionic liquid (C) is preferably 120 ° C. or less, more preferably 100 ° C. or less, from the viewpoint of achieving the effects of the present invention more reliably, the viewpoint of coating properties, etc. It is further preferable that the temperature is not higher than ° C.
When the curable composition contains the (S) solvent, it is contained in the curable composition at room temperature (25 ° C.) from the viewpoint of achieving the effect of the present invention more reliably, the coating property and the suppression of foreign matter, etc. The solubility of the (C) ionic liquid in the contained (S) solvent is preferably 70% by mass or more, more preferably 80% by mass or more, and particularly preferably 90% by mass or more.

Moreover, 70 parts by mass, 80 parts by mass, or 90 parts by mass of (C) ionic liquid are mixed with 100 parts by mass of (S) solvent contained in the curable composition, as the solubility described above; When treated with a shaker for 5 minutes, it refers to a mass at which no precipitate is observed by visual confirmation of the presence or absence of a precipitate.
(C) The ionic liquid is a salt and is good in ionic conductivity, and by being a liquid having a melting point of 140 ° C. or less, it can be uniformly diffused in the curable composition. Also, the thermal decomposition temperature is relatively high. Therefore, in the curable composition, the dependence on whether it is cationic polymerization or anionic polymerization is low, and the curing reaction can be uniformly promoted, and as a result, the refractive index and the yellowing resistance (especially the yellowing resistance) It is possible to form a cured product which is excellent in heat resistance and adhesion to a substrate.

The (C) ionic liquid is preferably composed of an organic cation and an anion.
From the viewpoint of more surely achieving the effects of the present invention, the organic cation constituting the above (C) ionic liquid may be an alkyl chain quaternary ammonium cation, piperidinium cation, pyrimidinium cation, pyrrolidinium cation, imidazo group It is preferably at least one selected from the group consisting of lithium, pyridinium, pyrazolium, guanidinium, phosphonium and sulfonium cations, and alkyl chain quaternary ammonium cations, piperidinium cations, imidazo. It is more preferable that it is a lithium cation or a phosphonium cation, and from the viewpoint of yellowing resistance, it is still more preferable that it is an imidazolium cation or a phosphonium cation.

Specific examples of the alkyl chain quaternary ammonium cation include quaternary ammonium cations represented by the following formula (L1), and specific examples thereof include tetramethyl ammonium, ethyl trimethyl ammonium, diethyl dimethyl ammonium and triethyl methyl Ammonium, tetraethylammonium, octyltrimethylammonium, hexyltrimethylammonium, methyltrioctylammonium and the like can be mentioned.
Specific examples of the piperidinium cation include piperidinium cation represented by the following formula (L2), and more specifically, for example, 1-propyl piperidinium cation, 1-pentyl piperidinium cation 1,1-Dimethylpiperidinium cation, 1-methyl-1-ethylpiperidinium cation, 1-methyl-1-propylpiperidinium cation, 1-methyl-1-butylpiperidinium cation, 1-methyl 1-Pentyl piperidinium cation, 1-methyl-1-hexyl piperidinium cation, 1-methyl-1-heptyl piperidinium cation, 1-ethyl-1-propyl piperidinium cation, 1-ethyl-1 -Butylpiperidinium cation, 1-ethyl-1-pentylpiperidinium cation, 1- 1-ethyl-1-heptylpiperidinium cation, 1-ethyl-1-heptylpiperidinium cation, 1,1-dipropylpiperidinium cation, 1-propyl-1-butylpiperidinium cation, 1,1-dibutyl The piperidinium cation etc. are mentioned.
Specific examples of the above pyrimidinium cation include, for example, 1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium cation and 1,2,3-trimethyl-1,4,5,6-tetrahydrofuran Pyrimidinium cation, 1,2,3,4-tetramethyl-1,4,5,6-tetrahydropyrimidinium cation, 1,2,3,5-tetramethyl-1,4,5,6-tetrahydro Pyrimidinium cation, 1,3-dimethyl-1,4-dihydropyrimidinium cation, 1,3-dimethyl-1,6-dihydropyrimidinium cation, 1,2,3-trimethyl-1,4-dihydro Pyrimidinium cation, 1,2,3-trimethyl-1,6-dihydropyrimidinium cation, 1,2,3,4-tetramethyl-1,4-dihydropyrimidinium Thione, 1,2,3,4-tetramethyl-1,6-dihydropyrimidinium cation, and the like.

Specific examples of the pyrrolidinium cation include a pyrrolidinium cation represented by the following formula (L3), and more specifically, for example, 1,1-dimethylpyrrolidinium cation, 1-ethyl-1 -Methylpyrrolidinium cation, 1-methyl-1-propylpyrrolidinium cation, 1-methyl-1-butylpyrrolidinium cation, 1-methyl-1-pentylpyrrolidinium cation, 1-methyl-1-hexyl Pyrrolidinium cation, 1-methyl-1-heptylpyrrolidinium cation, 1-ethyl-1-propylpyrrolidinium cation, 1-ethyl-1-butylpyrrolidinium cation, 1-ethyl-1-pentylpyrrolidine Lithium cation, 1-ethyl-1-hexyl pyrrolidinium cation, 1-ethyl-1-heptyl pyrrole Pyridinium cations, 1,1-dipropyl pyrrolidinium cation, 1-propyl-1-butyl pyrrolidinium cation, 1,1-di-butyl pyrrolidinium cation and the like.
Specific examples of the imidazolium cation include an imidazolium cation represented by the following formula (L5), and more specifically, for example, 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation 1-ethyl-3-methylimidazolium cation, 1-propyl-3-methylimidazolium ion, 1-butyl-3-methylimidazolium cation, 1-hexyl-3-methylimidazolium cation, 1-octyl-3 -Methylimidazolium cation, 1-decyl-3-methylimidazolium cation, 1-dodecyl-3-methylimidazolium cation, 1-tetradecyl-3-methylimidazolium cation, 1,2-dimethyl-3-propylimidazolium Cation, 1-ethyl-2,3-dimethyl Mi Dazo cation, 1-butyl-2,3-dimethyl imidazolium cation, 1-hexyl-2,3-dimethyl imidazolium cation and the like.
Specific examples of the pyridinium cation include pyridinium cations represented by the following formula (L6), and more specifically, for example, 1-ethyl pyridinium cation, 1-butyl pyridinium cation, 1-hexyl pyridinium cation, 1 -Butyl-3-methylpyridinium cation, 1-butyl-4-methylpyridinium cation, 1-hexyl-3-methylpyridinium cation, 1-butyl-3,4-dimethylpyridinium cation and the like can be mentioned.

Specific examples of the pyrazolium cation include, for example, 1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium cation and 1,2,3-trimethyl-1,4,5,6-tetrahydrofuran Pyrimidinium cation, 1,2,3,4-tetramethyl-1,4,5,6-tetrahydropyrimidinium cation, 1,2,3,5-tetramethyl-1,4,5,6-tetrahydro Pyrimidinium cation, 1,3-dimethyl-1,4-dihydropyrimidinium cation, 1,3-dimethyl-1,6-dihydropyrimidinium cation, 1,2,3-trimethyl-1,4-dihydro Pyrimidinium cation, 1,2,3-trimethyl-1,6-dihydropyrimidinium cation, 1,2,3,4-tetramethyl-1,4-dihydropyrimidinium cation One, 1,2,3,4-tetramethyl-1,6-dihydropyrimidinium cation, and the like.

  Specific examples of the above phosphonium cations include phosphonium cations represented by the following formula (L4), and tetraalkyl phosphonium cations (for example, tetrabutyl phosphonium ion, tributylhexyl phosphonium ion, etc.) and the like. Specific examples include triethylsulfonium ion, dimethylethylsulfonium ion, triethylsulfonium ion, ethylmethylpropylsulfonium ion, butyldimethylsulfonium ion, 1-methyltetrahydrothiophenium ion, 1-ethyltetrahydrothiophenium ion, 1-propyltetrahydrofuran Thiophenium ions, 1-butyltetrahydrothiophenium ions, or 1-methyl- [1,4] -thioxonium ions, etc. That. Among them, as the sulfonium cation, a sulfonium cation having a cyclic structure such as a tetrahydrothiophenium type or a hexahydrothiopyrylium type 5- or 6-membered ring is preferable, and an oxygen atom or the like is preferably contained in the cyclic structure. It may have a hetero atom.

上記式（Ｌ１）〜（Ｌ４）中、Ｒ^Ｌ１〜Ｒ^Ｌ４は、それぞれ独立に、炭素原子数が１以上２０以下のアルキル基又はＲ^Ｌ７−Ｏ−（ＣＨ_２）_Ｌｎ−で表わされるアルコキシアルキル基（Ｒ^Ｌ７は、メチル基又はエチル基を示し、Ｌｎは１以上４以下の整数を表す。）である。上記式（Ｌ５）中、Ｒ^Ｌ１〜Ｒ^Ｌ４は、各々独立に、炭素原子数が１以上２０以下のアルキル基又はＲ^Ｌ７−Ｏ−（ＣＨ_２）_Ｌｎ−で表わされるアルコキシアルキル基（Ｒ^Ｌ７は、メチル基又はエチル基を示し、Ｌｎは１以上４以下の整数を表す。）又は水素原子である。一般式（Ｌ６）中、Ｒ^Ｌ１〜Ｒ^Ｌ６は、各々独立に、炭素原子数が１〜２０のアルキル基又はＲ^Ｌ７−Ｏ−（ＣＨ_２）_Ｌｎ−で表わされるアルコキシアルキル基（Ｒ^Ｌ７は、メチル基又はエチル基を示し、Ｌｎは１〜４の整数を表す）又は水素原子である。

In the above formulas (L1) to (L4), R ^{L1 to} R ^L4 are each independently an alkyl group represented by an alkyl group having 1 to 20 carbon atoms or R ^L7 -O- (CH ₂ ) _Ln- It is a group (R ^L7 shows a methyl group or an ethyl group, and Ln represents an integer of 1 or more and 4 or less). In the above formula (L5), R ^{L1 to} R ^L4 each independently represents an alkyl group having 1 to 20 carbon atoms, or an alkoxyalkyl group (R ^L7 represented by R ^L7 -O- (CH ₂ ) _Ln- Is a methyl group or an ethyl group, and Ln is an integer of 1 or more and 4 or less) or a hydrogen atom. In general formula (L6), R ^{L1 to} R ^L6 each independently represent an alkyl group having 1 to 20 carbon atoms, or an alkoxyalkyl group (R ^L7 is a group represented by R ^L7 -O- (CH ₂ ) _Ln- Is a methyl group or an ethyl group, L n is an integer of 1 to 4) or a hydrogen atom.

As an anion which comprises said (C) ionic liquid, an organic anion, an inorganic anion, etc. are mentioned, From a viewpoint of achieving the effect of this invention more reliably, it is preferable that it is an organic anion.
From the viewpoint of more reliably achieving the effects of the present invention as the organic anion, carboxylic acid anion, N-acyl amino acid ion, acidic amino acid anion, neutral amino acid anion, alkyl sulfate anion, fluorine-containing compound anion and phenol It is preferably at least one selected from the group consisting of a system anion, and more preferably a carboxylic acid type anion or an N-acyl amino acid ion.

Specific examples of the carboxylic acid type anion include acetate ion, decanoate ion, 2-pyrrolidone-5-carboxylate ion, formate ion, α-lipoate ion, lactate ion, tartrate ion, hippurate ion, N-methyl ion Examples thereof include hippurate ion etc. Among them, acetate ion, 2-pyrrolidone-5-carboxylate ion, formate ion, lactate ion, tartrate ion, hippurate ion and N-methyl hippurate ion are preferable, acetate ion, N- Methyl hippurate ion and formate ion are more preferred.
Specific examples of the N-acyl amino acid ion include N-benzoylalanine ion, N-acetyl phenylalanine ion, aspartate ion, glycine ion, N-acetylglycine ion and the like, and among them, N-benzoylalanine ion, N -Acetyl phenylalanine ion and N-acetyl glycine ion are preferable, and N-acetyl glycine ion is more preferable.

Specific examples of the acidic amino acid anion include aspartate ion, glutamate ion and the like, and specific examples of the neutral amino acid anion include glycine ion, alanine ion, phenylalanine ion and the like.
Specific examples of the alkyl sulfate type anion include methanesulfonic acid ion and the like, and specific examples of the fluorine containing compound type anion include trifluoromethanesulfonic acid ion, hexafluorophosphonic acid ion, trifluorotris (pentafluoromethane) Ethyl) phosphonate ion, bis (trifluoromethanesulfonyl) imide ion, trifluoroacetate ion, tetrafluoroborate ion etc., and specific examples of the above-mentioned phenolic anion include phenol ion, 2-methoxyphenol ion, 2, and 6-di-tert-butylphenol ion etc. are mentioned.

From the group consisting of F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , PF ₆ ⁻ and N (SO ₂ F) ₂ ⁻ from the viewpoint of more surely achieving the effects of the present invention as the above-mentioned inorganic anion It is preferably at least one selected, more preferably BF ₄ ⁻ , PF ₆ ⁻ or N (SO ₂ F) ₂ ⁻ , still more preferably BF ₄ ⁻ or PF ₆ ⁻ .

The above (C) ionic liquid can be produced, for example, by the method disclosed in paragraph 0045 of WO 2014/178254.
The above (C) ionic liquids may be used alone or in combination of two or more.
The content of the (C) ionic liquid is not particularly limited as long as the effects of the present invention can be achieved, but it is 0.0001 parts by mass or more and 1 part by mass or less with respect to 100 parts by mass of the curable compound. Is preferable, and 0.001 to 1 part by mass is more preferable, and 0.002 to 10 parts by mass is further preferable, and 0.003 to 0.07 parts by mass It is particularly preferred that

<(D) Hardening accelerator>
The curable composition may contain (D) a curing accelerator. When the curable composition contains (D) a curing accelerator, the curability of the curable composition is improved together with the refractive index and the yellowing resistance, and the heat resistance (heat decomposition resistance) and the adhesion to the substrate are obtained. Can form a cured product which is particularly good.

(D) As the curing accelerator, for example, urea compounds, tertiary amines and their salts, imidazoles and their salts, phosphine compounds and their derivatives, metal carboxylates, Lewis acids, Bronsted acids and their salts, Tetraphenyl boron salt etc. are mentioned.

  Preferred specific examples of the curing accelerator (D) include 1,8-diazabicyclo (5,4,0) undecene-7, triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, and tris (dimethylaminomethyl) ) Tertiary amines such as phenol; imidazoles such as 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2-heptadecylimidazole; tributyl phosphine, methyl diphenyl phosphine, triphenyl phosphine, Phosphine compounds such as diphenyl phosphine and phenyl phosphine; tetraphenyl phosphonium tetraphenyl borate, triphenyl phosphine tetraphenyl borate, 2-ethyl-4-methylimidazole salt Phenyl borate, and tetraphenyl boron salts such N- methylmorpholine tetraphenylborate and the like.

  Among the (D) curing accelerators described above, phosphine compounds and their derivatives, and tetraphenyl boron salts are preferable. Among the above-mentioned specific examples, triphenyl phosphine and triphenyl phosphine triphenyl borane are preferable.

  The amount of the curing accelerator (D) used is not particularly limited as long as the object of the present invention is not impaired. The amount of the curing accelerator (D) used is preferably 0.01 parts by mass or more and 5 parts by mass or less, and more preferably 0.05 parts by mass or more and 3 parts by mass or less with respect to 100 parts by mass of the (A) curable compound 0.1 parts by mass or more and 2 parts by mass or less are particularly preferable.

<(E) Inorganic filler>
The curable composition may or may not contain (E) an inorganic filler, but from the viewpoint of adjusting the refractive index, it is also preferable to contain (E) an inorganic filler. Even when the content of the curable compound (A) in the curable composition is small or (A) does not contain the curable compound, the refractive index is due to the curable composition containing the (E) inorganic filler. It is also possible to achieve 1.60 or more and 2.20 or less.
As the inorganic filler (E), metal oxide particles are preferable.
Examples of the metal oxide particles include at least one metal oxide particle selected from aluminum, zirconium, titanium, zinc, indium, tin, antimony, lanthanum, cerium, neodymium, gadolinium, holmium, lutetium, hafnium, and tantalum. Be An oxide of zirconium, titanium or cerium can be preferably used, and from the viewpoint of increasing the refractive index, particularly preferably titanium oxide or cerium oxide. The shape of these metal oxide particles is not particularly limited, and the average particle diameter is, for example, 200 nm or less, preferably 50 nm or less, and more preferably 20 nm or less in the dynamic scattering method. The lower limit value is not particularly limited, and is, for example, 0.1 nm or more, and may be 2 nm or more.
The content of the inorganic filler (E) is, for example, 1% by mass or more and 120% by mass or less, preferably 3% by mass or more and 110% by mass or less, and 5% by mass or more and 100% of components excluding the solvent of the curable composition. % Or less is more preferable.

<(F) Sensitizer>
The curable composition may contain (F) a sensitizer. When the curable composition contains (B) a cationic polymerization initiator containing a sulfonium cation and / or an iodonium cation, the curable composition preferably contains a (F) sensitizer. As the sensitizer, known sensitizers conventionally used in combination with various cationic polymerization initiators can be used without particular limitation.
Specific examples of the sensitizer include anthracene, 9,10-dibutoxyanthracene, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, and 9,10- Anthracene compounds such as dipropoxy anthracene; pyrene; 1,2-benzanthracene; perylene; tetracene; coronene; thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone and 2,4-diethyl Thioxanthone compounds such as thioxanthone; Phenothiazines such as phenothiazine, N-methyl phenothiazine, N-ethyl phenothiazine, and N-phenyl phenothiazine; Xanthone; 1-naphthol, 2-naphthol Naphthalene compounds such as 1-methoxynaphthalene, 2-methoxynaphthalene, 1,4-dihydroxynaphthalene, and 4-methoxy-1-naphthol; dimethoxyacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane- Ketones such as 1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, and 4-benzoyl-4'-methyl diphenyl sulfide; N-phenylcarbazole, N-ethylcarbazole, poly-N-vinyl Carbazole compounds such as carbazole and N-glycidyl carbazole; chrysene compounds such as 1,4-dimethoxychrysene and 1,4-di-α-methylbenzyloxychrysene; 9-hydroxyphenanthrene, 9-methoxyphenanthrene, 9-hydride Carboxymethyl-10-methoxy phenanthrene, and phenanthrene compounds such 9-hydroxy-10-ethoxy phenanthrene and the like.
These sensitizers may be used in combination of two or more.

  The use amount of the sensitizer (F) is not particularly limited, but is preferably 1% by mass to 300% by mass, and more preferably 5% by mass to 200% by mass, based on the mass of the cationic polymerization initiator (B). . By using the amount of (F) sensitizer in this range, it is easy to obtain a desired sensitizing effect.

<(G) Antioxidant>
The curable composition may or may not contain (G) an antioxidant, but from the viewpoint of yellowing resistance, it preferably contains (G) an antioxidant.
(G) As the antioxidant, a phenol compound, a phosphite compound, a thioether compound, etc. may be mentioned, and a phenol compound having a molecular weight of 500 or more, a phosphite compound having a molecular weight of 500 or more or a thioether compound having a molecular weight of 500 or more is more preferable. preferable. Moreover, a phenol compound is preferable and, as for (G) antioxidant, the molecular weight 500 or more phenol compound is more preferable.

  As a phenol compound, any phenol compound known as a phenol type color protection agent can be used. As a preferable phenol compound, a hindered phenol compound is mentioned. In particular, compounds having a substituent at a site (ortho position) adjacent to the phenolic hydroxyl group are preferred. As the aforementioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable, and a methyl group, an ethyl group, a propyl group, an isopropyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, isopentyl And t-pentyl, hexyl, octyl, isooctyl and 2-ethylhexyl are more preferred. Also preferred are compounds having a phenol group and a phosphite group in the same molecule.

  As a phosphite compound, tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosphepin-6 -Yl] oxy] ethyl] amine, tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphepin-2-yl And at least one compound selected from the group consisting of oxy] ethyl] amine and ethyl phosphite bis (2,4-ditert-butyl-6-methylphenyl).

  (G) Antioxidants are readily commercially available as Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO -60G, Adekastab AO-80, Adekastab AO-330, Adekastab PEP-36A, Adekastab AO-412S (trade name ADEKA) and the like.

  0.01 to 20 mass% is preferable among the components except the solvent of a curable composition, and, as for content of antioxidant (G), 0.3 to 15 mass% is more preferable. The coloring inhibitor may be only one type or two or more types. In the case of two or more types, the total amount is preferably in the above range.

<Other ingredients>
The curable composition may, if necessary, be a surfactant, a thermal polymerization inhibitor, an antifoaming agent, a silane coupling agent, a colorant (pigment, dye), a resin (a thermoplastic resin, an alkali soluble resin, etc.), Additives such as organic fillers can be included. Any of the additives known in the art can be used. Examples of the surfactant include anionic, cationic and nonionic compounds. Examples of the thermal polymerization inhibitor include hydroquinone and hydroquinone monoethyl ether. Examples of the antifoaming agent include silicone and fluorine. Compounds etc. may be mentioned.

The curable composition containing the essential or optional components described above can form a cured product having excellent refractive index and resistance to yellowing, and also has good heat resistance (heat decomposition resistance) and adhesion to a substrate. It can be suitably used in various applications.
The curable composition is particularly preferably used for forming a transparent film that covers metal wiring and the like in a display device such as a touch panel. Moreover, by using the above-mentioned curable composition, it is difficult to transmit a gas such as water vapor, and it is easy to form a cured film which hardly causes yellowing when exposed to light for a long time. For this reason, the above-mentioned curable composition is preferably used also for formation of a film provided for the purpose of protection, insulation, etc. in a device including an OLED, particularly in OLED lighting.

<(S) Solvent>
The curable composition preferably contains a (S) solvent for the purpose of adjusting the coatability and the viscosity. As the (S) solvent, an organic solvent is typically used. The type of the organic solvent is not particularly limited as long as the components contained in the curable composition can be uniformly dissolved or dispersed.

  (S) Preferred examples of the organic solvent which can be used as the solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol mono n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol mono Ethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether Propylene glycol mono-n-butyl ether, dipropylene glycol (Poly) alkylene glycol mono such as dimonomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc. Alkyl ethers; (poly) alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate Acetates; Ethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, other ethers such as tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate Alkyl esters of lactic acid, etc .; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, Ethyl hydroxyacetate, 2-hydroxy-3-methyl part methyl carbonate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropio Acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate , Other esters such as methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; N-methylpyrrolidone And amides such as N, N-dimethylformamide, N, N-dimethylacetamide and the like. These organic solvents can be used alone or in combination of two or more.

  The use amount of the (S) solvent in the curable composition is not particularly limited. The amount of the (S) solvent used is, for example, 30% by mass or more and 99.9% by mass or less, preferably 50% by mass or more, based on the entire curable composition, from the viewpoint of the coatability of the curable composition It is 98 mass% or less.

<Cured film>
The cured film formed of a cured product obtained by curing the curable composition described above is excellent in the refractive index and the yellowing resistance, and the heat resistance and the adhesion to the substrate are also good.
The thickness of the cured film is not particularly limited, but is preferably 10 nm to 50 μm, more preferably 50 nm to 30 μm, still more preferably 100 nm to 10 μm, and further preferably 300 nm to 5 μm. Is particularly preferred.
The cured film is, for example, a sealing material for an OLED display element, OLED illumination, hard coat, insulating film, antireflective film, interlayer insulating film, carbon hard mask, display panel material (planarizing film, pixel of color filter, organic It is suitable for various uses such as an EL partition, a spacer, an optical member (lens, microlens, wafer level lens, optical fiber, optical waveguide, prism sheet, hologram, high refractive film, retroreflective film) and the like. In addition, since the cured film is excellent in flexibility and is not easily broken, it is suitably used in a flexible display panel and a flexible illumination.
In addition, the cured film is particularly preferably used as a transparent film that covers metal wiring or the like in a display element such as a touch panel.

«Method for producing curable composition»
A curable composition can be manufactured by uniformly mixing each component demonstrated above by a predetermined | prescribed ratio. As a mixing apparatus which can be used for manufacture of a curable composition, 2 rolls, 3 rolls, etc. are mentioned. If the viscosity of the curable composition is sufficiently low, the curable composition may optionally be filtered using a filter having an opening of the desired size to remove insoluble foreign matter.

«Production method of cured product»
The manufacturing method of hardened | cured material will not be specifically limited if it is a method which can harden the curable composition shape | molded in the desired shape.
The curing method is not particularly limited as long as it is a method capable of curing the curable composition, and includes exposure and / or heating, and preferably includes exposure.

  The shape of the molded product is not particularly limited, but it is preferably a film (film) because it is easy to apply heat uniformly to the molded product and easily irradiate the molded product with exposure light uniformly.

Typical examples of the method for producing a cured product as a cured film will be described below.
First, the curable composition is applied on a substrate such as a glass substrate to form a coating film. Examples of the coating method include methods using a contact transfer type coating apparatus such as a roll coater, a reverse coater, and a bar coater, and a non-contact type coating apparatus such as a spinner (rotation type coating apparatus), a slit coater, and a curtain flow coater.
In addition, after the viscosity of the curable composition is adjusted to an appropriate range, the curable composition is applied by a printing method such as an inkjet method or a screen printing method to form a coated film patterned in a desired shape. You may

Next, if necessary, volatile components such as (S) solvent are removed to dry the coated film. Although the drying method is not particularly limited, for example, it is dried under reduced pressure at room temperature using a vacuum drying apparatus (VCD), and then heated to a temperature of 80 ° C. to 120 ° C., preferably 90 ° C. to 100 ° C. on a hot plate. There is a method of drying for a time in the range of 60 seconds to 120 seconds.
After the coating film is formed in this manner, at least one of exposure and heating is applied to the coating film.
The exposure is performed by irradiating an active energy ray such as excimer laser light. Energy dose to be irradiated may differ depending on the composition of the curable composition, for example, 30 mJ / cm ² or more 2000 mJ / cm ² or less are preferred, 50 mJ / cm ² or more 500 mJ / cm ² or less being more preferred.
The temperature at the time of heating is not particularly limited, and is preferably 180 ° C. or more and 280 ° C. or less, more preferably 200 ° C. or more and 260 ° C. or less, and particularly preferably 220 ° C. or more and 250 ° C. or less. The heating time is typically preferably 1 minute to 60 minutes, more preferably 10 minutes to 50 minutes, and particularly preferably 20 minutes to 40 minutes.

  The cured product, particularly the cured film, formed as described above is suitably used for various applications as described above.

  EXAMPLES The present invention will be more specifically described below with reference to examples, but the scope of the present invention is not limited to these examples.

[Examples 1 to 17 and Comparative Examples 1 to 3]
In Examples and Comparative Examples, A1 to A3, which are compounds represented by the following formulas, were used as the (A) curable compound (component (A)).

In Examples and Comparative Examples, B1 and B2, which are compounds represented by the following formulas, were used as the (B) cationic polymerization initiator (component (B)).

In the examples, the following C1 to C5 were used as the (C) ionic liquid ((C) component).
C1: N-butyl-N-methylpiperidinium tetrafluoroborate C2: N-methyl-N-propylpiperidinium tetrafluoroborate C3: 1-ethyl-3-methylimidazolium tetrafluoroborate C4: N-acetylglycine Tetrabutylphosphonium salt C5: 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide

  In the examples, triphenylphosphine triphenyl borane was used as (D) a curing accelerator (component (D)).

  The solid content concentration of the component (A) and component (B) of the type and amount listed in Table 1 and the component (C) and component (D) of the amount listed in Table 1 respectively is 22 mass% Thus, they were dissolved in propylene glycol monomethyl ether acetate to obtain curable compositions of Examples and Comparative Examples.

  Using the obtained curable composition, the refractive index, yellowing resistance, adhesion, and heat resistance of the cured film were evaluated according to the following method. The evaluation results are shown in Table 1.

<Refractive index evaluation>
Each curable composition is coated on a glass substrate using a spin coater, prebaked at 100 ° C. for 120 seconds, and exposed at a dose of 100 mJ / cm ² using an ultraviolet curing machine (broadband) at 230 ° C. 20 Post-baking for a minute was performed to obtain a cured film having a film thickness of about 1 μm. For each cured film, the refractive index at a wavelength of 550 nm was measured and evaluated according to the following criteria.
:: refractive index 1.65 or more ○: refractive index less than 1.65 1.60 or more ×: refractive index less than 1.60

<Yellowing resistance evaluation>
After baking the cured film formed on the substrate in the same manner as in the refractive index evaluation for 3 hours at 250 ° C., the transmittance at a wavelength of 380 nm was measured with a UV-visible spectrophotometer and evaluated according to the following criteria.
:: transmittance 90% or more ○: transmittance less than 90% 85% or more ×: transmittance less than 85%

<Evaluation of adhesion>
Crosscut (1 mm wide grid-like cut) is inserted into the cured film formed on the substrate by the same method as the refractive index evaluation, and the tape test specified in JIS Z 1522 is performed, and the cured film is peeled off or not It was confirmed. A case where there was no peeling was judged as ◎, a case where the number of peeled squares was 5% or less was judged as ○, and a case where the number of peeled squares was more than 5% was judged as x did.

<Heat resistance evaluation>
A cured film was formed on the substrate in the same manner as in the refractive index evaluation. A part of the formed cured film was peeled from the substrate to obtain a sample. The thermogravimetric analysis (TGDTA) in air was performed using the obtained sample to evaluate the heat resistance.
Thermogravimetric analysis was carried out by heating from room temperature (20 ° C.) at a heating rate of 10 ° C./min.
The temperature at which the weight decreased by 5% (Td 5%: 5% weight loss temperature) was measured based on the weight at the beginning of the analysis.
The case where Td5% was 430 ° C. or higher was determined as 、, the case where Td5% was 400 ° C. or more and less than 430 ° C. was determined as ○, and the case where Td5% was less than 400 ° C. was determined as ×.

From the results shown in Table 1, it can be seen that the curable compositions of Examples 1 to 17 containing an ionic liquid can form a cured film compatible with the refractive index and the yellowing resistance. In addition, about the cured film after the said yellowing resistance evaluation, the cured film by the curable composition of Examples 1-17 was colorless and transparent in appearance, and yellowishness was weaker than the cured film of Comparative Examples 1-3. In addition, it can be seen that the adhesion to the substrate and the heat resistance (heat decomposition resistance) are also good.
In particular, it is understood that Examples 4, 5 and 7 to 17 using an imidazolium salt or N-acetylglycine phosphonium salt as an ionic liquid tend to be particularly excellent in yellowing resistance.

On the other hand, it turns out that curable composition of Comparative Examples 1-3 can not achieve coexistence (especially yellowing tolerance) of refractive index and yellowing tolerance.
Further, from the comparison between Example 2 and Comparative Example 1, it is understood that the yellowing resistance is improved by containing the ionic liquid.

Claims (15)

A cationic curable or anionic curable curable composition, wherein
The curable composition which the said curable composition contains the ionic liquid of (C) melting | fusing point 140 degrees C or less, and gives the cured film whose refractive index with respect to the light ray of wavelength 550nm is 1.60 or more and 2.20 or less.   The curable composition according to claim 1, further comprising (A) a curable compound having a functional group containing at least one element selected from the group consisting of N, O, S and Si. A cationic curable or anionic curable curable composition, wherein
Curable composition containing (A) a curable compound having a functional group containing at least one element selected from the group consisting of N, O, S and Si, and (C) an ionic liquid having a melting point of 140 ° C. or less The curable composition, wherein the (A) curable compound comprises at least one selected from the group consisting of an aromatic group, a triazine ring structure, an isocyanuric ring structure and a cyclic siloxane structure. The (A) curable compound is a compound represented by the following formula (a1), a polymer having a triazine ring structure, a compound represented by the following formula (a1-I), and a table represented by the following formula (a1-III) The curable composition of Claim 2 or 3 containing at least 1 sort (s) selected from the group which consists of a siloxane epoxy compound.

(In formula (a1), W ¹ and W ² are each independently represented by the following formula (a2):

Is a group represented by
In formula (a2), ring Z represents an aromatic hydrocarbon ring, X represents a single bond or a group represented by -S-, R ⁰¹ represents a single bond, and an alkylene group having 1 to 4 carbon atoms. Or an alkyleneoxy group having 1 or more and 4 or less carbon atoms, and when R ⁰¹ is an alkyleneoxy group, an oxygen atom in the alkyleneoxy group is bonded to ring Z, and R ⁰² is a monovalent hydrocarbon group , A hydroxyl group, a group represented by -OR ^4a , a group represented by -SR ^4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, -NHR ^4c a group represented by group represented by ^{-N (R} _{4d) 2,} sulfo group, or a monovalent hydrocarbon group, a group represented by ^{-OR 4a,} a group represented by ^{-SR 4b,} an acyl group, an alkoxycarbonyl group, At least a portion monovalent hydrocarbon group, a hydroxyl group, a group represented by ^{-OR 4a} of the hydrogen atoms bonded to carbon atoms contained in the group represented a group represented by NHR ^4c or by ^{-N (R} _{4d) 2,,} A group represented by -SR ^4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, a group represented by -NHR ^4c , -N (R ^4d ) a group represented by _2, shows a substituted group mesyloxy group or a sulfo group,, R ^4a to R ^4d represents a monovalent hydrocarbon radical independently, m represents an integer of 0 or more, R ⁰³ is hydrogen An atom, a vinyl group, a thiiran-2-ylmethyl group, or a glycidyl group,
Both W ¹ and W ² have no hydrogen atom as R ⁰³ ,
Ring Y ¹ and ring Y ² are the same or different aromatic hydrocarbon rings, R is a single bond, a methylene group which may have a substituent, may have a substituent, and 2 carbon atoms Represents an ethylene group which may contain a hetero atom, a group represented by -O-, a group represented by -NH- or a group represented by -S-, and R ^3a and R ^3b independently represent a cyano group or halogen An atom or a monovalent hydrocarbon group is shown, and n1 and n2 independently represent an integer of 0 or more and 4 or less. )

(In the formula (a1-I), X ^a1 , X ^a2 and X ^a3 each independently represent a hydrogen atom or an organic group which may contain an epoxy group, and X ^a1 , X ^a2 and X ^a3 The total number of epoxy groups possessed is 2 or more.)

(In formula (a1-III), R ^a24 and R ^{a25 each} represent an epoxy group-containing monovalent group or an alkyl group, provided that x 1 R ^a24 in the compound represented by formula (a1-III) and x1 pieces of ^{R a25,} at least two is a monovalent group containing an epoxy group. Further, x1 in the formula (a1-III) represents an integer of 3 or more. formula (a1-III) R ^a24 and R ^a25 in the compound represented by the above may be the same or different, and a plurality of R ^a24 may be the same or different, and even if the plurality of R ^a25 are also the same, they are different May be The organic cation constituting the (C) ionic liquid is an alkyl chain quaternary ammonium cation, piperidinium cation, pyrimidinium cation, pyrrolidinium cation, imidazolium cation, pyridinium cation, pyrazolium cation, guanidinium At least one selected from the group consisting of a cation, a phosphonium cation and a sulfonium cation,
From the group consisting of carboxylic acid anions, N-acyl amino acid ions, acidic amino acid anions, neutral amino acid anions, alkyl sulfate anions, fluorine-containing compound anions and phenol anions, which constitute the (C) ionic liquid At least one selected organic anion, and / or
5. The inorganic anion which is at least one selected from the group consisting of F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , PF ₆ ⁻ and N (SO ₂ F) ₂ ^−. The curable composition according to any one of the above.   The content of the said (C) ionic liquid is 0.001 mass part or more and 1 mass part or less with respect to 100 mass parts of curable compounds, The curable composition of any one of Claims 2-5 .   The curable composition according to any one of claims 1 to 6, further comprising (B) a cationic polymerization initiator. 8. The method according to claim 7, wherein the cationic polymerization initiator (B) comprises a sulfonium salt (B1), which is an anion comprising a cationic moiety and an anionic moiety, and the anionic moiety being an anion represented by the following formula (b1): The curable composition as described in-.

(In formula (b1), R ^b1 , R ^b2 , R ^b3 and R ^b4 are each independently a hydrocarbon group or a heterocyclic group which may have a substituent, and R ^b1 and R ^b2 At least one of R ^b3 and R ^{b4 is} an aromatic hydrocarbon group which may have a substituent.   The curable composition according to claim 7 or 8, wherein the (B) cationic polymerization initiator comprises another cationic polymerization initiator (B2) different from the sulfonium salt (B1). A sulfonium salt wherein the sulfonium salt (B1) and / or the other cationic polymerization initiator (B2) consists of a cation part and an anion part, and the cation part is a cation represented by the following formula (c1) The curable composition according to claim 8 or 9, comprising a salt.

(In the formula (c1), R ^c1 and R ^c2 independently represent an alkyl group which may be substituted with a halogen atom or a group represented by the following formula (c2), and R ^c1 and R ^c2 are mutually bonded And R ^c3 may represent a group represented by the following formula (c3) or a group represented by the following formula (c4), and A ^c1 may be S, O, Or Se, provided that R ^c1 and R ^c2 are not simultaneously an alkyl group which may be substituted by a halogen atom)

(In formula (c2), ring Z ^c1 represents an aromatic hydrocarbon ring, R ^c4 is an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an acyloxy group , Alkylthio group, thienyl group, thienyl carbonyl group, furanyl group, furanyl carbonyl group, selenophenyl group, selenophenyl carbonyl group, heterocyclic aliphatic hydrocarbon group, alkylsulfinyl group, alkylsulfonyl group, hydroxy (poly) alkylene Represents an oxy group, an amino group which may be substituted, a cyano group, a nitro group or a halogen atom, and m1 represents an integer of 0 or more.)

In the formula (c3), R ^c5 represents a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, Heterocyclic hydrocarbon group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy (poly) alkylene oxy group, amino group which may be substituted, cyano group, nitro group, or a group represented by even an alkylene group or the following formula substituted with a halogen atom (c5), R ^c6 is a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxy Cal Arylthio carbonyl group, acyloxy group, arylthio group, alkylthio group, aryl group, heterocyclic hydrocarbon group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy (poly ) alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group or a group represented by even an alkyl group or the following formula substituted with a halogen atom (c6),, a ^c2 represents a single Represents a bond, S, O, sulfinyl group or carbonyl group, and m2 represents 0 or 1)

(In formula (c4), R ^c7 and R ^c8 independently represent a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, Alkylthio group, aryl group, heterocyclic hydrocarbon group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, hydroxy (poly) alkyleneoxy group, amino group which may be substituted, Represents a cyano group, a nitro group, an alkylene group which may be substituted with a halogen atom, or a group represented by the following formula (c5), and R ^c9 and R ^c10 may be independently substituted with a halogen atom An alkyl group or a group represented by the above formula (c2) R ^c9 and R ^c10 may combine with each other to form a ring with a sulfur atom in the formula, A ^c3 represents a single bond, S, O, a sulfinyl group or a carbonyl group, and m3 is 0 or 1 provided that R ^c9 and R ^c10 are not simultaneously an alkyl group which may be substituted by a halogen atom.)

(In the formula (c5), ring Z ^c2 represents an aromatic hydrocarbon ring, R ^c11 represents an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group Group, aryloxycarbonyl group, arylthiocarbonyl group, acyloxy group, arylthio group, alkylthio group, aryl group, heterocyclic hydrocarbon group, aryloxy group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group , A hydroxy (poly) alkyleneoxy group, an amino group which may be substituted, a cyano group, a nitro group, or a halogen atom, and m4 represents an integer of 0 or more.)

(In the formula (c6), ring Z ^c3 represents an aromatic hydrocarbon ring, R ^c12 represents an alkyl group which may be substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group Group, aryloxycarbonyl group, arylthiocarbonyl group, acyloxy group, arylthio group, alkylthio group, thienylcarbonyl group, furanylcarbonyl group, selenophenylcarbonyl group, aryl group, heterocyclic hydrocarbon group, aryloxy group, alkyl A sulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy (poly) alkyleneoxy group, an amino group which may be substituted, a cyano group, a nitro group or a halogen atom is shown, and m5 is an integer of 0 or more Indicate The curable composition according to claim 10, wherein R ^c1 and R ^c2 in the formula (c1) are both phenyl groups. Wherein ^{A c1} in the formula (c1) is a S, curable composition according to claim 10 or 11.   The cured film which consists of hardened | cured material of the curable composition of any one of Claims 1-12. A step of forming the curable composition according to any one of claims 1 to 12 into a predetermined shape;
Performing heating, exposure, or exposure and heating on the formed curable composition;
A method of producing a cured product comprising: The manufacturing method of the hardened | cured material of Claim 14 which shaping | molding of the said curable composition is formation of a coating film, and performs at least one of exposure and heating with respect to the said coating film.