Composition and photosensitive composition

Abstract

The present invention provides a photosensitive composition that is resistant to excessive weight loss of the composition or components in the photosensitive composition (components other than the solvent when the composition or photosensitive composition contains a solvent) even when heated, and in which inorganic fine particles are stably dispersed for a long period of time, a cured product of the photosensitive composition, a compound that is preferably incorporated into the photosensitive composition, and a method for producing the compound. [Solution] In a composition containing a photopolymerizable compound (A) and inorganic fine particles (B), or a photosensitive composition containing a photopolymerizable compound (A), inorganic fine particles (B), and an initiator (C), a compound with a specific structure having a radically polymerizable group-containing group or a cationically polymerizable group-containing group is used as the photopolymerizable compound (A).

Description

[Technical Field]

[0001] The present invention relates to a composition containing a photopolymerizable compound (A) and inorganic fine particles (B), a photosensitive composition, a cured product of the photosensitive composition, a compound that is preferably incorporated into the photosensitive composition, and a method for producing the compound. [Background technology]

[0002] Conventionally, various inorganic particles have been blended into compositions used to form various functional materials in order to impart functionality to the materials. For example, high refractive index materials are used to form optical components. As high refractive index materials, for example, compositions in which metal oxide particles such as titanium oxide or zirconium oxide are dispersed in an organic component are used. As a composition for forming such a highly refractive material, an energy ray-curable composition containing a metal oxide (A) having a specific particle size, a (meth)acrylate (B), and a photopolymerization initiator (C) has been proposed (see Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2017-214465 Summary of the Invention [Problem to be solved by the invention]

[0004] As described above, a cured product with a high refractive index can be formed using the composition described in Patent Document 1. However, when a functional material such as a high refractive index material is formed using a conventional composition such as that described in Patent Document 1, the weight of components other than the solvent in the composition is likely to be excessively reduced when the composition is heated in the process of forming the functional material. Furthermore, in conventional compositions such as those described in Patent Document 1, there is also the problem that inorganic fine particles are difficult to disperse stably for a long period of time.

[0005] The present invention has been made in consideration of the above-mentioned problems, and aims to provide a composition and photosensitive composition in which the weight of the components in the composition or photosensitive composition (components other than the solvent if the composition or photosensitive composition contains a solvent) is unlikely to decrease excessively even when heated, and in which inorganic fine particles are stably dispersed for a long period of time, a cured product of the photosensitive composition, a compound that is preferably incorporated into the aforementioned composition and photosensitive composition, and a method for producing the compound. [Means for solving the problem]

[0006] The present inventors have found that the above-mentioned problems can be solved by using a compound having a specific structure containing a radically polymerizable group or a cationically polymerizable group as the photopolymerizable compound (A) in a composition containing a photopolymerizable compound (A) and inorganic fine particles (B), or in a photosensitive composition containing a photopolymerizable compound (A), inorganic fine particles (B), and an initiator (C), and have thus completed the present invention. Specifically, the present invention provides the following.

[0007] A first aspect of the present invention comprises a photopolymerizable compound (A) and inorganic fine particles (B), The photopolymerizable compound (A) is represented by the following formula (A1): R a01 -X a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -R a03 ···(A1) (In formula (A1), R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group, R a02 , and R a04 each independently represents an alkylene group optionally interrupted by one or more O and / or S; X a01 , X a02 , Xa03 , and X a04 are each independently O or S, Ph 1 , and Ph 2 each independently represents a phenylene group optionally substituted with an alkyl group having 1 to 5 carbon atoms, R a02 The number of O and / or S contained in the alkylene group as R a04 and the number of O and / or S contained in the alkylene group as The compound represented by the formula (A1) does not simultaneously have a radical polymerizable group-containing group and a cationically polymerizable group-containing group. A composition comprising a compound represented by the formula:

[0008] A second aspect of the present invention is a composition comprising a photopolymerizable compound (A), inorganic fine particles (B), and an initiator (C), The photopolymerizable compound (A) is represented by the following formula (A1): R a01 -X a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -R a03 ···(A1) (In formula (A1), R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group, R a02 , and R a04 each independently represents an alkylene group optionally interrupted by one or more O and / or S; X a01 , X a02 , X a03 , and X a04 are each independently O or S, Ph 1 , and Ph 2each independently represents a phenylene group optionally substituted with an alkyl group having 1 to 5 carbon atoms, R a02 The number of O and / or S contained in the alkylene group as R a04 and the number of O and / or S contained in the alkylene group as The compound represented by the formula (A1) does not simultaneously have a radical polymerizable group-containing group and a cationically polymerizable group-containing group. The photosensitive composition includes a compound represented by the formula:

[0009] A third aspect of the present invention is a cured product of the photosensitive composition according to the second aspect.

[0010] A fourth aspect of the present invention is a compound represented by the following formula (A1): R a01 -X a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -R a03 ···(A1) (In formula (A1), R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group, R a02 , and R a04 each independently represents an alkylene group optionally interrupted by one or more O and / or S; X a01 , X a02 , X a03 , and X a04 are each independently O or S, Ph 1 , and Ph 2 each independently represents a phenylene group optionally substituted with an alkyl group having 1 to 5 carbon atoms, R a02 The number of O and / or S contained in the alkylene group as R a04and the number of O and / or S contained in the alkylene group as The compound represented by formula (A1) does not simultaneously have a radical polymerizable group-containing group and a cationically polymerizable group-containing group. is expressed as However, X a01 , and X a02 are both S and X a01 But Ph 1 In Ph 1 and Ph 2 and binds to the para position relative to S, which connects X a02 But Ph 2 In Ph 1 and Ph 2 When the bond is para to S that connects a02 , and R a04 is a compound that is not a group represented by -CH2CH2-O-CH2CH2-.

[0011] A fifth aspect of the present invention relates to a method for producing a compound represented by the following formula (A1-d): -X of the compound represented by the following formula (A1-d): a03 The terminal hydrogen atom represented by -H is R a01 and is substituted with a group represented by -X a04 The terminal hydrogen atom represented by -H is R a03 and substituting a group represented by the formula: HX a01 -Ph 1 -S-Ph 2 -X a02 -H···(A1-a) HX a03 -R a02 -Hal···(A1-b) HX a04 -R a04 -Hal···(A1-c) HX a03 -R a02 -X a01 -Ph1 -S-Ph 2 -X a02 -R a04 -X a04 -H···(A1-d) (In formula (A1-a), formula (A1-b), formula (A1-c), and formula (A1-d), R a0 R a02 , R a04 , X a01 ~X a04 , Ph.D. 1 , and Ph 2 are the same as those in formula (A1), and Hal is a halogen atom.

[0012] A sixth aspect of the present invention is a method for producing a compound according to the fourth aspect, comprising reacting a compound represented by the following formula (A1-a), a compound represented by the following formula (A1-e), and a compound represented by the following formula (A1-f) in the presence of a base to obtain a compound represented by formula (A1). HX a01 -Ph 1 -S-Ph 2 -X a02 -H···(A1-a) R a01 -X a03 -R a02 -Hal···(A1-e) R a03 -X a04 -R a04 -Hal···(A1-f) (In formula (A1-a), formula (A1-e), and formula (A1-f), R a01 ~R a04 , X a01 ~X a04 , Ph.D. 1 , and Ph 2 are the same as those in formula (A1), and Hal is a halogen atom. [Effects of the Invention]

[0013] According to the present invention, it is possible to provide a composition in which the weight of components other than the solvent is unlikely to decrease excessively even when heated, and in which inorganic fine particles are stably dispersed for a long period of time, a photosensitive composition, a cured product of the photosensitive composition, a compound that is preferably incorporated into the aforementioned composition and photosensitive composition, and a method for producing the compound. DETAILED DESCRIPTION OF THE INVENTION

[0014] ≪Composition≫ The composition contains a photopolymerizable compound (A) and inorganic fine particles (B). Such a composition is essentially an inorganic fine particle dispersion composition, and after appropriately blending an initiator for curing the photopolymerizable compound (A), it is used to form a functional material having properties according to the type of inorganic fine particles (B). The photopolymerizable compound (A) is The following formula (A1): R a01 -X a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -R a03 ···(A1) (In formula (A1), R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group, R a02 , and R a04 each independently represents an alkylene group optionally interrupted by one or more O and / or S; X a01 , X a02 , X a03 , and X a04 are each independently O or S, Ph 1 , and Ph 2 each independently represents a phenylene group optionally substituted with an alkyl group having 1 to 5 carbon atoms, R a02The number of O and / or S contained in the alkylene group as R a04 and the number of O and / or S contained in the alkylene group as The compound represented by the formula (A1) does not simultaneously have a radical polymerizable group-containing group and a cationically polymerizable group-containing group. The compound includes compounds represented by the formula: By including the compound represented by the formula (A1) in the composition, the weight of components other than the solvent is less likely to decrease excessively even when the composition is heated, and the inorganic fine particles are stably dispersed in the composition for a long period of time. The essential and optional components that the composition may contain are described below.

[0015] <Photopolymerizable compound (A)> The composition contains a photopolymerizable compound (A). The photopolymerizable compound (A) is a compound having a radically polymerizable group-containing group or a cationically polymerizable group-containing group.

[0016] The radical polymerizable group-containing group typically includes a group containing an ethylenically unsaturated double bond. As the ethylenically unsaturated double bond-containing group, a vinyl group or an alkenyl group-containing group such as an allyl group is preferred, and a (meth)acryloyl group-containing group is more preferred. Typical examples of the cationic polymerizable group-containing group include epoxy group-containing groups, oxetanyl group-containing groups, vinyloxy group-containing groups, and vinylthio group-containing groups. Among these, epoxy group-containing groups and vinyloxy group-containing groups are preferred. As the epoxy group-containing group, alicyclic epoxy group-containing groups and glycidyl groups are preferred. Note that an alicyclic epoxy group is an aliphatic cyclic group in which two adjacent ring-constituting carbon atoms in the aliphatic cyclic group are bonded via an oxygen atom. In other words, the alicyclic epoxy group has an epoxy group containing a three-membered ring consisting of two carbon atoms and one oxygen atom on the aliphatic ring.

[0017] In the specification and claims of this application, (meth)acrylic means both acrylic and methacrylic, (meth)acryloyl means both acryloyl and methacryloyl, and (meth)acrylate means both acrylate and methacrylate.

[0018] [Compound (A1)] As described above, the photopolymerizable compound (A) is represented by the following formula (A1): R a01 -X a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -R a03 ···(A1) (In formula (A1), R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group, R a02 , and R a04 each independently represents an alkylene group optionally interrupted by one or more O and / or S; X a01 , X a02 , X a03 , and X a04 are each independently O or S, Ph 1 , and Ph 2 each independently represents a phenylene group optionally substituted with an alkyl group having 1 to 5 carbon atoms, R a02 The number of O and / or S contained in the alkylene group as R a04 and the number of O and / or S contained in the alkylene group as The compound represented by the formula (A1) does not simultaneously have a radical polymerizable group-containing group and a cationically polymerizable group-containing group. The compound includes compounds represented by the formula: In the specification of the present application, the compound represented by formula (A1) is also referred to as "compound (A1)".

[0019] In formula (A1), Ph 1 , and Ph 2 are each independently a phenylene group which may be substituted with an alkyl group having 1 to 5 carbon atoms. 1 , and Ph 2 The phenylene group as may be any of an o-phenylene group, an m-phenylene group, and a p-phenylene group, and is preferably a p-phenylene group.

[0020] Ar a01 The aromatic group as may be substituted with one or more groups selected from the group consisting of an alkyl group having from 1 to 5 carbon atoms, a cyano group, and a halogen atom. Ph 1 , and Ph 2 There is no particular limitation on the number of alkyl groups as substituents bonded to the phenylene group as the alkyl group. Examples of alkyl groups having 1 to 5 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, sec-pentyl, and tert-pentyl groups. Of these groups, methyl and ethyl groups are preferred.

[0021] R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group. The radical polymerizable group and the cationically polymerizable group are as described above. R a01 , and R a03 The radical polymerizable group-containing group as R is preferably a (meth)acryloyl group-containing group, more preferably a (meth)acryloyl group. a01 , and R a03As the cationically polymerizable group-containing group as above, a vinyl group, a vinyloxy group-containing group, and an epoxy group-containing group are preferred, a vinyl group and an epoxy group-containing group are more preferred, and an alicyclic epoxy group-containing group and a glycidyl group are more preferred. A vinyl group is generally a radical polymerizable group, but in formula (A1), R a01 , and R a03 is a vinyl group, the vinyl group is O or S. a03 , or X a04 In addition, a vinyloxy group or a vinylthio group, which is a cationically polymerizable group, is formed. a01 , and R a03 The vinyl group as the cationically polymerizable group is not a radically polymerizable group. The alicyclic epoxy group-containing group is preferably an alicyclic epoxy group-containing group represented by formula (a1-IIIa) or formula (a1-IIIb) described below.

[0022] R a02 , and R a04 are each independently an alkylene group which may be interrupted by one or more O and / or S. a02 , and R a04 is preferably an alkylene group interrupted by one or more O and / or S. R a02 , and R a04 The number of carbon atoms in the alkylene group which may be interrupted by one or more O and / or S is not particularly limited as long as the desired effect is not impaired.

[0023] R a02 , and R a04 The alkylene group, which may be interrupted by one or more O and / or S, as represented by (ma), is preferably a group consisting of ma aliphatic chain saturated hydrocarbon groups selected from alkylene groups having from 1 to 4 carbon atoms, alkanetriyl groups having from 1 to 4 carbon atoms, and alkyl groups having from 1 to 4 carbon atoms, and (ma-1) O and / or S linking the ma aliphatic chain saturated hydrocarbon groups. Here, ma is an integer between 2 and 6.

[0024] Suitable examples of alkylene groups having 1 to 4 carbon atoms include methylene, ethane-1,2-diyl (ethylene), propane-1,2-diyl, propane-1,3-diyl, butane-1,2-diyl, butane-1,3-diyl, and butane-1,4-diyl. Of these groups, ethane-1,2-diyl (ethylene), propane-1,2-diyl, and propane-1,3-diyl are preferred. Preferred examples of the alkanetriyl group having 1 to 4 carbon atoms include a propane-1,2,3-triyl group, a butane-1,2,3-triyl group, and a butane-1,2,4-triyl group. Of these groups, a propane-1,2,3-triyl group is preferred. Preferred examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Among these groups, a methyl group and an ethyl group are preferred.

[0025] R a02 , and R a04 The alkylene group, which may be interrupted by one or more O and / or S, as represented by the formula (1), is preferably a group consisting of ma alkylene groups having from 1 to 4 carbon atoms and (ma-1) O and / or S atoms connecting the ma alkylene groups. Here, ma is an integer between 2 and 6.

[0026] R a02 , and R a04 Specific preferred examples of the alkylene group which may be interrupted by one or more O and / or S include the following groups: -CH2CH2-O-CH2CH2- -(CH2CH2-O)2-CH2CH2- -(CH2CH2-O)3-CH2CH2- -(CH2CH2-O)4-CH2CH2- -(CH2CH2-O)5-CH2CH2- -C(CH3)HCH2-O-C(CH3)HCH2- -(C(CH3)HCH2)2-O-C(CH3)HCH2- -(C(CH3)HCH2)3-O-C(CH3)HCH2- -(C(CH3)HCH2)4-O-C(CH3)HCH2- -(C(CH3)HCH2)5-O-C(CH3)HCH2- -(C(CH3)HCH2)2-O-C(CH3)HCH2- -(C(CH3)HCH2)3-O-C(CH3)HCH2- -(C(CH3)HCH2)4-O-C(CH3)HCH2- -(C(CH3)HCH2)5-O-C(CH3)HCH2- -CH2CH2CH2-O-CH2CH2CH2- -(CH2CH2CH2)2-O-CH2CH2CH2- -(CH2CH2CH2)3-O-CH2CH2CH2- -(CH2CH2CH2)4-O-CH2CH2CH2- -(CH2CH2CH2)5-O-CH2CH2CH2- -CH2C(OCH3)HCH2- -CH2C(OCH2CH3)HCH2- -CH2C(OCH2CH2CH3)HCH2- -CH2C(OCH2CH2CH2CH3)HCH2- -CH2CH2-S-CH2CH2- -(CH2CH2-S)2-CH2CH2- -(CH2CH2-S)3-CH2CH2- -(CH2CH2-S)4-CH2CH2- -(CH2CH2-S)5-CH2CH2- -C(CH3)HCH2-S-C(CH3)HCH2- -(C(CH3)HCH2)2-S-C(CH3)HCH2- -(C(CH3)HCH2)3-S-C(CH3)HCH2- -(C(CH3)HCH2)4-SC(CH3)HCH2- -(C(CH3)HCH2)5-SC(CH3)HCH2- -CH2CH2CH2-S-CH2CH2CH2- -(CH2CH2CH2)2-S-CH2CH2CH2- -(CH2CH2CH2)3-S-CH2CH2CH2- -(CH2CH2CH2)4-S-CH2CH2CH2- -(CH2CH2CH2)5-S-CH2CH2CH2- -CH2C(SCH3)HCH2- -CH2C(SCH2CH3)HCH2- -CH2C(SCH2CH2CH3)HCH2- -CH2C(SCH2CH2CH2CH3)HCH2-

[0027] Among these groups, -CH2CH2-O-CH2CH2-, -(CH2CH2-O)2-CH2CH2-, -(CH2CH2-O)3-CH2CH2-, -CH2CH2CH2-O-CH2CH2CH2-, -CH2CH2-S-CH2CH2-, -(CH2CH2-S)2-CH2CH2-, and -(CH2CH2-S)3-CH2CH2- is preferred, -(CH2CH2-O)2-CH2CH2-, -(CH2CH2-O)3-CH2CH2-, -(CH2CH2-S)2-CH2CH2-, and -(CH2CH2-S)3-CH2CH2- is more preferred.

[0028] In formula (A1), X a01 , X a02 , X a03 , and X a04 are each independently O or S.

[0029] In formula (A1), R a02 The number of O and / or S contained in the alkylene group as R a04 and the number of O and / or S contained in the alkylene group is 2 or more. When the compound (A1) contains O and / or S in a specific amount or more in a specific portion, excessive weight loss of components other than the solvent when the composition is heated can be suppressed, and the dispersion of the inorganic fine particles (B) in the composition can be stabilized. R a02 The number of O and / or S contained in the alkylene group as R a04 The upper limit of the total number of O and / or S contained in the alkylene group as is not particularly limited as long as the desired effect is not impaired. R a02 The number of O and / or S contained in the alkylene group as R a04 The total number of O and / or S contained in the alkylene group as is, for example, preferably 2 or more and 10 or less, more preferably 2 or more and 8 or less, and even more preferably 2 or more and 6 or less.

[0030] Preferable specific examples of the compound (A1) include the following compounds. In the following compounds, the linking group connecting the acryloyloxy group or methacryloyloxy group with the aryloxy group, arylthio group, heteroaryloxy group, or heteroarylthio group is -CH2CH2-O-CH2CH2-, -(CH2CH2-O)2-CH2CH2-, -(CH2CH2-O)3-CH2CH2-, -CH2CH2CH2-O-CH2CH2CH2-, -CH2CH2-S-CH2CH2-, Compounds in which the formula is changed to -(CH2CH2-S)2-CH2CH2- or -(CH2CH2-S)3-CH2CH2- are also preferred as compound (A1). [ka]

[0031] [New compound] The novel compound is represented by the following formula (A1): Ra01 -X a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -R a03 ···(A1) (In formula (A1), R a01 , and R a03 are each independently a radical polymerizable group-containing group or a cationically polymerizable group-containing group, R a02 , and R a04 each independently represents an alkylene group optionally interrupted by one or more O and / or S; X a01 , X a02 , X a03 , and X a04 are each independently O or S, Ph 1 , and Ph 2 each independently represents a phenylene group optionally substituted with an alkyl group having 1 to 5 carbon atoms, R a02 The number of O and / or S contained in the alkylene group as R a04 and the number of O and / or S contained in the alkylene group as The compound represented by formula (A1) does not simultaneously have a radical polymerizable group-containing group and a cationically polymerizable group-containing group. is expressed as However, X a01 , and X a02 are both S, and the X a01 However, the above Ph 1 In Ph 1 and Ph 2 and binds to the para position relative to S, which connects X a02 But Ph 2 In Ph 1 and Ph 2 When the bond is para to S that connects a02 , and R a04is not a group represented by —CH2CH2—O—CH2CH2—. Formula (A1) is as described above.

[0032] Preferable specific examples of the novel compounds include the following compounds. In the following compounds, the linking group connecting the acryloyloxy group or methacryloyloxy group with the aryloxy group, arylthio group, heteroaryloxy group, or heteroarylthio group is -CH2CH2-O-CH2CH2-, -(CH2CH2-O)2-CH2CH2-, -(CH2CH2-O)3-CH2CH2-, -CH2CH2CH2-O-CH2CH2CH2-, -CH2CH2-S-CH2CH2-, Compounds changed to -(CH2CH2-S)2-CH2CH2- or -(CH2CH2-S)3-CH2CH2- are also preferred as novel compounds. [ka]

[0033] The method for producing the compound represented by formula (A1) is not particularly limited. A preferred method for producing the compound represented by formula (A1-a) is reacted with a compound represented by formula (A1-b) and a compound represented by formula (A1-c) in the presence of a base to obtain a compound represented by formula (A1-d): -X of the compound represented by the following formula (A1-d): a03 The terminal hydrogen atom represented by -H is R a01 and is substituted with a group represented by -X a04 The terminal hydrogen atom represented by -H is R a03 and substituting a group represented by the formula: HX a01 -Ph 1 -S-Ph 2 -X a02 -H···(A1-a) HX a03 -R a02 -Hal···(A1-b) HXa04 -R a04 -Hal···(A1-c) HX a03 -R a02 -X a01 -Ph 1 -S-Ph 2 -X a02 -R a04 -X a04 -H···(A1-d) (In formula (A1-a), formula (A1-b), formula (A1-c), and formula (A1-d), R a0 R a02 , R a04 , X a01 ~X a04 , Ph.D. 1 , and Ph 2 are the same as those in formula (A1), and Hal is a halogen atom.

[0034] The reaction of the compound represented by formula (A1-a), the compound represented by formula (A1-b), and the compound represented by formula (A1-c) in the presence of a base is usually carried out in the presence of an organic solvent. The organic solvent used in the reaction of the compound represented by formula (A1-a) with the compound represented by formula (A1-b) and the compound represented by formula (A1-c) is not particularly limited as long as it does not inhibit the progress of the reaction. Since the reaction is carried out in the presence of a base, the organic solvent is preferably an organic solvent that does not have an acidic group such as a carboxy group or a sulfonic acid group, or a hydroxyl group. The organic solvent is preferably an aprotic polar organic solvent, since it facilitates the reaction to proceed smoothly. Suitable examples of the aprotic polar organic solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, tetrahydrofuran, cyclopentyl methyl ether, acetonitrile, and hexamethylphosphoric triamide.

[0035] The compound represented by formula (A1-a) may be reacted with the compound represented by formula (A1-b) and the compound represented by formula (A1-c) simultaneously. Alternatively, the compound represented by formula (A1-a) may be reacted with the compound represented by formula (A1-b) and the compound represented by formula (A1-c) in any order. Since the intermediates and the final product can be easily purified, the compound represented by formula (A1-b) and the compound represented by formula (A1-c) are the same compound, By various well-known chromatographic techniques, such as column chromatography, When the product of the reaction of the compound represented by formula (A1-a), the compound represented by formula (A1-b), and the compound represented by formula (A1-c) is a plurality of compounds, the compound represented by formula (A1-d) may be separated and collected by various well-known chromatographic methods such as column chromatography.

[0036] The amount of organic solvent used when reacting the compound represented by formula (A1-a), the compound represented by formula (A1-b), and the compound represented by formula (A1-c) is not particularly limited. The amount of organic solvent used is preferably 0.5 to 50 times by mass, more preferably 0.7 to 20 times by mass, and even more preferably 1 to 10 times by mass, based on the total mass of the base and the raw material compounds.

[0037] The base may be any basic compound used in the so-called Williamson ether synthesis, without any particular limitation. Suitable examples of the base include sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium hydride, potassium hydride, metallic sodium, and metallic potassium.

[0038] The amount of base used in the reaction of the compound represented by formula (A1-a), the compound represented by formula (A1-b), and the compound represented by formula (A1-c) is not particularly limited as long as it allows the compound represented by formula (A1-d) to be produced in a desired amount. The amount of base used is, for example, preferably 1.6 to 20 mol, more preferably 1.8 to 10 mol, and even more preferably 2 to 6 mol, per 1 mol of the compound represented by formula (A1-1a).

[0039] The amounts of the compound represented by formula (A1-b) and the compound represented by formula (A1-c) used are not particularly limited as long as they allow the compound represented by formula (A1-d) to be produced in a desired amount. The amount of the compound represented by the base formula (A1-b) and the compound represented by the formula (A1-c) used is, for example, preferably 0.8 mol or more and 10 mol or less, more preferably 0.9 mol or more and 5 mol or less, and even more preferably 1 mol or more and 3 mol or less, relative to 1 mol of the compound represented by the formula (A1-a).

[0040] The temperature at which the compound represented by formula (A1-a), the compound represented by formula (A1-b), and the compound represented by formula (A1-c) are reacted is not particularly limited as long as a desired amount of the compound represented by formula (A1-d) can be produced. The reaction temperature is, for example, preferably 0°C or higher and 200°C or lower, more preferably 10°C or higher and 180°C or lower, and even more preferably 20°C or higher and 150°C or lower. When the reaction is carried out at a temperature higher than the boiling point of the organic solvent, the reaction may be carried out using a pressure-resistant vessel. The time for reacting the compound represented by formula (A1-a), the compound represented by formula (A1-b), and the compound represented by formula (A1-c) is not particularly limited, as long as the desired amount of the compound represented by formula (A1-1d) can be produced. The reaction time is typically preferably from 1 hour to 2 days, more preferably from 2 hours to 1 day, and more preferably from 3 hours to 18 hours.

[0041] Next, the compound represented by formula (A1-d) obtained by the above method is reacted with -X a03 The terminal hydrogen atom represented by -H is a01 and is substituted with a group represented by -X a04 The terminal hydrogen atom represented by -H is R a03The group is substituted with a group represented by the formula: -X a03 The terminal hydrogen atom represented by -H is a01 There is no particular limitation on the method for substituting the group represented by -X a03 The terminal hydrogen atom represented by -H is a01 The method of substituting with a group represented by R a01 The radical polymerizable group-containing group or the cationic polymerizable group-containing group represented by the formula (I) is appropriately selected depending on the type of the radical polymerizable group-containing group or the cationic polymerizable group-containing group represented by the formula (I).

[0042] For example, R a01 is a (meth)acryloyl group, for example, a (meth)acrylic acid halide such as (meth)acryloyl chloride can be used as the -X a03 By reacting with a group represented by -H, -X a03 The terminal hydrogen atom represented by -H can be substituted with a (meth)acryloyl group. The reaction of the compound represented by formula (A1-1c) with the (meth)acrylic acid halide is preferably carried out in an organic solvent. The type of organic solvent is not particularly limited as long as it is a solvent that does not react with the compound represented by formula (A1-1c) and the (meth)acrylic acid halide. Alternatively, the compound represented by formula (A1-1) can be obtained by condensing (meth)acrylic acid with the compound represented by formula (A1-1c) according to a well-known ester synthesis method.

[0043] R a01 is a glycidyl group, -X in the compound represented by formula (A1-1c) a03 By reacting the group represented by -H with epichlorohydrin according to the information, -X a03 The terminal hydrogen atom represented by -H can be substituted with a glycidyl group. R a01 is a vinyl group, -X in the compound represented by formula (A1-1c) a03 The group represented by -H can be directly vinylated with acetylene according to conventional methods.

[0044] -X a04The terminal hydrogen atom represented by -H is R a03 The method of substituting with a group represented by -X a03 The terminal hydrogen atom represented by -H is a01 The method for substituting the group represented by the formula (I) is the same as that for substituting the group represented by the formula (I).

[0045] The compound represented by formula (A1) can also be produced by a method comprising reacting a compound represented by the following formula (A1-a) with a compound represented by the following formula (A1-e) and a compound represented by the following formula (A1-f) in the presence of a base to obtain a compound represented by formula (A1). HX a01 -Ph 1 -S-Ph 2 -X a02 -H···(A1-a) R a01 -X a03 -R a02 -Hal···(A1-e) R a03 -X a04 -R a04 -Hal···(A1-f) (In formula (A1-a), formula (A1-e), and formula (A1-f), R a01 ~R a04 , X a01 ~X a04 , Ph.D. 1 , and Ph 2 are the same as those in formula (A1), and Hal is a halogen atom.

[0046] The reaction of the compound represented by formula (A1-a) with the compound represented by formula (A1-e) and the compound represented by formula (A1-f) in the presence of a base is carried out in the same manner as the reaction of the compound represented by formula (A1-a) with the compound represented by formula (A1-b) and the compound represented by formula (A1-c) in the presence of a base described above.

[0047] The compound represented by formula (A1) produced by the above method is purified as necessary and then blended into a composition. Purification methods include well-known methods such as chromatography (e.g., column chromatography) and recrystallization.

[0048] The photopolymerizable compound (A) may contain a photopolymerizable compound (A2) other than the compound (A1) described above, as long as the desired effect is not impaired. The mass ratio of the compound (A1) to the mass of the photopolymerizable compound (A) is preferably 50 mass% or more, more preferably 70 mass% or more, even more preferably 80 mass% or more, particularly preferably 90 mass% or more, and most preferably 100 mass%.

[0049] [Other photopolymerizable compounds (A2)] As described above, the composition may contain another photopolymerizable compound (A2) in addition to the compound (A1). When the compound (A1) has a radical polymerizable group-containing group, the other photopolymerizable compound (A2) also has a radical polymerizable group-containing group. When the compound (A1) has a cationically polymerizable group-containing group, the other photopolymerizable compound (A2) also has a cationically polymerizable group-containing group.

[0050] When the other photopolymerizable compound (A2) has a radical polymerizable group-containing group, the other photopolymerizable compound (A2) may be a monofunctional compound having one radical polymerizable group or a polyfunctional compound having two or more radical polymerizable groups, and a polyfunctional compound is preferred. As the other photopolymerizable compound (A2) having a radical polymerizable group-containing group, a compound having one or more (meth)acryloyl groups, such as a (meth)acrylate compound or a (meth)acrylamide compound, is preferred, and a (meth)acrylate compound having one or more (meth)acryloyl groups is more preferred.

[0051] Examples of the monofunctional compound having a radical polymerizable group-containing group include (meth)acrylamide, methylol (meth)acrylamide, methoxymethyl (meth)acrylamide, ethoxymethyl (meth)acrylamide, propoxymethyl (meth)acrylamide, butoxymethoxymethyl (meth)acrylamide, N-methylol (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, (meth)acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, crotonic acid, 2-acrylamido-2-methylpropanesulfonic acid, tert-butylacrylamidosulfonic acid, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylamide, acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-phenoxy-2-hydroxypropyl (meth)acrylate, 2-(meth)acryloyloxy-2-hydroxypropyl phthalate, glycerin mono(meth)acrylate, tetrahydrofurfuryl (meth)acrylate, dimethylamino (meth)acrylate, glycidyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, half (meth)acrylate of a phthalic acid derivative, etc. These monofunctional compounds can be used alone or in combination of two or more.

[0052] Examples of polyfunctional compounds having a radical polymerizable group-containing group include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, dimethyloltricyclodecane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 2,2-bis(4-(meth)acryloxydi Examples of suitable acrylic acid copolymers include polyfunctional compounds such as 2,2-bis(ethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxypolyethoxyphenyl)propane, 2-hydroxy-3-(meth)acryloyloxypropyl (meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate, phthalic acid diglycidyl ester di(meth)acrylate, glycerin triacrylate, glycerin polyglycidyl ether poly(meth)acrylate, urethane (meth)acrylate (i.e., tolylene diisocyanate), a reaction product of trimethylhexamethylene diisocyanate, hexamethylene diisocyanate, and 2-hydroxyethyl (meth)acrylate, methylenebis(meth)acrylamide, (meth)acrylamide methylene ether, and a condensation product of a polyhydric alcohol and N-methylol (meth)acrylamide, as well as triacryl formal. These polyfunctional compounds can be used alone or in combination of two or more.

[0053] Among these other photopolymerizable compounds (A2) having a radical polymerizable group-containing group, polyfunctional compounds having three or more functional groups are preferred, polyfunctional compounds having four or more functional groups are more preferred, and polyfunctional compounds having five or more functional groups are even more preferred, as they tend to increase the strength of materials formed using the composition.

[0054] The composition contains inorganic fine particles (B) described below. Depending on the composition of the composition, localization of the inorganic fine particles (B) may occur in a film formed using the composition, such that a layer rich in the inorganic fine particles (B) and a layer poor in the inorganic particles (B) are formed. From the viewpoint of suppressing such localization, it is preferable that the composition contains a compound represented by the following formula (A-2a) or the following formula (A-2b) as the photopolymerizable compound (A) having a radical polymerizable group-containing group. [ka] (MA-(OR a1 ) na1 -X-CH2)2-CH-X-(R a1 -O) na1 -MA···(A-2b) (In formula (A-2a) and formula (A-2b), each MA is independently a (meth)acryloyl group, each X is independently an oxygen atom, —NH—, or —N(CH3)—, and R a1 are each independently an ethane-1,2-diyl group, a propane-1,2-diyl group, or a propane-1,3-diyl group, and R a2 is a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, or -X-(R a1 -O) na1 -MA (wherein X is the same as above), and na1 and na2 each independently represent 0 or 1.

[0055] In formula (A-2a), R a2Examples of the alkyl group having 1 to 4 carbon atoms as the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Among these alkyl groups, a methyl group and an ethyl group are preferred.

[0056] Preferred examples of the compound represented by formula (A-2a) and the compound represented by formula (A-2b) include pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin tri(meth)acrylate, and the following compounds 1) to 32), in which MA is a (meth)acryloyl group. 1)(MA-NH-CH2)4-C 2) (MA-N(CH3)-CH2)4-C 3)(MA-O-CH2CH2CH2-O-CH2)4-C 4)(MA-O-CH2CH2-O-CH2)4-C 5)(MA-O-CH2CH2CH2-NH-CH2)4-C 6)(MA-O-CH2CH2-NH-CH2)4-C 7)(MA-O-CH2CH2CH2-N(CH3)-CH2)4-C 8)(MA-O-CH2CH2-N(CH3)-CH2)4-C 9)(MA-NH-CH2)3-C-CH2-O-CH2-C-(CH2-NH-MA)3 10)(MA-N(CH3)-CH2)3-C-CH2-O-CH2-C-(CH2-N(CH3)-MA)3 11)(MA-O-CH2CH2CH2-O-CH2)3-C-CH2-O-CH2-C-(CH2-O-CH2CH2CH2-O-MA)3 12)(MA-O-CH2CH2-O-CH2)3-C-CH2-O-CH2-C-(CH2-O-CH2CH2-O-MA)3 13)(MA-O-CH2CH2CH2-NH-CH2)3-C-CH2-O-CH2-C-(CH2-NH-CH2CH2CH2-O-MA)3 14)(MA-O-CH2CH2-NH-CH2)3-C-CH2-O-CH2-C-(CH2-NH-CH2CH2-O-MA)3 15)(MA-O-CH2CH2CH2-N(CH3)-CH2)3-C-CH2-O-CH2-C-(CH2-N(CH3)-CH2CH2CH2-O-MA)3 16)(MA-O-CH2CH2-N(CH3)-CH2)3-C-CH2-O-CH2-C-(CH2-N(CH3)-CH2CH2-O-MA)3 17)(MA-NH-CH2)2-CH-NH-MA 18)(MA-N(CH3)-CH2)2-CH-N(CH3)-MA 19)(MA-O-CH2CH2CH2-O-CH2)2-CH-O-CH2CH2CH2-O-MA 20)(MA-O-CH2CH2-O-CH2)2-CH-CO-CH2CH2-O-MA 21)(MA-O-CH2CH2CH2-NH-CH2)2-CH-NH-CH2CH2CH2-O-MA 22)(MA-O-CH2CH2-NH-CH2)2-CH2-NH-CH2CH2-O-MA 23)(MA-O-CH2CH2CH2-N(CH3)-CH2)2-CH2-N(CH3)-CH2CH2CH2-O-MA 24)(MA-O-CH2CH2-N(CH3)-CH2)2-CH2-N(CH3)-CH2CH2-O-MA 25)(MA-NH-CH2)3-C-CH2CH3 26)(MA-N(CH3)-CH2)3-C-CH2CH3 27)(MA-O-CH2CH2CH2-O-CH2)3-C-CH2CH3 28)(MA-O-CH2CH2-O-CH2)3-C-CH2CH3 29)(MA-O-CH2CH2CH2-NH-CH2)3-C-CH2CH3 30)(MA-O-CH2CH2-NH-CH2)3-C-CH2CH3 31)(MA-O-CH2CH2CH2-N(CH3)-CH2)3-C-CH2CH3 32)(MA-O-CH2CH2-N(CH3)-CH2)3-C-CH2CH3

[0057] In order to suppress localization of inorganic fine particles (B) in a material formed using the composition, the ratio of the total mass of the compound represented by formula (A-2a) and the compound represented by formula (A-2b) to the mass of the photopolymerizable compound (A) is preferably 20% by mass or more and 50% by mass or less, more preferably 30% by mass or more and 50% by mass or less, and even more preferably 40% by mass or more and 50% by mass or less.

[0058] In view of the ease of forming a high refractive index material using the composition, it is preferable that the composition contains a compound represented by the following formula (A-2c) as the other photopolymerizable compound (A2) having a radical polymerizable group-containing group: [ka] In formula (A-2c), R 1 , and R 2 are each independently a hydrogen atom or a methyl group. 3 , and R 4 are each independently an alkyl group having 1 to 5 carbon atoms; p and q are each independently 0 or 1.

[0059] R 1 , and R 2 are each independently a hydrogen atom or a methyl group. 1 , and R 2 may be different from each other or may be the same. In view of the ease of synthesis and availability of the compound represented by formula (A-2c), R 1 , and R 2 are preferably the same.

[0060] R 3 , and R 4are each independently an alkyl group having 1 to 5 carbon atoms. 3 , and R 4 may be different from each other or may be the same. In view of the ease of synthesis and availability of the compound represented by formula (A-2c), R 3 , and R 4 are preferably the same.

[0061] R 3 , and R 4 The alkyl group having 1 to 5 carbon atoms as R may be linear or branched. 3 , and R 4 Examples of the alkyl group having 1 to 5 carbon atoms as the radical include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, and a tert-pentyl group.

[0062] Specific preferred examples of the compound represented by formula (A-2c) include the following compounds: [ka]

[0063] When the composition contains a compound represented by formula (A-2c) as another photopolymerizable compound (A2) having a radical polymerizable group-containing group, the ratio of the mass of the compound represented by formula (A-2c) to the mass of the photopolymerizable compound (A) is preferably 10 mass% or more and 50 mass% or less, more preferably 30 mass% or more and 50 mass% or less.

[0064] In order to easily suppress localization of the inorganic fine particles (B) in a material formed using the composition, it is preferable that the composition contains a sulfur-containing (meth)acrylate represented by the following formula (A-2d) as the other photopolymerizable compound (A2) having a radical polymerizable group-containing group. Ar a1 -R a21 -SR a22 -O-CO-CR a23 =CH2 (A-2d) (In formula (A-2d), Ar a1 is a phenyl group optionally substituted with a halogen atom, and R a21 is a single bond or an alkylene group having 1 to 6 carbon atoms, and R a22 is an alkylene group having 1 to 6 carbon atoms, and R a23 is a hydrogen atom or a methyl group.

[0065] Ar a1 is a phenyl group which may be substituted with a halogen atom. When the phenyl group is substituted with a halogen atom, the number of halogen atoms bonded to the phenyl group is not particularly limited. The number of halogen atoms bonded to the phenyl group is preferably 1 or 2, more preferably 1. When two or more halogen atoms are bonded to the phenyl group, the multiple halogen atoms bonded to the phenyl group may consist of only halogen atoms of the same type, or may consist of two or more types of halogen atoms. Examples of halogen atoms which can be bonded to the phenyl group include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms, chlorine atoms, and bromine atoms being preferred. Ar a1 As the aryl group, an unsubstituted phenyl group is preferred.

[0066] R a21 is a single bond or an alkylene group having from 1 to 6 carbon atoms. Examples of the alkylene group having from 1 to 6 carbon atoms include a methylene group, an ethane-1,2-diyl group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. R a21 As the group, a single bond and a methylene group are preferred, and a single bond is more preferred.

[0067] R a22is an alkylene group having from 1 to 6 carbon atoms. Examples of the alkylene group having from 1 to 6 carbon atoms include a methylene group, an ethane-1,2-diyl group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. R a22 As the alkyl group, a methylene group, an ethane-1,2-diyl group, and a propane-1,3-diyl group are preferred, and an ethane-1,2-diyl group and a propane-1,3-diyl group are more preferred.

[0068] In terms of the ease of obtaining sulfur-containing (meth)acrylates and the suppression of localization of inorganic fine particles (B) in materials formed using the compositions, the use of Ar a1 is a phenyl group, and R a21 It is particularly preferred that is a single bond.

[0069] Preferred specific examples of the sulfur-containing (meth)acrylate represented by formula (A-2d) include 2-phenylthioethyl (meth)acrylate, 3-phenylthiopropyl (meth)acrylate, 2-benzylthioethyl (meth)acrylate, 3-benzylthiopropyl (meth)acrylate, 2-(2-chlorophenyl)ethyl (meth)acrylate, 2-(3-chlorophenyl)ethyl (meth)acrylate, 2-(4-chlorophenyl)ethyl (meth)acrylate, 3-(2-chlorophenyl)propyl (meth)acrylate, 3-(3-chlorophenyl)propyl (meth)acrylate, 3-(4-chlorophenyl)propyl (meth)acrylate, and 2-(2-fluorophenyl)ethyl (meth)acrylate. 2-(3-fluorophenyl)ethyl (meth)acrylate, 2-(4-fluorophenyl)ethyl (meth)acrylate, 3-(2-fluorophenyl)propyl (meth)acrylate, 3-(3-fluorophenyl)propyl (meth)acrylate, 3-(4-fluorophenyl)propyl (meth)acrylate, 2-(2-bromophenyl)ethyl (meth)acrylate, 2-(3-bromophenyl)ethyl (meth)acrylate, 2-(4-bromophenyl)ethyl (meth)acrylate, 3-(2-bromophenyl)propyl (meth)acrylate, 3-(3-bromophenyl)propyl (meth)acrylate, and 3-(4-bromophenyl)propyl (meth)acrylate.

[0070] When the composition contains a sulfur-containing (meth)acrylate represented by formula (A-2d) as another photopolymerizable compound (A2) having a radically polymerizable group-containing group, the ratio of the mass of the sulfur-containing (meth)acrylate represented by formula (A-2d) to the mass of the photopolymerizable compound (A) is preferably 40 mass% or more and 50 mass% or less.

[0071] When the compound (A1) has a cationically polymerizable group-containing group, the other photopolymerizable compound (A2) may be a monofunctional compound having one cationically polymerizable group or a polyfunctional compound having two or more cationically polymerizable groups, and a polyfunctional compound is preferred.

[0072] When the compound (A1) has a vinyloxy group-containing group as the cationically polymerizable group-containing group, the composition may contain a vinyl ether compound as another photopolymerizable compound (A2). Such a vinyl ether compound may be a monofunctional compound or a polyfunctional compound.

[0073] Specific preferred examples of the vinyl ether compound include vinyl phenyl ether, 4-vinyloxytoluene, 3-vinyloxytoluene, 2-vinyloxytoluene, 1-vinyloxy-4-chlorobenzene, 1-vinyloxy-3-chlorobenzene, 1-vinyloxy-2-chlorobenzene, 1-vinyloxy-2,3-dimethylbenzene, 1-vinyloxy-2,4-dimethylbenzene, 1-vinyloxy-2,5-dimethylbenzene, and 1-vinyloxy-2,6-dimethylbenzene. Aromatic monovinyl ethers such as methylbenzene, 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'-biphenyl, 2-vinyloxy-1,1'-biphenyl, 6-vinyloxytetralin, and 5-vinyloxytetralin Compounds: 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-divinyloxy and aromatic divinyl ether compounds such as bisphenol A divinyl ether. These vinyl ether compounds may be used in combination of two or more kinds.

[0074] When the compound (A1) has an epoxy group-containing group as the cationically polymerizable group-containing group, the composition may contain various epoxy compounds as other photopolymerizable compounds (A2). Examples of epoxy compounds include bifunctional epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD ​​type epoxy resin, naphthalene type epoxy resin, and biphenyl type epoxy resin; novolac epoxy resins such as phenol novolac type epoxy resin, brominated phenol novolac type epoxy resin, orthocresol novolac type epoxy resin, bisphenol A novolac type epoxy resin, and bisphenol AD ​​novolac type epoxy resin; cycloaliphatic epoxy resins such as epoxidized products of dicyclopentadiene type phenolic resin; aromatic epoxy resins such as epoxidized products of naphthalene type phenolic resin; glycidyl ester type epoxy resins such as dimer acid glycidyl ester and triglycidyl ester; glycidyl amine type epoxy resins such as tetraglycidylaminodiphenylmethane, triglycidyl-p-aminophenol, tetraglycidyl metaxylylenediamine, and tetraglycidyl bisaminomethylcyclohexane; triglycidyl heterocyclic epoxy resins such as phenylmethyl isocyanurate; phloroglucinol 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-[4-(2,3-epoxypropoxy)phenyl]-1-[4- Examples include trifunctional epoxy resins such as [1-[4-(2,3-epoxypropoxy)phenyl]-1-methylethyl]phenyl]ethyl]phenoxy]-2-propanol; tetrafunctional epoxy resins such as tetrahydroxyphenylethane tetraglycidyl ether, tetraglycidylbenzophenone, bisresorcinol tetraglycidyl ether, and tetraglycidoxybiphenyl; and 1,2-epoxy-4-(2-oxiranyl)cyclohexane adducts of 2,2-bis(hydroxymethyl)-1-butanol.The 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol is commercially available as EHPE-3150 (manufactured by Daicel Corporation).

[0075] Furthermore, oligomeric or polymeric polyfunctional epoxy compounds can also be preferably used. Typical examples of oligomer or polymer type polyfunctional epoxy compounds include phenol novolac type epoxy compounds, brominated phenol novolac type epoxy compounds, orthocresol novolac type epoxy compounds, xylenol novolac type epoxy compounds, naphthol novolac type epoxy compounds, bisphenol A novolac type epoxy compounds, bisphenol AD ​​novolac type epoxy compounds, epoxidized dicyclopentadiene type phenol resins, and epoxidized naphthalene type phenol resins.

[0076] Other examples of suitable epoxy compounds include polyfunctional alicyclic epoxy compounds having alicyclic epoxy groups.

[0077] Specific examples of the alicyclic epoxy compound 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, and trimethylcaprolactone-modified 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate. epoxycyclohexanecarboxylate, β-methyl-δ-valerolactone-modified 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), di(3,4-epoxycyclohexylmethyl) ether of ethylene glycol, ethylenebis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxycyclohexahydrophthalate, and di-2-ethylhexyl epoxycyclohexahydrophthalate, epoxy resins having a tricyclodecene oxide group, and compounds represented by the following formulas (a01-1) to (a01-5).

[0078] Among these specific examples of alicyclic epoxy compounds, the alicyclic epoxy compounds represented by the following formulae (a01-1) to (a01-5) are preferred because high-hardness materials can be formed using the composition.

[0079] [ka] (In formula (a01-1), Z 01 R represents a single bond or a linking group (a divalent group having one or more atoms). a01 ~R a018 are each independently a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group.

[0080] Linking group Z 01Examples of the alkyl group include divalent hydrocarbon groups, -O-, -O-CO-, -S-, -SO-, -SO2-, -CBr2-, -C(CBr3)2-, -C(CF3)2-, and -R a019 Examples include a divalent group selected from the group consisting of -O-CO- and a group in which a plurality of such groups are bonded together.

[0081] Linking group Z 01 Examples of the divalent hydrocarbon group include a linear or branched alkylene group having from 1 to 18 carbon atoms and a divalent alicyclic hydrocarbon group. Examples of the linear or branched alkylene group having from 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 cycloalkylene group (including a cycloalkylidene group) such as a 1,2-cyclopentylene group, a 1,3-cyclopentylene group, a cyclopentylidene group, a 1,2-cyclohexylene group, a 1,3-cyclohexylene group, a 1,4-cyclohexylene group, and a cyclohexylidene group.

[0082] R a019 is an alkylene group having 1 to 8 carbon atoms, and is preferably a methylene group or an ethylene group.

[0083] [ka] (In formula (a01-2), R a01 ~R a018 R is a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group. a02 and R a010 may be bonded to each other. a013 and R a016 may be bonded to each other to form a ring. a1 is either 0 or 1.)

[0084] The alicyclic epoxy compound represented by the formula (a01-2) includes m a1is 0, and is preferably a compound represented by the following formula (a01-2-1). [ka] (In formula (a01-2-1), R a01 ~R a012 R is a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group. a02 and R a010 may be bonded to each other to form a ring.

[0085] [ka] (In formula (a01-3), R a01 ~R a010 R is a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group. a02 and R a08 may be combined with each other.)

[0086] [ka] (In formula (a01-4), R a01 ~R a012 R is a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group. a02 and R a010 may be combined with each other.)

[0087] [ka] (In formula (a01-5), R a01 ~R a012 is a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group.

[0088] In formulas (a01-1) to (a01-5), R a01 ~R a018is an organic group, the organic group is not particularly limited as long as it does not impair the object of the present invention, and may be a hydrocarbon group, a group consisting of carbon atoms and halogen atoms, or a group containing heteroatoms such as halogen atoms, oxygen atoms, sulfur atoms, nitrogen atoms, and silicon atoms in addition to carbon atoms and hydrogen atoms. Examples of halogen atoms include chlorine atoms, bromine atoms, iodine atoms, and fluorine atoms.

[0089] The organic group is preferably a hydrocarbon group, a group consisting of carbon atoms, hydrogen atoms, and oxygen atoms, a halogenated hydrocarbon group, a group consisting of carbon atoms, oxygen atoms, and halogen atoms, or a group consisting of carbon atoms, hydrogen atoms, oxygen atoms, and halogen atoms. 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 to 20, more preferably 1 to 10, and particularly preferably 1 to 5.

[0090] Specific examples of the hydrocarbon group include chain alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-icosyl; vinyl, 1-propenyl, 2-n-propenyl (allyl), and 1-n-butenyl. chain alkenyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl; aryl groups such as phenyl, o-tolyl, m-tolyl, p-tolyl, α-naphthyl, β-naphthyl, biphenyl-4-yl, biphenyl-3-yl, biphenyl-2-yl, anthryl, and phenanthryl; and aralkyl groups such as benzyl, phenethyl, α-naphthylmethyl, β-naphthylmethyl, α-naphthylethyl, and β-naphthylethyl.

[0091] Specific examples of the halogenated hydrocarbon group include halogenated chain alkyl groups such as a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a bromomethyl group, a dibromomethyl group, a tribromomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, and a perfluorodecyl group; halogenated cyclohexyl groups such as a 2-chlorocyclohexyl group, a 3-chlorocyclohexyl group, a 4-chlorocyclohexyl group, a 2,4-dichlorocyclohexyl group, a 2-bromocyclohexyl group, a 3-bromocyclohexyl group, and a 4-bromocyclohexyl group; chloroalkyl groups; halogenated aryl groups such as a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2,3-dichlorophenyl group, a 2,4-dichlorophenyl group, a 2,5-dichlorophenyl group, a 2,6-dichlorophenyl group, a 3,4-dichlorophenyl group, a 3,5-dichlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group, a 4-bromophenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, and a 4-fluorophenyl group; halogenated aralkyl groups such as a 2-chlorophenylmethyl group, a 3-chlorophenylmethyl group, a 4-chlorophenylmethyl group, a 2-bromophenylmethyl group, a 3-bromophenylmethyl group, a 4-bromophenylmethyl group, a 2-fluorophenylmethyl group, a 3-fluorophenylmethyl group, and a 4-fluorophenylmethyl group.

[0092] Specific examples of the group consisting of carbon atoms, hydrogen atoms, and oxygen atoms include chain hydroxy alkyl groups such as a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxy-n-propyl group, and a 4-hydroxy-n-butyl group; halogenated cycloalkyl groups such as a 2-hydroxycyclohexyl group, a 3-hydroxycyclohexyl group, and a 4-hydroxycyclohexyl group; a 2-hydroxyphenyl group, a 3-hydroxyphenyl group, a 4-hydroxyphenyl group, a 2,3-dihydroxyphenyl group, a 2,4-dihydroxyphenyl group, a 2,5-dihydroxyphenyl group, and a 2,5-dihydroxyphenyl group. hydroxyaryl groups such as phenyl, 2,6-dihydroxyphenyl, 3,4-dihydroxyphenyl, and 3,5-dihydroxyphenyl; hydroxyaralkyl groups such as 2-hydroxyphenylmethyl, 3-hydroxyphenylmethyl, and 4-hydroxyphenylmethyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, and the like. chain alkoxy groups such as n-methyl-n-methyloxy, n-ethyl ... chain alkenyloxy groups such as an oxy group; aryloxy groups such as a phenoxy group, an o-tolyloxy group, an m-tolyloxy group, a p-tolyloxy group, an α-naphthyloxy group, a β-naphthyloxy group, a biphenyl-4-yloxy group, a biphenyl-3-yloxy group, a biphenyl-2-yloxy group, an anthryloxy group, and a phenanthryloxy group; aralkyloxy groups such as a benzyloxy group, a phenethyloxy group, an α-naphthylmethyloxy group, a β-naphthylmethyloxy group, an α-naphthylethyloxy group, and a β-naphthylethyloxy group;Alkoxyalkyl groups such as a methoxymethyl group, an ethoxymethyl group, an n-propoxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-n-propoxyethyl group, a 3-methoxy-n-propyl group, a 3-ethoxy-n-propyl group, a 3-n-propoxy-n-propyl group, a 4-methoxy-n-butyl group, a 4-ethoxy-n-butyl group, and a 4-n-propoxy-n-butyl group; a methoxymethoxy group, an ethoxymethoxy group, an n-propoxymethoxy group, a 2-methoxyethoxy group, a 2-ethoxyethoxy group, and a 2-n-propoxyethoxy group. alkoxyalkoxy groups such as a 3-methoxy-n-propoxy group, a 3-ethoxy-n-propoxy group, a 3-n-propoxy-n-propoxy group, a 4-methoxy-n-butyloxy group, a 4-ethoxy-n-butyloxy group, and a 4-n-propoxy-n-butyloxy group; alkoxyaryl groups such as a 2-methoxyphenyl group, a 3-methoxyphenyl group, and a 4-methoxyphenyl group; alkoxyaryloxy groups such as a 2-methoxyphenoxy group, a 3-methoxyphenoxy group, and a 4-methoxyphenoxy group; a formyl group, an acetyl group, a propionyl group, aliphatic acyl groups such as benzoyl, butanoyl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, and decanoyl groups; aromatic acyl groups such as benzoyl, α-naphthoyl, and β-naphthoyl groups; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, n-pentyloxycarbonyl, n-hexylcarbonyl, n-heptyloxycarbonyl, n-octyloxycarbonyl, n-nonyloxycarbonyl, and n-decyloxycarbonyl groups; chain alkyloxycarbonyl groups such as an alkyloxy group; aryloxycarbonyl groups such as a phenoxycarbonyl group, an α-naphthoxycarbonyl group, and a β-naphthoxycarbonyl group; aliphatic acyloxy groups such as a formyloxy group, an acetyloxy group, a propionyloxy group, a butanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a heptanoyloxy group, an octanoyloxy group, a nonanoyloxy group, and a decanoyloxy group; aromatic acyloxy groups such as a benzoyloxy group, an α-naphthoyloxy group, and a β-naphthoyloxy group;

[0093] R a01 ~R a018 are each independently preferably a group 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. In particular, the composition is easily used to form a material having excellent mechanical properties. Therefore, R a01 ~R a018 More preferably, all of are hydrogen atoms.

[0094] In formulas (a01-2) to (a01-5), R a01 ~R a018 is R in formula (a01-1) a01 ~R a018 In formula (a01-2) and formula (a01-4), R a02 and R a010 When these are bonded to each other, in formula (a01-2), R a013 and R a016 are bonded to each other, and in formula (a01-3), R a02 and R a08 Examples of the divalent group formed when these groups bond to each other include -CH2- and -C(CH3)2-.

[0095] Among the alicyclic epoxy compounds represented by formula (a01-1), specific examples of suitable compounds include alicyclic epoxy compounds represented by the following formulae (a01-1a), (a01-1a), and (a01-1c), 2,2-bis(3,4-epoxycyclohexane-1-yl)propane [=2,2-bis(3,4-epoxycyclohexyl)propane], etc. [ka]

[0096] Among the alicyclic epoxy compounds represented by formula (a01-2), specific examples of suitable compounds include alicyclic epoxy compounds represented by the following formulae (a01-2a) and (a01-2b). [ka]

[0097] Among the alicyclic epoxy compounds represented by formula (a01-3), specific examples of suitable compounds include S-spiro[3-oxatricyclo[3.2.1.0 2,4 ]octane-6,2'-oxirane] and the like.

[0098] Among the alicyclic epoxy compounds represented by formula (a01-4), specific examples of suitable compounds include 4-vinylcyclohexene dioxide, dipentene dioxide, limonene dioxide, 1-methyl-4-(3-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane, and the like.

[0099] Among the alicyclic epoxy compounds represented by formula (a01-5), a specific example of a suitable compound is 1,2,5,6-diepoxycyclooctane.

[0100] Furthermore, a compound represented by the following formula (a1-I) can be suitably used as the epoxy compound. [ka] (In formula (a1-I), X a1 , X a2 , and X a3 are each independently 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 contained in

[0101] The compound represented by the above formula (a1-I) is preferably a compound represented by the following formula (a1-II): [ka] (In formula (a1-II), R a20 ~R a22represents a linear, branched, or cyclic alkylene group, an arylene group, -O-, -C(=O)-, -NH-, or a group consisting of a combination thereof, and may be the same or different. 1 ~E 3 is at least one substituent selected from the group consisting of an epoxy group, an oxetanyl group, an ethylenically unsaturated group, an alkoxysilyl group, an isocyanate group, a blocked isocyanate group, a thiol group, a carboxy group, a hydroxyl group, and a succinic anhydride group, or a hydrogen atom, provided that E 1 , E 2 , and E 3 The total number of epoxy groups contained in

[0102] In formula (a1-II), R a20 and E 1 , R a21 and E 2 , and R a22 and E 3 Preferably, at least two of the groups represented by the formula (a1-IIa) are each a group represented by the following formula (a1-IIa), and more preferably, all of the groups are each a group represented by the following formula (a1-IIa). Preferably, multiple groups represented by formula (a1-IIa) bonded to one compound are the same group. -LC a (a1-IIa) In formula (a1-IIa), L represents a linear, branched, or cyclic alkylene group, an arylene group, —O—, —C(═O)—, —NH—, or a group formed by a combination thereof; a is an oxiranyl group (epoxy group). In formula (a1-IIa), L and C a may be bonded to form a cyclic structure.)

[0103] In formula (a1-IIa), the linear, branched, or cyclic alkylene group represented by L is preferably an alkylene group having from 1 to 10 carbon atoms, and the arylene group represented by L is preferably an arylene group having from 5 to 10 carbon atoms. In formula (a1-IIa), L is preferably a linear alkylene group having from 1 to 3 carbon atoms, a phenylene group, -O-, -C(=O)-, -NH-, or a group formed by a combination thereof, and is preferably at least one of a linear alkylene group having from 1 to 3 carbon atoms, such as a methylene group, and a phenylene group, or a group formed by a combination of any of these with at least one of -O-, -C(=O)-, and NH-.

[0104] In formula (a1-IIa), L and C a Examples of the case where a branched alkylene group and an epoxy group are bonded to form a cyclic structure (a structure having an alicyclic epoxy group) include organic groups represented by the following formulas (a1-IIb) to (a1-IId). [ka] (In formula (a1-IIb), R a23 is a hydrogen atom or a methyl group.

[0105] Examples of the compound represented by formula (a1-II) include, but are not limited to, epoxy compounds having an oxiranyl group or an alicyclic epoxy group. [ka]

[0106] [ka]

[0107] Furthermore, a siloxane compound having two or more glycidyl groups or alicyclic epoxy groups in the molecule (hereinafter also simply referred to as "siloxane compound") can be suitably used as the epoxy compound.

[0108] The siloxane compound is a compound having a siloxane skeleton composed of siloxane bonds (Si—O—Si) and two or more glycidyl groups or alicyclic epoxy groups in the molecule.

[0109] Examples of the siloxane skeleton in the siloxane compound include a cyclic siloxane skeleton and a cage-type or ladder-type polysilsesquioxane skeleton.

[0110] Of the siloxane compounds, compounds having a cyclic siloxane skeleton represented by the following formula (a1-III) (hereinafter, sometimes referred to as "cyclic siloxane") are preferred. [ka]

[0111] In formula (a1-III), R a24 , and R a25 represents a monovalent group or alkyl group containing an epoxy group, provided that x1 R in the compound represented by formula (a1-III) a24 and x1 R a25 At least two of the groups represented by formula (a1-III) are monovalent groups containing an epoxy group. In addition, x1 in formula (a1-III) represents an integer of 3 or more. a24 , R a25 may be the same or different. a24 may be the same or different. a25 may be the same or different. Examples of the alkyl group include linear or branched alkyl groups having 1 to 18 carbon atoms (preferably 1 to 6 carbon atoms, particularly preferably 1 to 3 carbon atoms), such as a methyl group, an ethyl group, a propyl group, and an isopropyl group.

[0112] In formula (a1-III), x1 represents an integer of 3 or more, and preferably an integer of 3 or more and 6 or less in terms of excellent crosslinking reactivity when forming a functional material using the composition. The number of epoxy groups contained in the siloxane compound molecule is two or more, and from the viewpoint of excellent crosslinking reactivity when a functional material is formed using the composition, it is preferably two to six, and particularly preferably two to four.

[0113] The monovalent group containing an epoxy group includes an alicyclic epoxy group and -D A -OR a26 A glycidyl ether group [D A represents an alkylene group, and R a26 represents a glycidyl group] is preferred, an alicyclic epoxy group is more preferred, and an alicyclic epoxy group represented by the following formula (a1-IIIa) or the following formula (a1-IIIb) is even more preferred. A 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. [ka] (In the above formula (a1-IIIa) and formula (a1-IIIb), D 1 and D 2 each independently represents an alkylene group, and ms represents an integer of 0 or more and 2 or less.

[0114] In addition to the siloxane compound represented by Formula (a1-III), the composition may contain, as the epoxy compound, a compound having a siloxane skeleton, such as an alicyclic epoxy group-containing cyclic siloxane, an alicyclic epoxy group-containing silicone resin described in JP-A-2008-248169, and an organopolysilsesquioxane resin having at least two epoxy functional groups per molecule described in JP-A-2008-19422.

[0115] More specifically, the siloxane compound may be a cyclic siloxane having two or more glycidyl groups in the molecule, as represented by the following formula: Furthermore, as the siloxane compound, for example, commercially available products such as "X-40-2670," "X-40-2701," "X-40-2728," "X-40-2738," and "X-40-2740" (all manufactured by Shin-Etsu Chemical Co., Ltd.) may be used.

[0116] [ka]

[0117] [ka]

[0118] In terms of facilitating the formation of a high refractive index material using the composition, the composition preferably contains a compound represented by the following formula (A-2e) as the other photopolymerizable compound (A2). [ka] (In formula (A-2e), R A1 , R A2 , and R A3 are each independently an organic group, and R A1 , as an organic group, R A2 organic groups as R A3 At least two of the organic groups have a radical polymerizable group-containing group or a cation polymerizable group-containing group.

[0119] Preferred examples of the compound represented by formula (A-2e) include compounds represented by the following formula (A-2e-a). [ka]

[0120] In formula (A-2e-a), R A01represents an optionally substituted quinolinyl group, an optionally substituted isoquinolinyl group, or an optionally substituted 2-substituted benzothiazolyl group. 2-substituted benzothiazolyl group has -SR at the 2-position A0 R A0 is a hydrogen atom, a radical polymerizable group-containing group, or a cationically polymerizable group-containing group. R A02 , and R A03 are both aromatic ring-containing groups having a radical polymerizable group-containing group, or are both aromatic ring-containing groups having a cationically polymerizable group-containing group. The -NH- group attached to the triazine ring is R A02 , and R A03 It bonds to the aromatic ring in the center.

[0121] The quinolinyl group which may have a substituent, the isoquinolinyl group which may have a substituent, and the 2-substituted benzothiazolyl group which may have a substituent all have high polarizability and small volume as functional groups. A01 is an optionally substituted quinolinyl group, an optionally substituted isoquinolinyl group, or an optionally substituted 2-substituted benzothiazolyl group, which is thought to contribute to the high refractive index of a material formed using the composition.

[0122] R A01 The quinolinyl group as may be any of a quinolin-2-yl group, a quinolin-3-yl group, a quinolin-4-yl group, a quinolin-5-yl group, a quinolin-6-yl group, a quinolin-7-yl group, and a quinolin-8-yl group. Among these groups, a quinolin-3-yl group and a quinolin-4-yl group are preferred because raw materials for the compound represented by formula (A2e-a) are easily available and the compound represented by formula (A2e-a) is easily synthesized.

[0123] R A01The isoquinolinyl group as may be any of isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, and isoquinolin-8-yl.

[0124] R A01 The substituents that the quinolinyl group and isoquinolinyl group may have are not particularly limited as long as the desired effects are not impaired. Examples of the substituents include halogen atoms, hydroxyl groups, mercapto groups, cyano groups, nitro groups, and monovalent organic groups. Examples of the halogen atom as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the monovalent organic group include an alkyl group, an alkoxy group, an alkoxyalkyl group, an aliphatic acyl group, an aliphatic acyloxy group, an alkoxycarbonyl group, an alkylthio group, and an aliphatic acylthio group. Furthermore, radically polymerizable group-containing groups and cationically polymerizable group-containing groups, which will be described later, are also preferred as monovalent organic groups.

[0125] The number of carbon atoms of the monovalent organic group as a substituent is not particularly limited as long as the desired effect is not impaired. The number of carbon atoms of the monovalent organic group as a substituent is, for example, preferably 1 to 20, more preferably 1 to 12, and even more preferably 1 to 8. For alkoxyalkyl groups, aliphatic acyl groups, aliphatic acyloxy groups, alkoxycarbonyl groups, alkoxyalkylthio groups, and aliphatic acylthio groups, the lower limit of the number of carbon atoms is 2.

[0126] Preferred specific examples of the alkyl group as the substituent include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group.

[0127] Specific preferred examples of the alkoxy group as the substituent include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, and an n-octyloxy group.

[0128] Preferred specific examples of the alkoxyalkyl group as the substituent include a methoxymethyl group, an ethoxymethyl group, an n-propyloxymethyl group, an n-butyloxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-n-propyloxyethyl group, a 2-n-butyloxyethyl group, a 3-methoxy-n-propyloxy group, a 3-ethoxy-n-propyloxy group, a 3-n-propyloxy-n-propyloxy group, a 3-n-butyloxy-n-propyloxy group, a 4-methoxy-n-butyloxy group, a 4-ethoxy-n-butyloxy group, a 4-n-propyloxy-n-butyloxy group, and a 4-n-butyloxy-n-butyloxy group.

[0129] Preferred specific examples of the aliphatic acyl group as the substituent include an acetyl group, a propionyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, and an octanoyl group.

[0130] Preferred specific examples of the aliphatic acyloxy group as the substituent include an acetoxy group, a propionyloxy group, a butanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a heptanoyloxy group, and an octanoyloxy group.

[0131] Preferred specific examples of the alkoxycarbonyl group as a substituent include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, a sec-butyloxycarbonyl group, a tert-butyloxycarbonyl group, an n-pentyloxycarbonyl group, an n-hexyloxycarbonyl group, an n-heptyloxycarbonyl group, and an n-octyloxycarbonyl group.

[0132] Specific preferred examples of the alkylthio group as the substituent include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, an n-pentylthio group, an n-hexylthio group, an n-heptylthio group, and an n-octylthio group.

[0133] Specific preferred examples of the aliphatic acylthio group as the substituent include an acetylthio group, a propionylthio group, a butanoylthio group, a pentanoylthio group, a hexanoylthio group, a heptanoylthio group, and an octanoylthio group.

[0134] When the quinolinyl group and the isoquinolinyl group have a substituent, the number of the substituent is not particularly limited as long as the desired effect is not impaired. When the quinolinyl group and the isoquinolinyl group have a substituent, the number of the substituent is preferably 1 to 4, more preferably 1 or 2, and particularly preferably 1. When the quinolinyl group and the isoquinolinyl group have a plurality of substituents, the plurality of substituents may be different from each other.

[0135] R A01 The 2-substituted benzothiazolyl group as A0 R A01 The 2-substituted benzothiazolyl group as the 2-substituted benzothiazolyl group may have, at any position other than 2, -SR A0 R may have other substituents in addition to the group represented by A0is a hydrogen atom, a radical polymerizable group-containing group, or a cationically polymerizable group-containing group. The radical polymerizable group-containing group and the cationically polymerizable group-containing group will be described later.

[0136] Preferred examples of the 2-substituted benzothiazolyl group include the following groups: [ka]

[0137] R A01 The substituents which the 2-substituted benzothiazolyl group as defined above may have are the same as the substituents which the quinolinyl group and the isoquinolinyl group may have. When the 2-substituted benzothiazolyl group has a substituent, the number of the substituents is not particularly limited as long as the desired effect is not impaired. When the 2-substituted benzothiazolyl group has a substituent, the number of the substituents is preferably 1 or 2, and more preferably 1. When the 2-substituted benzothiazolyl group has multiple substituents, the multiple substituents may be different from each other.

[0138] R A02 , and R A03 are both aromatic ring-containing groups having a radical polymerizable group-containing group, or are both aromatic ring-containing groups having a cationically polymerizable group-containing group. The -NH- group bonded to the triazine ring is R A02 , and R A03 It bonds to the aromatic ring in the center. R A02 , and R A03 The bonding position of the radical polymerizable group-containing group or the cationically polymerizable group-containing group in the aromatic ring-containing group is not particularly limited.

[0139] R A02 the number of radical polymerizable group-containing groups or cation polymerizable group-containing groups in the aromatic ring-containing group as R A03 The number of radical polymerizable group-containing groups or cation polymerizable group-containing groups in the aromatic ring-containing group as R A02the number of radical polymerizable group-containing groups or cation polymerizable group-containing groups in the aromatic ring-containing group as R A03 The number of radically polymerizable group-containing groups or cationically polymerizable group-containing groups in the aromatic ring-containing group as is preferably an integer of 1 or more and 3 or less, more preferably 1 or 2, and particularly preferably 1.

[0140] R A02 , and R A03 The aromatic ring-containing group represented by R may contain only one monocyclic aromatic ring or one fused aromatic ring, or may contain two or more monocyclic aromatic rings and / or fused aromatic rings. A02 , and R A03 When the aromatic ring-containing group as (I) contains two or more monocyclic aromatic rings and / or fused aromatic rings, the type of linking group linking the monocyclic aromatic rings, the fused aromatic rings, or the monocyclic aromatic ring and the fused aromatic ring is not particularly limited. The linking group may be a divalent linking group or a trivalent or higher linking group, with a divalent linking group being preferred.

[0141] Examples of the divalent linking group include a divalent aliphatic hydrocarbon group, a divalent halogenated aliphatic hydrocarbon group, -CONH-, -NH-, -N=N-, -CH=N-, -COO-, -O-, -CO-, -SO-, -SO2-, -S-, and -SS-, and combinations of two or more thereof.

[0142] In addition, the divalent linking group is -CR a001 R a002 A group represented by - is also preferred. R a001 and R a002 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a halogenated alkyl group having 1 to 4 carbon atoms. a001 and R a002 may be bonded to each other to form a ring. a001 R a002Specific examples of the group represented by - include a methylene group, an ethane-1,1-diyl group, a propane-2,2-diyl group, a butane-2,2-diyl group, a 1,1,1,3,3,3-hexafluoropropane-2,2-diyl group, a cyclopentylidene group, a cyclohexylidene group, and a cycloheptylidene group.

[0143] R A02 , and R A03 The aromatic ring-containing group as has a radical polymerizable group-containing group or a cationically polymerizable group-containing group. The radical polymerizable group-containing group and the cationically polymerizable group-containing group are as described above.

[0144] Suitable examples of the radically polymerizable group-containing group include groups represented by the following formula (AI) or (A-II), which do not fall under the category of vinyloxy group-containing groups. -(A 01 ) na -R 01 ···(AI) -(A 01 ) na -R 02 -A 02 -R 01 (A-II)

[0145] In formula (AI) and formula (A-II), R 01 is an alkenyl group having 2 to 10 carbon atoms. 02 is an alkylene group having from 1 to 10 carbon atoms. A 01 is —O—, —S—, —CO—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —CO—NH—, —NH—CO—, or —NH—. A 02 is —O—, —S—, —CO—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —CO—NH—, —NH—CO—, or —NH—. na is 0 or 1.

[0146] Specific examples of suitable radical polymerizable group-containing groups include: -OR03 、 -S-R 03 、 -O-CH2CH2-O-R 03 、 -O-CH2CH2CH2-O-R 03 、 -O-CH2CH2CH2CH2-O-R 03 、 -CO-O-CH2CH2-O-R 03 、 -CO-O-CH2CH2CH2-O-R 03 、 -CO-O-CH2CH2CH2CH2-O-R 03 、 -O-CH2CH2-NH-R 03 、 -O-CH2CH2CH2-NH-R 03 、 -O-CH2CH2CH2CH2-NH-R 03 、 -CO-O-CH2CH2-NH-R 03 、 -CO-O-CH2CH2CH2-NH-R 03 、 -CO-O-CH2CH2CH2CH2-R 03 、 -NH-R 03 、 -NH-CH2CH2-O-R 03 、 -NH-CH2CH2CH2-O-R 03 、 -NH-CH2CH2CH2CH2-O-R 03 、 -CO-NH-CH2CH2-O-R 03 、 -CO-NH-CH2CH2CH2-O-R 03 、 -CO-NH-CH2CH2CH2CH2-O-R 03 、 -NH-CH2CH2-NH-R 03 、 -NH-CH2CH2CH2-NH-R 03 、 -NH-CH2CH2CH2CH2-NH-R 03 , -CO-NH-CH2CH2-NH-R 03 , -CO-NH-CH2CH2CH2-NH-R 03 , and -CO-NH-CH2CH2CH2CH2-NH-R 03 In these groups, R 03 is an allyl group or a (meth)acryloyl group.

[0147] Suitable examples of the cationically polymerizable group-containing group include a vinyloxy group and groups represented by the following formulae (A3) to (A8). -(A 01 ) na -R 04 ···(A3) -(A 01 ) na -R 02 -R 05 ···(A4) -(A 01 ) na -R 02 -(CO) nb -A 03 -R 04 ···(A5) -(A 01 ) na -R 02 -(CO) nb -A 03 -R 07 -R 05 ···(A6) -(A 01 ) na -R 02 -OR 06 (A7) -(A 01 ) na -R 02 -(CO) nb -A 03 -R 07 -OR 06 ···(A8)

[0148] In formulas (A3) to (A8), R02 is an alkylene group having 1 to 10 carbon atoms. 04 R is an epoxyalkyl group having 2 to 20 carbon atoms, or an alicyclic epoxy group having 3 to 20 carbon atoms. 05 R is an alicyclic epoxy group having 3 to 20 carbon atoms. 06 is a vinyl group. 07 is an alkylene group having from 1 to 10 carbon atoms. A 01 is —O—, —S—, —CO—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —CO—NH—, —NH—CO—, or —NH—. A 03 is —O— or —NH—. nb is 0 or 1.

[0149] Specific examples of suitable groups containing a cationically polymerizable group include: -R 08 , -O-CH2CH2-R 08 , -O-CH2CH2CH2-R 08 , -O-CH2CH2CH2CH2-R 08 , -CO-O-CH2CH2-R 08 , -CO-O-CH2CH2CH2-R 08 , -CO-O-CH2CH2CH2CH2-R 08 , -NH-CH2CH2-R 08 , -NH-CH2CH2CH2-R 08 , -NH-CH2CH2CH2CH2-R 08 , -CO-NH-CH2CH2-R 08 , -CO-NH-CH2CH2CH2-R 08 , and -CO-NH-CH2CH2CH2CH2-R 08 In these groups, R08 is a vinyloxy group, a glycidyloxy group, a glycidylthio group, an epoxycyclopentyl group, an epoxycyclohexyl group, or an epoxycycloheptyl group.

[0150] R A02 , and R A03 When the aromatic ring-containing group as R A02 , and R A03 Suitable examples of include groups of the following formula: In the following formula, PG is a radical polymerizable group-containing group or a cationically polymerizable group-containing group. [ka]

[0151] Specific examples of suitable compounds represented by formula (A-2e) include compounds of the following formula: A is a group selected from the group consisting of a (meth)acryloyloxy group, a (meth)acryloylthio group, a 3-(meth)acryloyloxy-2-hydroxy-n-propyloxycarbonyl group, and a glycidyloxy group.

[0152] [ka]

[0153] [ka]

[0154] [ka]

[0155] The method for producing the compound represented by formula (A-2e-a) is not particularly limited. Typically, a cyanuric halide such as cyanuric chloride is reacted with R A01 -NH2, R A02 -NH2 and R A03The compound can be produced by reacting the aromatic amine represented by —NH with the cyanuric halide. These multiple amines may be reacted with the cyanuric halide simultaneously or sequentially, preferably sequentially.

[0156] Furthermore, R in formula (A-2e-a) A02 , and R A03 can also be produced by reacting an aromatic amine having a functional group such as a hydroxyl group, a mercapto group, a carboxyl group, or an amino group with a cyanuric halide, and then reacting these functional groups with a compound that provides a radically polymerizable group-containing group or a cationically polymerizable group-containing group. Examples of compounds that provide a radically polymerizable group-containing group or a cationically polymerizable group-containing group include compounds having a polymerizable group such as (meth)acrylic acid, (meth)acrylic acid halides, halogenated olefins, epichlorohydrin, and glycidyl (meth)acrylate. As the reaction between a functional group such as a hydroxyl group, a mercapto group, a carboxy group, or an amino group and a compound having a polymerizable group, well-known reactions that produce an ether bond, a carboxylic acid ester bond, a carboxylic acid amide bond, and a thioether bond can be used.

[0157] The reaction for forming the radical polymerizable group-containing group or the cationically polymerizable group-containing group may be a multi-step reaction. For example, a cyanuric halide is reacted with an aromatic amine having a phenolic hydroxyl group, and then the phenolic hydroxyl group is reacted with epichlorohydrin to be glycidylated, and then the glycidyl group is reacted with acrylic acid, thereby introducing a radical polymerizable group-containing group represented by the following formula onto the aromatic ring. -O-CH2-CHOH-CH2-O-CO-CH=CH2 The above reaction is an example, and the radical polymerizable group-containing group or the cationically polymerizable group-containing group can be formed by carrying out a combination of various reactions.

[0158] The compound represented by formula (A-2e-a) is usually synthesized in an organic solvent. Such an organic solvent is not particularly limited as long as it is an inert solvent that does not react with cyanuric halide, aromatic amine, radical polymerizable group, cationic polymerizable group, etc. As the solvent, organic solvents exemplified as specific examples of the solvent (S) described later can be used. In producing the compound represented by formula (A-2e-a), a cyanuric halide and R A01 -NH2, R A02 -NH2 and R A03 The temperature at which the reaction with aromatic amines such as the aromatic amine represented by -NH2 is carried out is not particularly limited. Typically, the reaction temperature is preferably 0°C or higher and 150°C or lower.

[0159] Other preferred examples of the compound represented by formula (A-2e) include compounds represented by the following formula (A-2e-b). [ka]

[0160] In formula (A-2e-b), R A11 , R A12 , and R A13 are each an aromatic ring-containing group. R A12 , and R A13 At least one of the above is a group represented by the following formula (A-2e-b1). [ka] The -NH- groups bonded to the triazine ring are each R A11 , R A12 , and R A13 It bonds to the aromatic ring in the center. In formula (A-2e-b1), R a11 and R a12 are each independently an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom. nA1 and nA2 each independently represent an integer of 0 or more and 4 or less. Ra13 and R a14 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, or a phenyl group. R a13 and R a14 may be bonded to each other to form a ring. R A14 is a radical polymerizable group-containing group or a cationically polymerizable group-containing group. R A12 , and R A13 are both groups represented by formula (A-2e-b1), R A12 , and R A13 both have a radical polymerizable group-containing group, or both have a cationically polymerizable group-containing group.

[0161] As described above, in formula (A-2e-b), R A11 , R A12 , and R A13 In formula (A-2e-b), the —NH— groups bonded to the triazine ring are each represented by R A11 , R A12 , and R A13 It bonds to the aromatic ring in the center. When the aromatic ring-containing group is a group other than the group represented by formula (A-2e-b1), the aromatic ring-containing group is not particularly limited as long as it satisfies the above-mentioned predetermined requirements.

[0162] The aromatic ring-containing group other than the group represented by formula (A-2e-b1) may contain only one monocyclic aromatic ring or one fused aromatic ring, or may contain two or more monocyclic aromatic rings and / or fused aromatic rings. When the aromatic ring-containing group contains two or more monocyclic aromatic rings and / or fused aromatic rings, the type of linking group linking the monocyclic aromatic rings, the fused aromatic rings, or the monocyclic aromatic ring and the fused aromatic ring is not particularly limited. The linking group may be a divalent linking group or a trivalent or higher linking group, with a divalent linking group being preferred.

[0163] Examples of the divalent linking group include a divalent aliphatic hydrocarbon group, a divalent halogenated aliphatic hydrocarbon group, -CONH-, -NH-, -N=N-, -CH=N-, -COO-, -O-, -CO-, -SO-, -SO2-, -S-, and -SS-, and combinations of two or more thereof.

[0164] Preferred examples of the aromatic ring-containing group include an optionally substituted quinolinyl group, an optionally substituted isoquinolinyl group, and an optionally substituted 2-substituted benzothiazolyl group. These groups are represented by R A01 This is similar to the optionally substituted quinolinyl group, the optionally substituted isoquinolinyl group, and the optionally substituted 2-substituted benzothiazolyl group described above.

[0165] Other preferred examples of the aromatic ring-containing group include a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a biphenylyl group which may have a substituent, a phenylthiophenyl group which may have a substituent, a phenoxyphenyl group which may have a substituent, a phenylsulfonylphenyl group which may have a substituent, a benzothiazolyl group which may have a substituent, a benzoxazolyl group which may have a substituent, and a terphenyl group which may have a substituent. When these groups have a substituent, the substituent is the same as the substituent that may be substituted by a quinolinyl group or an isoquinolinyl group. When these groups have multiple substituents, the multiple substituents may be different from each other.

[0166] Specific preferred examples of the phenyl group which may have a substituent include a phenyl group, a 4-cyanophenyl group, a 3-cyanophenyl group, a 2-cyanophenyl group, a 2,3-dicyanophenyl group, a 2,4-dicyanophenyl group, a 2,5-dicyanophenyl group, a 2,6-dicyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, a 4-nitrophenyl group, a 3-nitrophenyl group, a 2-nitrophenyl group, a 4-chlorophenyl group, a 3-chlorophenyl group, a 2-chlorophenyl group, a 4-bromophenyl group, a 3-bromophenyl group, a 2-bromophenyl group, a 4-iodophenyl group, a 3-iodophenyl group, a 2-iodophenyl group, a 4-methoxyphenyl group, a 3-methoxyphenyl group, a 2-methoxyphenyl group, a 4-methylphenyl group, a 3-methylphenyl group, and a 2-methylphenyl group.

[0167] Specific preferred examples of the naphthyl group which may have a substituent include a naphthalen-1-yl group and a naphthalen-2-yl group.

[0168] Suitable examples of the biphenylyl group which may have a substituent include a 4-phenylphenyl group, a 3-phenylphenyl group, a 2-phenylphenyl group, a 4-(4-nitrophenyl)phenyl group, a 3-(4-nitrophenyl)phenyl group, a 2-(4-nitrophenyl)phenyl group, a 4-(4-cyanophenyl)phenyl group, a 3-(4-cyanophenyl)phenyl group, and a 2-(4-cyanophenyl)phenyl group.

[0169] Specific preferred examples of the optionally substituted phenylthiophenyl group include a 4-phenylthiophenyl group, a 3-phenylthiophenyl group, and a 2-phenylthiophenyl group.

[0170] Specific preferred examples of the phenoxyphenyl group which may have a substituent include a 4-phenoxyphenyl group, a 3-phenoxyphenyl group, and a 2-phenoxyphenyl group.

[0171] Specific preferred examples of the optionally substituted phenylsulfonylphenyl group include a 4-phenylsulfonylphenyl group, a 3-phenylsulfonylphenyl group, and a 2-phenylsulfonylphenyl group.

[0172] Specific preferred examples of the optionally substituted benzothiazolyl group include a benzothiazol-2-yl group, a benzothiazol-4-yl group, a benzothiazol-5-yl group, a benzothiazol-6-yl group, and a benzothiazol-7-yl group.

[0173] Specific preferred examples of the optionally substituted benzoxazolyl group include a benzoxazol-2-yl group, a benzoxazol-4-yl group, a benzoxazol-5-yl group, a benzoxazol-6-yl group, and a benzoxazol-7-yl group.

[0174] Suitable examples of the terphenyl group which may have a substituent include a 4-(4-phenylphenyl)phenyl group, a 3-(4-phenylphenyl)phenyl group, a 2-(4-phenylphenyl)phenyl group, a 4-(3-phenylphenyl)phenyl group, a 3-(3-phenylphenyl)phenyl group, a 2-(3-phenylphenyl)phenyl group, a 4-(2-phenylphenyl)phenyl group, a 3-(2-phenylphenyl)phenyl group, and a 2-(2-phenylphenyl)phenyl group.

[0175] As described above, the aromatic ring-containing group other than the group represented by formula (A-2e-b1) may have a radically polymerizable group-containing group or a cationically polymerizable group-containing group as a substituent. The bonding position of the radical polymerizable group-containing group or the cationically polymerizable group-containing group in the aromatic ring-containing group is not particularly limited.

[0176] The number of radically polymerizable group-containing groups or cationically polymerizable group-containing groups in the aromatic ring-containing group is not particularly limited. The number of radically polymerizable group-containing groups or cationically polymerizable group-containing groups in the aromatic ring-containing group is preferably an integer of 1 to 3, more preferably 1 or 2, and particularly preferably 1.

[0177] When the aromatic ring-containing group has one radically polymerizable group-containing group or one cationically polymerizable group-containing group, suitable examples of such a group include groups of the following formula: In the following formula, PG is a radically polymerizable group-containing group or a cationically polymerizable group-containing group. [ka]

[0178] In formula (A-2e-b), R A12 , and R A13 At least one of the formulas is (A-2e-b1): [ka] It is a group represented by the following formula: In formula (A-2e-b1), R a11 and R a12 are each independently an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom. nA1 and nA2 each independently represent an integer of 0 or more and 4 or less. R a13 and R a14 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, or a phenyl group. R a13 and R a14 may be bonded to each other to form a ring. R A14 is a radical polymerizable group-containing group or a cationically polymerizable group-containing group. R A12 , and R A13 are both groups represented by formula (A-2e-b1), R A12 , and R A13 both have a radical polymerizable group-containing group, or both have a cationically polymerizable group-containing group.

[0179] R a11 , and R a12Examples of the alkyl group having 1 to 4 carbon atoms as the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. R a11 , and R a12 Examples of the alkoxy group having 1 to 4 carbon atoms as the alkoxy group include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, and a tert-butyloxy group. R a11 , and R a12 Examples of the halogen atom as the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0180] R a13 , and R a14 Specific examples of alkyl groups having 1 to 4 carbon atoms as R a11 , and R a12 The specific examples are the same as those of the alkyl group having 1 to 4 carbon atoms. R a13 , and R a14 Specific examples of the halogenated alkyl group having 1 to 4 carbon atoms as the halogenated alkyl group include a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a bromomethyl group, a dibromomethyl group, a tribromomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 3,3,3-trifluoroethyl group, a pentafluoroethyl group, and a heptafluoropropyl group.

[0181] Suitable examples of the group represented by formula (A-2e-b1) include groups represented by the following formulas: [ka]

[0182] The group represented by formula (A-2e-b1) is R A14The radical polymerizable group-containing group and the cationically polymerizable group-containing group are as described above. Preferred specific examples of the radical polymerizable group-containing group and preferred specific examples of the cationically polymerizable group-containing group are the same as the preferred specific examples of the radical polymerizable group-containing group and preferred specific examples of the cationically polymerizable group-containing group described for the compound represented by Formula (A-2e-a).

[0183] Specific examples of suitable compounds represented by formula (A-2e-b) include compounds of the following formula: A is a group selected from the group consisting of a (meth)acryloyloxy group, a (meth)acryloylthio group, a 3-(meth)acryloyloxy-2-hydroxy-n-propyloxycarbonyl group, and a glycidyloxy group. Y A is a group selected from the group consisting of quinolin-3-yl, phenyl, 4-cyanophenyl, 3-cyanophenyl, 2-cyanophenyl, 3,4-dicyanophenyl, 4-nitrophenyl, 4-methoxyphenyl, 4-phenylthiophenyl, 4-phenylsulfonylphenyl, 4-iodophenyl, benzothiazol-2-yl, 2-mercaptobenzothiazol-5-yl, 4-phenylphenyl, 4-(4-nitrophenyl)phenyl, 4-(4-cyanophenyl)phenyl, naphthalen-1-yl, and 4-(4-phenylphenyl)phenyl.

[0184] [ka]

[0185] The method for producing the compound represented by formula (A-2e-b) is not particularly limited. Typically, a cyanuric halide such as cyanuric chloride is reacted with R A11 -NH2, R A12 -NH2 and R A13The compound can be produced by reacting the aromatic amine represented by —NH with the cyanuric halide. These multiple amines may be reacted with the cyanuric halide simultaneously or sequentially, preferably sequentially.

[0186] Furthermore, when the aromatic ring-containing group bonded to the triazine ring via -NH- has a radical polymerizable group-containing group or a cationically polymerizable group-containing group, the radical polymerizable group-containing group or the cationically polymerizable group-containing group can also be generated by reacting an aromatic amine having a functional group such as a hydroxyl group, a mercapto group, a carboxyl group, or an amino group with a cyanuric halide, and then reacting the functional group with a compound that provides a radical polymerizable group-containing group or a cationically polymerizable group-containing group. Examples of compounds that provide a radical polymerizable group-containing group or a cationically polymerizable group-containing group include compounds having a polymerizable group such as (meth)acrylic acid, (meth)acrylic acid halide, halogenated olefin, epichlorohydrin, and glycidyl (meth)acrylate. As the reaction between a functional group such as a hydroxyl group, a mercapto group, a carboxy group, or an amino group and a compound having a polymerizable group, well-known reactions that produce an ether bond, a carboxylic acid ester bond, a carboxylic acid amide bond, and a thioether bond can be used.

[0187] The reaction for forming the radical polymerizable group-containing group or the cationically polymerizable group-containing group may be a multi-step reaction. For example, a cyanuric halide is reacted with an aromatic amine having a phenolic hydroxyl group, and then the phenolic hydroxyl group is reacted with epichlorohydrin to be glycidylated, and then the glycidyl group is reacted with acrylic acid, thereby introducing a radical polymerizable group-containing group represented by the following formula onto the aromatic ring. -O-CH2-CHOH-CH2-O-CO-CH=CH2 The above reaction is an example, and the radical polymerizable group-containing group or the cationically polymerizable group-containing group can be formed by carrying out a combination of various reactions.

[0188] The compound represented by formula (A-2e-b) is usually synthesized in an organic solvent. Such an organic solvent is not particularly limited as long as it is an inert solvent that does not react with cyanuric halide, aromatic amine, radical polymerizable group, cationic polymerizable group, etc. As the solvent, the organic solvents exemplified as specific examples of the solvent (S) can be used. In producing the compound represented by formula (A-2e-b), a cyanuric halide and R A11 -NH2, R A12 -NH2 and R A13 The temperature at which the reaction with aromatic amines such as the aromatic amine represented by -NH2 is carried out is not particularly limited. Typically, the reaction temperature is preferably 0°C or higher and 150°C or lower.

[0189] The content of the photopolymerizable compound (A) in the composition is not particularly limited as long as the desired effect is not impaired. The content of the photopolymerizable compound (A) in the composition is preferably 0.1 parts by mass or more and 50 parts by mass or less, more preferably 0.5 parts by mass or more and 40 parts by mass or less, and particularly preferably 1 part by mass or more and 25 parts by mass or less, when the mass of the composition excluding the mass of the solvent (S) described below is taken as 100 parts by mass.

[0190] <Inorganic fine particles (B)> The composition contains inorganic fine particles (B). The material of the inorganic fine particles (B) is not particularly limited as long as it is an inorganic material. The inorganic fine particles (B) are preferably one or more types selected from the group consisting of metal oxide fine particles (B1) and metal fine particles (B2). When the composition contains metal oxide fine particles (B1), it is easy to form a material with a high refractive index using the composition. When the composition contains metal fine particles (B2), the material formed using the composition is imparted with electrical conductivity or the material formed using the composition is enhanced in light absorption of a specific wavelength. For this reason, compositions containing metal fine particles (B2) are used to form materials applicable to bandpass filters. The type of metal oxide constituting the metal oxide fine particles (B1) is not particularly limited as long as the desired effect is not impaired. Preferred examples of the metal oxide fine particles (B1) include at least one selected from the group consisting of zirconium oxide fine particles, titanium oxide fine particles, barium titanate fine particles, cerium oxide fine particles, and niobium pentoxide fine particles. The type of metal constituting the metal fine particles (B2) is not particularly limited as long as the desired effect is not impaired. The metal constituting the metal fine particles (B2) may be a simple substance or an alloy. Preferred examples of the metal fine particles (B2) include gold fine particles and platinum fine particles. Other preferred examples of the inorganic fine particles (B) include silicon fine particles (SiNC (silicon nanoparticles)), which are semi-metallic fine particles. The composition may contain one type of these inorganic fine particles (B) alone or two or more types in combination.

[0191] The average particle size of the inorganic fine particles (B) is preferably 500 nm or less, and more preferably 2 nm or more and 100 nm or less, from the viewpoints of the transparency of the material formed using the composition and the dispersion stability of the inorganic fine particles (B) in the composition.

[0192] The metal oxide fine particles (B1) are preferably those whose surfaces are modified with ethylenically unsaturated double bond-containing groups. When the surface of the metal oxide fine particles (B1) is modified with an ethylenically unsaturated double bond-containing group, aggregation of the metal oxide fine particles (B1) is less likely to occur. Therefore, when the surface of the metal oxide fine particles (B1) is modified with an ethylenically unsaturated double bond-containing group, localization of the metal oxide fine particles (B1) in a material formed using the composition is particularly easily suppressed.

[0193] For example, by applying a capping agent containing an ethylenically unsaturated double bond to the surface of metal oxide fine particles (B1), metal oxide fine particles (B1) whose surface is modified with an ethylenically unsaturated double bond-containing group via a chemical bond such as a covalent bond can be obtained.

[0194] There are no particular limitations on the method for bonding a capping agent containing an ethylenically unsaturated double bond to the surface of the metal oxide fine particles (B1) via a chemical bond such as a covalent bond. Hydroxyl groups are usually present on the surface of the metal oxide fine particles (B1). By reacting these hydroxyl groups with reactive groups of the capping agent, the capping agent is covalently bonded to the surface of the metal oxide fine particles (B1). Preferred examples of the reactive group possessed by the capping agent include trialkoxysilyl groups such as trimethoxysilyl group and triethoxyl group; dialkoxysilyl groups such as dimethoxysilyl group and diethoxysilyl group; monoalkoxysilyl groups such as monomethoxysilyl group and monoethoxysilyl group; trihalosilyl groups such as trichlorosilyl group; dihalosilyl groups such as dichlorosilyl group; monohalosilyl groups such as monochlorosilyl group; carboxy group; halocarbonyl groups such as chlorocarbonyl group; hydroxyl group; phosphono group (-P(=O)(OH)2); and phosphate group (-OP(=O)(OH)2).

[0195] The trialkoxysilyl group, dialkoxysilyl group, monoalkoxysilyl group, trihalosilyl group, dihalosilyl group, and monohalosilyl group form a siloxane bond with the surface of the metal oxide nanoparticles (B). The carboxy group and the halocarbonyl group form a bond represented by (metal oxide -O-CO-) with the surface of the metal oxide fine particles (B1). The hydroxyl groups form bonds represented by (metal oxide-O-) with the surfaces of the metal oxide fine particles (B). The phosphono group and the phosphate group form a bond represented by (metal oxide-OP(=O)<) with the surface of the metal oxide fine particles (B1).

[0196] In the capping agent, the group that bonds to the reactive group includes a hydrogen atom and various organic groups, which may contain heteroatoms such as O, N, S, P, B, Si, and halogen atoms. Examples of the group that bonds to the reactive group include an alkyl group, which may be linear or branched and may be interrupted by an oxygen atom (-O-), an alkenyl group, which may be linear or branched and may be interrupted by an oxygen atom (-O-), an alkynyl group, which may be linear or branched and may be interrupted by an oxygen atom (-O-), a cycloalkyl group, an aromatic hydrocarbon group, and a heterocyclic group. These groups may be substituted with a substituent such as a halogen atom, an epoxy group-containing group such as a glycidyl group, a hydroxyl group, a mercapto group, an amino group, a (meth)acryloyl group, an isocyanate group, etc. The number of substituents is not particularly limited.

[0197] In addition, the group bonded to the reactive group may be -(SiR b1 R b2 -O-) r -(SiR b3 R b4 -O-) s -R b5 Also preferred is a group represented by R b1 , R b2 , R b3 , and Rb4 are each an organic group which may be the same or different. Suitable examples of the organic group include alkyl groups such as methyl and ethyl groups, alkenyl groups such as vinyl and allyl groups, aromatic hydrocarbon groups such as phenyl, naphthyl and tolyl groups, epoxy group-containing groups such as 3-glycidoxypropyl groups, and (meth)acryloyloxy groups. In the above formula, R b5 Examples of end groups include -Si(CH3)3, -Si(CH3)2H, -Si(CH3)2(CH=CH2), and -Si(CH3)2(CH2CH2CH2CH3). In the above formula, r and s are each independently an integer of 0 to 60. In the above formula, r and s cannot both be 0.

[0198] Specific preferred examples of the capping agent include unsaturated group-containing alkoxysilanes such as vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, 1-hexenyltrimethoxysilane, 1-hexenyltriethoxysilane, 1-octenyltrimethoxysilane, 1-octenyltriethoxysilane, 3-acryloyloxypropyltrimethoxysilane, 3-acryloylpropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, and 3-methacryloyloxypropyltriethoxysilane; unsaturated group-containing alcohols such as 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, allyl alcohol, ethylene glycol monoallyl ether, propylene glycol monoallyl ether, and 3-allyloxypropanol; (meth)acrylic acid; and (meth)acrylic acid halides such as (meth)acrylic acid chloride.

[0199] The amount of the capping agent used when bonding the capping agent to the surface of the metal oxide fine particles (B1) via a chemical bond such as a covalent bond is not particularly limited. Preferably, a sufficient amount of the capping agent is used to react with almost all of the hydroxyl groups on the surface of the metal oxide fine particles (B1).

[0200] The content of the inorganic fine particles (B) in the composition is not particularly limited as long as it does not impair the object of the present invention. The content of the inorganic fine particles (B) in the composition is preferably 5% by mass or more and 95% by mass or less, more preferably 35% by mass or more and 93% by mass or less, and even more preferably 40% by mass or more and 90% by mass or less, based on the mass of the composition excluding the mass of the solvent (S). By ensuring that the content of inorganic fine particles (B) in the composition is within the above range, it is easy to obtain a composition in which the inorganic fine particles (B) are stably dispersed, and it is also easy to use the composition to form a material that has the desired effects brought about by the use of the inorganic fine particles (B). When the inorganic fine particles (B) are metal oxide fine particles (B1), the content of the metal oxide fine particles (B1) in the composition is preferably 90% by mass or more, more preferably 90% by mass or more and 98% by mass or less, and even more preferably 90% by mass or more and 95% by mass or less, based on the mass of the composition excluding the mass of the solvent (S), in particular from the viewpoint of facilitating the formation of a material with a high refractive index. In addition, when the surface of the metal oxide fine particles (B1) is modified with an ethylenically unsaturated double bond-containing group, the mass of the capping agent having the ethylenically unsaturated double bond-containing group present on the surface of the metal oxide fine particles (B1) is included in the mass of the metal oxide fine particles (B1).

[0201] [Plasticizer (D)] The composition may contain a plasticizer (D), which is a component that reduces the viscosity of the composition without significantly impairing the physical properties, such as the high refractive index, of a material formed using the composition.

[0202] The plasticizer (D) is preferably a compound represented by the following formula (d-1). R d1 -R d3 r -X d -R d4 s -R d2 (d-1) (In formula (d-1), R d1 , and R d2 are each independently a phenyl group optionally having 1 to 5 substituents, and the substituents are selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a halogen atom; R d3 , and R d4 are each independently a methylene group or an ethane-1,2-diyl group, r and s are each independently 0 or 1, and X d is an oxygen atom or a sulfur atom.

[0203] By including such a plasticizer (D) in the composition, the viscosity of the composition can be reduced without significantly impairing the physical properties such as the high refractive index of the material formed using the composition. From the viewpoint of reducing the viscosity of the composition, the viscosity of the plasticizer (D) measured at 25° C. with an E-type viscometer is preferably 10 cP or less, more preferably 8 cP or less, and even more preferably 6 cP or less. In addition, since the plasticizer (D) is less likely to volatilize and the effect of reducing the viscosity of the composition can be easily maintained, the boiling point of the plasticizer (D) under atmospheric pressure is preferably 250° C. or higher, and more preferably 260° C. or higher. The upper limit of the boiling point of the plasticizer (D) under atmospheric pressure is not particularly limited, but may be, for example, 300° C. or lower, or 350° C. or lower.

[0204] R in formula (d-1) d1 , and R d2 are each independently a phenyl group which may have 1 to 5 substituents. The substituent bonded to the phenyl group is a group selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a halogen atom. When the phenyl group has a substituent, the number of the substituents is not particularly limited. The number of the substituents is 1 to 5, preferably 1 or 2, and more preferably 1. From the viewpoint of reducing the viscosity of the composition, R d1 , and R d2 are each preferably an unsubstituted phenyl group.

[0205] Examples of the alkyl group having 1 to 4 carbon atoms as a substituent include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Examples of the alkoxy group having 1 to 4 carbon atoms as a substituent include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, and a tert-butyloxy group. Examples of the halogen atom as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0206] R in formula (d-1) d3 , and R d4are each independently a methylene group or an ethane-1,2-diyl group, and r and s are each independently 0 or 1. X in formula (d-1) d is an oxygen atom or a sulfur atom.

[0207] Preferred specific examples of the compound represented by formula (d-1) described above include diphenyl ether, diphenyl sulfide, dibenzyl ether, dibenzyl sulfide, diphenethyl ether, and diphenethyl sulfide. Among these, diphenyl sulfide and / or dibenzyl ether are more preferred.

[0208] The content of the plasticizer (D) in the composition is preferably more than 0 mass% and not more than 35 mass%, more preferably 5 mass% or more and 15 mass% or less, relative to the mass of the entire composition, in order to achieve both viscosity adjustment and dispersibility of the inorganic fine particles (B).

[0209] [Nitrogen-containing compound (E)] For the purpose of easily suppressing localization of the inorganic fine particles (B) in a material formed using the composition, the composition may contain, as the nitrogen-containing compound (E), an amine compound (E1) represented by the following formula (e1) and / or an imine compound (E2) represented by the following formula (e2): NR e1 R e2 R e3 (e1) (In formula (e1), R e1 , R e2 , and R e3 are each independently a hydrogen atom or an organic group. R e4 -N=CR e5 R e6 (e2) (In formula (e2), R e4 , R e5 , and R de6 are each independently a hydrogen atom or an organic group.

[0210] In formula (e1) and formula (e2), R e1 , Re2 , R e3 , R e4 , R e5 , and R de6 When is an organic group, the organic group can be selected from various organic groups as long as the desired effect is not impaired. As the organic group, a carbon atom-containing group is preferred, and a group consisting of one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 to 50, more preferably 1 to 20. Suitable examples of the organic group include an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, a phenylalkyl group which may have a substituent, a naphthyl group which may have a substituent, a naphthylalkyl group which may have a substituent, and a heterocyclyl group which may have a substituent.

[0211] The number of carbon atoms in the alkyl group as an organic group is preferably 1 to 20, more preferably 1 to 6. The alkyl group may have a linear or branched chain structure. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, n-decyl, and isodecyl. The alkyl group may also contain an ether bond (-O-) in the carbon chain. Examples of alkyl groups having an ether bond in the carbon chain include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxyethoxyethyl, and methoxypropyl.

[0212] The number of carbon atoms in the cycloalkyl group as an organic group is preferably 3 to 10, more preferably 3 to 6. Specific examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0213] The number of carbon atoms in the phenylalkyl group as an organic group is preferably 7 to 20, more preferably 7 to 10. The number of carbon atoms in the naphthylalkyl group as an organic group is preferably 11 to 20, more preferably 11 to 14. Specific examples of the phenylalkyl group include a benzyl group, a 2-phenylethyl group, a 3-phenylpropyl group, and a 4-phenylbutyl group. Specific examples of the naphthylalkyl group include an α-naphthylmethyl group, a β-naphthylmethyl group, a 2-(α-naphthyl)ethyl group, and a 2-(β-naphthyl)ethyl group. The phenylalkyl group or the naphthylalkyl group may further have a substituent on the phenyl group or the naphthyl group.

[0214] In the case of a heterocyclyl group as the organic group, the heterocyclyl group is R c4 is a heterocyclyl group, and the heterocyclyl group may further have a substituent.

[0215] The heterocyclyl group as an organic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. The heterocyclyl group is preferably a 5- or 6-membered monocyclic ring containing one or more N, S, or O atoms, or a heterocyclyl group in which such monocyclic rings are fused with each other or such monocyclic rings are fused with a benzene ring. When the heterocyclyl group is a fused ring, the number of rings is limited to three. Examples of heterocycles constituting such heterocyclyl groups include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran.

[0216] When the phenyl group, naphthyl group, and heterocyclyl group contained in the above organic group have a substituent, examples of the substituent include an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, a halogenated alkyl group having from 1 to 6 carbon atoms, a halogenated alkoxy group having from 1 to 6 carbon atoms, a saturated aliphatic acyl group having from 2 to 7 carbon atoms, an alkoxycarbonyl group having from 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having from 2 to 7 carbon atoms, a monoalkylamino group having an alkyl group having from 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having from 1 to 6 carbon atoms, a benzoyl group, a halogen atom, a nitro group, and a cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in the organic group have a substituent, the number of the substituents is not particularly limited, and is preferably from 1 to 4. When the phenyl group, naphthyl group, and heterocyclyl group contained in the organic group have multiple substituents, the multiple substituents may be the same or different.

[0217] In formula (e1), Re1 , R e2 , and R e3 are each independently a hydrogen atom or an organic group, and R e1 , R e2 , and R e3 At least one of the groups is an aromatic group-containing group. In addition, in formula (e2), R e4 , R e5 , and R de6 are each independently a hydrogen atom or an organic group, and R e4 , R e5 , and R de6 At least one of the groups is an aromatic group-containing group. The aromatic ring in the aromatic group-containing group may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The aromatic group-containing group is preferably a hydrocarbon group. The aromatic group-containing group is preferably an aromatic hydrocarbon group (aryl group) or an aralkyl group. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthalene-1-yl group, and a naphthalene-2-yl group. Of these aromatic hydrocarbon groups, a phenyl group is preferred. Aralkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl, and 4-phenylbutyl groups.

[0218] In formula (e1), R e1 , R e2 , and R e3 At least one of e1 In addition, in formula (d2), R is preferably a group represented by —CH—. e4 Ar e1 A group represented by -CH2- is preferred. e1 is an aromatic group which may have a substituent. Ar e1 The aromatic group as Ar may be an aromatic hydrocarbon group or an aromatic heterocyclic group. e1 The aromatic group as the aromatic hydrocarbon group is preferably an aromatic hydrocarbon group. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthalene-1-yl group, and a naphthalene-2-yl group. Of these aromatic hydrocarbon groups, a phenyl group is preferred. Ar e1 The substituents that the aromatic group may have are R e1 , R e2 , R e3 , R e4 , R e5 , and R e6 When the organic group as is a phenyl group, a naphthyl group, or a heterocyclyl group, the substituents that may be substituted by these groups are the same as those that may be substituted by these groups.

[0219] Specific preferred examples of the amine compound represented by formula (e1) include triphenylamine, N,N-diphenylbenzylamine, N-phenyldibenzylamine, tribendialumine, N,N-dimethylphenylamine, N-methyldiphenylamine, N,N-dimethylbenzylamine, N-methyldibenzylamine, N-methyl-N-benzylphenylamine, N,N-diethylphenylamine, N-ethyldiphenylamine, N,N-diethylbenzylamine, N-ethyldibenzylamine, and N-ethyl-N-benzylphenylamine.

[0220] Specific preferred examples of the imine compound represented by formula (e2) include N-benzylphenylmethanimine, N-benzyldiphenylmethanimine, N-benzyl-1-phenylethanimine, and N-benzylpropan-2-imine.

[0221] The content of the nitrogen-containing compound (E) in the composition is not particularly limited as long as the desired effect is not impaired. The content of the nitrogen-containing compound (E) is preferably 5% by mass or more and 25% by mass or less, and more preferably 7% by mass or more and 20% by mass or less, based on the mass of the photopolymerizable compound (A).

[0222] <Triazine Compound (F)> For the purpose of increasing the refractive index of a material formed using the composition, the composition may contain a compound represented by the following formula (F1) as the triazine compound (F). [ka]

[0223] In formula (F1), R F1 , R F2 , and R F3 are each independently a monocyclic aromatic group which may have a substituent, or a fused aromatic group which may have a substituent. However, R F1 , R F2 , and R F3 does not contain a radical polymerizable group-containing group or a cationically polymerizable group-containing group. When the monocyclic aromatic group or the fused aromatic group has a substituent, the substituent does not contain an aromatic ring. The three -NH- groups bonded to the triazine ring are each R F1 , R F2 , and R F3 It bonds to the aromatic ring in the center.

[0224] R F1 , R F2 , and R F3 The monocyclic aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group, and examples of the monocyclic aromatic group include a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a furanyl group, a thienyl group, an oxazolyl group, and a thiazolyl group.

[0225] Examples of the substituent that the monocyclic aromatic group may have include a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a nitro group, and a monovalent organic group, provided that the monovalent organic group does not contain an aromatic ring. Examples of the halogen atom as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the monovalent organic group include an alkyl group, an alkoxy group, an alkoxyalkyl group, an aliphatic acyl group, an aliphatic acyloxy group, an alkoxycarbonyl group, an alkylthio group, and an aliphatic acylthio group.

[0226] The number of carbon atoms of the monovalent organic group as a substituent is not particularly limited as long as the desired effect is not impaired. The number of carbon atoms of the monovalent organic group as a substituent is, for example, preferably 1 to 20, more preferably 1 to 12, and even more preferably 1 to 8. For alkoxyalkyl groups, aliphatic acyl groups, aliphatic acyloxy groups, alkoxycarbonyl groups, alkoxyalkylthio groups, and aliphatic acylthio groups, the lower limit of the number of carbon atoms is 2.

[0227] Preferred specific examples of the alkyl group as the substituent include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group.

[0228] Specific preferred examples of the alkoxy group as the substituent include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, and an n-octyloxy group.

[0229] Preferred specific examples of the alkoxyalkyl group as the substituent include a methoxymethyl group, an ethoxymethyl group, an n-propyloxymethyl group, an n-butyloxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-n-propyloxyethyl group, a 2-n-butyloxyethyl group, a 3-methoxy-n-propyloxy group, a 3-ethoxy-n-propyloxy group, a 3-n-propyloxy-n-propyloxy group, a 3-n-butyloxy-n-propyloxy group, a 4-methoxy-n-butyloxy group, a 4-ethoxy-n-butyloxy group, a 4-n-propyloxy-n-butyloxy group, and a 4-n-butyloxy-n-butyloxy group.

[0230] Preferred specific examples of the aliphatic acyl group as the substituent include an acetyl group, a propionyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, and an octanoyl group.

[0231] Preferred specific examples of the aliphatic acyloxy group as the substituent include an acetoxy group, a propionyloxy group, a butanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a heptanoyloxy group, and an octanoyloxy group.

[0232] Preferred specific examples of the alkoxycarbonyl group as a substituent include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, a sec-butyloxycarbonyl group, a tert-butyloxycarbonyl group, an n-pentyloxycarbonyl group, an n-hexyloxycarbonyl group, an n-heptyloxycarbonyl group, and an n-octyloxycarbonyl group.

[0233] Specific preferred examples of the alkylthio group as the substituent include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, an n-pentylthio group, an n-hexylthio group, an n-heptylthio group, and an n-octylthio group.

[0234] Specific preferred examples of the aliphatic acylthio group as the substituent include an acetylthio group, a propionylthio group, a butanoylthio group, a pentanoylthio group, a hexanoylthio group, a heptanoylthio group, and an octanoylthio group.

[0235] When the monocyclic aromatic group has a substituent, the number of the substituents is not particularly limited as long as the desired effect is not impaired. When the monocyclic aromatic group has a substituent, the number of the substituents is preferably 1 or more and 4 or less, more preferably 1 or 2, and particularly preferably 1. When the monocyclic aromatic group has multiple substituents, the multiple substituents may be different from each other.

[0236] Examples of the monocyclic aromatic group which may have a substituent as described above include a phenyl group, a 4-cyanophenyl group, a 3-cyanophenyl group, a 2-cyanophenyl group, a 2,3-dicyanophenyl group, a 2,4-dicyanophenyl group, a 2,5-dicyanophenyl group, a 2,6-dicyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, a 4-nitrophenyl group, a 3-nitrophenyl group, a 2-nitrophenyl group, a 4-chlorophenyl group, a 3-chlorophenyl group, a 2-chlorophenyl group, a 4-bromophenyl group, a 3-bromophenyl group, a 2-bromophenyl group, a 4-iodophenyl group, a 3-iodophenyl group, a 2-iodophenyl group, a 4-methoxyphenyl group, a 3-methoxyphenyl group, a 2-methoxyphenyl group, a 4-methylphenyl group, a 3-methylphenyl group, and a 2-methylphenyl group.

[0237] Of these groups, phenyl, 4-cyanophenyl, 3-cyanophenyl, 2-cyanophenyl, 4-nitrophenyl, 3-nitrophenyl, and 2-nitrophenyl groups are preferred, and phenyl and 4-cyanophenyl groups are more preferred.

[0238] R F1 , R F2 , and R F3 The fused aromatic group as defined above is a group in which one hydrogen atom has been removed from a fused polycycle in which two or more aromatic monocycles are fused. The number of aromatic monocycles constituting the fused aromatic group is not particularly limited. The number of aromatic monocycles constituting the fused aromatic group is preferably 2 or 3, more preferably 2. In other words, the fused aromatic group is preferably a bicyclic fused aromatic group or a tricyclic fused aromatic group, and more preferably a bicyclic fused aromatic group. The fused aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group.

[0239] Examples of the bicyclic fused aromatic group include a naphthalen-1-yl group, a naphthalen-2-yl group, a quinolin-2-yl group, a quinolin-3-yl group, a quinolin-4-yl group, a quinolin-5-yl group, a quinolin-6-yl group, a quinolin-7-yl group, a quinolin-8-yl group, an isoquinolin-1-yl group, an isoquinolin-3-yl group, an isoquinolin-4-yl group, an isoquinolin-5-yl group, an isoquinolin-6-yl group, an iso ... Examples of such groups include quinolin-7-yl group, isoquinolin-8-yl group, benzoxazol-2-yl group, benzoxazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-7-yl group, benzothiazol-2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group, benzothiazol-6-yl group, and benzothiazol-7-yl group.

[0240] Examples of tricyclic fused aromatic groups include anthracen-1-yl, anthracen-2-yl, anthracen-9-yl, phenanthrene-1-yl, phenanthrene-2-yl, phenanthrene-3-yl, phenanthrene-4-yl, phenanthrene-9-yl, acridine-1-yl, acridine-2-yl, acridine-3-yl, acridine-4-yl, and acridine-9-yl.

[0241] The substituents which may be substituted on polycyclic fused aromatic groups such as bicyclic fused aromatic groups and tricyclic fused aromatic groups are the same as the substituents which may be substituted on monocyclic aromatic groups.

[0242] As the fused ring aromatic group which may have a substituent as explained above, a naphthalen-1-yl group, a naphthalen-2-yl group, a quinolin-2-yl group, a quinolin-3-yl group, a quinolin-4-yl group, a quinolin-5-yl group, a quinolin-6-yl group, a quinolin-7-yl group, a quinolin-8-yl group, a benzothiazol-2-yl group, or a 2-mercaptobenzothiazol-6-yl group is preferred.

[0243] Of these groups, a naphthalen-1-yl group, a quinolin-3-yl group, a quinolin-4-yl group, and a 2-mercaptobenzothiazol-6-yl group are preferred, and a naphthalen-1-yl group is more preferred.

[0244] Among the compounds represented by formula (F1) explained above, R F1 , R F2 , and R F3 one or two of R are naphthyl groups which may have a substituent; F1 , R F2 , and R F3 A compound in which one or two of the groups are a 4-cyanophenyl group or a benzothiazolyl group is preferred. The optionally substituted naphthyl group is preferably a naphthalen-1-yl group.

[0245] Specific preferred examples of the compound represented by formula (F1) include compounds of the following formulas:

[0246] [ka]

[0247] The method for producing the compound represented by formula (F1) is not particularly limited. Typically, a cyanuric halide such as cyanuric chloride is reacted with R F1 -NH2, R F2 -NH2 and R F3 The compound can be produced by reacting the aromatic amine represented by —NH with the cyanuric halide. These multiple amines may be reacted with the cyanuric halide simultaneously or sequentially, preferably sequentially.

[0248] The compound represented by formula (F1) is usually synthesized in an organic solvent. Such an organic solvent is not particularly limited as long as it is an inert solvent that does not react with cyanuric halide, aromatic amine, radical polymerizable group, cationic polymerizable group, etc. As the solvent, organic solvents exemplified as specific examples of the solvent (S) described below can be used. In preparing the compound of formula (F1), a cyanuric halide and R F1 -NH2, R F2 -NH2 and R F3 The temperature at which the reaction with aromatic amines such as the aromatic amine represented by -NH2 is carried out is not particularly limited. Typically, the reaction temperature is preferably 0°C or higher and 150°C or lower.

[0249] The content of the triazine compound (F) in the composition is not particularly limited as long as the desired effect is not impaired. The content of the triazine compound (F) in the composition is, for example, preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 0.3 parts by mass or more and 20 parts by mass or less, and even more preferably 0.5 parts by mass or more and 15 parts by mass or less, when the mass of the composition excluding the mass of the solvent (S) described below is taken as 100 parts by mass.

[0250] <Solvent (S)> The composition may contain a solvent (S) for the purpose of adjusting the coating property, etc. The type of solvent (S) is not particularly limited as long as it does not inhibit the desired effect.

[0251] Suitable examples of the solvent (S) 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 monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether (HO-CH2CH2CH2-O-CH3), propylene glycol monomethyl ether (HO-C(CH3)HCH2-O-CH3, or H3C-OC(CH3)HCH2-OH), propylene glycol monoethyl ether (HO-CH2CH2CH2-O-CH2CH3), propylene glycol monoethyl ether (HO-C(CH3)HCH2-O-CH2CH3, or H3CH2C-OC(CH3)HCH2-OH), propylene glycol mono-n-propyl ether (HO- CH2CH2CH2-O-CH2CH2CH3), propylene glycol mono-n-propyl ether (HO-C(CH3)HCH2-O-CH2CH2CH3, or H3CH2CH2C-OC(CH3)HCH2-OH), propylene glycol mono-n-butyl ether (HO-CH2CH2CH2-O-CH2CH2CH2CH3), propylene glycol mono-n-butyl ether (HO-C(CH3)HCH2-O-CH2CH2CH2CH3, or H3CH2CH2CH2C-OC(CH3)HCH2-OH), di Propylene glycol monoethyl ether (HO-(CH2CH2CH2-O)2-CH3), dipropylene glycol monomethyl ether (HO-(C(CH3)HCH2-O)2-CH3, or H3C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)2-CH2CH3), dipropylene glycol monoethyl ether (HO-(C(CH3)HCH2-O)2-CH2CH3, or H3CH2C-O-(C(CH3)HCH2-O)2-H),Dipropylene glycol mono-n-propyl ether (HO-(CH2CH2CH2-O)2-CH2CH2CH3, or H3CH2CH2C-O-(CH2CH2CH2-O)2-H), dipropylene glycol mono-n-propyl ether (HO-(C(CH3)HCH2-O)2-CH2CH2CH3, or H3CH2CH2C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol mono-n-butyl ether (HO-(CH2CH2CH2-O)2-CH2CH2CH2CH3, or H3CH2CH2CH2C-O-(CH2C H2CH2-O)2-H), dipropylene glycol mono-n-butyl ether (HO-(C(CH3)HCH2-O)2-CH2CH2CH2CH3, or H3CH2CH2CH2C-O-(C(CH3)HCH2-O)2-H), tripropylene glycol monomethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), tripropylene glycol monomethyl ether (H3C-O-(C(CH3)HCH2-O)3-H), tripropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), tripropylene glycol monomethyl ether (H3C-O-(C(CH3)HCH2-O)3-H), tripropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), tripropylene glycol monomethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), (Poly)alkylene glycol monoalkyl ethers such as propylene glycol monoethyl ether (HO-(C(CH3)HCH2-O)3-CH2CH3, or H3CH2C-O-(C(CH3)HCH2-O)3-H); (Poly)alkylene glycol monoalkyl ether acetates 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; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol methyl ethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ethyl ether,Other ethers such as dipropylene glycol diethyl ether and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; alkyl lactic acid esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl- Examples of suitable esters include 3-methoxybutyl propionate, 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, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; and amides such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, with (poly)alkylene glycol monoalkyl ether acetates being preferred.

[0252] In order to ensure good application by inkjet printing, the solvent (S) preferably contains a solvent having a boiling point of 140°C or higher at atmospheric pressure, and more preferably contains a high-boiling-point solvent (S1) having a boiling point of 170°C or higher at atmospheric pressure.

[0253] Specific examples of solvents having a boiling point of 140°C or higher under atmospheric pressure include ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, and propylene glycol monomethyl ether (HO-CH2CH2CH2-O-CH 3), propylene glycol monoethyl ether (HO-CH2CH2CH2-O-CH2CH3), propylene glycol mono-n-propyl ether (HO-CH2CH2CH2-O-CH2CH2CH3), propylene glycol mono-n-propyl ether (HO-C(CH3)HCH2-O-CH2CH2CH3, or H3CH2CH2C-OC(CH3)HCH2-OH), propylene glycol mono-n-butyl ether (HO-CH2CH2CH2-O-CH2CH2CH2CH3), propylene glycol mono-n -butyl ether (HO-C(CH3)HCH2-O-CH2CH2CH2CH3, or H3CH2CH2CH2C-OC(CH3)HCH2-OH), dipropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)2-CH3), dipropylene glycol monomethyl ether (HO-(C(CH3)HCH2-O)2-CH3, or H3C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)2-CH2CH3), dipropylene glycol dipropylene glycol monoethyl ether (HO-(C(CH3)HCH2-O)2-CH2CH3, or H3CH2C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol mono-n-propyl ether (HO-(CH2CH2CH2-O)2-CH2CH2CH3, or H3CH2CH2C-O-(CH2CH2CH2-O)2-H), dipropylene glycol mono-n-propyl ether (HO-(C(CH3)HCH2-O)2-CH2CH2CH3, or H3CH2CH2C-O-(C(CH3)HCH2-O)2-H),Dipropylene glycol mono-n-butyl ether (HO-(CH2CH2CH2-O)2-CH2CH2CH2CH3, or H3CH2CH2CH2C-O-(CH2CH2CH2-O)2-H), dipropylene glycol mono-n-butyl ether (HO-(C(CH3)HCH2-O)2-CH2CH2CH2CH3, or H3CH2CH2CH2CH2C-O-(C(CH3)HCH2-O)2-H), tripropylene glycol monomethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), tripropylene glycol monomethyl ether (H3C-O-(C(CH3)HCH2-O)3-H), tripropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), tripropylene glycol monoethyl ether (HO-(C(CH3)HCH2-O)3 -CH2CH3, or H3CH2C-O-(C(CH3)HCH2-O)3-H), diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, cyclohexanone, 2-heptanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, n-butyl butyrate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate, N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide.

[0254] Specific examples of the high boiling point solvent (S1) include ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol mono-n-butyl ether (HO-CH2CH2CH2-O-CH2CH2CH2CH3), propylene glycol mono-n-butyl ether (HO-C (CH3)HCH2-O-CH2CH2CH2CH3, or H3CH2CH2CH2C-OC(CH3)HCH2-OH), dipropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)2-CH3), dipropylene glycol monomethyl ether (HO-(C(CH3)HCH2-O)2-CH3, or H3C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol monoethyl ether (HO-(CH2CH2CH2-O)2-CH2CH3), dipropylene glycol monoethyl ether (HO-(C(CH3 )HCH2-O)2-CH2CH3, or H3CH2C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol mono-n-propyl ether (HO-(CH2CH2CH2-O)2-CH2CH2CH3, or H3CH2CH2C-O-(CH2CH2CH2-O)2-H), dipropylene glycol mono-n-propyl ether (HO-(C(CH3)HCH2-O)2-CH2CH2CH3, or H3CH2CH2C-O-(C(CH3)HCH2-O)2-H), dipropylene glycol mono-n-butyl ether (HO-(C H2CH2CH2-O)2-CH2CH2CH2CH3, or H3CH2CH2CH2C-O-(CH2CH2CH2-O)2-H), dipropylene glycol mono-n-butyl ether (HO-(C(CH3)HCH2-O)2-CH2CH2CH2CH3, or H3CH2CH2CH2C-O-(C(CH3)HCH2-O)2-H), tripropylene glycol monomethyl ether (HO-(CH2CH2CH2-O)3-CH2CH3), tripropylene glycol monomethyl ether (H3C-O-(C(CH3)HCH2-O)3-H),Examples of suitable hydroxypropyl ethers include tripropylene glycol monoethyl ether (HO-(CHCHCH-O)-CHCH), tripropylene glycol monoethyl ether (HO-(C(CH)HCH-O)-CHCH, or HCHC-O-(C(CH)HCH-O)-H), diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ethyl ether, dipropylene glycol diethyl ether, hydroxyethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate, and N-methylpyrrolidone.

[0255] In terms of ease of achieving the desired effect, the ratio of the mass of the solvent having a boiling point of 140°C or higher or the high-boiling solvent (S1) having a boiling point of 170°C or higher to the mass of the solvent (S) is preferably 20% by mass or higher, more preferably 30% by mass or higher, even more preferably 50% by mass or higher, even more preferably 70% by mass or higher, particularly preferably 90% by mass or higher, and most preferably 100% by mass.

[0256] The content of the solvent (S) is preferably an amount such that the concentration of components other than the solvent (S) in the composition is 1% by mass or more and 99% by mass or less, more preferably 5% by mass or more and 50% by mass or less, and even more preferably 10% by mass or more and 30% by mass or less.

[0257] <Other ingredients> The composition may contain various additives as other components in addition to the above components, as necessary, such as sensitizers, curing accelerators, fillers, dispersants, adhesion promoters such as silane coupling agents, antioxidants, anti-aggregation agents, thermal polymerization inhibitors, antifoaming agents, surfactants, etc. The amounts of these additives used are determined appropriately taking into consideration the amounts in which these additives are normally used in compositions.

[0258] ≪Photosensitive composition≫ The photosensitive composition contains a photopolymerizable compound (A), inorganic fine particles (B), and an initiator (C). The initiator (C) is a component that cures the photopolymerizable compound. The preferred embodiments and amounts of the photopolymerizable compound (A) and the inorganic fine particles (B) used are as described above for the above composition.

[0259] The photosensitive composition may further contain one or more components selected from the group consisting of the plasticizer (D), the nitrogen-containing compound (E), the triazine compound (F), the solvent (S), and other components described above for the composition. The preferred embodiments and amounts of these components are as described above for the composition.

[0260] <Initiator (C)> The photosensitive composition contains an initiator (C) to cure the photopolymerizable compound (A). When the photopolymerizable compound (A) has a radical polymerizable group, a radical polymerization initiator (C1) is used as the initiator (C). When the photopolymerizable compound (A) has a cationic polymerizable group, a cationic polymerization initiator (C2) is used as the initiator (C). A photoinitiator is used as the initiator (C) because it allows regioselective curing of the photosensitive composition and there is no concern about thermal degradation, volatilization, sublimation, etc. of the components of the photosensitive composition. The initiator (C) is not particularly limited, and various conventionally known polymerization initiators can be used.

[0261] Specific examples of photoradical polymerization initiators useful as the radical polymerization initiator (C1) include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenyl Ethan-1-one, bis(4-dimethylaminophenyl) ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, O-acetyl-1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl]ethanone oxime, (9-ethyl-6-nitro-9H-carbazol-3-yl)[4-(2-methoxy-1-methylethoxy)-2-methylphenyl]methanone O-acetyl oxime, 2-(benzoyloxyimino)-1-[4-(phenylthio)phenyl]-1-octanone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 4-benzoyl-4'-methyldimethyl sulfide, 4-dimethylaminobenzoic acid, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 4-dimethylamino-2-ethylhexylbenzoic acid, 4-dimethylamino-2-isoamylbenzoic acid, benzyl β-methoxyethyl acetal, benzyl Dimethyl ketal, 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime, methyl o-benzoylbenzoate, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 1-chloro-4-propoxythioxanthone, thioxanthene, 2-chlorothioxanthene, 2,4-diethylthioxanthene, 2-methylthioxanthene, 2-isopropylthioxanthene, 2-ethylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-Diphenylanthraquinone, azobisisobutyronitrile, benzoyl peroxide, cumene hydroperoxide, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl)-imidazolyl dimer, benzophenone, 2-chlorobenzophenone, p,p'-bisdimethylaminobenzophenone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone Non, Benzyl, Benzoin, Benzoin Methyl Ether, Benzoin Ethyl Ether, Benzoin Isopropyl Ether, Benzoin-n-Butyl Ether, Benzoin Isobutyl Ether, Benzoin Butyl Ether, Acetophenone, 2,2-Diethoxyacetophenone, p-Dimethylacetophenone, p-Dimethylaminopropiophenone, 2-Hydroxy-2-methylpropiophenone, Dichloroacetophenone, Trichloroacetophenone, p-Tert-Butylacetophenone, p-Dimethylaminoacetophenone, p-Tert-Butyl Trichloroacetophenone, p-tert-butyldichloroacetophenone, α,α-dichloro-4-phenoxyacetophenone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, pentyl-4-dimethylaminobenzoate, 9-phenylacridine, 1,7-bis-(9-acridinyl)heptane, 1,5-bis-(9-acridinyl)pentane, 1,3-bis-(9-acridinyl)propane, p-methoxytriazine, 2,4,6-tris(trichloromethyl)-s-triazine, 2-methyl 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(4-diethylamino-2-methylphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxyphenyl)-4,Examples of such photoradical polymerization initiators include 6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)styrylphenyl-s-triazine, and 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)styrylphenyl-s-triazine. These photoradical polymerization initiators can be used alone or in combination of two or more.

[0262] Among the photoradical polymerization initiators, oxime ester compounds are preferred in terms of the sensitivity of the photosensitive composition. The oxime ester compound is preferably a compound having a partial structure represented by the following formula (c1).

[0263] [ka] (In formula (c1), n1 is 0 or 1, R c2 is a monovalent organic group, R c3 represents a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 20 carbon atoms which may have a substituent, or an aryl group which may have a substituent, * is a bond.)

[0264] The compound having the partial structure represented by formula (c1) preferably has a carbazole skeleton, a fluorene skeleton, a diphenyl ether skeleton, or a phenyl sulfide skeleton. The compound having the partial structure represented by formula (c1) preferably has one or two partial structures represented by formula (c1).

[0265] Examples of compounds having a partial structure represented by formula (c1) include compounds represented by the following formula (c2).

[0266] [ka] (In formula (c2), R c1 is a group represented by the following formula (c3), (c4), or (c5): n1 is 0 or 1, R c2 is a monovalent organic group, R c3 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aryl group which may have a substituent.

[0267] [ka] (In formula (c3), R c4 and R c5 are each independently a monovalent organic group, n2 is an integer between 0 and 3, When n2 is 2 or 3, multiple R c5 may be the same or different, and multiple R c5 may be bonded to each other to form a ring. * is a bond.)

[0268] [ka] (In formula (c4), R c6 and R c7 each independently represents a chain alkyl group which may have a substituent, a chain alkoxy group which may have a substituent, a cyclic organic group which may have a substituent, or a hydrogen atom, R c6 and R c7 may be bonded to each other to form a ring, R c7 and a benzene ring in the fluorene skeleton may be bonded to each other to form a ring, R c8is a nitro group or a monovalent organic group, n3 is an integer between 0 and 4, * is a bond.)

[0269] [ka] (In formula (c5), R c9 is a monovalent organic group, a halogen atom, a nitro group, or a cyano group, A is S or O, n4 is an integer between 0 and 4, * is a bond.)

[0270] In formula (c3), R c4 is a monovalent organic group. c4 can be selected from various organic groups as long as it does not impair the object of the present invention. As the organic group, a carbon atom-containing group is preferred, and a group consisting of one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 to 50, more preferably 1 to 20. R c4 Suitable examples of include an alkyl group having from 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having from 3 to 20 carbon atoms which may have a substituent, a saturated aliphatic acyl group having from 2 to 20 carbon atoms which may have a substituent, an alkoxycarbonyl group having from 2 to 20 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a phenylalkyl group having from 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoyl group which may have a substituent, a naphthoxycarbonyl group which may have a substituent, a naphthylalkyl group having from 11 to 20 carbon atoms which may have a substituent, a heterocyclyl group which may have a substituent, and a heterocyclylcarbonyl group which may have a substituent.

[0271] R c4Among these, an alkyl group having 1 to 20 carbon atoms is preferred. The alkyl group may be linear or branched. In view of the good solubility of the compound represented by formula (c3) in the photosensitive composition, R c4 The number of carbon atoms in the alkyl group represented by R is preferably 2 or more, more preferably 5 or more, and particularly preferably 7 or more. In addition, in order to obtain good compatibility between the compound represented by formula (c3) and other components in the photosensitive composition, it is preferable that R c4 The alkyl group as the alkyl group preferably has 15 or less carbon atoms, more preferably 10 or less carbon atoms.

[0272] R c4 When has a substituent, suitable examples of the substituent include a hydroxyl group, an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, an aliphatic acyl group having from 2 to 20 carbon atoms, an aliphatic acyloxy group having from 2 to 20 carbon atoms, a phenoxy group, a benzoyl group, a benzoyloxy group, a group represented by -PO(OR)2 (R is an alkyl group having from 1 to 6 carbon atoms), a halogen atom, a cyano group, and a heterocyclyl group.

[0273] R c4 When R is a heterocyclyl group, the heterocyclyl group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. c4is a heterocyclyl group, the heterocyclyl group is a 5- or 6-membered monocyclic ring containing one or more N, S, or O atoms, or a heterocyclyl group in which such monocyclic rings are fused together or such monocyclic rings are fused with a benzene ring. When the heterocyclyl group is a fused ring, the number of rings is limited to three. Examples of heterocyclic rings constituting such heterocyclyl groups include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran. R c4 When is a heterocyclyl group, examples of the substituent that the heterocyclyl group may have include a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a halogen atom, a cyano group, a nitro group, and the like.

[0274] The above-described R c4 Specific preferred examples of the aryl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a pentan-3-yl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, and a 2-ethylhexyl group. Furthermore, in view of the good solubility of the compound represented by formula (c3) in the photosensitive composition, an n-octyl group and a 2-ethylhexyl group are preferred, and a 2-ethylhexyl group is more preferred.

[0275] In formula (c3), R c5 is a monovalent organic group. c5can be selected from various organic groups as long as it does not impair the object of the present invention. As the organic group, a carbon atom-containing group is preferred, and a group consisting of one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 to 50, more preferably 1 to 20. R c5 Examples of suitable monovalent organic groups include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, an optionally substituted phenyl group, an optionally substituted phenoxy group, an optionally substituted benzoyl group, an optionally substituted phenoxycarbonyl group, an optionally substituted benzoyloxy group, an optionally substituted phenylalkyl group, an optionally substituted naphthyl group, an optionally substituted naphthoxy group, an optionally substituted naphthoyl group, an optionally substituted naphthoxycarbonyl group, an optionally substituted naphthyloxy group, an optionally substituted naphthylalkyl group, an optionally substituted heterocyclyl group, an optionally substituted heterocyclylcarbonyl group, an amino group substituted with 1 or 2 organic groups, a morpholin-1-yl group, a piperazin-1-yl group, a halogen atom, a nitro group, a cyano group, and a substituent containing a group represented by HXC- or HXC- (wherein each X is independently a halogen atom).

[0276] R c5 When R is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 or more and 20 or less, and more preferably 1 or more and 6 or less. c5 When R is an alkyl group, it may be a straight chain or a branched chain. c5Specific examples of when R is an alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, an n-decyl group, and an isodecyl group. c5 When is an alkyl group, the alkyl group may contain an ether bond (-O-) in the carbon chain. Examples of alkyl groups having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.

[0277] R c5 When R is an alkoxy group, the number of carbon atoms in the alkoxy group is preferably 1 or more and 20 or less, and more preferably 1 or more and 6 or less. c5 When R is an alkoxy group, it may be a straight chain or a branched chain. c5 Specific examples of when R is an alkoxy group include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an isopentyloxy group, a sec-pentyloxy group, a tert-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, an isooctyloxy group, a sec-octyloxy group, a tert-octyloxy group, an n-nonyloxy group, an isononyloxy group, an n-decyloxy group, and an isodecyloxy group. c5 When is an alkoxy group, the alkoxy group may contain an ether bond (-O-) in the carbon chain. Examples of alkoxy groups having an ether bond in the carbon chain include a methoxyethoxy group, an ethoxyethoxy group, a methoxyethoxyethoxy group, an ethoxyethoxyethoxy group, a propyloxyethoxyethoxy group, and a methoxypropyloxy group.

[0278] R c5 When R is a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms in the cycloalkyl group or cycloalkoxy group is preferably 3 or more and 10 or less, and more preferably 3 or more and 6 or less. c5 Specific examples of R are cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. c5 Specific examples of when is a cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.

[0279] R c5 When R is a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, the saturated aliphatic acyl group or the saturated aliphatic acyloxy group preferably has 2 or more and 21 or less carbon atoms, more preferably 2 or more and 7 or less carbon atoms. c5 Specific examples of R are saturated aliphatic acyl groups include acetyl, propanoyl, n-butanoyl, 2-methylpropanoyl, n-pentanoyl, 2,2-dimethylpropanoyl, n-hexanoyl, n-heptanoyl, n-octanoyl, n-nonanoyl, n-decanoyl, n-undecanoyl, n-dodecanoyl, n-tridecanoyl, n-tetradecanoyl, n-pentadecanoyl, and n-hexadecanoyl groups. c5 Specific examples of when is a saturated aliphatic acyloxy group include an acetyloxy group, a propanoyloxy group, an n-butanoyloxy group, a 2-methylpropanoyloxy group, an n-pentanoyloxy group, a 2,2-dimethylpropanoyloxy group, an n-hexanoyloxy group, an n-heptanoyloxy group, an n-octanoyloxy group, an n-nonanoyloxy group, an n-decanoyloxy group, an n-undecanoyloxy group, an n-dodecanoyloxy group, an n-tridecanoyloxy group, an n-tetradecanoyloxy group, an n-pentadecanoyloxy group, and an n-hexadecanoyloxy group.

[0280] R c5 When R is an alkoxycarbonyl group, the alkoxycarbonyl group preferably has 2 or more and 20 or less carbon atoms, and more preferably has 2 or more and 7 or less carbon atoms. c5 Specific examples of when is an alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, a sec-butyloxycarbonyl group, a tert-butyloxycarbonyl group, an n-pentyloxycarbonyl group, an isopentyloxycarbonyl group, a sec-pentyloxycarbonyl group, a tert-pentyloxycarbonyl group, an n-hexyloxycarbonyl group, an n-heptyloxycarbonyl group, an n-octyloxycarbonyl group, an isooctyloxycarbonyl group, a sec-octyloxycarbonyl group, a tert-octyloxycarbonyl group, an n-nonyloxycarbonyl group, an isononyloxycarbonyl group, an n-decyloxycarbonyl group, and an isodecyloxycarbonyl group.

[0281] R c5 When R is a phenylalkyl group, the number of carbon atoms in the phenylalkyl group is preferably 7 or more and 20 or less, and more preferably 7 or more and 10 or less. c5 When R is a naphthylalkyl group, the naphthylalkyl group preferably has 11 or more and 20 or less carbon atoms, and more preferably has 11 or more and 14 or less carbon atoms. c5 Specific examples of R are phenylalkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl, and 4-phenylbutyl groups. c5 Specific examples of R are naphthylalkyl groups include α-naphthylmethyl, β-naphthylmethyl, 2-(α-naphthyl)ethyl, and 2-(β-naphthyl)ethyl. c5 is a phenyl alkyl group or a naphthyl alkyl group, R c5 may further have a substituent on the phenyl group or naphthyl group.

[0282] R c5 is a heterocyclyl group, the heterocyclyl group is c4 is a heterocyclyl group, and the heterocyclyl group may further have a substituent. R c5 When is a heterocyclylcarbonyl group, the heterocyclyl group contained in the heterocyclylcarbonyl group is R c5 is a heterocyclyl group.

[0283] R c5 is an amino group substituted with one or two organic groups, suitable examples of the organic group include an alkyl group having from 1 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, a saturated aliphatic acyl group having from 2 to 21 carbon atoms, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenylalkyl group having from 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoyl group which may have a substituent, a naphthylalkyl group having from 11 to 20 carbon atoms which may have a substituent, and a heterocyclyl group. Specific examples of these suitable organic groups include R c5 Specific examples of the amino group substituted with one or two organic groups include a methylamino group, an ethylamino group, a diethylamino group, an n-propylamino group, a di-n-propylamino group, an isopropylamino group, an n-butylamino group, a di-n-butylamino group, an n-pentylamino group, an n-hexylamino group, an n-heptylamino group, an n-octylamino group, an n-nonylamino group, an n-decylamino group, a phenylamino group, a naphthylamino group, an acetylamino group, a propanoylamino group, an n-butanoylamino group, an n-pentanoylamino group, an n-hexanoylamino group, an n-heptanoylamino group, an n-octanoylamino group, an n-decanoylamino group, a benzoylamino group, an α-naphthoylamino group, and a β-naphthoylamino group.

[0284] R c5When the phenyl group, naphthyl group, and heterocyclyl group contained in the formula (I) further have a substituent, examples of the substituent include a substituent containing a group represented by HX2C- or H2XC- (for example, a halogenated alkoxy group containing a group represented by HX2C- or H2XC-, a halogenated alkyl group containing a group represented by HX2C- or H2XC-), an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, a saturated aliphatic acyl group having from 2 to 7 carbon atoms, an alkoxycarbonyl group having from 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having from 2 to 7 carbon atoms, a monoalkylamino group having an alkyl group having from 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having from 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, a benzoyl group, a halogen, a nitro group, and a cyano group. c5 When the phenyl group, naphthyl group, and heterocyclyl group contained in R further have a substituent, the number of the substituents is not limited as long as it does not impair the object of the present invention, and is preferably 1 to 4. c5 When the phenyl group, naphthyl group, and heterocyclyl group contained in the above formula (I) have multiple substituents, the multiple substituents may be the same or different.

[0285] R c5 When the benzoyl group included in the formula (1) further has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, a 2-thenoyl group (thiophen-2-ylcarbonyl group), a furan-3-ylcarbonyl group, and a phenyl group.

[0286] Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, and a bromine atom, and a fluorine atom is preferred.

[0287] Examples of the substituent containing a group represented by HX2C- or H2XC- include a halogenated alkoxy group containing a group represented by HX2C- or H2XC-, a group having a halogenated alkoxy group containing a group represented by HX2C- or H2XC-, a halogenated alkyl group containing a group represented by HX2C- or H2XC-, and a group having a halogenated alkyl group containing a group represented by HX2C- or H2XC-, and more preferably a halogenated alkoxy group containing a group represented by HX2C- or H2XC-, or a group having a halogenated alkoxy group containing a group represented by HX2C- or H2XC-.

[0288] Examples of groups having a halogenated alkyl group containing a group represented by HX2C- or H2XC- include aromatic groups substituted with a halogenated alkyl group containing a group represented by HX2C- or H2XC- (e.g., phenyl group, naphthyl group, etc.), and cycloalkyl groups substituted with a halogenated alkyl group containing a group represented by HX2C- or H2XC- (e.g., cyclopentyl group, cyclohexyl group, etc.), and aromatic groups substituted with a halogenated alkyl group containing a group represented by HX2C- or H2XC- are preferred.

[0289] Examples of groups having a halogenated alkoxy group containing a group represented by HX2C- or H2XC- include aromatic groups substituted with a halogenated alkoxy group containing a group represented by HX2C- or H2XC- (e.g., phenyl, naphthyl, etc.), alkyl groups substituted with a halogenated alkoxy group containing a group represented by HX2C- or H2XC- (e.g., methyl, ethyl, n-propyl, i-propyl, etc.), and cycloalkyl groups substituted with a halogenated alkoxy group containing a group represented by HX2C- or H2XC- (e.g., cyclopentyl, cyclohexyl, etc.), and preferably aromatic groups substituted with a halogenated alkoxy group containing a group represented by HX2C- or H2XC-.

[0290] Also, R c5As the substituent, a cycloalkylalkyl group, a phenoxyalkyl group which may have a substituent on the aromatic ring, and a phenylthioalkyl group which may have a substituent on the aromatic ring are also preferred. The substituents which the phenoxyalkyl group and the phenylthioalkyl group may have are R c5 The substituents are the same as those that the phenyl group contained in

[0291] Among the monovalent organic groups, R c5 The alkyl group is preferably an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, a cycloalkylalkyl group, or a phenylthioalkyl group which may have a substituent on the aromatic ring. The alkyl group is preferably an alkyl group having from 1 to 20 carbon atoms, more preferably an alkyl group having from 1 to 8 carbon atoms, particularly preferably an alkyl group having from 1 to 4 carbon atoms, and most preferably a methyl group. Among the phenyl groups which may have a substituent, a methylphenyl group is preferred, and a 2-methylphenyl group is more preferred. The number of carbon atoms in the cycloalkylalkyl group contained in the cycloalkylalkyl group is preferably from 5 to 10, more preferably from 5 to 8, and particularly preferably 5 or 6. The number of carbon atoms in the alkylene group contained in the cycloalkylalkyl group is preferably from 1 to 8, more preferably from 1 to 4, and particularly preferably 2. Among the cycloalkylalkyl groups, a cyclopentylethyl group is preferred. The number of carbon atoms in the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring is preferably from 1 to 8, more preferably from 1 to 4, and particularly preferably 2. Among the phenylthioalkyl groups which may have a substituent on the aromatic ring, a 2-(4-chlorophenylthio)ethyl group is preferred.

[0292] In the group represented by formula (c3), R c5 There are multiple R c5 When R are bonded to each other to form a ring, the ring formed may be a hydrocarbon ring or a heterocyclic ring. Examples of heteroatoms contained in the heterocyclic ring include N, O, and S. c5The ring formed by bonding together is particularly preferably an aromatic ring. Such an aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Such an aromatic ring is preferably an aromatic hydrocarbon ring. In formula (c3), when a plurality of R c5 Specific examples of when these are bonded to each other to form a benzene ring are shown below.

[0293] [ka]

[0294] In the group represented by formula (c4), R c8 is a nitro group or a monovalent organic group. c8 is -(CO) on the fused ring in formula (c4). n1 In formula (c4), R is bonded to a 6-membered aromatic ring different from the aromatic ring bonded to the group represented by c8 The bonding position of R is not particularly limited. c8 When the compound represented by formula (c4) has a structure in which one or more R c8 It is preferable that one of the groups represented by formula (c4) is bonded to the 7-position of the fluorene skeleton. c8 When R has the formula (c4), the group represented by the formula (c4) is preferably represented by the following formula (c6): c8 If there are multiple, multiple R c8 may be the same or different.

[0295] [ka] (In formula (c6), R c6 , R c7 , R c8 , n3 are R in formula (c4), c6 , R c7 , R c8 , similar to n3.)

[0296] R c8 When R is a monovalent organic group, c8is not particularly limited as long as it does not impair the object of the present invention. As the organic group, a carbon atom-containing group is preferred, and a group consisting of one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 to 50, more preferably 1 to 20. R c8 is a monovalent organic group, R in formula (c3) c5 Suitable examples of the monovalent organic group as the aryl group include the same groups as those mentioned above.

[0297] In formula (c4), R c6 and R c7 R is a chain alkyl group which may have a substituent, a chain alkoxy group which may have a substituent, a cyclic organic group which may have a substituent, or a hydrogen atom. c6 and R c7 may be bonded to each other to form a ring. c6 and R c7 As R, a chain alkyl group which may have a substituent is preferred. c6 and R c7 When is a chain alkyl group which may have a substituent, the chain alkyl group may be a straight chain alkyl group or a branched chain alkyl group.

[0298] R c6 and R c7 When R is a chain alkyl group having no substituent, the number of carbon atoms in the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 6 or less. c6 and R c7 Specific examples of when R is a chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, an n-decyl group, and an isodecyl group.c6 and R c7 When is an alkyl group, the alkyl group may contain an ether bond (-O-) in the carbon chain. Examples of alkyl groups having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.

[0299] R c6 and R c7 When is a chain alkyl group having a substituent, the number of carbon atoms in the chain alkyl group is preferably 1 to 20, more preferably 1 to 10, and particularly preferably 1 to 6. In this case, the number of carbon atoms in the substituent is not included in the number of carbon atoms in the chain alkyl group. The chain alkyl group having a substituent is preferably linear.

[0300] The substituent that the alkyl group may have is not particularly limited as long as it does not impair the object of the present invention. Suitable examples of the substituent include an alkoxy group, a cyano group, a halogen atom, a halogenated alkyl group, a cyclic organic group, and an alkoxycarbonyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, and a bromine atom are preferred. Examples of the cyclic organic group include a cycloalkyl group, an aromatic hydrocarbon group, and a heterocyclyl group. Specific examples of the cycloalkyl group include R c8 The preferred examples are the same as those when R is a cycloalkyl group. Specific examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, and a phenanthryl group. Specific examples of the heterocyclyl group include R c8 The preferred examples are the same as those when R is a heterocyclyl group. c8 When is an alkoxycarbonyl group, the alkoxy group contained in the alkoxycarbonyl group may be linear or branched, preferably linear. The number of carbon atoms in the alkoxy group contained in the alkoxycarbonyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less.

[0301] When the chain alkyl group has a substituent, the number of the substituent is not particularly limited. The preferred number of the substituent varies depending on the number of carbon atoms of the chain alkyl group. The number of the substituent is typically 1 or more and 20 or less, preferably 1 or more and 10 or less, and more preferably 1 or more and 6 or less.

[0302] R c6 and R c7 When R is a chain alkoxy group having no substituent, the number of carbon atoms in the chain alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 6 or less. c6 and R c7 Specific examples of when R is a chain alkoxy group include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an isopentyloxy group, a sec-pentyloxy group, a tert-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, an isooctyloxy group, a sec-octyloxy group, a tert-octyloxy group, an n-nonyloxy group, an isononyloxy group, an n-decyloxy group, and an isodecyloxy group. c6 and R c7 When is an alkoxy group, the alkoxy group may contain an ether bond (-O-) in the carbon chain. Examples of alkoxy groups having an ether bond in the carbon chain include a methoxyethoxy group, an ethoxyethoxy group, a methoxyethoxyethoxy group, an ethoxyethoxyethoxy group, a propyloxyethoxyethoxy group, and a methoxypropyloxy group.

[0303] R c6 and R c7 When R is a chain alkoxy group having a substituent, the substituent that the alkoxy group may have is c6 and R c7 is a chain alkyl group.

[0304] R c6 and R c7When R is a cyclic organic group, the cyclic organic group may be an alicyclic group or an aromatic group. Examples of the cyclic organic group include an aliphatic cyclic hydrocarbon group, an aromatic hydrocarbon group, and a heterocyclyl group. c6 and R c7 When R is a cyclic organic group, the substituent that the cyclic organic group may have is R c6 and R c7 is a chain alkyl group.

[0305] R c6 and R c7 When is an aromatic hydrocarbon group, the aromatic hydrocarbon group is preferably a phenyl group, a group formed by multiple benzene rings bonded via carbon-carbon bonds, or a group formed by condensing multiple benzene rings. When the aromatic hydrocarbon group is a phenyl group or a group formed by bonding or condensing multiple benzene rings, the number of benzene rings contained in the aromatic hydrocarbon group is not particularly limited, and is preferably 3 or less, more preferably 2 or less, and particularly preferably 1. Specific preferred examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, and a phenanthryl group.

[0306] R c6 and R c7 When is an alicyclic hydrocarbon group, the alicyclic hydrocarbon group may be monocyclic or polycyclic. The number of carbon atoms in the alicyclic hydrocarbon group is not particularly limited, but is preferably 3 to 20, more preferably 3 to 10. Examples of monocyclic cyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, isobornyl, tricyclononyl, tricyclodecyl, tetracyclododecyl, and adamantyl.

[0307] R c6 and R c7 is a heterocyclyl group, R in formula (c3) c5 Examples of the heterocyclyl groups include the same groups as the heterocyclyl groups mentioned above.

[0308] R c6 and R c7 may be bonded to each other to form a ring. c6 and R c7 The group consisting of the ring formed by R is preferably a cycloalkylidene group. c6 and R c7 When these are bonded to form a cycloalkylidene group, the ring that constitutes the cycloalkylidene group is preferably a 5-membered or 6-membered ring, and more preferably a 5-membered ring.

[0309] R c7 When a ring is formed with the benzene ring of the fluorene skeleton, the ring may be an aromatic ring or an aliphatic ring.

[0310] R c6 and R c7 When the group formed by bonding is a cycloalkylidene group, the cycloalkylidene group may be fused with one or more other rings. Examples of rings that may be fused with the cycloalkylidene group include a benzene ring, a naphthalene ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring.

[0311] The above-described R c6 and R c7 Among these, preferred examples include groups of formula -A 1 -A 2 In the formula, A 1 is a straight chain alkylene group, and A 2 is an alkoxy group, a cyano group, a halogen atom, a halogenated alkyl group, a cyclic organic group, or an alkoxycarbonyl group.

[0312] A 1 The number of carbon atoms in the linear alkylene group is preferably 1 or more and 10 or less, and more preferably 1 or more and 6 or less. 2When A is an alkoxy group, the alkoxy group may be linear or branched, and is preferably linear. The number of carbon atoms in the alkoxy group is preferably 1 or more and 10 or less, and more preferably 1 or more and 6 or less. 2 When A is a halogen atom, it is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, more preferably a fluorine atom, a chlorine atom or a bromine atom. 2 When A is a halogenated alkyl group, the halogen atom contained in the halogenated alkyl group is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom. The halogenated alkyl group may be linear or branched, and is preferably linear. 2 When is a cyclic organic group, examples of the cyclic organic group include R c6 and R c7 The same applies to the cyclic organic group that A has as a substituent. 2 When is an alkoxycarbonyl group, examples of the alkoxycarbonyl group include R c6 and R c7 The alkoxycarbonyl group is the same as the alkoxycarbonyl group which the alkoxycarbonyl group has as a substituent.

[0313] R c6 and R c7Preferred specific examples of the alkyl group include alkyl groups such as an ethyl group, an n-propyl group, an n-butyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group; a 2-methoxyethyl group, a 3-methoxy-n-propyl group, a 4-methoxy-n-butyl group, a 5-methoxy-n-pentyl group, a 6-methoxy-n-hexyl group, a 7-methoxy-n-heptyl group, an 8-methoxy-n-octyl group, a 2-ethoxyethyl group, a 3-ethoxy-n-propyl group, alkoxyalkyl groups such as 2-cyanoethyl, 3-cyano-n-propyl, 4-cyano-n-butyl, 5-cyano-n-pentyl, 6-ethoxy-n-hexyl, 7-ethoxy-n-heptyl, and 8-ethoxy-n-octyl groups; cyanoalkyl groups such as 2-cyanoethyl, 3-cyano-n-propyl, 4-cyano-n-butyl, 5-cyano-n-pentyl, 6-cyano-n-hexyl, 7-cyano-n-heptyl, and 8-cyano-n-octyl groups; alkyl groups such as 2-phenylethyl, 3-phenyl-n-propyl, 4-phenyl-n-butyl, 5-phenyl-n-pentyl, 6-phenyl-n-hexyl, 7-phenyl-n-heptyl, and 8-phenyl-n-octyl groups; phenylalkyl groups such as 2-cyclohexylethyl, 3-cyclohexyl-n-propyl, 4-cyclohexyl-n-butyl, 5-cyclohexyl-n-pentyl, 6- cycloalkylalkyl groups such as a cyclohexyl-n-hexyl group, a 7-cyclohexyl-n-heptyl group, an 8-cyclohexyl-n-octyl group, a 2-cyclopentylethyl group, a 3-cyclopentyl-n-propyl group, a 4-cyclopentyl-n-butyl group, a 5-cyclopentyl-n-pentyl group, a 6-cyclopentyl-n-hexyl group, a 7-cyclopentyl-n-heptyl group, and an 8-cyclopentyl-n-octyl group;2-methoxycarbonylethyl group, 3-methoxycarbonyl-n-propyl group, 4-methoxycarbonyl-n-butyl group, 5-methoxycarbonyl-n-pentyl group, 6-methoxycarbonyl-n-hexyl group, 7-methoxycarbonyl-n-heptyl group, 8-methoxycarbonyl-n-octyl group, 2-ethoxycarbonylethyl group, 3-ethoxycarbonyl-n-propyl group, 4-ethoxycarbonyl-n-butyl group, 5-ethoxycarbonyl-n-pentyl group, 6-ethoxycarbonyl-n-hexyl group, 7-ethoxycarbonyl-n-heptyl group, and 8-ethoxycarbonyl-n-octyl group alkoxycarbonylalkyl groups such as 2-chloroethyl group, 3-chloro-n-propyl group, 4-chloro-n-butyl group, 5-chloro-n-pentyl group, 6-chloro-n-hexyl group, 7-chloro-n-heptyl group, 8-chloro-n-octyl group, 2-bromoethyl group, 3-bromo-n-propyl group, 4-bromo-n-butyl group, 5-bromo-n-pentyl group, 6-bromo-n-hexyl group, 7-bromo-n-heptyl group, 8-bromo-n-octyl group, 3,3,3-trifluoropropyl group, and 3,3,4,4,5,5,5-heptafluoro-n-pentyl group;

[0314] R c6 and R c7 Among the above, preferred groups are an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-methoxyethyl group, a 2-cyanoethyl group, a 2-phenylethyl group, a 2-cyclohexylethyl group, a 2-methoxycarbonylethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 3,3,3-trifluoropropyl group, and a 3,3,4,4,5,5,5-heptafluoro-n-pentyl group.

[0315] In the formula (c5), A is particularly preferably S, since this makes it easier to obtain a photopolymerization initiator with excellent sensitivity.

[0316] In formula (c5), R c9 is a monovalent organic group, a halogen atom, a nitro group, or a cyano group. R in formula (c5) c9When is a monovalent organic group, it can be selected from various organic groups as long as it does not impair the object of the present invention. As the organic group, a carbon atom-containing group is preferred, and a group consisting of one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 to 50, more preferably 1 to 20. In formula (c5), R c9 is an organic group, R in formula (c3) c5 Examples of the monovalent organic group include the same groups as those mentioned above.

[0317] R c9 Among these, a benzoyl group; a naphthoyl group; a benzoyl group substituted with a group selected from the group consisting of an alkyl group having from 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; a nitro group; and an optionally substituted benzofuranylcarbonyl group are preferred, and a benzoyl group; a naphthoyl group; a 2-methylphenylcarbonyl group; a 4-(piperazin-1-yl)phenylcarbonyl group; and a 4-(phenyl)phenylcarbonyl group are more preferred.

[0318] In formula (c5), n4 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1. When n4 is 1, R c9 The binding position of R c9 is preferably in the para position relative to the bond to the oxygen atom or sulfur atom.

[0319] In formulas (c1) and (c2), R c2 The monovalent organic group as is not particularly limited as long as it does not impair the object of the present invention. As the organic group, a carbon atom-containing group is preferred, and a group consisting of one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 to 50, more preferably 1 to 20. R c2 Suitable examples of the monovalent organic group as R in formula (c3) include c5 Specific examples of these groups include the monovalent organic groups represented by R c5 The groups are the same as those described above. Also, R c2 As the substituent, a cycloalkylalkyl group, a phenoxyalkyl group which may have a substituent on the aromatic ring, and a phenylthioalkyl group which may have a substituent on the aromatic ring are also preferred. The substituent that the phenoxyalkyl group and the phenylthioalkyl group may have is R in formula (c3). c5 The substituents are the same as those of the phenyl group, naphthyl group, and heterocyclyl group included in the above when they further have a substituent.

[0320] Among the organic groups, R c2 As the substituent, a substituent containing the group represented by HX2C- or H2XC-, an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, a cycloalkylalkyl group, or a phenylthioalkyl group which may have a substituent on the aromatic ring is preferred. With regard to the alkyl group, the phenyl group which may have a substituent, the number of carbon atoms in the cycloalkyl group contained in the cycloalkylalkyl group, the number of carbon atoms in the alkylene group contained in the cycloalkylalkyl group, the cycloalkylalkyl group, the number of carbon atoms in the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring, or the phenylthioalkyl group which may have a substituent on the aromatic ring, R in formula (c3) c5 is the same as:

[0321] Also, R c2 As for -A 3 -CO-OA 4 A group represented by the formula: 3 is a divalent organic group, preferably a divalent hydrocarbon group, and more preferably an alkylene group. 4 is a monovalent organic group, preferably a monovalent hydrocarbon group.

[0322] A 3When A is an alkylene group, the alkylene group may be linear or branched, and is preferably linear. 3 When is an alkylene group, the alkylene group preferably has 1 or more and 10 or less carbon atoms, more preferably 1 or more and 6 or less carbon atoms, and particularly preferably 1 or more and 4 or less carbon atoms.

[0323] A 4 Suitable examples of A include alkyl groups having 1 to 10 carbon atoms, aralkyl groups having 7 to 20 carbon atoms, and aromatic hydrocarbon groups having 6 to 20 carbon atoms. 4 Specific preferred examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, a phenyl group, a naphthyl group, a benzyl group, a phenethyl group, an α-naphthylmethyl group, and a β-naphthylmethyl group.

[0324] -A 3 -CO-OA 4

[0039] Specific preferred examples of the group represented by the formula (I) include a 2-methoxycarbonylethyl group, a 2-ethoxycarbonylethyl group, a 2-n-propyloxycarbonylethyl group, a 2-n-butyloxycarbonylethyl group, a 2-n-pentyloxycarbonylethyl group, a 2-n-hexyloxycarbonylethyl group, a 2-benzyloxycarbonylethyl group, a 2-phenoxycarbonylethyl group, a 3-methoxycarbonyl-n-propyl group, a 3-ethoxycarbonyl-n-propyl group, a 3-n-propyloxycarbonyl-n-propyl group, a 3-n-butyloxycarbonyl-n-propyl group, a 3-n-pentyloxycarbonyl-n-propyl group, a 3-n-hexyloxycarbonyl-n-propyl group, a 3-benzyloxycarbonyl-n-propyl group, and a 3-phenoxycarbonyl-n-propyl group.

[0325] Also, R c2 As the group, groups represented by the following formula (c7) or (c8) are also preferred. [ka] (In formulas (c7) and (c8), R c10 and R c11 are each independently a monovalent organic group, n5 is an integer between 0 and 4, R c10 and R c11 When R is located at adjacent positions on the benzene ring, c10 and R c11 and may be bonded to each other to form a ring, R c12 is a monovalent organic group, n6 is an integer between 1 and 8, n7 is an integer between 1 and 5, n8 is an integer between 0 and (n7+3) inclusive.)

[0326] R in formula (c7) c10 and R c11 The organic group represented by R in formula (c4) c8 Similar to R c10 As R, a halogenated alkoxy group containing a group represented by HX2C- or H2XC-, a halogenated alkyl group containing a group represented by HX2C- or H2XC-, an alkyl group, or a phenyl group is preferred. c10 and R c11 When R is bonded to form a ring, the ring may be an aromatic ring or an aliphatic ring. c10 and R c11 Suitable examples of the group in which and form a ring include a naphthalen-1-yl group and a 1,2,3,4-tetrahydronaphthalen-5-yl group. In the above formula (c7), n7 is an integer of 0 or more and 4 or less, preferably 0 or 1, and more preferably 0.

[0327] In the above formula (c8), R c12 is an organic group. As the organic group, R in formula (c4) c8Examples of the organic groups include the same groups as those described for the organic groups. Among the organic groups, alkyl groups are preferred. The alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and particularly preferably 1 to 3. R c12 Preferred examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group, and among these, a methyl group is more preferred.

[0328] In the above formula (c8), n7 is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 3 or less, and more preferably 1 or 2. In the above formula (c8), n8 is 0 or more and (n7+3) or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0. In the above formula (c8), n8 is an integer of 1 or more and 8 or less, preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1 or 2.

[0329] In formula (c2), R c3 R is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aryl group which may have a substituent. c3 When is an aliphatic hydrocarbon group, the substituent that may be substituted therewith is preferably a phenyl group, a naphthyl group, or the like.

[0330] In formulas (c1) and (c2), R c3 Preferred examples of the alkyl group include a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a 2-cyclopentylethyl group, a 2-cyclobutylethyl group, a cyclohexylmethyl group, a phenyl group, a benzyl group, a methylphenyl group, and a naphthyl group, and among these, a methyl group or a phenyl group is more preferred.

[0331] Represented by formula (c2), and R c1 Specific preferred examples of the compound having a group represented by formula (c3) include the following compounds: [ka]

[0332] [ka]

[0333] [ka]

[0334] [ka]

[0335] Represented by formula (c2), and R c1 Specific preferred examples of the compound having a group represented by formula (c4) include the following compounds: [ka]

[0336] [ka]

[0337] [ka]

[0338] [ka]

[0339] [ka]

[0340] Represented by formula (c2), and R c1 Specific preferred examples of the compound having a group represented by formula (c5) include the following compounds: [ka]

[0341] As the radical polymerization initiator (C1), a phosphine oxide compound is also preferred because it provides good deep curing properties for the photosensitive composition. As the phosphine oxide compound, a phosphine oxide compound containing a partial structure represented by the following formula (c9) is preferred. [ka] In formula (c9), R c21 and R c22 are each independently an alkyl group, a cycloalkyl group, an aryl group, an aliphatic acyl group having from 2 to 20 carbon atoms, or an aromatic acyl group having from 7 to 20 carbon atoms, provided that R c21 and R c22 are not both an aliphatic acyl group or an aromatic acyl group.

[0342] R c21 and R c22 The number of carbon atoms in the alkyl group represented by R is preferably 1 or more and 12 or less, more preferably 1 or more and 8 or less, and even more preferably 1 or more and 4 or less. c21 and R c22 The alkyl group may be linear or branched. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, a 2,4,4-trimethylpentyl group, a 2-ethylhexyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, and an n-dodecyl group.

[0343] R c21 and R c22The number of carbon atoms in the cycloalkyl group is preferably 5 or more and 12 or less. Specific examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cycloundecyl group, and a cyclododecyl group.

[0344] R c21 and R c22 The number of carbon atoms in the aryl group as the aryl group is preferably 6 or more and 12 or less. The aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. Specific examples of the aryl group include a phenyl group and a naphthyl group.

[0345] R c21 and R c22 The number of carbon atoms in the aliphatic acyl group as the alkyl group is from 2 to 20, preferably from 2 to 12, more preferably from 2 to 8, and even more preferably from 2 to 6. The aliphatic acyl group may be linear or branched. Specific examples of the aliphatic acyl group include an acetyl group, a propionyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, a tridecanoyl group, a tetradecanoyl group, a pentadecanoyl group, a hexadecanoyl group, a heptadecanoyl group, an octadecanoyl group, a nonadecanoyl group, and an icosanoyl group.

[0346] R c21 and R c22The aromatic acyl group as the aromatic acyl group has 7 or more and 20 or less carbon atoms. The aromatic acyl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. Specific examples of the aromatic acyl group include a benzoyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,6-dimethylbenzoyl group, a 2,6-dimethoxybenzoyl group, a 2,4,6-trimethylbenzoyl group, an α-naphthoyl group, and a β-naphthoyl group.

[0347] Preferred specific examples of the phosphine oxide compound containing a structural moiety represented by formula (c9) include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide. From the viewpoint of deep curing properties of the photosensitive composition, it is also preferable that the phosphine oxide compound containing the structural moiety represented by formula (c9) is used together with an α-hydroxyalkylphenone initiator such as 2-hydroxy-2-methylpropiophenone. When a phosphine oxide compound having a structural moiety represented by formula (c9) is used in combination with an α-hydroxyalkylphenone initiator such as 2-hydroxy-2-methylpropiophenone, the ratio of the mass of the phosphine oxide compound having a structural moiety represented by formula (c9) to the total mass of both is preferably 20% by mass or more and 80% by mass or less, more preferably 30% by mass or more and 70% by mass or less, and even more preferably 40% by mass or more and 60% by mass or less.

[0348] As the cationic polymerization initiator (C2), any known cationic polymerization initiator can be used without any particular limitation. Typical examples of the cationic polymerization initiator (C2) include onium salts. Examples of the cationic polymerization initiator (C2) include oxonium salts, ammonium salts, phosphonium salts, sulfonium salts, and iodonium salts, with sulfonium salts and iodonium salts being preferred, and sulfonium salts being more preferred.

[0349] The content of the initiator (C) in the photosensitive composition is not particularly limited and is determined appropriately depending on the type of the radical polymerizable group or the cation polymerizable group and the type of the initiator (C). The content of the initiator (C) in the photosensitive composition is preferably 0.01 parts by mass or more and 20 parts by mass or less, more preferably 0.1 parts by mass or more and 15 parts by mass or less, and even more preferably 1 part by mass or more and 10 parts by mass or less, when the mass of the photosensitive composition excluding the mass of the solvent (S) described below is taken as 100 parts by mass.

[0350] The photosensitive composition can be obtained by uniformly mixing and dispersing the photopolymerizable compound (A), inorganic fine particles (B), initiator (C), and optional components that are blended as needed in desired amounts.

[0351] <Method for producing cured product> The photosensitive composition described above is molded into a desired shape, and then the photosensitive composition is exposed to light depending on the type of initiator (C), thereby producing a cured product.

[0352] The method for molding the photosensitive composition is not particularly limited and may be appropriately selected depending on the shape of the cured product. Examples of the molding method include coating and casting into a mold. Hereinafter, a method for producing a cured film will be described as a representative example of a method for producing a cured product.

[0353] First, the photosensitive composition is applied onto a desired substrate to form a coating film, and then, if necessary, at least a part of the solvent (S) is removed from the coating film to form a coating film.

[0354] The method for applying the photosensitive composition onto a substrate is not particularly limited. For example, the curable composition can be applied to a substrate to a desired film thickness using a contact transfer type coating device such as a roll coater, a reverse coater, a bar coater, or a slit coater, or a non-contact type coating device such as a spinner (rotary coating device) or a curtain flow coater, to form a coating film. Furthermore, printing methods such as screen printing and inkjet printing can also be used to form the coating film. As described above, the photosensitive composition is unlikely to dry rapidly, thicken, or solidify in an inkjet head. Therefore, by using the photosensitive composition, coating by inkjet printing can be performed satisfactorily.

[0355] After the photosensitive composition is applied to a substrate, the coating film is preferably baked as needed to remove at least a portion of the solvent (S) from the coating film. The baking temperature is appropriately determined taking into consideration the boiling point of the solvent (S), etc. Baking may be performed at a low temperature under reduced pressure.

[0356] The baking method is not particularly limited, and examples thereof include a method of drying using a hot plate at a temperature of 80° C. to 150° C., preferably 85° C. to 120° C., for 60 to 500 seconds.

[0357] The thickness of the coating film formed as described above is not particularly limited. The thickness of the coating film is appropriately determined depending on the application of the cured film. The thickness of the coating film is typically adjusted appropriately so that a cured film having a thickness of preferably 0.1 μm or more and 10 μm or less, more preferably 0.2 μm or more and 5 μm or less, is formed.

[0358] After forming a coating film by the above method, the coating film can be exposed to light to obtain a cured film.

[0359] The conditions for exposing the coating film are not particularly limited as long as the curing proceeds well. The exposure is carried out by irradiating the coating film with active energy rays such as ultraviolet light or excimer laser light. The amount of energy radiation to be irradiated is not particularly limited, but is, for example, 30 mJ / cm. 2 More than 5000mJ / cm 2 After exposure, the exposed coating film may be baked in the same manner as in the heating after coating. [Example]

[0360] The present invention will be described in more detail below with reference to examples, but the scope of the present invention is not limited to these examples.

[0361] [Synthesis Example 1] A 300 mL reactor was charged with 4,4'-thiobisbenzenethiol (20.0 g, 0.080 mol) and 100 mL of 20% aqueous sodium hydroxide solution. After replacing the atmosphere in the reactor with nitrogen, the contents of the reactor were stirred at an internal temperature of 60°C for 30 minutes. Then, 1-chloro-3-ethoxy-2-propanol (25.5 g, 0.186 mol) was added dropwise to the reactor, and the reaction was carried out at an internal temperature of 90°C for 4 hours. The reaction solution was then cooled to room temperature while stirring. The solid precipitated upon cooling was collected by filtration and washed with water. The resulting solid was dried under reduced pressure to obtain 36.2 g of compound IM1 (yield: 99%). Next, in a 500 mL reactor, compound IM1 (36.2 g, 0.079 mol), triethylamine (19.3 g, 0.191 mol), hydroquinone (0.88 g, 0.008 mol), and 360 mL of tetrahydrofuran were mixed. The resulting solution was cooled in an ice bath. Acryloyl chloride (17.3 g, 0.191 mol) was added dropwise to the cooled solution while maintaining the internal temperature at 5°C or below. The solution containing acrylic acid chloride was stirred at room temperature for 2 hours, and then the precipitated salt was filtered. The solvent was removed from the resulting filtrate using an evaporator to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography to obtain 24.5 g (yield 55%) of compound 1 as a colorless liquid. 1 The results of H-NMR measurements are as follows: 1 H-NMR (DMSO): 1.05(t, 6H), 2.95(dd, 4H), 3.65(dd, 4H), 3.88(q, 4H), 5.17(m, 2H), 5.83(dd, 2H), 6.12(dd, 2H), 6.41(dd, 2H), 7.16(d, 4H), 7.28(d, 4H) [ka]

[0362] [Synthesis Example 2] A 300 mL reactor was charged with 4,4'-thiobisbenzenethiol (20.0 g, 0.080 mol) and 100 mL of 20% aqueous sodium hydroxide solution. After replacing the atmosphere in the reactor with nitrogen, the contents of the reactor were stirred for 30 minutes at an internal temperature of 60°C. Ethylene glycol mono-2-chloroethyl ether (23.2 g, 0.186 mol) was then added dropwise to the reactor, and the reaction was carried out at an internal temperature of 90°C for 4 hours. The reaction solution was then cooled to room temperature while stirring. The precipitated solid was collected by filtration and washed with water. The resulting solid was dried under reduced pressure to obtain 33.8 g of compound IM2 (yield: 99%). Next, in a 500 mL reactor, compound IM2 (33.8 g, 0.079 mol), triethylamine (19.2 g, 0.190 mol), hydroquinone (0.87 g, 0.008 mol), and 340 mL of tetrahydrofuran were mixed. The resulting solution was cooled in an ice bath. Acryloyl chloride (17.2 g, 0.190 mol) was added dropwise to the cooled solution while maintaining the internal temperature at 5°C or below. The solution containing acrylic acid chloride was stirred at room temperature for 2 hours, and then the precipitated salt was filtered. The solvent was removed from the resulting filtrate using an evaporator to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography to obtain 22.1 g (yield 52%) of compound 2 as a colorless liquid. 1 The results of H-NMR measurements are as follows: 1H-NMR (DMSO): 3.27(t, 4H), 3.63(t, 4H), 3.77(t, 4H), 4.27(t, 4H), 5.80(dd, 2H), 6.15(dd, 2H), 6.41(dd, 2H), 7.20(d, 4H), 7.28(d, 4H) [ka]

[0363] [Synthesis Example 3] A 300 mL reactor was charged with 4,4'-thiobisbenzenethiol (20.0 g, 0.080 mol) and 100 mL of 20% aqueous sodium hydroxide solution. After replacing the atmosphere inside the reactor with nitrogen, the contents were stirred at an internal temperature of 60°C for 30 minutes. 2-[2-(2-chloroethoxy)ethoxy]ethanol (31.4 g, 0.186 mol) was then added dropwise to the reactor, and the reaction was carried out at an internal temperature of 90°C for 4 hours. The reaction solution was then cooled to room temperature with stirring. Water was added to the cooled reaction solution, and toluene was then added to the reaction solution to extract the product into toluene. The solvent was removed from the separated toluene layer, and the residue after solvent removal was purified by silica gel chromatography to obtain 34.1 g of compound IM3 (yield 83%). Next, in a 500 mL reactor, compound IM3 (34.1 g, 0.079 mol), triethylamine (16.1 g, 0.159 mol), hydroquinone (0.73 g, 0.007 mol), and 340 mL of tetrahydrofuran were mixed. The resulting solution was cooled in an ice bath. Acryloyl chloride (14.4 g, 0.159 mol) was added dropwise to the cooled solution while maintaining the internal temperature at 5°C or below. The solution containing acrylic acid chloride was stirred at room temperature for 2 hours, and then the precipitated salt was filtered. The solvent was removed from the resulting filtrate using an evaporator to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography to obtain 18.9 g (46% yield) of compound 3 as a colorless liquid. 1 The results of H-NMR measurements are as follows: 1H-NMR (DMSO): 3.27(t, 4H), 3.50(s, 8H), 3.63(t, 4H), 3.80(t, 4H), 4.30(t, 4H), 5.80(dd, 2H), 6.15(dd, 2H), 6.41(dd, 2H), 7.20(d, 4H), 7.28(d, 4H) [ka]

[0364] [Synthesis Example 4] A 300 mL reactor was charged with 4,4'-thiobisbenzenethiol (20.0 g, 0.080 mol) and 100 mL of 20% aqueous sodium hydroxide solution. After replacing the atmosphere inside the reactor with nitrogen, the contents were stirred for 30 minutes at an internal temperature of 60°C. 3-(3-chloropropoxy)propan-1-ol (28.5 g, 0.186 mol) was then added dropwise to the reactor, and the reaction was carried out at an internal temperature of 90°C for 4 hours. The reaction mixture was then cooled to room temperature with stirring. Water was added to the cooled reaction mixture, and toluene was then added to the reaction mixture to extract the product into toluene. The solvent was removed from the separated toluene layer, and the residue after solvent removal was purified by silica gel chromatography to obtain 36.5 g of compound IM4 (yield 98%). Next, in a 500 mL reactor, compound IM4 (36.5 g, 0.073 mol), triethylamine (17.8 g, 0.176 mol), hydroquinone (0.81 g, 0.007 mol), and 360 mL of tetrahydrofuran were mixed. The resulting solution was cooled in an ice bath. Acryloyl chloride (15.9 g, 0.176 mol) was added dropwise to the cooled solution while maintaining the internal temperature at 5°C or below. The solution containing acrylic acid chloride was stirred at room temperature for 2 hours, and then the precipitated salt was filtered. The solvent was removed from the resulting filtrate using an evaporator to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography to obtain compound 4 as a colorless liquid in an amount of 22.6 g (yield: 54%). 1 The results of H-NMR measurements are as follows: 1H-NMR (DMSO): 1.86 (m, 8H), 2.94 (t, 4H), 3.35 (t, 8H), 4.20 (t, 4H), 5.80 (dd, 2H), 6.15 (dd, 2H), 6.41 (dd, 2H), 7.20 (d, 4H), 7.28 (d, 4H) [ka]

[0365] [Synthesis Example 5] A 300 mL reactor was charged with 4,4'-dihydroxydiphenyl sulfide (20.0 g, 0.092 mol), potassium carbonate (38.0 g, 0.275 mol), ethylene glycol mono-2-chloroethyl ether (27.4 g, 0.220 mol), and 200 mL of dimethylformamide. After purging the reactor with nitrogen, the reaction mixture was stirred at an internal temperature of 90°C for 10 hours. The reaction mixture was then cooled to room temperature with stirring. Water was added to the cooled reaction mixture, and toluene was then added to extract the product into toluene. The solvent was removed from the separated toluene layer, and the residue after solvent removal was purified by silica gel chromatography to obtain 42.3 g of compound IM5 (yield 86%). Next, in a 300 mL reactor, compound IM5 (42.3 g, 0.079 mol), triethylamine (19.2 g, 0.190 mol), hydroquinone (0.87 g, 0.008 mol), and 420 mL of tetrahydrofuran were mixed. The resulting solution was cooled in an ice bath. Acryloyl chloride (17.2 g, 0.190 mol) was added dropwise to the cooled solution while maintaining the internal temperature at 5°C or below. The solution containing added acrylic acid chloride was stirred at room temperature for 2 hours, and then the precipitated salt was filtered. The solvent was removed from the resulting filtrate using an evaporator to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography to obtain 22.6 g (yield 53%) of compound 5 as a colorless liquid. 1 The results of H-NMR measurements are as follows: 1H-NMR (DMSO): 3.63(t, 4H), 3.77(t, 4H), 4.31(m, 8H), 5.80(dd, 2H), 6.15(dd, 2H), 6.41(dd, 2H), 7.20(d, 4H), 7.28(d, 4H) [ka]

[0366] [Synthesis Example 6] A 300 mL reactor was charged with 4,4'-dihydroxydiphenyl sulfide (20.0 g, 0.092 mol), potassium carbonate (38.0 g, 0.275 mol), 2-[2-(2-chloroethoxy)ethoxy]ethanol (37.1 g, 0.220 mol), and 200 mL of dimethylformamide. After purging the reactor with nitrogen, the reaction mixture was stirred at an internal temperature of 90°C for 10 hours. The reaction mixture was then cooled to room temperature with stirring. Water was added to the cooled reaction mixture, and toluene was then added to extract the product into toluene. The solvent was removed from the separated toluene layer, and the residue was purified by silica gel chromatography to obtain 35.7 g of compound IM6 (76% yield). Next, in a 300 mL reactor, compound IM6 (35.7 g, 0.069 mol), triethylamine (16.8 g, 0.190 mol), hydroquinone (0.76 g, 0.007 mol), and 360 mL of tetrahydrofuran were mixed. The resulting solution was cooled in an ice bath. Acryloyl chloride (15.1 g, 0.166 mol) was added dropwise to the cooled solution while maintaining the internal temperature at 5°C or below. The solution containing acrylic acid chloride was stirred at room temperature for 2 hours, and then the precipitated salt was filtered. The solvent was removed from the resulting filtrate using an evaporator to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography to obtain 24.2 g (yield 56%) of compound 6 as a colorless liquid. 1 The results of H-NMR measurements are as follows: 1H-NMR(DMSO): 3.52(s, 8H), 3.63(t, 4H), 3.70(t, 4H), 4.30(m, 8H), 5.80(dd, 2H), 6.15(dd, 2H), 6.41(dd, 2H), 7.20(d, 4H), 7.28(d, 4H) [ka]

[0367] [Examples 1 to 12, Comparative Examples 1 and 2] A simulation test was carried out by heating a photosensitive composition using compounds 1 to 6 obtained in the above Synthesis Examples 1 to 6 and 2-(2-acryloyloxyethyl)oxybiphenyl as a comparative compound. Note that the inorganic fine particles (B) and the initiator (C) do not affect the weight loss caused by heating at 110°C. Specifically, 150 mg of the photopolymerizable compound (A) of the type shown in Table 1 was dissolved in the solvent (S) of the type shown in Table 1 so that the solid content concentration was 10 mass % to obtain a solution containing the photopolymerizable compound (A). As the solvent (S), the following S-1 and S-2 were used. S-1: Propylene glycol monomethyl ether acetate S-2: HO-(CH2CH2CH2-O)2-CH3 (dipropylene glycol monomethyl ether)

[0368] The resulting solution was dropped onto a weighed glass substrate, heated at 110°C for 10 minutes, and the glass substrate was then weighed again. The mass of the photopolymerizable compound (A) lost by heating was calculated from the weight of the glass substrate before and after heating. The mass loss rate of the photopolymerizable compound (A) due to heating was calculated from the mass loss rate of the photopolymerizable compound (A) lost by heating. The loss rate values ​​are shown in Table 1.

[0369] [Table 1]

[0370] Comparison of Examples 1 to 12 with Comparative Examples 1 and 2 reveals that in the composition containing the photopolymerizable compound (A) having a structure included in the aforementioned formula (A1), the loss of weight raw materials of components other than the solvent (S) due to heating is significantly suppressed compared to the composition containing the photopolymerizable compound having a structure that does not correspond to the structure of the aforementioned formula (A1).

[0371] [Examples 13 to 60 and Comparative Examples 3 to 10] Five parts by mass of a photopolymerizable compound (A) of the type shown in Tables 2 and 3, 20 parts by mass of inorganic fine particles (B) made of the material shown in Tables 2 and 3, and 0.5 parts by mass of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide as an initiator (C) were dissolved and dispersed in a solvent (S) of the type shown in Tables 2 and 3 so that the solid concentration was 10% by mass, thereby obtaining photosensitive compositions of Examples 13 to 60 and Comparative Examples 3 to 10. The gold particles, platinum particles, zirconium oxide particles, and titanium oxide particles used as the inorganic particles (B) all had an average particle size of 10 nm. As the zirconium oxide particles and titanium oxide particles, surface-treated zirconium oxide particles and surface-treated titanium oxide particles were used. The obtained photosensitive composition was left to stand in a thermostatic chamber at 40°C for 3 months, and the dispersion state of the inorganic fine particles in the photosensitive composition was visually inspected after 1 month and after 3 months, and the dispersion stability of the inorganic fine particles (B) in the photosensitive composition was evaluated according to the following criteria. ◯: No separation or sedimentation of inorganic fine particles (B) occurred. △: Slight separation or sedimentation of inorganic fine particles (B) was observed. ×: Significant separation or sedimentation of the inorganic fine particles (B) was observed.

[0372] [Table 2]

[0373] [Table 3]

[0374] A comparison between Examples 13 to 60 and Comparative Examples 3 to 10 reveals that in the photosensitive composition containing the photopolymerizable compound (A) having a structure included in the aforementioned formula (A1), the inorganic fine particles (B) are stably dispersed for a long period of time, such as 3 months, at 40°C, whereas in the photosensitive composition containing the photopolymerizable compound having a structure other than that of the aforementioned formula (A1), the inorganic fine particles (B) separate or settle out after 3 months of storage at 40°C.

[0375] [Examples 61 to 66, Comparative Examples 11 and 12] 2.3 parts by mass of photopolymerizable compound (A) of the type shown in Table 4, 7.5 parts by mass of titanium oxide microparticles as inorganic microparticles (B), and 0.2 parts by mass of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide as initiator (C) were dispersed and dissolved in the aforementioned solvent S-1 (propylene glycol monomethyl ether acetate) so that the ratio of the total mass of the photopolymerizable compound (A), inorganic microparticles (B), and initiator (C) to the mass of the photosensitive composition was 10 mass%, thereby obtaining the photosensitive compositions of Examples 61 to 66, Comparative Example 11, and Comparative Example 12. For the photopolymerizable compound (A), 2-(2-acryloyloxyethyl)oxybiphenyl was used as comparative compound 1. As comparative compound 2, 4,4'-bis(2-methacryloyloxyethyl)oxydiphenyl sulfide was used. The obtained photosensitive compositions were used to evaluate the transmittance, surface appearance, and heat resistance of the cured films according to the following methods. The evaluation results are shown in Table 4.

[0376] <Transmittance evaluation of cured film> The photosensitive composition was applied onto a glass substrate using a spin coater. Then, the film made of the photosensitive composition was heated at 110°C for 2 minutes to obtain a coating film having a thickness sufficient to form a cured film with a thickness of 0.3 µm. The obtained coating film was exposed to an accumulated exposure dose of 100 mJ / cm using a high-pressure mercury lamp. 2The exposed coating film was heated at 110° C. for 2 minutes to obtain a cured film having a thickness of 0.3 μm. The light transmittance of the obtained cured film was measured using a multichannel spectrometer (MCPD-3000) manufactured by Otsuka Electronics Co., Ltd., and the average transmittance of light having a wavelength of 400 to 700 nm was determined.

[0377] <Evaluation of surface appearance> The surface of the cured film formed in the same manner as in the transmittance measurement was observed under an optical microscope. Based on the results of the optical microscope observation, the surface appearance of the cured product was evaluated according to the following criteria. ◯: No roughness or cracks are observed on the surface. ×: Roughness or cracks are observed on the surface.

[0378] <Evaluation of heat resistance> The average transmittance of light having a wavelength of 400 to 700 nm determined in the transmittance evaluation of the cured film above was designated as T0. The cured film was then heated at 180°C for 2 minutes. After heating, the average transmittance of the cured film having a wavelength of 400 to 700 nm was measured at the same position as that where the average transmittance T0 was measured, and designated as T1. The transmittance change rate was calculated based on the measured values ​​of T0 and T1 according to the following formula: Transmittance change rate (%) = |(T1-T0) / T0×100| The heat resistance of the cured product was evaluated from the obtained rate of change in transmittance according to the following criteria. ◯: The rate of change in transmittance is less than 1%. ×: The rate of change in transmittance is 1% or more.

[0379] [Table 4]

[0380] A comparison of Examples 61 to 66 with Comparative Examples 11 and 12 reveals that photosensitive compositions containing a photopolymerizable compound (A) having a structure within the aforementioned formula (A1) give cured products that are excellent in all of light transmittance, surface appearance, and heat resistance, whereas photosensitive compositions containing a photopolymerizable compound having a structure that does not correspond to the structure of the aforementioned formula (A1) give cured products that are poor in surface appearance and heat resistance.

Claims

1. A photopolymerizable compound (A) and inorganic fine particles (B), The photopolymerizable compound (A) 【Chemistry 1】 , or 【Chemistry 2】 The composition.

2. The composition according to claim 1, wherein the inorganic fine particles (B) are one or more selected from the group consisting of metal oxide fine particles (B1) and metal fine particles (B2).

3. The composition contains a photopolymerizable compound (A), inorganic fine particles (B), and an initiator (C), The photopolymerizable compound (A) 【Transformation 3】 , or 【Chemistry 4】 The photosensitive composition according to claim 1,

4. A cured product of the photosensitive composition according to claim 3.

5. A compound represented by the following formula: 【Transformation 5】 , or 【Transformation 6】

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