Composition, cured product, and optical member

JP2025145664APending Publication Date: 2025-10-03FUJIFILM CORP
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Patent Information

Application Number
JP2024045960
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-03-22
Publication Date
2025-10-03

AI Technical Summary

Technical Problem

Existing benzobisdithiol compounds in compositions do not adequately address the issues of haze and light resistance in cured products, limiting their application in optical components.

Method used

A composition comprising a compound represented by formula (1) and a curable compound, including a resin, which enhances light resistance and reduces haze in cured products by utilizing a benzobisdithiol skeleton with an asymmetric structure and a polymerizable group, forming a cured product with improved compatibility and stability.

Benefits of technology

The composition produces cured products with enhanced light resistance and reduced haze, suitable for optical components by suppressing decomposition and surface precipitation, thereby improving performance.

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Patent Text Reader

Abstract

To provide a composition having superior light resistance and allowing formation of a cured product with reduced haze; a cured product; and an optical member.SOLUTION: A composition comprising a compound represented by formula (1) and a curable compound. In formula (1), Q1 represents a group represented by formula (Q-1); Q2 represents =CRq2Rq3 or the like; and R1 represents -O-Y11 or the like. Also provided are a cured product and an optical member produced using the composition.SELECTED DRAWING: None
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Description

[Technical Field]

[0001] The present invention relates to a composition containing a benzobisdithiol compound. The present invention also relates to a cured product and an optical component using the composition containing the benzobisdithiol compound. [Background technology]

[0002] Benzobisdithiol compounds have excellent ultraviolet absorption properties and are used as ultraviolet absorbers, etc. For example, Patent Document 1 describes the use of a specific benzobisdithiol as an ultraviolet absorber. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-209126 Summary of the Invention [Problem to be solved by the invention]

[0004] The present inventors have conducted extensive research into compositions containing benzobisdithiol compounds and have found that there is room for further improvement in the haze and light resistance of the resulting cured products.

[0005] Therefore, an object of the present invention is to provide a composition from which a cured product having excellent light resistance and reduced haze can be produced, and to provide a cured product and an optical component. [Means for solving the problem]

[0006] The present invention provides the following:

[0007] <1> A composition comprising a compound represented by formula (1) and a curable compound; [ka] In formula (1), Q 1 represents a group represented by formula (Q-1); Q 2 are =O, =S, and =NR q1 or =CR q2 R q3 represents R q1 ~R q3 each independently represents a hydrogen atom or a substituent, R q2 and R q3 may be linked together to form a ring; R 1 -OY 11 , -OC(=O)-Y 11 , -OC(=O)OY 11 , -OC(=O)NR y11 -Y 11 , -OSO2-Y 11 or a group containing a polymerizable group having an ethylenically unsaturated bond, R y11 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group; Y 11 represents an alkyl group, an aralkyl group, or an aryl group; [ka] In formula (Q-1), * represents a bond, and R 101 and R 102 each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond. <2> R in the above formula (1) 1 -OY 11 and Y 11 is an alkyl group, an aralkyl group, or an aryl group, <1> The composition described in <3> Above Y 11 is an alkyl group having 2 to 30 carbon atoms, <2> The composition described in <4> Q in the above formula (1) 2 is =CR q2 R q3 That is, <1> or <2> The composition described in <5> The curable compound includes at least one selected from a resin and a polymerizable compound. <1> ~ <4> The composition according to any one of the preceding claims. <6> The curable compound contains a resin, and the resin is at least one selected from a (meth)acrylic resin, a polystyrene resin, a polyester resin, a polyurethane resin, a thiourethane resin, a polyimide resin, an epoxy resin, a polycarbonate resin, a phthalate resin, a cellulose acylate resin, and a cyclic olefin resin. <1> ~ <5> The composition according to any one of the preceding claims. <7> <1> ~ <6> A cured product obtained by using the composition according to any one of the above items. <8> <7> An optical component comprising the cured product according to claim 1. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a composition that can produce a cured product having excellent light resistance and reduced haze. The present invention also provides a cured product and an optical component. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will be described in detail below. In the description of groups (atomic groups) in this specification, when a notation does not specify whether they are substituted or unsubstituted, it encompasses both unsubstituted and substituted groups. For example, the term "alkyl group" encompasses not only unsubstituted alkyl groups (unsubstituted alkyl groups) but also substituted alkyl groups (substituted alkyl groups). In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In this specification, the total solid content refers to the total amount of all components of the composition excluding the solvent. In this specification, "(meth)acrylate" refers to either or both of acrylate and methacrylate, "(meth)acrylic" refers to either or both of acrylic and methacrylic, "(meth)allyl" refers to either or both of allyl and methallyl, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl. In this specification, the term "process" does not only mean an independent process, but also includes a process that cannot be clearly distinguished from other processes as long as the intended effect of the process is achieved. In this specification, the weight average molecular weight (Mw) and number average molecular weight (Mn) are defined as values ​​calculated in terms of polystyrene measured by gel permeation chromatography (GPC).

[0010] <Composition> The composition of the present invention is characterized by containing a compound represented by formula (1) and a curable compound.

[0011] According to the present invention, it is possible to produce a cured product having excellent light resistance and reduced haze. The reason for this effect is presumed to be as follows. The compound represented by formula (1) 1 is a group represented by formula (Q-1), and Q 2 However, =O, =S, =NR q1 or =CR q2 R q3 The compound has a benzobisdithiol skeleton having the structure: 1 But, -OY 11 , -OC(=O)-Y 11 , -OC(=O)OY 11 , -OC(=O)NR y11 -Y 11 , -OSO2-Y 11 Or a group containing a polymerizable group having an ethylenically unsaturated bond, and has an asymmetric structure. 1is a group represented by formula (Q-1) and has an asymmetric structure, it is presumed that the compatibility with solvents and curable compounds can be increased while suppressing decomposition or modification of the compound due to light irradiation, and that the precipitation of these compounds on the surface of a cured product obtained using the composition of the present invention can be suppressed. For this reason, it is presumed that the use of the composition of the present invention makes it possible to produce a cured product with excellent light resistance and suppressed haze.

[0012] The composition of the present invention may be a composition in the form of a solution containing a solvent. The composition of the present invention may also be a kneaded product. In this specification, the kneaded product refers to a product obtained by kneading a compound represented by formula (1) with a resin. That is, the kneaded product in this specification refers to a product in which the compound represented by formula (1) is mixed and dispersed in a resin, and is different from a solution in which the compound represented by formula (1) and a resin are dissolved or dispersed in a solvent. When the composition of the present invention is a kneaded product, the curable compound used contains a resin.

[0013] The kneaded material is preferably in the form of pellets. In this specification, pellets refer to a material obtained by granulating (pelletizing) the kneaded material into a fixed shape such as a sphere, ellipsoid, cylinder, or prism. The pellets are also preferably master pellets (master batches). The master pellets (master batches) refer to a material in which a high concentration of the compound represented by formula (1) is dispersed in a resin, and are mixed with a resin or the like at a specified ratio when forming a molded body.

[0014] Each component contained in the composition of the present invention will be described below.

[0015] <<Specific compounds>> (Compound represented by formula (1) (specific compound)) The composition of the present invention contains a compound represented by formula (1). Hereinafter, the compound represented by formula (1) is also referred to as a specific compound.

[0016] [ka] In formula (1), Q 1 represents a group represented by formula (Q-1); Q 2 are =O, =S, and =NR q1 or =CR q2 R q3 represents R q1 ~R q3 each independently represents a hydrogen atom or a substituent, R q2 and R q3 may be linked together to form a ring; R 1 -OY 11 , -OC(=O)-Y 11 , -OC(=O)OY 11 , -OC(=O)NR y11 -Y 11 , -OSO2-Y 11 or a group containing a polymerizable group having an ethylenically unsaturated bond, R y11 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group; Y 11 represents an alkyl group, an aralkyl group, or an aryl group; [ka] In formula (Q-1), * represents a bond, and R 101 and R 102 each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0017] -R 1 About- R in Equation (1) 1 -OY 11 , -OC(=O)-Y 11 , -OC(=O)OY 11 , -OC(=O)NR y11 -Y 11 , -OSO2-Y 11 or a group containing a polymerizable group having an ethylenically unsaturated bond, R y11represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group; Y 11 represents an alkyl group, an aralkyl group, or an aryl group.

[0018] The number of carbon atoms in the alkyl group is preferably 1 to 30. The lower limit is preferably 2 or more, more preferably 3 or more. The upper limit is preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, and most preferably 8 or less. The alkyl group may be linear, branched, or cyclic, and is preferably linear or branched. The alkyl group may have a substituent. Examples of the substituent include the groups described below for the substituent T.

[0019] The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aryl group may have a substituent. Examples of the substituent include the groups described below for the substituent T.

[0020] The number of carbon atoms in the alkyl portion of the aralkyl group is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. The number of carbon atoms in the aryl portion of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aralkyl group may have a substituent. Examples of the substituent include the groups explained in the description of the substituent T below. Specific examples of the aralkyl group include a benzyl group.

[0021] In the group containing a polymerizable group having an ethylenically unsaturated bond, examples of the polymerizable group having an ethylenically unsaturated bond include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and a (meth)acryloyloxy group and a vinylphenyl group are preferred.

[0022] Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include groups represented by the following formula (T1). *-X T1 -Y T1 -Z T1 (T1)

[0023] In formula (T1), X T1 is a single bond, -O-, -OC(=O)-, -OC(=O)O- or -OC(=O)NRx 1 - represents Rx 1 represents a hydrogen atom, an alkyl group, or an aryl group; Y T1 represents a single bond or a divalent linking group, Z T1 represents a polymerizable group having an ethylenically unsaturated bond.

[0024] Rx 1 The alkyl group represented by is preferably an alkyl group having 1 to 30 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. 1 The aryl group represented by Rx is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Specific examples include a phenyl group, a p-tolyl group, and a naphthyl group. 1 is preferably a hydrogen atom.

[0025] X T1 is preferably —O—.

[0026] Y T1Examples of the divalent linking group represented by include a hydrocarbon group and a group in which two or more hydrocarbon groups are linked via a single bond or a linking group. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred. The aliphatic hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The cyclic aliphatic hydrocarbon group may be a monocyclic or fused ring. The cyclic aliphatic hydrocarbon group may have a crosslinked structure. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include the substituent T described below. For example, the substituent may be a hydroxy group. Examples of the linking group linking two or more hydrocarbon groups include -NH-, -S(=O)2-, -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -NHC(=O)- and -C(=O)NH-, and -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -NHC(=O)- or -C(=O)NH- is preferred.

[0027] Z T1 Examples of the polymerizable group having an ethylenically unsaturated bond represented by include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and a (meth)acryloyloxy group and a vinylphenyl group are preferred.

[0028] R in Equation (1) 1 -OY 11 It is preferable that: -OY 11 In Y 11 represents an alkyl group, an aralkyl group, or an aryl group, and is preferably an alkyl group, and more preferably an alkyl group having two or more carbon atoms, because this allows for the formation of a cured product with reduced haze. Y 11 As a preferred embodiment of the present invention, Y 11is a branched alkyl group having 3 to 30 carbon atoms. Y 11 In another preferred embodiment, Y 11 may have a substituent that is an alkyl group having 2 to 30 carbon atoms and that has a substituent such as an alkoxycarbonyl group.

[0029] -Q 1 About- Q in equation (1) 1 represents a group represented by formula (Q-1). R in formula (Q-1) 101 and R 102 each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0030] R 101 and R 102 The number of carbon atoms in the alkyl group represented by is preferably 1 to 30. The upper limit is preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, and even more preferably 8 or less. The lower limit is preferably 2 or more, more preferably 3 or more. The alkyl group may be linear, branched, or cyclic, and is preferably linear or branched. The alkyl group may have a substituent. Examples of the substituent include the groups explained for the substituent T below.

[0031] R 101 and R 102 The number of carbon atoms in the aryl group represented by is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aryl group may have a substituent. Examples of the substituent include the groups explained for the substituent T below.

[0032] R 101 and R 102The number of carbon atoms in the alkyl portion of the aralkyl group represented by the formula (I) is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. The number of carbon atoms in the aryl portion of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aralkyl group may have a substituent. Examples of the substituent include the groups explained for the substituent T below.

[0033] R 101 and R 102 The heterocyclic ring in the heterocyclic group represented by the formula (I) preferably contains a 5- or 6-membered saturated or unsaturated heterocyclic ring. The heterocyclic group may have a heterocyclic ring condensed with an aliphatic ring, an aromatic ring, or another heterocyclic ring. Heteroatoms constituting the heterocyclic ring include B, N, O, S, Se, and Te, with N, O, and S being preferred. It is preferred that the carbon atom in the heterocyclic ring has a free valence (monovalent) (the heterocyclic group is bonded via a carbon atom). The number of carbon atoms in the heterocyclic group is preferably 1 to 40, more preferably 1 to 30, and even more preferably 1 to 20. Examples of saturated heterocyclic rings in the heterocyclic group include a pyrrolidine ring, a morpholine ring, a 2-bora-1,3-dioxolane ring, and a 1,3-thiazolidine ring. Examples of the unsaturated heterocyclic ring in the heterocyclic group include an imidazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzotriazole ring, a benzoselenazole ring, a pyridine ring, a pyrimidine ring, and a quinoline ring.

[0034] R 101 and R 102 Examples of the group containing a polymerizable group having an ethylenically unsaturated bond represented by formula (V1) include groups represented by formula (V1). *-X V1 -Y V1 -Z V1 ···(V1)

[0035] In formula (V1), X V1 is a single bond, -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -C(=O)NRx 2 - or -OC(=O)NRx2 - represents Rx 2 represents a hydrogen atom, an alkyl group, or an aryl group; Y V1 represents a single bond or a divalent linking group, Z V1 represents a polymerizable group having an ethylenically unsaturated bond.

[0036] Rx 2 The alkyl group and aryl group represented by are Rx of the group represented by formula (T1). 1 The meanings and preferred ranges of Rx are the same as those of the alkyl group and aryl group represented by Rx. 2 is preferably a hydrogen atom.

[0037] X V1 is preferably a single bond or —C(═O)—, more preferably a single bond.

[0038] Y V1 The divalent linking group represented by is Y in the group represented by formula (T1): T1 The preferred ranges are also the same as those described above for the divalent linking group represented by the formula (I).

[0039] Z V1 Examples of the polymerizable group having an ethylenically unsaturated bond represented by include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and a (meth)acryloyloxy group and a vinylphenyl group are preferred.

[0040] In formula (Q-1), R 101 or R 102 When one of the groups is a hydrogen atom, the other group is an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond, R 101 or R 102 When one of the above is a methyl group, the other is a hydrogen atom, an alkyl group having two or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond, R 101 or R 102 When either of the above is a phenyl group, the other preferably represents a hydrogen atom, an alkyl group, an aralkyl group, a substituted aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0041] R in formula (Q-1) 101 and R 102 As a preferred embodiment of R 101 and R 102 are each independently an alkyl group. 101 and R 102 Preferably, each of the alkyl groups represented by is independently an alkyl group having 2 or more carbon atoms. R in formula (Q-1) 101 and R 102 In another preferred embodiment, R 101 and R 102 are each independently an aralkyl group. R in formula (Q-1) 101 and R 102 In another preferred embodiment, R 101 and R 102 In one embodiment, at least one of the above is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0042] -Q 2 About- Q in equation (1) 2 are =O, =S, and =NR q1 or =CR q2 R q3 represents R q1 ~R q3 each independently represents a hydrogen atom or a substituent, R q2 and R q3 may be bonded to each other to form a ring.

[0043] R q1 ~R q3Examples of the substituent represented by include a cyano group, a carbamoyl group, a sulfamoyl group, a nitro group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkyl group, an aryl group, a heterocyclic group, and a group containing a polymerizable group having an ethylenically unsaturated bond. These groups may further have a substituent. Examples of the substituent include the groups listed as the substituent T described below.

[0044] The carbamoyl group includes carbamoyl groups having 1 to 10 carbon atoms, preferably carbamoyl groups having 2 to 8 carbon atoms, and more preferably carbamoyl groups having 2 to 5 carbon atoms.

[0045] The sulfamoyl group includes sulfamoyl groups having 0 to 10 carbon atoms, preferably sulfamoyl groups having 2 to 8 carbon atoms, and more preferably sulfamoyl groups having 2 to 5 carbon atoms.

[0046] Examples of the acyl group include acyl groups having 1 to 20 carbon atoms, preferably acyl groups having 1 to 12 carbon atoms, and more preferably acyl groups having 1 to 8 carbon atoms.

[0047] The alkylsulfonyl group includes alkylsulfonyl groups having 1 to 20 carbon atoms, preferably alkylsulfonyl groups having 1 to 10 carbon atoms, and more preferably alkylsulfonyl groups having 1 to 8 carbon atoms.

[0048] The arylsulfonyl group includes an arylsulfonyl group having 6 to 20 carbon atoms, and an arylsulfonyl group having 6 to 10 carbon atoms is preferred.

[0049] The alkylsulfinyl group includes alkylsulfinyl groups having 1 to 20 carbon atoms, preferably alkylsulfinyl groups having 1 to 10 carbon atoms, and more preferably alkylsulfinyl groups having 1 to 8 carbon atoms.

[0050] The arylsulfinyl group includes an arylsulfinyl group having 6 to 20 carbon atoms, and an arylsulfinyl group having 6 to 10 carbon atoms is preferred.

[0051] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 20 carbon atoms, preferably alkoxycarbonyl groups having 2 to 12 carbon atoms, and more preferably alkoxycarbonyl groups having 2 to 8 carbon atoms.

[0052] The aryloxycarbonyl group includes an aryloxycarbonyl group having 6 to 20 carbon atoms, preferably an aryloxycarbonyl group having 6 to 12 carbon atoms, and more preferably an aryloxycarbonyl group having 6 to 8 carbon atoms.

[0053] The alkyl group may be an alkyl group having 1 to 18 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.

[0054] The aryl group includes an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 15 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms.

[0055] The heterocyclic ring in the heterocyclic group preferably contains a 5- or 6-membered saturated or unsaturated heterocyclic ring. The heterocyclic group may have a heterocyclic ring condensed with an aliphatic ring, an aromatic ring, or another heterocyclic ring. Heteroatoms constituting the heterocyclic ring include B, N, O, S, Se, and Te, with N, O, and S being preferred. It is preferred that the carbon atoms in the heterocyclic ring have a free valence (monovalent) (the heterocyclic group is bonded via a carbon atom). The number of carbon atoms in the preferred heterocyclic group is 1 to 40, more preferably 1 to 30, and even more preferably 1 to 20.

[0056] Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include groups represented by formula (U1). *-X U1 -Y U1-Z U1 (U1)

[0057] In formula (U1), X U1 is a single bond, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -C(=O)NRx 3 - or -OC(=O)NRx 3 - represents Rx 3 represents a hydrogen atom, an alkyl group, or an aryl group; Y U1 represents a single bond or a divalent linking group, Z U1 represents a polymerizable group having an ethylenically unsaturated bond.

[0058] Rx 3 The alkyl group and aryl group represented by are Rx of the group represented by formula (T1). 1 The meanings and preferred ranges of Rx are the same as those of the alkyl group and aryl group represented by Rx. 3 is preferably a hydrogen atom.

[0059] X U1 is -C(=O)O- or -C(=O)NRx 3 - is preferred, and from the viewpoint of synthesis, -C(=O)O- is more preferred.

[0060] Y U1 The divalent linking group represented by is Y in the group represented by formula (T1): T1 The preferred ranges are also the same as those described above for the divalent linking group represented by the formula (I).

[0061] Z U1 Examples of the polymerizable group having an ethylenically unsaturated bond represented by include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and a (meth)acryloyloxy group and a vinylphenyl group are preferred.

[0062] Q in equation (1) 2is used because the effect of the present invention is more pronounced. q2 R q3 It is preferable that:

[0063] Q 2 GA=CR q2 R q3 In the case where R q2 and R q3 In this embodiment, R q2 and R q3 The substituent represented by is preferably a cyano group, a carbamoyl group, a sulfamoyl group, a nitro group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond, and more preferably a cyano group.

[0064] Q 2 GA=CR q2 R q3 In another preferred embodiment, R q2 and R q3 or R is a cyano group, and the other is a carbamoyl group, a sulfamoyl group, a nitro group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond. q2 and R q3 Preferably, one of the groups is a cyano group and the other is an acyl group or an alkoxycarbonyl group.

[0065] Q 2 GA=CR q2 R q3 In another preferred embodiment, R q2 and R q3 R q2and R q3 Examples of the ring formed by bonding these rings together include a pyrazolidinedione ring, an indane ring, a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, an oxazoline ring, a thiazoline ring, a pyrroline ring, a pyrazoline ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a piperazine ring, and a pyran ring, and a pyrazolidinedione ring or an indane ring is preferred. These may have a substituent at any position.

[0066] R q2 and R q3 are bonded to each other to form a ring, Q 2 is preferably a group represented by formula (Q2-1) or formula (Q2-2). [ka]

[0067] In the formula, * represents a bond, and R 201 ~R 206 each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0068] R 201 ~R 206 The above group represented by is R 101 and R 102 The contents and preferable ranges are the same as those described above.

[0069] (substituent T) Examples of the substituent T include the following groups. Halogen atoms (e.g., chlorine, bromine, iodine); Alkyl groups [linear, branched, and cyclic alkyl groups. Specific examples include linear or branched alkyl groups (preferably linear or branched alkyl groups having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl, and 2-ethylhexyl), cycloalkyl groups (preferably cycloalkyl groups having 3 to 30 carbon atoms, such as cyclohexyl, cyclopentyl, and 4-n-dodecylcyclohexyl), bicycloalkyl groups (preferably bicycloalkyl groups having 5 to 30 carbon atoms, i.e., monovalent groups obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms, such as bicyclo[1,2,2]heptan-2-yl and bicyclo[2,2,2]octan-3-yl), and tricyclo structures having more ring structures. The alkyl groups in the substituents described below (for example, the alkyl groups of alkylthio groups) also represent alkyl groups within this concept. alkenyl groups [straight-chain, branched, and cyclic alkenyl groups. Specifically, these include straight-chain or branched alkenyl groups (preferably straight-chain or branched alkenyl groups having 2 to 30 carbon atoms, such as vinyl, allyl, prenyl, geranyl, and oleyl), cycloalkenyl groups (preferably cycloalkenyl groups having 3 to 30 carbon atoms, i.e., monovalent groups obtained by removing one hydrogen atom from a cycloalkene having 3 to 30 carbon atoms, such as 2-cyclopenten-1-yl and 2-cyclohexen-1-yl), and bicycloalkenyl groups (preferably bicycloalkenyl groups having 5 to 30 carbon atoms, i.e., monovalent groups obtained by removing one hydrogen atom from a bicycloalkene having one double bond, such as bicyclo[2,2,1]hept-2-en-1-yl and bicyclo[2,2,2]oct-2-en-4-yl). an alkynyl group (preferably a linear or branched alkynyl group having 2 to 30 carbon atoms, for example, an ethynyl group or a propargyl group);

[0070] an aryl group (preferably an aryl group having 6 to 30 carbon atoms, such as a phenyl group, a p-tolyl group, a naphthyl group, a m-chlorophenyl group, or an o-hexadecanoylaminophenyl group); heterocyclic groups (preferably monovalent groups obtained by removing one hydrogen atom from a 5- or 6-membered aromatic or non-aromatic heterocyclic compound, more preferably 5- or 6-membered aromatic heterocyclic groups having 3 to 30 carbon atoms, such as a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, or a 2-benzothiazolyl group); cyano group; hydroxy groups; nitro group; carboxyl group; an alkoxy group (preferably a linear or branched alkoxy group having 1 to 30 carbon atoms, for example, a methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group); an aryloxy group (preferably an aryloxy group having 6 to 30 carbon atoms, for example, a phenoxy group, a 2-methylphenoxy group, a 4-t-butylphenoxy group, a 3-nitrophenoxy group, or a 2-tetradecanoylaminophenoxy group); a heterocyclic oxy group (preferably a heterocyclic oxy group having 2 to 30 carbon atoms, for example, a 1-phenyltetrazol-5-oxy group, a 2-tetrahydropyranyloxy group); acyloxy groups (preferably formyloxy groups, alkylcarbonyloxy groups having 2 to 30 carbon atoms, and arylcarbonyloxy groups having 6 to 30 carbon atoms, for example, formyloxy groups, acetyloxy groups, pivaloyloxy groups, stearoyloxy groups, benzoyloxy groups, and p-methoxyphenylcarbonyloxy groups);

[0071] a carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms, for example, an N,N-dimethylcarbamoyloxy group, an N,N-diethylcarbamoyloxy group, a morpholinocarbonyloxy group, an N,N-di-n-octylaminocarbonyloxy group, or an Nn-octylcarbamoyloxy group); an alkoxycarbonyloxy group (preferably an alkoxycarbonyloxy group having 2 to 30 carbon atoms, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or an n-octylcarbonyloxy group); an aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, a phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, or a pn-hexadecyloxyphenoxycarbonyloxy group); an amino group (preferably an amino group, an alkylamino group having 1 to 30 carbon atoms, or an anilino group having 6 to 30 carbon atoms, for example, an amino group, a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group, or a diphenylamino group); an acylamino group (preferably a formylamino group, an alkylcarbonylamino group having 2 to 30 carbon atoms, or an arylcarbonylamino group having 6 to 30 carbon atoms, for example, a formylamino group, an acetylamino group, a pivaloylamino group, a lauroylamino group, a benzoylamino group, or a 3,4,5-tri-n-octyloxyphenylcarbonylamino group);

[0072] an aminocarbonylamino group (preferably an aminocarbonylamino group having 1 to 30 carbon atoms, for example, a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, an N,N-diethylaminocarbonylamino group, or a morpholinocarbonylamino group); an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an n-octadecyloxycarbonylamino group, or an N-methylmethoxycarbonylamino group); an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, or an mn-octyloxyphenoxycarbonylamino group); a sulfamoylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms, for example, a sulfamoylamino group, an N,N-dimethylaminosulfonylamino group, or an Nn-octylaminosulfonylamino group); an alkyl or arylsulfonylamino group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms, or an arylsulfonylamino group having 6 to 30 carbon atoms, for example, a methylsulfonylamino group, a butylsulfonylamino group, a phenylsulfonylamino group, a 2,3,5-trichlorophenylsulfonylamino group, or a p-methylphenylsulfonylamino group); mercapto group; an alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms, for example, a methylthio group, an ethylthio group, or an n-hexadecylthio group); an arylthio group (preferably an arylthio group having 6 to 30 carbon atoms, for example, a phenylthio group, a p-chlorophenylthio group, or an m-methoxyphenylthio group); a heterocyclic thio group (preferably a heterocyclic thio group having 2 to 30 carbon atoms, for example, a 2-benzothiazolylthio group, a 1-phenyltetrazol-5-ylthio group);

[0073] a sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms, for example, an N-ethylsulfamoyl group, an N-(3-dodecyloxypropyl)sulfamoyl group, an N,N-dimethylsulfamoyl group, an N-acetylsulfamoyl group, an N-benzoylsulfamoyl group, or an N-(N'-phenylcarbamoyl)sulfamoyl group); sulfo group; an alkyl or arylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms, or an arylsulfinyl group having 6 to 30 carbon atoms, for example, a methylsulfinyl group, an ethylsulfinyl group, a phenylsulfinyl group, or a p-methylphenylsulfinyl group); an alkyl or arylsulfonyl group (preferably an alkylsulfonyl group having 1 to 30 carbon atoms, or an arylsulfonyl group having 6 to 30 carbon atoms, for example, a methylsulfonyl group, an ethylsulfonyl group, a phenylsulfonyl group, or a p-methylphenylsulfonyl group);

[0074] acyl groups (preferably formyl groups, alkylcarbonyl groups having 2 to 30 carbon atoms, arylcarbonyl groups having 7 to 30 carbon atoms, and heterocyclic carbonyl groups having 4 to 30 carbon atoms and bonded to a carbonyl group via a carbon atom, such as acetyl groups, pivaloyl groups, 2-chloroacetyl groups, stearoyl groups, benzoyl groups, pn-octyloxyphenylcarbonyl groups, 2-pyridylcarbonyl groups, and 2-furylcarbonyl groups); an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms, for example, a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, a m-nitrophenoxycarbonyl group, or a pt-butylphenoxycarbonyl group); an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, or an n-octadecyloxycarbonyl group); a carbamoyl group (preferably a carbamoyl group having 1 to 30 carbon atoms, for example, a carbamoyl group, an N-methylcarbamoyl group, an N,N-dimethylcarbamoyl group, an N,N-di-n-octylcarbamoyl group, or an N-(methylsulfonyl)carbamoyl group); an aryl or heterocyclic azo group (preferably an aryl azo group having 6 to 30 carbon atoms, or a heterocyclic azo group having 3 to 30 carbon atoms, for example, a phenylazo group, a p-chlorophenylazo group, or a 5-ethylthio-1,3,4-thiadiazol-2-ylazo group); an imide group (preferably an N-succinimide group or an N-phthalimide group); a phosphino group (preferably a phosphino group having 2 to 30 carbon atoms, for example, a dimethylphosphino group, a diphenylphosphino group, or a methylphenoxyphosphino group); a phosphinyl group (preferably a phosphinyl group having 2 to 30 carbon atoms, for example, a phosphinyl group, a dioctyloxyphosphinyl group, or a diethoxyphosphinyl group); a phosphinyloxy group (preferably a phosphinyloxy group having 2 to 30 carbon atoms, for example, a diphenoxyphosphinyloxy group or a dioctyloxyphosphinyloxy group); a phosphinylamino group (preferably a phosphinylamino group having 2 to 30 carbon atoms, for example, a dimethoxyphosphinylamino group, a dimethylaminophosphinylamino group);

[0075] Among the groups listed above, for groups having hydrogen atoms, one or more hydrogen atoms may be substituted with the above-mentioned substituent T. Examples of such substituents include alkylcarbonylaminosulfonyl groups, arylcarbonylaminosulfonyl groups, alkylsulfonylaminocarbonyl groups, and arylsulfonylaminocarbonyl groups. Specific examples include methylsulfonylaminocarbonyl groups, p-methylphenylsulfonylaminocarbonyl groups, acetylaminosulfonyl groups, and benzoylaminosulfonyl groups.

[0076] Specific examples of the specific compound include compounds having the following structure: In the structural formula shown below, Et is an ethyl group, and Ph is a phenyl group. [ka] [ka] [ka] [ka] [ka]

[0077] The specific compound can be used as an ultraviolet absorber, a yellow colorant, a specific wavelength absorber, or the like.

[0078] When the specific compound is used as an ultraviolet absorber, the maximum absorption wavelength of the specific compound is preferably in the wavelength range of 380 to 420 nm, and more preferably in the wavelength range of 390 to 410 nm.

[0079] The specific compound preferably has an absorbance at a wavelength of 440 nm that is less than 0.02 when the absorbance at a wavelength of 400 nm is taken as 1.

[0080] The molar absorption coefficient at the maximum absorption wavelength of the specific compound is preferably 80,000 L / mol·cm or more, more preferably 85,000 L / mol·cm or more, and even more preferably 90,000 L / mol·cm or more. The molar absorption coefficient at a wavelength of 400 nm is preferably 30,000 L / mol·cm or more, more preferably 40,000 L / mol·cm or more, and even more preferably 50,000 L / mol·cm or more. Furthermore, the molar absorption coefficient at a wavelength of 440 nm is preferably 1000 L / mol·cm or less, more preferably 800 L / mol·cm or less, and even more preferably 600 L / mol·cm or less.

[0081] The absorbance, maximum absorption wavelength, and molar extinction coefficient of a specific compound can be determined by measuring the spectroscopic spectrum of a solution prepared by dissolving the specific compound in ethyl acetate using a 1 cm quartz cell at room temperature (25° C.) Examples of measuring devices include a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation).

[0082] The specific compound can be produced, for example, by selecting appropriate reactants, bases, solvents, and reaction temperatures for a compound represented by formula (10) described below. The compound represented by formula (10) forms a dianion in a specific base and solvent, lowering the reaction barrier for the first step. Therefore, the specific compound can be produced by selecting appropriate reactants, bases, solvents, and reaction temperatures for a compound represented by formula (10).

[0083] The content of the specific compound in the total solid content of the composition is preferably 0.01 to 95% by mass. The lower limit can be 0.05% by mass or more, 0.1% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or more. The upper limit can be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, or 20% by mass or less.

[0084] The composition of the present invention may contain only one specific compound or two or more specific compounds. When two or more specific compounds are contained, the total amount thereof is preferably within the above range.

[0085] <<Compound represented by formula (10)>> The composition of the present invention may further contain a compound represented by formula (10). By further containing a compound represented by formula (10), precipitation of a specific compound in the composition can be further suppressed.

[0086] [ka]

[0087] In formula (10), Q 11 represents a group represented by formula (Q-1a); Q 12 are =O, =S, and =NR q11 or =CR q12 R q13 represents R q11 ~R q13 each independently represents a hydrogen atom or a substituent, R q12 and R q13 may be bonded to each other to form a ring. [ka] In formula (Q-1a), * represents a bond, and R 101a and R 102a each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0088] R in formula (Q-1a) 101a and R 102a is the R in formula (Q-1) 101 and R 102 The same applies to the preferred range. Q in equation (10) 11 and Q 12 is Q in Eq. (1). 1 and Q 2 The same applies to the preferred range.

[0089] When the composition of the present invention contains a compound represented by formula (10), the content of the compound represented by formula (10) is preferably 0.01 to 95 parts by mass per 100 parts by mass of the specific compound. The upper limit is preferably 50 parts by mass or less, and more preferably 20 parts by mass or less. The lower limit is preferably 0.05 parts by mass or more, and more preferably 0.1 parts by mass or more.

[0090] The composition of the present invention may contain only one compound represented by formula (10), or may contain two or more compounds represented by formula (10). When two or more compounds represented by formula (10) are contained, the total amount thereof is preferably within the above range.

[0091] <<Other UV absorbers>> The composition of the present invention may contain an ultraviolet absorber other than the specific compound (hereinafter also referred to as "other ultraviolet absorber"), and according to this embodiment, a cured product capable of blocking light of a wide range of wavelengths in the ultraviolet region can be formed.

[0092] The maximum absorption wavelength of the other ultraviolet absorber is preferably in the wavelength range of 300 to 380 nm, more preferably in the wavelength range of 300 to 370 nm, even more preferably in the wavelength range of 310 to 360 nm, and particularly preferably in the wavelength range of 310 to 350 nm.

[0093] The other ultraviolet absorber is also preferably a compound having a polymerizable group, such as a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, or a vinylphenyl group.

[0094] As other ultraviolet absorbents, can be enumerated aminobutadiene-based ultraviolet absorbents, dibenzoylmethane-based ultraviolet absorbents, benzotriazole-based ultraviolet absorbents, benzophenone-based ultraviolet absorbents, salicylic acid-based ultraviolet absorbents, acrylate-based ultraviolet absorbents and triazine-based ultraviolet absorbents, and preferably benzotriazole-based ultraviolet absorbents, benzophenone-based ultraviolet absorbents and triazine-based ultraviolet absorbents, and more preferably benzotriazole-based ultraviolet absorbents and triazine-based ultraviolet absorbents.Specific examples of other ultraviolet absorbents can be enumerated compounds described in the examples below. Further, other ultraviolet absorbers are described in paragraphs 0065 to 0070 of JP 2009-263616 A, paragraph 0065 of WO 2017 / 122503 A, JP 2003-128730 A, JP 2003-129033 A, JP 2014-077076 A, JP 2015-164994 A, JP 2015-168822 A, JP 2018-135282 A, JP 2018-168089 A, JP 2018-168278 A, JP 2018-188589 A, JP 2019-001767 A, JP 2020-023697 A, Compounds described in JP 2020-041013 A, JP 5518613 A, JP 5868465 A, JP 6301526 A, JP 6354665 A, JP 2017-503905 A, WO 2015 / 064674, WO 2015 / 064675, WO 2017 / 102675, WO 2018 / 190281, WO 2018 / 216750, WO 2019 / 087983, EP 2379512, EP 2951163, etc. can be used.

[0095] When the composition of the present invention contains another UV absorber, the content of the other UV absorber in the total solid content of the composition is preferably 0.01 to 95% by mass. The lower limit can be 0.05% by mass or more, 0.1% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or more. The upper limit can be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, or 20% by mass or less.

[0096] The total content of the specific compound and other UV absorbers in the total solid content of the composition is preferably 0.02 to 95% by mass. The lower limit can be 0.05% by mass or more, 0.1% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or more. The upper limit can be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, or 20% by mass or less.

[0097] The composition of the present invention may contain only one type of other ultraviolet absorber, or may contain two or more types. When two or more types of other ultraviolet absorbers are contained, the total amount thereof is preferably within the above range.

[0098] <<Curable compound>> The composition of the present invention contains a curable compound. Examples of the curable compound include a polymerizable compound, an alkoxysilane compound, and a resin. The resin may be a non-polymerizable resin (a resin without a polymerizable group) or a polymerizable resin (a resin with a polymerizable group). Examples of the polymerizable group include an ethylenically unsaturated bond-containing group and a cyclic ether group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a vinylphenyl group, a (meth)allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, and a (meth)acryloylamide group. Preferred are a (meth)allyl group, a (meth)acryloyl group, and a (meth)acryloyloxy group, and more preferred are a (meth)acryloyloxy group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. Preferred is an epoxy group.

[0099] The curable compound contained in the composition of the present invention preferably contains at least one selected from a resin and a polymerizable compound. The curable compound may be a combination of a resin and a polymerizable compound.

[0100] (polymerizable compound) As the polymerizable compound, any compound that can be polymerized and cured by the application of energy can be used without limitation. The polymerizable compound may be a radical polymerizable compound or a cation polymerizable compound.

[0101] The polymerizable compound may be any of a monomer, a prepolymer (i.e., a dimer, a trimer, or an oligomer), a mixture thereof, and a (co)polymer of a compound selected from a monomer and a prepolymer, but is preferably a monomer.

[0102] The molecular weight of the polymerizable compound is preferably 100 to 3000. The upper limit is preferably 2000 or less, more preferably 1500 or less. The lower limit is preferably 150 or more, more preferably 250 or more.

[0103] -Radical polymerizable compound- Examples of the radical polymerizable compound include compounds having an ethylenically unsaturated bond-containing group. Examples of the radical polymerizable compound include unsaturated carboxylic acids (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), esters of unsaturated carboxylic acids, amides of unsaturated carboxylic acids, and (co)polymers of unsaturated carboxylic acids or their esters or amides. Among these, esters of unsaturated carboxylic acids and aliphatic polyhydric alcohols, amides of unsaturated carboxylic acids and aliphatic polyhydric amines, and homopolymers or copolymers thereof are preferred.

[0104] Examples of radically polymerizable compounds that can be used include an addition reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a nucleophilic substituent (e.g., a hydroxy group, an amino group, a mercapto group, etc.) with a monofunctional or polyfunctional isocyanate compound or an epoxy compound; a dehydration condensation reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a nucleophilic substituent with a monofunctional or polyfunctional carboxylic acid; an addition reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having an electrophilic substituent (e.g., an isocyanate group, an epoxy group, etc.) with a monofunctional or polyfunctional alcohol, amine, or thiol; and a substitution reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a leaving substituent (e.g., a halogen atom, a tosyloxy group, etc.) with a monofunctional or polyfunctional alcohol, amine, or thiol. Furthermore, compounds obtained by replacing the above unsaturated carboxylic acid with an unsaturated phosphonic acid, styrene, vinyl ether, etc. can also be used.

[0105] The radical polymerizable compound may be a combination of a plurality of compounds having different functionalities or a plurality of compounds having different types of polymerizable groups (for example, acrylic acid esters, methacrylic acid esters, styrene compounds, vinyl ether compounds, etc.).

[0106] The radical polymerizable compound is preferably a (meth)acrylate compound, more preferably a di- or higher functional (meth)acrylate compound, even more preferably a di- to 15-functional (meth)acrylate compound, still more preferably a di- to 10-functional (meth)acrylate compound, and particularly preferably a di- to hexa-functional (meth)acrylate compound.

[0107] Specific examples of the radical polymerizable compound include pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tri((meth)acryloyloxyethyl)isocyanurate, pentaerythritol tetra(meth)acrylate ethylene oxide EO (ethylene oxide) modified product, dipentaerythritol hexa(meth)acrylate EO (ethylene oxide) modified product, and benzyl (meth)acrylate.

[0108] Commercially available radically polymerizable compounds include polyfunctional (meth)acrylate compounds such as the KAYARAD series (e.g., D-330, D-320, D-310, PET-30, TPA-330, and DPHA) manufactured by Nippon Kayaku Co., Ltd., the NK Ester series (e.g., A-DPH-12E, A-TMMT, and A-TMM-3) manufactured by Shin-Nakamura Chemical Co., Ltd., the Light Acrylate series (e.g., DCP-A) manufactured by Kyoeisha Chemical Co., Ltd., the Aronix series (e.g., M-305, M-306, M-309, M-450, M-402, and TO-1382) manufactured by Toagosei Co., Ltd., and the Viscoat series (e.g., V#802) manufactured by Osaka Organic Chemical Industry Ltd.

[0109] The radical polymerizable compound may be a (meth)acrylate compound described in JP-A-48-064183, JP-B-49-043191, or JP-B-52-030490, or a compound introduced as a photocurable monomer or oligomer in Journal of the Japan Adhesion Association, Vol. 20, No. 7, pp. 300-308 (1984).

[0110] -Cationic polymerizable compound- The cationically polymerizable compound may be a compound having a cationically polymerizable group. Examples of the cationically polymerizable group include cyclic ether groups such as epoxy groups and oxetanyl groups, and vinyl ether groups, with the cyclic ether group being preferred. The cationically polymerizable compound is preferably a polyfunctional cationically polymerizable compound having two or more cationically polymerizable groups.

[0111] Examples of the cationically polymerizable compound include polyfunctional alicyclic epoxy compounds, polyfunctional heterocyclic epoxy compounds, polyfunctional oxetane compounds, alkylene glycol diglycidyl ethers, and alkylene glycol monovinyl monoglycidyl ethers.

[0112] Specific examples of the cationically polymerizable compound include 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, xylylene bisoxetane, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, cyclohexanedimethanol divinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovinyl ether, 4-hydroxybutyl vinyl ether, and the compounds described in paragraphs 0029 to 0058 of JP 2012-046577 A.

[0113] The cationically polymerizable compound may be a (meth)acrylate compound having a cationically polymerizable group. Specific examples of the (meth)acrylate compound having a cationically polymerizable group include 3,4-epoxycyclohexylmethyl methacrylate. Commercially available products include Cyclomer M100 manufactured by Daicel Corporation.

[0114] The cationically polymerizable compound may be the Aron Oxetane series (OXT-101, OXT-121, OXT-221, etc.) manufactured by Toagosei Co., Ltd., the Celloxide series (2021P) manufactured by Daicel Corporation, or alkyl divinyl ether CHDVE, alkyl monovinyl ether EHVE, hydroxyalkyl vinyl ether CHMVE, or hydroxyalkyl vinyl ether HBVE manufactured by Nippon Carbide Industries Co., Ltd. In addition, specific examples of epoxy resins described below may also be used.

[0115] (alkoxysilane compounds) The alkoxysilane compound is preferably a trifunctional or tetrafunctional alkoxysilane compound. A trifunctional alkoxysilane compound refers to an alkoxysilane compound having three alkoxy groups directly bonded to silicon atoms in one molecule, and a tetrafunctional alkoxysilane compound refers to an alkoxysilane compound having four alkoxy groups directly bonded to silicon atoms in one molecule. Specific examples of the alkoxysilane compound include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, γ-glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropyltriethoxysilane, γ-glycidyloxypropylmethyldimethoxysilane, γ-glycidyloxypropylmethyldiethoxysilane, γ-methacryloyloxypropyltrimethoxysilane, γ-methacryloyloxypropyltriethoxy ... propylmethyldimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 3,4-epoxycyclohexylethyltrimethoxysilane, 3,4-epoxycyclohexylethyltriethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, 4-trimethoxysilylstyrene, 3,3,3-trifluoropropyltrimethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane, diphenyldimethoxysilane, divinyldiethoxysilane, bis(triethoxysilylpropyl)tetrasulfide, 3-(trimethoxysilyl)propyl isocyanate, 3-(triethoxysilyl)propyl isocyanate, and the like.

[0116] (resin) Examples of resins include (meth)acrylic resins, ene-thiol resins, polyester resins, polycarbonate resins, vinyl polymers [e.g., polydiene resins, polyalkene resins, polystyrene resins, polyvinyl ether resins, polyvinyl alcohol resins, polyvinyl ketone resins, polyfluorovinyl resins, and polyvinyl bromide resins], polythioether resins, polyphenylene resins, polyurethane resins, thiourethane resins, polysulfonate resins, nitrosopolymer resins, polysiloxane resins, polysulfide resins, polythioester resins, polysulfone resins, polysulfonamide resins, polyamide resins, polyimine resins, polyurea resins, polyphosphazene resins, polysilane resins, polysilazane resins, polyfuran resins, polybenzyl resins, Examples of suitable resins include benzoxazole resins, polyoxadiazole resins, polybenzothiazinophenothiazine resins, polybenzothiazole resins, polypyrazinoquinoxaline resins, polyquinoxaline resins, polybenzimidazole resins, polyoxoisoindoline resins, polydioxoisoindoline resins, polytriazine resins, polypyridazine resins, polypiperazine resins, polypyridine resins, polypiperidine resins, polytriazole resins, polypyrazole resins, polypyrrolidine resins, polycarborane resins, polyoxabicyclononane resins, polydibenzofuran resins, phthalate resins, polyacetal resins, polyimide resins, polyamideimide resins, olefin resins, cyclic olefin resins, epoxy resins, and cellulose acylate resins. Examples of suitable resins include sol-gel cured products of alkoxysilane compounds.

[0117] Examples of (meth)acrylic resins include polymers containing structural units derived from (meth)acrylic acid and / or its esters. Specific examples include polymers obtained by polymerizing at least one compound selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid esters, (meth)acrylamide, and (meth)acrylonitrile. Examples of (meth)acrylic resins include the SK Dyne series (e.g., SK Dyne-SF2147) from Soken Chemical & Engineering Co., Ltd.

[0118] Examples of polyester resins include polymers obtained by reacting polyols (e.g., ethylene glycol, propylene glycol, glycerin, and trimethylolpropane) with polybasic acids (e.g., aromatic dicarboxylic acids (e.g., terephthalic acid, isophthalic acid, and naphthalenedicarboxylic acid, and dicarboxylic acids in which hydrogen atoms in the aromatic rings are substituted with methyl groups, ethyl groups, phenyl groups, etc.), aliphatic dicarboxylic acids having 2 to 20 carbon atoms (e.g., adipic acid, sebacic acid, and dodecanedicarboxylic acid), and alicyclic dicarboxylic acids (e.g., cyclohexanedicarboxylic acid)), as well as polymers obtained by ring-opening polymerization of cyclic ester compounds such as caprolactone monomers (e.g., polycaprolactone). Specific examples of polyester resins include polyethylene terephthalate and polyethylene naphthalate. Commercially available polyester resins, such as the Vylon series (e.g., Vylon 500) manufactured by Toyobo Co., Ltd., can also be used.

[0119] Examples of epoxy resins include bisphenol A epoxy resins, bisphenol F epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, aliphatic epoxy resins, etc. Commercially available epoxy resins may be used, and examples of commercially available products include the following:

[0120] Examples of commercially available bisphenol A epoxy resins include jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (all manufactured by Mitsubishi Chemical Corporation), and EPICLON860, EPICLON1050, EPICLON1051, and EPICLON1055 (all manufactured by DIC Corporation). Commercially available examples of bisphenol F epoxy resins include jER806, jER807, jER4004, jER4005, jER4007, and jER4010 (manufactured by Mitsubishi Chemical Corporation), EPICLON830 and EPICLON835 (manufactured by DIC Corporation), and LCE-21 and RE-602S (manufactured by Nippon Kayaku Co., Ltd.). Commercially available examples of phenol novolac epoxy resins include jER152, jER154, jER157S70, and jER157S65 (manufactured by Mitsubishi Chemical Corporation), and EPICLON N-740, EPICLON N-770, and EPICLON N-775 (manufactured by DIC Corporation). Examples of commercially available cresol novolac epoxy resins include EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, and EPICLON N-695 (all manufactured by DIC Corporation), and EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.).Commercially available examples of aliphatic epoxy resins include the ADEKA RESIN EP series (e.g., EP-4080S, EP-4085S, and EP-4088S; manufactured by ADEKA Corporation), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (manufactured by Daicel Corporation), DENACOL EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (manufactured by Nagase ChemteX Corporation), ADEKA RESIN Examples of commercially available epoxy resins include the EP series (e.g., EP-4000S, EP-4003S, EP-4010S, and EP-4011S manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, and EPPN-502 manufactured by ADEKA Corporation, and jER1031S manufactured by Mitsubishi Chemical Corporation. Other commercially available epoxy resins include Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 manufactured by NOF Corporation, epoxy group-containing polymers.

[0121] As the cellulose acylate resin, the cellulose acylates described in paragraphs 0016 to 0021 of JP-A No. 2012-215689 are preferably used.

[0122] The polystyrene resin is preferably a resin containing 50% by mass or more of repeating units derived from styrene-based monomers, more preferably a resin containing 70% by mass or more of repeating units derived from styrene-based monomers, and even more preferably a resin containing 85% by mass or more of repeating units derived from styrene-based monomers.

[0123] Specific examples of styrene-based monomers include styrene and its derivatives. Here, the styrene derivatives are compounds in which other groups are bonded to styrene, such as alkylstyrenes such as o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, o-ethylstyrene, and p-ethylstyrene, and substituted styrenes in which a hydroxyl group, an alkoxy group, a carboxyl group, a halogen, or the like is introduced into the benzene nucleus of styrene, such as hydroxystyrene, tert-butoxystyrene, vinylbenzoic acid, o-chlorostyrene, and p-chlorostyrene.

[0124] The polystyrene resin may also contain repeating units derived from monomers other than styrene-based monomers. Examples of such other monomers include alkyl (meth)acrylates such as methyl (meth)acrylate, cyclohexyl (meth)acrylate, methylphenyl (meth)acrylate, and isopropyl (meth)acrylate; unsaturated carboxylic acid monomers such as methacrylic acid, acrylic acid, itaconic acid, maleic acid, fumaric acid, and cinnamic acid; unsaturated dicarboxylic acid anhydride monomers such as maleic anhydride, itaconic acid, ethyl maleic acid, methyl itaconic acid, and chloromaleic acid; unsaturated nitrile monomers such as acrylonitrile and methacrylonitrile; and conjugated dienes such as 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, and 1,3-hexadiene.

[0125] Commercially available polystyrene resins include AS-70 (acrylonitrile-styrene copolymer resin) manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., SMA2000P (styrene-maleic acid copolymer) manufactured by Kawahara Oil Chemical Co., Ltd., Clearen 530L and Clearen 730L manufactured by Denka Co., Ltd., Tufprene 126S and Asaprene T411 manufactured by Asahi Kasei Corporation, Kraton D1102A and Kraton D1116A manufactured by Kraton Polymer Japan, Styrolux S and Styrolux T manufactured by Styrolution, Asaflex 840 and Asaflex 860 manufactured by Asahi Kasei Corporation, 679, HF77, SGP-10, 475D, H0103, and HT478 manufactured by PS Japan, and DIC Styrene XC-515, DIC Styrene XC-535, and DIC Styrene manufactured by DIC Corporation. GH-8300-5, etc. Commercially available hydrogenated polystyrene resins include the Tuftec H series manufactured by Asahi Kasei Corporation, the Kraton G series manufactured by Shell Japan, Dynaron (hydrogenated styrene-butadiene random copolymer) manufactured by JSR Corporation, and Septon manufactured by Kuraray Co., Ltd. Commercially available modified polystyrene resins include the Tuftec M series manufactured by Asahi Kasei Corporation, Epofriend manufactured by Daicel Corporation, polar group-modified Dynaron manufactured by JSR Corporation, and Reseda manufactured by Toagosei Co., Ltd.

[0126] Examples of cyclic olefin resins include (R1) polymers containing structural units derived from norbornene compounds, (R2) polymers containing structural units derived from monocyclic olefin compounds other than norbornene compounds, (R3) polymers containing structural units derived from cyclic conjugated diene compounds, (R4) polymers containing structural units derived from vinyl alicyclic hydrocarbon compounds, and hydrogenated polymers containing structural units derived from each of the compounds (R1) to (R4). In this specification, polymers containing structural units derived from norbornene compounds and polymers containing structural units derived from monocyclic olefin compounds include ring-opened polymers of each compound.

[0127] The cyclic olefin resin is not particularly limited, but is preferably a polymer having a structural unit derived from a norbornene compound, represented by formula (A-II) or formula (A-III). The polymer having the structural unit represented by formula (A-II) is an addition polymer of a norbornene compound, and the polymer having the structural unit represented by formula (A-III) is a ring-opening polymer of a norbornene compound.

[0128] [ka]

[0129] In formula (A-II) and formula (A-III), m is an integer of 0 to 4, and 0 or 1 is preferred. R in Formula (A-II) and Formula (A-III) 3 ~R 6 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms. R 3 ~R 6 Examples of the hydrocarbon group represented by include an alkyl group, an alkenyl group, an alkynyl group, and an aryl group, and an alkyl group or an aryl group is preferred. X 2 and X 3 , Y 2 and Y 3 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom, -(CH2) n COOR 11 , -(CH2) n OCOR 12 , -(CH2) n NCO, -(CH2) n NO2, -(CH2) n CN, -(CH2) n CONR 13 R 14 , -(CH2) n NR 13 R 14 , -(CH2) n OZ 1 , -(CH2) n W 1 , or X2 and Y 2 or X 3 and Y 3 are bonded to each other to form (-CO)2O or (-CO)2NR 15 Represents. where X 2 , X 3 , Y 2 and Y 3 R in each of the above groups 11 ~R 15 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms; Z 1 represents a hydrocarbon group or a halogen-substituted hydrocarbon group, W 1 is Si(R 16 ) p D (3-p) (R 16 represents a hydrocarbon group having 1 to 10 carbon atoms, D represents a halogen atom, -OCOR 17 -OR 17 (R 17 represents a hydrocarbon group having 1 to 10 carbon atoms. p represents an integer of 0 to 3. n represents an integer of 0 to 10, preferably 0 to 8, and more preferably 0 to 6.

[0130] R in Formula (A-II) and Formula (A-III) 3 ~R 6 are each independently preferably a hydrogen atom or -CH3, and more preferably a hydrogen atom in terms of moisture permeability. X 2 and X 3 are each preferably a hydrogen atom, —CH 3 , or —C 2 H 5 , and more preferably a hydrogen atom in terms of moisture permeability. Y 2 and Y 3 are each independently a hydrogen atom, a halogen atom (particularly a chlorine atom) or -(CH2) n COOR 11 (particularly -COOCH3) is preferred, and in terms of moisture permeability, a hydrogen atom is more preferred. The other groups are selected appropriately.

[0131] The polymer having the structural unit represented by formula (A-II) or formula (A-III) may further contain one or more structural units represented by formula (AI).

[0132] [ka]

[0133] In formula (AI), R 1 and R 2 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms; X 1 and Y 1 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom, -(CH2) n COOR 11 , -(CH2) n OCOR 12 , -(CH2) n NCO, -(CH2) n NO2, -(CH2) n CN, -(CH2) n CONR 13 R 14 , -(CH2) n NR 13 R 14 , -(CH2) n OZ 1 , -(CH2) n W 1 , or X 2 and Y 2 or X 3 and Y 3 are bonded to each other to form (-CO)2O or (-CO)2NR 15 represents X 1 and Y 1 R in each of the above groups 11 ~R 15 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms; Z 1 represents a hydrocarbon group or a halogen-substituted hydrocarbon group, W 1 is Si(R 16 ) p D (3-p) (R 16represents a hydrocarbon group having 1 to 10 carbon atoms, D represents a halogen atom, -OCOR 17 -OR 17 (R 17 represents a hydrocarbon group having 1 to 10 carbon atoms. p represents an integer of 0 to 3. n represents an integer of 0 to 10.

[0134] The content of the structural unit represented by formula (A-II) or formula (A-III) in the cyclic polyolefin resin is preferably 90 mass% or less, more preferably 30 to 85 mass%, even more preferably 50 to 79 mass%, and even more preferably 60 to 75 mass%.

[0135] Cyclic olefin resins are described in JP-A No. 10-007732, JP-A No. 2002-504184, WO 2004 / 070463, etc., and the contents of these publications can be referred to as appropriate.

[0136] The cyclic olefin resin can be obtained by addition polymerization of norbornene compounds (for example, polycyclic unsaturated compounds of norbornene).

[0137] Commercially available cyclic olefin resins include the Arton series (for example, Arton G, F, and RX4500) manufactured by JSR Corporation, and Zeonor ZF14, ZF16, and Zeonex 250 and 280 manufactured by Zeon Corporation.

[0138] Examples of cyclic olefin resins include copolymers obtained by addition copolymerization of norbornene compounds with olefins such as ethylene, propylene, and butene; conjugated dienes such as butadiene and isoprene; non-conjugated dienes such as ethylidene norbornene; and ethylenically unsaturated compounds such as acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, acrylic acid esters, methacrylic acid esters, maleimide, vinyl acetate, and vinyl chloride. Among these, copolymers with ethylene are preferred. Examples of such addition (co)polymers of norbornene compounds are sold by Mitsui Chemicals, Inc. under the trade name APEL, and include those with different glass transition temperatures (Tg), such as APL8008T (Tg 70°C), APL6011T (Tg 105°C), APL6013T (Tg 125°C), and APL6015T (Tg 145°C). Polyplastics Co., Ltd. sells pellets such as TOPAS 8007, 6013, and 6015. Ferrania also sells Appear 3000.

[0139] Hydrogenated cyclic olefin resins can be synthesized by subjecting norbornene compounds, etc., to addition polymerization or metathesis ring-opening polymerization, followed by hydrogenation. Synthetic methods are described in, for example, JP-A Nos. 01-240517, 07-196736, 60-026024, 62-019801, 2003-159767, and 2004-309979.

[0140] The weight average molecular weight of the cyclic olefin resin is preferably from 5,000 to 500,000, more preferably from 8,000 to 200,000, and even more preferably from 10,000 to 100,000.

[0141] Examples of polycarbonate resins include reaction products of polyhydric phenol compounds with phosgene or carbonate compounds.

[0142] Polyhydric phenol compounds include hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bisphenol A, bisphenol C, bisphenol E, bisphenol F, bisphenol M, bisphenol P, bisphenol S, bisphenol Z, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 2,2-bis( Examples of the hydroxyphenyl ester include 3-isopropyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfoxide, 4,4'-dihydroxydiphenyl sulfide, 3,3'-dimethyl-4,4'-dihydroxydiphenyl sulfide, and 4,4'-dihydroxydiphenyl oxide, and hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, and bisphenol A are preferred.

[0143] Examples of the carbonate ester compound include phosgene, diphenyl carbonate, bis(chlorophenyl) carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, dimethyl carbonate, diethyl carbonate, and dibutyl carbonate, with bis(diphenyl) carbonate, dimethyl carbonate, and diethyl carbonate being preferred.

[0144] Commercially available polycarbonate resins include Panlite L-1250WP and Panlite SP-1516 manufactured by Teijin Limited, Iupizeta EP-5000 and Iupizeta EP-4000 manufactured by Mitsubishi Gas Chemical Company, Inc., and Caliber 301-30 manufactured by Sumika Polycarbonate Co., Ltd.

[0145] Examples of thiourethane resins include reaction products of isocyanate compounds and polythiol compounds, reaction products of thiourethane resin precursors, etc. Commercially available thiourethane resin precursors include MR-7, MR-8, MR-10, and MR-174 manufactured by Mitsui Chemicals, Inc.

[0146] Examples of polyamide resins include aliphatic polyamide resins and aromatic polyamide resins. Examples of aliphatic polyamide resins include nylon 6, nylon 11, nylon 12, nylon 46, nylon 66, nylon 666, nylon 610, and nylon 612. Examples of aromatic polyamide resins include resins polymerized by dehydration condensation of diamines and dicarboxylic acids, in which at least one of the diamines and dicarboxylic acids contains an aromatic ring. Specific examples of aromatic polyamide resins include condensation polymers of metaxylylenediamine and adipic acid or adipic acid halide.

[0147] The resin may have an acid group. Examples of the acid group include a carboxy group, a phosphate group, a sulfonic acid group, and a phenolic hydroxy group. The acid group may be of one type or of two or more types. The resin having an acid group can be used as an alkali-soluble resin and can also be used as a dispersant.

[0148] Regarding the resin having an acid group, the description in paragraphs

[0558] to

[0571] of JP 2012-208494 A (corresponding to paragraphs

[0685] to

[0700] of U.S. Patent Application Publication No. 2012 / 0235099) and the description in paragraphs

[0076] to

[0099] of JP 2012-198408 A can be referred to, the contents of which are incorporated herein by reference. Furthermore, as the resin having an acid group, ACRYBASE FF-426 (manufactured by Nippon Shokubai Co., Ltd.) can also be used.

[0149] The acid value of the resin having an acid group is preferably 30 to 200 mgKOH / g. The lower limit of the acid value is preferably 50 mgKOH / g or more, more preferably 70 mgKOH / g or more. The upper limit of the acid value is preferably 150 mgKOH / g or less, more preferably 120 mgKOH / g or less. The acid value of the resin is measured in accordance with JIS K0070 (1992) and calculated by converting 1 mmol / g = 56.1 mgKOH / g.

[0150] The resin may have a polymerizable group. Examples of the polymerizable group include an ethylenically unsaturated bond-containing group and a cyclic ether group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a styrene group, an allyl group, a methallyl group, and a (meth)acryloyl group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group.

[0151] Commercially available resins containing polymerizable groups include the Dianal BR series (polymethyl methacrylate (PMMA), such as Dianal BR-80, BR-83, and BR-87; manufactured by Mitsubishi Chemical Corporation), Photomer 6173 (a COOH-containing polyurethane acrylic oligomer; Diamond Shamrock Co., Ltd.), Viscoat R-264, and KS Resist 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series (e.g., ACA230AA), Placcel CF200 series (all manufactured by Daicel Corporation), and Ebecryl 3800 (manufactured by Daicel-UCB Co., Ltd.), and Acricur-RD-F8 (manufactured by Nippon Shokubai Co., Ltd.). Other examples include commercially available products such as those described above for epoxy resins.

[0152] When the composition of the present invention is used for lenses (for example, eyeglass lenses), the resin is preferably a thermoplastic resin such as a carbonate resin or a (meth)acrylic resin, or a thermosetting resin such as a urethane resin.

[0153] A pressure-sensitive adhesive or adhesive can also be used for the resin. Examples of adhesives include acrylic pressure-sensitive adhesives, rubber pressure-sensitive adhesives, and silicone pressure-sensitive adhesives. An acrylic pressure-sensitive adhesive is a pressure-sensitive adhesive containing a polymer of a (meth)acrylic monomer ((meth)acrylic polymer). Examples of adhesives include urethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives, and silicone adhesives. Among these, urethane resin adhesives and silicone adhesives are preferred because of their high adhesive strength. Commercially available adhesives may be used, and examples of commercially available products include a urethane resin adhesive (LIS-073-50U: product name) from Toyo Ink Co., Ltd. and an acrylic pressure-sensitive adhesive (SK Dyne-SF2147: product name) from Soken Chemical & Engineering Co., Ltd.

[0154] The resin preferably contains at least one selected from a (meth)acrylic resin, a polystyrene resin, a polyester resin, a polyurethane resin, a thiourethane resin, a polyimide resin, an epoxy resin, a polycarbonate resin, a phthalate resin, a cellulose acylate resin, and a cyclic olefin resin, and more preferably contains an epoxy resin because it is easier to obtain a cured product in which precipitation of a specific compound is further suppressed.

[0155] The weight average molecular weight (Mw) of the resin is preferably 2,000 to 2,000,000. The lower limit of the Mw of the resin is preferably 5,000 or more, more preferably 10,000 or more, and even more preferably 50,000 or more. The upper limit of the Mw of the resin is preferably 1,000,000 or less, more preferably 500,000 or less, and even more preferably 200,000 or less. Furthermore, when an epoxy resin is used, the weight average molecular weight (Mw) of the epoxy resin is preferably 100 or more, more preferably 200 to 2,000,000. The upper limit of the Mw of the epoxy resin is preferably 1,000,000 or less, and more preferably 500,000 or less. The lower limit of the Mw of the epoxy resin is preferably 2,000 or more.

[0156] The weight-average molecular weight (Mw) is a value measured by gel permeation chromatography (GPC). Measurements by GPC were performed using an HLC (registered trademark)-8020GPC (manufactured by Tosoh Corporation) as the measuring device, three TSKgel (registered trademark) Super Multipore HZ-H columns (4.6 mm ID × 15 cm, manufactured by Tosoh Corporation), and THF (tetrahydrofuran) as the eluent. Measurement conditions were a sample concentration of 0.45% by mass, a flow rate of 0.35 ml / min, a sample injection volume of 10 μl, and a measurement temperature of 40°C, using an RI detector. A calibration curve was prepared using eight samples of "TSK standard polystyrene" (manufactured by Tosoh Corporation): "F-40," "F-20," "F-4," "F-1," "A-5000," "A-2500," "A-1000," and "n-propylbenzene."

[0157] The total light transmittance of the resin is preferably 80% or more, more preferably 85% or more, and even more preferably 90% or more. In this specification, the total light transmittance of the resin is a value measured based on the contents described on pages 225-232 of "4th Edition Experimental Chemistry Lectures 29 Polymer Material Media" (Maruzen, 1992), edited by the Chemical Society of Japan.

[0158] The content of the curable compound in the total solid content of the composition is preferably 1 to 99.9% by mass. The lower limit is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 70% by mass or more. The upper limit is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less. The composition may contain only one type of curable compound, or may contain two or more types. When two or more types of curable compounds are contained, the total amount thereof is preferably within the above range.

[0159] When the curable compound contained in the composition of the present invention contains a resin, the content of the resin in the total solid content of the composition is preferably 1 to 99.9% by mass. The lower limit is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 70% by mass or more. The upper limit is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less. The composition may contain only one type of resin, or may contain two or more types. When two or more types of resins are contained, the total amount thereof is preferably within the above range.

[0160] When the curable compound contained in the composition of the present invention includes a polymerizable compound, the content of the polymerizable compound in the total solid content of the composition is preferably 0.1 to 90% by mass. The lower limit is preferably 1% by mass or more, and more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less. The composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. When two or more types of polymerizable compounds are contained, the total amount thereof is preferably within the above range.

[0161] When the curable compound contained in the composition of the present invention includes an alkoxysilane compound, the content of the alkoxysilane compound in the total solid content of the composition is preferably 0.1 to 90% by mass. The lower limit is preferably 1% by mass or more, and more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less. The composition of the present invention may contain only one type of alkoxysilane compound, or may contain two or more types. When two or more types of alkoxysilane compounds are contained, the total amount thereof is preferably within the above range.

[0162] <<Polymerization initiator>> The composition of the present invention may contain a polymerization initiator. As the polymerization initiator, a compound capable of generating an initiating species necessary for a polymerization reaction by the application of energy can be used. Examples of the polymerization initiator include a radical polymerization initiator and a cationic polymerization initiator. When a radically polymerizable compound is used as the polymerizable compound, the polymerization initiator is preferably a radical polymerization initiator. When a cationic polymerizable compound is used as the polymerizable compound, the polymerization initiator is preferably a cationic polymerization initiator. The polymerization initiator can be appropriately selected from, for example, a photopolymerization initiator and a thermal polymerization initiator, with a photopolymerization initiator being preferred. The photopolymerization initiator is a compound that is photosensitive to exposure light and initiates or promotes polymerization of a polymerizable compound. Examples of the photopolymerization initiator include a photoradical polymerization initiator and a photocationic polymerization initiator, with a photoradical polymerization initiator being preferred. The photoradical polymerization initiator is preferably a compound that generates radicals in response to actinic rays with a wavelength of 300 nm or more.

[0163] (Photoradical polymerization initiator) Examples of the photoradical polymerization initiator include oxime compounds, halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), oxydiazole compounds, carbonyl compounds, ketal compounds, benzoin compounds, acridine compounds, organic peroxides, azo compounds, coumarin compounds, azide compounds, metallocene compounds, hexaarylbiimidazole compounds, organic boric acid compounds, disulfonic acid compounds, onium salt compounds, acetophenone compounds, acylphosphine compounds, and benzophenone compounds.

[0164] Examples of acetophenone compounds include aminoacetophenone compounds and hydroxyacetophenone compounds. Examples of acetophenone compounds include those described in JP 2009-191179 A and JP 10-291969 A. Commercially available aminoacetophenone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins BV). Commercially available hydroxyacetophenone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins BV).

[0165] Examples of the acylphosphine compound include the acylphosphine compounds described in Japanese Patent No. 4225898. Examples of commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (both manufactured by IGM Resins BV).

[0166] Examples of the benzophenone compound include benzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 4-methoxybenzophenone, 2-chlorobenzophenone, 4-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzophenone, 2-ethoxycarbonylbenzophenone, benzophenonetetracarboxylic acid or its tetramethyl ester, 4,4'-bis(dialkylamino)benzophenones (e.g., 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(dicyclohexylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dihydroxyethylamino)benzophenone), 4-methoxy-4'-dimethylaminobenzophenone, 4,4'-dimethoxybenzophenone, 4-dimethylaminobenzophenone, and 4-dimethylaminoacetophenone. From the viewpoint of sensitivity and the light resistance of the resulting cured product, 4,4'-bis(diethylamino)benzophenone is preferred.

[0167] Examples of oxime compounds include those described in JP 2001-233842 A, JP 2000-080068 A, JP 2006-342166 A, and JP 2016-006475 A, paragraphs 0073 to 0075. Among oxime compounds, oxime ester compounds are preferred. Commercially available oxime compounds include Irgacure OXE01, Irgacure OXE02 (manufactured by BASF), and Irgacure OXE03 (manufactured by BASF).

[0168] Examples of halogenated hydrocarbon derivatives include those described in Wakabayashi et al., Bull Chem. Soc. Japan, 42, 2924 (1969), U.S. Pat. No. 3,905,815, JP-B No. 46-004605, JP-A No. 48-036281, JP-A No. 55-032070, JP-A No. 60-239736, JP-A No. 61-169835, JP-A No. 61-169837, JP-A No. 62-058241, JP-A No. 62-212401, JP-A No. 63-070243, JP-A No. 63-298339, and M.P. Hutt, Journal of Heterocyclic Examples of suitable compounds include those described in "Chemistry" 1 (No. 3), (1970), and preferred are oxazole compounds or triazine compounds substituted with a trihalomethyl group.

[0169] Examples of the hexaarylbiimidazole compound include compounds described in Japanese Patent Publication No. 06-029285, U.S. Pat. Nos. 3,479,185, 4,311,783, and 4,622,286. Specific examples include 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-bromophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o,p-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetra(m-methoxyphenyl)biimidazole. 2,2'-bis(o,o'-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-nitrophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-methylphenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-trifluorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and the like.

[0170] (Cationic photopolymerization initiator) The photocationic polymerization initiator is not particularly limited as long as it is a compound that generates a protonic acid or a Lewis acid upon irradiation with light. The photoacid generator is preferably a compound that generates an acid in response to actinic rays with a wavelength of 300 nm or more, more preferably 300 to 450 nm. The photoacid generator is preferably a compound that generates an acid with a pKa of 4 or less upon irradiation with light, more preferably a compound that generates an acid with a pKa of 3 or less, and even more preferably a compound that generates an acid with a pKa of 2 or less.

[0171] Examples of the photocationic polymerization initiator include oxime sulfonate compounds, triazine compounds, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, sulfone compounds, sulfonic acid ester compounds, iminosulfonic acid ester compounds, carboxylic acid ester compounds, and sulfonimide compounds.

[0172] Specific examples of the cationic photopolymerization initiator include the compounds described in paragraphs

[0061] to

[0108] of JP 2012-046577 A and paragraphs

[0029] to

[0030] of JP 2002-122994 A, the compounds described in paragraphs

[0037] to

[0063] of JP 2002-122994 A, and the oxime sulfonate compounds described in paragraphs

[0081] to

[0108] of JP 2013-210616 A. Commercially available cationic photopolymerization initiators include WPAG-469 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), CPI-100P (manufactured by San-Apro Co., Ltd.), CPI-210S (manufactured by San-Apro Co., Ltd.), and Irgacure 290 (BASF Japan Ltd.).

[0173] (thermal polymerization initiator) The thermal polymerization initiator is not particularly limited, and known thermal polymerization initiators can be used. For example, azo compounds such as dimethyl 2,2'-azobis(isobutyrate), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(N-butyl-2-methylpropionamide), dimethyl 1,1'-azobis(1-cyclohexanecarboxylate), and 2,2'-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride; organic peroxides such as 1,1-di(t-hexylperoxy)cyclohexane, 1,1-di(t-butylperoxy)cyclohexane, 2,2-di(4,4-di-(t-butylperoxy)cyclohexyl)propane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, dicumyl peroxide, di-t-butyl peroxide, t-butylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, cumene hydroperoxide, and t-butyl hydroperoxide; Inorganic peroxides such as potassium persulfate, ammonium persulfate, and hydrogen peroxide; Examples include:

[0174] When the composition of the present invention contains a polymerization initiator, the content of the polymerization initiator in the total solid content of the composition is preferably 0.1 to 20% by mass. The lower limit is preferably 0.3% by mass or more, and more preferably 0.4% by mass or more. The upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less. The composition of the present invention may contain only one type of polymerization initiator, or may contain two or more types. When two or more types of polymerization initiators are contained, the total amount thereof is preferably within the above range.

[0175] <<Catalyst>> The composition of the present invention may contain a catalyst. Examples of the catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, acetic acid, and propionic acid, and base catalysts such as sodium hydroxide, potassium hydroxide, and triethylamine. When the composition of the present invention contains a catalyst, the content of the catalyst is preferably 0.1 to 100 parts by mass, more preferably 0.1 to 50 parts by mass, and even more preferably 0.1 to 20 parts by mass, per 100 parts by mass of the resin. The composition of the present invention may contain only one type of catalyst, or may contain two or more types. When two or more types of catalysts are contained, the total amount thereof is preferably within the above range.

[0176] <<Surfactants>> The composition of the present invention may contain a surfactant. Examples of the surfactant include those described in paragraph 0017 of Japanese Patent No. 4502784 and paragraphs 0060 to 0071 of JP-A No. 2009-237362.

[0177] The surfactant is preferably a nonionic surfactant, a fluorine-based surfactant, or a silicone-based surfactant.

[0178] Commercially available fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144, F-437, F-475, F-477, F-479, F-482, F-551-A, F-552, F-554, F-555-A, F-556, F-557, F-558, F-559, and F-5 60, F-561, F-565, F-563, F-568, F-575, F-780, EXP, MFS-330, R-41, R-41-LM, R-01, R-40, R-40-LM, RS-43, TF-1956, RS-90, R-94, RS-72-K, DS-21 (all manufactured by DIC Corporation), Fluorad FC430, FC431, FC171 (all manufactured by Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (all manufactured by AGC Inc.), PolyFox PF636, PF656, PF6320, PF6520, PF7002 (all manufactured by OMNOVA), Futergent Examples include 710FM, 610FM, 601AD, 601ADH2, 602A, 215M, 245F, 251, 212M, 250, 209F, 222F, 208G, 710LA, 710FS, 730LM, 650AC, and 681 (all manufactured by NEOS Corporation).

[0179] Acrylic compounds that have a molecular structure with a functional group containing a fluorine atom and that volatilize when heated by cleavage of the fluorine atom-containing functional group can also be used as fluorosurfactants. Examples of such fluorosurfactants include the Megafac DS series manufactured by DIC Corporation (The Chemical Daily, February 22, 2016; The Nikkei Business Daily, February 23, 2016), such as Megafac DS-21.

[0180] As the fluorine-based surfactant, it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.

[0181] The fluorine-based surfactant may also be a block polymer.

[0182] The fluorine-based surfactant may also be a fluorine-containing polymer compound containing a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a repeating unit derived from a (meth)acrylate compound having two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy groups or propyleneoxy groups).

[0183] The fluorine-containing surfactant may be a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain. Commercially available products include Megafac RS-101, RS-102, RS-718K, and RS-72-K (all manufactured by DIC Corporation).

[0184] Furthermore, because there are concerns about the environmental compatibility of compounds containing linear perfluoroalkyl groups with seven or more carbon atoms, it is preferable to use fluorosurfactants that use alternative materials to perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS).

[0185] Silicone surfactants include linear polymers consisting of siloxane bonds and modified siloxane polymers with organic groups introduced into the side chains or terminals. Commercially available silicone surfactants include DOWSIL 8032 ADDITIVE, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (all manufactured by Dow Corning Toray Co., Ltd.), X-22-4952, X-22-4272, X-22-6266, KF-351A, K354L, KF-355A, and KF-94. No. 5, KF-640, KF-642, KF-643, X-22-6191, X-22-4515, KF-6004, KP-341, KF-6001, KF-6002 (all manufactured by Shin-Etsu Silicones Co., Ltd.), F-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all manufactured by Momentive Performance Materials), BYK307, BYK323, BYK330 (all manufactured by BYK-Chemie), and the like.

[0186] Examples of nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (for example, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fatty acid esters. Commercially available nonionic surfactants include Pluronic L10, L31, L61, L62, 10R5, 17R2, and 25R2 (all manufactured by BASF), Tetronic 304, 701, 704, 901, 904, and 150R1 (all manufactured by BASF), Solsperse 20000 (all manufactured by The Lubrizol Group), NCW-101, NCW-1001, and NCW-1002 (all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), Paionin D-6112, D-6112-W, and D-6315 (all manufactured by Takemoto Oil & Fat Co., Ltd.), Olfine E1010, and Surfynol 104, 400, and 440 (all manufactured by Nissin Chemical Industry Co., Ltd.).

[0187] The content of the surfactant in the total solid content of the composition of the present invention is preferably 0.01 to 3.0 mass%, more preferably 0.05 to 1.0 mass%, and even more preferably 0.10 to 0.80 mass%. The surfactant may be one type or two or more types. When two or more types are used, the total amount preferably falls within the above range.

[0188] <<Solvent>> The composition of the present invention preferably contains a solvent. The solvent is not particularly limited, and examples thereof include water and organic solvents. The solvent is preferably an organic solvent.

[0189] Examples of the organic solvent include alcohol-based solvents, ester-based solvents, ether-based solvents, ketone-based solvents, amide-based solvents, hydrocarbon-based solvents, and halogen-based solvents. Specific examples of alcohol-based solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-methoxy-2-propanol, 2-ethoxyethanol, 2-butoxyethanol, ethylene glycol, propylene glycol, and glycerin. Specific examples of ester-based solvents include methyl acetate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkoxyacetic acid alkyl esters (e.g., methyl alkoxyacetate, ethyl alkoxyacetate, butyl alkoxyacetate (specifically, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.)), 3-oxypropionic acid alkyl esters, and 2-oxypropionic acid alkyl esters. , methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethylene carbonate, and the like. Specific examples of ether-based solvents include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, polyethylene glycol, polypropylene glycol, ethylene glycol dialkyl ether, propylene glycol dialkyl ether, polyethylene glycol dialkyl ether, polypropylene glycol dialkyl ether, and dioxane. Specific examples of the amide solvent include N-methylpyrrolidone, dimethylformamide, and dimethylacetamide. Specific examples of ketone solvents include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, and 3-heptanone. Specific examples of hydrocarbon solvents include toluene and xylene. Specific examples of halogen-based solvents include chloroform and methylene chloride. These organic solvents may be used in combination of two or more kinds.

[0190] The organic solvent preferably contains at least one selected from methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate.

[0191] The content of the solvent in the composition of the present invention is preferably 10 to 90% by mass, more preferably 30 to 90% by mass, and even more preferably 50 to 90% by mass. The composition of the present invention may contain only one solvent, or may contain two or more solvents. When two or more solvents are contained, the total amount thereof is preferably within the above range. When the composition of the present invention is used as a kneaded product, the content of the organic solvent in the composition is preferably 0.1% by mass or less, and more preferably 0.01% by mass or less.

[0192] <<Plasticizers>> When the composition of the present invention is used as a kneaded product, the composition of the present invention may contain a plasticizer. Examples of the plasticizer include phthalate ester-based plasticizers, phosphate ester-based plasticizers, trimellitate ester-based plasticizers, fatty acid ester-based plasticizers, polyester-based plasticizers, glycerin-based plasticizers, and polyalkylene glycol-based plasticizers, with phthalate ester-based plasticizers and phosphate ester-based plasticizers being preferred.

[0193] Examples of phthalate ester plasticizers include dimethyl phthalate, diethyl phthalate, diisopropyl phthalate, dibutyl phthalate, diisobutyl phthalate, dihexyl phthalate, dicyclohexyl phthalate, diphenyl phthalate, bis(2-ethylhexyl) phthalate, diisononyl phthalate, diisodecyl phthalate, and diundecyl phthalate. Examples of the phosphate ester plasticizer include trimethyl phosphate, triethyl phosphate, tributyl phosphate, triphenyl phosphate, and tricresyl phosphate. Examples of trimellitic acid ester plasticizers include tributyl trimellitate and tris(2-ethylhexyl) trimellitate. Examples of fatty acid ester plasticizers include dimethyl adipate, diethyl adipate, dipropyl adipate, diisopropyl adipate, dibutyl adipate, diisobutyl adipate, dimethyl dodecanoate, dibutyl maleate, and ethyl oleate. Examples of polyester plasticizers include polyesters composed of an acid component such as adipic acid, sebacic acid, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid, or rosin and a diol component such as propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, ethylene glycol, or diethylene glycol, and polyesters with hydroxycarboxylic acids such as polycaprolactone. These polyesters may be end-blocked with a monofunctional carboxylic acid or a monofunctional alcohol, or may be end-blocked with an epoxy compound or the like. Examples of the glycerin-based plasticizer include glycerin monoacetomonolaurate, glycerin diacetomonolaurate, glycerin monoacetomonostearate, glycerin diacetomonooleate, and glycerin monoacetomonomonoacetate. Examples of the polyalkylene glycol plasticizer include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide addition polymers of bisphenols, propylene oxide addition polymers of bisphenols, and tetrahydrofuran addition polymers of bisphenols, as well as terminal epoxy-modified compounds, terminal ester-modified compounds, and terminal ether-modified compounds thereof.

[0194] The molecular weight of the plasticizer is preferably less than 3,000, more preferably 2,000 or less, and even more preferably 1,500 or less.

[0195] The content of the plasticizer in the composition of the present invention is preferably 0.001 to 30% by mass. The lower limit is preferably 0.005% by mass or more, and more preferably 0.01% by mass or more. The upper limit is preferably 20% by mass or less, and more preferably 10% by mass or less. The kneaded product may contain only one type of plasticizer, or may contain two or more types. When two or more types of plasticizers are contained, the total amount thereof is preferably within the above range.

[0196] <<Anti-fading agent>> The composition of the present invention may contain a discoloration inhibitor. Examples of discoloration inhibitors include amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds, carotenoid compounds, metal complex compounds, and benzolactone compounds. The amine compounds are preferably hydroxyamine compounds, tertiary amine compounds, or aminooxyl compounds, more preferably tertiary amine compounds or aminooxyl compounds. The metal complex compounds are preferably Ni complex compounds or Co complex compounds, more preferably Ni complex compounds. The discoloration inhibitor is preferably at least one selected from amine compounds and benzolactone compounds, more preferably an amine compound.

[0197] The content of the anti-fading agent in the total solid content of the composition is preferably 0.01 to 50% by mass. The lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more. The upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less. The composition of the present invention may contain only one type of anti-fading agent, or may contain two or more types. When two or more types of anti-fading agents are contained, the total amount thereof is preferably within the above range.

[0198] <<Other additives>> The composition of the present invention may contain, as needed, any additives such as a processing stabilizer, an antioxidant, a compatibilizer, etc. By adding these components as needed, various properties of the resulting cured product can be adjusted as needed.

[0199] <Uses of the composition> The composition of the present invention can also be suitably used in applications where it may be exposed to sunlight or light, including ultraviolet light. Specific examples include coating materials or films for window glass in homes, facilities, transportation equipment, etc.; interior and exterior materials and paints for homes, facilities, transportation equipment, etc.; components for ultraviolet-emitting light sources such as fluorescent lamps and mercury lamps; components for solar cells, precision machinery, electronic and electrical equipment, and display devices; containers or packaging materials for food, chemicals, pharmaceuticals, etc.; agricultural and industrial sheets; textile products and fibers for clothing such as sportswear, stockings, and hats; lenses or coating materials for such lenses as plastic lenses, contact lenses, eyeglasses, and artificial eyes; optical products such as optical filters, prisms, mirrors, and photographic materials; stationery such as tape and ink; sign plates, indicators, and surface coating materials for such signs. For details, please refer to paragraphs

[0158] to

[0218] of JP 2009-263617 A and paragraphs

[0161] to

[0194] of JP 2009-096971 A, the contents of which are incorporated herein by reference.

[0200] The composition of the present invention can be preferably used for optical components, etc. For example, it is preferably used as a composition for ultraviolet cut filters, lenses, or protective materials. The form of the protective material is not particularly limited, but examples include a coating film, a film, and a sheet. The composition of the present invention can also be used as a pressure-sensitive adhesive or an adhesive.

[0201] The composition of the present invention can also be used in various components of display devices. For example, in the case of a liquid crystal display device, the composition can be used in components constituting the liquid crystal display device, such as an antireflection film, a polarizing plate protective film, an optical film, a retardation film, a pressure-sensitive adhesive, and an adhesive. In the case of an organic electroluminescence display device, the composition can be used in components constituting the organic electroluminescence display device, such as an optical film, a polarizing plate protective film in a circular polarizing plate, a retardation film such as a quarter-wave plate, an adhesive, or a pressure-sensitive adhesive.

[0202] <Cured products and their applications> The cured product of the present invention is obtained using the composition of the present invention described above. In this specification, the term "cured product" includes a dried product obtained by drying and solidifying the composition, and, in the case where the composition undergoes a curing reaction, a cured product obtained by curing the composition.

[0203] The cured product of the present invention may be obtained as a molded article obtained by molding the composition into a desired shape. The shape of the molded article can be appropriately selected depending on the application and purpose. Examples of the shape of the molded article include a coating film, a film, a sheet, a plate, a lens, a tube, and a fiber.

[0204] The cured product of the present invention is preferably used as an optical element, such as an ultraviolet cut filter, a lens, or a protective material. It can also be used as a polarizing plate.

[0205] The ultraviolet cut filter can be used in products such as optical filters, display devices, solar cells, window glass, etc. The type of display device is not particularly limited, but examples include liquid crystal display devices and organic electroluminescence display devices.

[0206] When the cured product of the present invention is used for a lens, the cured product of the present invention itself may be formed into a lens shape and used. The cured product of the present invention may also be used as a coating film on the lens surface or as an intermediate layer (adhesive layer) of a cemented lens. Examples of cemented lenses include those described in paragraphs 0094 to 0102 of WO 2019 / 131572, the contents of which are incorporated herein by reference.

[0207] The type of protective material is not particularly limited, but examples thereof include protective materials for display devices, protective materials for solar cells, protective materials for window glass, protective materials for organic electroluminescence display devices, etc. The shape of the protective material is not particularly limited, but examples thereof include coating film, film, sheet, etc.

[0208] <Optical components> The optical component of the present invention includes a cured product obtained using the composition of the present invention described above. The cured product of the present invention may be obtained as a molded product obtained by molding the composition of the present invention described above into a desired shape. The shape of the molded product can be appropriately selected depending on the application and purpose. Examples include a coating film, film, sheet, plate, lens, tube, fiber, etc.

[0209] The optical members include ultraviolet cut filters, lenses, and protective materials.

[0210] The ultraviolet cut filter can be used in products such as optical filters, display devices, solar cells, window glass, etc. The type of display device is not particularly limited, but examples include liquid crystal display devices and organic electroluminescence display devices.

[0211] Examples of lenses include those in which the cured product of the present invention itself is formed into a lens shape; and those in which the cured product of the present invention is used as a coating film on the surface of a lens or as an intermediate layer (adhesive layer or pressure-sensitive adhesive layer) of a cemented lens.

[0212] The type of protective material is not particularly limited, but examples thereof include protective materials for display devices, protective materials for solar cells, protective materials for window glass, protective materials for organic electroluminescence display devices, etc. The shape of the protective material is not particularly limited, but examples thereof include coating film, film, sheet, etc.

[0213] Another example of an optical component is a resin film. The resin film can be formed using the composition of the present invention, which uses a resin as the curable compound. Examples of resins used in the resin film-forming composition include the resins described above. (Meth)acrylic resins, polyester fibers, cyclic olefin resins, and cellulose acylate resins are preferred, with cellulose acylate resins being more preferred. The resin film-forming composition can contain additives described in paragraphs 0022 to 0067 of JP 2012-215689 A. Examples of such additives include sugar esters. Adding a sugar ester compound to a resin film-forming composition containing a cellulose acylate resin can reduce total haze and internal haze without impairing the expression of optical properties and even without heat treatment before the stretching process. Furthermore, a resin film (cellulose acylate film) using a composition containing a cellulose acylate resin can be produced by the method described in paragraphs 0068 to 0096 of JP 2012-215689 A. Furthermore, the resin film may further be laminated with a hard coat layer described in paragraphs 0097 to 0113 of JP-A No. 2012-215689.

[0214] Another example of an optical member is an optical member having a laminate of a support and a resin layer, in which at least one of the support and the resin layer contains the cured product of the present invention.

[0215] The thickness of the resin layer in the laminate is preferably 1 μm to 2500 μm, and more preferably 10 μm to 500 μm.

[0216] The support in the laminate is preferably a material that has transparency to the extent that the optical performance is not impaired. The support being transparent means that the support is optically transparent, specifically, that the support has a total light transmittance of 85% or more. The total light transmittance of the support is preferably 90% or more, and more preferably 95% or more.

[0217] A suitable example of the support is a resin film. Examples of resins constituting the resin film include ester resins (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), polycyclohexane dimethylene terephthalate (PCT), etc.), olefin resins (e.g., polypropylene (PP), polyethylene (PE), etc.), polyvinyl chloride (PVA), tricellulose acetate (TAC), etc. Among these, PET is preferred in terms of versatility.

[0218] The thickness of the support can be appropriately selected depending on the use or purpose, etc. In general, the thickness is preferably from 5 μm to 2500 μm, and more preferably from 20 μm to 500 μm.

[0219] The support may also be a releasable support. Such a laminate is preferably used for a polarizing plate or the like. Here, the releasable support refers to a support that can be peeled from the resin film. The stress when peeling the support from the resin film is preferably 0.05 N / 25 mm or more and 2.00 N / 25 mm or less, more preferably 0.08 N / 25 mm or more and 0.50 N / 25 mm or less, and even more preferably 0.11 N / 25 mm or more and 0.20 N / 25 mm or less. The stress when peeling the support from the resin film was evaluated by first cutting a piece of the laminate to a width of 25 mm and a length of 80 mm, and then bonding and fixing the surface of the piece to a glass substrate via an acrylic adhesive sheet. Then, using a tensile tester (RTF-1210 manufactured by A&D Co., Ltd.), one longitudinal end of the test piece (one side of the 25 mm width) was gripped and a 90° peel test (based on Japanese Industrial Standards (JIS) K 6854-1:1999 "Adhesives - Test method for peel adhesion strength - Part 1: 90° peel") was performed in an atmosphere of 23°C and 60% relative humidity at a crosshead speed (grip movement speed) of 200 mm / min.

[0220] The peelable support preferably contains polyethylene terephthalate (PET) as the main component (the component with the highest mass content among the components constituting the support). From the viewpoint of mechanical strength, the weight-average molecular weight of PET is preferably 20,000 or more, more preferably 30,000 or more, and even more preferably 40,000 or more. The weight-average molecular weight of PET can be determined by dissolving the support in hexafluoroisopropanol (HFIP) and using the GPC method described above. The thickness of the support is not particularly limited, but is preferably 0.1 to 100 μm, more preferably 0.1 to 75 μm, even more preferably 0.1 to 55 μm, and particularly preferably 0.1 to 10 μm. The support may also be subjected to known surface treatments such as corona treatment, glow discharge treatment, and undercoating.

[0221] Another example of an optical component is a laminate having a hard coat layer, a transparent support, and a pressure-sensitive adhesive layer or adhesive layer laminated in this order. Such a laminate is preferably used as an ultraviolet cut filter or a protective material (protective film, protective sheet). In this type of optical component, any of the support, the hard coat layer, and the pressure-sensitive adhesive layer or adhesive layer may contain the cured product of the present invention.

[0222] Examples of hard coat layers include those described in JP 2013-045045 A, JP 2013-043352 A, JP 2012-232459 A, JP 2012-128157 A, JP 2011-131409 A, JP 2011-131404 A, JP 2011-126162 A, JP 2011-075705 A, JP 2009-286981 A, JP 2009-263567 A, JP 2009 The hard coat layer described in JP-A-2007-075248, JP-A-2007-164206, JP-A-2006-096811, JP-A-2004-075970, JP-A-2002-156505, JP-A-2001-272503, WO 2012 / 018087, WO 2012 / 098967, WO 2012 / 086659, and WO 2011 / 105594 can be applied. The thickness of the hard coat layer is preferably 5 to 100 μm in order to further improve scratch resistance.

[0223] This optical component has a pressure-sensitive adhesive layer or bonding layer on the side of the supporting substrate opposite the side having the hard coat layer. The type of pressure-sensitive adhesive or bonding agent used in the pressure-sensitive adhesive or bonding layer is not particularly limited, and known pressure-sensitive adhesives or bonding agents can be used. It is also preferable to use a pressure-sensitive adhesive or bonding agent containing an acrylic resin described in paragraphs

[0056] to

[0076] of JP 2017-142412 A and a crosslinking agent described in paragraphs

[0077] to

[0082] of JP 2017-142412 A. The pressure-sensitive adhesive or bonding agent may also contain an adhesion improver (silane compound) described in paragraphs

[0088] to

[0097] of JP 2017-142412 A and an additive described in paragraph

[0098] of JP 2017-142412 A. The pressure-sensitive adhesive or bonding layer can be formed by the method described in paragraphs

[0099] to

[0100] of JP 2017-142412 A. The thickness of the adhesive layer or bonding layer is preferably 5 μm to 100 μm in terms of achieving both adhesive strength and ease of handling.

[0224] The optical member of the present invention can be preferably used as a component of displays such as liquid crystal displays (LCDs) and organic electroluminescence displays (OLEDs).

[0225] Examples of liquid crystal display devices include those containing the cured product of the present invention in components such as antireflection films, polarizing plate protective films, optical films, retardation films, pressure-sensitive adhesives, adhesives, etc. Optical components containing the cured product of the present invention may be placed on either the viewer side (front side) or the backlight side of the liquid crystal cell, and may also be placed on either the side of the polarizer farther from the liquid crystal cell (outer side) or the side closer to the liquid crystal cell (inner side).

[0226] Examples of organic electroluminescent display devices include those containing the cured product of the present invention in components such as optical films, polarizer protective films in circular polarizers, retardation films such as quarter-wave plates, adhesives, pressure-sensitive adhesives, etc. By using the cured product of the present invention in the above configuration, deterioration of the organic electroluminescent display device due to external light can be suppressed. [Example]

[0227] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In addition, in the structural formulas shown below, Me is a methyl group, and Et is an ethyl group.

[0228] <Synthesis example> (Synthesis Example 1) Synthesis of Compound A-1 Intermediate 1-1 was obtained in the same manner as described in paragraph 0285 of WO 2023 / 100715, except that malononitrile was used instead of ethyl cyanoacetate methacrylate. In a reaction vessel, 1.5 g of intermediate 1-1, 0.47 g of potassium carbonate, 0.82 g of 2-ethylhexyl bromide, and 150 ml of N,N-dimethylacetamide were added and mixed, followed by stirring at 60°C for 1 hour. After cooling to room temperature, 1 mL of hydrochloric acid and 150 ml of water were added to the reaction vessel and stirred for 30 minutes. The precipitated solid was collected by filtration, and then 200 ml of acetonitrile was added and heated to reflux under a nitrogen atmosphere for 1 hour. After cooling to room temperature and stirring at room temperature for 1 hour, the solid was collected by filtration and washed with 100 ml of acetonitrile, yielding 1.5 g of compound A-1 (yield 83%). Proton nuclear magnetic resonance 1 H-NMR (dDMSO): δ 11.3(s, 1H), 4.05(d, 2H), 3.73(m, 4H), 1.80(m, 1H), 1.35-1.25(m, 12H), 1.00-0.88(m, 12H) [ka]

[0229] (Synthesis example 2) Compound A-2 synthesis Compound A-2 (0.510 g, 84% yield) was obtained in the same manner as in Synthesis Example 1, except that 2-ethylhexyl bromide was replaced with 2-bromobutyrate and the reaction temperature was changed from 60°C to 5°C. 1 H-NMR (dDMSO): δ 11.4(s, 1H), 4.92(t, 1H), 4.19(t, 2H), 3.63(m, 4H), 2.02(m, 2H), 1.46(m, 4H), 1.21(m, 7H), 1.05(t, 3H), 0.87(t, 6H) [ka]

[0230] (Synthesis example 3) Compound A-3 synthesis Compound A-3 (0.450 g, yield 78%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate 1-2 was used instead of Intermediate 1-1 in Synthesis Example 1. 1H-NMR (dDMSO): δ 11.4(s, 1H), 7.89(d, 2H), 7.71(d, 2H), 4.05(d, 2H), 3.73(m, 4H), 1.80(m, 1H), 1.35-1.25(m, 12H), 1.00-0.88(m, 12H) [ka]

[0231] (Synthesis example 4) Compound A-4 synthesis Compound A-4 (0.440 g, 81% yield) was obtained in the same manner as in Synthesis Example 3, except that 2-ethylhexyl bromide was replaced with 2-bromobutyrate and the reaction temperature was changed from 60°C to 5°C. 1 H-NMR(dDMSO):δ 11.4(s, 1H), 7.89(d, 2H), 7.71(d, 2H), 4.92(t, 1H), 4.19(t, 2H), 3.63( m, 4H), 2.02(m, 2H), 1.46(m, 4H), 1.21(m, 7H), 1.05(t, 3H), 0.87(t, 6H) [ka]

[0232] (Synthesis example 5) Compound A-6 synthesis Compound A-6 (0.510 g, 85% yield) was obtained in the same manner as in Synthesis Example 4, except that Intermediate 1-3 was used instead of Intermediate 1-2. 1 H-NMR (dDMSO): δ 11.4(s, 1H), 4.92(t, 1H), 4.19(t, 2H), 3.63 (m, 8H), 2.02(m, 2H), 1.46(m, 8H), 1.21(m, 11H), 1.05(t, 3H), 0.87(t, 12H) [ka]

[0233] <About the compound> The exemplary compounds (1) to (6), comparative compound (1), and comparative compound (2) used in the following test examples each have the following structures: In the structural formulas shown below, Et is an ethyl group. [ka]

[0234] <Test Example 1> Measurement of absorbance and molar extinction coefficient 2 mg of each of the compounds (exemplified compounds (1) to (6)) listed in the table below was dissolved in 100 mL of ethyl acetate, and then diluted with ethyl acetate so that the absorbance of the solution was in the range of 0.6 to 1.2 to prepare sample solutions 101 to 106. Each sample solution was measured at its maximum absorption wavelength (λ ) using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation) in a 1 cm quartz cell. max ) and maximum absorption wavelength (λ max The molar extinction coefficient at 1000 kJ / cm2 was measured.

[0235] [Table 1]

[0236] Test Example 2: Evaluation of solubility 20 to 80 mg of the compounds shown in the table below (exemplary compounds (1) to (6), comparative compound (1), comparative compound (2)) were added to 40 mL of the solvent shown in the table below (MEK (methyl ethyl ketone), PGMEA (propylene glycol 1-monomethyl ether 2-acetate) or toluene). After stirring at 25°C for 30 minutes, it was visually confirmed whether the compounds had dissolved. -Evaluation criteria- A: The compound was completely dissolved when added in an amount of 80 mg. B: When the compound was added in an amount of 80 mg, some residue remained, but when the compound was added in an amount of 40 mg, it was completely dissolved. C: When the compound was added in an amount of 40 mg, some residue remained, but when the compound was added in an amount of 20 mg, it was completely dissolved. D: When the compound was added in an amount of 20 mg, some of the compound remained undissolved.

[0237] [Table 2]

[0238] As shown in the table above, in sample solutions 201 to 218 using exemplary compounds (1) to (6), each compound is completely dissolved in each solvent, and exemplary compounds (1) to (6) have excellent solvent solubility. In contrast, comparative compounds (1) and (2) remained undissolved and had insufficient solvent solubility.

[0239] <Test Example 3> A composition was prepared by mixing a compound shown in the table below (exemplary compounds (1) to (6), comparative compound (1), or comparative compound (2)), 3.0 g of an epoxy resin (EPPN-201, manufactured by Nippon Kayaku Co., Ltd.), 3.0 g of an epoxy resin (Epotohto ZX-1059, manufactured by Nippon Steel Chemical & Material Co., Ltd.), 4 g of a phenolic compound (KAYAHARD GPH-65, manufactured by Nippon Kayaku Co., Ltd.), 0.06 g of triphenylphosphine (a polymerization catalyst used as a heat curing aid), and 8 g of cyclohexanone. The composition was applied to a substrate so that the coating film had a thickness of 0.1 mm after drying and dried at 140°C for 10 minutes to form a coating film. The coating film was then vacuum-pressed (pressure: 5 MPa, temperature: 140°C, time: 20 minutes) and further heated at 150°C for 20 minutes to produce a sheet-shaped molded product.

[0240] (Hayes's review) The haze of the molded article was measured immediately after production. The measurement device used was a haze meter (model: NDH 7000) manufactured by Nippon Denshoku Industries Co., Ltd. The lower the measured haze value (%), the more excellent the transparency. The results are shown in the table below. The unit "%" is omitted from the evaluation results.

[0241] (Evaluation of light resistance) The molded body was subjected to a light resistance test under the following condition 1, and the maximum absorption wavelength (λ maxThe light resistance of the molded product was evaluated based on the following criteria: max After measuring the absorbance at λ, each molded body was subjected to a 3-week light resistance test under condition 1. max The absorbance at λ of each molded body was measured before and after the light resistance test. max Using the absorbance values ​​at 100°C, the absorbance retention rate (%) was calculated using the following formula, and light fastness was evaluated according to the following criteria. A higher absorbance retention rate indicates better light fastness. The evaluation results are shown in the table below. The number in parentheses in the light fastness column is the value of the absorbance retention rate. Absorbance retention rate (%) = (λ of each molded body after light resistance test) max Absorbance at / λ of each molded body before light resistance test max (absorbance at 1000 nm) × 100

[0242] -Condition 1- Equipment: Low-temperature cycle xenon weather meter (XL75, manufactured by Suga Test Instruments Co., Ltd.) Illuminance: 90klx (40w / m2) Time: 1 week Environment: 23°C, relative humidity 50%

[0243] -Evaluation criteria- AA: Absorbance retention rate is 90% or more A: Absorbance retention rate is 85% or more B: Absorbance retention rate is 80% or more and less than 85% C: Absorbance retention rate is less than 80%

[0244] (Evaluation of Solvent Resistance) The molded body was immersed in propylene glycol monomethyl ether acetate (PGMEA) for 10 minutes, and the maximum absorption wavelength (λ max ) was calculated, and the solvent resistance was evaluated according to the following criteria. A higher absorbance retention rate indicates better solvent resistance. The evaluation results are shown in the table below. The number in parentheses in the solvent resistance column is the value of the absorbance retention rate. Absorbance retention rate (%) = (λ of molded body after immersion in PGMEA max Absorbance at λ / λ of molded body before immersion in PGMEA max (absorbance at 1000 nm) × 100

[0245] -Evaluation criteria- AA: Absorbance retention rate is 95% or more A: Absorbance retention rate is 85% or more but less than 95% B: Absorbance retention rate is less than 85%

[0246] [Table 3]

[0247] As shown in the table above, the molded articles of the examples were free from precipitation of the exemplified compounds and had low haze. They also had excellent light resistance and solvent resistance. On the other hand, in Comparative Example 1 in which Exemplified Compound (1) was used, Comparative Compound (1) precipitated in the molded body, causing the molded body to turn white. In Comparative Example 2 using Exemplary Compound (2), Comparative Compound (2) was also precipitated in the molded article, and the haze was greater than in the Examples. Furthermore, Comparative Examples 1 and 2 were inferior to the Examples in light resistance and solvent resistance.

Claims

1. A composition comprising a compound represented by formula (1) and a curable compound; 【Chemical 1】 In formula (1), Q 1 represents a group represented by formula (Q-1); Q 2 is =O, =S, =NR q1 or =CR q2 R q3 represents R q1 ~R q3 each independently represents a hydrogen atom or a substituent, R q2 and R q3 may be bonded to each other to form a ring; R 1 is -O-Y 11 , -OC(=O)-Y 11 , -OC(=O)O-Y 11 , -OC(=O)NR y11 -Y 11 , -OSO 2 -Y 11 or a group containing a polymerizable group having an ethylenically unsaturated bond, R y11 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group; Y 11 represents an alkyl group, an aralkyl group, or an aryl group; 【Chemistry 2】 In formula (Q-1), * represents a bond, R 101 and R 102 each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

2. R in the formula (1) 1 is -O-Y 11 and Y 11 The composition of claim 1 , wherein is an alkyl group, an aralkyl group, or an aryl group.

3. The Y 11 The composition according to claim 2, wherein is an alkyl group having 2 to 30 carbon atoms.

4. Q in the formula (1) 2 is =CR q2 R q3 The composition according to claim 1 or 2,

5. The composition according to claim 1 or 2, wherein the curable compound comprises at least one selected from a resin and a polymerizable compound.

6. 3. The composition according to claim 1, wherein the curable compound contains a resin, and the resin is at least one selected from the group consisting of a (meth)acrylic resin, a polystyrene resin, a polyester resin, a polyurethane resin, a thiourethane resin, a polyimide resin, an epoxy resin, a polycarbonate resin, a phthalate resin, a cellulose acylate resin, and a cyclic olefin resin.

7. A cured product obtained by using the composition according to claim 1 or 2.

8. An optical component comprising the cured product according to claim 7 .

Citation Information

Patent Citations

  • Heterocyclic compound

    JP2009209126A