Composition, cured product, and optical member

Abstract

Disclosed is a composition comprising an ultraviolet absorber, a curable compound, and an anti-fading agent, the ultraviolet absorber comprising at least one selected from the group consisting of a compound represented by formula (1) and a polymer comprising a structure derived from the compound represented by formula (1), the anti-fading agent contains at least one compound selected from the group consisting of an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex, and a benzolactone compound. The invention also discloses a cured product and an optical component using the composition.

Description

Technical Field

[0001] The present invention relates to a composition containing an ultraviolet absorber, and also to a cured product and an optical component using the composition containing an ultraviolet absorber. Background Art

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

[0003] Previous technical literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Laid-Open No. 2009-067984 Summary of the Invention

[0006] Technical issues to be solved by the invention

[0007] One of the properties required of ultraviolet absorbers is low coloration. Furthermore, in recent years, high absorption capacity for ultraviolet rays with a relatively long wavelength of around 400 nm has also been required.

[0008] Furthermore, UV absorbers sometimes experience a decrease in their UV absorption performance over time due to light exposure. In particular, UV absorbers with a maximum absorption wavelength located on the longer wavelength side of the UV range tend to have poor light resistance and their UV absorption capacity tends to decrease over time. Therefore, in recent years, there has been a desire to further improve the light resistance of UV absorbers.

[0009] Therefore, an object of the present invention is to provide a composition capable of producing a cured product having excellent absorption of ultraviolet rays having a wavelength of around 400 nm, minimal coloration, and excellent light resistance. Another object of the present invention is to provide a cured product and an optical component.

[0010] Means for solving technical problems

[0011] The present inventors have conducted extensive research on compounds having a skeleton represented by formula (1) and have found that 1 and Q 2 Compounds with a specific structural combination exhibit excellent absorption of ultraviolet light near a wavelength of 400 nm, exhibit minimal coloration, and exhibit excellent light resistance. Further research has revealed that the combined use of this compound and a specified anti-fading agent can produce a film with minimal coloration even after prolonged light exposure, leading to the completion of the present invention. Accordingly, the present invention provides the following.

[0012] <1> A composition comprising an ultraviolet absorber, a curable compound and an anti-fading agent,

[0013] The ultraviolet absorber comprises at least one selected from the group consisting of a compound represented by formula (1) and a polymer comprising a structure derived from the compound represented by formula (1).

[0014] The anti-fading agent comprises at least one selected from the group consisting of an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex, and a benzolactone compound;

[0015] [Chemical Formula 1]

[0016]

[0017] In formula (1), Q 1 represents a group represented by formula (Q-1);

[0018] Q 2 Indicates =O, =S, =NR q1 or =CR q2 R q3 , R q1 ~R q3 Each independently represents a hydrogen atom or a substituent, R q2 With R q3 can be bonded to each other to form a ring, wherein R q2 With R q3 When the two groups are bonded to form a ring, =CR q2 R q3 With Q 1 Not the same structure;

[0019] R 1 and R 2 each independently represents a hydrogen atom or a substituent;

[0020] X 1 ~X 4 Each independently represents -S-, -NR X1 - or -SO2-, R X1 represents a hydrogen atom or an alkyl group;

[0021] [Chemical Formula 2]

[0022]

[0023] In formula (Q-1), * represents a connecting 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;

[0024] Among them, when R 101 or R 102 When any one of them is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond,

[0025] When R 101 or R 102 When any one of them is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 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,

[0026] When R 101 or R 102 When any one of them is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group having a substituent, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0027] <2> according to <1> The composition, wherein

[0028] The compound represented by the above formula (1) is a compound represented by formula (3);

[0029] [Chemical Formula 3]

[0030]

[0031] In formula (3), Q 3 represents a group represented by the above-mentioned formula (Q-1);

[0032] Q 4 Indicates =0, =S, =NR q11 or =CR q12 R q13 , R q11 ~R q13 Each independently represents a hydrogen atom or a substituent, R q12 With R q13 can be bonded to each other to form a ring, wherein R q12 With R q13 When the two groups are bonded to form a ring, =CR q12 R q13 With Q 3 Not the same structure;

[0033] R 11 and R 12 Each independently represents -OH, -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 olefinic 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.

[0034] <3> The composition according to <1> or <2>, wherein,

[0035] The aforementioned anti-fading agent contains at least one selected from the group consisting of a compound represented by formula (Ao1-1) and a compound represented by formula (Ao2-1);

[0036] [Chemical Formula 4]

[0037]

[0038] In formula (Ao1-1), R a1 ~R a4 each independently represents a hydrogen atom, an alkyl group or an alkenyl group,

[0039] X a1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group or an oxygen radical,

[0040] X a2 represents an atomic group required to form a 5- to 7-membered ring;

[0041] In formula (Ao2-1), R p1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group or -Si(R p101 )(R p102 )(R p103 ), R p101 ~R p103 each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group or an aryloxy group,

[0042] R p2 ~R p6 each independently represents a hydrogen atom or a substituent,

[0043] R p1 ~R p6 two adjacent groups can be bonded to each other to form a ring;

[0044] wherein, R p1 ~Rp6 not all of which are hydrogen atoms.

[0045] <4> The composition according to <1> or <2>, wherein

[0046] The aforementioned anti-fading agent contains at least one selected from the group consisting of a compound represented by formula (Ao1-2) and a compound represented by formula (Ao2-2);

[0047] [Chemical Formula 5]

[0048]

[0049] In formula (Ao1-2), X a11 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group, or an oxygen radical,

[0050] R a11 represents a substituent;

[0051] In formula (Ao2-2), R p11 ~R p14 each independently represents a hydrogen atom, an alkyl group, or an alkenyl group,

[0052] Y p11 represents an aryl group, a heteroaryl group, or a group containing an ethylenic unsaturated bond.

[0053] <5> The composition according to any one of <1> to <4>, wherein

[0054] The aforementioned curable compound contains at least one selected from the group consisting of a resin and a polymerizable compound.

[0055] <6> The composition according to any one of <1> to <4>, wherein

[0056] The aforementioned curable compound contains a resin, and the aforementioned 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.

[0057] <7> A cured product obtained using the composition according to any one of <1> to <6>.

[0058] <8> An optical component comprising <7> The solidified material.

[0059] Effects of the Invention

[0060] The present invention provides a composition capable of producing a cured product having excellent absorption of ultraviolet rays having a wavelength of approximately 400 nm, minimal coloration, and excellent light resistance. Furthermore, the present invention provides a cured product and an optical component. DETAILED DESCRIPTION

[0061] Hereinafter, the contents of the present invention will be described in detail.

[0062] In the notation of groups (atomic groups) in this specification, the notation not indicating "substituted" or "unsubstituted" includes both groups having no substituent and groups having substituent. For example, "alkyl" includes not only alkyl groups having no substituent (unsubstituted alkyl) but also alkyl groups having substituent (substituted alkyl).

[0063] In this specification, the numerical range expressed using "to" means a range including the numerical values ​​described before and after "to" as the lower limit and the upper limit.

[0064] In this specification, the total solid content means the total amount of components excluding the solvent from the total components of the resin composition.

[0065] In this specification, "(meth)acrylate" means both or either acrylate and methacrylate, "(meth)acrylic acid" means both or either acrylic acid and methacrylic acid, "(meth)allyl" means both or either allyl and methallyl, and "(meth)acryloyl" means both or either acryloyl and methacryloyl.

[0066] In this specification, the term "process" includes not only independent processes but also processes that cannot be clearly distinguished from other processes as long as the intended effect of the process can be achieved.

[0067] In this specification, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene-equivalent values ​​measured by gel permeation chromatography (GPC).

[0068] <Composition>

[0069] The composition of the present invention is characterized by comprising an ultraviolet absorber, a curable compound and an anti-fading agent.

[0070] The ultraviolet absorber comprises at least one selected from the group consisting of a compound represented by formula (1) and a polymer comprising a structure derived from the compound represented by formula (1).

[0071] The anti-fading agent includes at least one selected from the group consisting of amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds, and benzolactone compounds.

[0072] The compound represented by formula (1) and the polymer containing the structure derived from the compound represented by formula (1) are excellent compounds with excellent light resistance such as excellent absorption capacity of ultraviolet rays near a wavelength of 400nm, little coloration, and not easy to produce decomposition caused by light irradiation. As an ultraviolet absorber, the composition of the present invention comprising at least one selected from the compound represented by formula (1) and the polymer containing the structure derived from the compound represented by formula (1) can produce a cured product having excellent absorption capacity of ultraviolet rays near a wavelength of 400nm, little coloration, and excellent light resistance. Moreover, the composition of the present invention further comprises at least one anti-fading agent selected from amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds and benzolactone compounds, thereby suppressing the decomposition of the compound represented by formula (1) or the polymer containing the structure derived from the compound represented by formula (1) even if the film obtained using the composition is subjected to long-term light irradiation. Therefore, according to the composition of the present invention, a film with little coloration can be obtained even after long-term light irradiation.

[0073] Therefore, the composition of the present invention can produce a cured product having excellent absorption capability for ultraviolet rays having a wavelength of around 400 nm, little coloration, and excellent light resistance.

[0074] The composition of the present invention may be a composition in a solution state containing a solvent. Furthermore, the composition of the present invention may be a kneaded product. In addition, in this specification, a kneaded product refers to a substance obtained by kneading a UV absorber and a resin, wherein the UV absorber comprises at least one selected from a compound represented by formula (1) and a polymer comprising a structure derived from a compound represented by formula (1). That is, the kneaded product in this specification is a substance obtained by mixing and dispersing the UV absorber in the resin, and is different from a solution obtained by dissolving or dispersing the UV absorber and the resin in a solvent. Furthermore, when the composition of the present invention is a kneaded product, a substance containing a resin may be used in the curable compound.

[0075] The kneaded product is also preferably a pellet. In this specification, pellets refer to a material obtained by pelletizing a kneaded product into a specific shape such as a sphere, ellipsoid, cylinder, or prism. Furthermore, pellets are also preferably masterbatches. Masterbatches refer to a material in which a high concentration of an additive such as a UV absorber is dispersed in a resin and then mixed with a resin or the like at a predetermined ratio to form a molded body.

[0076] Hereinafter, each component contained in the composition of the present invention will be described.

[0077] <<Ultraviolet absorber>>

[0078] The composition of the present invention contains an ultraviolet absorber. Among the ultraviolet absorbers, a substance containing at least one selected from a compound represented by formula (1) and a polymer containing a structure derived from the compound represented by formula (1) can be used. The ultraviolet absorber preferably contains a compound represented by formula (1). Hereinafter, the compound represented by formula (1) is also referred to as a specific compound. In addition, a polymer containing a structure derived from the compound represented by formula (1) is also referred to as a specific polymer. In addition, the specific compound and the specific polymer are also collectively referred to as a specific ultraviolet absorber.

[0079] <<<Specific UV Absorbers>>>

[0080] (Compound represented by formula (1) (specific compound))

[0081] First, the compound represented by formula (1) (specific compound) will be described.

[0082] [Chemical Formula 6]

[0083]

[0084] In formula (1), Q 1 represents a group represented by formula (Q-1);

[0085] Q 2 Indicates =O, =S, =NR q1 or =CR q2 R q3 , R q1 ~R q3 Each independently represents a hydrogen atom or a substituent, R q2 With R q3 can be bonded to each other to form a ring, wherein R q2 With R q3 When the two groups are bonded to form a ring, =CR q2 R q3 With Q 1 Not the same structure;

[0086] R 1 and R 2 each independently represents a hydrogen atom or a substituent;

[0087] X 1 ~X 4 Each independently represents -S-, -NR X1 - or -SO2-, R X1 represents a hydrogen atom or an alkyl group;

[0088] [Chemical Formula 7]

[0089]

[0090] In formula (Q-1), * represents a connecting 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;

[0091] Among them, when R 101 or R 102 When any one of them is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond,

[0092] When R 101 or R 102 When any one of them is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 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,

[0093] When R 101 or R 102 When any one of them is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group having a substituent, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0094] -About R 1 、R 2 -

[0095] As R in formula (1) 1 and R 2 The substituents represented by include alkyl groups, aryl groups, aralkyl groups, heterocyclic groups, groups containing polymerizable groups having ethylenically unsaturated bonds, -OH, -OY 11 、-OC(=O)-Y 11 、-OC(=0)OY 11 、-OC(=O)NR y11 -Y 11 、-OSO2-Y 11 , cyano group, halogen atom, nitro group. 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.

[0096] The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. 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 those described in the substituent T described below.

[0097] The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, further 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 those described in the substituent T described below.

[0098] The alkyl portion of the aralkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5, and even more preferably 1 to 3 carbon atoms. The aryl portion of the aralkyl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, even more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8 carbon atoms. The aralkyl group may have a substituent. Examples of the substituent include the groups described below for the substituent T. Specific examples of the aralkyl group include benzyl and the like.

[0099] The heterocyclic ring in the above-mentioned heterocyclic group is preferably a saturated or unsaturated heterocyclic ring including 5 or 6 members. An aliphatic ring, an aromatic ring or other heterocyclic ring may be condensed in the heterocyclic ring. Examples of heteroatoms constituting the heterocyclic ring include B, N, O, S, Se and Te, preferably N, O and S. The carbon atoms of the heterocyclic ring preferably have a free valence (monovalent) (the heterocyclic group is bonded to a carbon atom). The preferred number of carbon atoms in the heterocyclic group is 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 pyrrolidine ring, morpholine ring, 2-boron-1,3-dioxolane and 1,3-tetrahydrothiazolidine ring. Examples of unsaturated heterocyclic rings in the heterocyclic group include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring.

[0100] Examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

[0101] Examples of the polymerizable group having an ethylenically unsaturated bond in the group containing a 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)acrylamido group, and a vinylphenyl group, with (meth)acryloyloxy group and vinylphenyl group being preferred.

[0102] As the group containing a polymerizable group having an ethylenically unsaturated bond, a group represented by the following formula (T1) can be mentioned.

[0103] *-X T1 -Y T1 -Z T1 …(T1)

[0104] In formula (T1), X T1represents a single bond, -O-, -OC(=O)-, -OC(=O)O- or -OC(=O)NRx 1 -, Rx 1 represents a hydrogen atom, an alkyl group or an aryl group,

[0105] Y T1 represents a single bond or a divalent linking group,

[0106] Z T1 It represents a polymerizable group having an ethylenically unsaturated bond.

[0107] Rx 1 The alkyl group represented by is preferably an alkyl group having 1 to 30 carbon atoms. Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, and n-butyl. 1 The aryl group represented by is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Specific examples include phenyl, p-tolyl, and naphthyl. 1 Preferred is a hydrogen atom.

[0108] X T1 It is preferably -O-, -OC(=O)- or -OC(=O)NH-, and more preferably -OC(=O)- from the viewpoint of synthesis.

[0109] As Y T1 The divalent linking group represented by the cation includes a hydrocarbon group and a group formed by bonding two or more hydrocarbon groups by a single bond or a linking group. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups, preferably aliphatic hydrocarbon groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be any of linear, branched, and cyclic. Furthermore, the cyclic aliphatic hydrocarbon group may be a monocyclic ring or a condensed ring. Furthermore, the cyclic aliphatic hydrocarbon group may have a cross-linked structure. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, 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, examples of the substituent include a hydroxyl group.

[0110] Examples of the linking group linking the two or more hydrocarbon groups mentioned above include -NH-, -S(=O)2-, -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -NHC(=O)-, and -C(=O)NH-, preferably -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -NHC(=O)-, or -C(=O)NH-.

[0111] As a Z T1As the polymerizable group represented by the ethylenically unsaturated bond, a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group can be given, and a (meth)acryloyloxy group and a vinylphenyl group are preferable.

[0112] As specific examples of the group represented by formula (T1), the groups represented by T-1 to T-32 below can be given. In the following structural formulas, Me is a methyl group, and * is a bonding site.

[0113] [Chemical Formula 8]

[0114]

[0115] [Chemical Formula 9]

[0116]

[0117] R of formula (1) 1 and R of formula (1) 2 are each independently -OH, -O-Y 11 , -OC(=O)-Y 11 , -OC(=O)O-Y 11 , -OC(=O)NR y11 -Y 11 , -OSO2-Y 11 , or a group containing a polymerizable group having an ethylenically unsaturated bond. R of formula (1) 1 and R of formula (1) 2 may be the same group, or different groups.

[0118] As one mode, R of formula (1) 1 and R of formula (1) 2 are each independently -OH, -O-Y 11 , -OC(=O)-Y 11 , -OC(=O)O-Y 11 , -OC(=O)NR y11 -Y 11 , or -OSO2-Y 11 . In this mode, R of formula (1) 1 and R of formula (1) 2 are each independently -OC(=O)-Y 11 , -O-Y 11 , or -OC(=O)NR y11 -Y 11 . R y11 is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. Y 11An alkyl group is preferred, a linear or branched alkyl group is more preferred, and a branched alkyl group is further preferred.

[0119] As another example, R 1 and R 2 At least one of the groups is a group containing a polymerizable group having an ethylenically unsaturated bond. According to this embodiment, an effect of suppressing bleeding into the film can be obtained.

[0120] As another example, R 1 and R 2 One of them is -OY 11 and the other is -OC(=O)-Y 11 way.

[0121] As another example, R 1 and R 2 One of them is -OY 11 or-OC(=O)-Y 11 Another embodiment is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0122] -About X 1 ~X 4 -

[0123] X in formula (1) 1 ~X 4 Each independently represents -S-, -NR X1 - or -SO2-, R X1 represents a hydrogen atom or an alkyl group. X1 The preferred range of the alkyl group represented by is the same as the above-mentioned alkyl group. X1 Preferred is a hydrogen atom.

[0124] In order to more significantly exhibit the effects of the present invention, X in formula (1) 1 ~X 4 Preferred is -S-.

[0125] -About Q 1 -

[0126] Q in formula (1) 1 represents a group represented by formula (Q-1).

[0127] 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.

[0128] Among them, when R 101 or R 102When any one of them is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group or a group containing a polymerizable group having an ethylenically unsaturated bond, when R 101 or R 102 When any one of them is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 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, when R 101 or R 102 When any one of them is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group having a substituent, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0129] R 101 and R 102 The number of carbon atoms in the alkyl group 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, preferably linear or branched. The alkyl group may have a substituent. Examples of the substituent include the groups described in the substituent T described below.

[0130] R 101 and R 102 The number of carbon atoms in the aryl group represented is preferably 6 to 30, more preferably 6 to 20, further 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 in the substituent T described below.

[0131] R 101 and R 102 The number of carbon atoms in the alkyl moiety of the aralkyl group represented is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The number of carbon atoms in the aryl moiety of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, even 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 described in the substituent T described below.

[0132] As R 101 and R 102 Examples of the heterocyclic group represented by include the above-mentioned heterocyclic groups.

[0133] As R 101 and R 102 Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include a group represented by formula (V1).

[0134] *-X V1 -Y V1-Z V1 …(V1)

[0135] In formula (V1), X V1 represents a single bond, -O-, -C(=O)-, -C(=O)O- or -C(=O)NRx 2 -, Rx 2 represents a hydrogen atom, an alkyl group or an aryl group,

[0136] Y V1 represents a single bond or a divalent linking group,

[0137] Z V1 It represents a polymerizable group having an ethylenically unsaturated bond.

[0138] Rx 2 The alkyl group and aryl group represented by the formula (T1) and the group Rx 1 The alkyl and aryl groups represented have the same meanings and the same preferred ranges. 2 Preferred is a hydrogen atom.

[0139] X V1 It is preferably a single bond or -C(=O)-, and more preferably a single bond.

[0140] As Y V1 The divalent linking group represented by can be exemplified by Y as a group represented by formula (T1): T1 The preferred ranges of the groups explained with reference to the divalent linking group represented by FIG. 1 are also the same.

[0141] As a Z V1 Examples of the polymerizable group of the ethylenically unsaturated bond 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.

[0142] Specific examples of the group represented by formula (V1) include the groups represented by the following V-1 to V-12: * in the following structural formula represents a connecting bond.

[0143] [Chemical Formula 10]

[0144]

[0145] As R in formula (Q-1) 101 and R 102 One way to do this is as follows: R 101 and R 102 each independently represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group,

[0146] When R 101or R 102 When any one of them is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group,

[0147] When R 101 or R 102 When any one of them is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group or a heterocyclic group,

[0148] When R 101 or R 102 When any one of them is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group having a substituent, or a heterocyclic group.

[0149] R in formula (Q-1) 101 and R 102 Each independently is preferably an alkyl group or an aralkyl group, more preferably an aralkyl group.

[0150] In R 101 and R 102 In the case of an alkyl group, R 101 and R 102 The alkyl groups represented are preferably each independently an alkyl group having 2 or more carbon atoms.

[0151] As R in formula (Q-1) 101 and R 102 Another embodiment of the present invention is R of formula (Q-1) 101 and R 102 At least one of the groups is a group containing a polymerizable group having an ethylenically unsaturated bond. According to this embodiment, an effect of suppressing bleeding into the film can be obtained.

[0152] -About Q 2 -

[0153] Q in formula (1) 2 Indicates =O, =S, =NR q1 or =CR q2 R q3 , R q1 ~R q3 Each independently represents a hydrogen atom or a substituent, R q2 With R q3 Can bond with each other to form a ring. q2 With R q3 When the two groups are bonded to form a ring, =CR q2 R q3 With Q 1 Not the same structure.

[0154] As R q1 ~R q3Examples of the substituents include cyano, carbamoyl, sulfamoyl, nitro, acyl, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, arylsulfinyl, alkoxycarbonyl, aryloxycarbonyl, alkyl, aryl, heterocyclic, and groups containing polymerizable groups having ethylenically unsaturated bonds. These groups may further have substituents. Examples of the substituents include the groups listed in the substituent T described below.

[0155] Examples of the carbamoyl group include 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.

[0156] Examples of the sulfamoyl group include a sulfamoyl group having 0 to 10 carbon atoms, preferably a sulfamoyl group having 2 to 8 carbon atoms, and more preferably a sulfamoyl group having 2 to 5 carbon atoms.

[0157] 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.

[0158] Examples of the alkylsulfonyl group include 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.

[0159] Examples of the arylsulfonyl group include arylsulfonyl groups having 6 to 20 carbon atoms, and an arylsulfonyl group having 6 to 10 carbon atoms is preferred.

[0160] Examples of the alkylsulfinyl group include 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.

[0161] Examples of the arylsulfinyl group include arylsulfinyl groups having 6 to 20 carbon atoms, and an arylsulfinyl group having 6 to 10 carbon atoms is preferred.

[0162] 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.

[0163] Examples of the aryloxycarbonyl group include aryloxycarbonyl groups having 6 to 20 carbon atoms, preferably aryloxycarbonyl groups having 6 to 12 carbon atoms, and more preferably aryloxycarbonyl groups having 6 to 8 carbon atoms.

[0164] Examples of the alkyl group include 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.

[0165] Examples of the aryl group include aryl groups having 6 to 20 carbon atoms, preferably aryl groups having 6 to 15 carbon atoms, and more preferably aryl groups having 6 to 10 carbon atoms.

[0166] The heterocyclic ring in the heterocyclic group preferably includes a 5-membered or 6-membered saturated or unsaturated heterocyclic ring. An aliphatic ring, an aromatic ring, or another heterocyclic ring may be condensed in the heterocyclic ring. Examples of heteroatoms constituting the heterocyclic ring include B, N, O, S, Se, and Te, preferably N, O, and S. The carbon atoms in the heterocyclic ring preferably have a free valence (monovalent) (the heterocyclic group is bonded to 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.

[0167] Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include a group represented by formula (U1).

[0168] *-X U1 -Y U1 -Z U1 …(U1)

[0169] In formula (U1), X U1 represents a single bond, -C(=O)-, -C(=O)O- or -C(=O)NRx 3 -, Rx 3 represents a hydrogen atom, an alkyl group or an aryl group,

[0170] Y U1 represents a single bond or a divalent linking group,

[0171] Z U1 It represents a polymerizable group having an ethylenically unsaturated bond.

[0172] Rx 3 The alkyl group and aryl group represented by the formula (T1) and the group Rx 1 The alkyl and aryl groups represented have the same meanings and the same preferred ranges. 3 Preferred is a hydrogen atom.

[0173] X U1 Preferably -C(=O)O- or -C(=O)NRx 3 -, and from the viewpoint of synthesis, -C(=O)O- is more preferable.

[0174] As Y U1 The divalent linking group represented by can be exemplified by Y as a group represented by formula (T1): T1 The preferred ranges of the groups explained with reference to the divalent linking group represented by FIG. 1 are also the same.

[0175] As a Z U1Examples of the polymerizable group of the ethylenically unsaturated bond 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.

[0176] Specific examples of the group represented by formula (U1) include the groups represented by the following U-1 to U-11: * in the following structural formula represents a connecting bond.

[0177] [Chemical Formula 11]

[0178]

[0179] In order to more significantly exhibit the effects of the present invention, Q in formula (1) 2 Preferably =CR q2 R q3 . And, preferably R q2 and R q3 At least one of them is an electron-withdrawing group, more preferably R q2 and R q3 It is an electron-withdrawing group.

[0180] R q2 and R q3 At least one of is also preferably a group containing a polymerizable group having an ethylenically unsaturated bond. In this embodiment, it is also preferred that R q2 and R q3 One of them is a group containing a polymerizable group having an ethylenically unsaturated bond, and the other is an electron-withdrawing group.

[0181] As electron-withdrawing groups, substituents having a Hammett substituent constant σp value of 0.2 or more can be cited. The Hammett substituent constant σ value is explained. Hammett's rule is an empirical rule proposed by LP Hammett in 1935 in order to quantitatively discuss the influence of substituents on the reaction or equilibrium of benzene derivatives, but its validity is now widely recognized. The substituent constants obtained by Hammett's rule include σp value and σm value, which can be found in many general books. For example, in "Lange's Handbook of Chemistry" 12th edition, 1979 (Mc Graw-Hill) or "Chemical Zone" Supplement, No. 122, pages 96-103, 1979 (Nankoutang), Chem. Rev., 1991, Vol. 91, pages 165-195, etc., detailed descriptions are given. In this specification, a substituent having a Hammett substituent constant σp value of 0.2 or more represents an electron-withdrawing group. The electron-withdrawing group preferably has a Hammett's substituent constant σp value of 0.25 or greater, more preferably has a Hammett's substituent constant σp value of 0.3 or greater, and further preferably has a Hammett's substituent constant σp value of 0.35 or greater.

[0182] Specific examples of groups having a Hammett substituent constant σp value of 0.2 or greater include a cyano group (σp value = 0.66), a carboxyl group (-COOH: σp value = 0.45), an alkoxycarbonyl group (-COOMe: σp value = 0.45), an aryloxycarbonyl group (-COOPh: σp value = 0.44), a carbamoyl group (-CONH2: σp value = 0.36), an alkylcarbonyl group (-COMe: σp value = 0.50), an arylcarbonyl group (-COPh: σp value = 0.43), an alkylsulfonyl group (-SO2Me: σp value = 0.72), and an arylsulfonyl group (-SO2Ph: σp value = 0.68). Me represents a methyl group, and Ph represents a phenyl group. The values ​​in parentheses are σp values ​​of representative substituents selected from Chem. Rev., 1991, Vol. 91, pp. 165-195.

[0183] R q2 and R q3 Preferably, each independently represents a hydrogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a nitro group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

[0184] As a way, we can cite R q2 and R q3Each of them is independently a hydrogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a nitro group, an alkoxycarbonyl group or an aryloxycarbonyl group. q2 and R q3 At least one of them is preferably a cyano group, an alkoxycarbonyl group, a nitro group or an alkylsulfonyl group, and R q2 and R q3 More preferably, each is independently a cyano group or an alkoxycarbonyl group. q2 and R q3 As another preferred embodiment, R q2 or R q3 An embodiment in which one of them is a cyano group and the other is an alkoxycarbonyl group.

[0185] As another way, R q2 and R q3 At least one of them is preferably a group containing a polymerizable group having an ethylenically unsaturated bond. q2 and R q3 Each of R q2 and R q3 One of them may be a group containing a polymerizable group having an ethylenically unsaturated bond, and the other may be an electron-withdrawing group.

[0186] In addition, in this manual, "in R q2 With R q3 When the two groups are bonded to form a ring, =CR q2 R q3 With Q 1 "Not the same structure" includes not only the case where a ring other than the structure represented by formula (Q-1) is formed, but also the case where a structure represented by formula (Q-1) is formed, but Rq in formula (Q-1) is not formed. 1 and Rq 2 The type is Q 1 In the case of a ring structure of a group of different types. That is, Q 2 For Q 1 Groups of different structures.

[0187] =CR q2 R q3 R q2 With R q3In the case of being bonded to each other and forming a ring, from the reason of more significantly playing the effect of the present invention, the ring formed is preferably the ring except the structure represented by formula (Q-1).As the ring except the structure represented by formula (Q-1), cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, pyrrolidine ring, tetrahydrofuran ring, tetrahydrothiophene ring, oxazoline ring, thiazoline ring, pyrroline ring, pyrazoline ring, imidazoline ring, imidazoline ring, piperidine ring, piperazine ring, pyran ring, indandione ring etc. can be enumerated.These can have substituent in any position.

[0188] R in formula (1) 1 、R 2 , Q 1 and Q 2 At least one of them preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond, R 1 、R 2 , Q 1 and Q 2 More preferably, one or both of them contain a polymerizable group having an ethylenically unsaturated bond.

[0189] Furthermore, Q in formula (1) 2 =CR q2 R q3 , R 1 、R 2 、R q2 、R q3 、R 101 and R 102 At least one of the groups is preferably a group containing a polymerizable group having an ethylenically unsaturated bond, R 1 、R 2 、R q2 、R q3 、R 101 and R 102 More preferably, one or both of them contain a polymerizable group having an ethylenically unsaturated bond.

[0190] Furthermore, the number of polymerizable groups having an ethylenically unsaturated bond contained in formula (1) is preferably 1 or 2.

[0191] The specific compound is preferably a compound represented by formula (3).

[0192] [Chemical Formula 12]

[0193]

[0194] In formula (3), Q3 represents a group represented by the above formula (Q-1);

[0195] Q 4represents =0, =S, =NR q11 or =CR q12 R q13 , 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; wherein, in the case where R q12 and R q13 are bonded to each other to form a ring, =CR q12 R q13 and Q 3 are not the same structure.

[0196] R 11 and R 12 each independently represents -OH, -O-Y 11 , -OC(=O)-Y 11 , -OC(=O)O-Y 11 , -OC(=O)NR y11 -Y 11 , -OSO2-Y 11 or a group containing a polymerizable group having an olefinic 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.

[0197] Q 3 and Q 4 of formula (3) have the same meaning as Q 1 and Q 2 of formula (1), and the same preferable range. Also, the preferable ranges of R y11 and Y 11 in formula (3) are the same as the meanings of R y11 and Y 11 described in formula (1).

[0198] As one mode, there can be mentioned a mode in which R 11 and R 12 each independently are -OH, -O-Y 11 , -OC(=O)-Y 11 , -OC(=O)O-Y 11 , -OC(=O)NR y11 -Y 11 or -OSO2-Y 11 . In this mode, R 11 and R 12 are preferably each independently -OC(=O)-Y 11 , -O-Y 11 or -OC(=0)NRy11 -Y 11 .

[0199] As another example, R 11 and R 12 At least one of them is an embodiment of a group containing a polymerizable group having an ethylenically unsaturated bond.

[0200] As another example, R 11 and R 12 One of them is -OY 11 and the other is -OC(=O)-Y 11 way.

[0201] As another example, R 11 and R 12 One of them is -OY 11 or-OC(=O)-Y 11 Another embodiment is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0202] R in formula (3) 11 、R 12 , Q 3 and Q 4 At least one of them preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond, R 11 、R 12 , Q 3 and Q 4 More preferably, one or both of them contain a polymerizable group having an ethylenically unsaturated bond.

[0203] Furthermore, Q in formula (3) 4 =CR q12 R q13 , R 11 、R 12 、R q12 、R q13 、R 101 and R 102 At least one of the groups is preferably a group containing a polymerizable group having an ethylenically unsaturated bond, R 11 、R 12 、R q12 、R q13 、R 101 and R 102 More preferably, one or both of them contain a polymerizable group having an ethylenically unsaturated bond.

[0204] The number of polymerizable groups having an ethylenically unsaturated bond contained in formula (3) is preferably 1 or 2.

[0205] The specific compound is preferably a compound represented by formula (6).

[0206] [Chemical Formula 13]

[0207]

[0208] In formula (6), Q 5 represents a group represented by the above formula (Q-1),

[0209] Q 6 represents =0, =S, =NR q21 or =CR q22 R q23 ,

[0210] R q21 ~R q23 each independently represents a hydrogen atom or a substituent, R q22 and R q23 may be bonded to each other to form a ring; wherein, in the case where R q22 and R q23 are bonded to each other to form a ring, =CR q22 R q23 and Q 5 are not the same structure.

[0211] R 61 and R 62 each independently represents -O-Y 61 , -OC(=O)-Y 61 , -OC(=O)O-Y 61 , -OC(=O)NR y61 -Y 61 or -OSO2-Y 61 , R y61 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, Y 61 represents an alkyl group, an aralkyl group or an aryl group.

[0212] Q 5 and Q 6 of formula (6) have the same meaning as Q 1 and Q 2 of formula (1), and the preferable range is also the same. Also, the preferable range of R y61 and Y 61 in formula (6) is the same as the meaning of R y11 and Y 11 described in formula (1).

[0213] R 61 and R 62 of formula (6) are preferably each independently -OC(=O)-Y 11 , -O-Y11 or -OC(=O)NR y11 -Y 11 .

[0214] R in formula (6) 61 and R 62 They may be the same group or different groups.

[0215] (Substituent T)

[0216] As the substituent T, the following groups can be mentioned.

[0217] Halogen atoms (e.g., chlorine, bromine, and iodine);

[0218] Alkyl groups [straight-chain, branched, or cyclic alkyl groups. Specifically, straight-chain or branched alkyl groups (preferably straight-chain or branched alkyl groups having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, tert-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 in which one hydrogen atom is removed from a bicycloalkane having 5 to 30 carbon atoms, such as bicyclo[1,2,2]heptane-2-yl and bicyclo[2,2,2]octan-3-yl), and tricyclic structures having multiple ring structures are also included. The alkyl groups in the substituents described below (for example, alkyl groups in alkylthio groups) also represent alkyl groups of this concept.];

[0219] Alkenyl [straight-chain, branched-chain, or cyclic alkenyl. Specifically, a straight-chain or branched alkenyl (preferably a straight-chain or branched alkenyl having 2 to 30 carbon atoms, such as vinyl, allyl, isoprenyl, geranyl, and oleyl), a cycloalkenyl (preferably a cycloalkenyl having 3 to 30 carbon atoms. That is, a monovalent group obtained by removing one hydrogen atom from a cycloolefin having 3 to 30 carbon atoms. For example, 2-cyclopenten-1-yl and 2-cyclohexen-1-yl), a bicycloalkenyl (preferably a bicycloalkenyl having 5 to 30 carbon atoms. That is, a monovalent group obtained by removing one hydrogen atom from a bicycloolefin having one double bond. For example, it includes bicyclo[2,2,1]hept-2-en-1-yl and bicyclo[2,2,2]oct-2-en-4-yl).];

[0220] Alkynyl (preferably a straight-chain or branched alkynyl group having 2 to 30 carbon atoms, such as ethynyl and propargyl);

[0221] an aryl group (preferably an aryl group having 6 to 30 carbon atoms, for example, phenyl, p-tolyl, naphthyl, m-chlorophenyl, or o-hexadecanoylaminophenyl);

[0222] Heterocyclic group (preferably a monovalent group obtained by removing one hydrogen atom from a 5-membered or 6-membered aromatic or non-aromatic heterocyclic compound, more preferably a 5-membered or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms. For example, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl);

[0223] cyano group;

[0224] hydroxyl group;

[0225] Nitro;

[0226] carboxyl;

[0227] 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 tert-butoxy group, an n-octyloxy group, and a 2-methoxyethoxy group);

[0228] an aryloxy group (preferably an aryloxy group having 6 to 30 carbon atoms, for example, a phenoxy group, a 2-methylphenoxy group, a 4-tert-butylphenoxy group, a 3-nitrophenoxy group, and a 2-tetradecanoylaminophenoxy group);

[0229] a heterocyclic oxy group (preferably a heterocyclic oxy group having 2 to 30 carbon atoms, for example, 1-phenyltetrazol-5-oxy and 2-tetrahydropyranyloxy);

[0230] an acyloxy group (preferably a formyloxy group, an alkylcarbonyloxy group having 2 to 30 carbon atoms, or an arylcarbonyloxy group having 6 to 30 carbon atoms, such as a formyloxy group, an acetoxy group, a pivaloyloxy group, a stearoyloxy group, a benzoyloxy group, or a p-methoxyphenylcarbonyloxy group);

[0231] a carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms, for example, N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy, morpholinylcarbonyloxy, N,N-di-n-octylaminocarbonyloxy, and N-n-octylcarbamoyloxy);

[0232] an alkoxycarbonyloxy group (preferably an alkoxycarbonyloxy group having 2 to 30 carbon atoms, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a tert-butoxycarbonyloxy group, and an n-octylcarbonyloxy group);

[0233] an aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, a phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, and a p-n-hexadecyloxyphenoxycarbonyloxy group);

[0234] amino group (preferably an amino group, an alkylamino group having 1 to 30 carbon atoms, or an phenylamino group having 6 to 30 carbon atoms. For example, an amino group, a methylamino group, a dimethylamino group, an phenylamino group, an N-methyl-phenylamino group, or a diphenylamino group);

[0235] Acylamino (preferably formylamino, alkylcarbonylamino having 2 to 30 carbon atoms, or arylcarbonylamino having 6 to 30 carbon atoms. For example, formylamino, acetylamino, trimethylacetylamino, lauroylamino, benzylamino, and 3,4,5-tri-n-octyloxyphenylcarbonylamino);

[0236] aminocarbonylamino group (preferably an aminocarbonylamino group having 1 to 30 carbon atoms, for example, carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino, and morpholinylcarbonylamino);

[0237] an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a tert-butoxycarbonylamino group, a n-octadecyloxycarbonylamino group, and an N-methyl-methoxycarbonylamino group);

[0238] an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, and a m-n-octyloxyphenoxycarbonylamino group);

[0239] Amine sulfonylamino group (preferably an amine sulfonylamino group having 0 to 30 carbon atoms, such as amine sulfonylamino, N,N-dimethylaminosulfonylamino, and N-octylaminosulfonylamino);

[0240] 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, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, 2,3,5-trichlorophenylsulfonylamino, and p-methylphenylsulfonylamino);

[0241] thiol;

[0242] an alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms, such as methylthio, ethylthio, and n-hexadecylthio);

[0243] an arylthio group (preferably an arylthio group having 6 to 30 carbon atoms, for example, a phenylthio group, a p-chlorophenylthio group, and a m-methoxyphenylthio group);

[0244] a heterocyclic thio group (preferably a heterocyclic thio group having 2 to 30 carbon atoms, for example, a 2-benzothiazolylthio group and a 1-phenyltetrazol-5-ylthio group);

[0245] A sulfonamide group (preferably a sulfonamide group having 0 to 30 carbon atoms, for example, N-ethylsulfonamide, N-(3-dodecyloxypropyl)sulfonamide, N,N-dimethylsulfonamide, N-acetamidesulfonyl, N-benzamidesulfonyl, and N-(N'-phenylcarbamoyl)sulfonamide);

[0246] sulfonic acid;

[0247] an alkylsulfinyl group or an arylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms or an arylsulfinyl group having 6 to 30 carbon atoms, for example, methylsulfinyl, ethylsulfinyl, phenylsulfinyl, and p-methylphenylsulfinyl);

[0248] 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);

[0249] acyl group (preferably a formyl group, an alkylcarbonyl group having 2 to 30 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, or a heterocyclic carbonyl group bonded to a carbonyl group via a carbon atom having 4 to 30 carbon atoms. For example, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, p-n-octyloxyphenylcarbonyl, 2-pyridylcarbonyl, and 2-furylcarbonyl);

[0250] 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, and a p-tert-butylphenoxycarbonyl group);

[0251] an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group, and an n-octadecyloxycarbonyl group);

[0252] 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, and an N-(methylsulfonyl)carbamoyl group);

[0253] an aryl or heterocyclic azo group (preferably an arylazo 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, and a 5-ethylthio-1,3,4-thiadiazol-2-ylazo group);

[0254] an imido group (preferably an N-succinimidyl group or an N-phthalimido group);

[0255] Phosphino group (preferably a phosphino group having 2 to 30 carbon atoms, such as dimethylphosphino, diphenylphosphino, and methylphenoxyphosphino)

[0256] a phosphono group (preferably a phosphono group having 2 to 30 carbon atoms, for example, a phosphono group, a dioctyloxyphosphono group, and a diethoxyphosphono group);

[0257] a phosphonooxy group (preferably a phosphonooxy group having 2 to 30 carbon atoms, for example, a diphenoxyphosphonooxy group and a dioctyloxyphosphonooxy group);

[0258] A phosphonylamino group (preferably a phosphonylamino group having 2 to 30 carbon atoms, such as a dimethoxyphosphonylamino group and a dimethylaminophosphonylamino group);

[0259] Among the groups listed above, for groups having hydrogen atoms, one or more hydrogen atoms may be substituted by 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.

[0260] As specific examples of the specific compound, the compound of the following structure can be cited. In the structural formula shown below, Et is an ethyl group, Me is a methyl group, n Bu is n-butyl, t Bu is tert-butyl, and Ph is phenyl.

[0261] [Chemical Formula 14]

[0262]

[0263] [Chemical Formula 15]

[0264]

[0265] [Chemical Formula 16]

[0266]

[0267] [Chemical Formula 17]

[0268]

[0269] [Chemical Formula 18]

[0270]

[0271] [Chemical Formula 19]

[0272]

[0273] [Chemical Formula 20]

[0274]

[0275] [Chemical Formula 21]

[0276]

[0277] [Chemical Formula 22]

[0278]

[0279] [Chemical Formula 23]

[0280]

[0281] [Chemical Formula 24]

[0282]

[0283] [Chemical Formula 25]

[0284]

[0285] [Chemical Formula 26]

[0286]

[0287] [Chemical Formula 27]

[0288]

[0289] [Chemical Formula 28]

[0290]

[0291] [Chemical Formula 29]

[0292]

[0293] [Chemical Formula 30]

[0294]

[0295] [Chemical Formula 31]

[0296]

[0297] [Chemical Formula 32]

[0298]

[0299] [Chemical Formula 33]

[0300]

[0301] [Chemical Formula 34]

[0302]

[0303] [Chemical Formula 35]

[0304]

[0305] [Chemical Formula 36]

[0306]

[0307] [Chemical Formula 37]

[0308]

[0309] [Chemical Formula 38]

[0310]

[0311] [Chemical Formula 39]

[0312]

[0313] [Chemical Formula 40]

[0314]

[0315] [Chemical Formula 41]

[0316]

[0317] [Chemical Formula 42]

[0318]

[0319] [Chemical Formula 43]

[0320]

[0321] [Chemical Formula 44]

[0322]

[0323] [Chemical Formula 45]

[0324]

[0325] [Chemical Formula 46]

[0326]

[0327] [Chemical Formula 47]

[0328]

[0329] [Chemical Formula 48]

[0330]

[0331] [Chemical Formula 49]

[0332]

[0333] [Chemical Formula 50]

[0334]

[0335] [Chemical Formula 51]

[0336]

[0337] [Chemical Formula 52]

[0338]

[0339] [Chemical Formula 53]

[0340]

[0341] [Chemical Formula 54]

[0342]

[0343] [Chemical Formula 55]

[0344]

[0345] [Chemical Formula 56]

[0346]

[0347] [Chemical Formula 57]

[0348]

[0349] [Chemical Formula 58]

[0350]

[0351] [Chemical Formula 59]

[0352]

[0353] [Chemical Formula 60]

[0354]

[0355] [Chemical Formula 61]

[0356]

[0357] [Chemical Formula 62]

[0358]

[0359] [Chemical Formula 63]

[0360]

[0361] [Chemical Formula 64]

[0362]

[0363] [Chemical Formula 65]

[0364]

[0365] The specific compound preferably has an absorption maximum wavelength in the range of 380 to 420 nm, more preferably in the range of 390 to 410 nm.

[0366] The specific compound preferably has a ratio of absorbance at a wavelength of 440 nm to absorbance at a wavelength of 400 nm of less than 0.02.

[0367] The specific compound preferably has a molar absorption coefficient at the absorption maximum wavelength of 80,000 L / mol-cm or more, more preferably 85,000 L / mol-cm or more, and further preferably 90,000 L / mol-cm or more.

[0368] Further, the specific compound preferably has a molar absorption coefficient at a wavelength of 400 nm of 30,000 L / mol-cm or more, more preferably 40,000 L / mol-cm or more, and further preferably 50,000 L / mol-cm or more.

[0369] Further, the specific compound preferably has a molar absorption coefficient at a wavelength of 440 nm of 1,000 L / mol-cm or less, more preferably 800 L / mol-cm or less, and further preferably 600 L / mol-cm or less.

[0370] The absorbance, absorption maximum wavelength, and molar absorption coefficient of the specific compound can be determined by measuring the spectrum of a solution prepared by dissolving the specific compound in ethyl acetate using a 1-cm quartz cell at room temperature (25°C). As a measuring device, a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation) or the like can be used.

[0371] The specific compound can be produced according to the method described in International Publication No. 2009 / 022736.

[0372] Further, in the specific compound, the compound represented by formula (6) can also be produced by reacting the compound represented by formula (4) with the compound represented by formula (5).

[0373] [Chemical Formula 66]

[0374]

[0375] In formula (4), Q 5 represents a group represented by the above formula (Q-1),

[0376] Q 6 Indicates =O, =S, =NR q21 or =CR q22 R q23 ,

[0377] R q21 ~R q23 Each independently represents a hydrogen atom or a substituent, R q22 With R q23 can bond with each other to form a ring; wherein, in R q22 With R q23 When the two groups are bonded to form a ring, =CR q22 R q23 With Q 5 Not the same structure.

[0378] In formula (5), E 51 Indicates -COCl, -O(C=O)Cl, -NR e51 (C=O)Cl, -NCO, -Cl, -Br, -I or -SO2R e52 ,

[0379] R e51 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group,

[0380] R e52 represents -Cl or alkoxy,

[0381] Y 51 represents an alkyl group, an aralkyl group or an aryl group.

[0382] Q in formula (4) 5 and Q 6 And Q in formula (6) 5 and Q 6 The meanings and preferred ranges are the same.

[0383] Y in formula (5) 51 The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. 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 those described above for the substituent T.

[0384] Y in formula (5) 51 The number of carbon atoms in the aryl group represented is preferably 6 to 30, more preferably 6 to 20, further 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 above for the substituent T.

[0385] Y in formula (5) 51 The number of carbon atoms in the alkyl moiety of the aralkyl group represented is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The number of carbon atoms in the aryl moiety of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, even 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 described above for the substituent T.

[0386] Y in formula (5) 51 An alkyl group is preferred.

[0387] E in formula (5) 51 R in e51 The alkyl, aralkyl and aryl groups represented by the formula (5) are 51 The groups described in are the same.

[0388] E in formula (5) 51 R in e52 The number of carbon atoms in the alkoxy group represented is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.

[0389] The reaction of the compound represented by formula (4) with the compound represented by formula (5) can be carried out in an organic solvent. The organic solvent is not particularly limited, and preferably includes, for example, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone and other amide solvents, tetrahydrofuran, acetonitrile, toluene, methanol, ethanol, isopropanol and a mixture thereof, and particularly preferably dimethylformamide or dimethylacetamide. In addition, the reaction ratio of the compound represented by formula (4) and the compound represented by formula (5) can be appropriately set according to the desired structure of the compound represented by formula (6). The reaction temperature is not particularly limited, and for example, it is preferably 0°C to the boiling point of the reaction solvent. The reaction time is not particularly limited, and for example, it can be set to 1 hour to 48 hours.

[0390] (Polymer (specific polymer) containing a structure derived from a compound represented by formula (1))

[0391] A polymer (specific polymer) containing a structure derived from the compound represented by formula (1) can also be used as the ultraviolet absorber.

[0392] The specific polymer preferably contains R 1 、R 2 , Q 1 and Q 2The structure of the compound in which at least one of the structures is a structure containing a polymerizable group having an ethylenically unsaturated bond (hereinafter also referred to as structure (1)), more preferably containing a structure derived from R in the compound represented by the above formula (3) 11 、R 12 , Q 3 and Q 4 The structure of the compound in which at least one of the structures is a group containing a polymerizable group having an ethylenically unsaturated bond (hereinafter also referred to as structure (3)).

[0393] The specific polymer may contain, in addition to the structure derived from the compound represented by formula (1), a structure derived from a compound having a group containing an ethylenically unsaturated bond other than the compound represented by formula (1) (hereinafter also referred to as other polymerizable compounds). 1 、R 2 , Q 1 and Q 2 A copolymer of a compound represented by formula (1) having a structure in which at least one of the compounds is a polymerizable group containing an ethylenically unsaturated bond and other polymerizable compounds. Examples of other polymerizable compounds include the polymerizable compounds described as materials for the composition of the present invention described later. Furthermore, among other polymerizable compounds, ultraviolet absorbers having polymerizable groups other than the compound represented by formula (1) (also referred to as other polymerizable ultraviolet absorbers) can also be used.

[0394] Examples of polymerizable groups possessed by other polymerizable UV absorbers include vinyl, allyl, (meth)acryloyl, (meth)acryloyloxy, (meth)acrylamido, and vinylphenyl. Examples of other polymerizable UV absorbers include aminobutadiene compounds, dibenzoylmethane compounds, benzophenone compounds, benzotriazole compounds, and hydroxyphenyltriazine compounds.

[0395] The content of the structure derived from the compound represented by formula (1) in the specific polymer is preferably 0.01 to 100 mass %, with the upper limit being more preferably 50 mass % or less, and even more preferably 30 mass % or less, and the lower limit being more preferably 0.02 mass % or more, and even more preferably 0.1 mass % or more.

[0396] The weight average molecular weight of the specific polymer is preferably 5,000 to 150,000, more preferably 10,000 to 120,000, and even more preferably 20,000 to 100,000.

[0397] <<<Other UV absorbers>>>

[0398] The composition of the present invention may contain an ultraviolet absorber other than the above-mentioned specific ultraviolet absorber (hereinafter also referred to as other ultraviolet absorber). According to this embodiment, a cured product that blocks light of a wavelength in a wide range of the ultraviolet region can be formed.

[0399] The maximum absorption wavelength of other ultraviolet absorbers is preferably within the wavelength range of 300 to 380 nm, more preferably within the wavelength range of 300 to 370 nm, further preferably within the wavelength range of 310 to 360 nm, and particularly preferably within the wavelength range of 310 to 350 nm.

[0400] Other ultraviolet absorbers are also preferably compounds having a polymerizable group. Examples of the polymerizable group include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group.

[0401] Examples of other UV absorbers include aminobutadiene-based UV absorbers, dibenzoylmethane-based UV absorbers, benzotriazole-based UV absorbers, benzophenone-based UV absorbers, salicylic acid-based UV absorbers, acrylate-based UV absorbers, and triazine-based UV absorbers. Benzotriazole-based UV absorbers, benzophenone-based UV absorbers, and triazine-based UV absorbers are preferred, and benzotriazole-based UV absorbers and triazine-based UV absorbers are more preferred. Specific examples of other UV absorbers include the compounds described in the Examples below. In addition, other ultraviolet absorbers can be used, for example, those described in paragraphs 0065 to 0070 of Japanese Patent Application Laid-Open No. 2009-263616, paragraph 0065 of International Publication No. 2017 / 122503, Japanese Patent Application Laid-Open No. 2003-128730, Japanese Patent Application Laid-Open No. 2003-129033, Japanese Patent Application Laid-Open No. 2014-077076, Japanese Patent Application Laid-Open No. 2015-164994, Japanese Patent Application Laid-Open No. 2015-168822, Japanese Patent Application Laid-Open No. 2018-135282, Japanese Patent Application Laid-Open No. 2018-168089, Japanese Patent Application Laid-Open No. 2018-168278, Japanese Patent Application Laid-Open No. 2018-188589, Japanese Patent Application Laid-Open No. 2019-001767, Japanese Patent Application Laid-Open No. 20 Compounds described in Japanese Patent Application Publication No. 20-023697, Japanese Patent Application Laid-Open No. 2020-041013, Japanese Patent No. 5518613, Japanese Patent No. 5868465, Japanese Patent No. 6301526, Japanese Patent No. 6354665, Japanese Patent Translation No. 2017-503905, International Publication No. 2015 / 064674, International Publication No. 2015 / 064675, International Publication No. 2017 / 102675, International Publication No. 2018 / 190281, International Publication No. 2018 / 216750, International Publication No. 2019 / 087983, European Patent No. 2379512, European Patent No. 2951163, etc.

[0402] The content of the ultraviolet absorber in the total solid content of the composition is preferably 0.01 to 95% by mass. The lower limit can be set to 0.05% by mass or more, can be set to 0.1% by mass or more, can also be set to 1% by mass or more, can also be set to 5% by mass or more, can also be set to 10% by mass or more, can also be set to 20% by mass or more, can also be set to 25% by mass or more, can also be set to 30% by mass or more. The upper limit can be set to 90% by mass or less, can also be set to 80% by mass or less, can also be set to 70% by mass or less, can also be set to 60% by mass or less, can also be set to 50% by mass or less, can also be set to 40% by mass or less, can also be set to 30% by mass or less, can also be set to 20% by mass or less. The content of the specific ultraviolet absorber in the ultraviolet absorber is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 20% by mass or more. The upper limit can be set to 100% by mass or less, can also be set to 75% by mass or less, and can also be set to 50% by mass or less.

[0403] The content of the specific ultraviolet absorber in the total solids content of the composition is preferably 0.01 to 50% by mass. The lower limit is preferably 0.05% by mass or more, 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.

[0404] When the above-mentioned specific compound (the compound represented by formula (1)) is used as the specific ultraviolet absorber, the content of the specific compound 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, 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.

[0405] When the above-mentioned specific polymer (including a polymer having a structure derived from a compound represented by formula (1)) is used as the specific ultraviolet absorber, the content of the specific polymer in the total solid content of the composition is preferably 10 to 95% by mass. The lower limit is preferably 15% by mass or more, more preferably 25% by mass or more. The upper limit is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 75% by mass or less.

[0406] The composition of the present invention may contain only one ultraviolet absorber or may contain two or more ultraviolet absorbers. When containing two or more ultraviolet absorbers, the total amount thereof is preferably within the above range.

[0407] <<Anti-fading agent>>

[0408] The composition of the present invention includes an anti-fading agent. The anti-fading agent may include at least one selected from an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex, and a benzolactone compound. The amine compound is preferably a hydroxylamine compound, a tertiary amine compound, or an aminooxy compound, more preferably a tertiary amine compound or an aminooxy compound. The metal complex is preferably a nickel complex or a cobalt complex, more preferably a nickel complex. The anti-fading agent is preferably at least one selected from an amine compound and a benzolactone compound, more preferably an amine compound.

[0409] The anti-fading agent preferably contains at least one selected from the group consisting of the compound represented by formula (Ao1-1) and the compound represented by formula (Ao2-1), and more preferably contains the compound represented by formula (Ao1-1).

[0410] [Chemical Formula 67]

[0411]

[0412] In formula (Ao1-1), R a1 ~R a4 each independently represents a hydrogen atom, an alkyl group or an alkenyl group,

[0413] X a1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group or an oxygen free radical,

[0414] X a2 represents the atomic groups required to form a 5- to 7-membered ring;

[0415] In formula (Ao2-1), R p1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or -Si(R p101 )(R p102 )(R p103 ), R p101 ~R p103 each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group or an aryloxy group,

[0416] R p2 ~R p6 each independently represents a hydrogen atom or a substituent,

[0417] R p1 ~Rp6 Two adjacent groups in the group can be bonded to each other to form a ring;

[0418] Among them, R p1 ~R p6 Not all of them are hydrogen atoms.

[0419] The above-mentioned groups in formula (Ao1-1) and formula (Ao1-2) may have a substituent. Examples of the substituent include the groups exemplified in the substituent T described above.

[0420] -Regarding the compound represented by formula (Ao1-1)-

[0421] R in formula (Ao1-1) a1 ~R a4 Each independently is preferably an alkyl group or an alkenyl group, more preferably an alkyl group.

[0422] The number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, but is preferably linear. The alkyl group may have a substituent. Examples of the substituent include those listed above for the substituent T.

[0423] The number of carbon atoms in the alkenyl group is preferably 2 to 5, more preferably 2 or 3. The alkenyl group is preferably linear or branched, more preferably linear. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0424] R a1 ~R a4 A methyl group is particularly preferred.

[0425] X in formula (Ao1-1) a1 It is preferably a hydrogen atom, an oxygen radical, an alkyl group, an alkoxy group, an alkenyl group, an acyl group or an aryl group, and more preferably an oxygen radical or an alkoxy group.

[0426] The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12. The alkyl group may be linear, branched, or cyclic, but is preferably linear. The alkyl group may have a substituent. Examples of the substituent include those listed above for the substituent T.

[0427] The number of carbon atoms in the alkenyl group is preferably 2 to 20, more preferably 2 to 12. The alkenyl group is preferably linear or branched, more preferably linear. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0428] The number of carbon atoms in the alkoxy group is preferably 1 to 20, more preferably 1 to 12. The alkoxy group is preferably linear or branched, more preferably linear. The alkoxy group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0429] The number of carbon atoms in the acyl group is preferably 2 to 20, more preferably 2 to 14. The acyl group may have a substituent. Examples of the substituent include those listed above for the substituent T.

[0430] The number of carbon atoms in the aryl group is preferably 6 to 20. The aryl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0431] The compound represented by formula (Ao1-1) is preferably a compound represented by formula (Ao1-2).

[0432] [Chemical Formula 68]

[0433]

[0434] In formula (Ao1-2), X a11 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group or an oxygen free radical,

[0435] R a11 represents a substituent;

[0436] X in formula (Ao1-2) a11 The meaning is the same as X in formula (Ao1-1) a1 The meanings and preferred ranges are the same.

[0437] As R in formula (Ao1-2) a11 Examples of the substituents include those listed above for the substituent T. For example, alkyl, alkenyl, alkynyl, aryl, heterocyclic, cyano, hydroxy, nitro, carboxyl, alkoxy, aryloxy, silyloxy, heterocyclic, acyloxy, carbamoyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, amino, acylamino, aminocarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfamoylamino, alkylsulfonylamino, arylsulfonylamino, mercapto, alkylthio, arylthio, heterocyclic thio, sulfamoyl, sulfo, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, acyl, aryloxycarbonyl, alkoxycarbonyl, carbamoyl, arylazo, heterocyclic azo, imide, phosphino, phosphinyl, phosphinyloxy, phosphinylamino, and silyl groups.

[0438] The compound represented by formula (Ao1-1) is preferably a compound represented by formula (Ao1-3).

[0439] [Chemical Formula 69]

[0440]

[0441] In Formula (Ao1-3), X a21 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group, or an oxyl radical,

[0442] L a21 represents a single bond or a divalent linking group,

[0443] L a22 represents an n-valent group,

[0444] n represents an integer of 1 or more.

[0445] X in Formula (Ao1-3) a21 has the same meaning as X a1 in Formula (Ao1-1), and the preferable range is also the same.

[0446] L in Formula (Ao1-3) a21 The divalent linking group represented by L a22 may include -0-, -CO-, -COO-, -OCO-, -NHCO-, -NHCOO-, -CONH-, -OCONH-, -S-, -SO2-, and -OSO2-.

[0447] L in Formula (Ao1-3) a22 represents an n-valent group. In the case where the n-valent group represented by L a22 is a monovalent group (in the case where n is 1), the n-valent group represented by L a22 may include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxy group, an aryloxy group, a siloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an amido group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heterocyclic azo group, an imide group, a phosphino group, an oxypHosphino group, an oxypHosphinyloxy group, an oxypHosphinylamino group, and a silyl group, and the like.

[0448] In the case where the n-valent group represented by L a22In the case where the represented n-valent group is a group having valence of 2 or more (in the case where n is an integer of 2 or more), L a22 The represented n-valent group can be exemplified by a hydrocarbon group; and a group in which two or more hydrocarbon groups are bonded via -O-, -CO-, -COO-, -OCO-, -NH-, -S-, or a group in which two or more of these are combined.

[0449] The hydrocarbon group can be exemplified by an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and is preferably an aliphatic hydrocarbon group. The number of carbon atoms of the aliphatic hydrocarbon group is preferably from 1 to 30, more preferably from 1 to 20, and further preferably from 1 to 15. The aliphatic hydrocarbon group can be any of a straight chain, a branched chain, and a cyclic, but is preferably a straight chain or a branched chain. The aliphatic hydrocarbon group can be any of a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group, but is preferably a saturated aliphatic hydrocarbon group.

[0450] The number of carbon atoms of the aromatic hydrocarbon group is preferably from 6 to 30, more preferably from 6 to 20, and further preferably from 6 to 10.

[0451] The hydrocarbon group can have a substituent. As the substituent, a halogen atom, a hydroxyl group, an alkyl group, an aryl group, and the like can be exemplified.

[0452] In the case where the n-valent group is a group having valence of 2 or more, L a22 The represented n-valent linking group is preferably a group containing a saturated aliphatic hydrocarbon group having from 1 to 20 carbon atoms (preferably from 2 to 15 carbon atoms, and more preferably from 2 to 10 carbon atoms).

[0453] n of formula (Ao1-3) represents an integer of 1 or more, preferably an integer of 2 or more, more preferably an integer of from 2 to 6, and further preferably an integer of from 2 to 4.

[0454] -Regarding the compound represented by formula (Ao2-1)

[0455] R of formula (Ao2-1) p1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or -Si(R p101 )(R p102 )(R p103 ), R p101 ~R p103 each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxyl group, an alkenyloxyl group, or an aryloxyl group.

[0456] R p1 is preferably a hydrogen atom, an alkyl group, or an acyl group, and more preferably an alkyl group or an acyl group.

[0457] As R p2 ~R p6The substituents represented by the above group include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, cyano groups, hydroxyl groups, nitro groups, carboxyl groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy groups, aryloxycarbonyloxy groups, amino groups, acylamino groups, aminocarbonylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfamoylamino groups, alkylsulfonylamino groups, arylsulfonylamino groups, mercapto groups, alkylthio groups, arylthio groups, heterocyclicthio groups, sulfamoyl groups, The acyl group, sulfo group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, arylazo group, heterocyclic azo group, imide group, phosphinyl group, phosphinyloxy group, phosphinylamino group and silyl group are preferably alkyl group, alkenyl group, aryl, alkoxy group, alkoxycarbonyl group, aryloxy group, aryloxycarbonyl group, alkylsulfonyl group and arylsulfonyl group, more preferably alkyl group or alkenyl group, further preferably alkyl group.

[0458] The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, more preferably branched. The alkyl group may have a substituent. Examples of the substituent include those listed above for the substituent T.

[0459] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 5. The alkenyl group is preferably linear or branched, more preferably branched. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0460] R p2 ~R p6 At least one of them is preferably a substituent, and more preferably two or more of them are substituents.

[0461] In formula (Ao2-1), R p1 ~R p6 Two adjacent groups in the group may bond to each other to form a ring. The ring formed is preferably a 5-membered ring or a 6-membered ring. The ring formed may further have a substituent. As the substituent, the groups listed in the substituent T above and the group containing an ethylenically unsaturated bond can be mentioned. As the group containing an ethylenically unsaturated bond, vinyl etc. can be mentioned.

[0462] As a preferred embodiment of formula (Ao2-1), R p1 With R p2The ring is preferably a 5-membered ring or a 6-membered ring. The ring is preferably further substituted. Examples of substituents include aryl groups, heteroaryl groups, and groups containing ethylenically unsaturated bonds. Preferably, they are aryl groups and groups containing ethylenically unsaturated bonds, and more preferably aryl groups. The aryl and heteroaryl groups may further have substituents. Examples of further substituents include alkyl groups, alkenyl groups, aryl groups, alkoxy groups, alkenyloxy groups, aryloxy groups, acyl groups, and hydroxyl groups.

[0463] In formula (Ao2-1), R p1 ~R p6 Not all of them are hydrogen atoms.

[0464] R p1 ~R p6 The total number of carbon atoms is preferably 10 or more, more preferably 16 or more.

[0465] The compound represented by formula (Ao2-1) is preferably a compound represented by formula (Ao2-2).

[0466] [Chemical Formula 70]

[0467]

[0468] In formula (Ao2-2), R p11 ~R p14 each independently represents a hydrogen atom, an alkyl group or an alkenyl group,

[0469] Y p11 represents an aryl group, a heteroaryl group, or a group containing an ethylenically unsaturated bond.

[0470] R p11 ~R p14 The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, more preferably branched. The alkyl group may have a substituent. Examples of the substituent include those listed above for the substituent T.

[0471] R p11 ~R p14 The number of carbon atoms in the alkenyl group represented is preferably 2 to 10, more preferably 2 to 5. The alkenyl group is preferably linear or branched, more preferably branched. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0472] R p11 ~R p14 At least one of them is preferably an alkyl group or an alkenyl group, and more preferably two or more of them are alkyl groups or alkenyl groups. p11 ~R p14At least one of them is preferably an alkyl group, and more preferably two or more of them are alkyl groups.

[0473] Y p11 represents an aryl group, a heteroaryl group or a group containing an ethylenically unsaturated bond, and is preferably an aryl group.

[0474] The aryl and heteroaryl groups may further have substituents. Examples of further substituents include alkyl, alkenyl, aryl, alkoxy, alkenyloxy, aryloxy, acyl, and hydroxyl groups. Examples of the group containing an ethylenically unsaturated bond include vinyl.

[0475] The compound represented by formula (Ao2-1) is preferably a compound represented by formula (Ao2-3).

[0476] [Chemical Formula 71]

[0477]

[0478] In formula (Ao2-3), R p21 ~R p24 each independently represents a hydrogen atom, an alkyl group or an alkenyl group,

[0479] R p25 represents an alkyl group, an alkenyl group or a hydroxyl group,

[0480] L p21 represents an S-valent group,

[0481] r represents an integer from 0 to 4,

[0482] s represents an integer greater than 1,

[0483] When r is an integer greater than or equal to 2, r R p25 It can be the same or different.

[0484] R in formula (Ao2-3) p21 ~R p24 The meaning is the same as R in formula (Ao2-2) p11 ~R p14 The meanings and preferred ranges are the same.

[0485] R p21 ~R p24 At least one of them is preferably an alkyl group or an alkenyl group, and more preferably two or more of them are alkyl groups or alkenyl groups. p21 ~R p24 At least one of them is preferably an alkyl group, and more preferably two or more of them are alkyl groups.

[0486] R in formula (Ao2-3) p25 It is preferably an alkyl group or an alkenyl group, and more preferably an alkyl group.

[0487] The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, more preferably branched. The alkyl group may have a substituent. Examples of the substituent include those listed above for the substituent T.

[0488] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 5. The alkenyl group is preferably linear or branched, more preferably branched. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0489] L p21 Indicates an S-valent group. p21 When the trivalent group represented by is a monovalent group, L p21 Examples of the trivalent group represented by include alkyl, alkenyl, alkoxy and alkynyl groups, and an alkyl or alkoxy group is preferred.

[0490] In L p21 When the trivalent group represented by is a divalent or higher valent group, as L p21 Examples of the s-valent group represented by include hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NHCO-, -NHCOO-, -CONH-, -OCONH-, -S-, -SO2-, -OSO2-, and groups formed by combining two or more of these groups.

[0491] Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be linear, branched, or cyclic, but is preferably linear or branched. The aliphatic hydrocarbon group may be saturated or unsaturated, but is preferably saturated.

[0492] The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.

[0493] The hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a hydroxyl group, an alkyl group, and an aryl group.

[0494] r represents an integer of 0-4, and preferably an integer of 0-2.

[0495] s represents an integer of 1 or greater, preferably an integer of 1 to 4, and more preferably 1 or 2.

[0496] As specific examples of the anti-fading agent, there can be mentioned the compounds described in the Examples described later, the compounds described in paragraphs 0157 to 0171 of Japanese Patent Application Publication No. 2009-067984, and the compounds having the structures shown below.

[0497] [Chemical Formula 72]

[0498]

[0499] The content of the anti-fading agent in the total solid components 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, and more preferably 30% by mass or less, and further preferably 20% by mass or less.

[0500] The content of the anti-fading agent is preferably 0.1 to 500 parts by mass with respect to 100 parts by mass of the ultraviolet absorber. The upper limit is preferably 300 parts by mass or less, and more preferably 200 parts by mass or less. The lower limit is preferably 1 part by mass or more, and more preferably 10 parts by mass or more.

[0501] The content of the anti-fading agent is preferably 0.1 to 500 parts by mass with respect to 100 parts by mass of the specific ultraviolet absorber described above. The upper limit is preferably 300 parts by mass or less, and more preferably 200 parts by mass or less. The lower limit is preferably 1 part by mass or more, and more preferably 10 parts by mass or more.

[0502] The composition of the present application can contain only one anti-fading agent, or can contain two or more. In the case where two or more anti-fading agents are contained, the total amount thereof is preferably within the range described above.

[0503] <<Curable Compound>>

[0504] The composition of the present application contains a curable compound. As the curable compound, there can be mentioned a polymerizable compound, a resin, or the like. The resin can be a non-polymerizable resin (a resin not having a polymerizable group), or a polymerizable resin (a resin having a polymerizable group). As the polymerizable group, there can be mentioned a group containing an ethylenic unsaturated bond, a cyclic ether group, or the like. As the group containing an ethylenic unsaturated bond, there can be mentioned a vinyl group, a vinylphenyl group, a (methyl)allyl group, a (methyl)acryloyl group, a (methyl)acryloyloxy group, a (methyl)acryloylamido group, or the like, and preferably a (methyl)allyl group, a (methyl)acryloyl group, and a (methyl)acryloyloxy group, and more preferably a (methyl)acryloyloxy group. As the cyclic ether group, there can be mentioned an epoxy group, an oxetanyl group, or the like, and preferably an epoxy group.

[0505] The curable compound contained in the composition of the present application preferably contains at least one selected from a resin and a polymerizable compound. In the curable compound, a resin and a polymerizable compound can be used in combination.

[0506] (polymerizable compound)

[0507] As the polymerizable compound, a compound which can be polymerized and cured by imparting energy can be used without any limitation. The polymerizable compound can be a radical polymerizable compound or a cationic polymerizable compound.

[0508] As the polymerizable compound, any one of a monomer, a prepolymer (i.e., a dimer, a trimer or an oligomer) and a mixture of these, and a (co)polymer of a compound selected from a monomer and a prepolymer, etc. can be used, and a monomer is preferred.

[0509] 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.

[0510] -radical polymerizable compound-

[0511] As the radical polymerizable compound, a compound having a group containing an ethylenic unsaturated bond, etc. can be given. As the radical polymerizable compound, an unsaturated carboxylic acid (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), an ester of an unsaturated carboxylic acid and an amide of an unsaturated carboxylic acid, and a (co)polymer of an unsaturated carboxylic acid or an ester or an amide thereof can be given. Among them, an ester of an unsaturated carboxylic acid and an aliphatic polyol and an amide of an unsaturated carboxylic acid and an aliphatic polyamine, and a homopolymer or a copolymer of these are preferred.

[0512] As the radical polymerizable compound, an addition reaction product of an unsaturated carboxylic acid ester or an unsaturated carboxylic acid amide having a nucleophilic substituent (e.g., a hydroxyl group, an amino group, a mercapto group, etc.) and a monofunctional or polyfunctional isocyanate compound or an epoxy compound; a dehydration condensation reaction product of an unsaturated carboxylic acid ester or an unsaturated carboxylic acid amide having a nucleophilic substituent and a monofunctional or polyfunctional carboxylic acid; an addition reaction product of an unsaturated carboxylic acid ester or an unsaturated carboxylic acid amide having an electrophilic substituent (e.g., an isocyanate group, an epoxy group, etc.) and a monofunctional or polyfunctional alcohol, amine or mercaptan; a substitution reaction product of an unsaturated carboxylic acid ester or an unsaturated carboxylic acid amide having a leaving substituent (e.g., a halogen atom, a tosylate oxy group, etc.) and a monofunctional or polyfunctional alcohol, amine or mercaptan; etc. can be used. In addition, a compound obtained by substituting the above unsaturated carboxylic acid with an unsaturated phosphonic acid, styrene or vinyl ether, etc. can also be used.

[0513] Among the radical polymerizable compounds, a plurality of compounds having different functional groups or a plurality of compounds having different types of polymerizable groups (for example, acrylates, methacrylates, styrene compounds, vinyl ether compounds, etc.) may be used in combination.

[0514] Furthermore, the radical polymerizable compound is preferably a (meth)acrylate compound, more preferably a difunctional or higher functional (meth)acrylate compound, further preferably a 2- to 15-functional (meth)acrylate compound, further more preferably a 2- to 10-functional (meth)acrylate compound, and particularly preferably a 2- to 6-functional (meth)acrylate compound.

[0515] 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) modified product, dipentaerythritol hexa(meth)acrylate EO (ethylene oxide) modified product, and benzyl(meth)acrylate.

[0516] Examples of commercially available radical polymerizable compounds include KAYARAD series manufactured by Nippon Kayaku Co., Ltd. (e.g., D-330, D-320, D-310, PET-30, TPA-330, DPHA, etc.), NK Ester series manufactured by Shin-Nakamura Chemical Co., Ltd. (e.g., A-DPH-12E, A-TMMT, A-TMM-3, etc.), LIGHT ACRYLATE series manufactured by KYOEISHA CHEMICAL Co., Ltd. (e.g., DCP-A, etc.), ARONIX series manufactured by TOAGOSEI CO., Ltd. (e.g., M-305, M-306, M-309, M-450, M-402, TO-1382, etc.), and PHOSPHATE series manufactured by Osaka Organic Chemical Industry Co., Ltd. Co., Ltd. Viscoat series (for example, V#802, etc.) multifunctional (meth)acrylate compounds.

[0517] The radical polymerizable compound can use (meth)acrylate compounds described in Japanese Patent Application Publication No. 48-064183, Japanese Patent Application Publication No. 49-043191, Japanese Patent Application Publication No. 52-030490, and compounds introduced as photocurable monomers and oligomers in Journal of the Adhesion Society of Japan, vol. 20, No. 7, pp. 300-308 (1984).

[0518] - Cationic polymerizable compound -

[0519] As the cationic polymerizable compound, a compound having a cationic polymerizable group can be given. As the cationic polymerizable group, a cyclic ether group such as an epoxy group and an oxetanyl group, and an ethylene ether group, etc. can be given, and a cyclic ether group is preferable. Also, the cationic polymerizable compound is preferably a multifunctional cationic polymerizable compound having two or more cationic polymerizable groups.

[0520] As the cationic polymerizable compound, a multifunctional alicyclic epoxy compound, a multifunctional heterocyclic epoxy compound, a multifunctional oxetane compound, an alkylene glycol diglycidyl ether, and an alkylene glycol monovinyl monoglycidyl ether, etc. can be given.

[0521] As specific examples of the cationic polymerizable compound, 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-oxiranylyl)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 compounds described in paragraphs 0029 to 0058 of Japanese Patent Application Publication No. 2012-046577 can be given.

[0522] The cationic polymerizable compound can also use a (meth)acrylate compound having a cationic polymerizable group. As specific examples of the (meth)acrylate compound having a cationic polymerizable group, 3,4-epoxycyclohexylmethyl methacrylate, etc. can be given. As a commercial product, for example, CYCLOMER M100 manufactured by Daicel Corporation, etc. can be given.

[0523] Examples of cationic polymerizable compounds that can be used include ARON OXETANE series (OXT-101, OXT-121, OXT-221, etc.) manufactured by TOAGOSEI CO., Ltd., CELLOXIDE series (2021P) manufactured by Daicel Corporation, and alkyl divinyl ether CHDVE, alkyl monovinyl ether EHVE, hydroxyalkyl vinyl ether CHMVE, and hydroxyalkyl vinyl ether HBVE manufactured by Nippon Carbide Industries Co., Inc. Furthermore, the substances listed as specific examples of epoxy resins described later can also be used.

[0524] (resin)

[0525] Examples of the resin include (meth)acrylic resins, ene-thiol resins, polyester resins, polycarbonate resins, vinyl polymers [e.g., polydiene resins, polyolefin resins, polystyrene resins, polyvinyl ether resins, polyvinyl alcohol resins, polyvinyl ketone resins, polyvinyl fluoride resins, and polyvinyl bromide resins], polysulfide ether resins, polyphenylene resins, polyurethane resins, polysulfonate resins, nitrosopolymer resins, polysiloxane resins, polysulfide resins, polythioester resins, polysulfone resins, polysulfoneamide resins, polyamide resins, polyimine resins, polyurea resins, polyphosphazene resins, polysilane resins, polysilazane resins, and polyfuran resins. resin, polybenzoxazole resin, polyoxadiazole resin, polybenzothiazine phenothiazine resin, polybenzothiazole resin, polypyrazinoquinoxaline resin, polyquinoxaline resin, polybenzimidazole resin, polyoxyisoindoline resin, polydioxyisoindoline resin, polytriazine resin, polypyridazine resin, polypiperazine resin, polypyridine resin, polypiperidine resin, polytriazole resin, polypyrazole resin, polypyrrolidine resin, polycarborane resin, polyoxybicyclononane resin, polydibenzofuran resin, polyphthalolactone resin, polyacetal resin, polyimide resin, polyamideimide resin, olefin resin, cycloolefin resin, epoxy resin, cellulose acylate resin, etc.

[0526] Examples of (meth)acrylic resins include polymers containing structural units derived from (meth)acrylic acid and / or its esters. Specifically, examples include polymers obtained by polymerizing at least one compound selected from the group consisting of (meth)acrylic acid, (meth)acrylate esters, (meth)acrylamide, and (meth)acrylonitrile.

[0527] As the polyester resin, a polymer obtained by the reaction of a polyhydric alcohol (e.g., ethylene glycol, propylene glycol, glycerol, and trimethylolpropane) and a polybasic acid (e.g., an aromatic dicarboxylic acid (examples: terephthalic acid, isophthalic acid, and naphthalene dicarboxylic acid, and a dicarboxylic acid in which the hydrogen atoms of the aromatic ring are substituted with a methyl group, an ethyl group, or a phenyl group, etc.), an aliphatic dicarboxylic acid (examples: adipic acid, sebacic acid, and dodecanedicarboxylic acid) having 2 to 20 carbon atoms, or an alicyclic dicarboxylic acid (examples: cyclohexane dicarboxylic acid, etc.), etc.) or a polymer obtained by the ring-opening polymerization of a cyclic ester compound such as a caprolactone monomer (e.g., polycaprolactone) can be given. As specific examples of the polyester resin, polyethylene terephthalate and polyethylene naphthalate, etc. can be given.

[0528] As the epoxy resin, a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, an aliphatic epoxy resin, etc. can be given. The epoxy resin can use a commercially available product on the market, and as examples of the commercially available product, the following resins can be given.

[0529] As examples of commercially available products of bisphenol A type epoxy resins, jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (all manufactured by Mitsubishi Chemical Corporation), and EPICLON 860, EPICLON 1050, EPICLON 1051, and EPICLON 1055 (all manufactured by DIC Corporation), and the like can be given. As examples of commercially available products of bisphenol F type epoxy resins, jER806, jER807, jER4004, jER4005, jER4007, and jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON 830 and EPICLON 835 (all manufactured by DIC Corporation), and LCE-21 and RE-602S (all manufactured by Nippon Kayaku Co., Ltd.), and the like can be given. As examples of commercially available products of phenol novolak type epoxy resins, jER152, jER154, jER157S70, and jER157S65 (all manufactured by Mitsubishi Chemical Corporation), and EPICLON N-740, EPICLON N-770, and EPICLON N-775 (all manufactured by DIC Corporation), and the like can be given. As examples of commercially available products of cresol novolak type epoxy resins, 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.), and the like can be given.Examples of commercially available aliphatic epoxy resins include ADEKARESIN EP series (e.g., EP-4080S, EP-4085S, and EP-4088S; manufactured by ADEKA CORPORATION), Celoxide 2021P, Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE 3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (all manufactured by Daicel Corporation), Denacol EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (all manufactured by Nagase ChemteX Corporation), ADEKARESIN EP series (e.g., EP-4000S, EP-4003S, EP-4010S, and EP-4011S; manufactured by ADEKA

[0014] Examples of commercially available epoxy resins include JEWEL-1000, JEWEL-1001, JEWEL-1002 (all manufactured by ADEKA CORPORATION), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, and EPPN-502 (all manufactured by ADEKA CORPORATION), and JEWEL-1031S (manufactured by Mitsubishi Chemical Corporation). Examples of 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 (all manufactured by NOF CORPORATION, epoxy group-containing polymers).

[0530] As the cellulose acylate resin, the cellulose acylate described in paragraphs 0016 to 0021 of Japanese Patent Application Laid-Open No. 2012-215689 can be suitably used. As the polyester resin, commercially available products such as the Byron series (e.g., Byron 500) manufactured by Toyobo Co., Ltd. can also be used. As commercially available (meth)acrylic resins, the SK Dyne series (e.g., SK Dyne-SF2147) manufactured by Soken Chemical & Engineering Co., Ltd. can also be used.

[0531] The polystyrene resin preferably contains 50% by mass or more of repeating units derived from a styrene-based monomer, more preferably 70% by mass or more of repeating units derived from a styrene-based monomer, and still more preferably 85% by mass or more of repeating units derived from a styrene-based monomer.

[0532] Specific examples of styrene-based monomers include styrene and its derivatives. Styrene derivatives are compounds in which other groups are bonded to styrene, and examples include alkyl styrenes such as o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, o-ethylstyrene, and p-ethylstyrene; and substituted styrenes such as hydroxystyrene, tert-butoxystyrene, vinylbenzoic acid, o-chlorostyrene, and p-chlorostyrene, in which a hydroxyl group, alkoxy group, carboxyl group, halogen group, or the like is introduced into the benzene nucleus of styrene.

[0533] Furthermore, 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; anhydrides (unsaturated dicarboxylic acid anhydride monomers) such as maleic anhydride, itaconic acid, ethylmaleic acid, methylitaconic 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.

[0534] As commercially available products of the polystyrene resin, AS-70 (acrylonitrile-styrene copolymer resin) manufactured by NIPPON STEEL Chemical & Material Co., Ltd., SMA2000P (styrene-maleic acid copolymer) of KAWAHARA PETROCHEMICAL CO., LTD., CLEAREN 530L, CLEAREN 730L manufactured by Denka Company Limited., TUFPRENE 126S, ASAPRENE T411 manufactured by Asahi Kasei Corporation, KRATON D1102A, KRATON D1116A manufactured by KRATON POLYMERS JAPAN Ltd., Styrolux S, Styrolux T manufactured by STYROLUTION, Asaflex 840, Asaflex 860 manufactured by Asahi Kasei Corporation, 679, HF77, SGP-10, 475D, H0103, HT478 manufactured by PS Japan Corporation, Dick Styrene XC-515, Dick Styrene XC-535, Dick Styrene GH-8300-5 manufactured by DIC Corporation, and the like can be given. Also, as commercially available products of the hydrogenated polystyrene resin, Tuftec H series manufactured by Asahi Kasei Corporation, KRATON G series manufactured by Shell Japan Limited, DYNARON (hydrogenated styrene-butadiene random copolymer) manufactured by JSR Corporation, SEPTON manufactured by Kuraray Co., Ltd., and the like can be given. Also, as commercially available products of the modified polystyrene resin, Tuftec M series manufactured by Asahi Kasei Corporation, Epofriend manufactured by Daicel Corporation, polar group-modified DYNARON manufactured by JSR Corporation, RESEDA manufactured by TOAGOSEI CO., Ltd., and the like can be given.

[0535] Examples of cycloolefin resins include (R1) polymers containing structural units derived from norbornene compounds, (R2) polymers containing structural units derived from monocyclic cycloolefin 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 products of polymers containing structural units derived from each of (R1) to (R4). In this specification, polymers containing structural units derived from norbornene compounds and polymers containing structural units derived from monocyclic cycloolefin compounds include ring-opening polymers of these compounds.

[0536] The cycloolefin 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 a structural unit represented by formula (A-II) is an addition polymer of a norbornene compound, while the polymer having a structural unit represented by formula (A-III) is a ring-opening polymer of a norbornene compound.

[0537] [Chemical Formula 73]

[0538]

[0539] In formula (A-II) and formula (A-III), m is an integer of 0 to 4, and preferably 0 or 1.

[0540] 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.

[0541] As R 3 ~R 6 Examples of the hydrocarbon group include alkyl, alkenyl, alkynyl and aryl groups, and are preferably alkyl or aryl groups.

[0542] X 2 and X 3 、Y 2 and Y 3 Each independently represents 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 CONR13 R 14 、-(CH2) n NR 13 R 14 、-(CH2) n OZ 1 、-(CH2) n W 1 or X 2 With Y 2 or X 3 With Y 3 (-CO)2O or (-CO)2NR formed by mutual bonding 15 .

[0543] Here, it can be used as X 2 、X 3 、Y 2 and Y 3 R in the above groups 11 ~R 15 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and Z 1 represents a hydrocarbon group or a hydrocarbon group substituted by a halogen, W 1 Represents 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 is a hydrocarbon group having 1 to 10 carbon atoms. p is an integer of 0 to 3. n is an integer of 0 to 10, preferably 0 to 8, more preferably 0 to 6.

[0544] R in formula (A-II) and formula (A-III) 3 ~R 6 Each independently is preferably a hydrogen atom or -CH 3 , and from the viewpoint of moisture permeability, a hydrogen atom is more preferred.

[0545] X 2 and X 3 A hydrogen atom, -CH 3 , and -C 2 H 5 are respectively preferred, and a hydrogen atom is more preferred from the viewpoint of moisture permeability.

[0546] Y 2 and Y 3 Preferably, each independently is a hydrogen atom, a halogen atom (especially a chlorine atom) or -(CH2) n COOR 11 (especially-COOCH a ), and from the viewpoint of moisture permeability, a hydrogen atom is further preferred.

[0547] Other groups can be selected appropriately.

[0548] 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).

[0549] [Chemical Formula 74]

[0550]

[0551] In formula (AI), R 1 and R 2 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and X 1 and Y 1 Each independently represents 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 With Y 2 or X 3 With Y 3 (-CO)2O or (-CO)2NR formed by mutual bonding 15 . Can be used as X 1 and Y 1 R in the above groups 11 ~R 15 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and Z 1 represents a hydrocarbon group or a hydrocarbon group substituted by a halogen, W 1 Represents 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 is a hydrocarbon group having 1 to 10 carbon atoms. p is an integer of 0 to 3. n is an integer of 0 to 10.

[0552] The content of the structural unit represented by formula (A-II) or formula (A-III) in the cyclic polyolefin resin is preferably 90% by mass or less, more preferably 30 to 85% by mass, further preferably 50 to 79% by mass, and even more preferably 60 to 75% by mass.

[0553] Cycloolefin resins are described in Japanese Patent Application Laid-Open No. 10-007732, Japanese National Publication No. 2002-504184, International Publication No. 2004 / 070463, and the like, and these contents can be appropriately referred to.

[0554] The cycloolefin resin can be obtained by subjecting norbornene compounds (eg, polycyclic unsaturated norbornene compounds) to addition polymerization.

[0555] Examples of commercially available cycloolefin resins include the ARTON series manufactured by JSR Corporation (for example, ARTON G, F, and RX4500), and ZEONOR ZF14, ZF16, and ZEONEX 250 and 280 manufactured by Zeon Corporation.

[0556] Examples of cycloolefin resins include copolymers obtained by addition copolymerization of norbornene compounds with olefins such as ethylene, propylene, and butene, butadiene, conjugated dienes such as isoprene, non-conjugated dienes such as ethylene norbornene, acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, acrylic esters, methacrylic esters, maleimide, vinyl acetate, or vinyl chloride. Among these, copolymers with ethylene are preferred. Addition (co)polymers of such norbornene compounds are commercially available from Mitsui Chemicals, Inc. under the trade name APEL, and have varying glass transition temperatures (Tg). Examples include APL8008T (Tg 70°C), APL6011T (Tg 105°C), APL6013T (Tg 125°C), and APL6015T (Tg 145°C). Furthermore, particles such as TOPAS8007, TOPAS6013, and TOPAS6015 are commercially available from Polyplastics Co., Ltd. Furthermore, Appear3000 is commercially available from Ferrania.

[0557] Furthermore, hydrogenated cycloolefin resins can be synthesized by subjecting a norbornene compound, etc. to addition polymerization or ring-opening polymerization, followed by hydrogenation. Synthesis methods are described, for example, in Japanese Patent Application Laid-Open No. 01-240517, Japanese Patent Application Laid-Open No. 07-196736, Japanese Patent Application Laid-Open No. 60-026024, Japanese Patent Application Laid-Open No. 62-019801, Japanese Patent Application Laid-Open No. 2003-159767, and Japanese Patent Application Laid-Open No. 2004-309979.

[0558] The weight molecular weight of the cycloolefin resin is preferably 5,000 to 500,000, more preferably 8,000 to 200,000, and even more preferably 10,000 to 100,000.

[0559] Examples of the polycarbonate resin include reaction products of a polyphenol compound and phosgene or a carbonate compound.

[0560] Examples of the polyphenol compound 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(3-isopropyl)-1-phenylphenol. propyl-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, 4,4'-dihydroxydiphenyl ether, and preferably hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, and bisphenol A.

[0561] Examples of the carbonate compound include phosgene, diphenyl carbonate, bis(chlorophenyl) carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, dimethyl carbonate, diethyl carbonate, and dibutyl carbonate. Preferred are bis(diphenyl) carbonate, dimethyl carbonate, and diethyl carbonate.

[0562] Examples of commercially available polycarbonate resins include PANLITE L-1250WP and PANLITE SP-1516 manufactured by TEIJIN LIMITED, IUPZETA EP-5000 and IUPZETA EP-4000 manufactured by MITSUBISHI GAS CHEMICAL COMPANY, INC., and Calibur 301-30 manufactured by Sumika Polycarbonate Ltd.

[0563] Examples of the thiourethane resin include reaction products of an isocyanate compound and a polythiol compound, reaction products of a thiourethane resin precursor, etc. Commercially available thiourethane resin precursors include MR-7, MR-8, MR-10, and MR-174 manufactured by Mitsui Chemicals, Inc.

[0564] 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 those polymerized by dehydration condensation of a diamine and a dicarboxylic acid, wherein at least one of the diamine and the dicarboxylic acid contains an aromatic ring. Specific examples of aromatic polyamide resins include condensation products of m-xylylenediamine and adipic acid or adipic acid halide.

[0565] The resin may also have an acid group. Examples of the acid group include a carboxyl group, a phosphate group, a sulfonate group, and a phenolic hydroxyl group. The acid group may be a single type or may be two or more types. A resin having an acid group can be used as an alkali-soluble resin and can also be used as a dispersant.

[0566] As resins having an acid group, reference can be made to paragraphs 0558 to 0571 of Japanese Patent Application Publication No. 2012-208494 (paragraphs 0685 to 0700 of the corresponding U.S. Patent Application Publication No. 2012 / 0235099) and paragraphs 0076 to 0099 of Japanese Patent Application Publication No. 2012-198408, the contents of which are incorporated herein. Furthermore, as a resin having an acid group, ACRYBASE FF-426 (manufactured by NIPPON SHOKUBAI CO., LTD.) can also be used.

[0567] 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 higher, more preferably 70 mgKOH / g or higher. The upper limit of the acid value is preferably 150 mgKOH / g or lower, more preferably 120 mgKOH / g or lower. The acid value of the resin is measured in accordance with JIS K0070 (1992) and calculated as 1 mmol / g = 56.1 mgKOH / g.

[0568] The resin may have a polymerizable group. Examples of the polymerizable group include groups containing ethylenically unsaturated bonds and cyclic ether groups. Examples of the group containing ethylenically unsaturated bonds include vinyl, styryl, allyl, methallyl, and (meth)acryloyl groups. Examples of the cyclic ether group include epoxy and oxetane groups.

[0569] Commercially available products of polymerizable group-containing resins 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 (COOH-containing urethane acrylic oligomer; Diamond Shamrock Co., Ltd.), Viscoat R-264 and KS Resist 106 (both manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY Ltd.), CYCLOMER P series (such as ACA230AA), PLACCEL CF200 series (all manufactured by Daicel Corporation), Ebecryl 3800 (manufactured by Daicel UCB Co., Ltd.), and Acrycure-RD-F8 (manufactured by Nippon Shokubai Co., Ltd.). Commercially available products such as those described above for the epoxy resins may also be mentioned.

[0570] 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.

[0571] Resin can also use pressure-sensitive adhesives and adhesives. As pressure-sensitive adhesives, for example, acrylic pressure-sensitive adhesives, rubber pressure-sensitive adhesives, silicone pressure-sensitive adhesives, etc. can be mentioned. Acrylic pressure-sensitive adhesives refer to pressure-sensitive adhesives containing polymers of (meth) acrylic acid monomers ((meth) acrylic polymers). As adhesives, for example, polyurethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives and silicone adhesives can be mentioned. Among them, from the viewpoint of high bonding strength, as adhesives, polyurethane resin adhesives or silicone adhesives are preferred. Commercially available adhesives can be used. Examples of commercially available adhesives include a polyurethane resin adhesive (LIS-073-50U: trade name) from TOYO INK CO., Ltd. and an acrylic pressure-sensitive adhesive (SK Dyne-SF2147: trade name) from Soken Chemical & Engineering Co., Ltd.

[0572] The resin is preferably at least one selected from the group consisting of (meth)acrylic resins, polystyrene resins, polyester resins, polyurethane resins, thiourethane resins, polyimide resins, polyamide resins, epoxy resins, polycarbonate resins, phthalate resins, cellulose acylate resins, and cycloolefin resins. From the perspectives of good compatibility with specific compounds and ease of obtaining a cured product with suppressed surface morphology unevenness, the resin is more preferably at least one selected from the group consisting of (meth)acrylic resins, polystyrene resins, polyester resins, polyurethane resins, and cycloolefin resins.

[0573] 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 further 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 further 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, and 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.

[0574] The weight average molecular weight (Mw) is a value determined by gel permeation chromatography (GPC). In the GPC-based determination, as the determination apparatus, HLC (registered trademark) -8020 GPC (manufactured by TOSOH CORPORATION) was used, as the column, 3 pieces of TSKgel (registered trademark) Super Multipore HZ-H (4.6 mm ID x 15 cm, manufactured by TOSOH CORPORATION) were used, and as the eluent, THF (tetrahydrofuran) was used. Also, as the determination conditions, the sample concentration was set to 0.45 mass%, the flow rate was set to 0.35 ml / min, the sample injection amount was set to 10 μl, and the determination temperature was set to 40°C, and the determination was performed using an RI detector. The calibration curve was prepared from eight samples of "Standard Sample TSK Standard, Polystyrene": "F-40", "F-20", "F-4", "F-1", "A-5000", "A-2500", "A-1000", and "n-Propylbenzene" of Tosoh Corporation.

[0575] The total light transmittance of the resin is preferably 80% or more, more preferably 85% or more, and further preferably 90% or more. In the present specification, the total light transmittance of the resin is a value determined in accordance with the contents described in "4th Edition Experimental Chemistry Lecture 29 High Molecular Material Medium" (Maruzen, 1992) pp. 225-232 edited by the Chemical Society of Japan.

[0576] The content of the curable compound in the total solid content of the composition is preferably 1 to 99.9 mass%. The lower limit is preferably 30 mass% or more, more preferably 50 mass% or more, and further preferably 70 mass% or more. The upper limit is preferably 95 mass% or less, more preferably 90 mass% or less, and further preferably 80 mass% or less. The composition can contain only one curable compound, or can contain two or more. In the case where two or more curable compounds are contained, the total amount of them is preferably within the above range.

[0577] In the case where the curable compound contained in the composition of the present application contains a resin, the content of the resin in the total solid content of the composition is preferably 1 to 99.9 mass%. The lower limit is preferably 30 mass% or more, more preferably 50 mass% or more, and further preferably 70 mass% or more. The upper limit is preferably 95 mass% or less, more preferably 90 mass% or less, and further preferably 80 mass% or less. The composition can contain only one resin, or can contain two or more. In the case where two or more resins are contained, the total amount of them is preferably within the above range.

[0578] In the case where the curable compound contained in the composition of the present application contains a polymerizable compound, the content of the polymerizable compound in the total solid content of the composition is preferably from 0.1 to 90% by mass. The lower limit is preferably 1% by mass or more, more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 70% by mass or less. The composition of the present application can contain only one polymerizable compound, or two or more polymerizable compounds. In the case where two or more polymerizable compounds are contained, the total amount thereof is preferably within the above range.

[0579] <<Polymerization initiator>>

[0580] The composition of the present application can contain a polymerization initiator. The polymerization initiator can use a compound which can generate an initiation species required for the polymerization reaction by imparting energy. As the polymerization initiator, a radical polymerization initiator and a cationic polymerization initiator can be given. In the case where a radical polymerizable compound is used as the polymerizable compound, the polymerization initiator is preferably a radical polymerization initiator. In the case where a cationic polymerizable compound is used as the polymerizable compound, the polymerization initiator is preferably a cationic polymerization initiator.

[0581] As the polymerization initiator, for example, a photopolymerization initiator and a thermal polymerization initiator can be appropriately selected, and a photopolymerization initiator is preferred. The photopolymerization initiator is a compound which is photosensitive by exposure to light, and initiates or promotes the polymerization of the polymerizable compound. The photopolymerization initiator can be a photoradical polymerization initiator and a photocationic polymerization initiator, and a photoradical polymerization initiator is preferred. The photoradical polymerization initiator is preferably a compound which generates a radical in response to actinic rays having a wavelength of 300 nm or more.

[0582] (photoradical polymerization initiator)

[0583] As the photoradical polymerization initiator, an oxime compound, a halogenated hydrocarbon derivative (for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, and the like), a hydroxydiazole compound, a carbonyl compound, a ketal compound, a benzoin compound, an acridine compound, an organic peroxide, an azo compound, a coumarin compound, an azide compound, a metallocene compound, a hexaarylbiimidazole compound, an organic boronic acid compound, a disulfonic acid compound, an onium salt compound, a phenylethanone compound, an acylphosphine compound, and a diphenyl ketone compound, and the like can be given.

[0584] Examples of the acetophenone compound include aminoacetophenone compounds and hydroxyacetophenone compounds. Examples of the acetophenone compound include the acetophenone compounds described in Japanese Patent Application Laid-Open No. 2009-191179 and Japanese Patent Application Laid-Open No. 10-291969. Examples of commercially available aminoacetophenone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins BV). Examples of commercially available hydroxyacetophenone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins BV).

[0585] Examples of the acylphosphine compound include those described in Japanese Patent No. 4225898. Examples of commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (both manufactured by IGM Resins B.V.).

[0586] 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, 4-dimethylaminoacetophenone, etc., preferably 4,4'-bis(diethylamino)benzophenone from the viewpoint of sensitivity and light resistance of the obtained cured product.

[0587] Examples of oxime compounds include compounds described in Japanese Patent Application Laid-Open No. 2001-233842, compounds described in Japanese Patent Application Laid-Open No. 2000-080068, compounds described in Japanese Patent Application Laid-Open No. 2006-342166, and compounds described in paragraphs 0073 to 0075 of Japanese Patent Application Laid-Open No. 2016-006475. 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).

[0588] As the halogenated hydrocarbon derivative, there can be mentioned the compounds described in Yajima et al., Bull. Chem. Soc. Japan 42, 2924 (1969), U.S. Patent No. 3905815, Japanese Patent Publication No. 46-004605, Japanese Patent Laid-Open No. 48-036281, Japanese Patent Laid-Open No. 55-032070, Japanese Patent Laid-Open No. 60-239736, Japanese Patent Laid-Open No. 61-169835, Japanese Patent Laid-Open No. 61-169837, Japanese Patent Laid-Open No. 62-058241, Japanese Patent Laid-Open No. 62-212401, Japanese Patent Laid-Open No. 63-070243, Japanese Patent Laid-Open No. 63-298339, M. P. Hutt, Journal of Heterocyclic Chemistry 1 (No 3), (1970), and the like, and an oxazole compound or a triazine compound substituted with a trihalomethyl group is preferable.

[0589] As the hexaarylbiimidazole compound, there can be mentioned the compounds described in Japanese Patent Publication No. 06-029285, U.S. Patent No. 3479185, U.S. Patent No. 4311783, U.S. Patent No. 4622286. Specifically, there can be mentioned 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, 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.

[0590] (Photocationic polymerization initiator)

[0591] As the photocationic polymerization initiator, there is no particular limitation as long as it is a compound which generates a protonic acid or a Lewis acid upon irradiation of light. The photoacid generator is preferably a compound which generates an acid upon irradiation of actinic rays having a wavelength of 300 nm or more, preferably a wavelength of 300 to 450 nm. The photoacid generator is preferably a compound which generates an acid having a pKa of 4 or less upon irradiation of light, more preferably a compound which generates an acid having a pKa of 3 or less, and further preferably a compound which generates an acid having a pKa of 2 or less.

[0592] Examples of the photocationic polymerization initiator include oxime sulfonate compounds, triazine compounds, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, sulfone compounds, sulfonate compounds, iminosulfonate compounds, carboxylate compounds, and sulfonimide compounds.

[0593] Specific examples of photocationic polymerization initiators include compounds described in paragraphs 0061 to 0108 of JP-A-2012-046577, paragraphs 0029 to 0030 of JP-A-2002-122994, compounds described in paragraphs 0037 to 0063 of JP-A-2002-122994, and oxime sulfonate compounds described in paragraphs 0081 to 0108 of JP-A-2013-210616. Commercially available photocationic polymerization initiators include WPAG-469 (manufactured by FUJIFILM Wako Pure Chemical Corporation), CPI-100P (manufactured by San-Apro Ltd.), CPI-210S (manufactured by San-Apro Ltd.), and Irgacure 290 (manufactured by BASF Japan Ltd.).

[0594] (Thermal polymerization initiator)

[0595] The thermal polymerization initiator is not particularly limited, and a known thermal polymerization initiator can be used. For example, azo compounds such as 2,2'-azobis(isobutyric acid)dimethyl, 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 can be mentioned.

[0596] Organic peroxides such as 1,1-di(tert-hexylperoxy)cyclohexane, 1,1-di(tert-butylperoxy)cyclohexane, 2,2-di(4,4-di-(tert-butylperoxy)cyclohexyl)propane, tert-hexylperoxyisopropyl monocarbonate, tert-butylperoxy-3,5,5-trimethylhexanoate, tert-butylperoxylaurate, dicumyl peroxide, di(tert-butyl)peroxide, tert-butylperoxy-2-ethylhexanoate, tert-hexylperoxy-2-ethylhexanoate, cumene hydroperoxide, and tert-butyl hydroperoxide;

[0597] Inorganic peroxides such as potassium persulfate, ammonium persulfate, and hydrogen peroxide;

[0598] wait.

[0599] 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, more preferably 0.4% by mass or more. The upper limit is preferably 15% by mass or less, more preferably 10% by mass or less. The composition of the present invention may contain only one polymerization initiator or may contain two or more. When containing two or more polymerization initiators, their total amount is preferably within the above range.

[0600] Catalyst

[0601] 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 relative to 100 parts by mass of the resin. The composition of the present invention may contain only one catalyst or two or more. When containing two or more catalysts, their total amount is preferably within the above range.

[0602] <<Silane Coupling Agent>>

[0603] The composition of the present invention can contain a silane coupling agent. According to this embodiment, the adhesion of the obtained film to the support can be further improved. In the present invention, a silane coupling agent refers to a silane compound having a hydrolyzable group and a functional group other than the hydrolyzable group. Furthermore, a hydrolyzable group refers to a substituent that directly bonds to a silicon atom and can generate a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of hydrolyzable groups include halogen atoms, alkoxy groups, acyloxy groups, and the like, preferably alkoxy groups. That is, the silane coupling agent preferably has an alkoxysilyl compound. Furthermore, examples of functional groups other than the hydrolyzable group include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, urea groups, thioether groups, isocyanate groups, phenyl groups, and the like, preferably amino groups, (meth)acryloyl groups, and epoxy groups. Specific examples of silane coupling agents include compounds described in paragraphs 0018 to 0036 of Japanese Patent Application Publication No. 2009-288703 and compounds described in paragraphs 0056 to 0066 of Japanese Patent Application Publication No. 2009-242604, and these contents are incorporated into this specification. Commercially available silane coupling agents include A-50 (organosilane) from Soken Chemical & Engineering Co., Ltd. The content of the silane coupling agent in the total solid content of the composition of the present invention is preferably 0.1 to 5% by mass. The upper limit is preferably 3% by mass or less, more preferably 2% by mass or less. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. The silane coupling agent may be only one or more. In the case of two or more, the total amount is preferably within the above range.

[0604] <<Surfactants>>

[0605] 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 Japanese Patent Application Laid-Open No. 2009-237362.

[0606] As the surfactant, a nonionic surfactant, a fluorine-based surfactant, or a silicone-based surfactant is preferable.

[0607] As commercially available products of the fluorine-based surfactant, 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, F-560, 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 (manufactured by DIC Corporation), FLUORAD FC430, FC431, FC171 (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 (manufactured by AGC Inc.), PolyFox PF636, PF656, PF6320, PF6520, PF7002 (manufactured by OMNOVA Solutions Inc.), Footgent 710FM, 610FM, 601AD, 601ADH2, 602A, 215M, 245F, 251, 212M, 250, 209F, 222F, 208G, 710LA, 710FS, 730LM, 650AC, 681 (manufactured by NEOS COMPANY LIMITED), and the like can be given.

[0608] The fluorine-based surfactant can also preferably use an acrylic compound having a molecular structure having a functional group containing a fluorine atom, and the functional group portion of the fluorine atom is cut off and the fluorine atom is volatilized upon heating. As such a fluorine-based surfactant, MEGAFAC DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), NIKKEI BUSINESS DAILY (February 23, 2016)) can be given, for example, MEGAFAC DS-21.

[0609] The fluorine-based surfactant can also preferably use a polymer of an ethylene ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic ethylene ether compound.

[0610] A fluorine-based surfactant can also use a block polymer.

[0611] Among the fluorine-based surfactants, a fluorine-containing high molecular 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 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy, propyleneoxy) can also be used.

[0612] A fluorine-based surfactant can also use a fluorine-containing polymer having a group containing an olefinic unsaturated bond in a side chain. As a commercial product, MEGAFAC RS-101, RS-102, RS-718K, RS-72-K (all manufactured by DIC Corporation), and the like can be given.

[0613] Also, since there is a concern about the environmental suitability of a compound having a linear perfluoroalkyl group having 7 or more carbon atoms, as a fluorine-based surfactant, it is preferable to use a fluorine-based surfactant of a replacement material of perfluorooctanoic acid (PFOA) or perfluorooctanesulfonic acid (PFOS).

[0614] As the silicone-based surfactant, a straight-chain polymer formed of a siloxane bond and a modified siloxane polymer into which an organic group is introduced in a side chain or a terminal can be given. As the commercially available product of the silicone-based surfactant, DOWSIL 8032 ADDITIVE, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (all of which are manufactured by Dow Corning Toray Co., Ltd.), X-22-4952, X-22-4272, X-22-6266, KF-351A, K354L, KF-355A, KF-945, KF-640, KF-642, KF-643, X-22-6191, X-22-4515, KF-6004, KP-341, KF-6001, KF-6002 (all of which are manufactured by Shin-Etsu Chemical Co., Ltd.), F-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all of which are manufactured by Momentive Performance Materials Inc.), BYK307, BYK323, BYK330 (all of which are manufactured by BYK Chemie) and the like can be given.

[0615] As the nonionic surfactant, glycerin, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (e.g., glycerin propoxylate, glycerin ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, etc. can be given. As the commercially available nonionic surfactant, PLURONIC L10, L31, L61, L62, 10R5, 17R2, 25R2 (all manufactured by BASF Corporation), TETRONIC 304, 701, 704, 901, 904, 150R1 (all manufactured by BASF Corporation), SOLSPERSE 20000 (all manufactured by Lubrizol Japan Ltd.), NCW-101, NCW-1001, NCW-1002 (all manufactured by FUJIFILM Wako Pure Chemical Corporation), PIONIN D-6112, D-6112-W, D-6315 (all manufactured by TAKEMOTO OIL & FAT CO., Ltd.), OLFIN E1010, Surfynol 104, 400, 440 (all manufactured by Nissin Chemical Industry Co., Ltd.), etc. can be given.

[0616] The content of the surfactant in the total solid component of the composition of the present application is preferably 0.01 to 3.0% by mass, more preferably 0.05 to 1.0% by mass, and further preferably 0.10 to 0.80% by mass. The surfactant can be only one kind, or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.

[0617] <<Solvent>>

[0618] The composition of the present application preferably further contains a solvent. As the solvent, there is no particular limitation, and water and organic solvents can be given. The solvent is preferably an organic solvent.

[0619] As the organic solvent, alcohol-based solvents, ester-based solvents, ether-based solvents, ketone-based solvents, amide-based solvents, hydrocarbon-based solvents, halogen-based solvents, etc. can be given.

[0620] As specific examples of the alcohol-based solvent, 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, glycerin, etc. can be given.

[0621] Specific examples of the ester solvent 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, alkyl alkoxyacetates (e.g., methyl alkoxyacetate, ethyl alkoxyacetate, butyl alkoxyacetate (specifically, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate), Esters, etc.)), alkyl 3-oxypropionates, alkyl 2-oxypropionates, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutyrate, ethyl 2-oxobutyrate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethylene carbonate, etc.

[0622] Specific examples of ether 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.

[0623] Specific examples of the amide solvent include N-methylpyrrolidone, dimethylformamide, and dimethylacetamide.

[0624] Specific examples of the ketone solvent include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, and 3-heptanone.

[0625] Specific examples of the hydrocarbon solvent include toluene and xylene.

[0626] Specific examples of the halogen-based solvent include chloroform and dichloromethane.

[0627] These organic solvents may be used in combination of two or more.

[0628] The organic solvent is preferably a solvent containing at least one selected from the group consisting of methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclopentanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate.

[0629] The content of the solvent in the composition of the present invention is preferably 10 to 90 mass %, more preferably 30 to 90 mass %, and further preferably 50 to 90 mass %. The composition of the present invention may contain only one solvent or two or more. When containing two or more solvents, their total amount is preferably within the above range.

[0630] Furthermore, 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.

[0631] <<Plasticizer>>

[0632] 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 plasticizers, phosphate plasticizers, trimellitate plasticizers, fatty acid ester plasticizers, polyester plasticizers, glycerin plasticizers, and polyalkylene glycol plasticizers, with phthalate plasticizers and phosphate plasticizers being preferred.

[0633] 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 heneicosyl phthalate.

[0634] Examples of the phosphate-based plasticizer include trimethyl phosphate, triethyl phosphate, tributyl phosphate, triphenyl phosphate, and tricresyl phosphate.

[0635] Examples of trimellitate-based plasticizers include tributyl trimetalate and tri(2-ethylhexyl) trimetalate.

[0636] Examples of the fatty acid ester plasticizer include dimethyl adipate, diethyl adipate, dipropyl adipate, diisopropyl adipate, dibutyl adipate, diisobutyl adipate, dimethyl dodecanoate, dibutyl maleate, and ethyl oleate.

[0637] Examples of polyester plasticizers include polyesters formed from an acid component such as adipic acid, sebacic acid, terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic 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, or polyesters formed from hydroxycarboxylic acids such as polycaprolactone. These polyesters may be end-capped with a monofunctional carboxylic acid or a monofunctional alcohol, or may be end-capped with an epoxy compound or the like.

[0638] Examples of the glycerin-based plasticizer include glyceryl monoacetyl monolaurate, glyceryl diacetyl monolaurate, glyceryl monoacetyl monostearate, glyceryl diacetyl monooleate, and glyceryl monoacetyl monomontanate.

[0639] Examples of polyalkylene glycol plasticizers include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide addition polymers of bisphenols, propylene oxide addition polymers of bisphenols, tetrahydrofuran addition polymers of bisphenols, and the like, or terminal epoxy-modified compounds, terminal ester-modified compounds, and terminal ether-modified compounds thereof.

[0640] 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.

[0641] 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, more preferably 0.01% by mass or more. The upper limit is preferably 20% by mass or less, more preferably 10% by mass or less.

[0642] The kneaded product may contain only one plasticizer or two or more plasticizers. When two or more plasticizers are contained, the total amount thereof is preferably within the above range.

[0643] <<Other additives>>

[0644] The composition of the present invention may contain any additives such as a processing stabilizer, an anti-aging agent, a compatibilizer, etc. as needed. By appropriately containing these components, various properties of the resulting cured product can be appropriately adjusted.

[0645] <Use of the composition>

[0646] The composition of the present invention can also be suitably used in applications where exposure to light, including sunlight or ultraviolet light, is possible. Specific examples include coating materials or films for window panes of buildings, facilities, and transportation equipment; interior and exterior decorative materials and coatings for buildings, facilities, and transportation equipment; 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 foods, chemicals, and pharmaceuticals; agricultural and industrial sheets; fiber products and fibers for clothing such as sportswear, stockings, and hats; lenses such as plastic lenses, contact lenses, spectacles, and prosthetic eyes, or their coating materials; optical products such as filters, prisms, mirrors, and photographic materials; stationery such as tapes and inks; signboards, markers, and their surface coating materials. For details, reference can be made to paragraphs 0158 to 0218 of Japanese Patent Application Laid-Open No. 2009-263617 and paragraphs 0161 to 0194 of Japanese Patent Application Laid-Open No. 2009-096971, and these contents are incorporated into this specification.

[0647] The composition of the present invention can be preferably used in optical components, etc. For example, it is preferably used as a composition for ultraviolet cutoff filters, lenses, or protective materials. The form of the protective material is not particularly limited, and examples thereof include coatings, films, sheets, etc. Furthermore, the composition of the present invention can also be used as a pressure-sensitive adhesive, a tackifier, etc.

[0648] Furthermore, the composition of the present invention can also be used in various components of display devices. For example, in the case of liquid crystal displays, it can be used in antireflection films, polarizer protective films, optical films, retardation films, pressure-sensitive adhesives, adhesives, and other components that constitute liquid crystal displays. Furthermore, in the case of organic electroluminescent displays, it can be used in optical films, polarizer protective films in circular polarizers, retardation films such as quarter-wave plates, adhesives, or pressure-sensitive adhesives, and other components that constitute organic electroluminescent displays.

[0649] <Cured Material and Its Application>

[0650] The cured product of the present invention can be obtained using the above-mentioned composition of the present invention. The "cured product" in this specification includes a dried product obtained by drying and curing the composition and a cured product obtained by curing the composition during a curing reaction.

[0651] The cured product of the present invention can be obtained as a molded body in which the composition is molded into a desired shape. The shape of the molded body can be appropriately selected according to use or purpose. For example, a coating film, a film, a sheet, a plate, a lens, a tubular, a fiber, etc. can be enumerated.

[0652] The cured product of the present invention can be suitably used as an optical component. Examples of the optical component include ultraviolet cut filters, lenses, protective materials, and the like. Furthermore, it can also be used for polarizing plates, etc.

[0653] The ultraviolet cut filter can be used for articles such as optical filters, display devices, solar cells, and window glass. The type of display device is not particularly limited, and examples thereof include liquid crystal display devices and organic electroluminescent display devices.

[0654] When the cured product of the present invention is used for a lens, the cured product of the present invention itself can be formed into a lens shape for use. Furthermore, the cured product of the present invention can be used as a coating on the surface of a lens, an intermediate layer (adhesive layer) of a cemented lens, etc. Regarding cemented lenses, examples include cemented lenses described in paragraphs 0094 to 0102 of International Publication No. 2019 / 131572, and the contents are incorporated into this specification.

[0655] The type of protective material is not particularly limited, and examples thereof include protective materials for display devices, protective materials for solar cells, protective materials for window glass, and organic electroluminescent displays. The shape of the protective material is not particularly limited, and examples thereof include coatings, films, and sheets.

[0656] <Optical Components>

[0657] The optical component of the present invention comprises a cured product obtained by using the above-mentioned composition of the present invention. The cured product of the present invention can be obtained as a molded body in which the above-mentioned composition of the present invention is molded into a desired shape. About the shape of the molded body, it is possible to suitably select according to use and purpose. For example, a coating film, a film, a sheet, a plate, a lens, a tubular, a fiber, etc. can be enumerated.

[0658] Examples of the types of optical components include ultraviolet cut filters, lenses, and protective materials.

[0659] The ultraviolet cut filter can be used for articles such as optical filters, display devices, solar cells, and window glass. The type of display device is not particularly limited, and examples thereof include liquid crystal display devices and organic electroluminescent display devices.

[0660] Examples of the lens include a lens in which the cured product of the present invention itself is formed into a lens shape; a lens in which the cured product of the present invention is used in a coating film on the lens surface, an intermediate layer (adhesive layer or pressure-sensitive adhesive layer) for bonding lenses, and the like.

[0661] The type of protective material is not particularly limited, and examples thereof include protective materials for display devices, solar cells, and window glass. The shape of the protective material is not particularly limited, and examples thereof include coatings, films, and sheets.

[0662] Furthermore, as one form of an optical component, a resin film can be cited. The resin film can be formed using the composition of the present invention, wherein the composition uses a compound containing a resin as a curable compound. As the resin of the composition for forming the resin film, the above-mentioned resins can be cited, preferably (meth) acrylic resins, polyester fibers, cycloolefin resins and cellulose acylate resins, more preferably cellulose acylate resins. The composition for forming the resin film can contain the additives described in paragraphs 0022 to 0067 of Japanese Patent Application Laid-Open No. 2012-215689. As such additives, for example, sugar esters can be cited. By adding a sugar ester compound to the composition for forming the resin film containing the cellulose acylate resin, the total haze and internal haze can be reduced without impairing the performance of the optical properties and without performing a heat treatment before the stretching process. Furthermore, a resin film (cellulose acylate film) using a composition containing a cellulose acylate resin can be manufactured by the method described in paragraphs 0068 to 0096 of Japanese Patent Application Laid-Open No. 2012-215689. Furthermore, a hard coating layer described in paragraphs 0097 to 0113 of JP-A-2012-215689 may be further laminated on the resin film.

[0663] Another embodiment of the optical component includes an optical component comprising a laminate of a support and a resin layer, wherein at least one of the support and the resin layer comprises the cured product of the present invention.

[0664] The thickness of the resin layer in the laminate is preferably 1 μm to 2500 μm, more preferably 10 μm to 500 μm.

[0665] The support in the laminate is preferably a material having transparency within a range that does not impair optical performance. Transparency of the support means optical transparency, specifically, a total light transmittance of 85% or greater. The total light transmittance of the support is preferably 90% or greater, more preferably 95% or greater.

[0666] As the support, a resin film can be given as a preferred example. As the resin constituting the resin film, an ester resin (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), polycyclohexane dimethylene terephthalate (PCT), etc.), an olefin resin (e.g., polypropylene (PP), polyethylene (PE), etc.), polyvinyl chloride (PVA), triacetyl cellulose (TAC), etc. can be given. Among them, from the viewpoint of versatility, PET is preferred.

[0667] The thickness of the support can be appropriately selected depending on the use or purpose, etc. Generally, the thickness is preferably from 5 μm to 2500 μm, more preferably from 20 μm to 500 μm.

[0668] Further, the above support can also use a support having peelability. Such a laminate is suitably used for a polarizing plate, etc. Here, the support having peelability means a support which can be peeled from the resin film. The stress at the time of 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, further preferably 0.11 N / 25 mm or more and 0.20 N / 25 mm or less. After the surface of the laminate cut to a width of 25 mm and a length of 80 mm is adhered and fixed to a glass substrate with an acrylic pressure-sensitive adhesive sheet, one end in the length direction (one side of 25 mm in width) of the test piece is gripped using a tensile testing machine (RTF-1210 manufactured by A&D Company, Limited), and a 90° peel test is performed at a crosshead speed (gripping moving speed) of 200 mm / minute in an atmosphere of 23°C in temperature and 60% in relative humidity in accordance with Japanese Industrial Standards (JIS) K 6854-1: 1999 "Adhesives - Peel adhesion strength test method - Part 1: 90 degree peel", whereby the stress at the time of peeling the support from the resin film is evaluated.

[0669] As the support having peelability, a support containing polyethylene terephthalate (PET) as a main component (a component having the largest content by mass among the components constituting the support) is preferred. 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, further preferably 40,000 or more. The weight average molecular weight of PET can be determined by dissolving the support in hexafluoroisopropanol (HFIP) and by the GPC method. The thickness of the support is not particularly limited, and is preferably from 0.1 to 100 μm, more preferably from 0.1 to 75 μm, further preferably from 0.1 to 55 μm, particularly preferably from 0.1 to 10 μm. Further, the support can be subjected to a corona treatment, a glow discharge treatment, a primer treatment, etc. as a publicly known surface treatment.

[0670] Further, as other forms of the optical member, a laminate in which a hard coat layer, a transparent support, and a pressure-sensitive adhesive layer or an adhesive layer are sequentially stacked can be given. Such a laminate can be suitably used as an ultraviolet cut filter, a protective material (a protective film, a protective sheet). In the optical member of this form, it is only necessary that any one of the support, the hard coat layer, and the pressure-sensitive adhesive layer or the adhesive layer contain the cured product of the present application described above.

[0671] As the hard coat layer, for example, the hard coat layers described in Japanese Patent Application Publication No. 2013-045045, Japanese Patent Application Publication No. 2013-043352, Japanese Patent Application Publication No. 2012-232459, Japanese Patent Application Publication No. 2012-128157, Japanese Patent Application Publication No. 2011-131409, Japanese Patent Application Publication No. 2011-131404, Japanese Patent Application Publication No. 2011-126162, Japanese Patent Application Publication No. 2011-075705, Japanese Patent Application Publication No. 2009-286981, Japanese Patent Application Publication No. 2009-263567, Japanese Patent Application Publication No. 2009-075248, Japanese Patent Application Publication No. 2007-164206, Japanese Patent Application Publication No. 2006-096811, Japanese Patent Application Publication No. 2004-075970, Japanese Patent Application Publication No. 2002-156505, Japanese Patent Application Publication No. 2001-272503, International Publication No. 2012 / 018087, International Publication No. 2012 / 098967, International Publication No. 2012 / 086659, and International Publication No. 2011 / 105594 can be used. From the viewpoint of further improving scratch resistance, the thickness of the hard coat layer is preferably 5 to 100 µm.

[0672] The optical component of this form has a pressure-sensitive adhesive layer or an adhesive layer on the side opposite to the side having the hard coat layer of the supporting substrate. The type of pressure-sensitive adhesive or adhesive used for the pressure-sensitive adhesive layer or adhesive layer is not particularly limited, and known pressure-sensitive adhesives or adhesives can be used. In addition, it is also preferred to use a substance containing an acrylic resin described in paragraphs 0056 to 0076 of Japanese Patent Application Publication No. 2017-142412 and a cross-linking agent described in paragraphs 0077 to 0082 of Japanese Patent Application Publication No. 2017-142412 in the pressure-sensitive adhesive or adhesive. In addition, the pressure-sensitive adhesive or adhesive may also include an adhesion improver (silane compound) described in paragraphs 0088 to 0097 of Japanese Patent Application Publication No. 2017-142412 and an additive described in paragraph 0098 of Japanese Patent Application Publication No. 2017-142412. The pressure-sensitive adhesive layer or the adhesive layer can be formed by the method described in paragraphs 0099 to 0100 of Japanese Patent Application Laid-Open No. 2017-142412. From the viewpoint of achieving both adhesive strength and workability, the thickness of the pressure-sensitive adhesive layer or the adhesive layer is preferably 5 μm to 100 μm.

[0673] The optical component of the present invention can be suitably used as a component of displays such as liquid crystal display devices (LCD) and organic electroluminescent display devices (OLED).

[0674] Examples of liquid crystal display devices include those containing the cured product of the present invention in components such as antireflection films, polarizer protective films, optical films, retardation films, pressure-sensitive adhesives, and pressure-sensitive adhesives. The optical component containing the cured product of the present invention can be positioned on either the viewer side (front side) or the backlight side of a liquid crystal cell, and can be positioned on either the side away from the liquid crystal cell (outer side) or the side closer to the liquid crystal cell (inner side) of a polarizer.

[0675] Examples of organic electroluminescent displays include those containing the cured product of the present invention in components such as optical films, polarizer protective films in circularly polarizing plates, retardation films such as quarter-wave plates, adhesives, and pressure-sensitive adhesives. Using the cured product of the present invention in such structures can suppress degradation of the organic electroluminescent display device due to external light.

[0676] Example

[0677] Hereinafter, the present invention will be further described in detail with reference to the following examples. The materials, usage amounts, ratios, treatment contents, treatment steps, etc. shown in the following examples can be appropriately changed without departing from the main purpose 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 formula shown below, Me is a methyl group, Et is an ethyl group, n Bu is n-butyl, tBu is a tert-butyl group, and Ph is a phenyl group.

[0678] <synthesis example>

[0679] Synthesis of intermediate 1-3 (synthesis example 1)

[0680] Intermediate 1-1 was synthesized according to the following scheme. In the following scheme, in synthesizing intermediate 1-1, the method described in paragraphs 0222 and 0223 of Japanese Patent Application Publication No. 2009-263617 was used with 1,2-dibenzylpyrazoline-3,5-dione instead of 1,2-dibutylpyrazoline-3,5-dione, and 77 g (yield 78%) of intermediate 1-1 was obtained.

[0681] [Chemical Formula 75]

[0682]

[0683] Next, intermediate 1-2 was synthesized according to the following synthesis scheme. After 50 g of intermediate 1-1, 24.5 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone, and 500 mL of tetrahydrofuran were mixed, stirring was performed at 20°C for 1 hour. After the reaction was completed, 500 mL of hexane was added, and the precipitated solid was filtered and washed with 150 mL of hexane, and 42 g (yield 84%) of intermediate 1-2 was obtained.

[0684] [Chemical Formula 76]

[0685]

[0686] Next, intermediate 1-3 was synthesized according to the following synthesis scheme. After 30 g of intermediate 1-2, 8 g of piperidinium pentamethylenedithiocarbamate, 360 mL of N-methyl-2-pyrrolidone, 160 mL of acetic acid, and 54 mL of acetone were mixed, stirring was performed at 60°C for 1 hour. The precipitated solid was filtered and washed with 300 mL of acetone, and 8.0 g of intermediate 1-3 (yield 36%) was obtained.

[0687] [Chemical Formula 77]

[0688]

[0689] Synthesis of compound A-104 (synthesis example 2)

[0690] Compound A-104 was synthesized according to the following synthetic scheme. After 3.0 g of intermediate 1-3, 0.58 g of malononitrile and 150 ml of N-methyl-2-pyrrolidone were added and mixed, stirring was performed at 80°C for 1 hour. After cooling to room temperature, 1 mL of hydrochloric acid and 150 ml of water were added, and stirring was performed for 30 minutes. After the precipitated solid was filtered, 200 ml of acetonitrile was added, and refluxing was performed under a nitrogen atmosphere for 1 hour. After cooling to room temperature, the solid was filtered after stirring at room temperature for 1 hour, and washed with 100 ml of acetonitrile, thereby obtaining 2.1 g of compound A-104 (yield 79%). Also, in the proton nuclear magnetic resonance spectrum (1H-NMR, solvent: deuterated dimethyl sulfoxide (dDMSO)) of the obtained compound A-104, the chemical shift δ was 11.6 (s, 2H), 7.29 (m, 10H), 4.80 (s, 4H). 1 H-NMR, solvent: deuterated dimethyl sulfoxide (dDMSO)) of the obtained compound A-104, the chemical shift δ was 11.6 (s, 2H), 7.29 (m, 10H), 4.80 (s, 4H).

[0691] [Chemical Formula 78]

[0692]

[0693] (Synthetic Example 3) Synthesis of Compound A-1

[0694] Compound A-1 was synthesized according to the following synthetic scheme. After 1.5 g of compound A-104, 0.76 g of triethylamine, 1.0 g of 2-ethylhexanoyl chloride and 30 ml of dimethylacetamide were added and mixed, stirring was performed at 20°C for 1 hour. After the reaction was completed, 30 ml of water was added, and stirring was performed for 30 minutes. After the precipitated solid was filtered, washing was performed with 30 ml of methanol, and then column chromatography purification was performed using silica gel, thereby obtaining 1.6 g (yield 75%) of compound A-1. Also, in the proton nuclear magnetic resonance spectrum (1H-NMR, solvent: deuterated chloroform (CDCl3)) of the obtained compound A-1, the chemical shift δ was 7.27 (m, 6H), 7.10 (m, 4H), 4.75 (s, 4H), 2.69 (m, 2H), 1.8-1.6 (m, 8H), 1.5-1.3 (m, 8H), 1.10 (m, 6H), 0.94 (m, 6H). 1 H-NMR, solvent: deuterated dimethyl sulfoxide (dDMSO)) of the obtained compound A-104, the chemical shift δ was 11.6 (s, 2H), 7.29 (m, 10H), 4.80 (s, 4H).

[0695] [Chemical Formula 79]

[0696]

[0697] <About Ultraviolet Absorbers>

[0698] In each of the following test examples, the example compounds (1) to (26) and comparative compounds (1) to (2) used as ultraviolet absorbers were each a compound having the following structure.

[0699] [Chemical Formula 80]

[0700]

[0701] [Chemical Formula 81]

[0702]

[0703] [Chemical Formula 82]

[0704]

[0705] [Chemical Formula 83]

[0706]

[0707] [Chemical Formula 84]

[0708]

[0709] [About Anti-fading Agents]

[0710] In each of the test examples shown below, the compounds T-1 to T-12 used as the anti-fading agent were compounds of the structures shown below, respectively.

[0711] [Chemical Formula 85]

[0712]

[0713] [Test Example 1]

[0714] Each composition was prepared by mixing the following components.

[0715] Ultraviolet absorber (compound (example compounds (1) to (21), comparative compounds (1) to (2) described in the table below)... 1.1 parts by mass

[0716] Resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, weight average molecular weight 95000)... 12.6 parts by mass Anti-fading agent (compound described in the table below)... 1.1 parts by mass Solvent (chloroform)... 85.2 parts by mass

[0717] [Table 1]

[0718] UV absorbers anti-fading agent Example 101 Example compound (1) T-1 Example 102 Example compound (1) T-2 Example 103 Example compound (1) T-7 Example 104 Example compound (1) T-8 Example 105 Example compound (1) T-9 Example 106 Example compound (1) T-10 Example 107 Example compound (2) T-1 Example 108 Example compound (3) T-3 Example 109 Example compound (4) T-4 Example 110 Example compound (5) T-5 Example 111 Example compound (6) T-6 Example 112 Example compound (7) T-2 Example 113 Example compound (8) T-1 Example 114 Example compound (9) T-3 Example 115 Example compound (10) T-4 Example 116 Example compound (11) T-5 Example 117 Example compound (12) T-6 Example 118 Example compound (13) T-2 Example 119 Example compound (14) T-1 Example 120 Example compound (15) T-3 Example 121 Example compound (16) T-4 Example 122 Example compound (17) T-5 Example 123 Example compound (18) T-1 Example 124 Example compound (18) T-2 Example 125 Example compound (18) T-3 Example 126 Example compound (18) T-7 Example 127 Example compound (18) T-8 Example 128 Example compound (18) T-9 Example 129 Example compound (18) T-10 Example 130 Example compound (19) T-1 Example 131 Example compound (19) T-2 Example 132 Example compound (19) T-4 Example 133 Example compound (19) T-7 Example 134 Example compound (19) T-8 Example 135 Example compound (19) T-9 Example 136 Example compound (19) T-10 Example 137 Example compound (20) T-1 Example 138 Example compound (20) T-2 Example 139 Example compound (20) T-5 Example 140 Example compound (20) T-7

[0719] [Table 2]

[0720] UV absorbers anti-fading agent Example 141 Example compound (20) T-8 Example 142 Example compound (20) T-9 Example 143 Example compound (20) T-10 Example 144 Example compound (21) T-1 Example 145 Example compound (21) T-2 Example 146 Example compound (21) T-6 Example 147 Example compound (21) T-7 Example 148 Example compound (21) T-8 Example 149 Example compound (21) T-9 Example 150 Example compound (21) T-10 Example 151 Example compound (18) T-11 Example 152 Example compound (19) T-11 Example 153 Example compound (21) T-11 Example 154 Example compound (18) T-12 Example 155 Example compound (19) T-12 Example 156 Example compound (21) T-12 Example 157 Example compound (22) T-1 Example 158 Example compound (22) T-2 Example 159 Example compound (23) T-1 Example 160 Example compound (23) T-2 Example 161 Example compound (24) T-1 Example 162 Example compound (24) T-2 Example 163 Example compound (25) T-1 Example 164 Example compound (25) T-2 Example 165 Example compound (26) T-1 Example 166 Example compound (26) T-2 Comparative Example 101 Comparative compound (1) T-1 Comparative Example 102 Comparative compound (1) T-2 Comparative Example 103 Comparative Compound (2) T-1 Comparative Example 104 Comparative Compound (2) T-2

[0721] Each of the obtained compositions was spin-coated on a glass substrate, and then dried at 110° C. for 2 minutes to prepare a film.

[0722] (Evaluation of long-wavelength ultraviolet absorption capacity)

[0723] The absorbance of the obtained films was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation). The maximum absorption wavelength (λmax) was determined from the absorption spectrum of each film, and the long-wavelength ultraviolet absorption capacity was evaluated according to the following criteria. The values ​​in parentheses in the long-wavelength ultraviolet absorption capacity column are the λmax values, and the values ​​in parentheses in the coloring column are the absorbance ratio A. 440 The value of .

[0724] -Evaluation criteria for long-wavelength ultraviolet absorption capacity-

[0725] A: λmax is 390nm or more

[0726] B: λmax is greater than or equal to 380 nm and less than 390 nm

[0727] C: λmax less than 380nm

[0728] (Evaluation of coloring properties)

[0729] The absorbance of the obtained film was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and the ratio of the absorbance at a wavelength of 440 nm to the absorbance at a wavelength of 400 nm was calculated (absorbance ratio A). 440 ), and the coloring properties were evaluated according to the following criteria (coloring properties 1). 440 Smaller values ​​indicate less shading.

[0730] Next, the obtained film was subjected to a light resistance test under the following condition 1. The absorbance of the film after the light resistance test was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and the value of the ratio of the absorbance at a wavelength of 440 nm to the absorbance at a wavelength of 400 nm was calculated (absorbance ratio A). 440 ) and evaluated the coloring properties according to the following criteria. The values ​​in brackets in the coloring property column are the absorbance ratio A 440 The absorbance ratio A 440 Smaller values ​​indicate less shading.

[0731] -Evaluation Criteria for Colorability-

[0732] A: Absorbance ratio A 440 Less than 0.01

[0733] B: absorbance ratio A 440 Greater than 0.01

[0734] C: absorbance ratio A 440 Greater than 0.02

[0735] -Condition 1-

[0736] Apparatus: Low-temperature cycle xenon lamp weathering tester (XL75, manufactured by Suga Test Instruments Co., Ltd.)

[0737] Illumination: 90klx(40w / m 2 )

[0738] Duration: 4 weeks

[0739] Environment: 23°C, relative humidity 50%

[0740] (Evaluation of light resistance)

[0741] Each film was subjected to a light resistance test under the above-mentioned condition 1, and the maintenance rate of the absorbance at the maximum absorption wavelength (λmax) was determined to evaluate the light resistance. Specifically, after measuring the absorbance of the film at λmax using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), the film was subjected to a light resistance test under condition 1, and the absorbance at λmax of the film after the light resistance test was measured. Next, using the absorbance values ​​of the film at λmax before and after the light resistance test, the absorbance maintenance rate (%) was calculated by the following formula, and the light resistance was evaluated according to the following criteria. The higher the absorbance maintenance rate, the better the light resistance. The evaluation results are shown in the following table. The values ​​in brackets in the light resistance column are the values ​​of the absorbance maintenance rate.

[0742] Absorbance maintenance rate (%) = (absorbance of the film at λmax after the light resistance test / absorbance of the film at λmax before the light resistance test) × 100

[0743] -Evaluation Criteria-

[0744] AA: Absorbance maintenance rate is above 90%

[0745] A: Absorbance maintenance rate is above 85%

[0746] B: Absorbance maintenance rate is 80% or more and less than 85%

[0747] C: Absorbance maintenance rate is less than 80%

[0748] [Table 3]

[0749]

[0750] [Table 4]

[0751]

[0752] As shown in the above table, Examples 101 to 166 are excellent in long-wavelength ultraviolet absorption. 440 The values ​​of are all small, and the evaluation of colorability is excellent. In addition, the absorbance maintenance rate after the light resistance test is also high, and the evaluation of light resistance is also excellent.

[0753] <Test Example 2>

[0754] The following ingredients were mixed to prepare a composition.

[0755] Ultraviolet absorber (compounds listed in the following table) ... 0.6 parts by mass

[0756] Polymerizable compound (KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., a compound having two or more ethylenically unsaturated bond-containing groups) ... 10.9 parts by mass

[0757] Resin (Dianal BR-80 (manufactured by Mitsubishi Chemical Corporation)) ... 13.4 parts by mass

[0758] Photopolymerization initiator (compound listed in the following table) ... 0.6 parts by mass Anti-fading agent (compound listed in the following table) ... 0.8 parts by mass Solvent (propylene glycol monomethyl ether acetate) ... 73.7 parts by mass

[0759] [Table 5]

[0760] UV absorbers anti-fading agent Photopolymerization initiator Example 201 Example compound (1) T-1 V-1 Example 202 Example compound (1) T-2 V-1 Example 203 Example compound (1) T-7 V-1 Example 204 Example compound (1) T-8 V-1 Example 205 Example compound (1) T-9 V-1 Example 206 Example compound (1) T-10 V-1 Example 207 Example compound (1) T-1 V-2 Example 208 Example compound (18) T-1 V-1 Example 209 Example compound (18) T-2 V-1 Example 210 Example compound (18) T-1 V-2 Example 211 Example compound (18) T-1 V-3 Example 212 Example compound (18) T-7 V-1 Example 213 Example compound (18) T-8 V-3 Example 214 Example compound (18) T-9 V-1 Example 215 Example compound (18) T-10 V-3 Example 216 Example compound (19) T-1 V-1 Example 217 Example compound (19) T-2 V-1 Example 218 Example compound (19) T-1 V-2 Example 219 Example compound (19) T-1 V-3 Example 220 Example compound (19) T-7 V-1 Example 221 Example compound (19) T-8 V-3 Example 222 Example compound (19) T-9 V-1 Example 223 Example compound (19) T-10 V-3 Example 224 Example compound (20) T-1 V-1 Example 225 Example compound (20) T-2 V-1 Example 226 Example compound (20) T-1 V-2 Example 227 Example compound (20) T-1 V-3 Example 228 Example compound (20) T-7 V-1 Example 229 Example compound (20) T-8 V-3 Example 230 Example compound (20) T-9 V-1 Example 231 Example compound (20) T-10 V-3 Example 232 Example compound (21) T-1 V-1 Example 233 Example compound (21) T-2 V-1 Example 234 Example compound (21) T-1 V-2 Example 235 Example compound (21) T-1 V-3 Example 236 Example compound (21) T-7 V-1 Example 237 Example compound (21) T-8 V-3 Example 238 Example compound (21) T-9 V-1 Example 239 Example compound (21) T-10 V-3

[0761] [Table 6]

[0762] UV absorbers anti-fading agent Photopolymerization initiator Example 240 Example compound (19) T-11 V-1 Example 241 Example compound (19) T-12 V-1 Example 242 Example compound (21) T-11 V-1 Example 243 Example compound (21) T-12 V-1 Example 244 Example compound (22) T-1 V-1 Example 245 Example compound (22) T-2 V-1 Example 246 Example compound (23) T-1 V-1 Example 247 Example compound (23) T-2 V-1 Example 248 Example compound (24) T-1 V-1 Example 249 Example compound (24) T-2 V-1 Example 250 Example compound (25) T-1 V-1 Example 251 Example compound (25) T-2 V-1 Example 252 Example compound (26) T-1 V-1 Example 253 Example compound (26) T-2 V-1 Comparative Example 201 Comparative compound (1) T-1 V-1 Comparative Example 202 Comparative compound (1) T-2 V-1 Comparative Example 203 Comparative compound (1) T-1 V-2 Comparative Example 204 Comparative Compound (2) T-1 V-1 Comparative Example 205 Comparative Compound (2) T-2 V-1 Comparative Example 206 Comparative Compound (2) T-1 V-2 Comparative Example 207 Comparative Compounds (3) T-2 V-3

[0763] (Photopolymerization initiator)

[0764] V-1: IrgaCure OXE01 (manufactured by BASF, oxime compound, photoradical polymerization initiator)

[0765] V-2: Omnirad 2959 (manufactured by IGM Resins BV, hydroxyacetophenone compound, photoradical polymerization initiator)

[0766] V-3: Omnirad TPO (manufactured by IGM Resins BV, acylphosphine compound, photoradical polymerization initiator)

[0767] Each composition was spin-coated onto a 50 mm × 50 mm glass substrate (1737, manufactured by Corning Incorporated Co., Ltd.) to a film thickness of 1.5 μm, and dried at 120°C for 5 minutes to form a composition layer. Subsequently, an i-ray stepper exposure apparatus (UX-1000SM-EH04, manufactured by Ushio Inc.) was used at a irradiation rate of 1000 mJ / cm 2 The entire surface of the composition layer was exposed to an exposure dose of 1000 Å to produce a film. In Examples 201 to 243, the change in transmittance at the maximum absorption wavelength (λmax) of the composition layer before and after exposure was 5% or less.

[0768] (Evaluation of coloring properties)

[0769] The colorability of the obtained film was evaluated by the same method and evaluation criteria as those in Test Example 1.

[0770] (Evaluation of light resistance)

[0771] The obtained film was subjected to a light resistance test under the following conditions 2. The absorbance maintenance rate of the film at the maximum absorption wavelength (λmax) before and after the light resistance test was determined by the same method as the light resistance evaluation in Test Example 1, and the light resistance was evaluated according to the following evaluation criteria.

[0772] -Condition 2-

[0773] Apparatus: Low-temperature cycle xenon lamp weathering tester (XL75, manufactured by Suga Test Instruments Co., Ltd.)

[0774] Illumination: 90klx(40w / m 2 )

[0775] Duration: 7 days

[0776] Environment: 23°C, relative humidity 50%

[0777] -Evaluation criteria for light resistance-

[0778] AA: Absorbance maintenance rate is more than 80%

[0779] A: Absorbance maintenance rate is above 70%

[0780] B: Absorbance maintenance rate is 60% or more and less than 70%

[0781] C: Absorbance maintenance rate is less than 60%

[0782] [Table 7]

[0783]

[0784] [Table 8]

[0785]

[0786] As shown in the above table, for Examples 201 to 253, the absorbance ratio A before and after the light resistance test was 440 The values ​​of are all small, and the evaluation of colorability is excellent. In addition, the absorbance maintenance rate after the light resistance test is also high, and the evaluation of light resistance is also excellent.

[0787] <Polymer Synthesis>

[0788] (Synthesis Example 101) Synthesis of Polymer P-1

[0789] [Chemical Formula 86]

[0790]

[0791] To a 200 mL three-necked flask, 100 mg of compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm), 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred at 80°C for 30 minutes under a nitrogen stream. 200 mg of 2,2'-azobis(isobutyric acid)dimethyl ester (V-601, manufactured by FUJIFILM Wako Pure Chemical Corporation (hereinafter referred to as V-601)) was added to the solution, and after stirring at 80°C for 6 hours, the mixture was cooled to room temperature. The obtained reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropanol, and the mixture was allowed to stand overnight. The precipitate was filtered out and washed with a mixture of hexane and isopropanol. 140 mL of hexane and 60 mL of isopropanol were added to the obtained powder, and after stirring at room temperature for 1 hour, the mixture was allowed to stand at room temperature overnight. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50° C. to obtain 7.0 g of the target polymer P-1. The number average molecular weight of the obtained polymer P-1 was 27,500 (in terms of polystyrene).

[0792] 100 mg of the obtained polymer P-1 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-1 was 399 nm (absorbance 1.61).

[0793] The polymer P-1 sufficiently shields light of a wavelength around 400 nm. Further, the polymer P-1 is less colored.

[0794] (Synthetic Example 102) Synthesis of Polymer P-2

[0795] [Chemical Formula 87]

[0796]

[0797] To a 200 mL three-necked flask were added 100 mg of the compound A-142 (λmax (in ethyl acetate) : 394 nm), 100 mg of 2-[2-hydroxy-5-(2-methacryloyloxyethyl)phenyl]2H- benzo[d][l,2,3]triazole (λmax (in ethyl acetate) : 338 nm) as an ultraviolet absorber, 9.8 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate, and stirring was performed at 80°C for 6 hours under a stream of nitrogen. After cooling to room temperature, the obtained reaction mixture was slowly added to a mixture of hexane 140 mL and isopropyl alcohol 60 mL, and left to stand for 1 night. The precipitated product was filtered off, and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder were added 140 mL of hexane and 60 mL of isopropyl alcohol, and after stirring at room temperature for 1 hour, left to stand at room temperature for 1 night. The precipitate was filtered off, washed with a mixture of hexane and isopropyl alcohol, and dried at 50°C to obtain 5.0 g of the target polymer P-2. The number average molecular weight of the obtained polymer P-2 was 33400 (polystyrene conversion).

[0798] The obtained 150 mg of the polymer P-2 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The polymer P-2 had a λmax of 399 nm (absorbance 1.45) and 343 nm (absorbance 0.83). The polymer P-2 sufficiently shields light of a wavelength around 400 nm. Further, it is excellent in the shielding property of light of a wavelength shorter than 350 nm. Further, the polymer P-2 is less colored.

[0799] (Synthetic Example 103) Synthesis of Polymer P-3

[0800] [Chemical Formula 88]

[0801]

[0802] To a 200 mL three-necked flask, 100 mg of compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm), 9.9 g of butyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred at 80°C for 30 minutes under a nitrogen stream. 20 mg of 2,2'-azobis(isobutyric acid)dimethyl ester (V-601, manufactured by FUJIFILM Wako Pure Chemical Corporation (hereinafter referred to as V-601)) was added to the solution, and after stirring at 80°C for 6 hours, the mixture was cooled to room temperature. The obtained reaction mixture was slowly added to a mixture of 200 mL of methanol and allowed to stand overnight. The precipitated precipitate was filtered and washed with a mixture of chloroform and methanol. 20 mL of chloroform and 200 mL of methanol were added to the obtained powder, and after stirring at room temperature for 1 hour, the mixture was allowed to stand at room temperature overnight. The precipitate was collected by filtration, washed with a mixture of chloroform and methanol, and dried at 50° C. to obtain 5.2 g of the target polymer P-3. The number average molecular weight of the obtained polymer P-3 was 96,000 (in terms of polystyrene).

[0803] 100 mg of the obtained polymer P-3 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of polymer P-3 was 399 nm (absorbance 1.56). Polymer P-3 was able to fully shield light with a wavelength near 400 nm. In addition, polymer P-3 had little coloration.

[0804] (Synthesis Example 104) Synthesis of Polymer P-4

[0805] [Chemical Formula 89]

[0806]

[0807] To a 200 mL three-necked flask, 100 mg of compound A-232 (maximum absorption wavelength (in ethyl acetate solution): 391 nm), 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred at 80°C for 30 minutes under a nitrogen stream. 200 mg of 2,2'-azobis(isobutyric acid)dimethyl ester (V-601, manufactured by FUJIFILM Wako Pure Chemical Corporation (hereinafter referred to as V-601)) was added to the solution, and after stirring at 80°C for 6 hours, the mixture was cooled to room temperature. The obtained reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropanol and allowed to stand overnight. The precipitated precipitate was filtered and washed with a mixture of hexane and isopropanol. 140 mL of hexane and 60 mL of isopropanol were added to the obtained powder, and after stirring at room temperature for 1 hour, the mixture was allowed to stand at room temperature overnight. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50° C. to obtain 7.4 g of the target polymer P-4. The number average molecular weight of the obtained polymer P-4 was 29,500 (in terms of polystyrene).

[0808] 100 mg of the obtained polymer P-4 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of polymer P-4 was 397 nm (absorbance 1.57). Polymer P-4 was able to fully shield light with a wavelength near 400 nm. In addition, polymer P-4 had little coloration.

[0809] (Synthesis Example 105) Synthesis of Polymer P-5

[0810] [Chemical formula 90]

[0811]

[0812] To a 200 mL three-necked flask, 100 mg of Compound A-352 (λmax(absorption wavelength) (in ethyl acetate solution): 392 nm), 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added, and stirred at 80°C for 30 minutes under a stream of nitrogen. To the solution, 200 mg of 2,2'-azobis(isobutyric acid) dimethyl ester (V-601, manufactured by FUJIFILM Wako Pure Chemical Corporation (hereinafter, referred to as V-601)) was added, and stirred at 80°C for 6 hours, and then cooled to room temperature. The obtained reaction mixture was slowly added to a mixture of hexane 140 mL and isopropyl alcohol 60 mL, and left to stand for 1 night. The precipitated was filtered, and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140 mL of hexane and 60 mL of isopropyl alcohol were added, and stirred at room temperature for 1 hour, and then left to stand at room temperature for 1 night. The precipitate was filtered, washed with a mixture of hexane and isopropyl alcohol, and dried at 50°C to obtain 7.8 g of the target polymer P-5. The number average molecular weight of the obtained polymer P-5 was 45,000 (polystyrene conversion).

[0813] The obtained 100 mg of polymer P-5 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The λmax(absorption wavelength) of the polymer P-5 was 397 nm (absorbance 1.47).

[0814] The polymer P-5 sufficiently blocked light of a wavelength around 400 nm. Also, the polymer P-5 was less colored.

[0815] (Synthetic Example 101) Synthesis of Polymer P-6

[0816] [Chemical Formula 91]

[0817]

[0818] To a 200 mL three-necked flask, 104 mg of 2-[2-hydroxy-5-(2-methacryloyloxyethyl)phenyl]2H-benzo[d][1,2,3]triazole, 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred at 80°C for 30 minutes under a nitrogen stream. 135 mg of V-601 was added to the solution, and the mixture was stirred at 80°C for 4 hours. 37 mg of V-601 was further added, and the mixture was stirred at 90°C for 2 hours, then cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropanol. The precipitate was filtered and washed with a mixture of hexane and isopropanol. 140mL of hexane and 60mL of isopropanol were added to the obtained powder, and after stirring at room temperature for 3 hours, the precipitate was filtered out, washed with a mixture of hexane and isopropanol, and dried at 50°C to obtain 8.1g of the target polymer P-6. The number average molecular weight of the obtained polymer P-6 was 14100 (polystyrene conversion). 150mg of polymer P-6 was dissolved in 100mL of chloroform and the absorption spectrum was measured. The maximum absorption wavelength of polymer P-6 was 339nm (absorbance 0.91). The shielding property of polymer P-6 to light of wavelength 380 to 400nm was low.

[0819] <Test Example 3>

[0820] (Examples 301 to 310, Comparative Examples 301 and 302)

[0821] 500 mg of the polymer described in the table below, 5.1 mg of the anti-fading agent described in the table below, 7.6 g of chloroform, and 1.1 g of a polymethyl methacrylate resin (Dianal BR-80 (containing 60% by mass or more of methyl methacrylate as a monomer unit, weight average molecular weight: 95,000, acid value: 0 mgKOH / g, manufactured by Mitsubishi Chemical Corporation) were dissolved to prepare a composition (resin composition (resin solution)). The obtained composition was spin-coated on a glass substrate, and the coated film was dried at 60°C for 2 minutes to form a film with a thickness of approximately 10 μm.

[0822] The films obtained using the compositions of Examples 301 to 308 showed little coloration and excellent shielding properties against light with a wavelength of approximately 400 nm. On the other hand, the films obtained using the compositions of Comparative Examples 301 and 302 showed low shielding properties against light with a wavelength of 380 to 400 nm.

[0823] (Evaluation of coloring properties)

[0824] The colorability was evaluated in the same manner as the evaluation of colorability in Test Example 1 and the evaluation criteria.

[0825] (Evaluation of light resistance)

[0826] The light resistance was evaluated in the same manner as the evaluation of light resistance in Test Example 1 and the evaluation criteria, except that a light resistance test was performed under the following Condition 3, with respect to the obtained film.

[0827] -Condition 3-

[0828] Apparatus: Low-temperature cycle xenon lamp weatherometer (Suga Test Instruments Co., XL75)

[0829] Irradiance: 90 klx (40 w / m 2 )

[0830] Time: 4 weeks

[0831] Environment: 23°C, relative humidity 5%

[0832] [Table 9]

[0833]

[0834] As shown in the above table, with respect to Examples 301 to 310, the values of absorbance ratio A 440 were all small before and after the light resistance test, and the evaluation of colorability was excellent. Furthermore, the absorbance retention rate after the light resistance test was also high, and the evaluation of light resistance was also excellent.

[0835] (Test Example 4)

[0836] A composition was prepared by dissolving and mixing 120 mg of the ultraviolet absorber described in the following table, the anti-fading agent described in the following table, 120 mg of Irgacure OXE01 (manufactured by BASF, an oxime compound, a photoradical polymerization initiator), 15.9 g of propylene glycol methyl ether acetate, 2.84 g of a (meth)acrylic acid-based resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95000), and 2.32 g of KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., a compound having two or more groups containing ethylenic unsaturation).

[0837] [Table 10]

[0838]

[0839] Each composition was spin-coated onto a 50 mm × 50 mm glass substrate (1737, manufactured by Corning Incorporated Co., Ltd.) to a film thickness of 1.5 μm, and dried at 120°C for 5 minutes to form a composition layer. Subsequently, an i-ray stepper exposure apparatus (UX-1000SM-EH04, manufactured by Ushio Inc.) was used at a irradiation rate of 1000 mJ / cm 2 The entire surface of the composition layer was exposed to an exposure dose of 1000 Å to produce a film. In Examples 401 to 421, the change in transmittance at the maximum absorption wavelength (λmax) of the composition layer before and after exposure was 5% or less.

[0840] (Evaluation of coloring properties)

[0841] The colorability of the obtained film was evaluated by the same method and evaluation criteria as those in Test Example 1.

[0842] (Evaluation of light resistance)

[0843] The obtained film was evaluated for light resistance by the same method and evaluation criteria as those used in Test Example 2.

[0844] [Table 11]

[0845]

[0846] As shown in the above table, for Examples 401 to 436, the absorbance ratio A before and after the light resistance test was 440 The values ​​of are all small, and the evaluation of colorability is excellent. In addition, the absorbance maintenance rate after the light resistance test is also high, and the evaluation of light resistance is also excellent.

Claims

1. A composition comprising an ultraviolet absorber, a curable compound and an anti-fading agent, The ultraviolet absorber comprises at least one selected from the group consisting of a compound represented by formula (1) and a polymer comprising a structure derived from the compound represented by formula (1). The anti-fading agent comprises at least one selected from the group consisting of an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex, and a benzolactone compound; In formula (1), Q 1 represents a group represented by formula (Q-1); Q 2 Indicates =0, =S, =NR q1 or =CR q2 R q3 , R q1 ~R q3 Each independently represents a hydrogen atom or a substituent, R q2 With R q3 are optionally bonded to each other to form a ring, wherein In R q2 With R q3 When the two groups are bonded to form a ring, =CR q2 R q3 With Q 1 Not the same structure; R 1 and R 2 each independently represents a hydrogen atom or a substituent; X 1 ~X 4 Each independently represents -S-, -NR X1 - or -SO2-, R X1 represents a hydrogen atom or an alkyl group; In formula (Q-1), * represents a connecting 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; Among them, when R 101 or R 102 When any one of them is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond, When R 101 or R 102 When any one of them is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 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, When R 101 or R 102 When any one of them is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group having a substituent, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

2. The composition according to claim 1, wherein The compound represented by the formula (1) is a compound represented by the formula (3); In formula (3), Q 3 represents a group represented by the formula (Q-1); Q 4 Indicates =O, =S, =NR q11 or =CR q12 R q13 , R q11 ~R q13 Each independently represents a hydrogen atom or a substituent, R q12 With R q13 can be bonded to each other to form a ring, wherein R q12 With R q13 When the two groups are bonded to form a ring, =CR q12 R q13 With Q 3 Not the same structure; R 11 and R 12 Each independently represents -OH, -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.

3. The composition according to claim 1 or 2, wherein The anti-fading agent comprises at least one selected from the group consisting of a compound represented by formula (Ao1-1) and a compound represented by formula (Ao2-1); In formula (Ao1-1), R a1 ~R a4 each independently represents a hydrogen atom, an alkyl group or an alkenyl group, X a1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group or an oxygen free radical, X a2 represents the atomic groups required to form a 5- to 7-membered ring; In formula (Ao2-1), R p1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or -Si(R p101 )(R p102 )(R p103 ), R p101 ~R p103 each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group or an aryloxy group, R p2 ~R p6 each independently represents a hydrogen atom or a substituent, R p1 ~R p6 Two adjacent groups in the group are optionally bonded to each other to form a ring; Among them, R p1 ~R p6 Not all of them are hydrogen atoms.

4. The composition according to claim 1 or 2, wherein The anti-fading agent comprises at least one selected from the group consisting of a compound represented by formula (Ao1-2) and a compound represented by formula (Ao2-2); In formula (Ao1-2), X a1i represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxyl group or an oxygen free radical, R a11 represents a substituent; In formula (Ao2-2), R p11 ~R p14 each independently represents a hydrogen atom, an alkyl group or an alkenyl group, Y p11 represents an aryl group, a heteroaryl group, or a group containing an ethylenically unsaturated bond.

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

6. The composition according to claim 1 or 2, wherein The curable compound includes a resin, and the resin is at least one selected from (meth)acrylic resins, polystyrene resins, polyester resins, polyurethane resins, thiourethane resins, polyimide resins, epoxy resins, polycarbonate resins, phthalate resins, cellulose acylate resins, and cycloolefin resins.

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

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