Compound

Abstract

To provide a novel compound which has high absorption selectivity for the long-wavelength ultraviolet to near ultraviolet regions close to a wavelength of 400 nm, exhibits high weathering resistance, and has a merocyanine skeleton, wherein a layer formed from a composition containing the compound can provide a thin film layer which has excellent light absorption in the regions without causing bleeding of the compound even when the quantity of the compound added to the composition is increased.SOLUTION: Provided is a compound having a polymerizable group and a partial structure represented by formula (X) [In the formula (X), a ring W1 denotes a ring structure which has a double bond as a constituent element of the ring and is not aromatic, and the ring W1 may have a substituent group. R3 denotes a monovalent substituent group].SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound. [Background technology]

[0002] UV absorbers have traditionally been used in a variety of applications and products to protect the human body and resin materials from UV degradation. UV absorbers can be broadly divided into inorganic and organic types. While inorganic UV absorbers offer good durability, such as weather resistance and heat resistance, they tend to lack control over absorption wavelength and compatibility with organic materials. Organic UV absorbers, on the other hand, are less durable than inorganic UV absorbers, but the flexibility of their molecular structure allows for control over absorption wavelength and compatibility with organic materials. These absorbers are used in a wide range of applications, including sunscreens, paints, optical materials, building materials, and automotive materials.

[0003] Typical organic ultraviolet absorbers include compounds having a triazole skeleton, a benzophenone skeleton, and a triazine skeleton. However, many organic ultraviolet absorbers having such skeletons exhibit maximum absorption (λmax) at wavelengths of 360 nm or less, and therefore cannot efficiently absorb light in the long-wave ultraviolet to near-ultraviolet wavelength range of around 400 nm (for example, wavelengths of 380 nm to 400 nm). In order to sufficiently absorb light in this range, a very large amount must be used. However, there is a problem in that increasing the amount used causes the ultraviolet absorber to precipitate from a composition containing the ultraviolet absorber.

[0004] For example, Patent Document 1 proposes a compound having a merocyanine skeleton represented by the following formula as a compound that efficiently absorbs light with a wavelength of around 400 nm. [ka] [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 2019-089997 Summary of the Invention [Problem to be solved by the invention]

[0006] However, compounds having a merocyanine skeleton have poor durability (particularly weather resistance) and are difficult to apply to applications where strict weather resistance is required, and the weather resistance of the compound described in Patent Document 1 was also insufficient in some cases. Furthermore, if the amount added is increased to sufficiently absorb light with a wavelength of around 400 nm, there is a possibility that the compound will precipitate. [Means for solving the problem]

[0007] The present invention includes the following inventions. [1] A compound having a polymerizable group and a partial structure represented by the following formula (X): [ka] [In formula (X), ring W 1 represents a ring structure having a double bond as a ring component and not having aromaticity, and ring W 1 may have a substituent. R 3 represents a monovalent substituent. [2] The compound according to [1], wherein the compound having a polymerizable group and a partial structure represented by formula (X) is any one of the compounds represented by formula (I) to formula (IX). [ka] [ka] [In formulas (I) to (IX), ring W 1 and R 3 represents the same meaning as above. Ring W 2 , Tamaki W 3 , Tamaki W 4, Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 Each independently represents a ring structure having at least one double bond as a ring component. 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 may have a substituent. Ring W 111 represents a heterocycle having two nitrogen atoms as its constituent elements. Ring W 112 , Tamaki W 113 and Ring W 114 each independently represents a ring having one nitrogen atom as a constituent element. R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 , R 92 , R 102 and R 112each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SF5, -SF3, -SO3H, -SO2H, a group containing a polymerizable group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH2- and -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group each independently represent -NR 12A -, -SO2-, -CO-, -O-, -COO-, -OCO-, -CONR 13A -, -NR 14A It may be substituted with -CO-, -S-, -SO-, -SO2-, -CF2- or -CHF-. R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 each independently represent a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SF5, -SF3, -SO3H, -SO2H, a group containing a polymerizable group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH2- and -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group each independently represent -O-, -S-, or -NR 1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR 2A -, -O-CO-NR 3A -, -NR 4A -CO-, -NR 5A -CO-O-, -NR 6A -CO-NR 7A -, -CO-S-, -S-CO-S-, -S-CO-NR 8A -, -NR 9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR 10A -CS-, -NR 11AIt may be substituted by -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO2-. R 1A , R 2A , R 3A , R 4A , R 5A , R 6A , R 7A , R 8A , R 9A , R 10A , R 11A , R 12A , R 13A and R 14A each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 , R 124 , R 5 , R 15 , R 25 , R 35 , R 75 , R 85 and R 125 each independently represents a group containing an electron-withdrawing group or a polymerizable group. R 1 and R 2 may be bonded to each other to form a ring. R 41 and R 42 may be bonded to each other to form a ring. R 51 and R 52 may be bonded to each other to form a ring. R 61 and R 62 may be bonded to each other to form a ring. R 91 and R 92 may be bonded to each other to form a ring. R 101 and R 102may be bonded to each other to form a ring. R 111 and R 112 may be bonded to each other to form a ring. R 2 and R 3 may be bonded to each other to form a ring. R 12 and R 13 may be bonded to each other to form a ring. R 42 and R 43 may be bonded to each other to form a ring. R 52 and R 53 may be bonded to each other to form a ring. R 62 and R 63 may be bonded to each other to form a ring. R 72 and R 73 may be bonded to each other to form a ring. R 82 and R 83 may be bonded to each other to form a ring. R 92 and R 93 may be bonded to each other to form a ring. R 102 and R 103 may be bonded to each other to form a ring. R 112 and R 113 may be bonded to each other to form a ring. R 4 and R 5 may be bonded to each other to form a ring. R 14 and R 15 may be bonded to each other to form a ring. R 24 and R 25 may be bonded to each other to form a ring. R 34 and R 35 may be bonded to each other to form a ring. R 74 and R 85 may be bonded to each other to form a ring. R 84 and R 85 may be bonded to each other to form a ring. R 124 and R 125 may be bonded to each other to form a ring. R 6 and R 8 each independently represents a divalent linking group. R 7 and R 126 each independently represents a single bond or a divalent linking group. R 9 and R 10 each independently represents a trivalent linking group. R 11 represents a tetravalent linking group. However, in formula (I), R 1 , R 2 , R 4 and R 5 At least one of the groups represents a group containing a polymerizable group. In formula (II), R 2 , R 4 , R 5 , R 12 , R 13 , R 14 and R 15 At least one of the groups represents a group containing a polymerizable group. In formula (III), R 4 , R 5 , R 23 , R 24 and R 25 At least one of the groups represents a group containing a polymerizable group. In formula (IV), R 4 , R 5 , R 33 , R 34 and R 35 At least one of the groups represents a group containing a polymerizable group. In formula (V), R 1 , R 2 , R 4 , R 41 , R 42 , R 43 and R 44At least one of the groups represents a group containing a polymerizable group. In formula (VI), R 1 , R 2 , R 4 , R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 and R 64 At least one of the groups represents a group containing a polymerizable group. In formula (VII), R 2 , R 4 , R 5 , R 72 , R 73 , R 74 , R 75 , R 82 , R 83 , R 84 and R 85 At least one of the groups represents a group containing a polymerizable group. In formula (VIII), R 1 , R 2 , R 4 , R 91 , R 92 , R 93 , R 94 , R 101 , R 102 , R 103 , R 104 , R 111 , R 112 , R 113 and R 114 At least one of the groups represents a group containing a polymerizable group. In formula (IX), R 2 , R 4 , R 5 , R 123 , R 124 and R 125 At least one of the groups represents a group containing a polymerizable group.] [3]R 4 and R 5 At least one selected from the group consisting of a nitro group, a cyano group, a halogen atom, -OCF3, -SCF3, -SF5, -SF3, a fluoroalkyl group, a fluoroaryl group, -CO-OR222 or -SO2-R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. [4]R 4 and R 5 At least one selected from the group consisting of a nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF3, -SCF3, a fluoroalkyl group, -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. [5]R 4 and R 5 At least one selected from the group consisting of a cyano group, -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. [6]R 4 and R 5 The compound according to any one of [2] to [5], wherein at least one selected from the group consisting of: is a cyano group. [7]R 4 is a cyano group, R 5 is a cyano group, -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. [8]R 4 and R 5 and each represent a cyano group. [9]R1 and R 2 are each independently an optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms.

[10] R 1 and R 2 The compound according to any one of [2] to [8], wherein

[11] R 1 and R 2 The compound according to

[10] , wherein the ring formed by linking these is an aliphatic heterocycle.

[12] R 1 and R 2 The compound according to any one of [2] to [9], wherein at least one selected from the group consisting of: is a group containing a polymerizable group.

[13] R 1 and R 2 are linked together to form a ring, and R 1 and R 2 The compound according to any one of [2] to [8], wherein the rings linked to each other have a polymerizable group.

[14] Tamaki W 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 are each independently a ring having no aromaticity.

[15] Tamaki W 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 are each independently a 5- to 7-membered ring structure.

[16] Tamaki W 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 are each independently a six-membered ring structure.

[17] R 3 is a nitro group, cyano group, halogen atom, -OCF3, -SCF3, -SF5, -SF3, fluoroalkyl group, fluoroaryl group, -CO-OR 111A or -SO2-R 112A (R 111A and R 112A and each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.

[18] R 3 is a cyano group, a fluorine atom, a chlorine atom, -OCF3, -SCF3, a fluoroalkyl group, -CO-OR 111A or -SO2-R 112A (R 111A and R 112A and each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.

[19] R 3 The compound according to any one of [1] to

[18] , wherein

[20] Tamaki W 1 The compound according to any one of [1] to

[19] , wherein is a 5- to 7-membered ring.

[21] Tamaki W 1

[20] The compound according to

[20] , wherein

[22] The compound according to any one of [1] to

[21] , which has a gram absorption coefficient ε of 50 L / (g·cm) or more at the maximum absorption wavelength.

[23] The compound according to any one of [1] to

[22] , wherein ε(λmax) / ε(λmax+30 nm)≧5. [ε(λmax) represents the gram absorption coefficient at the maximum absorption wavelength of a compound having a polymerizable group and a partial structure represented by formula (X)]. ε(λmax+30 nm) represents the gram absorption coefficient at (maximum absorption wavelength+30 nm) of a compound having a polymerizable group and a partial structure represented by formula (X). The unit of gram extinction coefficient is L / (g·cm).

[24] A composition comprising the compound according to any one of [1] to

[23] .

[25] The composition according to

[24] , further comprising an initiator.

[26] The composition according to

[25] , wherein the initiator is a radical polymerization initiator.

[27] The composition according to

[26] , wherein the initiator is a photoradical polymerization initiator.

[28] The composition according to any one of

[24] to

[27] , further comprising a radically polymerizable component.

[29] The composition according to

[28] , wherein the radical polymerizable component is a (meth)acrylate compound.

[30] The composition according to

[29] , wherein the radical polymerizable component is a polyfunctional (meth)acrylate compound.

[31] The composition according to any one of

[24] to

[30] , further comprising a resin (A).

[32] The composition according to

[31] , wherein the resin (A) is a resin having a glass transition temperature of 40°C or less.

[33] The composition according to

[32] , wherein the resin having a glass transition temperature of 40°C or less is a (meth)acrylic resin.

[34] The composition according to any one of

[31] to

[33] , further comprising a crosslinking agent (E).

[35] The composition according to

[34] , wherein the crosslinking agent (E) is an isocyanate crosslinking agent.

[36] A hard coat layer formed from the composition according to any one of

[24] to

[30] .

[37] A pressure-sensitive adhesive layer comprising the composition according to any one of

[31] to

[35] .

[38] A molded article formed from the composition according to

[24] .

[39] A resin having a partial structure represented by formula (X). [ka] [In formula (X), ring W 1 represents a ring structure having a double bond as a ring component and not having aromaticity, and ring W 1 may have a substituent. R 3 represents a monovalent substituent.

[40] A composition comprising the resin according to

[39] . [Effects of the Invention]

[0008] The present invention provides a novel compound having a merocyanine skeleton that exhibits high absorption selectivity in the long-wave ultraviolet to near-ultraviolet wavelength range around 400 nm and is highly weather-resistant. Furthermore, a layer formed from a composition containing the compound of the present invention can provide a thin film layer with excellent light absorption in the above range without bleeding of the compound even when the amount added to the composition is increased. DETAILED DESCRIPTION OF THE INVENTION

[0009] The compound of the present invention is a compound having a polymerizable group and a partial structure represented by formula (X) (hereinafter, may be referred to as compound (X)). [ka] [In formula (X), ring W 1 represents a ring structure having a double bond as a ring component and not having aromaticity. Ring W 1 may have a substituent. R 3 represents a monovalent substituent.

[0010] The polymerizable group possessed by compound (X) is not particularly limited. Examples include cationically polymerizable groups such as epoxy groups, oxetanyl groups, oxazolino groups, aziridino groups, and vinyl ether groups; radically polymerizable groups such as ethylenically unsaturated groups; and alkoxysilyl groups. The polymerizable group possessed by compound (X) is preferably a radically polymerizable group such as an ethylenically unsaturated group. Specific examples of the ethylenically unsaturated group include vinyl groups, α-methylvinyl groups, (meth)acryloyl groups, (meth)acryloyloxy groups, allyl groups, styryl groups, and (meth)acrylamide groups. In this specification, the term "(meth)acryloyl group" means either an acryloyl group or a methacryloyl group, and the "(meth)" in terms such as "(meth)acrylate" has the same meaning.

[0011] Ring W 1 is not particularly limited as long as it is a ring having one or more double bonds as a ring component and is not aromatic. 1 may be a single ring or a condensed ring. Ring W 1 may be a heterocyclic ring containing a heteroatom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a ring constituent, or may be an aliphatic hydrocarbon ring consisting of carbon atoms and hydrogen atoms. Ring W 1 has one or more double bonds as a ring constituent, but ring W 1 The number of double bonds contained in the formula is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0012] Ring W 1 is usually a ring having 5 to 18 carbon atoms, preferably a 5- to 7-membered ring structure, and more preferably a 6-membered ring structure. Ring W 1 is preferably a monocyclic ring.

[0013] Ring W 1 Examples of the group include the groups described below. [ka]

[0014] [ka]

[0015] [ka] [In the formula, *1 represents a bond to the nitrogen atom, and *2 represents a bond to the carbon atom.]

[0016] Ring W 1The substituent may have a substituent, and examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; alkyl groups having 1 to 12 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group; halogenated alkyl groups having 1 to 12 carbon atoms such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, and a 1,1,2,2,2-pentafluoroethyl group; alkoxy groups having 1 to 12 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group; and alkyl groups having 1 to 12 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group. Examples of such groups include a chiral thiol group; a fluorinated alkoxy group having 1 to 12 carbon atoms, such as a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2-fluoroethoxy group, or a 1,1,2,2,2-pentafluoroethoxy group; an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms, such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, or a methylethyl group; an alkylcarbonyloxy group having 2 to 12 carbon atoms, such as a methylcarbonyloxy group or an ethylcarbonyloxy group; an alkylsulfonyl group having 1 to 12 carbon atoms, such as a methylsulfonyl group or an ethylsulfonyl group; an arylsulfonyl group having 6 to 12 carbon atoms, such as a phenylsulfonyl group; a group containing a polymerizable group; a cyano group; a nitro group; a hydroxy group; a thiol group; a carboxyl group; -SF3; -SF5; or -SO3H.

[0017] The group containing a polymerizable group is not particularly limited as long as it is a group having a polymerizable group at its terminal, and specific examples thereof include groups represented by formula (I-2). [ka] [In formula (I-2), X 2 represents a polymerizable group. R 333represents a single bond, an alkanediyl group having 1 to 12 carbon atoms which may have a substituent, or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH2- contained in the alkanediyl group or the divalent aromatic hydrocarbon group is -O-, -CO-, -CS- or -NR 334 - may be replaced with R 334 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. * represents a bond.]

[0018] X 2 Examples of the polymerizable group represented by the formula (I) include the same polymerizable groups as those described above, and are preferably radically polymerizable groups, more preferably (meth)acryloyl groups.

[0019] R 333 Examples of the alkanediyl group having 1 to 12 carbon atoms represented by the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, an ethane-1,1-diyl group, a propane-1,2-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. R 333 The alkanediyl group having 1 to 12 carbon atoms represented by the following formula may have a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, a hydroxy group or the like.

[0020] R 333 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula include a phenylene group, a naphthylene group, and a phenylenemethylene group. R 333 The divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula (I) may have a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, a hydroxy group or the like. R 334Examples of the alkyl group having 1 to 6 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, and an isohexyl group.

[0021] Ring W 1 The substituent that may be possessed by is preferably an amino group optionally substituted by an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.

[0022] R 3 The monovalent substituent represented by the formula (I) is not particularly limited as long as it is not a hydrogen atom. Examples thereof include a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SF5, -SF3, -SO3H, -SO2H, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, and an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. In addition, -CH2- and -CH= contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group each independently represent -O-, -S-, or -NR 1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR 2A -, -O-CO-NR 3A -, -NR 4A -CO-, -NR 5A -CO-O-, -NR 6A -CO-NR 7A -, -CO-S-, -S-CO-S-, -S-CO-NR 8A -, -NR 9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR 10A -CS-, -NR 11A It may be substituted by -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO2-. R 1A , R 2A , R 3A , R 4A , R 5A , R 6A, R 7A , R 8A , R 9A , R 10A and R 11A each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0023] R 3 Examples of the heterocyclic group represented by the formula (I) include a pyridyl group, a pyrrolidyl group, a tetrahydrofurfuryl group, a tetrahydrothiophene group, a pyrrole group, a furyl group, a thiopheno group, a piperidine group, a tetrahydropyranyl group, a tetrahydrothiopyranyl group, a thiapyranyl group, an imidazolino group, a pyrazole group, an oxazole group, a thiazolyl group, a dioxanyl group, a morpholino group, a thiazinyl group, a triazole group, a tetrazole group, a dioxolanyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, a purinyl group, a benzotriazolyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, Examples of the heterocyclic group include aliphatic heterocyclic groups having 3 to 16 carbon atoms and aromatic heterocyclic groups having 3 to 16 carbon atoms, such as quinoxalinyl, cinnolinyl, pteridinyl, benzopyranyl, anthryl, acridinyl, xanthenyl, carbazolyl, tetracenyl, porphinyl, chlorinyl, cholinyl, adenyl, guanyl, cytosyl, thyminyl, uracil, quinolyl, thiophenyl, imidazolyl, oxazolyl, and thiazolyl groups, and are preferably pyrrolidyl, piperidyl, tetrahydrofurfuryl, tetrahydropyranyl, tetrahydrothiopheno, tetrahydrothiopyranyl, or pyridyl.

[0024] R 3Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by the formula (I) include a linear or branched alkyl group having 1 to 25 carbon atoms, such as a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, lauryl group, myristyl group, cetyl group, or stearyl group; a cycloalkyl group having 3 to 25 carbon atoms, such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, or cyclohexyl group; or a cycloalkylalkyl group having 4 to 25 carbon atoms, such as a cyclohexylmethyl group. R 3 The aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by the formula (I) is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms. R 3 Examples of the substituent that the aliphatic hydrocarbon group represented by the formula (I) may have include a halogen atom, a hydroxy group, a nitro group, a cyano group, and -SO3H.

[0025] R 3 Each of -CH2- and -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by the following formula is independently -O-, -S-, or -NR 1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR 2A -, -O-CO-NR 3A -, -NR 4A -CO-, -NR 5A -CO-O-, -NR 6A -CO-NR 7A -, -CO-S-, -S-CO-S-, -S-CO-NR 8A -, -NR 9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR 10A -CS-, -NR 11A It may be substituted by -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO2-. When the -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted, it is preferable that the substitution be with -O-, -S-, -CO-O- or -SO2-. When -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -O-, the alkoxy group is preferably represented by -O-R' (R' represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). Alternatively, the alkoxy group may be a polyalkyleneoxy group such as a polyethyleneoxy group or a polypropyleneoxy group. Examples of the alkoxy group represented by -O-R' include a methoxy group, an ethoxy group, an -OCF3 group, a polyethyleneoxy group, and a polypropyleneoxy group. When -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -S-, the alkylthio group is preferably represented by -S-R' (R' represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). Alternatively, the alkylthio group may be a polyalkylenethio group such as a polyethylenethio group or a polypropylenethio group. Examples of the alkylthio group represented by -S-R' include a methylthio group, an ethylthio group, a -SCF3 group, a polyethylenethio group, and a polypropylenethio group. When -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -COO-, the group is preferably represented by -COO-R' (R' represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). When -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -SO2-, the group is preferably represented by -SO2-R' (R' represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom), and may be a -SO2CHF2 group, a -SO2CH2F group, or the like.

[0026] R 1A , R 2A , R 3A 、 R 4A , R 5A , R 6A , R7A , R 8A , R 9A , R 10A and R 11A Examples of the alkyl group having 1 to 6 carbon atoms represented by the formula (I) include linear or branched alkyl groups having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an n-hexyl group, and a 1-methylbutyl group.

[0027] R 3 Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula (I) include aryl groups having 6 to 18 carbon atoms, such as a phenyl group, naphthyl group, anthracenyl group, tetracenyl group, pentacenyl group, phenanthryl group, chrysenyl group, triphenylenyl group, tetraphenyl group, pyrenyl group, perylenyl group, coronenyl group, and biphenyl group; aralkyl groups having 7 to 18 carbon atoms, such as a benzyl group, phenylethyl group, and naphthylmethyl group; and arylalkoxy groups such as a phenoxyethyl group, phenoxydiethylene glycol group, and phenoxypolyalkylene glycol group. An aryl group having 6 to 18 carbon atoms is preferred, and a phenyl group or a benzyl group is more preferred.

[0028] R 3 Examples of the substituent that the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the following formula may have include a halogen atom, a hydroxy group, a thiol group, an amino group, a nitro group, a cyano group, and a -SO3H group.

[0029] R 3 Each of -CH2- and -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the following formula (1) is independently -O-, -S-, or -NR 1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR 2A -, -O-CO-NR 3A -, -NR 4A -CO-, -NR 5A -CO-O-, -NR 6A -CO-NR 7A -, -CO-S-, -S-CO-S-, -S-CO-NR 8A-, -NR 9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR 10A -CS-, -NR 11A It may be substituted by -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO2-. When the -CH2- and / or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferable that it is substituted with -O- or -SO2-. When -CH2- and / or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, the group is preferably an aryloxy group having 6 to 26 carbon atoms, such as a phenoxy group; or an arylalkoxy group such as a phenoxyethyl group, a phenoxydiethylene glycol group, or a phenoxypolyalkylene glycol group. When -CH2- and / or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -SO2-, the aromatic hydrocarbon group is preferably a group represented by -SO2-R" (R" represents an aryl group having 6 to 17 carbon atoms or an aralkyl group having 7 to 17 carbon atoms).

[0030] R 3 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0031] R 3 is a nitro group; a cyano group; a halogen atom; —OCF3; —SCF3; —SF5; —SF3; a fluoroalkyl group (preferably a fluoroalkyl group having 1 to 25 carbon atoms); a fluoroaryl group (preferably a fluoroaryl group having 6 to 18 carbon atoms); 111A or -SO2-R 112A (R 111A and R 112A each independently represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom), and is preferably a cyano group; a fluorine atom; a chlorine atom; —OCF3; —SCF3; a fluoroalkyl group having 1 to 12 carbon atoms; —CO—OR 111A or -SO2-R 112A (R 111Aand R 112A and each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom. ) is more preferred, and a cyano group is even more preferred.

[0032] The molecular weight of compound (X) is preferably 5000 or less, more preferably 3000 or less, and even more preferably 1000 or less. It is also preferably 100 or more, more preferably 200 or more, and even more preferably 300 or more.

[0033] Compound (X) preferably exhibits an absorption maximum at a wavelength of 370 to 420 nm. When compound (X) has an absorption maximum wavelength (λmax) of 370 to 420 nm, it can efficiently absorb ultraviolet to near-ultraviolet light at a wavelength of 380 to 400 nm. The λmax of compound (X) is preferably 375 to 415 nm, more preferably 375 to 410 nm, and even more preferably 380 to 400 nm.

[0034] The compound (X) preferably has a gram absorption coefficient ε at the maximum absorption wavelength (λmax) of 50 or more, more preferably 75 or more, and particularly preferably 100 or more. There is no particular upper limit, but it is generally 100,000 or less. When the gram absorption coefficient ε at λmax of the compound (X) is 50 or more, even a small amount added can efficiently absorb ultraviolet to near-ultraviolet light with a wavelength of 380 nm to 400 nm. The unit of gram absorption coefficient is L / (g·cm). The compound (X) preferably has a ratio ε(λmax) / ε(λmax+30nm) of 5 or more, more preferably 10 or more, and particularly preferably 15 or more. There is no particular upper limit, but it is generally 1000 or less. ε(λmax) represents the gram absorption coefficient at the maximum absorption wavelength of the compound (X), and ε(λmax+30nm) represents the gram absorption coefficient at (maximum absorption wavelength+30nm) of the compound (X). When ε(λmax) / ε(λmax+30 nm) is 5 or more, the side absorption at wavelengths of 420 nm or more can be minimized, and coloring is less likely to occur.

[0035] The compound (X) may have at least one polymerizable group, but preferably has 1 to 4 polymerizable groups. The compound (X) may have at least one partial structure represented by formula (X), but preferably has 1 to 4 partial structures represented by formula (X).

[0036] It is preferable that the compound (X) further has an electron-withdrawing group.

[0037] Compound (X) is preferably any one of compounds represented by formula (I) to (IX), and more preferably a compound represented by formula (I). [ka] [In formulas (I) to (IX), ring W 1 and R 3 has the same meaning as above. Ring W 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 Each independently represents a ring structure having at least one double bond as a ring component. 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W13 may have a substituent. Ring W 111 represents a heterocycle having two nitrogen atoms as its constituent elements. Ring W 112 , Tamaki W 113 and Ring W 114 each independently represents a heterocycle having one nitrogen atom as a constituent element. R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 , R 92 , R 102 and R 112 each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SF5, -SF3, -SO3H, -SO2H, a group containing a polymerizable group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH2- and -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group each independently represent -NR 12A -, -SO2-, -CO-, -O-, -COO-, -OCO-, -CONR 13A -, -NR 14A It may be substituted with -CO-, -S-, -SO-, -SO2-, -CF2- or -CHF-. R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123each independently represent a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SF5, -SF3, -SO3H, -SO2H, a group containing a polymerizable group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH2- and -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group each independently represent -O-, -S-, or -NR 1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR 2A -, -O-CO-NR 3A -, -NR 4A -CO-, -NR 5A -CO-O-, -NR 6A -CO-NR 7A -, -CO-S-, -S-CO-S-, -S-CO-NR 8A -, -NR 9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR 10A -CS-, -NR 11A It may be substituted by -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO2-. R 1A , R 2A , R 3A , R 4A , R 5A , R 6A , R 7A , R 8A , R 9A , R 10A , R 11A , R 12A , R 13A and R 14A each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 , R124 , R 5 , R 15 , R 25 , R 35 , R 75 , R 85 and R 125 each independently represents a group containing an electron-withdrawing group or a polymerizable group. R 1 and R 2 may be bonded to each other to form a ring. R 41 and R 42 may be bonded to each other to form a ring. R 51 and R 52 may be bonded to each other to form a ring. R 61 and R 62 may be bonded to each other to form a ring. R 91 and R 92 may be bonded to each other to form a ring. R 101 and R 102 may be bonded to each other to form a ring. R 111 and R 112 may be bonded to each other to form a ring. R 2 and R 3 may be bonded to each other to form a ring. R 12 and R 13 may be bonded to each other to form a ring. R 42 and R 43 may be bonded to each other to form a ring. R 52 and R 53 may be bonded to each other to form a ring. R 62 and R 63 may be bonded to each other to form a ring. R 72 and R 73 may be bonded to each other to form a ring. R 82 and R 83may be bonded to each other to form a ring. R 92 and R 93 may be bonded to each other to form a ring. R 102 and R 103 may be bonded to each other to form a ring. R 112 and R 113 may be bonded to each other to form a ring. R 4 and R 5 may be bonded to each other to form a ring. R 14 and R 15 may be bonded to each other to form a ring. R 24 and R 25 may be bonded to each other to form a ring. R 34 and R 35 may be bonded to each other to form a ring. R 74 and R 85 may be bonded to each other to form a ring. R 84 and R 85 may be bonded to each other to form a ring. R 124 and R 125 may be bonded to each other to form a ring. R 6 and R 8 each independently represents a divalent linking group. R 7 and R 126 each independently represents a single bond or a divalent linking group. R 9 and R 10 each independently represents a trivalent linking group. R 11 represents a tetravalent linking group. However, in formula (I), R 1 , R 2 , R 4 and R 5 At least one of the groups represents a group containing a polymerizable group. In formula (II), R2 , R 4 , R 5 , R 12 , R 13 , R 14 and R 15 At least one of the groups represents a group containing a polymerizable group. In formula (III), R 4 , R 5 , R 23 , R 24 and R 25 At least one of the groups represents a group containing a polymerizable group. In formula (IV), R 4 , R 5 , R 33 , R 34 and R 35 At least one of the groups represents a group containing a polymerizable group. In formula (V), R 1 , R 2 , R 4 , R 41 , R 42 , R 43 and R 44 At least one of the groups represents a group containing a polymerizable group. In formula (VI), R 1 , R 2 , R 4 , R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 and R 64 At least one of the groups represents a group containing a polymerizable group. In formula (VII), R 2 , R 4 , R 5 , R 72 , R 73 , R 74 , R 75 , R 82 , R 83 , R 84 and R 85 At least one of the groups represents a group containing a polymerizable group. In formula (VIII), R 1 , R 2, R 4 , R 91 , R 92 , R 93 , R 94 , R 101 , R 102 , R 103 , R 104 , R 111 , R 112 , R 113 and R 114 At least one of the groups represents a group containing a polymerizable group. In formula (IX), R 2 , R 4 , R 5 , R 123 , R 124 and R 125 At least one of the groups represents a group containing a polymerizable group.]

[0038] Ring W 2 , Tamaki W 3 , Tamaki W 4 , Tamaki W 5 , Tamaki W 6 , Tamaki W 7 , Tamaki W 8 , Tamaki W 9 , Tamaki W 10 , Tamaki W 11 , Tamaki W 12 and Ring W 13 are not particularly limited as long as they each independently have one or more double bonds as ring components. 2 ~Tamaki W 13 Each of the rings W may be a single ring or a condensed ring. 2 ~Tamaki W 13 may be a ring that does not have aromaticity (aliphatic ring) or may be an aromatic ring. Ring W 1 ~Tamaki W 13 may be a heterocycle containing a heteroatom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a ring component.

[0039] Ring W 2 ~Tamaki W 13 each independently has one or more double bonds as a constituent element of the ring, but ring W 1The number of double bonds contained in the formula is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0040] Ring W 2 ~Tamaki W 13 are usually each independently a ring having 5 to 18 carbon atoms, preferably a 5- to 7-membered ring structure, and more preferably a 6-membered ring structure. Ring W 2 ~Tamaki W 13 Preferably, each of the rings W is independently a monocyclic ring. 2 ~Tamaki W 13 are preferably each independently a ring that does not have aromaticity. Ring W 2 ~Tamaki W 13 may each independently have a substituent. 1 The substituents are the same as those that may be contained in the group.

[0041] Ring W 2 ~Tamaki W 13 The substituents which may be possessed by each of the groups are preferably an amino group which may be substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.

[0042] Ring W 2 ~Tamaki W 13 A specific example of this is the ring W 1 The same specific examples as above can be cited.

[0043] Ring W 111 is a heterocycle containing two nitrogen atoms as ring members. Ring W 111 may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring. Ring W 111 is usually a 5- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring. Ring W 111 The ring W may have a substituent.111 Examples of the substituents that may be possessed by the group include a hydroxy group, a thiol group, an aldehyde group, an alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group, an alkoxy group having 1 to 6 carbon atoms such as a methoxy group or an ethoxy group, an alkylthio group having 1 to 6 carbon atoms such as a methylthio group or an ethylthio group, an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms such as an amino group, a methylamino group, a dimethylamino group or a methylethyl group, and -CONR 1f R 2f (R 1f and R 2f each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; 3f (R 3f represents alkyl having 1 to 6 carbon atoms; )-CSSR 4f (R 4f represents alkyl having 1 to 6 carbon atoms; );-CSOR 5f (R 5f represents alkyl having 1 to 6 carbon atoms; -SO2R 6f (R 6f represents an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms which may have a fluorine atom).

[0044] Ring W 111 Examples of the ring include the rings shown below. [ka]

[0045] Ring W 112 , Tamaki W 113 and Ring W 114 are each independently a heterocycle containing one nitrogen atom as a ring component. 112 , Tamaki W 113 and Ring W 114 may each independently be a monocyclic ring or a fused ring, but is preferably a monocyclic ring. Ring W 112 , Tamaki W 113 and Ring W 114are each independently usually a 5- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring. Ring W 112 , Tamaki W 113 and Ring W 114 Each of the rings W may independently have a substituent. 112 , Tamaki W 113 and Ring W 114 The substituents which may be present on the ring W include 1 The substituents are the same as those of the above.

[0046] Ring W 112 , Tamaki W 113 and Ring W 114 Examples of the ring include the rings shown below. [ka]

[0047] R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 , R 124 , R 5 , R 15 , R 35 , R 75 , R 85 and R 125 Examples of the electron-withdrawing groups represented by the formula (X-1) include, independently, a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -SO2CF3, -SO2CHF2, -SO2CH2F, and a group represented by formula (X-1). [ka] [In formula (X-1), R 222represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. X 1 are -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO2-, and -NR 223 CO- or -CONR 224 - represents. R 223 and R 224 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * represents a bond.]

[0048] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of halogenated alkyl groups include fluoroalkyl groups such as trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, and perfluorohexyl, with perfluoroalkyl groups being preferred. The halogenated alkyl group typically has 1 to 25 carbon atoms, and preferably 1 to 12 carbon atoms. The halogenated alkyl group may be linear or branched. Examples of the halogenated aryl group include a fluorophenyl group, a chlorophenyl group, and a bromophenyl group, and the halogenated aryl group is preferably a fluoroaryl group, and more preferably a perfluoroaryl group. The halogenated aryl group usually has 6 to 18 carbon atoms, and preferably has 6 to 12 carbon atoms.

[0049] X 1 is preferably —COO— or —SO 2 —. R 222Examples of the alkyl group having 1 to 25 carbon atoms represented by the formula (R) include a linear or branched alkyl group having 1 to 25 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an n-hexyl group, a 1-methylbutyl group, a 3-methylbutyl group, an n-octyl group, an n-decyl group, and a 2-hexyl-octyl group. 222 is preferably an alkyl group having 1 to 12 carbon atoms. R 222 Examples of the substituent that the alkyl group having 1 to 25 carbon atoms represented by the following formula may have include a halogen atom and a hydroxy group. R 222 Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula (I) include aryl groups having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group, and a biphenyl group; and aralkyl groups having 7 to 18 carbon atoms such as a benzyl group, a phenylethyl group, and a naphthylmethyl group. R 222 Examples of the substituent that the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the following formula may have include a halogen atom and a hydroxy group. R 223 and R 224 Examples of the alkyl group having 1 to 6 carbon atoms represented by the formula (I) include a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an n-hexyl group, and a 1-methylbutyl group.

[0050] R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 , R 124 , R 5 , R 15 , R 35 , R 75 , R 85and R 125 The electron-withdrawing groups represented by the formula (I) each independently include a nitro group, a cyano group, a halogen atom, -OCF3, -SCF3, -SF5, -SF3, a fluoroalkyl group (preferably a fluoroalkyl group having 1 to 25 carbon atoms), a fluoroaryl group (preferably a fluoroaryl group having 6 to 18 carbon atoms), -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), and is preferably a nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF3, -SCF3, a fluoroalkyl group, -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have one or more halogen atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have one or more halogen atoms.

[0051] R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 , R 124 , R 5 , R 15 , R 35 , R 75 , R 85 and R 125 Examples of the group containing a polymerizable group represented by the formula (I-1) include a group represented by the formula (I-2) above.

[0052] R 4 and R 5 may be bonded to each other to form a ring. 4 and R 5 The ring formed by bonding together may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring. 4 and R 5 The ring formed by bonding together may contain a heteroatom (nitrogen atom, oxygen atom, sulfur atom) or the like as a ring component. R 4 and R 5 The ring formed by bonding together is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring. R 4 and R 5 Examples of the ring formed by bonding together include the structures shown below. [ka] [In the formula, * represents a bond to a carbon atom. 1E ~R 16E represents a hydrogen atom or a substituent.]

[0053] R 4 and R 5 The ring formed by bonding together is a substituent (R 1E ~R 16E The substituent may have, for example, a ring W 1 The substituents that may be contained in the R 1E ~R 16E are each independently preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group.

[0054] R 14 and R 15 The ring formed by bonding together is R 4 and R 5 are the same as the ring formed by bonding together. R24 and R 25 The ring formed by bonding together is R 4 and R 5 are the same as the ring formed by bonding together. R 34 and R 35 The ring formed by bonding together is R 4 and R 5 are the same as the ring formed by bonding together. R 74 and R 75 The ring formed by bonding together is R 4 and R 5 are the same as the ring formed by bonding together. R 84 and R 85 The ring formed by bonding together is R 4 and R 5 are the same as the ring formed by bonding together. R 124 and R 125 The ring formed by bonding together is R 4 and R 5 are the same as the ring formed by bonding together.

[0055] R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 、 R 92 , R 102 , R 112 , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R103 , R 113 and R 123 As the heterocyclic group represented by R 3 and preferably a pyrrolidyl group, a piperidyl group, a tetrahydrofurfuryl group, a tetrahydropyranyl group, a tetrahydrothiopheno group, a tetrahydrothiopyranyl group, or a pyridyl group.

[0056] R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 、 R 92 , R 102 , R 112 , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 As the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R 3 Examples of the aliphatic hydrocarbon group include the same aliphatic hydrocarbon groups having 1 to 25 carbon atoms as those represented by the following formula: The aliphatic hydrocarbon group having 1 to 25 carbon atoms is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms.

[0057] R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42, R 52 , R 62 , R 72 , R 82 、 R 92 , R 102 , R 112 , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 Examples of the substituent that the aliphatic hydrocarbon group represented by the formula (I) may have include a halogen atom, a hydroxy group, a nitro group, a cyano group, and -SO3H.

[0058] Also, R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 、 R 92 , R 102 , R 112 , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 Each of -CH2- and -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by the formula: 12A -, -SO2-, -CO-, -O-, -COO-, -OCO-, -CONR 13A -, -NR 14AIt may be substituted with -CO-, -S-, -SO-, -SO2-, -CF2- or -CHF-. When the -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted, it is preferable that the substitution be with -O-, -S-, -CO-O- or -SO2-. When -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -O-, the alkoxy group is preferably represented by -O-R' (R' is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). Alternatively, the alkoxy group may be a polyalkyleneoxy group such as a polyethyleneoxy group or a polypropyleneoxy group. Examples of the alkoxy group represented by -O-R' include a methoxy group, an ethoxy group, an -OCF3 group, a polyethyleneoxy group, and a polypropyleneoxy group. When -CH2- and / or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -S-, the alkylthio group is preferably represented by -S-R' (R' is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). Alternatively, the alkylthio group may be a polyalkylenethio group such as a polyethylenethio group or a polypropylenethio group. Examples of the alkylthio group represented by -S-R' include a methylthio group, an ethylthio group, a -SCF3 group, a polyethylenethio group, and a polypropylenethio group. When —CH— and / or —CH═ contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with —COO—, —COO-R′(R ’ is preferably a group represented by an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). When —CH— and / or —CH═ contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with —SO—, —SO—R′(R ’ is preferably a group represented by an alkyl group having 1 to 24 carbon atoms which may have a halogen atom), and may be a -SO2CHF2 group, a -SO2CH2F group, or the like.

[0059] R 12A , R 13A and R 14AAs an alkyl group having 1 to 6 carbon atoms represented by the formula: 1A Examples include the same alkyl groups having 1 to 6 carbon atoms as those represented by the following formula:

[0060] R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 、 R 92 , R 102 , R 112 , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 As the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R 3 The aromatic hydrocarbon group may be the same as the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the following formula: and is preferably an aryl group having 6 to 18 carbon atoms, more preferably a phenyl group or a benzyl group. Examples of the substituent that the aromatic hydrocarbon group having 6 to 18 carbon atoms may have include a halogen atom, a hydroxy group, a thiol group, an amino group, a nitro group, a cyano group, and a -SO3H group. Each of -CH2- and -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms independently represents -NR 12A -, -SO2-, -CO-, -O-, -COO-, -OCO-, -CONR 13A -, -NR 14A It may be substituted with -CO-, -S-, -SO-, -SO2-, -CF2- or -CHF-. When the -CH2- and / or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferable that it is substituted with -O- or -SO2-. When -CH2- and / or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, the group is preferably an aryloxy group having 6 to 26 carbon atoms, such as a phenoxy group; or an arylalkoxy group such as a phenoxyethyl group, a phenoxydiethylene glycol group, or a phenoxypolyalkylene glycol group. When -CH2- and / or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -SO2-, the aromatic hydrocarbon group is preferably a group represented by -SO2-R" (R" represents an aryl group having 6 to 17 carbon atoms or an aralkyl group having 7 to 17 carbon atoms).

[0061] R 1 , R 41 , R 51 , R 61 , R 91 , R 101 , R 111 , R 2 , R 12 , R 42 , R 52 , R 62 , R 72 , R 82 、 R 92 , R 102 , R 112 , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 Examples of the group containing a polymerizable group represented by the formula (I-1) include a group represented by the formula (I-2) above.

[0062] R 2 and R 3 may be linked to each other to form a ring. 2 and R3 As a component of the ring formed by connecting 1 That is, R 2 and R 3 and ring W 1 R forms a condensed ring. 2 and R 3 and ring W 1 Specific examples of the fused ring formed by the above include the ring structures shown below. [ka]

[0063] R 12 and R 13 The ring formed by bonding together is R 12 and R 13 As a component of the ring formed by connecting 2 That is, R 12 and R 13 The rings formed by bonding together and the ring W 2 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 42 and R 43 The ring formed by bonding together is R 42 and R 43 As a component of the ring formed by connecting 5 That is, R 42 and R 43 The rings formed by bonding together and the ring W 5 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 52 and R 53 The ring formed by bonding together is R 52 and R 53As a component of the ring formed by connecting 6 That is, R 52 and R 53 The rings formed by bonding together and the ring W 6 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 62 and R 63 The ring formed by bonding together is R 62 and R 63 As a component of the ring formed by connecting 7 That is, R 62 and R 63 The rings formed by bonding together and the ring W 7 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 72 and R 73 The ring formed by bonding together is R 72 and R 73 As a component of the ring formed by connecting 8 That is, R 72 and R 73 The rings formed by bonding together and the ring W 8 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 82 and R 83 The ring formed by bonding together is R 82 and R 83 As a component of the ring formed by connecting 9 That is, R 82 and R 83 The rings formed by bonding together and the ring W 9Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 92 and R 93 The ring formed by bonding together is R 92 and R 93 As a component of the ring formed by connecting 12 That is, R 92 and R 93 The rings formed by bonding together and the ring W 12 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 102 and R 103 The ring formed by bonding together is R 102 and R 103 As a component of the ring formed by connecting 10 That is, R 102 and R 103 The rings formed by bonding together and the ring W 10 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by R 112 and R 113 The ring formed by bonding together is R 112 and R 113 As a component of the ring formed by connecting 11 That is, R 112 and R 113 The rings formed by bonding together and the ring W 11 Specifically, R 2 and R 3 and ring W 1 and the fused ring formed by

[0064] R 1 and R 2 may be bonded to each other to form a ring. 1 and R 2 The ring formed by bonding together is a heterocyclic ring containing one nitrogen atom as a ring component. 1 and R 2 The ring formed by bonding together may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring. 1 and R 2 The ring formed by bonding together may further contain a heteroatom (oxygen atom, sulfur atom, nitrogen atom, etc.) as a ring component. 1 and R 2 The ring formed by bonding together is preferably a heterocycle having no aromaticity (aliphatic heterocycle), and more preferably an aliphatic heterocycle having no unsaturated bond. R 1 and R 2 The ring formed by bonding together is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring. R 1 and R 2 The ring formed by bonding together may have a substituent. For example, the ring W 2 ~Tamaki W 12 The substituents are the same as those that may be contained in the group. R 1 and R 2 Examples of the ring formed by bonding together include the rings shown below. [ka]

[0065] R 41 and R 42 The ring formed by bonding together is R 1 and R 2 are the same as the ring formed by bonding together. R 51 and R 52 The ring formed by bonding together is R 1and R 2 are the same as the ring formed by bonding together. R 61 and R 62 The ring formed by bonding together is R 1 and R 2 are the same as the ring formed by bonding together. R 91 and R 92 The ring formed by bonding together is R 1 and R 2 are the same as the ring formed by bonding together. R 101 and R 102 The ring formed by bonding together is R 1 and R 2 are the same as the ring formed by bonding together. R 111 and R 112 The ring formed by bonding together is R 1 and R 2 are the same as the ring formed by bonding together.

[0066] R 6 , R 7 , R 8 and R 126 Examples of the divalent linking group represented by the formula (I) include a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. The -CH2- contained in the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group may be -O-, -S-, -NR 1B -(R 1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) may be substituted with -CO-, -SO2-, -SO-, or -PO3-. Furthermore, examples of the substituent that the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group may have include a halogen atom, a hydroxy group, a carboxy group, and an amino group.

[0067] R 6 , R 7 , R 8 and R126 Each of the divalent linking groups represented by the following formula (I) is preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and more preferably a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent.

[0068] R 6 , R 7 , R 8 and R 126 Specific examples of the divalent linking group represented by the formula include the linking groups shown below: In the formula, * represents a bond. [ka]

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] R 6 , R 7 and R 126are each preferably an optionally substituted divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms or a linking group represented by the following formula, and more preferably an optionally substituted divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms or a linking group represented by the following formula: [ka]

[0076] R 8 is preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a linking group represented by the following formula: [ka]

[0077] R 9 and R 10 Examples of the trivalent linking group represented by the formula (I) include, independently, a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or a trivalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. The -CH2- contained in the trivalent aliphatic hydrocarbon group can be -O-, -S-, -CS-, -CO-, -SO-, -NR 11B (R 11B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Examples of the substituent that the trivalent aliphatic hydrocarbon group and the trivalent aromatic hydrocarbon group may have include a halogen atom, a hydroxy group, a carboxy group, and an amino group. R 9 and R 10 Preferably, the trivalent linking groups represented by the following formula are each independently a trivalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. R 9 and R 10 Specific examples of the trivalent linking group represented by the formula include the linking groups shown below. [ka]

[0078] R 11 Examples of the tetravalent linking group represented by the formula (I) include a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and a tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. The -CH2- contained in the tetravalent aliphatic hydrocarbon group can be -O-, -S-, -CS-, -CO-, -SO-, -NR 11C -(R 11C represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Examples of the substituent that the tetravalent aliphatic hydrocarbon group and the tetravalent aromatic hydrocarbon group may have include a halogen atom, a hydroxy group, a carboxy group, and an amino group. The tetravalent linking groups represented by R11 are preferably each independently a tetravalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. R 11 Specific examples of the tetravalent linking group represented by the formula: include the linking groups shown below. [ka]

[0079] In the compound of formula (I), R 1 , R 2 , R 4 and R 5 At least one of R is a group containing a polymerizable group. 1 , R 2 , R 4 and R 5 When two groups selected from form a ring (for example, R 1 and R 2 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 1 , R 2 , R 4 and R 5 It is considered that at least one of the groups contains a polymerizable group.

[0080] In the compound of formula (II), R2 , R 4 , R 5 , R 12 , R 13 , R 14 and R 15 At least one of R is a group containing a polymerizable group. 2 , R 4 , R 5 , R 12 , R 13 , R 14 and R 15 When two groups selected from form a ring (for example, R 14 and R 15 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 2 , R 4 , R 5 , R 12 , R 13 , R 14 and R 15 It is considered that at least one of the groups contains a polymerizable group.

[0081] In the compound of formula (III), R 4 , R 5 , R 23 , R 24 and R 25 At least one of R is a group containing a polymerizable group. 4 , R 5 , R 23 , R 24 and R 25 When two groups selected from form a ring (for example, R 4 and R 5 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 4 , R 5 , R 23 , R 24 and R 25 It is considered that at least one of the groups contains a polymerizable group.

[0082] In the compound of formula (IV), R 4 , R 5 , R 33 , R 34 and R35 At least one of R is a group containing a polymerizable group. 4 , R 5 , R 33 , R 34 and R 35 When two groups selected from form a ring (for example, R 34 and R 35 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 4 , R 5 , R 33 , R 34 and R 35 It is considered that at least one of the groups contains a polymerizable group.

[0083] In the compound of formula (V), R 1 , R 2 , R 4 , R 41 , R 42 , R 43 and R 44 At least one of R is a group containing a polymerizable group. 1 , R 2 , R 4 , R 41 , R 42 , R 43 and R 44 When two groups selected from form a ring (for example, R 1 and R 2 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 1 , R 2 , R 4 , R 41 , R 42 , R 43 and R 44 It is considered that at least one of the groups contains a polymerizable group.

[0084] In the compound of formula (VI), R 1 , R 2 , R 4 , R 51 , R 52 , R 53 , R 54 , R 61 , R62 , R 63 and R 64 At least one of R is a group containing a polymerizable group. 1 , R 2 , R 4 , R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 and R 64 When two groups selected from form a ring (for example, R 1 and R 2 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 1 , R 2 , R 4 , R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 and R 64 It is considered that at least one of the groups contains a polymerizable group.

[0085] In the compound of formula (VII), R 2 , R 4 , R 5 , R 72 , R 73 , R 74 , R 75 , R 82 , R 83 , R 84 and R 85 At least one of R is a group containing a polymerizable group. 2 , R 4 , R 5 , R 72 , R 73 , R 74 , R 75 , R 82 , R 83 , R 84 and R 85 When two groups selected from form a ring (for example, R 4 and R 5are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 2 , R 4 , R 5 , R 72 , R 73 , R 74 , R 75 , R 82 , R 83 , R 84 and R 85 It is considered that at least one of the groups contains a polymerizable group.

[0086] In the compound of formula (VIII), R 1 , R 2 , R 4 , R 91 , R 92 , R 93 , R 94 , R 101 , R 102 , R 103 , R 104 , R 111 , R 112 , R 113 and R 114 At least one of R is a group containing a polymerizable group. 1 , R 2 , R 4 , R 91 , R 92 , R 93 , R 94 , R 101 , R 102 , R 103 , R 104 , R 111 , R 112 , R 113 and R 114 When two groups selected from form a ring (for example, R 1 and R 2 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 1 , R 2 , R 4 , R 91 , R 92 , R 93 , R 94 , R 101 , R 102 , R 103, R 104 , R 111 , R 112 , R 113 and R 114 It is considered that at least one of the groups contains a polymerizable group.

[0087] In the compound of formula (IX), R 2 , R 4 , R 5 , R 124 and R 125 At least one of R is a group containing a polymerizable group. 2 , R 4 , R 5 , R 124 and R 125 When two groups selected from form a ring (for example, R 4 and R 5 are bonded to each other to form a ring), if the formed ring has a polymerizable group, R 2 , R 4 , R 5 , R 124 and R 125 At least one of the groups is considered to contain a polymerizable group.

[0088] R 1 is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 10 carbon atoms. R 2 is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 10 carbon atoms. R 1 and R 2 are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure. R 3 is a nitro group, a cyano group, a halogen atom, -OCF3, -SCF3, -SF5, -SF3, a fluoroalkyl group (preferably a fluoroalkyl group having 1 to 25 carbon atoms), a fluoroaryl group (preferably a fluoroaryl group having 6 to 18 carbon atoms), -CO-OR111A or -SO2-R 112A (R 111A and R 112A each independently represents an alkyl group having 1 to 24 carbon atoms.) is preferably a cyano group, a fluorine atom, a chlorine atom, —OCF3, —SCF3, a fluoroalkyl group, —CO—OR 111A or -SO2-R 112A (R 111A and R 112A each independently represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.) is more preferred, a cyano group or a fluorine atom is even more preferred, and a cyano group is particularly preferred. R 4 and R 5 are each independently a nitro group, a cyano group, a halogen atom, -OCF3, -SCF3, -SF5, -SF3, a fluoroalkyl group, a fluoroaryl group, or -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), and is preferably a nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF3, -SCF3, a fluoroalkyl group, -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.) is more preferred, and a cyano group is particularly preferred. R 4 and R 5 It is preferable that at least one of the groups is a cyano group. R 4is a cyano group, and R 5 is a cyano group, -CO-OR 222 or -SO2-R 222 (R 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent.

[0089] R 4 and R 5 Preferably, the groups have the same structure. R 4 and R 5 and are preferably both cyano groups.

[0090] R 41 , R 51 , R 61 , R 91 , R 101 and R 111 are each independently preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. R 12 , R 42 , R 52 , R 62 , R 72 , R 82 , R 92 , R 102 and R 112 are each independently preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. R 41 and R 42 are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure. R 51 and R 52are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure. R 61 and R 62 are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure. R 91 and R 92 are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure. R 101 and R 102 are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure. R 111 and R 112 are preferably linked to each other to form a ring, more preferably to form an aliphatic heterocycle, further preferably to be an aliphatic heterocycle having no unsaturated bond, and particularly preferably to have a pyrrolidine ring or piperidine ring structure.

[0091] R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123are each independently a nitro group; a cyano group; a halogen atom; -OCF3; -SCF3; -SF5; -SF3; a fluoroalkyl group having 1 to 25 carbon atoms; a fluoroaryl group having 6 to 18 carbon atoms; or -CO-OR 111A or -SO2-R 112A (R 111A and R 112A each independently represents an alkyl group having 1 to 24 carbon atoms which may have a halogen atom), and is preferably a cyano group; a fluorine atom; a chlorine atom; —OCF3; —SCF3; a fluoroalkyl group having 1 to 12 carbon atoms; —CO—OR 111A or -SO2-R 112A (R 111A and R 112A and each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom. ) is more preferred, and a cyano group is particularly preferred.

[0092] R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 , R 124 , R 15 , R 35 , R 75 , R 85 and R 125 are each independently a nitro group, a cyano group, a halogen atom, -OCF3, -SCF3, -SF5, -SF3, or -CO-OR 222 , -SO2-R 222 , a fluoroalkyl group (preferably a fluoroalkyl group having 1 to 25 carbon atoms) or a fluoroaryl group (preferably a fluoroaryl group having 6 to 18 carbon atoms), and a nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF3, -SCF3, a fluoroalkyl group, -CO-OR 222 or -SO2-R 222 (R 222represents an alkyl group having 1 to 25 carbon atoms which may have a halogen atom.) is more preferred, and a cyano group, —CO—OR 222 or -SO2-R 222 (R 222 represents an alkyl group having 1 to 25 carbon atoms which may have one or more halogen atoms.) is more preferred, and a cyano group is particularly preferred.

[0093] R 14 and R 15 It is preferable that the structure is the same as that of the R 24 and R 25 It is preferable that the structure is the same as that of the R 34 and R 35 It is preferable that the structure is the same as that of the R 74 and R 75 It is preferable that the structure is the same as that of the R 84 and R 85 It is preferable that the structure is the same as that of the R 124 and R 125 It is preferable that the structure is the same as that of the

[0094] R 1 and R 2 Preferably, at least one selected from the group consisting of R 1 and R 2 are linked together to form a ring, and R 1 and R 2 It is more preferable that the rings which are linked to each other have a polymerizable group.

[0095] Compound (I) is more preferably any of a compound represented by formula (I-1A), a compound represented by formula (I-2A), and a compound represented by formula (I-3A). [ka] [In the formula, R 1 , R 2 , R3 , R 4 , R 5 has the same meaning as above. Rx1, Rx2, Rx3, Rx4, Rx5, Rx6, Rx7, and Rx8 each independently represent a hydrogen atom or a substituent. m1 represents an integer of 0 to 4, and m2 represents an integer of 0 to 5. In formula (I-1A), R 1 , R 2 , R 3 , R 4 , R 5 At least one of Rx1 and Rx2 represents a group containing a polymerizable group. In formula (I-2A), R 4 , R 5 At least one of Rx3, Rx4 and Rx5 represents a group containing a polymerizable group. In formula (I-3A), R 4 , R 5 At least one of Rx6, Rx7, and Rx8 represents a group containing a polymerizable group.]

[0096] The substituents represented by Rx1 to Rx8 include ring W 1 The substituents are the same as those that may be contained in the group. It is preferable that Rx1, Rx2, Rx3, Rx4, Rx6, and Rx7 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. When m1 is an integer of 2 or more, multiple R x5 may be the same group or different groups. When m2 represents an integer of 2 or more, multiple R x8 may be the same group or different groups. It is preferable that Rx5 and Rx8 each independently represent a group containing a polymerizable group.

[0097] Examples of the compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) include the compounds shown below: In the following formula, Me represents a methyl group, and Et represents an ethyl group. [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] Examples of the compound represented by formula (II) (hereinafter sometimes referred to as compound (II)) include the compounds described below. [ka]

[0105] [ka]

[0106] Examples of the compound represented by formula (III) (hereinafter, sometimes referred to as compound (III)) include the compounds described below. [ka]

[0107] Examples of the compound represented by formula (IV) (hereinafter, sometimes referred to as compound (IV)) include the compounds described below. [ka]

[0108] Examples of the compound represented by formula (V) (hereinafter sometimes referred to as compound (V)) include the compounds shown below, where Me represents a methyl group. [ka]

[0109] [ka]

[0110] [ka]

[0111] [ka]

[0112] [ka]

[0113] Examples of the compound represented by formula (VI) (hereinafter sometimes referred to as compound (VI)) include the compounds described below. [ka]

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] Examples of the compound represented by formula (VII) (hereinafter, sometimes referred to as compound (VII)) include the compounds described below. [ka]

[0119] [ka]

[0120] [ka]

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] Examples of the compound represented by formula (VIII) (hereinafter, sometimes referred to as compound (VIII)) include the compounds described below. [ka]

[0126] [ka]

[0127] [ka]

[0128] [ka]

[0129] [ka]

[0130] Examples of the compound represented by formula (IX) (hereinafter sometimes referred to as compound (IX)) include the compounds shown below. [ka]

[0131] <Method for producing compound (I)> The method for producing compound (I) will be described. For example, R 1 Compound (I) having a (meth)acryloyloxy group (hereinafter, sometimes referred to as compound (I-1B)) can be obtained by reacting a compound represented by formula (MA) (hereinafter, sometimes referred to as compound (MA)) with a compound represented by formula (MB) (hereinafter, sometimes referred to as compound (MB)). [ka] [In the formula, ring W 1 and R 3 has the same meaning as above. R 2 , R 4 and R 5 has the same meaning as above, except that it does not represent a group containing a polymerizable group. R E1 represents a divalent linking group, and R E2 represents a (meth)acryloyl group, and X represents a halogen atom.

[0132] Also, R 1 and R 2 and R are linked to each other to form a ring, 1 and R 2 Compound (I) in which the rings in which the groups are linked together have a (meth)acryloyloxy group (hereinafter, sometimes referred to as compound (I-1C)) can be obtained by reacting a compound represented by formula (M-A1) (hereinafter, sometimes referred to as compound (M-A1)) with compound (MB). [ka] [In the formula, ring W 1 and R 3 has the same meaning as above. R 4 and R 5 has the same meaning as above, except that it does not represent a group containing a polymerizable group. R E2 represents a (meth)acryloyl group, and R E3 represents a single bond or a divalent linking group, and X represents a halogen atom. Ring W1 represents a heterocycle containing a nitrogen atom as a ring component.

[0133] The reaction of compound (MA) or compound (M-A1) with compound (MB) is carried out by mixing compound (MA) or compound (M-A1) with compound (MB). Preferably, the mixing of compound (MA) or compound (M-A1) with compound (MB) is carried out by adding compound (MB) to compound (MA) or compound (M-A1).

[0134] The reaction of compound (MA) or compound (M-A1) with compound (MB) is preferably carried out in the presence of a base. Examples of the base include amine compounds (preferably tertiary amines such as triethylamine and diisopropylethylamine) such as ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidine, piperidine, diazabicycloundecene, diazabicyclononene, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, dimethoxyaniline, ammonium acetate, and β-alanine, potassium hydroxide, sodium hydroxide, lithium hydroxide, sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium carbonate, and potassium carbonate. The amount of the base used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (MA).

[0135] The reaction of compound (MA) or compound (M-A1) with compound (MB) is preferably carried out in the presence of a solvent, such as chloroform, acetonitrile, benzene, toluene, acetone, ethyl acetate, dichloromethane, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, dibutylhydroxytoluene, water, n-hexane, or n-heptane.

[0136] The reaction time of compound (MA) or compound (M-A1) with compound (MB) is usually 0.1 to 100 hours, preferably 1 to 30 hours. The reaction temperature of the compound (MA) or the compound (M-A1) with the compound (MB) is usually from -80 to +150°C, and preferably from -30 to 130°C. The amount of compound (MB) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (MA) or compound (M-A1).

[0137] Examples of the compound (MB) include acrylic acid chloride, which is commercially available. Examples of the compound (MA) include the compounds shown below. [ka] Examples of the compound (M-A1) include the compounds shown below. [ka]

[0138] Compound (MA) can be obtained by reacting a compound represented by formula (MC) (hereinafter sometimes referred to as compound (MC)) with a compound represented by formula (MD) (hereinafter sometimes referred to as compound (MD)). The compound (M-A1) can be obtained by reacting the compound (MC) with a compound represented by the formula (ME) (hereinafter, sometimes referred to as the compound (ME)). [ka] [In the formula, R E1 , R E3 , R 3 , and ring W1 have the same meaning as above. R 2 , R 4 and R 5has the same meaning as above, except that it does not represent a group containing a polymerizable group. Ring W 1A represents a ring structure.

[0139] The reaction of compound (MC) with compound (MD) or compound (ME) is usually carried out by mixing compound (MC) with compound (MD) or compound (ME), and it is preferable to add compound (MD) or compound (ME) to compound (MC). The reaction of compound (MC) with compound (MD) or compound (ME) is preferably carried out by mixing compound (MC) with compound (MD) or compound (ME) in the presence of a base and a methylating agent. It is more preferable to mix compound (MC), compound (MD) or compound (ME), a base, and a methylating agent, and it is even more preferable to mix compound (MD) or compound (ME) with a mixture of compound (MC), a methylating agent, and a base.

[0140] Examples of the base include the same bases as those used in the reaction of compound (MA) or compound (M-A1) with compound (MB). The amount of the base used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (MC).

[0141] Examples of the methylating agent include iodomethane, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl paratoluenesulfonate, methyl trifluoromethanesulfonate, and trimethyloxonium tetrafluoroborate. The amount of the methylating agent used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (MC). The amount of compound (MD) or compound (ME) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (MC). The reaction of compound (MC) with compound (MD) or compound (ME) may be carried out in the presence of a solvent, such as methanol, ethanol, isopropanol, toluene, or acetonitrile.

[0142] The reaction time of compound (MC) with compound (MD) or compound (ME) is usually 0.1 to 100 hours. The reaction temperature of the compound (MC) with the compound (MD) or the compound (ME) is usually -80 to +150°C.

[0143] Examples of the compound (MD) include (2-hydroxy)ethylmethylamine, (4-hydroxy)butylamine, 4-hydroxybutylmethylamine, and 4-hydroxybutylbutylamine. Examples of compound (ME) include 3-hydroxypyrrolidine, 3-hydroxymethylpyrrolidine, 4-hydroxypiperidine, 3-hydroxypiperidine, 3-hydroxymethylpiperidine, 4-(hydroxymethyl)piperidine, etc. When compound (ME) is used, the hydroxy group contained in compound (ME) may be protected with a silyl group or the like.

[0144] Examples of the compound (MC) include the compounds shown below. [ka]

[0145] Compound (MC) can be obtained by reacting a compound represented by formula (MF) (hereinafter, sometimes referred to as compound (MF)) with a compound represented by formula (MG) (hereinafter, sometimes referred to as compound (MG)). [ka] [In the formula, ring W 1A and R 3 has the same meaning as above. R 4 and R5 has the same meaning as above, except that it does not represent a group containing a polymerizable group. E1 represents a leaving group.

[0146] Examples of the leaving group represented by E1 include a halogen atom, a p-toluenesulfonyl group, and a trifluoromethylsulfonyl group.

[0147] The reaction between compound (MF) and compound (MG) can be carried out by mixing compound (MF) and compound (MG). The reaction of compound (MF) with compound (MG) is preferably carried out in the presence of a base. Examples of the base include the same bases as those used in the reaction of compound (MA) or compound (M-A1) with compound (MB). Preferred bases include potassium carbonate, potassium hydroxide, potassium tert-butoxide, and diisopropylethylamine. The amount of the base used is usually 0.1 to 10 mol, and preferably 0.5 to 5 mol, per 1 mol of compound (MF). The reaction between compound (MF) and compound (MG) may be carried out in the presence of a solvent, such as toluene, acetonitrile, methanol, ethanol, or isopropanol. The reaction time between compound (MF) and compound (MG) is usually 0.1 to 100 hours. The reaction temperature between compound (MF) and compound (MG) is usually -80 to +150°C.

[0148] As the compound (MG), commercially available products may be used. Examples thereof include cyanogen chlorate, cyanogen bromide, paratoluenesulfonyl cyanide, trifluoromethanesulfonyl cyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate (also known as SelectFloor (registered trademark of Air Products and Chemicals)), benzoyl(phenyliodonio)(trifluoromethanesulfonyl)methanide, 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate, N-bromosuccinimide, N-chlorosuccinimide, and N-iodosuccinimide.

[0149] Examples of the compound (MF) include the compounds shown below. [ka]

[0150] Compound (MF) can be obtained by reacting compound (MH) with compound (MI). The reaction of compound (MH) with compound (MI) can be carried out by mixing compound (MH) with compound (MI). [ka] [In the formula, ring W 1A has the same meaning as above. R 4 and R 5 has the same meaning as above, except that it does not represent a group containing a polymerizable group.

[0151] The reaction of compound (MH) with compound (MI) is preferably carried out in the presence of a base. Examples of the base include the same bases as those used in the reaction of compound (MA) or compound (M-A1) with compound (MB). The amount of the base used is usually 0.1 to 5 moles, preferably 0.5 to 2 moles, per mole of compound (MH). The reaction of compound (MH) with compound (MI) may be carried out in the presence of a solvent. Examples of the solvent include methanol, ethanol, isopropanol, toluene, and acetonitrile. The reaction time between compound (MH) and compound (MI) is usually 0.1 to 10 hours. The reaction temperature between compound (MH) and compound (MI) is usually -50 to 150°C. The amount of compound (MI) used is usually 0.1 to 10 mol, preferably 0.5 to 2 mol, per 1 mol of compound (MH).

[0152] As the compound (MI), commercially available products may be used, for example, malononitrile. Examples of the compound (MH) include the compounds described below, and are commercially available. [ka]

[0153] <Resin Having a Partial Structure Represented by Formula (X)> The present invention includes a resin having a partial structure represented by formula (X) (hereinafter, sometimes referred to as resin (1)). Resin (1) may contain the partial structure represented by formula (X) in the main chain of the resin or in a side chain. Resin (1) preferably has the partial structure represented by formula (X) in a side chain. Resin (1) may be a homopolymer or copolymer of compound (X) (preferably any of compounds (I) to (IX)). When the resin (1) is a copolymer, for example, it may be a copolymer of a compound (X) (preferably any one of compounds (I) to (IX)) with a polymerizable monomer. Examples of the polymerizable monomer include (meth)acrylic acid esters such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, and butyl (meth)acrylate; (meth)acrylic acid ester monomers having a hydroxy group such as 1-hydroxymethyl (meth)acrylate and 1-hydroxyethyl (meth)acrylate; vinyl monomers such as vinyl acetate and butadiene; styrene monomers such as styrene, methylstyrene, and fluorostyrene; monomers having a carboxyl group such as (meth)acrylic acid, carboxyethyl (meth)acrylate, and maleic acid; and monomers having a substituted or unsubstituted amino group such as aminoethyl (meth)acrylate and N,N-dimethylaminoethyl (meth)acrylate. When the resin (1) is a copolymer, the structural unit derived from the compound (X) (preferably any of the compounds (I) to (IX)) is preferably 0.01 to 90 parts by mass, more preferably 0.1 to 75 parts by mass, even more preferably 0.5 to 60 parts by mass, and particularly preferably 1 to 50 parts by mass, relative to 100 parts by mass of all structural units contained in the resin (A). The resin (1) can be produced by a known method such as solution polymerization, bulk polymerization, suspension polymerization, or emulsion polymerization.

[0154] <Composition containing compound (X)> The present invention also includes a composition containing compound (X) (preferably any of compounds (I) to (IX)). The composition containing compound (X) of the present invention (preferably any of compounds (I) to (IX)) is preferably a resin composition containing compound (X) (preferably any of compounds (I) to (IX)) and a resin. The composition of the present invention can be used in any application, but is particularly suitable for applications where it may be exposed to sunlight or light including ultraviolet rays.Specific examples include glass substitutes and surface coating materials thereof; coating materials for window glass, lighting glass and light source protection glass for homes, facilities, transport equipment, etc.; window films for homes, facilities, transport equipment, etc.; interior and exterior materials and interior and exterior paints for homes, facilities, transport equipment, etc. and coating films formed by said paints; alkyd resin lacquer paints and coating films formed by said paints; acrylic lacquer paints and coating films formed by said paints; components for light sources that emit ultraviolet rays such as fluorescent lamps and mercury lamps; materials for blocking electromagnetic waves generated from precision machinery, electronic and electrical equipment components, various displays; containers or packaging materials for food, chemicals, medicines, etc.; bottles, boxes, blisters, cups, special packaging, compact disc coatings, agricultural and industrial sheets or films; anti-fading agents for printed matter, dyed matter, dyes and pigments, etc.; polymer supports ( Examples of suitable applications include protective films for plastic parts such as machinery and automotive parts; overcoats for printed matter; inkjet media coatings; matte laminates; optical light films; safety glass / windshield interlayers; electrochromic / photochromic applications; overlaminate films; solar heat control films; cosmetics such as sunscreen creams, shampoos, conditioners, and hair styling products; apparel textiles and fibers such as sportswear, stockings, and hats; household interior products such as curtains, carpets, and wallpaper; medical devices such as plastic lenses, contact lenses, and artificial eyes; optical products such as optical filters, backlit display films, prisms, mirrors, and photographic materials; stationery such as mold films, transfer stickers, anti-graffiti films, tapes, and inks; sign boards, markers, and the like, and surface coating materials for such signs.

[0155] The molded article formed from the composition of the present invention is preferably a polymer molded article, and may have any shape, such as a flat film, powder, spherical particles, crushed particles, a continuous mass, fiber, tube, hollow fiber, granule, plate, or porous shape.

[0156] When the composition of the present invention is a resin composition, examples of the resin used in the resin composition include thermoplastic resins and thermosetting resins that have conventionally been used for producing various known molded articles, sheets, films, etc. Examples of thermoplastic resins include olefin-based resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin, poly(meth)acrylic acid ester-based resin, polystyrene-based resin, styrene-acrylonitrile-based resin, acrylonitrile-butadiene-styrene-based resin, polyvinyl chloride-based resin, polyvinylidene chloride-based resin, polyvinyl acetate-based resin, polyvinyl butyral-based resin, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol-based resin, polyethylene terephthalate resin, polybutylene terephthalate resin, and polyester-based resins such as liquid crystal polyester resin, polyacetal resin, polyamide resin, polycarbonate resin, polyurethane resin, and polyphenylene sulfide resin. These resins may be used as a polymer blend or polymer alloy of one or more types.

[0157] Examples of thermosetting resins include epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, and thermosetting polyimide resins.

[0158] When the resin composition is used as an ultraviolet absorbing filter or an ultraviolet absorbing film, the resin is preferably a transparent resin.

[0159] The resin composition can be obtained by mixing the compound (X) with a resin. The compound (X) may be contained in an amount necessary to impart the desired performance, for example, 0.01 to 20 parts by mass per 100 parts by mass of the resin.

[0160] When the composition of the present invention is used for optical products such as optical filters, it can be applied to, for example, optical liquid crystal displays. When the resin composition is applied to optical liquid crystal displays, the layer formed from the resin composition may be applied as any of a film layer, a pressure-sensitive adhesive layer, a hard coat layer, etc., and is preferably an pressure-sensitive adhesive layer or a hard coat layer.

[0161] <Adhesive composition> When the layer formed from the composition of the present invention is a pressure-sensitive adhesive layer, it is formed from a pressure-sensitive adhesive composition (hereinafter sometimes referred to as pressure-sensitive adhesive composition (1)) containing a resin (A), a compound (X), and an initiator (C). The pressure-sensitive adhesive composition (1) may further contain a radical-curable component (D), a crosslinking agent (E), a silane compound (F), a light-absorbing compound (G) other than the compound (X) (hereinafter sometimes referred to as the light-selective absorbing compound (G)), an antistatic agent, etc., and preferably contains at least one selected from the group consisting of the radical-curable component (D), the crosslinking agent (E), the silane compound (F), and the light-selective absorbing compound (G).

[0162] There are no particular limitations on the resin (A) as long as it is a resin that can be used in a pressure-sensitive adhesive composition. It is preferable that the resin (A) does not exhibit a maximum absorption in the wavelength range of 300 nm to 780 nm. The resin (A) preferably has a glass transition temperature (Tg) of 40°C or lower. The glass transition temperature (Tg) of the resin (A) is more preferably 20°C or lower, even more preferably 10°C or lower, and particularly preferably 0°C or lower. The glass transition temperature of the resin (A) is usually -80°C or higher, preferably -70°C or higher, more preferably -60°C or higher, even more preferably -55°C or higher, and particularly preferably -50°C or higher. A glass transition temperature of the resin (A) of 40°C or lower is advantageous in improving the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (1) to the adherend. A glass transition temperature of the resin (A) of -80°C or higher is advantageous in improving the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (1). The glass transition temperature can be measured by a differential scanning calorimeter (DSC).

[0163] Examples of the resin (A) include (meth)acrylic resins, silicone resins, rubber resins, and urethane resins, with (meth)acrylic resins being preferred.

[0164] The (meth)acrylic resin is preferably a polymer containing, as a main component (preferably containing 50% by mass or more) structural units derived from (meth)acrylic acid esters. The structural units derived from (meth)acrylic acid esters may contain structural units derived from one or more monomers other than (meth)acrylic acid esters (for example, structural units derived from monomers having polar functional groups such as hydroxyl groups, carboxyl groups, and amino groups).

[0165] The content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, and more preferably 70% by mass to 90% by mass, based on 100% by mass of the solid content of the adhesive composition (1). The content of the compound (X) is usually 0.01 to 50 parts by mass, preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, and particularly preferably 0.5 to 5 parts by mass, relative to 100 parts by mass of the resin (A).

[0166] The initiator (C) may be either a compound that initiates a polymerization reaction by absorbing heat energy (thermal polymerization initiator) or a compound that initiates a polymerization reaction by absorbing light energy (photopolymerization initiator). Here, the light is preferably active energy rays such as visible light, ultraviolet light, X-rays, or electron beams.

[0167] Examples of the thermal polymerization initiator include a compound that generates radicals upon heating or the like (thermal radical generator), a compound that generates an acid upon heating or the like (thermal acid generator), and a compound that generates a base upon heating or the like (thermal base generator). Examples of the photopolymerization initiator include a compound that generates radicals by absorbing light energy (photoradical generator), a compound that generates acid by absorbing light energy (photoacid generator), and a compound that generates a base by absorbing light energy (photobase generator).

[0168] The initiator (C) is preferably selected from those suitable for the polymerization reaction of the radically curable component (D) described below, and is preferably a radical polymerization initiator, more preferably a photoradical polymerization initiator. Examples of radical polymerization initiators include alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, and phosphine compounds. The radical polymerization initiator is preferably a photoradical polymerization initiator, and from the viewpoint of the reactivity of the polymerization reaction, it is more preferably an oxime ester-based photoradical polymerization initiator. By using an oxime ester-based photoradical polymerization initiator, the reaction rate of the radical curing component (D) can be increased even under curing conditions with low illuminance or light intensity.

[0169] The content of the initiator (C) is usually 0.01 to 20 parts by mass, preferably 0.3 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, even more preferably 0.75 to 4 parts by mass, and particularly preferably 1 to 3 parts by mass, relative to 100 parts by mass of the resin (A).

[0170] The radically curable component (D) may be a radically curable component such as a compound or oligomer that is cured by a radical polymerization reaction. Examples of the radically polymerizable component (D) include (meth)acrylate compounds, styrene compounds, and vinyl compounds. The pressure-sensitive adhesive composition (1) may contain two or more types of radically curable components (D).

[0171] Examples of (meth)acrylate compounds include (meth)acrylate monomers having at least one (meth)acryloyloxy group in the molecule, (meth)acrylamide monomers, and (meth)acryl oligomers having at least two (meth)acryloyloxy groups in the molecule, and other (meth)acryloxy group-containing compounds. The (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. The (meth)acrylate compounds may be used alone or in combination of two or more.

[0172] Examples of the (meth)acrylate monomer include a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule, a bifunctional (meth)acrylate monomer having two (meth)acryloyloxy groups in the molecule, and a polyfunctional (meth)acrylate monomer having three or more (meth)acryloyloxy groups in the molecule. A (meth)acrylate compound is preferred, and a polyfunctional (meth)acrylate compound is more preferred. The polyfunctional (meth)acrylate compound is preferably tri- or higher functional.

[0173] The content of the radical curable component (D) is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, more preferably 3 to 50 parts by mass, even more preferably 5 to 30 parts by mass, and particularly preferably 7.5 to 25 parts by mass, relative to 100 parts by mass of the resin (A).

[0174] Examples of the crosslinking agent (E) include isocyanate-based crosslinking agents, epoxy-based crosslinking agents, aziridine-based crosslinking agents, and metal chelate-based crosslinking agents. In particular, from the viewpoints of the pot life of the pressure-sensitive adhesive composition, the durability of the pressure-sensitive adhesive layer, the crosslinking rate, etc., isocyanate-based crosslinking agents are preferred. The content of the crosslinking agent (E) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, more preferably 0.15 to 7 parts by mass, even more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass, relative to 100 parts by mass of the resin (A).

[0175] Examples of the silane compound (F) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane. The silane compound (F) may be a silicone oligomer. The content of the silane compound (F) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, more preferably 0.15 to 7 parts by mass, even more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass, relative to 100 parts by mass of the resin (A).

[0176] The light-selective absorbing compound (G) is a light-absorbing compound other than the compound (X), and is, for example, a compound (ultraviolet absorber) that absorbs light with a wavelength of 250 nm to 380 nm (preferably, a wavelength of 250 nm or more and less than 360 nm). The structure of the light-selective absorption compound (G) is not particularly limited as long as it is a compound that absorbs light with a wavelength of 250 nm to 380 nm, but compounds such as benzotriazole-based compounds, benzophenone-based compounds, triazine-based compounds, salicylic acid-based compounds, cyanoacrylate-based compounds, and benzoxazine-based compounds are preferred. The content of the light-selective absorption compound (G) is usually 0.1 to 50 parts by mass, preferably 0.2 to 40 parts by mass, more preferably 0.5 to 30 parts by mass, even more preferably 1 to 25 parts by mass, and particularly preferably 2 to 20 parts by mass, relative to 100 parts by mass of the resin (A).

[0177] The pressure-sensitive adhesive composition (1) may further contain one or more additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a pigment, a rust inhibitor, an inorganic filler, and light-scattering fine particles.

[0178] <Hard coat layer> When the layer formed from the composition of the present invention is a hard coat layer, it is preferably formed from an active energy ray-curable composition containing compound (X), a photocurable component, and an initiator (hereinafter, sometimes referred to as active energy ray-curable composition (2)). The hard coat layer is, for example, a layer laminated on the outermost surface of an optical article, and has a scratch-resistant function. The active energy ray-curable composition refers to a composition that is cured by irradiation with active energy rays. Examples of active energy rays include ultraviolet rays, electron beams, X-rays, and visible light, with ultraviolet rays being preferred. The ultraviolet light source is preferably a light source having an emission distribution at a wavelength of 400 nm or less, such as a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a chemical lamp, a black light lamp, a microwave-excited mercury lamp, and a metal halide lamp.

[0179] Examples of the photocurable component include a compound or oligomer (radical polymerizable compound) that cures by a radical polymerization reaction when irradiated with active energy rays, a compound (cationic polymerizable compound) that cures by a cationic polymerization reaction when irradiated with active energy rays, and a compound that cures by an anionic polymerization reaction. The photocurable component may be a combination of a radical polymerizable compound and a cationic polymerizable compound or an anionic polymerizable compound. The active energy ray-curable composition (2) preferably contains a radically polymerizable component.

[0180] The radically polymerizable compound may be the same as the radically curable component (D) described above, and is preferably a (meth)acrylate compound, more preferably a polyfunctional (meth)acrylate compound. The content of the photocurable component is usually 50 to 99.5 mass %, and preferably 70 to 97 mass %, based on 100 mass % of the solid content of the active energy ray-curable composition (2). The content of compound (X) is usually 0.01 to 50 parts by mass, preferably 0.1 to 20 parts by mass, more preferably 0.5 to 10 parts by mass, and even more preferably 0.5 to 5 parts by mass, relative to 100 parts by mass of the photocurable component.

[0181] Examples of initiators that may be contained in the active energy ray-curable composition (2) include the same as those described above as the initiator (C). The initiator is preferably a radical polymerization initiator, more preferably a photoradical polymerization initiator, and even more preferably an oxime ester-based polymerization initiator. The content of the initiator is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 0.5 to 5 parts by mass, relative to 100 parts by mass of the photocurable component. By adding 0.5 part by mass or more of the initiator, the active energy ray-curable composition (2) can be sufficiently cured. [Example]

[0182] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the examples, % and parts representing the content or amount used are by mass unless otherwise specified.

[0183] (Example 1) Synthesis of Compound Represented by Formula (UVA-1) [ka] Under a nitrogen atmosphere, 5 parts of 4-hydroxypiperidine, 40 parts of dichloromethane, 13.6 parts of tertiary butyldiphenylchlorosilane, and 6.7 parts of imidazole were mixed and stirred at a temperature of 20 to 30°C for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 11.8 parts of a compound represented by formula (M-1).

[0184] [ka] Under a nitrogen atmosphere, 50 parts of dimedone, 47 parts of malononitrile, 115 parts of diisopropylethylamine, and 150 parts of ethanol were mixed and stirred for 3 hours at a temperature of 80° C. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 40 parts of a compound represented by formula (M-2).

[0185] [ka] Under a nitrogen atmosphere, 2 parts of the compound represented by formula (M-2), 0.6 parts of potassium hydroxide, 2.3 parts of paratoluenesulfonyl cyanide, and 10 parts of isopropanol were mixed and stirred for 3 hours at a temperature of 20 to 30° C. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 1.5 parts of the compound represented by formula (M-3).

[0186] [ka] Under a nitrogen atmosphere, 4 parts of the compound represented by formula (M-3), 3.2 parts of diisopropylethylamine, 4 parts of methyl triflate, and 80 parts of dehydrated acetonitrile were mixed and stirred for 3 hours at a temperature of 20 to 30° C. 8.3 parts of the compound represented by formula (M-1) was added to the mixture and stirred for an additional 1 hour, and the solvent was distilled off from the resulting mixture, followed by purification to obtain 7 parts of the compound represented by formula (M-4).

[0187] [ka] Under a nitrogen atmosphere, 4.2 parts of the compound represented by formula (M-4) and 60 parts of a 1 M solution of tetrabutylammonium fluoride / tetrahydrofuran were mixed and stirred for 30 hours at a temperature of 20 to 30° C. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 1.6 parts of the compound represented by formula (M-5).

[0188] [ka] Under a nitrogen atmosphere, 1.2 parts of the compound represented by formula (M-5), 0.7 parts of diisopropylethylamine, 24 parts of chloroform (trichloromethane), and 0.04 parts of dibutylhydroxytoluene were mixed, and 0.8 parts of acrylic acid chloride was added dropwise over 30 minutes while stirring in an ice bath. The mixture was stirred in the ice bath for 3 hours, and the solvent was distilled off from the mixture. The mixture was purified to obtain 0.5 parts of the compound represented by formula (UVA-1).

[0189] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (UVA-1) was produced. 1 H-NMR (deuterated dimethyl sulfoxide (deuterated DMSO)) δ: 1.00 (s, 6H), 1.38-2.10 (m, 4H), 2.54 (m, 2H), 2.69 (m, 2H), 3.83-3.96 (m, 4H), 5.12-5.14 (m, 1H), 5.99-6.41 (m, 3H) LC-MS; [M+H] + =351.5

[0190] <Measurement of maximum absorption wavelength and gram absorption coefficient ε> The resulting 2-butanone solution (0.006 g / L) of the compound represented by formula (UVA-1) was placed in a 1 cm quartz cell, and the quartz cell was placed in a spectrophotometer UV-2450 (Shimadzu Corporation). The absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps using the double-beam method. The gram extinction coefficient for each wavelength was calculated from the absorbance value, the concentration of the compound represented by formula (UVA-1) in the solution, and the optical path length of the quartz cell. ε(λ)=A(λ) / CL (where ε(λ) represents the gram absorption coefficient [L / (g cm)] of the compound represented by formula (UVA-1) at a wavelength of λ nm, A(λ) represents the absorbance at a wavelength of λ nm, C represents the concentration (g / L), and L represents the optical path length of the quartz cell [m].) The compound represented by formula (UVA-1) had a maximum absorption wavelength of 385 nm, ε(λmax) of 130.4 L / (g cm), ε(λmax+30 nm) of 7 L / (g cm), and ε(λmax) / ε(λmax+30 nm) of 18.6.

[0191] (Example 2) Synthesis of compound represented by formula (UVA-2) [ka] Under a nitrogen atmosphere, 1.1 parts of the compound represented by formula (M-3), 0.7 parts of diisopropylethylamine, 0.9 parts of methyl triflate, and 11 parts of dehydrated acetonitrile were mixed and stirred for 3 hours at a temperature of 20 to 30° C. 1.4 parts of (2-hydroxy)ethylmethylamine was added to the mixture and stirred for an additional hour, and the solvent was distilled off from the resulting mixture, followed by purification to obtain 0.5 parts of the compound represented by formula (M-6).

[0192] [ka] Under a nitrogen atmosphere, 0.7 parts of the compound represented by formula (M-6), 0.7 parts of diisopropylethylamine, 11 parts of chloroform, and 0.03 parts of dibutylhydroxytoluene were mixed, and 0.5 parts of acrylic acid chloride was added dropwise over 30 minutes while stirring in an ice bath. The mixture was stirred in the ice bath for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.3 parts of the compound represented by formula (UVA-2).

[0193] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (UVA-2) was produced. 1H-NMR (heavy DMSO) δ: 1.07 (s, 6H), 2.44 (s, 2H), 2.56 (s, 2H), 3.47 (s, 3H), 3.96 (s, 2H), 4.46~4.48 (m, 2H), 5.94~6.50 (m, 3H) LC-MS; [M+H] + =325.5

[0194] The maximum absorption wavelength and gram absorption coefficient were also measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (UVA-2) was 380 nm. The ε(λmax) of the compound represented by formula (UVA-2) was 127.4 L / (g cm), ε(λmax + 30 nm) was 6.4 L / (g cm), and ε(λmax) / ε(λmax + 30 nm) was 19.9.

[0195] (Example 3) Synthesis of compound represented by formula (UVA-3) [ka] Under a nitrogen atmosphere, 4 parts of the compound represented by formula (M-3), 2.8 parts of diisopropylethylamine, 3.6 parts of methyl triflate, and 40 parts of acetonitrile were mixed and stirred for 3 hours at a temperature of 20 to 30° C. 4 parts of 3-hydroxypyrrolidine was added to the mixture and stirred for an additional 1 hour, and the solvent was distilled off from the resulting mixture, followed by purification to obtain 2.6 parts of the compound represented by formula (M-7).

[0196] [ka] Under a nitrogen atmosphere, 3.4 parts of the compound represented by formula (M-7), 3.9 parts of diisopropylethylamine, 51 parts of chloroform, and 0.13 parts of dibutylhydroxytoluene were mixed, and 2.7 parts of acrylic acid chloride was added dropwise over 30 minutes while stirring in an ice bath. The mixture was stirred in the ice bath for 3 hours, and the solvent was distilled off from the mixture. The mixture was purified to obtain 1.6 parts of the compound represented by formula (UVA-3).

[0197] LC-MS measurement and 1H-NMR analysis confirmed that the compound represented by formula (UVA-3) was produced. 1 H-NMR (heavy DMSO) δ: 0.94~1.03(m, 6H), 1.16~1.19(m, 2H), 1.99(s, 2H), 2.66~2.77(m, 2H), 3.89~4.06(m, 4H), 5.42~5.45(m, 1H), 5.97~6.41(m, 3H) LC-MS; [M+H] + =337.5

[0198] The maximum absorption wavelength and gram absorption coefficient were also measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (UVA-3) was 380 nm. The ε(λmax) of the compound represented by formula (UVA-3) was 109.5 L / (g cm), ε(λmax + 30 nm) was 2.1 L / (g cm), and ε(λmax) / ε(λmax + 30 nm) was 52.1.

[0199] (Example 4) Synthesis of compound represented by formula (UVA-4) [ka] Under a nitrogen atmosphere, 4 parts of the compound represented by formula (M-3), 2.8 parts of diisopropylethylamine, 3.6 parts of methyl triflate, and 40 parts of acetonitrile were mixed and stirred for 3 hours at a temperature of 20 to 30° C. 4 parts of 4-(hydroxymethyl)piperidine was added to the mixture and stirred for an additional 1 hour, and the solvent was distilled off from the resulting mixture, followed by purification to obtain 2 parts of the compound represented by formula (M-8).

[0200] [ka] Under a nitrogen atmosphere, 0.9 parts of the compound represented by formula (M-8), 0.4 parts of diisopropylethylamine, 4.7 parts of chloroform, and 0.07 parts of dibutylhydroxytoluene were mixed, and 0.3 parts of acrylic acid chloride was added dropwise over 30 minutes while stirring in an ice bath. The mixture was stirred in the ice bath for 3 hours, and the solvent was distilled off from the mixture. The mixture was purified to obtain 0.7 parts of the compound represented by formula (UVA-4).

[0201] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (UVA-4) was produced. 1 H-NMR (heavy DMSO) δ: 0.95 (s, 6H), 1.36~1.91 (m, 4H), 2.50 (m, 2H), 2.75 (m, 2H), 3.29~3.33 (m, 3H), 4.03~4.32 (m, 4H), 5.95~6.37 (m, 3H) LC-MS; [M+H] + =365.5

[0202] The maximum absorption wavelength and gram absorption coefficient were also measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (UVA-4) was 385 nm. The ε(λmax) of the compound represented by formula (UVA-4) was 120.7 L / (g cm), ε(λmax + 30 nm) was 7.2 L / (g cm), and ε(λmax) / ε(λmax + 30 nm) was 16.8.

[0203] (Example 5) Preparation of adhesive composition (1) <Preparation of acrylic resin> [Polymerization Example 1]: Preparation of acrylic resin (A) A reaction vessel equipped with a condenser, nitrogen inlet, thermometer, and stirrer was charged with a mixture of 81.8 parts ethyl acetate as a solvent, 96 parts butyl acrylate, 3 parts 2-hydroxyethylmethyl acrylate, and 1 part acrylic acid. The air in the vessel was purged with nitrogen gas to remove oxygen, and the internal temperature was raised to 55°C. A solution of 0.14 parts azobisisobutyronitrile (polymerization initiator) in 10 parts ethyl acetate was then added in its entirety. After the initiator addition, the temperature was maintained at this level for 1 hour. Ethyl acetate was then added continuously to the reaction vessel at a rate of 17.3 parts / hour while maintaining the internal temperature at 54-56°C. When the acrylic resin concentration reached 35%, the ethyl acetate addition was stopped. The temperature was maintained for 12 hours after the start of the ethyl acetate addition. Finally, ethyl acetate was added to adjust the acrylic resin concentration to 20%, preparing an acrylic resin-ethyl acetate solution. The resulting acrylic resin had a weight average molecular weight Mw of 1,470,000 in terms of polystyrene measured by GPC, and an Mw / Mn ratio of 5.5, which was designated as acrylic resin (A).

[0204] To 100 parts solids of an ethyl acetate solution of acrylic resin (A) (resin concentration: 20%), 0.3 parts of crosslinker (E) (Tosoh Corporation: trade name "Coronate L", isocyanate-based compound, solids content 75%), 0.28 parts of silane compound (F) (Shin-Etsu Chemical Co., Ltd.: trade name "KBM3066"), 10 parts of radical-curable component (D) (Shin-Nakamura Chemical Co., Ltd.: trade name "A-DPH-12E", hexafunctional (meth)acrylate compound), 0.3 parts of initiator (C) (ADEKA Corporation: trade name "NCI-730", oxime ester photoradical generator), and 5 parts of compound (X) (compound represented by formula (UVA-1)) were mixed, and ethyl acetate was added to achieve a solids concentration of 14%, to obtain a pressure-sensitive adhesive composition (1). The amount of crosslinker is expressed in parts by mass as the active ingredient.

[0205] (Examples 6 to 12) and (Comparative Examples 1 to 7) Pressure-sensitive adhesive compositions (2) to (15) were prepared in the same manner as in Example 5, except that the components and the amounts of the components were changed as shown in Tables 1 and 2. The blending amount of the crosslinking agent is expressed in parts by mass as the active ingredient, and the blending amount of the resin (A) is expressed in parts by mass as the solid content.

[0206] [Table 1]

[0207] [Table 2]

[0208] The abbreviations in Tables 1 and 2 have the following meanings: Acrylic resin (A): Acrylic resin (A) synthesized in Polymerization Example 1 Formula (UVA-1): Compound represented by formula (UVA-1) synthesized in Example 1 Formula (UVA-3): Compound represented by formula (UVA-3) synthesized in Example 3 Formula (UVA-4): Compound represented by formula (UVA-4) synthesized in Example 4 NCI-730: ADEKA Corporation, product name: NCI-730, a photoradical generator that is an oxime ester compound A-DPH-12E: Product name: A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd., hexafunctional (meth)acrylate compound Coronate L: manufactured by Tosoh Corporation, product name: Coronate L, isocyanate-based crosslinking agent KBM3066: Shin-Etsu Chemical Co., Ltd., product name: KBM3066, silane coupling agent RUVA-93: Benzotriazole-based UV absorber manufactured by Otsuka Chemical Co., Ltd., product name: RUVA-93, maximum absorption wavelength λmax = 337 nm KB74: Benzotriazole-based UV absorber manufactured by Chemipro Chemical Co., Ltd., product name: KEMSORB74, maximum absorption wavelength λmax = 342 nm SB107: Benzophenone-based UV absorber manufactured by Shipro Chemical Co., Ltd., product name: SEESORB107, maximum absorption wavelength λmax = 350 nm SB707: Benzotriazole-based UV absorber manufactured by Shipro Chemical Co., Ltd., product name: SEESORB707, maximum absorption wavelength λmax = 343 nm UV3911: Orient Chemical Industry Co., Ltd., indole-based UV absorber, product name: BONASORB UA-3901, maximum absorption wavelength λmax = 393 nm Formula (a): Compound represented by the following formula (a) (synthesized by the method described in JP 2019-089997 A) [ka]

[0209] <Preparation of adhesive layer> Example 13 The pressure-sensitive adhesive composition (1) prepared above was applied to the release-treated surface of a release-treated polyethylene terephthalate separate film (trade name "PLR-382190" obtained from Lintec Corporation) using an applicator so that the dry thickness would be 5 μm, and the film was dried at a temperature of 100° C. for 1 minute. Subsequently, a pressure-sensitive adhesive layer (pressure-sensitive adhesive sheet) (1) was produced by irradiating the separate film side with UV-A (wavelength 320-390 nm) using a UV irradiation device ("Electrodeless UV Lamp System H Bulb" manufactured by Fusion UV Systems) with UV-A adjusted to an illuminance of 500 mW and an integrated light quantity of 500 mJ.

[0210] (Examples 14 to 23) and (Comparative Examples 8 to 13) As shown in Table 3, pressure-sensitive adhesive layers (2) to (17) were prepared in the same manner as in Example 13, except that the pressure-sensitive adhesive composition used and the thickness of the pressure-sensitive adhesive layer formed were changed.

[0211] (Comparative Example 14) The pressure-sensitive adhesive composition (15) prepared above was applied to the release-treated surface of a separate film made of a release-treated polyethylene terephthalate film (trade name "PLR-382190" available from Lintec Corporation) using an applicator so that the thickness after drying would be 5 μm, and the coating was dried at a temperature of 100° C. for 1 minute to produce a pressure-sensitive adhesive layer (18). The obtained adhesive layer (18) was laminated to a 23 μm cycloolefin film (ZF-14 manufactured by Zeon Corporation) using a laminator, and then cured for 7 days under conditions of a temperature of 23°C and a relative humidity of 65% to obtain an adhesive sheet (18).

[0212] <Measurement of absorbance of adhesive sheet> The obtained adhesive layer (1) to adhesive layer (17) were each attached to alkali-free glass, and after peeling off the separate film, a cycloolefin polymer (COP) film (ZF-14 manufactured by Zeon Corporation) was attached to the adhesive layer to produce a laminate having a configuration of COP film / adhesive layer / glass. The separate film of the obtained pressure-sensitive adhesive sheet (18) was peeled off and the sheet was stuck to alkali-free glass to prepare a laminate having a structure of COP film / pressure-sensitive adhesive layer / glass. The prepared laminate was set in a UV-2450 spectrophotometer (Shimadzu Corporation), and the absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps using the double beam method. The absorbance (Abs) of the prepared pressure-sensitive adhesive layer at wavelengths of 330 nm, 400 nm, and 420 nm is shown in Table 3. The absorbance of the alkali-free glass and the absorbance of the COP film at wavelengths of 330 nm, 400 nm, and 420 nm are all 0.

[0213] After the absorbance measurement, the sample was placed in a Sunshine Weather Meter (manufactured by Suga Test Instruments Co., Ltd.) for 200 hours at a temperature of 63°C and a relative humidity of 50% to conduct a weather resistance test. The absorbance of the removed sample was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 400 nm was calculated using the following formula. The results are shown in Table 3. Absorbance retention rate (%) = (A(400) after durability test / A(400) before durability test) × 100 [In the formula, A(400) represents the absorbance of the sample at a wavelength of 400 nm.]

[0214] <Evaluation of bleeding resistance of adhesive layer> A separate film was further laminated on the surface of the obtained pressure-sensitive adhesive layer to obtain a pressure-sensitive adhesive layer with double-sided separate films. The obtained pressure-sensitive adhesive layer with double-sided separate films was stored in air at a temperature of 23 to 25°C for one month. After storage, the pressure-sensitive adhesive layer with double-sided separate films was examined using a microscope to check for the presence or absence of crystalline precipitation of the compound within the surface. If no crystalline precipitation was observed, it was marked as "Good", and if crystalline precipitation was observed, it was marked as "Poor". The evaluation results are shown in Table 3.

[0215] [Table 3]

[0216] The novel compound having a merocyanine skeleton of the present invention has high absorption selectivity in the long-wave ultraviolet to near-ultraviolet region and also has good weather resistance. Even when a layer formed from a composition containing the novel compound of the present invention is made into a thin film, the compound does not precipitate and has good bleeding resistance.

Claims

1. A compound having a polymerizable group and a partial structure represented by the following formula (X): The compound having a polymerizable group and a partial structure represented by formula (X) is any one of compounds represented by the following formulas (I) to (IX): The compound, wherein the polymerizable group is an ethylenically unsaturated group. 【Chemical 1】 【Chemistry 2】 【Chemistry 3】 [In formula (X) and formulas (I) to (IX), Ring W １ , ring W 2 , ring W 3 , ring W 4 , ring W 5 , ring W 6 , ring W 7 , ring W 8 , ring W 9 , ring W 10 , ring W 11 , ring W 12 and ring W 13 each independently represent a 5- to 7-membered ring structure having a double bond as a ring component and not having aromaticity; ring W １ , ring W 2 , ring W 3 , ring W 4 , ring W 5 , ring W 6 , ring W 7 , ring W 8 , ring W 9 , ring W 10 , ring W 11 , ring W 12 and ring W 13 may have a substituent. R ３ , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 are cyano groups. R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 and R 124 are cyano groups. R 5 , R 15 , R 25 , R 35 , R 75 , R 85 and R 125 are each a cyano group, -CO-O-R 222 or -SO 2 -R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group containing the polymerizable group). In formula (I), R 1 and R 2 are At least one selected from the group consisting of R 1 and R 2 is a group containing the polymerizable group, or R 1 and R 2 are bonded to each other to form a ring, and the ring formed by bonding R 1 and R 2 to each other has the polymerizable group. R 5 is a cyano group, —CO—O—R 222 or —SO 2 —R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms). In formula (II), R 2 and R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. At least one of R 5 and R 15 is a group containing the polymerizable group. R 6 represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, and —CH 2 — contained in the divalent aliphatic hydrocarbon group may be substituted with —O—, —S—, —NR 1B — (R 1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), —CO—, —SO 2 —, —SO—, or —PO 3 —. In formula (III), At least one of R 5 and R 25 is a group containing the polymerizable group. Ring W 111 represents a 5- to 7-membered heterocyclic ring having two nitrogen atoms as constituent elements. In formula (IV), At least one of R 5 and R 35 is a group containing the polymerizable group. R 7 has the same meaning as R 6 . Ring W 112 and ring W 113 each independently represent a 5- to 7-membered heterocycle having one nitrogen atom as a constituent element. In formula (V), R 1 and R 2 have the same meanings as R 1 and R 2 in formula (I). R 8 has the same meaning as R 6 . R 41 and R 42 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing the polymerizable group, or R 41 and R 42 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has the polymerizable group. In formula (VI), R 1 and R 2 have the same meanings as R 1 and R 2 in formula (I). R 9 represents a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and —CH 2 — contained in the trivalent aliphatic hydrocarbon group may be replaced by —O—, —S—, —CS—, —CO—, —SO—, or —NR 11B — (R 11B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)—. R 51 and R 52 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing the polymerizable group, or R 51 and R 52 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has the polymerizable group. R 61 and R 62 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing the polymerizable group, or R 61 and R 62 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has the polymerizable group. In formula (VII), R 2 , R 72 and R 82 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. At least one of R 5 , R 75 and R 85 is a group containing the polymerizable group. R 10 has the same meaning as R 9 . In formula (VIII), R 1 and R 2 have the same meanings as R 1 and R 2 in formula (I). R 11 represents a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and —CH 2 — contained in the tetravalent aliphatic hydrocarbon group may be replaced by —O—, —S—, —CS—, —CO—, —SO—, or —NR 11C — (R 11C represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)-. R 91 and R 92 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing the polymerizable group, or R 91 and R 92 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has the polymerizable group. R 101 and R 102 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing the polymerizable group, or R 101 and R 102 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has the polymerizable group. R 111 and R 112 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing the polymerizable group, or R 111 and R 112 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has the polymerizable group. In formula (IX), R 2 has the same meaning as R 2 in formula (I). At least one of R 5 and R 125 is a group containing the polymerizable group. R 126 has the same meaning as R 6 .]

2. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (I).

3. At least one of R 1 and R 2 selected from the group consisting of R 1 and R 2 is a group containing the polymerizable group, 3. The compound according to claim 2, wherein R 1 and R 2 are each independently a group containing the polymerizable group or an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.

4. The compound according to claim 3, wherein R 1 and R 2 are each independently a group containing the polymerizable group or an alkyl group having 1 to 12 carbon atoms.

5. The compound according to claim 3, wherein R 1 and R 2 are each independently a group containing the polymerizable group or an alkyl group having 1 to 10 carbon atoms.

6. R 1 and R 2 are linked to each other to form a ring, and the ring formed by linking R 1 and R 2 to each other has the polymerizable group; The compound according to claim 2, wherein the ring formed by R 1 and R 2 being linked to each other is an aliphatic heterocycle.

7. The compound according to claim 6, wherein the ring formed by R 1 and R 2 bonding to each other is an aliphatic heterocycle having no unsaturated bond.

8. The compound according to claim 6, wherein the ring formed by R 1 and R 2 being linked to each other is a five-membered ring or a six-membered ring.

9. The compound according to claim 6, wherein the ring formed by R 1 and R 2 being linked together has a pyrrolidine ring structure or a piperidine ring structure.

10. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (II).

11. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (III).

12. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (IV).

13. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (V).

14. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (VI).

15. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (VII).

16. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (VIII).

17. The compound according to claim 1, wherein the compound having a polymerizable group and a partial structure represented by formula (X) is a compound represented by formula (IX).

18. A compound according to any one of claims 1 to 5 and 10 to 17, wherein the group containing a polymerizable group is a group represented by the following formula (I-2): 【Chemistry 4】 [In formula (I-2), X 2 represents the polymerizable group. R 333 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms which may have a substituent, and one —CH 2 — contained in the alkanediyl group or the divalent aromatic hydrocarbon group may be replaced with —O— or —CO—. * represents a bond.

19. The compound according to claim 1, wherein R 5 is a cyano group.

20. A compound described in any one of claims 1 to 19, wherein the polymerizable group is a (meth)acryloyl group or a (meth)acryloyloxy group.

21. Ring W １ 21. The compound according to any one of claims 1 to 20, wherein ring W 2 , ring W 3 , ring W 4 , ring W 5 , ring W 6 , ring W 7 , ring W 8 , ring W 9 , ring W 10 , ring W 11 , ring W 12 and ring W 13 are 6-membered rings.

22. The compound according to any one of claims 1 to 21, having a gram absorption coefficient ε of 50 L / (g cm) or more at the maximum absorption wavelength.

23. The compound according to any one of claims 1 to 22, wherein ε(λmax) / ε(λmax+30 nm)≧5. [ε (λmax) represents the gram absorption coefficient at the maximum absorption wavelength of a compound having a polymerizable group and a partial structure represented by formula (X)]. ε (λmax+30 nm) represents the gram absorption coefficient at (maximum absorption wavelength+30 nm) of the compound having a polymerizable group and a partial structure represented by formula (X). The unit of gram extinction coefficient is L / (g cm).

24. A composition comprising a compound according to any one of claims 1 to 23.

25. 25. The composition of claim 24, further comprising an initiator.

26. 26. The composition of claim 25, wherein the initiator is a radical polymerization initiator.

27. The composition of claim 26, wherein the initiator is a photoradical polymerization initiator.

28. The composition according to any one of claims 24 to 27, further comprising a radically polymerizable component.

29. The composition of claim 28, wherein the radically polymerizable component is a (meth)acrylate compound.

30. 30. The composition according to claim 29, wherein the radically polymerizable component is a polyfunctional (meth)acrylate compound.

31. The composition according to any one of claims 24 to 30, further comprising a resin (A).

32. The composition according to claim 31, wherein the resin (A) has a glass transition temperature of 40°C or lower.

33. The composition according to claim 32, wherein the resin having a glass transition temperature of 40°C or less is a (meth)acrylic resin.

34. The composition according to any one of claims 31 to 33, further comprising a crosslinking agent (E).

35. 35. The composition of claim 34, wherein the crosslinking agent (E) is an isocyanate crosslinking agent.

36. A hard coat layer formed from the composition according to any one of claims 24 to 30.

37. A pressure-sensitive adhesive layer comprising the composition according to any one of claims 31 to 35.

38. A molded article formed from the composition of claim 24.

39. A resin having a partial structure represented by formula (X), The resin having a partial structure represented by formula (X) is a homopolymer or copolymer of any of the compounds represented by formulas (I) to (IX) below. 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 [In formula (X) and formulas (I) to (IX), Ring W １ , ring W 2 , ring W 3 , ring W 4 , ring W 5 , ring W 6 , ring W 7 , ring W 8 , ring W 9 , ring W 10 , ring W 11 , ring W 12 and ring W 13 each independently represent a 5- to 7-membered ring structure having a double bond as a ring component and not having aromaticity; ring W １ , ring W 2 , ring W 3 , ring W 4 , ring W 5 , ring W 6 , ring W 7 , ring W 8 , ring W 9 , ring W 10 , ring W 11 , ring W 12 and ring W 13 may have a substituent. R ３ , R 13 , R 23 , R 33 , R 43 , R 53 , R 63 , R 73 , R 83 , R 93 , R 103 , R 113 and R 123 are cyano groups. R 4 , R 14 , R 24 , R 34 , R 44 , R 54 , R 64 , R 74 , R 84 , R 94 , R 104 , R 114 and R 124 are cyano groups. R 5 , R 15 , R 25 , R 35 , R 75 , R 85 and R 125 are each a cyano group, -CO-O-R 222 or -SO 2 -R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group containing a polymerizable group). In formula (I), R 1 and R 2 are At least one selected from the group consisting of R 1 and R 2 is a group containing a polymerizable group, or R 1 and R 2 are bonded to each other to form a ring, and the ring formed by bonding R 1 and R 2 to each other has a polymerizable group. R 5 is a cyano group, —CO—O—R 222 or —SO 2 —R 222 (R 222 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms). In formula (II), R 2 and R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. At least one of R 5 and R 15 is a group containing a polymerizable group. R 6 represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, and —CH 2 — contained in the divalent aliphatic hydrocarbon group may be substituted with —O—, —S—, —NR 1B — (R 1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), —CO—, —SO 2 —, —SO—, or —PO 3 —. In formula (III), At least one of R 5 and R 25 is a group containing a polymerizable group. Ring W 111 represents a 5- to 7-membered heterocyclic ring having two nitrogen atoms as constituent elements. In formula (IV), At least one of R 5 and R 35 is a group containing a polymerizable group. R 7 has the same meaning as R 6 . Ring W 112 and ring W 113 each independently represent a 5- to 7-membered heterocycle having one nitrogen atom as a constituent element. In formula (V), R 1 and R 2 have the same meanings as R 1 and R 2 in formula (I). R 8 has the same meaning as R 6 . R 41 and R 42 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing a polymerizable group, or R 41 and R 42 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has a polymerizable group. In formula (VI), R 1 and R 2 have the same meanings as R 1 and R 2 in formula (I). R 9 represents a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and —CH 2 — contained in the trivalent aliphatic hydrocarbon group may be replaced by —O—, —S—, —CS—, —CO—, —SO—, or —NR 11B — (R 11B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)—. R 51 and R 52 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing a polymerizable group, or R 51 and R 52 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has a polymerizable group. R 61 and R 62 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing a polymerizable group, or R 61 and R 62 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has a polymerizable group. In formula (VII), R 2 , R 72 and R 82 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. At least one of R 5 , R 75 and R 85 is a group containing a polymerizable group. R 10 has the same meaning as R 9 . In formula (VIII), R 1 and R 2 have the same meanings as R 1 and R 2 in formula (I). R 11 represents a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and —CH 2 — contained in the tetravalent aliphatic hydrocarbon group may be replaced by —O—, —S—, —CS—, —CO—, —SO—, or —NR 11C — (R 11C represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)-. R 91 and R 92 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing a polymerizable group, or R 91 and R 92 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has a polymerizable group. R 101 and R 102 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing a polymerizable group, or R 101 and R 102 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has a polymerizable group. R 111 and R 112 are each independently represents an alkyl group having 1 to 15 carbon atoms or a group containing a polymerizable group, or R 111 and R 112 are bonded to each other to form an aliphatic heterocycle, or the aliphatic heterocycle has a polymerizable group. In formula (IX), R 2 has the same meaning as R 2 in formula (I). At least one of R 5 and R 125 is a group containing a polymerizable group. R 126 has the same meaning as R 6 .] The polymerizable group is an ethylenically unsaturated group.]

40. 40. A composition comprising the resin of claim 39.

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