compound

Abstract

A compound having an anion represented by formula (I) [wherein ring W1 represents an optionally substituted ring; ring W2 represents a ring having at least one double bond as a ring-constituent element and the ring W2 may have a substituent; R1 and R2 each independently represent a hydrogen atom or a monovalent substituent and R1 and / or R2 has a monovalent substituent; R3, R4, R5, and R6 each independently represent a hydrogen atom or a monovalent substituent; R1 and R4 may be bonded to each other to form a ring; R3 and R4 may be bonded to each other to form a ring; R2 and R6 may be bonded to each other to form a ring; and R5 and R6 may be bonded to each other to form a ring].

Description

[Technical Field]

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

[0002] Dye compounds that absorb visible light are used in a wide range of applications, such as fibers, inks, paints, containers, packaging materials, printed materials, optical articles, eyeglasses, and display devices, for purposes such as coloring objects and transmitting or absorbing light of specific wavelengths. Important properties of dye compounds include selective absorption (sharpness of the absorption spectrum) and durability (particularly lightfastness). Among dye compounds, cyanine dyes have been widely used because, by controlling the number of methine carbon atoms in the polymethine skeleton, it is possible to control the wavelength at which they exhibit maximum absorption over a wide range, from the ultraviolet region of wavelengths of 380 nm or less to the near-infrared region of wavelengths of 780 nm or more, and because many cyanine dyes exhibit relatively high selective absorption (e.g., U.S. Pat. No. 6,004,536 (Patent Document 1)). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] U.S. Patent No. 6,004,536 Summary of the Invention [Problem to be solved by the invention]

[0004] However, although cyanine dyes have high selective absorption, many of them are poor in durability (especially lightfastness), and there has been a demand for compounds that combine high selective absorption with durability. [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] A compound having an anion represented by the following formula (I): [ka] [In formula (I), ring W 1 represents a ring which may have a substituent. Ring W 2 represents a ring having at least one double bond as a constituent element of the ring, and ring W 2 may have a substituent. R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R 2 At least one of them has a monovalent substituent. R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or a monovalent substituent. R 1 and R 4 may be linked to each other to form a ring. R 3 and R 4 may be linked to each other to form a ring. R 2 and R 6 may be linked to each other to form a ring. R 5 and R 6 may be linked to each other to form a ring. [2]R 1 and R 2 At least one selected from the group consisting of: is an electron-withdrawing group. [3]R 1 and R 2 At least one selected from the group consisting of a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -CO-R1, -CO-O-R2, and -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3z, R4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom.), -OCF3, -SCF3, -SF5, -SF3, -SO2H or -SO3H. [4]R 3 , R 4 , R 5 and R 6 The compound according to any one of [1] to [3], wherein at least one selected from the following is an electron-withdrawing group. [5]R 3 , R 4 , R 5 and R 6 are each independently an electron-withdrawing group. [6]R 3 , R 4 , R 5 and R 6 At least one selected from the group consisting of a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -CO-R1, -CO-O-R2, and -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3z , R4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom, -OCF3, -SCF3, -SF5, -SF3, -SO2H or -SO3H. [7] The compound according to any one of [1] to [6], which exhibits a maximum absorption in the wavelength range of 400 nm to 700 nm. [8] The compound according to any one of [1] to [7], which has a gram absorption coefficient at the maximum absorption wavelength of 50 [L / (g·cm)] or more. [9] A resin composition comprising the compound according to any one of [1] to [8] and a resin.

[10] A composition comprising the compound according to any one of [1] to [8] and a polymerizable monomer.

[11] A molded article molded from the resin composition according to [9] or the composition according to claim 10.

[12] An optical layer comprising the resin composition according to [9] or the composition according to claim 10.

[13] An optical laminate comprising the optical layer according to

[12] .

[14] An image display device comprising the optical laminate according to

[13] .

[15] Formula (MA) [ka] [In formula (MA), ring W 1 represents a ring which may have a substituent. Ring W 2 represents a ring having at least one double bond as a constituent element of the ring, and ring W 2 may have a substituent. R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R 2 At least one of them has a monovalent substituent. R 3 and R 4 each independently represents a hydrogen atom or a monovalent substituent. R 1 and R 4 may be linked to each other to form a ring. R 3 and R 4 may be linked to each other to form a ring. and a compound represented by formula (b-3) [ka] [In formula (b-3), R 5 and R 6 each independently represents a hydrogen atom or a monovalent substituent. X2 represents a divalent linking group. with a compound represented by formula (I): [ka] [In the formula, ring W1 , Tamaki W 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the same meaning as above.] A method for producing a compound having an anion represented by the formula:

[16] Furthermore, in the presence of a catalyst, [ka] [In the formula, ring W 1 , Tamaki W 2 , R 1 and R 2 have the same meaning as above.] and a compound represented by formula (b-2) [ka] [In the formula, R 3 and R 4 have the same meanings as above. X1 represents a divalent linking group.

[15] The method according to

[15] , comprising a step of reacting a compound represented by formula (MA) with a compound represented by formula (MA).

[17] Formula (M1-2) [ka] [In formula (M1-2), R 2’ represents a monovalent substituent, and E1 represents a leaving group. and compounds represented by formula (M1-3): [ka] [In formula (M1-3), R 1’ represents a monovalent substituent, and E2 represents a leaving group.] and at least one compound selected from compounds represented by formula (M1-1): [ka] [In formula (M1-1), ring W 1 represents a ring which may have a substituent. Ring W 2 represents a ring having at least one double bond as a constituent element of the ring, and ring W 2 may have a substituent. R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or a monovalent substituent. R 3 and R 4 may be linked to each other to form a ring. R 5 and R 6 may be linked to each other to form a ring. and a compound having an anion represented by formula (I) [ka] [In the formula, ring W 1 , Tamaki W 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as above. R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R 2 At least one of has a monovalent substituent.] A method for producing a compound having an anion represented by the formula:

[18] A compound represented by formula (M). [ka] [In formula (M), ring W 1 represents a ring which may have a substituent. Ring W 2represents a ring having at least one double bond as a constituent element of the ring, and ring W 2 may have a substituent. R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R 2 At least one of has a monovalent substituent.]

[19] A compound represented by formula (MA). [ka] [In formula (MA), ring W 1 represents a ring which may have a substituent. Ring W 2 represents a ring having at least one double bond as a constituent element of the ring, and ring W 2 may have a substituent. R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R 2 At least one of them has a monovalent substituent. R 3 and R 4 each independently represents a hydrogen atom or a monovalent substituent. R 1 and R 4 may be linked to each other to form a ring. R 3 and R 4 may be linked to each other to form a ring. [Effects of the Invention]

[0006] An object of the present invention is to provide a novel compound that exhibits good selective absorption of light in the visible light region (wavelengths of 400 nm to 750 nm, preferably 450 to 600 nm) around the maximum absorption wavelength, and also has good light resistance. DETAILED DESCRIPTION OF THE INVENTION

[0007] The compound of the present invention is a compound having an anion represented by formula (I) (hereinafter, sometimes referred to as compound (I)). [ka] [In formula (I), ring W 1 represents a ring which may have a substituent. Ring W 2 represents a ring having at least one double bond as a constituent element of the ring, and ring W 2 may have a substituent. R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R 2 At least one of them has a monovalent substituent. R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or a monovalent substituent. R 1 and R 4 may be linked to each other to form a ring. R 3 and R 4 may be linked to each other to form a ring. R 2 and R 6 may be linked to each other to form a ring. R 5 and R 6 may be linked to each other to form a ring.

[0008] <anion> The anion represented by formula (I) also includes all resonance structures such as those shown below. [ka] Also, R 3 , R 4 , R 5 and R 6 Depending on the type of monovalent substituent represented by R, electron delocalization may occur.3 , R 4 , R 5 and R 6 For example, the R 3 , R 4 , R 5 and R 6 When the delocalization of electrons extends to the monovalent substituent represented by the formula (I), the resonance structure is also included in the anion represented by the formula (I). [ka]

[0009] Ring W 1 The ring structure of ring W is not particularly limited. 1 may be a single ring or a condensed ring. Ring W 1 The ring W 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 a hydrocarbon ring consisting of carbon atoms and hydrogen atoms. 1 is preferably a hydrocarbon ring. 1 Although may be a non-aromatic ring (aliphatic ring) or an aromatic ring, an aliphatic ring is preferable. If the ring is non-aromatic, the selective absorption can be further improved. Ring W 1 is preferably a 3- to 20-membered ring structure, more preferably a 3- to 12-membered ring, and more preferably a 4- to 6-membered ring. Ring W 1 is preferably a monocyclic ring.

[0010] Ring W 2 represents a ring structure having at least one double bond as a constituent element of the ring. 2 has one or more double bonds as a ring constituent, but ring W 2 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. Ring W 2The ring W may be a monocyclic ring or a polycyclic ring. 2 Although may be an aromatic ring or a ring without aromaticity (aliphatic ring), it is preferable that it is a ring without aromaticity. If it is a ring without aromaticity, it is possible to further enhance the selective absorption. Ring W 2 may be a heterocyclic ring containing a heteroatom (for example, a nitrogen atom, an oxygen atom, a sulfur atom, etc.), or may be a ring made of a hydrocarbon. 2 is preferably a ring made of a hydrocarbon. Ring W 2 is preferably a 3- to 20-membered ring structure, more preferably a 3- to 12-membered ring, and more preferably a 4- to 6-membered ring.

[0011] Ring W 1 and Tamaki W 2 The ring W forms a condensed ring. 1 and Tamaki W 2 The fused ring formed by the above is preferably a fused ring of an aliphatic hydrocarbon, more preferably a fused ring of an aliphatic hydrocarbon having 6 to 40 carbon atoms. Ring W 1 and Tamaki W 2 The fused ring formed by the above formula (W 1 -1)~Formula(W 1 -19) and rings represented by the formula W 1 and Tamaki W 2 The fused ring formed by includes all of the above-mentioned structures in which the anionic charge is delocalized. [ka]

[0012] Ring W 1 and Ring W 2may each independently have a substituent. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; an aliphatic hydrocarbon group having 1 to 25 carbon atoms (preferably an alkyl group having 1 to 12 carbon atoms) such as a methyl group, an ethyl group, a propyl group, a normal butyl group, an isobutyl group, a tertiary butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a 2-ethylhexyl group, a 4-butyloctyl group, an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, an ethynyl group, a propynyl group, an allyl group, a cyclohexenyl group, or a butadienyl group; a fluoro group Halogenated alkyl groups having 1 to 25 carbon atoms, such as a methyl 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, a 1,1,2,2,2-pentafluoroethyl group, or a nonafluorobutyl group; alkyl groups having 1 to 25 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tertiary butoxy group, a pentyloxy group, a hexyloxy group, a 2-ethylhexyloxy group, or a 4-butyloctyloxy group; an alkoxy group; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, or a hexylthio 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, a 1,1,2,2,2-pentafluoroethoxy group, or a hexafluoroisopropoxy group; a fluorinated alkoxy group having 1 to 12 carbon atoms, such as a trifluoromethanethioalkoxy group; an amino group, a methylamino group, an ethylamino group, a dimethylamino group, an amino group optionally substituted with one or two hydrocarbon groups having 1 to 25 carbon atoms, such as a diethylamino group, a diphenylamino group, a piperidino group, a pyrrolidino group, or a methylethylamino group; a carbamoyl group optionally substituted at the N-position with an alkyl group having 1 to 6 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, or an N,N-dimethylcarbamoyl 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;Aromatic hydrocarbon groups having 6 to 25 carbon atoms, such as a phenyl group, a naphthyl group, a biphenyl group, or an anthracenyl group (preferably an aryl group having 6 to 18 carbon atoms); arylsulfonyl groups having 6 to 12 carbon atoms, such as a phenylsulfonyl group; alkoxysulfonyl groups having 1 to 12 carbon atoms, such as a methoxysulfonyl group or an ethoxysulfonyl group; fluoroalkylsulfonyl groups having 1 to 12 carbon atoms, such as a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, or a trifluoroethylsulfonyl group. Examples of such groups include acyl groups having 2 to 12 carbon atoms, such as an acetyl group or an ethylcarbonyl group; an aldehyde group; an alkoxycarbonyl group having 2 to 12 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group or a butyloxycarbonyl group; an alkoxythiocarbonyl group having 2 to 12 carbon atoms, such as a methoxythiocarbonyl group or an ethoxythiocarbonyl group; a cyano group; a nitro group; a hydroxyl group; a thiol group; a sulfo group; a carbamoyl group; a carboxyl group; -SF3; and -SF5. Ring W 1 and Ring W 2 The fused ring formed from may also have a substituent, and the substituent is ring W 1 or Ring W 2 Examples of the substituents that may be possessed by the group include:

[0013] R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, and R 1 and R 2 At least one selected from the group consisting of is a monovalent substituent. R 1 and R 2 The monovalent substituent represented by the formula (I) is not particularly limited as long as it is not a hydrogen atom, and examples thereof include a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron-withdrawing group, an electron-donating group, a heterocyclic group, and a group having a polyoxyalkylene group.

[0014] R 1 and R 2Examples of the monovalent aliphatic hydrocarbon group 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, an isohexyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decyl group, an isodecyl group, an n-dodecyl group, an isododecyl group, an undecyl group, a lauryl group, a myristyl group, a cetyl group, a stearyl group, a 2-ethylhexyl group, and a 4-butyloctyl group. Examples of such groups include linear or branched alkyl groups having 1 to 25 carbon atoms: cycloalkyl groups having 3 to 25 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; cycloalkylalkyl groups having 4 to 25 carbon atoms such as cyclohexylmethyl; alkylcycloalkyl groups having 4 to 25 carbon atoms such as isobornyl; and unsaturated aliphatic hydrocarbon groups such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl, and butadienyl. Preferred are linear or branched alkyl groups having 1 to 12 carbon atoms.

[0015] R 1 and R 2 Examples of the monovalent aromatic hydrocarbon group represented by the formula (I) include aryl groups having 6 to 18 carbon atoms, such as phenyl, naphthyl, anthracenyl, tetracenyl, pentacenyl, phenanthryl, chrysenyl, triphenylenyl, tetraphenyl, pyrenyl, perylenyl, coronenyl, and biphenyl; aralkyl groups having 7 to 18 carbon atoms, such as benzyl, phenylethyl, and naphthylmethyl; and arylalkoxy groups, such as phenoxyethyl, phenoxydiethylene glycol, and phenoxypolyalkylene glycol groups. An aryl group having 6 to 18 carbon atoms is preferred, and is a phenyl or benzyl group.

[0016] R 1 and R 2Examples of the electron-donating group represented by the formula (I) include a hydroxyl group; an alkoxy group having 1 to 25 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, or 4-butyloctyloxy group; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, or hexylthio group; and an amino group which may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, or a methylethylamino group.

[0017] R 1 and R 2 Examples of the heterocyclic group represented by the formula (I) include aliphatic heterocyclic groups having 4 to 20 carbon atoms, such as a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, a piperidine ring group, a morpholine ring group, a piperazine ring group, an indole ring group, an isoindole ring group, a quinoline ring group, a thiophene ring group, a pyrrole ring group, a thiazoline ring group, a furan ring group, and a tetrahydrofuran ring group, or aromatic heterocyclic groups having 3 to 20 carbon atoms.

[0018] R 1 and R 2 The group having a polyoxyalkylene group represented by the formula (I) is a group having an oxyethylene group (-CH2CH2O-), an oxypropyl group (-CH2CH2CH2O-), etc. More specifically, -(X 11 O)mR 11 A group represented by (X 11 represents an alkylene group having 1 to 6 carbon atoms, and R 11 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, and m represents an integer of 1 to 6.

[0019] R 1 and R 2Examples of the electron-withdrawing group represented by formula (z-1) include 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, and a group represented by formula (z-1). [ka] [In formula (z-1), R 222 represents a group having a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a polyoxyalkylene group. 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.]

[0020] 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 halogenated alkyl groups having 1 to 25 carbon atoms, such as trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, perfluorohexyl, dichloromethyl, bromomethyl, and iodomethyl. Preferred are halogenated alkyl groups having 1 to 12 carbon atoms, more preferred are fluoroalkyl groups having 1 to 12 carbon atoms, and even more preferred are perfluoroalkyl groups having 1 to 12 carbon atoms. Examples of the halogenated aryl group include halogenated aryl groups having 6 to 18 carbon atoms, such as a fluorophenyl group, a chlorophenyl group, and a bromophenyl group. A fluoroaryl group having 6 to 18 carbon atoms is preferred, a perfluoroaryl group having 6 to 12 carbon atoms is more preferred, and a pentafluorophenyl group is even more preferred.

[0021] X 1 is preferably —CO—, —COO— or —SO 2 —. R 222 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 222 Examples of the hydrocarbon group represented by the formula include an aliphatic hydrocarbon group having 1 to 25 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms. Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include linear, branched, and cyclic alkyl groups having 1 to 25 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1-methylbutyl, 3-methylbutyl, n-octyl, n-decyl, 2-hexyloctyl, 4-butyloctyl, and cyclohexyl groups; and unsaturated aliphatic hydrocarbon groups, such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl, and butadienyl groups, with alkyl groups having 1 to 12 carbon atoms being preferred. Examples of aromatic hydrocarbon groups having 6 to 18 carbon atoms 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 hydrocarbon group represented by the formula (I) may have include a halogen atom, a hydroxy group, an alkoxy group, a thioalkyl group, and a dialkylamino group. R 222 Examples of the group having a polyoxyalkylene group represented by the formula: R 1The polyoxyalkylene group may be the same as the group having a polyoxyalkylene group represented by the following formula:

[0022] 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.

[0023] The group represented by formula (z-1) is -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3z and R4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom. More preferably, —CO—R1, —CO—O—R2, —SO2—R9; More preferably, —SO2—R9; -SO2-R 10 (R 10 is even more preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), -SO2CF3, -SO2CHF2, or -SO2CH2F.

[0024] R 1 and R 2 At least one selected from the group consisting of: is preferably an electron-withdrawing group, and is selected from the group consisting of a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, and -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3zR4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom, and more preferably -OCF3 or -SCF3; More preferably, it is a cyano group, a nitro group, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, or -SO2-R9; Cyano group, nitro group, -OCF3, -SCF3, -SF5, -SO2CF3, -SO2-R 10 Even more preferably, A cyano group or a nitro group is particularly preferred.

[0025] R 3 , R 4 , R 5 and R 6 The monovalent substituent represented by R 1 The monovalent substituents represented by the following formula (1) are exemplified. R 3 , R 4 , R 5 and R 6 Preferably, at least one selected from the following is an electron-withdrawing group: Cyano group, nitro group, halogenated alkyl group, halogenated aryl group, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3z R4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom, and more preferably -OCF3 or -SCF3; More preferably, it is a cyano group, a nitro group, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, or -SO2-R9; Cyano group, nitro group, -OCF3, -SCF3, -SF5, -SO2CF3, -SO2-R 10 Even more preferably, A cyano group or a nitro group is particularly preferred.

[0026] R 3 , R 4 , R 5 and R 6 are each preferably an electron-withdrawing group. R 3 , R 4 , R 5 and R 6 are each independently a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, or -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3z R4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom, and more preferably -OCF3 or -SCF3; More preferably, it is a cyano group, a nitro group, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, or -SO2-R9; Cyano group, nitro group, -OCF3, -SCF3, -SF5, -SO2CF3, -SO2-R 10 Even more preferably, A cyano group or a nitro group is particularly preferred.

[0027] R 1 and R 4 may be linked to each other to form a ring. 1 and R 4 The ring formed by connecting these is R 1 and R 4 and are connected to each other to form a ring, ring W 1 and Ring W 2 At least three fused rings are formed by R 1 and R 4 and are connected to each other to form a ring, ring W1 and Ring W 2 Examples of the anion represented by formula (I) having a fused ring formed by the formula include the anions described below. [ka]

[0028] R 1 and R 4 and are connected to each other to form a ring, ring W 1 and Ring W 2 The anion represented by formula (I) having a fused ring formed by the formula (I-W2), (I-W3), (I-W4), (I-W5), (I-W6), (I-W7), or (I-W14) is preferably an anion represented by formula (I-W2), (I-W3), (I-W4), (I-W5), (I-W6), (I-W7), or (I-W14). R 1 and R 4 The ring formed by linking together may have a substituent. Examples of the substituent include ring W 1 and Ring W 2 The substituents are the same as those that may be contained in the group.

[0029] R 2 and R 6 may be linked to each other to form a ring. 2 and R 6 The ring formed by connecting these is R 2 and R 6 and are connected to each other to form a ring, ring W 1 and Ring W 2 At least three fused rings are formed by R 2 and R 6 and are connected to each other to form a ring, ring W 1 and Ring W 2 Examples of the anion represented by formula (1) having a fused ring formed by the formula include the anions shown below. [ka]

[0030] R 2 and R 6and are connected to each other to form a ring, ring W 1 and Ring W 2 The anion represented by formula (I) having a fused ring formed by the formula (I-w2), (I-w3), (I-w4), (I-w5), (I-w6), (I-w7) or (I-w14) is preferably an anion represented by formula (I-w2), (I-w3), (I-w4), (I-w5), (I-w6), (I-w7) or (I-w14). R 2 and R 6 The ring formed by linking together may have a substituent. Examples of the substituent include ring W 1 and Ring W 2 The substituents are the same as those that may be contained in the group.

[0031] R 3 and R 4 may be linked to each other to form a ring. 3 and R 4 The ring formed by combining R and R together may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring. 3 and 4 2 The ring formed by bonding together may contain a heteroatom (nitrogen atom, oxygen atom, sulfur atom) or the like as a ring component. R 3 and R 4 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.

[0032] R 3 and R 4 Examples of the ring formed by bonding together include the rings shown below. In the rings shown below, * indicates a ring W. 1 Represents a bond with . [ka]

[0033] R 3 and R 4and (w-45), (w-47), or (w-48).

[0034] R 5 and R 6 The ring formed by connecting these is R 3 and R 4 The ring formed by connecting R 5 and R 6 and (w-45), (w-47), or (w-48).

[0035] The anion represented by formula (I) is more preferably an anion represented by formula (IA). [ka] [In formula (IA), R 1 ~R 6 each independently represents the same meaning as above.]

[0036] Examples of the anion represented by formula (I) include the anions shown below: In the formula, Me represents a methyl group. [ka]

[0037] [ka]

[0038]

change

[0039]

change

[0040]

change

[0041]

change

[0042]

change

[0043]

change

[0044]

change

[0045]

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[0046]

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[0047]

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[0048]

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[0049] [ka]

[0050] [ka]

[0051] <cation> The compound of the present invention is composed of an anion represented by formula (I) and a paired cation. The combination of the anion represented by formula (I) and the cation in the compound of the present invention is not limited. The cation may be an organic cation or an inorganic cation.

[0052] Examples of organic cations include pyridinium cations such as N-methylpyridinium, N-ethylpyridinium, N-propylpyridinium, N-ethyl-2-methylpyridinium, N-ethyl-3-methylpyridinium, 1-ethyl-3-(hydroxymethyl)pyridinium, N-butylpyridinium, N-butyl-4-methylpyridinium, N-butyl-3-methylpyridinium, N-hexylpyridinium, N-octylpyridinium, N-octyl-4-methylpyridinium, 1,1'-dimethyl-4,4'-bipyridinium, and 1,1'-dibenzyl-4,4'-bipyridinium; piperidinium cations such as 1-butyl-1-methylpiperidinium and 1-methyl-1-propylpiperidinium; pyrrolidinium cations such as 1-allyl-1-methylpyrrolidinium, 1-butyl-1-methylpyrrolidinium, 1-ethyl-1-methylpyrrolidinium, 1-methyl-1-propylpyrrolidinium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, 1-methyl-1-n-octylpyrrolidinium, and 1-methyl-1-pentylpyrrolidinium; Cations having a pyrroline skeleton, such as 2-methyl-1-pyrrolinium; imidazolium cations such as 1-butyl-2,3-dimethylimidazolium, 3,3'-(butane-1,4-diyl)bis(1-vinyl-3-imidazolium), 1-benzyl-3-methylimidazolium, 1,3-dimethylimidazolium, 1,2-dimethyl-3-propylimidazolium, 1-decyl-3-methylimidazolium, 1-dodecyl-3-methylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 3-ethyl-1-vinylimidazolium, 3-ethyl-1-vinylimidazolium, 1-methyl-3-(4-sulfobutyl)imidazolium, 1-ethyl-3-methylimidazolium, and 1-butyl-3-methylimidazolium; Ammonium cations such as amyltriethylammonium, butyltrimethylammonium, benzyl(ethyl)dimethylammonium, cyclohexyltrimethylammonium, diethyl(methyl)propylammonium, diethyl(2-methoxyethyl)methylammonium, ethyl(2-methoxyethyl)dimethylammonium, ethyl(dimethyl)(2-phenylethyl)ammonium, methyltri-n-octylammonium, tetrabutylammonium, tetrahexylammonium, tetrapentylammonium, tetra-n-octylammonium, tetraheptylammonium, and tetrapropylammonium; trialkylsulfonium cations such as trimethylsulfonium, tributylsulfonium, and triethylsulfonium; phosphonium cations such as tributylhexadecylphosphonium, tributylmethylphosphonium, tributyl-n-octylphosphonium, tributyl-n-octylphosphonium, tetra-n-octylphosphonium, tributyl(2-methoxyethyl)phosphonium, tributylmethylphosphonium, trihexyl(tetradecyl)phosphonium, and trihexyl(tetradecyl)phosphonium; morpholinium cations such as 4-ethyl-4-methylmorpholinium; Examples include triarylmethane cations such as triphenylmethylium.

[0053] Inorganic cations include alkali metal ions such as lithium ion, sodium ion, potassium ion, rubidium ion, and cesium ion; monovalent metal ions such as copper (I) ion and silver ion; alkaline earth metal ions such as beryllium ion, magnesium ion, calcium ion, strontium ion, and barium ion; divalent metal ions such as copper (II) ion, nickel ion, cobalt ion, iron (II) ion, manganese ion, palladium ion, zinc ion, and germanium (II) ion; trivalent metal ions such as cobalt (III) ion, iron (III) ion, chromium (III) ion, scandium ion, yttrium ion, ruthenium (III) ion, and gallium ion; tetravalent metal ions such as titanium ion, zirconium ion, hafnium ion, germanium (IV) ion, and molybdenum (IV) ion; and NH4 + etc.

[0054] The cation is preferably an alkali metal ion, an alkaline earth metal ion, a copper (I) ion, a copper (II) ion, a nickel ion, a cobalt (III) ion, an iron (II) ion, an iron (III) ion, a palladium ion, or an organic cation, more preferably a potassium ion, a calcium ion, a barium ion, a magnesium ion, a copper (I) ion, a copper (II) ion, a nickel ion, or an organic cation, and even more preferably a potassium ion or an organic cation.

[0055] The compound (I) is preferably a compound represented by formula (IA), although the combination of the anion and cation represented by formula (I) is not limited. [ka] [In the formula, W 1 , W 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as above. g represents an integer of 1 to 4. G represents a monovalent cation, a divalent cation, a trivalent cation, or a tetravalent cation.

[0056] The molecular weight of compound (I) is preferably 3000 or less, more preferably 2000 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.

[0057] Compound (I) preferably exhibits a maximum absorption at a wavelength of 450 nm to 650 nm.

[0058] The gram absorption coefficient ε of compound (I) at the maximum absorption wavelength (λmax) is preferably 50 [L / (g cm)] or more, more preferably 100 [L / (g cm)] or more, and particularly preferably 150 [L / (g cm)] or more. There is no upper limit, but it is generally 100,000 [L / (g cm)] or less. It is preferable that the gram absorption coefficient ε at λmax of compound (I) is 50 [L / (g·cm)] or more, since light in the vicinity of the maximum absorption wavelength can be efficiently absorbed.

[0059] The full width at half maximum of Compound (I) is preferably 45 nm or less, more preferably 40 nm, even more preferably 35 nm, and particularly preferably 30 nm or less. The full width at half maximum can be measured by the method described in the Examples.

[0060] Examples of compound (I) include the compounds shown in the following Tables 1 to 6. Compound (1) has an anion represented by formula (I-1) and a lithium ion, and has the structure shown below. [ka]

[0061] [Table 1]

[0062] Table 2

[0063] Table 3

[0064] Table 4

[0065] Table 5

[0066] Table 6

[0067] Compound (I) includes Compound (1) to Compound (3), Compound (6) to Compound (11), Compound (14) to Compound (16), Compound (18), Compound (19), Compound (21), Compound (24) to Compound (30), Compound (32), Compound (35) to Compound (38), Compound (41), Compound (44), Compound (47), Compound (50), Compound (52) to Compound (55), Compound (57), Compound (59), Compound (61), Compound (63), Compound (65), Compound (67), Compound (70), Compound (72), Compound (74), Compound (76), Compound (78), Compound (80), Compound (81), Compound (83), Compound (86) to Compound (88), Compound (95), Compound (96), Compound (107), Compound (108) , Compound (110) ~ Compound (112), Compound (114) ~ Compound (121), Compound (123) ~ Compound (129), Compound (132), Compound (133), Compound (135) ~ Compound (138), Compound (140) ~ Compound (143), Compound (145) ~ Compound (147), Compound (149) ~ Compound (155), Compound (158), Compound (159), Compounds (161) to (164), compounds (166) to (169), compounds (171) to (173), compounds (175), compounds (176), compounds (179) to (181), compounds (184), compounds (185), compounds (187) to (189), compounds (191), and compounds (193) to (198) are preferred.

[0068] <Method for producing compound (I) (1)> Compound (I) can be obtained, for example, by reacting at least one compound selected from a compound represented by formula (M1-2) (hereinafter, sometimes referred to as compound (M1-2)) and a compound represented by formula (M1-3) (hereinafter, sometimes referred to as compound (M1-3)) with a compound having an anion represented by formula (M1-1) (hereinafter, sometimes referred to as compound (M1-1)). [ka] [In formula (M1-1), ring W 1, Tamaki W 2 , R 3 , R 4 , R 5 and R 6 has the same meaning as above. In formula (M1-2), R 2’ represents a monovalent substituent, and E1 represents a leaving group. In formula (M1-3), R 1’ represents a monovalent substituent, and E2 represents a leaving group.]

[0069] R 2’ The monovalent substituent represented by R 2 The monovalent substituents represented by the following formula (1) are exemplified. R 1’ The monovalent substituent represented by R 1 The monovalent substituents represented by the following formula (1) are exemplified. The leaving groups represented by E1 and E2 each independently include a halogen atom, a succinimide group, a maleimide group, an o-sulfobenzimid group, a methylsulfonyl group, a p-methoxybenzenesulfonyl group, a p-toluenesulfonyl group, a trifluoromethylsulfonyl group, and a nonafluorobutanesulfonyl group.

[0070] The reaction of compound (M1-1) with at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) is carried out by mixing at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1). The amount of compound (M1-2) used is usually 0.1 to 20 mol, preferably 0.5 to 10 mol, per 1 mol of compound (M1-1). The amount of compound (M1-3) used is usually 0.1 to 20 mol, preferably 0.5 to 10 mol, per 1 mol of compound (M1-1).

[0071] The reaction of at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) with the compound (M1-1) is preferably carried out in the presence of a base. Examples of the base include metal alkoxides (preferably alkali metal alkoxides) such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tertiary butoxide, and potassium tertiary butoxide; metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride, and sodium borohydride; metal carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, lithium carbonate, lithium hydrogen carbonate, and cesium carbonate; organic lithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, and phenyllithium; alkyl metal halides such as magnesium bromide, isopropyl magnesium bromide, n-butyl magnesium bromide, and isopropyl magnesium chloride; metal amide compounds such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, and lithium tetramethylpiperidide; amine compounds such as pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, and ethylenediamine; metal carboxylates such as sodium acetate, potassium acetate, and sodium formate; and ammonium carboxylates such as ammonium acetate. The amount of the base used is usually 0.001 to 20 mol, preferably 0.03 to 10 mol, more preferably 0.05 to 5 mol, still more preferably 0.1 to 3 mol, and particularly preferably 0.5 to 2 mol, relative to 1 mol of compound (M1-1).

[0072] The reaction of at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) with the compound (M1-1) may be carried out in the presence of a solvent. Examples of the solvent include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents such as benzene, toluene, xylene, and anisole; aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, and methylcyclohexane; halogenated solvents such as chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and n-propyl acetate; methanol, ethanol, isopropanol, hexafluoroisopropanol, n-butanol, and isobutyl acetate. Examples of suitable solvents include alcohol solvents such as ethanol and tert-butanol; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ether solvents such as tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentyl methyl ether, 4-methyltetrahydropyran, dioxane, diethyl ether, tert-butyl methyl ether, diisopropyl ether, dimethoxyethane, and diethoxymethane; amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; hexamethylphosphoric triamide; and water. The solvent is preferably a nitrile solvent, an alcohol solvent, an ether solvent, a ketone solvent, or an aromatic hydrocarbon solvent, more preferably acetonitrile, tetrahydrofuran, diethyl ether, methanol, ethanol, isopropanol, 2-butanone, or toluene, still more preferably acetonitrile, tetrahydrofuran, methanol, ethanol, isopropanol, 2-butanone, or toluene, and particularly preferably methanol, ethanol, isopropanol, acetonitrile, 2-butanone, or toluene. The reaction time of the compound (M1-1) with at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) is usually 0.01 to 200 hours. The reaction temperature of the compound (M1-1) with at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) is usually -100 to 200°C.

[0073] Examples of the compound (M1-1) include the compounds shown below. [ka]

[0074] As the compound (M1-2) and the compound (M1-3), commercially available products may be used. For example, cyanogen chlorate, cyanogen bromide, paratoluenesulfonyl cyanide, trifluoromethanesulfonyl cyanide, benzyl thiocyanate, tert-butyl isocyanide, copper(I) cyanide, potassium cyanide, 1-cyano-4-(dimethylamino)pyridinium tetrafluoroborate, p-toluenesulfonylmethyl isocyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Select Floor (Air Products and (also known as a registered trademark of Chemicals), benzoyl(phenyliodonio)(trifluoromethanesulfonyl)methanide, 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate, 1-fluoro-3,3-dimethyl-1,2-benziodoxol, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide, tetramethylammonium tribromide, fluorine (F2), bromine (Br2), chlorine (Cl2), iodine (I2), N-bromophthalimide, N-chlorophthalimide Examples of the saccharin include 1-trifluoromethyl-3,3-dimethyl-1,2-benzoiodoxol, 1-trifluoromethyl-1,2-benzoiodoxol-3(1H)-one, nitric acid, iodomethane, dimethyl sulfate, methyl triflate, ethyl triflate, normal butyl triflate, and acetyl chloride. In addition, R 1’ and R 2’ are the same group, and E1 and E2 are the same group, the compound (M1-2) and the compound (M1-3) are the same compound.

[0075] By reacting at least one compound selected from the group consisting of compounds (M1-2) and (M1-3) with compound (M1-1), compound (I) having a cation derived from compound (M1-1) and an anion represented by formula (I) can be obtained. When the cation of compound (I) is to be exchanged for a desired cation, ion exchange can be performed by mixing compound (I) with a salt having the desired cation. The ion exchange can be performed in the presence of a solvent. Examples of salts having the desired cation include chloride salts consisting of the desired cation and chloride ions, bromide salts consisting of the desired cation and bromide ions, iodide salts consisting of the desired cation and iodide ions, fluoride salts consisting of the desired cation and fluoride ions, nitrates consisting of the desired cation and nitrate ions, sulfates consisting of the desired cation and sulfate ions, perchlorates consisting of the desired cation and perchlorate ions, sulfonates consisting of the desired cation and sulfonate ions, carboxylates consisting of the desired cation and carboxylate ions, hypochlorites consisting of the desired cation and hypochlorite ions, hexafluorophosphate salts consisting of the desired cation and hexafluorophosphate, and imide salts consisting of the desired cation and imide.

[0076] The compound (I) having a divalent or higher cation can be obtained by obtaining the compound (I) having a monovalent cation and then performing ion exchange. Alternatively, the compound (I) can be obtained by using the compound (M1-1) having a divalent or higher cation when reacting the compound (M1-1) with at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3).

[0077] The anion moiety in compound (M1-1) can be produced by reacting a compound represented by formula (M1-4) (hereinafter, sometimes referred to as compound (M1-4)), a compound represented by formula (b-2) (hereinafter, sometimes referred to as compound (b-2)), and a compound represented by formula (b-3) (hereinafter, sometimes referred to as compound (b-3)). [ka] [In formula (M1-4), ring W 1 and Ring W 2 has the same meaning as above. In formula (b-2), R 3 and R 4 has the same meaning as above, and X1 represents a divalent linking group. In formula (b-3), R 5 and R 6 represents the same meaning as above, and X2 represents a divalent linking group.

[0078] The reaction of the compound (M1-4), the compound (b-2) and the compound (b-3) is carried out by mixing the compound (M1-4), the compound (b-2) and the compound (b-3). The reaction of compound (M1-4), compound (b-2), and compound (b-3) is preferably carried out in the presence of a base, and compound (M1-4), compound (b-2), compound (b-3), and a base are preferably mixed together. The compound (M1-4), the compound (b-2), the compound (b-3), and the base are preferably mixed by adding the compound (b-2) to a mixture (1) of the compound (M1-4) and a portion of the base to obtain a mixture (2), and then adding a mixture (3) of the compound (b-3) and the remainder of the base to the obtained mixture (2).

[0079] The reaction of compound (M1-4), compound (b-2), compound (b-3), and a base may be carried out in the presence of a solvent. Examples of the solvent include the same solvents that can be used in the reaction of at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1). Preferred solvents include acetonitrile, ethanol, methanol, 2-butanone, toluene, 2-butanone, tetrahydrofuran, and dioxane. The solvent is preferably a dehydrated solvent.

[0080] The reaction time of the compound (M1-4), the compound (b-2), the compound (b-3) and the base is usually 0.05 to 100 hours. The reaction temperature of the compound (M1-4), the compound (b-2), the compound (b-3) and the base is usually -100 to 200°C. The amount of compound (b-2) used is usually 0.01 to 10 moles per mole of compound (M1-4). The amount of compound (b-3) used is usually 0.01 to 10 moles per mole of compound (M1-4). The amount of the base used is usually 0.01 to 10 moles per mole of compound (M1-4).

[0081] As the compound (M1-4), commercially available products may be used, and examples thereof include 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one.

[0082] Compound (b-2) and compound (b-3) may each independently be commercially available products, and examples thereof include malononitrile, 2-cyanoacetamide, cyanoacetic acid, methyl cyanoacetate, ethyl cyanoacetate, propyl cyanoacetate, isopropyl cyanoacetate, butyl cyanoacetate, tert-butyl cyanoacetate, 2-ethylhexyl cyanoacetate, 2-ethoxyethyl cyanoacetate, 2-cyano-N,N-dimethylacetamide, pivaloylacetonitrile, cyanoacetylurea, benzoylacetonitrile, 2-cyanoacetanilide, 3-oxo-3-(2-thienyl)-2-methyl-2-propanol, and the like. (I) propanenitrile, methyl acetoacetate, dimedone, 1,3-cyclopropanedione, tetronic acid, acetylacetone, malonamide, malonic acid, 1,3-cyclohexanedione, 2,4-piperidinedione, 1,3-cycloheptanedione, barbituric acid, 3,5-heptanedione, dimethyl malonate, Meldrum's acid, 1,3-indanedione, trifluoroacetylacetone, 1,3-dimethylbarbituric acid, 1,3-dicyclohexylbarbituric acid, 2-thiobarbituric acid, 1,3-diethyl-2-thiobarbituric acid, and the like. In addition, X1 and X2 are the same group, and R 3 and R 4 are the same group, and R 5 and R 6When these are the same group, the compound (b-2) and the compound (b-3) are the same compound.

[0083] Examples of the base include the same bases that can be used in the reaction of at least one compound selected from the group consisting of compounds (M1-2) and (M1-3) with compound (M1-1). Compound (M1-1) usually has a cation derived from the base. For example, if the cation derived from the base is monovalent, a compound consisting of a monovalent cation and one anion represented by formula (M1-1) is obtained. If the cation derived from the base is divalent, a compound consisting of a divalent cation and two anions represented by formula (M1-1) is obtained.

[0084] <Method for producing compound (I) (2)> The anion moiety of compound (I) can also be produced by reacting a compound represented by formula (MA) (hereinafter sometimes referred to as compound (MA)) with compound (b-3). [ka] [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X2, W 1 and W 2 have the same meaning as above.]

[0085] The reaction between compound (MA) and compound (b-3) is preferably carried out in the presence of a catalyst. Examples of the catalyst include carboxylic acids such as formic acid, acetic acid, and trifluoroacetic acid; ammonium chloride; Lewis acids such as titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride, and lanthanoid triflates; sulfonic acid anhydrides such as methanesulfonic acid anhydride, paratoluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, and nonafluorobutanesulfonic acid anhydride; sulfonic acids such as paratoluenesulfonic acid, trifluoromethanesulfonic acid, and fluorosulfuric acid; electrophilic alkylating agents such as dimethyl sulfate, methyl triflate (methyl trifluoromethanesulfonate), iodomethane, trimethyloxonium tetrafluoroborate, and dimethyl fluorosulfate; and sulfonic acid halides such as paratoluenesulfonyl chloride and trifluoromethanesulfonyl chloride. Preferably, the alkylating agent is an electrophilic alkylating agent, a sulfonic acid anhydride, or a sulfonic acid halide, more preferably, dimethyl sulfate, methyl triflate, paratoluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, paratoluenesulfonyl chloride, or trifluoromethanesulfonyl chloride, and even more preferably, methyl triflate or trifluoromethanesulfonic acid anhydride.

[0086] The reaction of compound (MA) with compound (b-3) is preferably carried out in the presence of a base. Examples of the base include the same bases that can be used in the reaction of at least one compound selected from the group consisting of the compounds (M1-2) and (M1-3) with the compound (M1-1). The reaction of compound (MA) with compound (b-3) may be carried out in the presence of a solvent, such as the same solvents that can be used in the reaction of at least one compound selected from the group consisting of compounds (M1-2) and (M1-3) with compound (M1-1). The solvent is preferably a dehydrated solvent.

[0087] The reaction of compound (MA) with compound (b-3) is preferably carried out by mixing a catalyst, compound (MA), and compound (b-3), and more preferably by mixing a catalyst, a base, compound (MA), and compound (b-3). The reaction between compound (MA) and compound (b-3) is preferably carried out in an oxygen-free atmosphere (for example, in a nitrogen atmosphere).

[0088] The amount of compound (b-3) used is usually 0.01 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of compound (MA). The amount of the catalyst used is usually 0.001 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of compound (MA). The amount of the base used is usually 0.001 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of compound (MA). The reaction time of the compound (MA) and the compound (b-3) is usually 0.01 to 200 hours. The reaction temperature of the compound (MA) and the compound (b-3) is usually -100 to 200°C.

[0089] Examples of the compound (MA) include the compounds shown below. [ka]

[0090] When compound (MA) and compound (b-3) are reacted in the presence of a base, compound (I) having a cation derived from the base and an anion represented by formula (I) can be obtained. When the cation of compound (I) is to be exchanged for a desired cation, ion exchange can be performed by mixing compound (I) with a salt having the desired cation. The ion exchange can be performed in the presence of a solvent. Examples of salts having the desired cation include chloride salts consisting of the desired cation and chloride ions, bromide salts consisting of the desired cation and bromide ions, iodide salts consisting of the desired cation and iodide ions, fluoride salts consisting of the desired cation and fluoride ions, nitrates consisting of the desired cation and nitrate ions, sulfates consisting of the desired cation and sulfate ions, perchlorates consisting of the desired cation and perchlorate ions, sulfonates consisting of the desired cation and sulfonate ions, carboxylates consisting of the desired cation and carboxylate ions, hypochlorites consisting of the desired cation and hypochlorite ions, hexafluorophosphate salts consisting of the desired cation and hexafluorophosphate, and imide salts consisting of the desired cation and imide.

[0091] Compound (MA) can be produced by reacting a compound represented by formula (M) (hereinafter, sometimes referred to as compound (M)) with compound (b-2) in the presence of a catalyst. [ka] [In the formula, ring W 1 , Tamaki W 2 , R 1 , R 2 , R 3 , R 4 and X1 have the same meanings as above.]

[0092] Examples of the catalyst include the same catalysts that can be used in the reaction of compound (MA) with compound (b-3). Preferred are electrophilic alkylating agents, sulfonic acid anhydrides, or sulfonic acid halides, more preferred are dimethyl sulfate, methyl triflate, paratoluenesulfonic acid anhydride or trifluoromethanesulfonic acid anhydride, paratoluenesulfonyl chloride, trifluoromethanesulfonyl chloride, and even more preferred are methyl triflate or trifluoromethanesulfonic acid anhydride.

[0093] The reaction of compound (M) with compound (b-2) is preferably carried out further in the presence of a base. Examples of the base include the same bases that can be used in the reaction of at least one compound selected from the group consisting of compounds (M1-2) and (M1-3) with compound (M1-1), and are preferably metal alkoxides, metal hydroxides, metal hydrides, metal carbonates, organolithium compounds, metal amide compounds, amine compounds, or metal carboxylates, and examples thereof include potassium ethoxide, sodium tert-butoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium hydride, lithium aluminum hydride, sodium carbonate, sodium bicarbonate, potassium carbonate, and potassium bicarbonate. More preferred are lithium, methyllithium, normal butyllithium, tertiary butyllithium, lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, lithium tetramethylpiperidide, pyridine, 2,6-dimethylpyridine, 2,6-ditertiary butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, sodium acetate, sodium formate, and ammonium acetate.

[0094] The reaction of compound (M) with compound (b-2) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents that can be used in the reaction of at least one compound selected from the group consisting of compounds (M1-2) and (M1-3) with compound (M1-1). The solvent is preferably acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide, or dimethylacetamide. The solvent is preferably a dehydrated solvent.

[0095] The reaction of compound (M) with compound (b-2) is carried out by mixing a catalyst, compound (M), and compound (b-2), and is preferably carried out by mixing a catalyst, a base, compound (M), and compound (b-2). The reaction between compound (M) and compound (b-2) is preferably carried out in an oxygen-free atmosphere (for example, in a nitrogen atmosphere).

[0096] The amount of compound (b-2) used is usually 0.01 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of compound (M). The amount of the catalyst used is usually 0.001 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of compound (M). The amount of the base used is usually 0.001 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of compound (M). The reaction time of the compound (M) and the compound (b-2) is usually 0.1 to 200 hours. The reaction temperature of the compound (M) and the compound (b-2) is usually -100 to 200°C.

[0097] <Compound (M)> Compound (M) is a novel compound having a structure represented by the following formula, and is a synthetic intermediate of compound (I). [ka] [In the formula, ring W1 , Tamaki W 2 , R 1 and R 2 has the same meaning as above.]

[0098] Examples of the compound (M) include the compounds described below. [ka]

[0099] <Method for producing compound (M)> Compound (M) can be produced by reacting a compound represented by formula (M1-4) (hereinafter sometimes referred to as compound (M1-4)) with at least one compound selected from the group consisting of compound (M1-2) and formula (M1-3). [ka] [In the formula, ring W 1 , Tamaki W 2 , R 1 , R 2 , R 1’ , R 2’ , E1 and E2 have the same meanings as above.] Examples of the leaving group represented by E2 include the same leaving groups as those represented by E1.

[0100] The reaction of compound (M1-4) with at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) is preferably carried out in the presence of a base. Examples of the base include the same bases that can be used in the reaction of at least one compound selected from the group consisting of compounds (M1-2) and (M1-3) with compound (M1-1), and are preferably metal alkoxides, metal hydroxides, metal hydrides, metal carbonates, organolithium compounds, metal amide compounds, amine compounds, or metal carboxylates, and examples thereof include potassium ethoxide, sodium tert-butoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium hydride, lithium aluminum hydride, sodium carbonate, sodium bicarbonate, potassium carbonate, and potassium bicarbonate. More preferred are lithium, methyllithium, normal butyllithium, tertiary butyllithium, lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, lithium tetramethylpiperidide, pyridine, 2,6-dimethylpyridine, 2,6-ditertiary butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, sodium acetate, sodium formate, and ammonium acetate. The amount of the base used is usually 0.001 to 20 mol, and preferably 0.1 to 10 mol, per 1 mol of compound (M1-4).

[0101] The reaction of compound (M1-4) with at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents that can be used in the reaction of at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1). Preferred solvents include acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide, and dimethylacetamide. The solvent is preferably a dehydrated solvent.

[0102] The reaction of compound (M1-4) with at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) is carried out by mixing compound (M1-4) with at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3), and is preferably carried out by mixing a base, compound (M1-4), and at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3). The reaction of compound (M1-4) with at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) is preferably carried out in a deoxygenated atmosphere (e.g., a nitrogen atmosphere).

[0103] The amount of compound (M1-2) used is usually 0.1 to 20 mol, preferably 0.5 to 10 mol, per 1 mol of compound (M1-4). The amount of compound (M1-3) used is usually 0.1 to 20 mol, preferably 0.5 to 10 mol, per 1 mol of compound (M1-4). The amount of the base used is usually 0.001 to 20 mol, and preferably 0.1 to 10 mol, per 1 mol of compound (M1-4). The reaction time of the compound (M1-4) with at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) is usually 0.1 to 200 hours. The reaction temperature of the compound (M1-4) with at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) is usually -100 to 200°C.

[0104] <Composition containing compound (I)> The present invention also includes a composition containing compound (I). A molded article molded from a composition containing compound (I) preferably has a transmittance at the maximum absorption wavelength [nm] of compound (I) contained therein of 50% or less, more preferably 30% or less, even more preferably 15% or less, and particularly preferably 10% or less. The composition containing compound (I) is preferably a resin composition containing compound (I) and a resin (hereinafter, sometimes referred to as a "resin composition"), or a composition containing compound (I) and a polymerizable monomer (hereinafter, sometimes referred to as a "composition (1)").

[0105] The composition containing compound (I) can be used for all purposes, 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 residences, facilities, transport equipment, etc.; window films for residences, facilities, transport equipment, etc.; interior and exterior materials and interior and exterior paints for residences, 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; light source components that emit ultraviolet rays such as fluorescent lamps and mercury lamps; precision machinery, electronic and electrical equipment components, blocking materials for electromagnetic waves generated from 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.

[0106] The shape of the molded article formed from the composition of the present invention may be any of a flat film, powder, spherical particles, crushed particles, a continuous block, fiber, tube, hollow fiber, granule, plate, porous, and the like.

[0107] Examples of resins used in the resin composition include thermoplastic resins and thermosetting resins that have been conventionally used in the production of various known molded articles, sheets, films, and the like. 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.

[0108] Examples of thermosetting resins include epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, and thermosetting polyimide resins.

[0109] When the resin composition is used as an ultraviolet absorbing filter or an ultraviolet absorbing film, the resin is preferably a transparent resin.

[0110] The resin composition can be obtained by mixing Compound (I) with a resin. Compound (I) may be contained in an amount necessary to impart the desired performance, for example, 0.00001 to 99 parts by mass per 100 parts by mass of the resin. The resin composition may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, and an inorganic filler, as needed.

[0111] The polymerizable monomer used in the composition (1) is not particularly limited, but is preferably a radically polymerizable monomer, more preferably a photoradical polymerizable monomer, and even more preferably a (meth)acrylate. Examples of (meth)acrylates include monofunctional (meth)acrylate monomers having one (meth)acryloyloxy group in the molecule, bifunctional (meth)acrylate monomers having two (meth)acryloyloxy groups in the molecule, and polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule. The composition (1) preferably further contains a polymerization initiator. When the polymerizable monomer is a radical polymerizable monomer, the polymerization initiator is preferably a radical polymerization initiator, and more preferably a photopolymerization initiator. Composition (1) can be obtained by mixing compound (I) with a polymerizable monomer. Compound (I) 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 polymerizable monomer. The composition (1) may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, and an inorganic filler, as required.

[0112] When the composition of the present invention is used in an optical product such as an optical film, it can be applied to, for example, an image display device. When the composition of the present invention is applied to an image display device, the optical layer formed from the composition of the present invention may be applied as any of a film layer, a pressure-sensitive adhesive layer, a coating layer, etc., and is preferably an pressure-sensitive adhesive layer or a coating layer. When the composition of the present invention is used in an optical product, it may consist solely of an optical layer formed from the composition of the present invention, or it may be an optical laminate in which an optical layer formed from the composition of the present invention is laminated with other layers. Examples of other layers include a polarizing film, a retardation film, a thermoplastic resin film, etc. When the optical laminate is a laminate in which the optical layer of the present invention, a pressure-sensitive adhesive layer, and a polarizing film are laminated in this order, the optical layer of the present invention is preferably an optical layer (optical film) formed from the composition of the present invention. When the optical laminate is a laminate in which the optical layer of the present invention, a thermoplastic resin film, a pressure-sensitive adhesive layer, and a polarizing film are laminated in this order, the optical layer of the present invention is preferably an optical layer (coating layer) formed from the composition of the present invention. When the optical laminate is a laminate in which a retardation film, the optical layer of the present invention, and a retardation film are laminated in this order, the optical layer of the present invention is preferably an optical layer (pressure-sensitive adhesive layer) formed from the composition of the present invention.

[0113] <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 (i)) containing a resin (A), a compound (I), a crosslinking agent (B), and a silane compound (C). The pressure-sensitive adhesive composition (i) may further contain a radical-curable component (D), an initiator (E), a light-absorbing compound (F) other than compound (I) (hereinafter sometimes referred to as light-selective absorption compound (F)), an antistatic agent, etc., and preferably contains at least one selected from the group consisting of the radical-curable component (D), the initiator (E), and the light-selective absorption compound (F).

[0114] 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 (i) 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 (i). The glass transition temperature can be measured by a differential scanning calorimeter (DSC).

[0115] Examples of the resin (A) include (meth)acrylic resins, silicone resins, rubber resins, and urethane resins, with (meth)acrylic resins being preferred.

[0116] 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).

[0117] 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 (i). The content of compound (I) is usually 0.01 to 20 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 resin (A).

[0118] Examples of the crosslinking agent (B) include an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent, an aziridine-based crosslinking agent, and a metal chelate-based crosslinking agent. 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., an isocyanate-based crosslinking agent is preferred. The content of the crosslinking agent (B) 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).

[0119] Examples of the silane compound (C) 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 (C) may be a silicone oligomer. The content of the silane compound (C) 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).

[0120] 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 (i) may contain two or more types of radically curable components (D).

[0121] Examples of (meth)acrylate compounds include (meth)acrylate monomers and (meth)acrylamide monomers having at least one (meth)acryloyloxy group in the molecule, and (meth)acryl oligomers having at least two (meth)acryloyl groups in the molecule, and other (meth)acryl 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.

[0122] 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.

[0123] 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).

[0124] The initiator (E) 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.

[0125] 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).

[0126] The initiator (E) is preferably selected from those suitable for the polymerization reaction of the radically curable component (D) described above, 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.

[0127] The content of the initiator (E) 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).

[0128] The light-selective absorbing compound (F) is a light-absorbing compound other than compound (I), 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), a compound (dye) that absorbs light in the range of 380 to 780 nm, or a compound (infrared absorber) that absorbs light in the range of 780 to 1500 nm. The structure of the ultraviolet absorber 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 (F) 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).

[0129] The optical layer of the present invention and the optical laminate including the optical layer can be laminated on a display element such as an organic EL element or a liquid crystal cell and used in an image display device (FPD: flat panel display) such as an organic EL display device or a liquid crystal display device. [Example]

[0130] 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.

[0131] (Example 1) Synthesis of compound represented by formula (1) [ka] A 300 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 7 parts of 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one, 70 parts of ethanol, 2.4 parts of potassium hydroxide, and 6.2 parts of malononitrile were added, followed by heating and stirring under reflux at 80°C for 3 hours. To the resulting mixture, 62 parts of ethanol, 6.2 parts of malononitrile, and 4.8 parts of potassium hydroxide were added, followed by heating and stirring under reflux at 80°C for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was then purified to obtain 6.9 parts of a compound represented by formula (a1). [ka] A 20 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen and charged with 1.5 parts of the compound represented by formula (a1), 1.0 part of paratoluenesulfonyl cyanide, 0.3 parts of potassium hydroxide, and 10 parts of ethanol, followed by heating under reflux and stirring for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.7 parts of the compound represented by formula (1).

[0132] LC-MS measurement and 1 H-NMR analysis confirmed the formation of the compound represented by formula (1), and energy dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium cations. 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.21-1.40 (m, 2H), 1.84-1.99 (m, 2H), 2.33-2.76 (m, 5H), 6.38 (s, 1H) LC-MS; [M] - =284.2

[0133] <Measurement of maximum absorption wavelength and gram absorption coefficient ε> The resulting 2-butanone solution (0.003 g / L) of the compound represented by formula (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 1 nm steps over the wavelength range of 300 to 800 nm 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 (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 (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 (m) of the quartz cell.) The maximum absorption wavelength of the compound represented by formula (1) was 518 nm, and the ε (λmax) of the compound represented by formula (1) was 444 L / (g cm).

[0134] <Measurement of full width at half maximum of compound> The resulting 2-butanone solution (concentration: 0.003 g / L) of the compound represented by formula (1) was placed in a 1 cm quartz cell, which was then placed in a UV-2450 spectrophotometer (Shimadzu Corporation). The absorbance was measured in 1 nm steps over the wavelength range of 300 to 800 nm using the double beam method. Two wavelengths were identified that provided half the absorbance of the maximum absorption wavelength. The full width at half maximum (FWHM) was calculated by subtracting the shorter wavelength from the longer wavelength. The FWHM of the compound represented by formula (1) was 26 nm.

[0135] (Example 2) Synthesis of compound represented by formula (M-2) [ka] A 500 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 25 parts of the compound represented by formula (M-1) (7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one), 150 parts of ethanol, 10.3 parts of potassium hydroxide, and 33.11 parts of paratoluenesulfonyl cyanide were added and stirred in an ice bath for 4 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 17.4 parts of the compound represented by formula (M-2).

[0136] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (M-2) was produced. 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.49-1.65 (m, 2H), 1.91-2.00 (m, 2H), 2.30-2.67 (m, 5H), 5.89 (s, 1H) LC-MS; [M] = 188.1

[0137] (Example 3) Synthesis of compound represented by formula (M-3) [ka] A 300 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 5 parts of the compound represented by formula (M-2), 100 parts of dehydrated acetonitrile, 4.4 parts of diisopropylethylamine, and 9 parts of trifluoromethanesulfonic anhydride were added and stirred in an ice bath for 10 minutes. 2.1 parts of malononitrile and 4.4 parts of diisopropylethylamine were added to the resulting mixture and stirred for an additional 30 minutes. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 5.4 parts of the compound represented by formula (M-3).

[0138] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (M-3) was produced. 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.14-1.54 (m, 2H), 1.87-1.99 (m, 2H), 2.22-2.68 (m, 5H), 6.08 (s, 1H) LC-MS; [M]=236.3

[0139] (Example 4) Synthesis of compound represented by formula (1) [ka] A 100 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 2 parts of the compound represented by formula (M-3), 20 parts of dehydrated methyl ethyl ketone, 1.2 parts of potassium carbonate, and 2.8 parts of methyl trifluoromethanesulfonate were mixed and stirred in an ice bath for 2 hours. 0.7 parts of malononitrile and 1.4 parts of diisopropylethylamine were added to the resulting mixture, and the mixture was stirred for an additional 30 minutes. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 1.4 parts of the compound represented by formula (1).

[0140] LC-MS measurement and 1 H-NMR analysis confirmed the formation of the compound represented by formula (1), and energy dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium cations. 1H-NMR (deuterated dimethyl sulfoxide) δ: 1.21-1.40 (m, 2H), 1.84-1.99 (m, 2H), 2.33-2.76 (m, 5H), 6.38 (s, 1H) LC-MS; [M] - =284.2

[0141] (Example 5) Synthesis of compound represented by formula (2) [ka] A 50 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 0.5 parts of the compound represented by formula (a1), 5 parts of dehydrated acetonitrile, 0.3 parts of diisopropylethylamine, and 0.7 parts of N-(trifluoromethylthio)saccharin were added and stirred in an ice bath for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.4 parts of the compound represented by formula (2).

[0142] LC-MS measurement and 1 H-NMR analysis confirmed the formation of the compound represented by formula (2). Energy-dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium cations. Furthermore, the maximum absorption wavelength, gram absorption coefficient, and full width at half maximum were measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (2) was 526 nm, the gram absorption coefficient ε (λmax) at the maximum absorption wavelength was 189 L / (g·cm), and the full width at half maximum was 26 nm. 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.16-1.19 (m, 2H), 1.33-1.36 (m, 2H), 1.91-1.99 (m, 5H), 6.88-6.91 (m, 1H) LC-MS; [M] - =359.4

[0143] (Example 6) Synthesis of compound represented by formula (3) [ka] A 20 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 0.5 parts of the compound represented by formula (a1), 5 parts of dehydrated acetonitrile, and 0.3 parts of N-chlorosuccinimide were added and stirred in an ice bath for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.4 parts of the compound represented by formula (3).

[0144] LC-MS analysis confirmed the formation of the compound represented by formula (3). Energy-dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium cations. Furthermore, the maximum absorption wavelength, gram absorption coefficient, and full width at half maximum were measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (3) was 551 nm, the gram absorption coefficient ε (λmax) at the maximum absorption wavelength was 130 L / (g cm), and the full width at half maximum was 28 nm. LC-MS; [M] - =293.5

[0145] (Example 7) Synthesis of compound represented by formula (4) [ka] A 20 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 0.5 parts of the compound represented by formula (a1), 5 parts of dehydrated dimethylformamide, and 0.5 parts of N-chlorosuccinimide were added and stirred in an ice bath for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.4 parts of the compound represented by formula (4).

[0146] LC-MS measurement and 1 H-NMR analysis confirmed the formation of the compound represented by formula (4). Energy-dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium cations. Furthermore, the maximum absorption wavelength, gram absorption coefficient, and full width at half maximum were measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (4) was 572 nm, the gram absorption coefficient ε (λmax) at the maximum absorption wavelength was 126 L / (g cm), and the full width at half maximum was 44 nm. LC-MS; [M] - =328.2 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.24-1.25 (m, 2H), 1.88-2.33 (m, 7H)

[0147] (Example 8) Synthesis of compound represented by formula (5) [ka] A 20 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 1 part of the compound represented by formula (a1), 10 parts of dehydrated dimethylformamide, and 0.7 parts of N-bromosuccinimide were added and stirred in an ice bath for 3 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.7 parts of the compound represented by formula (5).

[0148] LC-MS measurement and 1 H-NMR analysis confirmed the formation of the compound represented by formula (5). Energy-dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium cations. Furthermore, the maximum absorption wavelength, gram absorption coefficient, and full width at half maximum were measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (5) was 548 nm, the gram absorption coefficient ε (λmax) at the maximum absorption wavelength was 180 L / (g cm), and the full width at half maximum was 26 nm. LC-MS; [M] - =338.2 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.31-1.37 (m, 2H), 1.82-1.99 (m, 2H), 2.43-2.79 (m, 5H), 6.46 (s, 1H)

[0149] (Example 9) Synthesis of compound represented by formula (M-4) [ka] A 100 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 5 parts of the compound represented by formula (M-2), 50 parts of dehydrated acetonitrile, and 0.7 parts of sodium hydride were added and stirred in an ice bath for 30 minutes. 9.6 parts of paratoluenesulfonyl cyanide was added to the resulting mixture and stirred at 50°C for 4 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 3.8 parts of the compound represented by formula (M-4).

[0150] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (M-4) was produced. LC-MS; [M] - =213.1 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.46-1.57 (m, 2H), 1.82-1.91 (m, 2H), 2.16-2.39 (m, 5H)

[0151] (Example 10) Synthesis of compound represented by formula (6) [ka] A 200 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 4.5 parts of the compound represented by formula (M-4), 68 parts of dehydrated acetonitrile, and 0.6 parts of sodium hydride were added and stirred in an ice bath for 30 minutes. 7.1 parts of trifluoromethanesulfonic anhydride were added to the resulting mixture and stirred in an ice bath for 30 minutes, followed by addition of 1.7 parts of malononitrile and 3.5 parts of potassium carbonate and stirring at 50°C for 2 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 2.1 parts of the compound represented by formula (M-5). [ka] A 300 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 1.2 parts of the compound represented by formula (M-5), 36 parts of acetonitrile, 8.8 parts of di-tert-butylpyridine, 7.5 parts of paratoluenesulfonic anhydride, and 1.5 parts of malononitrile were mixed and stirred in an ice bath for 24 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified to obtain 0.4 parts of the compound represented by formula (6). The potassium ions in the compound represented by formula (6) were derived from the potassium bicarbonate used during purification.

[0152] LC-MS measurement and 1 H-NMR analysis confirmed the generation of an anion in the compound represented by formula (6), and energy dispersive X-ray spectroscopy (SEM-EDX analysis) confirmed the presence of potassium atoms (potassium cations). Furthermore, the maximum absorption wavelength, gram absorption coefficient, and full width at half maximum were measured in the same manner as above. The maximum absorption wavelength of the compound represented by formula (6) was 511 nm, the gram absorption coefficient ε (λmax) at the maximum absorption wavelength was 211 L / (g·cm), and the full width at half maximum was 29 nm. LC-MS; [M] - =309.3 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.16-1.21 (m, 2H), 1.30-1.37 (m, 2H), 1.62-1.65 (m, 2H), 1.88-1.91 (m, 3H)

[0153] <Preparation of acrylic resin> Polymerization Example 1: Preparation of acrylic resin (A1) 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 addition of the polymerization initiator, 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 1.4 million as measured by GPC in terms of polystyrene, and an Mw / Mn ratio of 5.5, which was designated as acrylic resin (A1).

[0154] Polymerization Example 2: Preparation of acrylic resin (A2) A reaction vessel equipped with a condenser, nitrogen inlet, thermometer, and stirrer was charged with a mixture of 81.8 parts ethyl acetate as solvent, 60 parts methyl acrylate, 10 parts acrylic acid, 10 parts 2-hydroxyethylmethyl acrylate, and 20 parts 2-phenoxyethyl acrylate. 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 addition of the polymerization initiator, the temperature was maintained 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 reaction vessel was then maintained at this temperature for 12 hours. 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 920,000 as determined by GPC in terms of polystyrene, and an Mw / Mn ratio of 4.7, which was designated as acrylic resin (A2).

[0155] (Example 11) Preparation of resin composition (1) (adhesive composition (1)) <Preparation of Resin Composition (1)> 100 parts of a solids solution of acrylic resin (A1) in ethyl acetate (resin concentration: 20%) was mixed with 0.5 parts of a crosslinker (manufactured by Tosoh Corporation: trade name "Coronate L", an isocyanate-based compound, solids content 75%), 0.28 parts of a silane compound (manufactured by Shin-Etsu Chemical Co., Ltd.: trade name "KBM3066"), and 1.5 parts of the compound represented by formula (1), and 2-butanone was added to give a solids concentration of 14%, to obtain resin composition (1) (adhesive composition (1)). Note that the amount of the crosslinker is the number of parts by mass of the active ingredient.

[0156] (Examples 12 to 18, Comparative Example 1) Preparation of resin compositions (2) to (9) Pressure-sensitive adhesive compositions (2) to (9) were prepared in the same manner as in Example 11, except that the components and the amounts of the components were changed as shown in Table 7. The blending amount of the crosslinking agent is the number of parts by mass as the active ingredient, and the blending amount of the resin (A) is the number of parts by mass of the solid content.

[0157] [Table 7]

[0158] The abbreviations in Table 7 have the following meanings: Acrylic resin (A1): Acrylic resin (A1) synthesized in Polymerization Example 1 Acrylic resin (A2): Acrylic resin (A2) synthesized in Polymerization Example 2 Formula (1): Compound represented by formula (1) synthesized in Example 1 or Example 4 Formula (6): Compound represented by formula (6) synthesized in Example 10 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 A-DPH-12E: Product name: A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd., hexafunctional (meth)acrylate compound NCI-730: ADEKA Corporation, product name: NCI-730, a photoradical generator that is an oxime ester compound RUV-93: Benzotriazole-based UV absorber manufactured by Otsuka Chemical Co., Ltd., product name: RUVA-93, maximum absorption wavelength λmax = 337 nm Formula (B): A compound represented by the following formula (B) (3-butyl-2-[3-(-3-butyl-5-phenyl-2(3H)-benzolylidene)-1-propen-1-yl]-5-phenyl-benzoxazolium p-toluenesulfonate) synthesized with reference to the specification of U.S. Pat. No. 6,004,536. The full width at half maximum measured in the same manner as above was 44 nm. [ka]

[0159] <Evaluation of Molded Article of Resin Composition (1)> [Production of resin molded body (1)] The obtained resin composition (1) (adhesive composition (1)) was applied using an applicator to the release-treated surface of a release-treated polyethylene terephthalate film (trade name "PLR-382190" obtained from Lintec Corporation) and dried at 100°C for 1 minute to form a resin molded body (adhesive layer) (1), thereby producing a resin molded body (1) with a separate film. The thickness of the obtained resin molded body (1) was 15 µm.

[0160] The obtained resin molded body (1) with a separate film was laminated to a 23 μm ultraviolet absorber-containing cycloolefin film (trade name "ZEONOR" available from 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 a laminate (1-1) having a laminated structure of cycloolefin film / resin molded body (1) / separate film.

[0161] [Measurement of absorbance of resin molded body (1)] The resulting laminate (1-1) was cut into a size of 30 mm x 30 mm, the separate film was peeled off, and the resin molded body (1) was laminated with alkali-free glass (trade name "EAGLE XG" manufactured by Corning Incorporated), which was used as sample (1). The absorbance of the prepared sample (1) in the wavelength range of 300 to 800 nm was measured in 1 nm increments using a spectrophotometer (UV-2450, manufactured by Shimadzu Corporation). The measured absorbance at a wavelength of 330 nm was taken as the absorbance of the resin molded body (1) at a wavelength of 330 nm. The absorbance of the alkali-free glass alone and the cycloolefin film alone at a wavelength of 330 nm was 0. The transmittance at a wavelength of 330 nm was calculated using the following formula: The results are shown in the transmittance column of Table 8. T=10 -A ×100 (T represents transmittance, and A represents absorbance.)

[0162] The maximum absorption wavelength of sample (1) was determined from the absorbance measured above, and the absorbance at the determined maximum absorption wavelength was defined as the absorbance at the maximum absorption wavelength of resin molded product (1). Note that the absorbance at the maximum absorption wavelength of each of the alkali-free glass alone and the cycloolefin film alone was 0. The transmittance (%) of the maximum absorption wavelength was calculated based on the following formula: The results are shown in Table 9. T1=10 -A1 ×100 (T1 represents the transmittance at the maximum absorption wavelength, and A1 represents the absorbance at the maximum absorption wavelength.)

[0163] [Evaluation of Bleeding Resistance of Resin Molded Product (1)] A separate film was further laminated on one side of the obtained resin molded article (1) with a separate film to obtain a pressure-sensitive adhesive layer (1) with double-sided separate films. The obtained pressure-sensitive adhesive layer (1) with double-sided separate films was stored in air at 23 to 25°C for one month. After storage, the pressure-sensitive adhesive layer (1) 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 a, and if crystalline precipitation was observed, it was marked b. The evaluation results are shown in the column for bleed resistance in Table 8.

[0164] [Measurement of absorbance retention of resin molded product (1)] A polarizing plate was prepared in which a 13 μm thick cycloolefin film was attached to one surface of an 8 μm thick polarizer using an adhesive layer. The resin molding (1) side of the resin molding (1) with a separate film was attached to the polarizer side of the polarizing plate using a laminator, and then aged for 7 days under conditions of a temperature of 23°C and a relative humidity of 65% to obtain a laminate having a laminate structure of cycloolefin film / polarizer / resin molding (1) / separate film. The obtained laminate was cut into a size of 30 cm x 30 cm, the separate film was peeled off, and the resin molded body (1) and alkali-free glass (trade name "EAGLE XG" manufactured by Corning Incorporated) were bonded together to obtain a laminated body (1-2) having a laminated structure of cycloolefin film / polarizer / resin molded body (1) / glass. The obtained laminate (1-2) was placed in a Sunshine Weather Meter (manufactured by Suga Test Instruments Co., Ltd.) for 75 hours under conditions of a temperature of 63°C and a relative humidity of 50% RH, and a weather resistance test was performed. The absorbance of the removed laminate (1-2) was measured in the same manner as above. From the measured absorbance, the absorbance retention [%] of the laminate (1-2) at a wavelength of 540 nm was calculated based on the following formula. The results are shown in Table 8. The closer the absorbance retention is to 100%, the less deterioration of the light-selective absorption function and the better the weather resistance. The absorption wavelength for evaluating the absorbance retention was selected from the measured absorbances at wavelengths longer than the maximum absorption wavelength, where the absorbance was 1 to 1.5, because this wavelength is the absorbance region with the highest sensitivity in terms of measurement accuracy of the spectrometer. Absorbance retention rate (%) = (A(540) after durability test / A(540) before durability test) × 100 [A(540) represents the absorbance of the laminate (1-2) at a wavelength of 540 nm.]

[0165] Resin composition (2) was used instead of resin composition (1) to prepare resin molded product (2), laminate (2-1) and laminate (2-2), which were evaluated in the same manner. The results are shown in Table 8.

[0166] Resin composition (3) was used instead of resin composition (1) to prepare resin molded product (3), laminate (3-1) and laminate (3-2), which were similarly evaluated. The results are shown in Table 8.

[0167] Resin composition (5) was used instead of resin composition (1) to prepare a resin molded body (5) having a thickness of 20 μm. Laminates (5-1) and (5-2) were prepared in the same manner except that resin molded body (5) was used instead of resin molded body (1), and bleed resistance and absorbance retention were evaluated. The absorbance retention was evaluated at a wavelength of 520 nm. The results are shown in Table 8.

[0168] Resin composition (6) was used instead of resin composition (1) to prepare a resin molded body (6) having a thickness of 20 μm. Laminates (6-1) and (6-2) were prepared in the same manner except that resin molded body (6) was used instead of resin molded body (1), and bleed resistance and absorbance retention were evaluated. The absorbance retention was evaluated at a wavelength of 530 nm. The results are shown in Table 8.

[0169] Resin composition (7) was used instead of resin composition (1) to prepare a resin molded product (7) having a thickness of 20 μm. Laminates (7-1) and (7-2) were prepared in the same manner except that resin molded product (7) was used instead of resin molded product (1), and bleed resistance and absorbance retention were evaluated. The absorbance retention was evaluated at a wavelength of 520 nm. The results are shown in Table 8.

[0170] Resin composition (8) was used instead of resin composition (1) to prepare a resin molded body (8) having a thickness of 20 μm. Laminates (8-1) and (8-2) were prepared in the same manner except that resin molded body (8) was used instead of resin molded body (1), and bleed resistance and absorbance retention were evaluated. The absorbance retention was evaluated at a wavelength of 520 nm. The results are shown in Table 8.

[0171] Resin composition (9) was used instead of resin composition (1) to prepare a resin molded body (9) having a thickness of 20 μm. Laminates (9-1) and (9-2) were prepared in the same manner except that resin molded body (9) was used instead of resin molded body (1), and bleed resistance and absorbance retention were evaluated. The absorbance retention was evaluated at a wavelength of 510 nm. The results are shown in Table 8.

[0172] <Evaluation of Molded Article of Resin Composition (4)> [Preparation of resin molded body (4)] Resin composition (4) was applied to the release-treated surface of a release-treated polyethylene terephthalate film (trade name "PLR-382190" available from Lintec Corporation) using an applicator to a dry thickness of 5 μm, and then dried at 100°C for 1 minute. Subsequently, a resin molded body (adhesive layer) (4) was formed by irradiating the resin molded body (4) with a separate film using an ultraviolet irradiation device ("Electrodeless UV Lamp System H Bulb" manufactured by Fusion UV Systems) with UV-A (wavelength 320-390 nm) adjusted to an illuminance of 500 mW and an integrated light amount of 500 mJ from the separate film side. The obtained resin molded body (4) with a separate film was laminated to alkali-free glass, and after peeling off the separate film, a 23 μm ultraviolet absorber-containing cycloolefin film (trade name "ZEONOR" available from Zeon Corporation) was laminated to the resin molded body (4) to produce a laminated body (4-1) having a laminated structure of cycloolefin film / resin molded body (4) / glass. The prepared laminate (4-1) was set in a spectrophotometer UV-2450 (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 measured absorbance at a wavelength of 330 nm was taken as the absorbance of the resin molded product (4) at a wavelength of 330 nm. Note that the absorbance at a wavelength of 330 nm was 0 for both the alkali-free glass alone and the cycloolefin film. The transmittance (%) at a wavelength of 330 nm was calculated based on the following formula: The results are shown in Table 8. T=10 -A ×100 (T represents transmittance, and A represents absorbance.)

[0173] The maximum absorption wavelength of the laminate (4-1) was determined from the absorbance measured above, and the absorbance at the determined maximum absorption wavelength was taken as the absorbance at the maximum absorption wavelength of the resin molded product (4). Note that the absorbance at the maximum absorption wavelength of each of the alkali-free glass alone and the cycloolefin film alone was 0. The transmittance (%) of the maximum absorption wavelength was calculated based on the following formula: The results are shown in Table 9. T1=10 -A1 ×100 (T1 represents the transmittance at the maximum absorption wavelength, and A1 represents the absorbance at the maximum absorption wavelength.)

[0174] [Evaluation of Bleeding Resistance of Resin Molded Product (4)] A separate film was further laminated on one side of the obtained resin molded article (4) with a separate film to obtain a pressure-sensitive adhesive layer (4) with double-sided separate films. The obtained pressure-sensitive adhesive layer (4) with double-sided separate films was stored in air at 23 to 25°C for one month. After storage, the pressure-sensitive adhesive layer (4) 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 a, and if crystalline precipitation was observed, it was marked b. The evaluation results are shown in the column for bleed resistance in Table 8.

[0175] [Measurement of absorbance retention of resin molded product (4)] A polarizing plate was prepared in which a 13 μm thick cycloolefin film was attached to one surface of an 8 μm thick polarizer using an adhesive layer. The resin molding (4) side of the resin molding (4) with a separate film was attached to the polarizer side of the polarizing plate using a laminator, and then aged for 7 days under conditions of a temperature of 23°C and a relative humidity of 65% to obtain a laminate having a laminate structure of cycloolefin film / polarizer / resin molding (4) / separate film. The separate film was peeled off from the obtained laminate, and the resin molded body (4) was bonded to alkali-free glass (trade name "EAGLE XG" manufactured by Corning Incorporated) to obtain a laminated body (4-2) having a laminated structure of cycloolefin film / polarizer / resin molded body (4) / glass. The obtained laminate (4-2) was placed in a Sunshine Weather Meter (manufactured by Suga Test Instruments Co., Ltd.) for 75 hours under conditions of a temperature of 63°C and a relative humidity of 50% RH, and a weather resistance test was performed. The absorbance of the removed laminate (4-2) was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 540 nm was calculated based on the following formula. The results are shown in Table 8. The closer the absorbance retention is to 100%, the less deterioration of the light-selective absorption function and the better the weather resistance. Absorbance retention rate (%) = (A(540) after durability test / A(540) before durability test) × 100 [A(540) represents the absorbance of the laminate (4-2) at a wavelength of 540 nm.]

[0176] [Table 8]

[0177] [Table 9]

[0178] The transmittance values ​​at the maximum absorption wavelengths of Examples 11 to 13 indicate that they exceeded the measurement limit of absorbance (absorbance: 5) by a spectrophotometer.

[0179] The compound of the present invention has high absorption selectivity for light having a wavelength near the maximum absorption wavelength. Furthermore, a resin composition containing the compound of the present invention has high absorbance retention even after a weathering test, and has good weather resistance.

Claims

1. A compound having an anion represented by the following formula (IA): 【Chemistry 1】 [In formula (IA), R １ and R ２ each independently represents a hydrogen atom or an electron-withdrawing group, R １ and R ２ At least one of the groups has the electron-withdrawing group. The electron-withdrawing group is a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -CO-NR 3 R 3z (R 3 and R 3z each independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, or a group represented by formula (z-1). 【Chemistry 2】 [In formula (z-1), R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group. X 1 represents —CO—, —COO—, —OCO—, —CS—, —CSS—, —COS—, —CSO—, —SO 2 —, —NR 223 CO— or —CONR 224 —. R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * represents a bond. R ３ , R ４ , R ５ and R ６ each independently represent a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, —CO—R 1 , —CO—O—R 2 , —CO—NR 3 R 3z , —CO-S—R 4 , —CS-R 5 , —CS-O—R 6 , —CS-S—R 7 , —SO-R 8 , —SO 2 —R 9 (R 1 , R 2 , R 3 , R 3z , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom), —OCF 3 , —SCF 3 , —SF 5 , —SF 3 , —SO 2 H or —SO 3 H.]

2. R １ and R ２ At least one selected from the group consisting of a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -CO-R １ , —CO—O—R ２ , —CO—NR ３ R ３ｚ , -CO-S-R ４ , -CS-R ５ , -CS-O-R ６ , -CS-S-R ７ , -SO-R ８ , -SO ２ -R ９ (R １ , R ２ , R ３ , R ３ｚ , R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a hydrocarbon group which may have a substituent or a halogen atom), —OCF ３ , -SCF ３ , -SF ５ , -SF ３ , -SO ２ H or -SO ３ The compound of claim 1 wherein H.

3. A compound described in claim 1 or 2, wherein at least one selected from R 1 and R 2 is a cyano group, a nitro group, -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, -CO-R 1 , -CO-O-R 2 , or -SO 2 -R 9 (R 1 , R 2 , and R 9 each independently represent a hydrocarbon group or a halogen atom which may have a substituent).

4. R ３ , R ４ , R ５ and R ６ The compound according to any one of claims 1 to 3, wherein each independently represents a cyano group, a nitro group, -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, -CO-R 1 , -CO-O-R 2 , or -SO 2 -R 9.

5. R ３ , R ４ , R ５ and R ６ are each independently a cyano group, a nitro group, —OCF 3 , —SCF 3 , —SF 5 , —SO 2 CF 3 , or —SO 2 —R 10 (R 10 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent).

6. R ３ , R ４ , R ５ and R ６ and each independently represent a cyano group or a nitro group.

7. The compound according to any one of claims 1 to 6, which exhibits a maximum absorption in the wavelength range of 400 nm to 700 nm.

8. The compound according to any one of claims 1 to 7, which has a gram absorption coefficient at the maximum absorption wavelength of 50 [L / (g cm)] or more.

9. A resin composition comprising the compound according to any one of claims 1 to 8 and a resin.

10. A composition comprising the compound according to any one of claims 1 to 8 and a polymerizable monomer.

11. A molded article molded from the resin composition according to claim 9 or the composition according to claim 10.

12. An optical layer comprising the resin composition according to claim 9 or the composition according to claim 10.

13. An optical laminate comprising the optical layer according to claim 12.

14. An image display device comprising the optical laminate according to claim 13.

15. Formula (M-A-1) 【Transformation 3】 [In formula (M-A-1), R １ and R ２ each independently represents a hydrogen atom or an electron-withdrawing group, R １ and R ２ At least one of the groups has the electron-withdrawing group. The electron-withdrawing group is a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -CO-NR 3 R 3z (R 3 and R 3z each independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, or a group represented by formula (z-1). 【Chemistry 4】 [In formula (z-1), R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group. X 1 represents —CO—, —COO—, —OCO—, —CS—, —CSS—, —COS—, —CSO—, —SO 2 —, —NR 223 CO— or —CONR 224 —. R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * represents a bond. R ３ and R ４ each independently represent a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, —CO—R 1 , —CO—O—R 2 , —CO—NR 3 R 3z , —CO-S—R 4 , —CS-R 5 , —CS-O—R 6 , —CS-S—R 7 , —SO-R 8 , —SO 2 —R 9 (R 1 , R 2 , R 3 , R 3z , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom), —OCF 3 , —SCF 3 , —SF 5 , —SF 3 , —SO 2 H or —SO 3 H.] and a compound represented by formula (b-3) 【Transformation 5】 [In formula (b-3), R ５ and R ６ each independently represents a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, —CO—R 1 , —CO—O—R 2 , —CO—NR 3 R 3z , —CO-S—R 4 , —CS-R 5 , —CS-O—R 6 , —CS-S—R 7 , —SO-R 8 , —SO 2 —R 9 (R 1 , R 2 , R 3 , R 3z , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represents a hydrocarbon group which may have a substituent or a halogen atom), —OCF 3 , —SCF 3 , —SF 5 , —SF 3 , —SO 2 H or —SO 3 H. X ２ represents a divalent linking group. with a compound represented by formula (IA) 【Transformation 6】 [In the formula, R １ , R ２ , R ３ , R ４ , R ５ and R ６ have the same meanings as above.] A method for producing a compound having an anion represented by the formula:

16. Furthermore, in the presence of a catalyst, 【Transformation 7】 [In formula (M-1), R １ and R ２ have the same meanings as above.] and a compound represented by formula (b-2) 【Transformation 8】 [In the formula, R ３ and R ４ have the same meanings as above. X １ represents a divalent linking group. and a compound represented by formula (MA-1) to obtain the compound represented by formula (MA-2).

17. Formula (IA) 【Chemistry 9】 [In formula (IA), R １ and R ２ each independently represents a hydrogen atom or an electron-withdrawing group, R １ and R ２ At least one of the groups has the electron-withdrawing group. R 3 , R 4 , R 5 and R 6 each independently represent a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -CO-R 1 , -CO-O-R 2 , -CO-NR 3 R 3z , -CO-S-R 4 , -CS-R 5 , -CS-O-R 6 , -CS-S-R 7 , -SO-R 8 , -SO 2 -R 9 (R 1 , R 2 , R 3 , R 3z , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 2 H or -SO 3 H. ] A method for producing a compound having an anion represented by Formula (M1-2) 【Chemistry 10】 [In formula (M1-2), R ２’ represents an electron-withdrawing group, E １ represents a leaving group.] and compounds represented by formula (M1-3): 【Chemistry 11】 [In formula (M1-3), R １’ represents an electron-withdrawing group, E ２ represents a leaving group.] and at least one compound selected from compounds represented by formula (M1-1-1): 【Chemistry 12】 [In formula (M1-1-1), R ３ , R ４ , R ５ and R ６ has the same meaning as above.] to produce a compound having an anion represented by formula (IA), The electron-withdrawing groups represented by R 1 , R 2 , R 1' , and R 2' are each independently a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -CO-NR 3 R 3z (R 3 and R 3z each independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, or a group represented by formula (z-1). 【Chemistry 13】 [In formula (z-1), R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group. X 1 represents —CO—, —COO—, —OCO—, —CS—, —CSS—, —COS—, —CSO—, —SO 2 —, —NR 223 CO— or —CONR 224 —. R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * represents a bond.

18. A compound represented by formula (M-1). 【Chemistry 14】 [In formula (M-1), R １ and R ２ each independently represents a hydrogen atom or an electron-withdrawing group, R １ and R ２ At least one of the groups has the electron-withdrawing group. The electron-withdrawing group is a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -CO-NR 3 R 3z (R 3 and R 3z each independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, or a group represented by formula (z-1). 【Chemistry 15】 [In formula (z-1), R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group. X 1 represents —CO—, —COO—, —OCO—, —CS—, —CSS—, —COS—, —CSO—, —SO 2 —, —NR 223 CO— or —CONR 224 —. R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * represents a bond.

19. A compound represented by formula (MA-1). 【Chemistry 16】 [In formula (M-A-1), R １ and R ２ each independently represents a hydrogen atom or an electron-withdrawing group, R １ and R ２ At least one of the groups has the electron-withdrawing group. The electron-withdrawing group is a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -CO-NR 3 R 3z (R 3 and R 3z each independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, or a group represented by formula (z-1). 【Chemistry 17】 [In formula (z-1), R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group. X 1 represents —CO—, —COO—, —OCO—, —CS—, —CSS—, —COS—, —CSO—, —SO 2 —, —NR 223 CO— or —CONR 224 —. R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * represents a bond. R ３ and R ４ each independently represent a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, —CO—R 1 , —CO—O—R 2 , —CO—NR 3 R 3z , —CO-S—R 4 , —CS-R 5 , —CS-O—R 6 , —CS-S—R 7 , —SO-R 8 , —SO 2 —R 9 (R 1 , R 2 , R 3 , R 3z , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a hydrocarbon group which may have a substituent or a halogen atom), —OCF 3 , —SCF 3 , —SF 5 , —SF 3 , —SO 2 H or —SO 3 H.]

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