compound

Abstract

To provide a novel compound that efficiently absorbs light in the visible region and has favorable weather resistance.SOLUTION: The compound has cations comprising a partial structure represented by formula (I) in the figure. [In formula (I), a ring W1 and a ring W2 each independently represent a ring structure having at least one double bond as a constituent of the ring, where the ring W1 and ring W2 each independently may have a substituent; and R1 and R2 each independently represent a hydrogen atom or a monovalent substituent, where at least one of R1 and R2 is a monovalent substituent.]SELECTED DRAWING: None

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 weather resistance). 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., 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 weather resistance), and compounds having good durability have been desired. [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] A compound having a cation containing a partial structure represented by the following formula (I): [ka] [In formula (I), Ring W 1 and Ring W 2 each independently represents a ring structure having at least one double bond as a ring component. Ring W 1 and Ring W 2 may each independently 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 the groups is a monovalent substituent.] [2] R 1 and R 2 The compound according to [1], wherein at least one selected from the following 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 3k , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3k , 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 1 and R 2 The compound according to [3], wherein at least one selected from the group consisting of: is a cyano group. [5] The compound according to any one of [1] to [4], wherein the cation containing the partial structure represented by formula (I) is a cation represented by formula (IA). [ka] [In formula (IA), Ring W 1 , Tamaki W 2 , R 1 and R2 have the same meanings as above. R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom, a heterocyclic group, or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH- or =CH- contained in the hydrocarbon group may be substituted with -O- or -S-. 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. [6] The compound according to [5], wherein the cation represented by formula (IA) is a cation represented by formula (IB) or a cation represented by formula (IC). [ka] [In formula (IB) and formula (IC), Ring W 1 , Tamaki W 2 , R 1 and R 2 have the same meanings as above. Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent. R 4A and R 6A each independently represents a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent. Ring W 3 and Ring W 4 each independently represents a nitrogen-containing heterocyclic group. [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] A resin composition comprising the compound according to any one of [1] to [7] and a resin. [9] A composition comprising the compound according to any one of [1] to [7] and a polymerizable monomer.

[10] A molded article molded from the composition according to [8] or [9].

[11] A dyed product dyed with the compound according to any one of [1] to [7].

[12] An optical layer containing a cation having a partial structure represented by the following formula (I): [ka] [In formula (I), Ring W 1 and Ring W 2 each independently represents a ring structure having at least one double bond as a ring component. Ring W 1 and Ring W 2 may each independently 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 the groups is a monovalent substituent.] [Effects of the Invention]

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

[0007] The compound of the present invention is a compound containing a cation having a partial structure represented by the following formula (I) (hereinafter, sometimes referred to as compound (I)). [ka] [In formula (I), Ring W 1 and Ring W 2 each independently represents a ring structure having at least one double bond as a ring component. Ring W1 and Ring W 2 may each independently 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 the groups is a monovalent substituent.]

[0008] <cation> The cation having the partial structure represented by formula (I) also includes all of the resonance structures shown below. [ka]

[0009] Ring W 1 and Ring W 2 Each independently represents a ring structure having at least one double bond as a ring component. 1 and Ring W 2 has one or more double bonds as ring components, but ring W 1 and Ring W 2 The double bond contained in the formula (I) is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Ring W 1 and Ring W 2 may each independently be a monocyclic ring or a polycyclic ring. 1 and Ring W 2 may each independently be an aromatic ring or a ring without aromaticity (aliphatic ring), but is preferably a ring without aromaticity. If it is a ring without aromaticity, the selective absorption can be further improved. Ring W 1 and Ring W 2 may each independently be a heterocycle containing a heteroatom (for example, a nitrogen atom, an oxygen atom, a sulfur atom, etc.) or a ring made of a hydrocarbon. 1 and Ring W 2 are preferably each independently a ring made of a hydrocarbon. Ring W 1 and Ring W 2 are each independently 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 and Ring W 2 are each preferably independently a monocyclic ring.

[0010] 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 Examples of the fused ring formed by the above include the fused rings shown below: In the following formula, * represents a bond. [ka]

[0011] 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, an n-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; halogenated alkyl groups having 1 to 25 carbon atoms, such as a chloromethyl 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; halogenated 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; alkylthio groups 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; fluorinated alkoxy groups 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; fluorinated alkoxy groups having 1 to 12 carbon atoms, such as a trifluoromethanethioalkoxy group; an amino group, a methylamino group, an ethylamino group, a dimethylamino group, or a methylamino group. an amino group optionally substituted by one or two substituents having 1 to 25 carbon atoms, such as an amino group, a diethylamino group, a diphenylamino group, a piperidino group, a pyrrolidino group, or a methylethyl group; a carbamoyl group optionally substituted at the N-position by 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 Tamaki W 2 The fused ring formed by the ring W may also have a substituent. 1 or Ring W 2 Examples of the substituents that may be possessed by the group include:

[0012] 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.

[0013] R 1 and R 2Examples of the monovalent aliphatic hydrocarbon group represented by the formula (I) include hydrocarbon groups 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 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 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.

[0014] 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 a phenyl group or a benzyl group is more preferred.

[0015] 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.

[0016] 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.

[0017] 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.

[0018] 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.]

[0019] 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.

[0020] 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; and the like, 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:

[0021] R 223 and R 224 Examples of the alkyl group having 1 to 6 carbon atoms represented by the formula (I) include linear or branched alkyl groups having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an n-hexyl group, and a 1-methylbutyl group.

[0022] The group represented by formula (z-1) is -CO-R1, -CO-O-R2, -CO-NR3R 3k , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3k 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.

[0023] R 1 and R 2 At least one selected from the following is preferably 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 3k , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R 3kR4, 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; 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. A cyano group is particularly preferred.

[0024] The cation having the partial structure represented by formula (I) is preferably a cation represented by formula (IA). [ka] [In formula (IA), Ring W 1 , Tamaki W 2 , R 1 and R 2 have the same meanings as above. R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom, a heterocyclic group, or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH- or =CH- contained in the hydrocarbon group may be substituted with -O- or -S-. 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.

[0025] R 3 , R 4 , R 5 and R 6Examples of the hydrocarbon group having 1 to 24 carbon atoms represented by the formula include an aliphatic hydrocarbon group having 1 to 24 carbon atoms and an aromatic hydrocarbon group having 6 to 24 carbon atoms. Examples of the aliphatic hydrocarbon group having 1 to 24 carbon atoms include linear, branched, and cyclic alkyl groups having 1 to 24 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-hexyl-octyl, 4-butyloctyl, and cyclohexyl groups; and unsaturated aliphatic hydrocarbon groups, such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl, and butadienyl groups. Examples of aromatic hydrocarbon groups having 6 to 24 carbon atoms include aryl groups having 6 to 24 carbon atoms such as phenyl, naphthyl, anthracenyl, and biphenyl; and aralkyl groups having 7 to 24 carbon atoms such as benzyl, phenylethyl, and naphthylmethyl. R 3 , R 4 , R 5 and R 6 The -CH2- or =CH- contained in the hydrocarbon group having 1 to 24 carbon atoms represented by the following formula may be substituted with -O- or -S-. For example, examples of the group in which -CH2- or =CH- contained in the hydrocarbon group having 1 to 24 carbon atoms is substituted with -O- include alkoxy groups having 1 to 24 carbon atoms such as a methoxy group, an ethoxy group, and a propoxy group; aryloxy groups having 6 to 18 carbon atoms such as a phenoxy group; -(X) groups including an oxyethylene group (-CH2CHO-), an oxypropyl group (-CH2CH2CHO-), and the like. 12 O) m1 -R 12 A group represented by (X 12 represents an alkylene group having 1 to 6 carbon atoms, and R 12 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, m1 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less. Examples of the group in which -CH2- or =CH- in a hydrocarbon group having 1 to 24 carbon atoms is substituted with -S- include alkylthio groups having 1 to 18 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; arylthio groups having 6 to 18 carbon atoms, such as a phenylthio group; -(X) including a thioethylene group (-CH2CH2S-), a thiopropyl group (-CH2CH2CH2S-), and the like. 13 S) m2 -R 13 A group represented by (X 13 represents an alkylene group having 1 to 6 carbon atoms, and R 13 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, and m2 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less.

[0026] R 3 , R 4 , R 5 and R 6Examples of the substituent that the hydrocarbon group having 1 to 24 carbon atoms represented by the formula (I) may have include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; halogenated alkyl groups having 1 to 25 carbon atoms such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, and a nonafluorobutyl group; and methoxy, ethoxy, propoxy, isopropoxy, and butoxy groups. alkoxy groups having 1 to 25 carbon atoms, such as a tert-butoxy group, a pentyloxy group, a hexyloxy group, a 2-ethylhexyloxy group, or a 4-butyloctyloxy group; alkylthio groups 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; fluorinated alkoxy groups 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; fluorinated alkoxy groups having 1 to 12 carbon atoms, such as a trifluoromethanethioalkoxy group; amino groups which may be substituted with one or two substituents having 1 to 25 carbon atoms, such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, a diphenylamino group, a piperidino group, a pyrrolidino group, or a methylethyl group; carbamoyl groups which may be substituted at the N-position with an alkyl having 1 to 6 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, or an N,N-dimethylcarbamoyl group; carbonyl groups such as a methylcarbonyloxy group or an ethylcarbonyloxy group; alkylcarbonyloxy groups having 2 to 12 carbon atoms; alkylsulfonyl groups having 1 to 12 carbon atoms, such as a methylsulfonyl group or an ethylsulfonyl group; 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; acyl groups having 2 to 12 carbon atoms, such as an acetyl group or an ethylcarbonyl group; and aldehyde groups.Examples of such alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 12 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and a butyloxycarbonyl group; alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as a methoxythiocarbonyl group and 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.

[0027] R 3 , R 4 , R 5 and R 6 Examples of the heterocyclic group represented by the formula (I) include an aliphatic heterocyclic group having 4 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms, such as an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, an imidazolidine ring group, a pyrazolidine 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, or a tetrahydrofuran ring group.

[0028] R 3 and R 4 The ring formed by combining R is a ring containing a nitrogen atom as a ring component. 3 and R 4 The ring formed by linking R may contain a heteroatom other than a nitrogen atom as a ring component. 3 and R 4 The ring formed by combining R may be a single ring or a condensed ring. 3 and R 4Examples of the ring formed by linking together include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a morpholine ring group, an indoline ring group, an imidazoline ring group, a pyrazole ring group, an imidazole ring group, a triazole ring group, a tetrazole ring group, a thiazolidinedione ring group, a succinimide ring group, an oxazolidone ring group, a piperazine ring group, a thiomorpholine ring group, a decahydroisoquinoline ring group, a decahydroquinoline ring group, a tetrahydroquinoline ring group, a carbazole ring group, a phenothiazine ring group, an azaadamantane ring group, an azocane ring group, and an azonane ring group. 3 and R 4 The hydrogen atoms contained in the ring formed by bonding together may be substituted with any substituent, and examples of such optional substituents include ring W 1 and Ring W 2 Examples of the substituents include the same groups as those which may be contained in the group.

[0029] R 5 and R 6 The ring formed by combining R is a ring containing a nitrogen atom as a ring component. 5 and R 6 The ring formed by linking R may contain a heteroatom other than a nitrogen atom as a ring component. 5 and R 6 The ring formed by combining R may be a single ring or a condensed ring. 5 and R 6 The ring formed by connecting these is R 3 and R 4 The rings formed by connecting R 5 and R 6 The hydrogen atoms contained in the ring formed by bonding together may be substituted with any substituent, and examples of such optional substituents include ring W 1 and Ring W 2 Examples of the substituents include the same groups as those which may be contained in the group.

[0030] R 3 , R 4 , R 5 and R 6are preferably each independently a hydrogen atom or a hydrocarbon group having 1 to 24 carbon atoms. R 3 and R 4 At least one selected from the above is preferably a hydrocarbon group having 1 to 24 carbon atoms, and more preferably an aromatic hydrocarbon group having 6 to 24 carbon atoms. R 5 and R 6 At least one selected from the above is preferably a hydrocarbon group having 1 to 24 carbon atoms, and more preferably an aromatic hydrocarbon group having 6 to 24 carbon atoms. R 3 and R 4 When they are linked together to form a ring, R 5 and R 6 are preferably linked to each other to form a ring.

[0031] The cation represented by formula (IA) is preferably a cation represented by formula (IB) or a cation represented by formula (IC). [ka] [In formula (IB) and formula (IC), Ring W 1 , Tamaki W 2 , R 1 and R 2 have the same meanings as above. Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent. R 4A and R 6A each independently represents a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent. Ring W 3 and Ring W 4 each independently represents a nitrogen-containing heterocyclic group.

[0032] Ar 1 and Ar 2The aromatic hydrocarbon group having 6 to 24 carbon atoms represented by R 3 The aromatic hydrocarbon group represented by Ar 1 and Ar 2 are each independently preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. R 4A and R 6A As the hydrocarbon group having 6 to 24 carbon atoms represented by R 3 The hydrocarbon groups represented by R 4A and R 6A are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 24 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 24 carbon atoms, and even more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 , Ar 2 , R 4A and R 6A The substituents that may be possessed by R 3 Examples of the substituents that may be possessed by the hydrocarbon group represented by the following formula are given.

[0033] Ring W 3 and Ring W 4 The nitrogen-containing heterocyclic group represented by the following formula may be a single ring or a condensed ring, and is preferably a condensed ring. Ring W 3 and Ring W 4 are preferably each independently an azetidine ring, a pyrrolidine ring, a piperidine ring, a morpholine ring, an imidazoline ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, a piperazine ring, a thiomorpholine ring, or an indoline ring.

[0034] The cation represented by formula (IB) is preferably a cation represented by formula (I-B1), and the cation represented by formula (IC) is preferably a cation represented by formula (I-C1). [ka] [In formula (I-B1) and formula (I-C1), ring W 3 , Tamaki W 4 , R 1 , R 2 , R 4A , R 6A , Ar 1 and Ar 2 have the same meaning as above.]

[0035] Examples of the cation containing the partial structure represented by formula (I) include the cations shown below. [ka]

[0036] [ka]

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] Examples of cations having a partial structure represented by formula (I) include those represented by formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-8), formula (I-12), formula (I-13), formula (I-17), formula (I-18), formula (I-23), formula (I-25), formula (I-26), formula (I-27), formula (I-28), formula (I-29), formula (I-31), formula (I-38), formula (I-60), formula (I-61), formula (I -62), formula (I-79), formula (I-80), formula (I-85), formula (I-87), formula (I-90), formula (I-93), formula (I-94), formula (I-95), formula (I-96), formula (I-101), formula (I-103), formula (I-105), formula (I-107), formula (I-128), formula (I-133), formula (I-135), formula (I-137), or formula (I-139).

[0045] <anion> Compound (I) is usually composed of a cation represented by formula (I) and a paired anion. The combination of the cation represented by formula (I) and the anion contained in compound (I) is not limited. When the valence of the anion is two or more, the compound may have a plurality of cations represented by formula (I). When the valence of the anion is two or more, the compound may have a cation represented by formula (I) and a cation other than the cation represented by formula (I). The anion may be an organic anion or an inorganic anion.

[0046] Examples of the organic anion include acetate anion, methide anion, amide anion, sulfonate anion, and borate anion, and methide anion, amide anion, sulfonate anion, and borate anion are preferred.

[0047] The methide anion is preferably an anion represented by formula (cA). [ka] [In formula (cA), R 1c , R 2c and R 3c each independently represents a monovalent substituent. R 1c , R 2c and R 3c The monovalent substituent represented by the formula (I) is not particularly limited, and examples thereof include a fluorine atom; a fluoroalkyl group having 1 to 12 carbon atoms, such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, or a tetrafluoroethyl group; a fluoroaryl group having 6 to 18 carbon atoms, such as a monofluorophenyl group or a tetrafluorophenyl group; a cyano group; a nitro group; or -SO2-R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom.) is preferred.

[0048] The amide anion is preferably an anion represented by formula (cB). [ka] [In formula (cB), R 4c and R 5c each independently represents a monovalent substituent. R 4c and R 5c The monovalent substituent represented by the formula (I) is not particularly limited, and examples thereof include a fluorine atom; a fluoroalkyl group having 1 to 12 carbon atoms, such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, or a tetrafluoroethyl group; a fluoroaryl group having 6 to 18 carbon atoms, such as a monofluorophenyl group or a tetrafluorophenyl group; a cyano group; a nitro group; or -SO2-R 11c (R 11cは and represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom.) is preferred.

[0049] The sulfonate anion is preferably an anion represented by formula (cC). [ka] [In formula (cC), R 6c represents a monovalent substituent. R 6c The monovalent substituent represented by the formula (I) is not particularly limited, and examples thereof include a fluorine atom; a fluoroalkyl group having 1 to 12 carbon atoms, such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, or a tetrafluoroethyl group; a fluoroaryl group having 6 to 18 carbon atoms, such as a monofluorophenyl group or a tetrafluorophenyl group; a cyano group; a nitro group; or -SO2-R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom.) is preferred.

[0050] The borate anion is preferably an anion represented by formula (cD). [ka] [In formula (cD), R 7c , R 8c , R 9c and R 10c each independently represents a monovalent substituent. R 7c , R 8c , R 9c and R 10c The monovalent substituent represented by the formula (I) is not particularly limited, and examples thereof include a fluorine atom; a fluoroalkyl group having 1 to 12 carbon atoms, such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, or a tetrafluoroethyl group; a fluoroaryl group having 6 to 18 carbon atoms, such as a monofluorophenyl group or a tetrafluorophenyl group; a cyano group; a nitro group; or -SO2-R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom.) is preferred.

[0051] The anion represented by formula (cA) is preferably an anion represented by formula (c-A1): The anion represented by formula (cB) is preferably an anion represented by formula (c-B1), The anion represented by formula (cC) is preferably an anion represented by formula (c-C1), The anion represented by formula (cD) is preferably an anion represented by formula (c-D1) or an anion represented by formula (c-D2). [ka] In formula (c-A1), Rf1, Rf2, and Rf3 each independently represent a fluoroalkyl group having 1 to 12 carbon atoms. In formula (c-B1), Rf4 and Rf5 each independently represent a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms. In formula (c-C1), Rf6 represents a fluoroalkyl group having 1 to 12 carbon atoms. In formula (c-D2), R 1d , R 2d , R 3d and R 4d each independently represents a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms. n1 to n4 each independently represents an integer of 0 to 5.

[0052] More specific examples of organic anions include acetate anion [CHCOO - ], trifluoroacetate anion [CF3COO - ], methanesulfonate anion [CH3SO3 - ], trifluoromethanesulfonate anion [CF3SO3 - ], p-toluenesulfonate anion〔p-CH3C6H4SO3 - ], bis(trifluoromethanesulfonyl)imide anion [(CF3SO2)2N - ], bis(nonafluorobutylsulfonyl)imide anion [(C4F9SO2)2N -], tris(trifluoromethanesulfonyl)methanide anion [(CF3SO2)3C - ], dimethylphosphinate anion [(CH3)2POO - ], (poly)hydrofluorofluoride anion [F(HF) m - ](m is 1 or more and 3 or less), perfluorobutanesulfonate anion [C4F9SO3 - ], bis(pentafluoroethanesulfonyl)imide anion [(C2F5SO2)2N - ], perfluorobutanoate anion [C3F7COO - ], (trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion [(CF3SO2)(CF3CO)N - ], perfluoropropane-1,3-disulfonate anion [ - O3S(CF2)3SO3 - ], carbonate anion [CO3 2- ], tetracyanoborate, tetrakis(pentafluorophenyl)borate, tetrakisphenylborate, tris(pentafluoroethyl)trifluorophosphate [P - (C2F5)3F3], etc.

[0053] Examples of inorganic anions include fluoride ions, chloride anions, bromide anions, iodide anions, and tetrachloroaluminate anions (AlCl4 - ], heptachlorodialuminate anion [Al2Cl7 - ], tetrafluoroborate anion [BF4 - ], hexafluorophosphate anion [PF6 - ], perchlorate anion [ClO4 - ], nitrate anion [NO3 - ], hexafluoroarsenate anion [AsF6 - ], hexafluoroantimonate anion [SbF6 - ], hexafluoroniobate anion [NbF6 -], hexafluorotantalate anion [TaF6 - ], dicyanamide anion [(CN)2N - ], bis(fluorosulfonyl)imide anion [(FSO2)2N - ], phosphate anion (PO4 3- ), thiocyanate anion [SCN - ] etc.

[0054] The inorganic anion is bis(fluorosulfonyl)imide anion (N - (SO2F)2) is preferred. The organic anion is trifluoroacetate anion [CF3COO - ], trifluoromethanesulfonate anion [CF3SO3 - ], bis(trifluoromethanesulfonyl)imide anion [(CF3SO2)2N - ], tris(trifluoromethanesulfonyl)methanide anion [(CF3SO2)3C - ], perfluorobutanesulfonate anion [C4F9SO3 - ], bis(pentafluoroethanesulfonyl)imide anion [(C2F5SO2)2N - ], perfluorobutanoate anion [C3F7COO - ], (trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion [(CF3SO2)(CF3CO)N - ], perfluoropropane-1,3-disulfonate anion [ - O3S(CF2)3SO3 - ], tetrakisarylborate anions (tetrakisphenylborate, tetrakis(pentafluorophenyl)borate), and tetracyanoborate are preferred, and bis(trifluoromethanesulfonyl)imide anion [(CF3SO2)2N - ], tris(trifluoromethanesulfonyl)methanide anion [(CF3SO2)3C - ], tetrakis(pentafluorophenyl)borate, and tetracyanoborate, and particularly preferred is tetrakis(pentafluorophenyl)borate.

[0055] Examples of compound (I) include the compounds shown in Tables 1 to 8. Compound (1) in Table 1 is a compound having a cation represented by formula (I-1) and a chloride anion, and is the compound shown below. [ka]

[0056] [Table 1]

[0057] [Table 2]

[0058] [Table 3]

[0059] [Table 4]

[0060] [Table 5]

[0061] [Table 6]

[0062] [Table 7]

[0063] [Table 8]

[0064] Compound (I) includes compound (3), compound (39), compound (40), compound (41), compound (43), compound (45), compound (46), compound (47), compound (49), compound (53), compound (55), compound (56), compound (57), compound (58), compound (59), compound (60), compound (65), compound (66), compound (67), compound (70), compound (72), compound (75), compound (115), compound (116), compound (117), compound (119), compound (121), compound ( 122), compound (123), compound (125), compound (129), compound (131), compound (132), compound (133), compound (134), compound (135), compound (136), compound (141), compound (142), compound (143), compound (1) 46), Compound (148), Compound (151), Compound (153), Compound (154), Compound (155), Compound (157), Compound (159), Compound (160), Compound (161), Compound (163), Compound (167), Compound (169), Compound (17) 0), compound (171), compound (172), compound (173), compound (174), compound (179), compound (180), compound (181), compound (184), compound (186), compound (189), compound (191), compound (192), compound (193) ), compound (195), compound (197), compound (198), compound (199), compound (201), compound (205), compound (207), compound (208), compound (209), compound (210), compound (211), compound (212), compound (217) , Compound (218), Compound (219), Compound (222), Compound (224), Compound (227), Compound (267), Compound (268), Compound (269), Compound (271), Compound (273), Compound (274), Compound (275), Compound (277), Compound (281), Compound (283), Compound (284), Compound (285), Compound (286), Compound (287), Compound (288), Compound (293), Compound (294), Compound (295), Compound (298), Compound (300).

[0065] <Method for producing compound (I)> A cation containing the partial structure represented by formula (I) that compound (I) has can be produced by reacting a compound represented by formula (M) (hereinafter, sometimes referred to as compound (M)), a compound represented by formula (b-1) (hereinafter, sometimes referred to as compound (b-1)), and a compound represented by formula (b-2) (hereinafter, sometimes referred to as compound (b-2)). [ka] [In the formula, ring W 1 , Tamaki W 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the same meaning as above.]

[0066] The reaction of the compound (M), the compound (b-1) and the compound (b-2) 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, iodomethane, trimethyloxonium tetrafluoroborate, and dimethyl fluorosulfate; and sulfonic acid halides such as paratoluenesulfonyl chloride and trifluoromethanesulfonyl chloride. The amount of the catalyst used is usually 0.001 to 10 mol, and preferably 0.05 to 2 mol, per 1 mol of compound (M).

[0067] The reaction of compound (M), compound (b-1) and compound (b-2) 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 methyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, and phenyl lithium; methyl magnesium 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 0.1 to 10 mol, preferably 0.5 to 2 mol, per 1 mol of compound (M).

[0068] The reaction of compound (M), compound (b-1) and compound (b-2) 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, a ketone solvent, or an aromatic hydrocarbon solvent, and more preferably acetonitrile, toluene, methyl ethyl ketone, or methyl isobutyl ketone. The amount of the solvent used is usually 0.5 to 1000 parts by mass, and preferably 1 to 10 parts by mass, per part by mass of the compound (M).

[0069] The reaction of compound (M), compound (b-1), and compound (b-2) is carried out by mixing compound (M), compound (b-1), and compound (b-2). The reaction of compound (M), compound (b-1) and compound (b-2) is preferably carried out by adding compound (b-1) and compound (b-2) to a mixture of compound (M), a base and a catalyst. The amount of compound (b-1) used is usually 0.1 to 20 moles, and preferably 0.5 to 4 mole equivalents, per mole of compound (M). The amount of compound (b-2) used is usually 0.1 to 20 moles, and preferably 0.5 to 4 mole equivalents, per mole of compound (M).

[0070] The reaction time of the compound (M), the compound (b-1) and the compound (b-2) is usually 0.1 to 100 hours. The reaction temperature of the compound (M), the compound (b-1) and the compound (b-2) is usually -80 to 200°C.

[0071] Examples of the compound (b-1) and the compound (b-2) include aziridine, azetidine, pyrrolidine, piperidine, morpholine, thiomorpholine, indoline, methylindoline, nitroindoline, aminobiphenyl, cyanoaminobiphenyl, nitroaminobiphenyl, and methoxyaminobiphenyl.

[0072] Examples of the compound (M) include the compounds described below. [ka]

[0073] Compound (M) can be produced by reacting a compound represented by formula (M1-1) (hereinafter sometimes referred to as compound (M1-1)), 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)). [ka] [In the formula, ring W 1 , Tamaki W 2 , R 1 and R 2 has the same meaning as above. E1 and E2 each independently represent a leaving group.]

[0074] The leaving groups represented by E1 and E2 each independently include a halogen atom, a succinimide group, a maleimide group, saccharin, a methylsulfonyl group, a p-methoxybenzenesulfonyl group, a p-toluenesulfonyl group, a trifluoromethylsulfonyl group, and a nonafluorobutanesulfonyl group.

[0075] The reaction of the compound (M1-1), the compound (M1-2) and the compound (M1-3) is preferably carried out in the presence of a base. Examples of the base include the same bases as those used in the reaction of compound (M), compound (b-1), and compound (b-2), 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 hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, methyllithium, n-butyl More preferred are lithium, tertiary butyl lithium, 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 (M1-1).

[0076] The reaction of compound (M1-1), 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 compound (M), compound (b-1), and compound (b-2). Preferred solvents include acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide, and dimethylacetamide. The solvent is preferably a dehydrated solvent.

[0077] The reaction of compound (M1-1), compound (M1-2), and compound (M1-3) is carried out by mixing compound (M1-1), compound (M1-2), and compound (M1-3), and is preferably carried out by mixing a base, compound (M1-1), compound (M1-2), and compound (M1-3). The reaction of the compound (M1-1), the compound (M1-2) and the compound (M1-3) is preferably carried out in an oxygen-free atmosphere (for example, in a nitrogen atmosphere).

[0078] 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). 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 (M1-1). The reaction time of the compound (M1-1), the compound (M1-2) and the compound (M1-3) is usually 0.1 to 200 hours. The reaction temperature of the compound (M1-1), the compound (M1-2) and the compound (M1-3) is usually -100 to 200°C.

[0079] As the compound (M1-1), commercially available products may be used, and examples thereof include 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one. 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.

[0080] When compound (M), compound (b-1), and compound (b-2) are reacted in the presence of a base, compound (I) having an anion derived from the base and a cation represented by formula (IA) can be obtained. When the anion of compound (I) is to be exchanged for a desired anion, ion exchange can be carried out by mixing compound (I) with a salt having the desired anion. The ion exchange can be carried out in the presence of a solvent. Examples of the salt having the desired anion include lithium salt, sodium salt, potassium salt, cesium salt, barium salt, calcium salt, magnesium salt, and ammonium salt.

[0081] <Composition containing compound (I)> The present invention also includes compositions containing Compound (I). The composition containing compound (I) can be used in a variety of applications, but is particularly suitable for applications where it may be exposed to sunlight or light including ultraviolet light. Specific examples include glass substitutes and surface coating materials thereof; coating materials for window glass, lighting glass, and light source protection glass for homes, facilities, transportation equipment, etc.; window films for homes, facilities, transportation equipment, etc.; interior and exterior materials and interior and exterior paints for homes, facilities, transportation equipment, etc., and coating films formed therefrom; alkyd resin lacquer paints and coating films formed therefrom; acrylic lacquer paints and coating films formed therefrom; components for light sources that emit ultraviolet light, such as fluorescent lamps and mercury lamps; materials for blocking electromagnetic waves generated by precision machinery, electronic and electrical equipment, and various displays; containers or packaging materials for food, chemicals, pharmaceuticals, etc.; bottles, boxes, blisters, cups, special packaging, compact disc coatings, agricultural and industrial sheets or films; anti-fading agents for printed matter, dyed materials, dyes and pigments, etc.; polymer supports (e.g., 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; interlayers for safety glass and windshields; electrochromic or photochromic applications; overlaminate films; solar heat control films; cosmetics such as sunscreen creams, shampoos, conditioners, and hair styling products; textiles and fabrics for clothing such as sportswear, stockings, and hats; household interior furnishings 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.

[0082] 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)").

[0083] 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.

[0084] Examples of thermosetting resins include epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, and thermosetting polyimide resins.

[0085] The shape of the polymer molded product (molded article) formed from the resin composition may be any of a flat film, powder, spherical particles, crushed particles, a continuous block, fiber, tube, hollow fiber, granule, plate, porous, etc. When the resin composition is used as an ultraviolet absorbing filter or an ultraviolet absorbing film, the resin is preferably a transparent resin. 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.

[0086] 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.

[0087] <Layer Containing Compound (I)> The present invention includes an optical layer containing a cation having a partial structure represented by formula (I). The optical layer containing a cation having a partial structure represented by formula (I) is usually formed from an optical layer containing compound (I). The optical layer containing compound (I) can be laminated on a display element such as an organic EL element or a liquid crystal cell, and used in image display devices (FPD: flat panel displays) such as organic EL display devices and liquid crystal display devices. The optical layer may be formed using the resin composition of the present invention. When the resin composition of the present invention is applied to an image display device, the optical layer formed from the resin 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 a pressure-sensitive adhesive layer or a coating layer. The optical layer containing the compound (I) is preferably formed from the above-mentioned resin composition or composition (1). The optical layer containing compound (I) may consist solely of an optical layer containing compound (I), or may be an optical laminate in which a layer containing compound (I) and other layers are laminated. Examples of other layers include a polarizing film (polarizer), a retardation film, a thermoplastic resin film, and a wavelength conversion layer. 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 a resin composition. 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 composition (1). 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 a resin composition. When the optical layer of the present invention and a wavelength conversion layer are laminated, the optical layer of the present invention is preferably positioned closer to the viewer than the wavelength conversion layer.

[0088] <Adhesive composition> When the layer formed from the composition of the present invention is a pressure-sensitive adhesive layer, it is formed from a pressure-sensitive adhesive composition (hereinafter sometimes referred to as pressure-sensitive adhesive composition (1)) containing a resin (A), a compound (I), a crosslinking agent (B), and a silane compound (C). The pressure-sensitive adhesive composition (1) 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 absorbing 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 absorbing compound (F).

[0089] There are no particular limitations on the resin (A) as long as it is a resin that can be used in a pressure-sensitive adhesive composition. It is preferable that the resin (A) does not exhibit a maximum absorption in the wavelength range of 300 nm to 780 nm. The resin (A) preferably has a glass transition temperature (Tg) of 40°C or lower. The glass transition temperature (Tg) of the resin (A) is more preferably 20°C or lower, even more preferably 10°C or lower, and particularly preferably 0°C or lower. The glass transition temperature of the resin (A) is usually -80°C or higher, preferably -70°C or higher, more preferably -60°C or higher, even more preferably -55°C or higher, and particularly preferably -50°C or higher. A glass transition temperature of the resin (A) of 40°C or lower is advantageous in improving the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (1) to the adherend. A glass transition temperature of the resin (A) of -80°C or higher is advantageous in improving the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (1). The glass transition temperature can be measured by a differential scanning calorimeter (DSC).

[0090] Examples of the resin (A) include (meth)acrylic resins, silicone resins, rubber resins, and urethane resins, with (meth)acrylic resins being preferred.

[0091] The (meth)acrylic resin is preferably a polymer containing, as the main component (preferably containing 50% by mass or more) a structural unit derived from a (meth)acrylic acid ester. The (meth)acrylic resin may contain a structural unit derived from one or more monomers other than a (meth)acrylic acid ester (for example, a structural unit derived from a monomer having a polar functional group such as a hydroxyl group, a carboxyl group, or an amino group).

[0092] The content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, and more preferably 70% by mass to 90% by mass, based on 100% by mass of the solid content of the adhesive composition (1). The content of 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).

[0093] 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).

[0094] 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).

[0095] The radically curable component (D) may be a radically curable component such as a compound or oligomer that is cured by a radical polymerization reaction. Examples of the radically polymerizable component (D) include (meth)acrylate compounds, styrene compounds, and vinyl compounds. The pressure-sensitive adhesive composition (1) may contain two or more types of radically curable components (D).

[0096] 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.

[0097] 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.

[0098] 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).

[0099] 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.

[0100] 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).

[0101] 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.

[0102] 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).

[0103] 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 with a wavelength of 380 to 780 nm, or a compound (infrared absorber) that absorbs light with a wavelength of 780 nm 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).

[0104] <Dyed items dyed with compound (I)> The present invention includes dyed articles (e.g., textiles, films, resins, etc.) dyed with Compound (I). Dyeing with Compound (I) is carried out, for example, by immersing an article such as a fiber, film, or resin in a solution in which Compound (I) is dissolved in a solvent. [Example]

[0105] The present invention will be described in more detail below with reference to Examples and Comparative Examples. In the Examples and Comparative Examples, "%" and "parts" are "% by mass" and "parts by mass" unless otherwise specified.

[0106] Example 1: Synthesis of compound represented by formula (1) [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). A 100 mL four-neck flask equipped with a Dimroth condenser and a thermometer was conditioned under a nitrogen atmosphere, and 4 parts of the compound represented by formula (M-2), 40 parts of dehydrated acetonitrile, and 6.6 parts of diisopropylethylamine were added and stirred in an ice bath. 7.2 parts of trifluoromethanesulfonic anhydride were added to the resulting mixture and stirred in an ice bath for 15 minutes, after which 3 parts of indoline were added and stirred in an ice bath for 2 hours. The solvent was distilled off from the resulting mixture, and the mixture was purified using hydrochloric acid and ethyl acetate to obtain the compound represented by formula (1).

[0107] 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 chloride anions. 1 H-NMR (deuterated dimethyl sulfoxide) δ: 7.07-7.42 (m, 8H), 5.95 (s, 1H), 4.11-4.16 (m, 4H), 2.99-3.20 (m, 5H), 2.50 (m, 2H), 2.05 (m, 2H), 1.56 (m, 4H) LC-MS; [M] = 392.5

[0108] <Measurement of maximum absorption wavelength and gram absorption coefficient ε> The obtained 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 set in a spectrophotometer UV-2450 (Shimadzu Corporation). The absorbance was measured in 1 nm steps in the wavelength range of 300 to 800 nm using the double beam method. The gram absorption coefficient for each wavelength was calculated from the obtained 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 509 nm, and the gram absorption coefficient ε (λmax) at the maximum absorption wavelength of the compound represented by formula (1) was 52 L / (g cm).

[0109] Furthermore, from the measured absorbance, two wavelengths were identified where the absorbance was half that of the maximum absorption wavelength. Of the two wavelengths, the wavelength on the shorter wavelength side was subtracted from the wavelength on the longer wavelength side to obtain the full width at half maximum. The full width at half maximum of the compound represented by formula (1) was 67 nm.

[0110] Polymerization Example 1: Preparation of acrylic resin (A1) A reaction vessel equipped with a condenser, nitrogen inlet, thermometer, and stirrer was charged with a mixed solution of 81.8 parts ethyl acetate as a solvent, 96 parts butyl acrylate, 3 parts 2-hydroxyethylmethyl acrylate, and 1 part acrylic acid. The air in the vessel was purged with nitrogen gas to remove oxygen, and the internal temperature was raised to 55°C. A solution of 0.14 parts azobisisobutyronitrile (polymerization initiator) in 10 parts ethyl acetate was then added in its entirety. After the initiator addition, the temperature was maintained 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).

[0111] Example 2: Preparation of resin composition (1) (adhesive 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 0.5 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). Note that the amount of crosslinker is expressed in parts by mass as the active ingredient.

[0112] Example 3 and Comparative Example 1: Preparation of resin compositions (2) and (3) Resin compositions (2) and (3) were prepared in the same manner as in Example 2, except that the components and the amounts of the components were changed as shown in Table 9. The blending amount of the crosslinking agent is expressed in parts by mass as the active ingredient, and that of resin (A) is expressed in parts by mass as the solid content.

[0113] [Table 9]

[0114] The abbreviations in Table 9 have the following meanings: Acrylic resin (A1): Acrylic resin (A1) synthesized in Polymerization Example 1 Formula (1): Compound represented by formula (1) synthesized in Example 1 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 Formula (B): The 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 paratoluenesulfonate) was 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]

[0115] <Evaluation of Molded Article of Resin Composition (1)> [Production of resin molded body (1)] The obtained resin composition (1) was applied using an applicator to the release-treated surface of a release-treated polyethylene terephthalate separate film (trade name "PLR-382190" obtained from Lintec Corporation) and dried at 100°C for 1 minute to produce a resin molded body (adhesive layer) (1). The thickness of the obtained resin molded body (1) was 20 µm.

[0116] [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) to obtain a pressure-sensitive adhesive layer with double-sided separate films. The obtained resin layer (1) with double-sided separate films was stored in air at a temperature of 23 to 25°C for one month. After storage, the resin molded article (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. Cases where no crystalline precipitation was observed were evaluated as a, and cases where crystalline precipitation was observed were evaluated as b. The evaluation results are shown in Table 10.

[0117] [Measurement of absorbance retention of resin molded product (1)] A polarizing plate was prepared by laminating a 13 μm thick cycloolefin film to one surface of an 8 μm thick polarizer using an adhesive layer. The resin molded body (1) was attached to the polarizer side of the polarizing plate using a laminator, and then aged for 7 days at a temperature of 23°C and a relative humidity of 65% to obtain a laminate of cycloolefin film / polarizer / resin molded body (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 attached to obtain a laminate (1-1) having a laminate structure of cycloolefin film / polarizer / resin molded body (1) / glass. The obtained laminate (1-1) 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 (1-1) was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 500 nm was calculated based on the following formula. The results are shown in Table 10. The closer the absorbance retention is to 100, the less deterioration of the light selective absorption function there is and the better the weather resistance is. The absorption wavelength for evaluating the absorbance retention rate 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(500) after weather resistance test / A(500) before weather resistance test) x 100 [In the formula, A(500) represents the absorbance of the laminate (1-1)]

[0118] Resin composition (2) was used instead of resin composition (1), and resin molded product (2) and laminate (2-1) were produced and evaluated in the same manner. The results are shown in Table 10.

[0119] Resin composition (3) was used instead of resin composition (1), and resin molded body (3) and laminate (3-1) were prepared and evaluated in the same manner. The absorbance retention was evaluated at a wavelength of 510 nm. The results are shown in Table 10.

[0120] [Table 10]

[0121] 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 a cation represented by the following formula (IC): 【Chemistry 1】 [In formula (IC), Ring W １ and Ring W ２ each independently represents a ring structure having at least one double bond as a ring component. Ring W １ and Ring W ２ may each independently have a substituent. R １ and R ２ each independently represents a hydrogen atom or a cyano group; R １ and R ２ At least one of them is a cyano group. Ring W 3 and ring W 4 each independently represent a nitrogen-containing heterocyclic group.]

2. The compound according to claim 1, which exhibits a maximum absorption between wavelengths of 400 nm and 700 nm.

3. A composition comprising the compound of claim 1 and a resin.

4. A composition comprising the compound of claim 1 and a polymerizable monomer.

5. A molded article formed from the composition according to claim 3 or 4.

6. A dyed article dyed with the compound according to claim 1.

7. An optical layer containing a cation represented by the following formula (IC): 【Chemistry 2】 [In formula (IC), Ring W １ and Ring W ２ each independently represents a ring structure having at least one double bond as a ring component. Ring W １ and Ring W ２ may each independently have a substituent. R １ and R ２ each independently represents a hydrogen atom or a cyano group; R １ and R ２ At least one of them is a cyano group. Ring W 3 and ring W 4 each independently represent a nitrogen-containing heterocyclic group.]

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