Compounds

Abstract

A compound having an anion represented by the following formula (I) [in formula (I), ring W 1 represents a ring which can have a substituent. Ring W 2 represents a ring having at least one double bond as a constituent element of the ring, ring W 2 may have a substituent. R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, R 1 and at least one of R 2 has a monovalent substituent. R 3 , R 4 , R 5 and R 6 each independently represent 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.

Description

TECHNICAL FIELD

[0001] The present application relates to a compound. BACKGROUND

[0002] For the purpose of coloring of an object, transmission or absorption of light of a specific wavelength, and the like, a colorant compound that absorbs visible light is used for a wide range of applications such as fibers, inks, paints, containers, packaging materials, printed matters, optical articles, eyeglasses, display devices, and the like. As important properties of a colorant compound, selectivity (sharpness of an absorption spectrum) and durability (particularly, light resistance) can be cited. Among colorant compounds, cyanine pigments are widely used from the aspect that a wavelength at which a wide absorption is exhibited from an ultraviolet region of 380 nm or less to a near infrared region of 780 nm or more can be controlled by controlling the number of methine carbon atoms in a methine skeleton, and the aspect that a cyanine pigment mostly exhibits relatively high selectivity. (For example, U.S. Patent No. 6004536 (Patent Document 1)).

[0003] PRIOR ART DOCUMENTS

[0004] PATENT DOCUMENTS

[0005] Patent Document 1: U.S. Patent No. 6004536 SUMMARY

[0006] PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] However, although cyanine pigments have high selectivity, there are many cyanine pigments that have poor durability (among which, light resistance) and there is a demand for a compound that has both high selectivity and durability.

[0008] MEANS FOR SOLVING THE PROBLEMS

[0009] The present application includes the following inventions.

[0010] [1] A compound having an anion represented by the following formula (I).

[0011]

[0012] [In formula (I), ring W 1 represents a ring that can have a substituent.

[0013] 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.

[0014] R 1 and R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and R2 At least one of them has a monovalent substituent.

[0015] R 3 R 4 R 5 and R 6 Each can independently represent a hydrogen atom or a monovalent substituent.

[0016] R 1 With R 4 They can be connected to form a ring.

[0017] R 3 With R 4 They can be connected to form a ring.

[0018] R 2 With R 6 They can be connected to form a ring.

[0019] R 5 With R 6 They can be connected to form a ring.

[0020] [2] According to the compound described in [1], wherein, is selected from R 1 and R 2 At least one of them is an electron-withdrawing group.

[0021] [3] According to the compound described in [2], wherein, is selected from R 1 and R 2 At least one of them is cyano, nitro, haloalkyl, haloaryl, -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 or halogen atom that can have substituents. -OCF3, -SCF3, -SF5, -SF3, -SO2H, or -SO3H.

[0022] [4] According to any one of [1] to [3], the compound is selected from R 3 R 4 R 5 and R 6 At least one of them is an electron-withdrawing group.

[0023] [5] According to any one of [1] to [4], wherein R 3 R 4 R 5 and R6 each independently an electron-withdrawing group.

[0024] [6] The compound according to [5], wherein at least one of R 3 , R 4 , R 5 , and R 6 is a cyano group, a nitro group, a haloalkyl group, a haloaryl group, -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, R 3z , R4, R5, R6, R7, R8, and R9 each independently represent a hydrocarbon group which can have a substituent or a halogen atom.), -OCF3, -SCF3, -SF5, -SF3, -SO2H, or -SO3H.

[0025] [7] The compound according to any one of [1] to [6], which shows a large absorption between wavelengths of 400 nm and 700 nm.

[0026] [8] The compound according to any one of [1] to [7], which has a specific absorption coefficient of 50 [L / (g-cm)] or more at a wavelength of a large absorption.

[0027] [9] A resin composition comprising the compound according to any one of [1] to [8] and a resin.

[0028]

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

[0029]

[11] A shaped body shaped from the resin composition according to [9] or the composition according to

[10] .

[0030]

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

[10] .

[0031]

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

[12] .

[0032]

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

[13] .

[0033]

[15] A method for producing a compound having an anion represented by formula (I):

[0034]

[0035] [In formula (I), ring W 1, ring W 2 , R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represent the same meaning as described above.

[0036] The production method of the compound includes a step of reacting a compound represented by formula (M-A) with a compound represented by formula (b-3),

[0037]

[0038] [In formula (M-A), ring W 1 represents a ring which can have a substituent.

[0039] 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.

[0040] R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 has a monovalent substituent.

[0041] R 3 and R 4 each independently represent a hydrogen atom or a monovalent substituent.

[0042] R 1 and R 4 may be linked to each other to form a ring.

[0043] R 3 and R 4 may be linked to each other to form a ring.

[0044]

[0045] [In formula (b-3), R 5 and R 6 each independently represent a hydrogen atom or a monovalent substituent.

[0046] X2 represents a divalent linking group.

[0047]

[16] The production method described in

[15] , further comprising a step of obtaining a compound represented by formula (M-A) by reacting a compound represented by formula (M) with a compound represented by formula (b-2) in the presence of a catalyst,

[0048]

[0049] [In formula (M), ring W 1 , ring W 2 , R 1 , and R 2 each represent the same meaning as described above.]

[0050]

[0051] [In formula (b-2), R 3 and R 4 each represent the same meaning as described above.

[0052] X1represents a divalent linking group.

[0053]

[17] A method for producing a compound having an anion represented by formula (I):

[0054]

[0055] [In formula (I), ring W 1 , ring W 2 , R 3 , R 4 , R 5 , and R 6 each represent the same meaning as described above.

[0056] R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, at least one of R 1 and R 2 has a monovalent substituent.

[0057] The method for producing the compound reacts at least one compound selected from a compound represented by formula (M1-2) and a compound represented by formula (M1-3) with a compound having an anion represented by formula (M1-1),

[0058] R 2′ -E1 (M1-2)

[0059] [In formula (M1-2), R 2’ represents a monovalent substituent, and E1 represents a leaving group.]

[0060] R 1′ -E2 (M1-3)

[0061] [In formula (M1-3), R 1’ represents a monovalent substituent, and E2 represents a leaving group.]

[0062]

[0063] [In formula (M1-1), ring W 1 represents a ring which can have a substituent.

[0064] ring W 2 represents a ring having at least one double bond as a constituent element of the ring, ring W 2 may have a substituent.

[0065] R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or a monovalent substituent.

[0066] R 3 and R 4 may be linked to each other to form a ring.

[0067] R 5 and R 6 may be linked to each other to form a ring.

[0068]

[18] A compound represented by formula (M).

[0069]

[0070] [In formula (M), ring W 1 represents a ring which can have a substituent.

[0071] ring W 2 represents a ring having at least one double bond as a constituent element of the ring, ring W 2 may have a substituent.

[0072] R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, at least one of R 1 and R 2 has a monovalent substituent.

[0073]

[19] A compound represented by formula (M-A).

[0074]

[0075] [In formula (M-A), ring W 1 represents a ring which can have a substituent.

[0076] ring W 2 represents a ring having at least one double bond as a constituent element of the ring, ring W 2 may have a substituent.

[0077] R 1 and R 2each independently represents a hydrogen atom or a monovalent substituent, R 1 and at least one of R 2 has a monovalent substituent.

[0078] R 3 and at least one of R 4 each independently represents a hydrogen atom or a monovalent substituent.

[0079] R 1 and R 4 may be linked to each other to form a ring.

[0080] R 3 and R 4 may be linked to each other to form a ring.

[0081] Inventive Effects

[0082] An object of the present application is to provide a novel compound which shows good selective absorbency for light in the vicinity of a maximum absorption wavelength in the visible light region (wavelength 400 nm to wavelength 750 nm, preferably wavelength 450 to wavelength 600 nm) and has good light resistance. DETAILED DESCRIPTION

[0083] The compound of the present application is a compound having an anion represented by Formula (I) (hereinafter, sometimes referred to as Compound (I)).

[0084]

[0085] [In Formula (I), ring W 1 represents a ring which can have a substituent.

[0086] 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.

[0087] R 1 and at least one of R 2 each independently represents a hydrogen atom or a monovalent substituent, R 1 and at least one of R 2 has a monovalent substituent.

[0088] R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or a monovalent substituent.

[0089] R 1 and R 4 may be linked to each other to form a ring.

[0090] R3 R 4 may be linked to each other to form a ring.

[0091] R 2 R 6 may be linked to each other to form a ring.

[0092] R 5 R 6 may be linked to each other to form a ring.

[0093] <Anion>

[0094] The anion represented by formula (I) also includes all resonance structures represented by the following.

[0095]

[0096] In addition, depending on the kind of the monovalent substituent represented by R 3 , R 4 , R 5 , and R 6 , there is a case where the electron delocalization reaches R 3 , R 4 , R 5 , and R 6 . For example, in the case where the electron delocalization reaches the monovalent substituent represented by R 3 , R 4 , R 5 , and R 6 represented by the following, its resonance structure is also included in the anion represented by formula (I).

[0097]

[0098] The ring structure of the ring W 1 is not particularly limited. The ring W 1 may be a monocyclic ring or a fused ring.

[0099] The ring W 1 may be a heterocycle including a hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, and the like) as a component of the ring, or a hydrocarbon ring including a carbon atom and a hydrogen atom. The ring W 1 is preferably a ring including a hydrocarbon. The ring W 1 may be a ring having no aromaticity (aliphatic ring) or an aromatic ring, and is preferably an aliphatic ring. If it is a ring having no aromaticity, the selective absorbance can be further improved.

[0100] The ring W 1 is preferably a ring structure of 3 to 20-membered ring, more preferably 3 to 12-membered ring, and is preferably a 4 to 6-membered ring.

[0101] The ring W1 Preferably, it is a monocyclic ring.

[0102] Ring W 2 represents a ring structure having at least one double bond as a constituent element of the ring. Ring W 2 having one or more double bonds as a constituent element of the ring, Ring W 2 The number of double bonds contained in Ring W is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and further preferably 1.

[0103] Ring W 2 It can be a monocyclic ring or a polycyclic ring. Ring W 2 It can be an aromatic ring or a ring which does not have aromaticity (aliphatic ring), and is preferably a ring which does not have aromaticity. If it is a ring which does not have aromaticity, the selective absorbency can be further improved.

[0104] Ring W 2 It can be a heterocyclic ring containing a hetero atom (e.g., nitrogen atom, oxygen atom, sulfur atom, etc.) or a ring containing a hydrocarbon. Ring W 2 Preferably, it is a ring containing a hydrocarbon.

[0105] Ring W 2 Preferably, it is a ring structure of 3- to 20-membered ring, more preferably 3- to 12-membered ring, and preferably 4- to 6-membered ring.

[0106] Ring W 1 forms a fused ring with Ring W 2 Ring W 1 forms a fused ring with Ring W 2 Preferably, it is a fused ring of aliphatic hydrocarbon, and more preferably a fused ring of aliphatic hydrocarbon having 6 to 40 carbon atoms.

[0107] Ring W 1 forms a fused ring with Ring W 2 The fused ring formed by Ring W 1 -1) to Formula (W 1 -19) and the like. In addition, the fused ring formed by Ring W 1 forms a fused ring with Ring W 2 The fused ring formed by Ring W

[0108]

[0109] Ring W 1 forms a fused ring with Ring W 2each independently can have a substituent. As the substituent, there can be mentioned a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like; an aliphatic hydrocarbon group having 1 to 25 carbon atoms such as a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a tert-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, a butadienyl group, and the like (preferably an alkyl group having 1 to 12 carbon atoms); a halogenated alkyl group 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, a nonafluorobutyl group, and the like; an alkoxy group having 1 to 25 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentoxy group, a hexyloxy group, a 2-ethylhexyloxy group, a 4-butyloctyloxy group, and the like; 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, a hexylthio group, and the like; 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, a hexafluoroisopropoxy group, and the like; a fluorinated alkylthio group having 1 to 12 carbon atoms such as a trifluoromethylthio group; an amino group; an amino group which can be substituted with 1 or 2 aliphatic hydrocarbon groups having 1 to 25 carbon atoms such as a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a tert-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, a butadienyl group, and the like (preferably an alkyl group having 1 to 12 carbon atoms); a carbamoyl group in which the N-position can be substituted with an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a tert-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, a butadienyl group, and the like (preferably an alkyl group having 1 to 12 carbon atoms); an alkylcarbonyloxy group having 2 to 12 carbon atoms such as a methylcarbonyloxy group, an ethylcarbonyloxy group, and the like; an alkylsulfonyl group having 1 to 12 carbon atoms such as a methylsulfonyl group, an ethylsulfonyl group, and the like; an aromatic hydrocarbon group having 6 to 25 carbon atoms such as a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, and the like (preferably an aryl group having 6 to 18 carbon atoms); an arylsulfonyl group having 6 to 12 carbon atoms such as a phenylsulfonyl group; an alkoxysulfonyl group having 1 to 12 carbon atoms such as a methoxysulfonyl group, an ethoxysulfonyl group, and the like; a fluorinated alkylsulfonyl group having 1 to 12 carbon atoms such as a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a trifluoroethylsulfonyl group, and the like; an acyl group having 2 to 12 carbon atoms such as an acetyl group, an ethylcarbonyl group, and the like; an aldehyde group; an alkoxycarbonyl group having 2 to 12 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, and the like; an alkoxylthiocarbonyl group having 2 to 12 carbon atoms such as a methoxylthiocarbonyl group, an ethoxylthiocarbonyl group, and the like; a cyano group; a nitro group; a hydroxyl group; a thiol group; a sulfo group; a carbamoyl group; a carboxyl group; -SF3; -SF5; and the like.

[0110] The fused ring formed by the ring W 1 and the ring W 2 may also have a substituent, and the substituent can be mentioned as the ring W 1 or the ring W 2It can have substituents.

[0111] R 1 and R 2 Each independently represents a hydrogen atom or a monovalent substituent, selected from R. 1 and R 2 At least one of them is a monovalent substituent.

[0112] R 1 and R 2 The monovalent substituents shown are not particularly limited as long as they are not hydrogen atoms. Examples include monovalent aliphatic hydrocarbon groups, monovalent aromatic hydrocarbon groups, electron-withdrawing groups, electron-donating groups, heterocyclic groups, and groups with polyoxyalkylene groups.

[0113] As R 1 and R 2 Examples of monovalent aliphatic hydrocarbon groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-dodecyl, isododecyl, undecyl, lauryl, myristyl, cetyl, stearyl, 2-ethylhexyl, 4-butyloctyl, etc., which are straight-chain or branched alkyl groups with 1 to 25 carbon atoms; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., which are cycloalkyl groups with 3 to 25 carbon atoms; cycloalkyl groups with 4 to 25 carbon atoms, such as cyclohexylmethyl; alkylcycloalkyl groups with 4 to 25 carbon atoms, such as isobornyl; and unsaturated aliphatic hydrocarbon groups such as vinyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl, butadieneyl, etc. Preferably, it is a straight-chain or branched alkyl group having 1 to 12 carbon atoms.

[0114] As R 1 and R 2 Examples of monovalent aromatic hydrocarbon groups shown include phenyl, naphthyl, anthraceneyl, tetraphenyl, pentaphenyl, phenanthrene, etc. Aryl groups with 6 to 18 carbon atoms, such as benzo[a]phenanthrene, tetraphenyl, pyrene, peryl, benzo[a]phenyl, and biphenyl; aralkyl groups with 7 to 18 carbon atoms, such as benzyl, phenylethyl, and naphthylmethyl; and arylalkoxy groups such as phenoxyethyl, phenoxydiethylene glycol, and phenoxypolyalkylene glycol, preferably aryl groups with 6 to 18 carbon atoms, and are phenyl or benzyl.

[0115] As R 1 and R 2Examples of electron-donating groups include hydroxyl groups; alkoxy groups with 1 to 25 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, 2-ethylhexoxy, and 4-butyloctoxy; alkylthio groups with 1 to 12 carbon atoms, such as methylthio, ethylthio, propylthio, butylthio, pentoxy, and hexylthio; and amino groups, such as amino, monomethylamino, monoethylamino, dimethylamino, diethylamino, and methylethylamino, which can be substituted by one or two alkyl groups with 1 to 6 carbon atoms.

[0116] As R 1 and R 2 Examples of heterocyclic groups shown include pyrrolidine cyclic group, piperidine cyclic group, pyrrolin cyclic group, imidazoline cyclic group, imidazoline cyclic group, oxazoline cyclic group, thiazoline cyclic group, piperidine cyclic group, morpholine cyclic group, piperazine cyclic group, indole cyclic group, isoindole cyclic group, quinoline cyclic group, thiophene cyclic group, pyrrole cyclic group, thiazoline cyclic group, furan cyclic group, tetrahydrofuran cyclic group, etc., which are aliphatic heterocyclic groups with 4 to 20 carbon atoms or aromatic heterocyclic groups with 3 to 20 carbon atoms.

[0117] As R 1 and R 2 The polyoxyalkylene groups shown are those containing oxyethylidene (-CH2CH2O-), oxypropyl (-CH2CH2CH2O-), etc. More specifically, -(X 11 O)mR 11 The group shown (X) 11 R represents an alkylene group having 1 to 6 carbon atoms. 11 This indicates an alkyl group with 1 to 6 carbon atoms that can have hydroxyl groups, where m represents an integer from 1 to 6.

[0118] As R 1 and R 2 Examples of electron-withdrawing groups include halogen atoms, nitro groups, cyano groups, carboxyl groups, haloalkyl groups, haloaryl groups, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, and groups represented by formula (z-1).

[0119] —X 1 -R 222 (z-1)

[0120] In equation (z-1), R 222 It can represent hydrogen atoms, halogen atoms, hydrocarbon groups that may have substituents, and groups with polyoxyalkylene groups.

[0121] X 1 This indicates -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO2-, -NR 223CO- or -CONR 224 -.

[0122] R 223 and R 224 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.

[0123] * represents a bond.

[0124] As the halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom can be mentioned.

[0125] As the halogenated alkyl group, a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro-sec-butyl group, a perfluoro-tert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a dichloromethyl group, a bromomethyl group, an iodomethyl group and the like halogenated alkyl groups having 1 to 25 carbon atoms can be mentioned. Preferably, a halogenated alkyl group having 1 to 12 carbon atoms, more preferably a fluoroalkyl group having 1 to 12 carbon atoms, further preferably a perfluoroalkyl group having 1 to 12 carbon atoms.

[0126] As the halogenated aryl group, a fluorophenyl group, a chlorophenyl group, a bromophenyl group and the like halogenated aryl groups having 6 to 18 carbon atoms can be mentioned, preferably a fluoroaryl group having 6 to 18 carbon atoms, more preferably a perfluoroaryl group having 6 to 12 carbon atoms, further preferably a pentafluorophenyl group.

[0127] X 1 Preferably, -CO-, -COO- or -SO2-.

[0128] As the R 222 As the halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom can be mentioned.

[0129] As the R 222 As the hydrocarbon group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms and the like can be mentioned.

[0130] As the aliphatic hydrocarbon group having 1 to 25 carbon atoms, a straight chain, branched chain, cyclic alkyl group having 1 to 25 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an n-hexyl group, a 1-methylbutyl group, a 3-methylbutyl group, an n-octyl group, an n-decyl group, a 2-hexyloctyl group, a 4-butyloctyl group, a cyclohexyl group; an unsaturated aliphatic hydrocarbon group such as a vinyl group, a propenyl group, a butenyl group, a pentenyl group, an ethynyl group, a propynyl group, an allyl group, a cyclohexenyl group, a butadienyl group and the like, preferably an alkyl group having 1 to 12 carbon atoms.

[0131] As the aromatic hydrocarbon group having 6 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group; an aralkyl group having 7 to 18 carbon atoms such as a benzyl group, a phenylethyl group, a naphthylmethyl group and the like can be mentioned.

[0132] As R 222 The hydrocarbon group shown may have substituents, such as halogen atoms, hydroxyl groups, alkoxy groups, thioalkyl groups, and dialkylamino groups.

[0133] As R 222 The groups shown have polyoxyalkylene groups, and examples of groups similar to R can be cited. 1 The groups shown are the same as those with polyoxyalkylene groups.

[0134] As R 223 and R 224 Examples of alkyl groups having 1 to 6 carbon atoms include straight-chain or branched alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, and 1-methylbutyl.

[0135] The groups represented by formula (z-1) are preferably -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 or halogen atom that can have substituents.

[0136] More preferably, -CO-R1, -CO-O-R2, or -SO2-R9,

[0137] Further preferred is -SO2-R9,

[0138] A further preferred option is -SO2-R 10 (R 10 These can be aromatic hydrocarbon groups with 6 to 18 carbon atoms that can have substituents, such as -SO2CF3, -SO2CHF2, and -SO2CH2F.

[0139] Selected from R 1 and R 2 At least one of them is preferably an electron-withdrawing group, more preferably a cyano, nitro, haloalkyl, haloaryl, -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 or halogen atom that can have substituents. (e.g., -OCF3 or -SCF3)

[0140] Further preferred are cyano, nitro, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -SO2-R9,

[0141] Further preferred are cyano, nitro, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -SO2-R9, 10 ,

[0142] More particularly preferred are cyano or nitro.

[0143] R 3 , R 4 , R 5 and R 6 The monovalent substituent represented by R 1 The monovalent substituent represented by R

[0144] At least one selected from R 3 , R 4 , R 5 and R 6 is preferably an electron-withdrawing group,

[0145] More preferred are cyano, nitro, haloalkyl, haloaryl, -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, R 3z , R4, R5, R6, R7, R8and R9each independently represent a hydrocarbon group which can have a substituent or a halogen atom.), -OCF3or -SCF3,

[0146] Further preferred are cyano, nitro, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -SO2-R9,

[0147] More preferred are cyano, nitro, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -SO2-R9, 10 ,

[0148] More particularly preferred are cyano or nitro.

[0149] R 3 , R 4 , R 5 and R 6 each independently are preferably an electron-withdrawing group.

[0150] R 3 , R 4 , R 5 and R 6 are each independently more preferably cyano, nitro, haloalkyl, haloaryl, -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, R 3z , R4, R5, R6, R7, R8and R9each independently represent a hydrocarbon group which can have a substituent or a halogen atom.), -OCF3or -SCF3,

[0151] further preferably cyano, nitro, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -SO2-R9,

[0152] more further preferably cyano, nitro, -OCF3, -SCF3, -SF5, -SO2CF3, -SO2-R 10 ,

[0153] more particularly preferably cyano or nitro.

[0154] R 1 and R 4 may be linked to each other to form a ring. R 1 and R 4 linked to each other to form a ring, the ring W 1 and the ring W 4 linked to each other to form a ring, the ring W 1 and the ring W 2 form a fused ring of at least 3 rings or more. Anions represented by formula (I) having a fused ring formed by R 1 and R 4 linked to each other to form a ring, the ring W 1 and the ring W 2 include, for example, the following anions.

[0155]

[0156] having a fused ring formed by R 1 and R 4 linked to each other to form a ring, the ring W 1 and the ring W 2The anion represented by formula (I) formed by the condensed ring preferably is an anion represented by formula (I-W2), formula (I-W3), formula (I-W4), formula (I-W5), formula (I-W6), formula (I-W7), or formula (I-W14).

[0157] R 1 R 4 The ring formed by the mutual bonding of R 1 R 2 may have the same group as the substituents that ring W 2 and ring W 6 may have.

[0158] R 2 R 6 The ring formed by the mutual bonding of R 2 R 6 may have the same group as the substituents that ring W 1 and ring W 2 form a condensed ring of at least 3 rings or more. The anion represented by formula (1) having a condensed ring formed by the mutual bonding of R 2 R 6 may have the same group as the substituents that ring W 1 and ring W 2 for example, can be an anion represented by the following.

[0159]

[0160] The anion represented by formula (I) having a condensed ring formed by the mutual bonding of R 2 R 6 may have the same group as the substituents that ring W 1 and ring W 2 for example, can be an anion represented by formula (I-w2), formula (I-w3), formula (I-w4), formula (I-w5), formula (I-w6), formula (I-w7), or formula (I-w14).

[0161] R 2 R 6 The ring formed by the mutual bonding of R 1 R 2 may have the same group as the substituents that ring W 3 and ring W 4 may have.

[0162] R 3 R 4 The ring formed by the mutual bonding of R 3 R 4The rings formed by the combination of atoms can contain heteroatoms (nitrogen atoms, oxygen atoms, sulfur atoms, etc.) as the constituent elements of the ring.

[0163] R 3 With R 4 The rings formed by mutual bonding are usually 3 to 10-membered rings, preferably 5 to 7-membered rings, and more preferably 5-membered or 6-membered rings.

[0164] As R 3 With R 4 The rings formed by mutual bonding can be exemplified by the rings described below.

[0165] The asterisk (*) in the following description of the ring indicates a connection to the ring W. 1 The connection key.

[0166]

[0167] R 3 With R 4 The rings formed by mutual bonding are preferably the rings shown in formula (w-1), formula (w-4), formula (w-5), formula (w-6), formula (w-8), formula (w-9), formula (w-10), formula (w-11), formula (w-13), formula (w-31), formula (w-32), formula (w-35), formula (w-36), formula (w-37), formula (w-45), formula (w-47), or formula (w-48).

[0168] As R 5 With R 6 A loop formed by interconnected links can be exemplified by R. 3 With R 4 A ring formed by interconnected links. R 5 With R 6 The rings formed by interconnection are preferably the rings shown in formulas (w-1), (w-4), (w-5), (w-6), (w-8), (w-9), (w-10), (w-11), (w-13), (w-31), (w-32), (w-35), (w-36), (w-37), (w-45), (w-47), or (w-48).

[0169] The anion represented by formula (I) is more preferably the anion represented by formula (IA).

[0170]

[0171] In formula (IA), R 1 ~R 6 Each can independently express the same meaning as described above.

[0172] Anions represented by formula (I) include, for example, the following anions. Note that Me in the formula represents a methyl group.

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] The compound of the present application is composed of an anion represented by formula (I) and a counter cation. The combination of the anion represented by formula (I) and the cation in the compound of the present application is not limited.

[0190] The cation can be an organic cation or an inorganic cation.

[0191] ​As the organic cation, there can be mentioned 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, 1,1'-dibenzyl-4,4'-bipyridinium, and the like;

[0192] 1-butyl-1-methylpiperidinium, 1-methyl-1-propylpiperidinium, and the like piperidinium cations;

[0193] 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, 1-methyl-1-pentylpyrrolidinium, and the like pyrrolidinium cations;

[0194] 2-methyl-1-pyrrolinium, and the like cations having a pyrroline skeleton;

[0195] 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, 1-butyl-3-methylimidazolium, and the like imidazolium cations;

[0196] ammonium cations such as pentyltriethylammonium, butyltrimethylammonium, benzyl(ethyl)dimethylammonium, cyclohexyltrimethylammonium, diethyl(methyl)propylammonium, diethyl(2-methoxyethyl)methylammonium, ethyl(2-methoxyethyl)dimethylammonium, ethyl(dimethyl)(2-phenylethyl)ammonium, methyltri(n-octyl)ammonium, tetrabutylammonium, tetrahexylammonium, tetrapentylammonium, tetra-n-octylammonium, tetraheptylammonium, tetrapropylammonium, and the like;

[0197] triethylsulfonium, and the like trialkylsulfonium cations;

[0198] phosphonium cations such as tributylhexadecylphosphonium, tributylmethylphosphonium, tributyl-n-octylphosphonium, tributyl-n-octylphosphonium, tetra-n-octylphosphonium, tributyl(2-methoxyethyl)phosphonium, tributylmethylphosphonium, trihexyl(tetradecyl)phosphonium, trihexyl(tetradecyl)phosphonium, and the like.

[0199] 4-ethyl-4-methylmorpholinium and the like morpholinium cations;

[0200] triphenylmethylphosphonium and the like triarylmethane cations and the like.

[0201] As the inorganic cation, there can be mentioned 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 and zinc 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; NH4 + and the like.

[0202] The cation is preferably an alkali metal ion, an alkaline earth metal ion, copper (I) ion, copper (II) ion, nickel ion, cobalt (III) ion, iron (II) ion, iron (III) ion, palladium ion and an organic cation, more preferably potassium ion, calcium ion, barium ion, magnesium ion, copper (I) ion, copper (II) ion, nickel ion and an organic cation, and further preferably potassium ion and an organic cation.

[0203] In the compound (I), the combination of the anion and the cation represented by the formula (I) is not limited, and the compound represented by the formula (IA) is preferred.

[0204]

[0205] [In the formula (IA), W 1 , W 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent the same meaning as described above.

[0206] g represents an integer of 1 to 4.

[0207] G represents a monovalent cation, a divalent cation, a trivalent cation or a tetravalent cation.

[0208] The molecular weight of the compound (I) is preferably 3000 or less, more preferably 2000 or less, and further preferably 1000 or less. In addition, it is preferably 100 or more, more preferably 200 or more, and further preferably 300 or more.

[0209] Compound (I) preferably shows an absorption maximum at a wavelength of 450 nm to a wavelength of 650 nm.

[0210] The molar extinction coefficient ε at the absorption maximum wavelength (λmax) of compound (I) 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. The upper limit is not particularly limited, and is usually 100000 [L / (g-cm)] or less.

[0211] If the molar extinction coefficient ε at the λmax of compound (I) is 50 [L / (g-cm)] or more, light around the absorption maximum wavelength can be efficiently absorbed, which is preferable from this aspect.

[0212] The full width at half maximum of compound (I) is preferably 45 nm or less, more preferably 40 nm, further 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.

[0213] As compound (I), for example, the compounds described in Tables 1 to 6 below can be given. Compound (1) has an anion represented by formula (I-1) and a lithium ion, and represents the structure described below.

[0214]

[0215] [Table 1]

[0216] Compound (I) Anion-(1) Cation-(1) Anion-(2) Anion-(3) Anion-(4) Compound (1) Formula (I-1) Lithium ion Compound (2) Formula (I-1) Sodium ion Compound (3) Formula (I-1) Potassium ion Compound (4) Formula (I-1) Rubidium ion Compound (5) Formula (I-1) Cesium ion Compound (6) Formula (I-1) Beryllium ion Formula (I-1) Compound (7) Formula (I-1) Magnesium ion Formula (I-1) Compound (8) Formula (I-1) Calcium ion Formula (I-1) Compound (9) Formula (I-1) Barium ion Formula (I-1) Compound (10) Formula (I-1) Titanium ion Formula (I-1) Formula (I-1) Formula (I-1) Compound (11) Formula (I-1) Zirconium ion Formula (I-1) Formula (I-1) Formula (1-1) Compound (12) Formula (I-1) Vanadium ion Formula (I-1) Formula (I-1) Formula (I-1) Compound (13) Formula (I-1) Iron(I) ion Compound (14) Formula (I-1) Iron(II) ion Formula (I-1) Compound (15) Formula (I-1) Cobalt ion Formula (I-1) Compound (16) Formula (I-1) Nickel ion Formula (I-1) Compound (17) Formula (I-1) Copper(I) ion Compound (18) Formula (I-1) Copper(II) ion Formula (I-1) Compound (19) Formula (I-1) Silver ion Compound (20) Formula (I-1) Zinc ion Formula (I-1) Compound (21) Formula (I-1) Aluminum ion Formula (I-1) Formula (I-1) Compound (22) Formula (I-1) Gallium ion Formula (I-1) Formula (I-1) Compound (23) Formula (I-1) Indium ion Formula (I-1) Formula (I-1) Compound (24) Formula (I-1) N-octyl-4-methylpyridinium Compound (25) Formula (I-1) 1-butyl-1-methylpiperidinium Compound (26) Formula (I-1) 1-ethyl-1-methylpyrrolidinium Compound (27) Formula (I-1) 1-butyl-2.3-dimethylimidazolium Compound (28) Formula (I-1) Tetrabutylammonium Compound (29) Formula (I-1) Tributylmethylphosphonium Compound (30) Formula (I-1) Tetraphenylphosphonium

[0217] [Table 2]

[0218] Compound (Ⅰ) Anion-(1) Cation-(1) Anion-(2) Compound (31) Formula (I-318) Potassium ion Compound (32) Formula (I-2) Potassium ion Compound (33) Formula (I-1) Copper(II) ion Formula (I-2) Compound (34) Formula (I-1) 11'-dimethyl-44'-chrysidinium Formula (I-2) Compound (35) Formula (I-3) Potassium ion Compound (36) Formula (I-4) Potassium ion Compound (37) Formula (I-8) Potassium ion Compound (38) Formula (I-9) Potassium ion Compound (39) Formula (I-10) Potassium ion Compound (40) Formula (I-11) Potassium ion Compound (41) Formula (I-12) Potassium ion Compound (42) Formula (I-13) Potassium ion Compound (43) Formula (I-14) Potassium ion Compound (44) Formula (I-15) Potassium ion Compound (45) Formula (I-16) Potassium ion Compound (46) Formula (I-17) Potassium ion Compound (47) Formula (I-18) Potassium ion Compound (48) Formula (I-19) Potassium ion Compound (49) Formula (I-20) Potassium ion Compound (50) Formula (I-21) Potassium ion Compound (51) Formula (I-22) Potassium ion Compound (52) Formula (I-24) Potassium ion Compound (53) Formula (I-27) Potassium ion Compound (54) Formula (I-39) Potassium ion Compound (55) Formula (I-42) Potassium ion Compound (56) Formula (I-43) Potassium ion Compound (57) Formula (I-45) Potassium ion Compound (58) Formula (I-46) Potassium ion Compound (59) Formula (I-48) Potassium ion Compound (60) Formula (I-49) Potassium ion

[0219] [Table 3]

[0220] Compound (I) Anion-(1) Cation-(1) Compound (61) Formula (I-51) Potassium ion Compound (62) Formula (I-52) Potassium ion Compound (63) Formula (I-54) Potassium ion Compound (64) Formula (I-55) Potassium ion Compound (65) Formula (I-57) Potassium ion Compound (66) Formula (I-58) Potassium ion Compound (67) Formula (I-60) Potassium ion Compound (68) Formula (I-61) Potassium ion Compound (69) Formula (I-83) Potassium ion Compound (70) Formula (I-84) Potassium ion Compound (71) Formula (I-85) Potassium ion Compound (72) Formula (I-90) Potassium ion Compound (73) Formula (I-91) Potassium ion Compound (74) Formula (I-93) Potassium ion Compound (75) Formula (I-94) Potassium ion Compound (76) Formula (I-96) Potassium ion Compound (77) Formula (I-97) Potassium ion Compound (78) Formula (I-99) Potassium ion Compound (79) Formula (I-100) Potassium ion Compound (80) Formula (I-102) Potassium ion Compound (81) Formula (I-104) Potassium ion Compound (82) Formula (I-106) Potassium ion Compound (83) Formula (I-108) Potassium ion Compound (84) Formula (I-110) Potassium ion Compound (85) Formula (I-114) Potassium ion Compound (86) Formula (I-116) Potassium ion Compound (87) Formula (I-118) Potassium ion Compound (88) Formula (I-120) Potassium ion Compound (89) Formula (I-122) Potassium ion Compound (90) Formula (I-124) Potassium ion Compound (91) Formula (I-126) Potassium ion Compound (92) Formula (I-128) Potassium ion Compound (93) Formula (I-130) Potassium ion Compound (94) Formula (I-132) Potassium ion Compound (95) Formula (I-134) Potassium ion Compound (96) Formula (I-136) Potassium ion Compound (97) Formula (I-138) Potassium ion Compound (98) Formula (I-140) Potassium ion Compound (99) Formula (I-171) Potassium ion Compound (100) Formula (I-172) Potassium ion

[0221] [Table 4]

[0222] Compound (I) Anion-(1) Cation-(1) Compound (101) Formula (I-173) potassium ions Compound (102) Formula (I-174) potassium ions Compound (103) Formula (I-176) potassium ions Compound (104) Formula (I-178) potassium ions Compound (105) Formula (I-179) potassium ions Compound (106) Formula (I-180) potassium ions Compound (107) Formula (I-181) potassium ions Compound (108) Formula (I-182) potassium ions Compound (109) Formula (I-183) potassium ions Compound (11O) Formula (I-220) potassium ions Compound (111) Formula (I-221) potassium ions Compound (112) Formula (I-222) potassium ions Compound (113) Formula (I-223) potassium ions Compound (114) Formula (I-224) potassium ions Compound (115) Formula (I-225) potassium ions Compound (116) Formula (I-226) potassium ions Compound (117) Formula (I-227) potassium ions Compound (118) Formula (I-228) potassium ions Compound (119) Formula (I-229) potassium ions Compound (120) Formula (I-230) potassium ions Compound (121) Formula (I-231) potassium ions Compound (122) Formula (I-232) potassium ions Compound (123) Formula (I-233) potassium ions Compound (124) Formula (I-234) potassium ions Compound (125) Formula (I-235) potassium ions Compound (126) Formula (I-236) potassium ions Compound (127) Formula (I-237) potassium ions Compound (128) Formula (I-238) potassium ions Compound (129) Formula (I-239) potassium ions Compound (130) Formula (I-240) potassium ions Compound (131) Formula (I-241) potassium ions Compound (132) Formula (I-242) potassium ions Compound (133) Formula (I-243) potassium ions Compound (134) Formula (I-244) potassium ions Compound (135) Formula (I-245) potassium ions Compound (136) Formula (I-246) potassium ions Compound (137) Formula (I-247) potassium ions Compound (138) Formula (I-248) potassium ions Compound (139) Formula (I-249) potassium ions Compound (140) Formula (I-250) potassium ions

[0223] [Table 5]

[0224] Compound (I) Anion-(1) Cation-(1) Compound (141) Formula (I-251) potassium ions Compound (142) Formula (I-252) potassium ions Compound (143) Equation (I-253) potassium ions Compound (144) Formula (I-254) potassium ions Compound (145) Formula (I-255) potassium ions Compound (146) Formula (I-256) potassium ions Compound (147) Formula (I-257) potassium ions Compound (148) Formula (I-258) potassium ions Compound (149) Formula (I-259) potassium ions Compound (150) Formula (I-260) potassium ions Compound (151) Formula (I-261) Potassium ion Compound (152) Formula (I-262) Potassium ion Compound (153) Formula (I-263) Potassium ion Compound (154) Formula (I-264) Potassium ion Compound (155) Formula (I-265) Potassium ion Compound (156) Formula (I-266) Potassium ion Compound (157) Formula (I-267) Potassium ion Compound (158) Formula (I-268) Potassium ion Compound (159) Formula (I-269) Potassium ion Compound (160) Formula (I-270) Potassium ion Compound (161) Formula (I-271) Potassium ion Compound (162) Formula (I-272) Potassium ion Compound (163) Formula (I-273) Potassium ion Compound (164) Formula (I-274) Potassium ion Compound (165) Formula (I-275) Potassium ion Compound (166) Formula (I-276) Potassium ion Compound (167) Formula (I-277) Potassium ion Compound (168) Formula (I-278) Potassium ion Compound (169) Formula (I-279) Potassium ion Compound (170) Formula (I-280) Potassium ion Compound (171) Formula (I-281) Potassium ion Compound (172) Formula (I-282) Potassium ion Compound (173) Formula (I-283) Potassium ion Compound (174) Formula (I-284) Potassium ion Compound (175) Formula (I-285) Potassium ion Compound (176) Formula (I-286) Potassium ion Compound (177) Formula (I-287) Potassium ion Compound (178) Formula (I-288) Potassium ion Compound (179) Formula (I-289) Potassium ion Compound (180) Formula (I-290) Potassium ion

[0225] [Table 6]

[0226] Compound (I) Anion-(1) Cation-(1) Compound (181) Formula (I-291) Potassium ion Compound (182) Formula (I-292) Potassium ion Compound (183) Formula (I-293) Potassium ion Compound (184) Formula (I-294) Potassium ion Compound (185) Formula (I-295) Potassium ion Compound (186) Formula (I-296) Potassium ion Compound (187) Formula (I-297) Potassium ion Compound (188) Formula (I-298) Potassium ion Compound (189) Formula (I-299) Potassium ion Compound (190) Formula (I-300) Potassium ion Compound (191) Formula (I-301) Potassium ion Compound (192) Formula (I-310) Potassium ion Compound (193) Formula (I-312) Potassium ion Compound (194) Formula (I-313) Potassium ion Compound (195) Formula (I-314) Potassium ion Compound (196) Formula (I-315) Potassium ion Compound (197) Formula (I-316) Potassium ion Compound (198) Formula (I-317) Potassium ion

[0227] Compound (I) is preferably 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) to Compound (112), Compound (114) to Compound (121), Compound (123) to Compound (129), Compound (132), Compound (133), Compound (135) to Compound (138), Compound (140) to Compound (143), Compound (145) to Compound (147), Compound (149) to Compound (155), Compound (158), Compound (159), Compound (161) to Compound (164), Compound (166) to Compound (169), Compound (171) to Compound (173), Compound (175), Compound (176), Compound (179) to Compound (181), Compound (184), Compound (185), Compound (187) to Compound (189), Compound (191), Compound (193) to Compound (198).

[0228] <Method for producing compound (I) (1)>

[0229] 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)).

[0230]

[0231] [in formula (M1-1), ring W 1 , ring W 2 , R 3 , R 4 , R 5 , and R6 represents the same meaning as described above.

[0232] In formula (M1-2), R 2’ represents a monovalent substituent, and E1represents a leaving group.

[0233] In formula (M1-3), R 1’ represents a monovalent substituent, and E2represents a leaving group.

[0234] R 2’ The monovalent substituent represented by R 2 may be the same group as the monovalent substituent represented by R

[0235] R 1’ The monovalent substituent represented by R 1 may be the same group as the monovalent substituent represented by R

[0236] As the leaving groups represented by E1and E2, each independently, can be mentioned a halogen atom, a succinimide group, a maleimide group, an o-sulfobenzoylimide group, a methylsulfonyl group, a p-methoxybenzenesulfonyl group, a p-toluenesulfonyl group, a trifluoromethylsulfonyl group, a nonafluorobutanesulfonyl group, and the like.

[0237] The reaction of at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1) 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).

[0238] The amount of use of compound (M1-2) is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, relative to 1 mole of compound (M1-1).

[0239] The amount of use of compound (M1-3) is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, relative to 1 mole of compound (M1-1).

[0240] The reaction of at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1) is preferably carried out in the presence of a base.

[0241] As the base, metal alkoxides (alkali metal alkoxides are preferred) such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tert-butoxide, potassium tert-butoxide, and the like; metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like; metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride, sodium borohydride, and the like; metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, lithium carbonate, lithium bicarbonate, cesium carbonate, and the like; organolithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, phenyllithium, and the like; alkyl metal halides such as methylmagnesium bromide, isopropylmagnesium bromide, n-butyllmagnesium bromide, isopropylmagnesium chloride, and the like; metal amide compounds such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, lithium tetramethylpiperidide, and the like; 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, ethylenediamine, and the like; metal carboxylates such as sodium acetate, potassium acetate, sodium formate, and the like; ammonium carboxylate salts such as ammonium acetate, and the like.

[0242] The amount of the base used is usually 0.001 to 20 moles, preferably 0.03 to 10 moles, more preferably 0.05 to 5 moles, further preferably 0.1 to 3 moles, and particularly preferably 0.5 to 2 moles, per 1 mole of the compound (M1-1).

[0243] 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) can be carried out in the presence of a solvent.

[0244] As the solvent, there can be mentioned acetonitrile, benzonitrile and the like nitrile solvents; benzene, toluene, xylene, anisole and the like aromatic hydrocarbon solvents; n-hexane, n-heptane, cyclohexane, methylcyclohexane and the like aliphatic hydrocarbon solvents; chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, chloroform and the like halogen solvents; methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, n-propyl acetate and the like ester solvents; methanol, ethanol, isopropanol, hexafluoroisopropanol, n-butanol, isobutanol, tert-butanol and the like alcohol solvents; acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone and the like ketone solvents; tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentyl methyl ether, 4-methyltetrahydropyran, dioxane, diethyl ether, tert-butyl methyl ether, diisopropyl ether, dimethoxyethane, diethoxy methane and the like ether solvents; N,N-dimethylacetamide, N,N-dimethylformamide and the like amide solvents; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; hexamethylphosphoric triamide; water and the like. The solvent is preferably a nitrile solvent, an alcohol solvent, an ether solvent, a ketone solvent, an aromatic hydrocarbon solvent, more preferably acetonitrile, tetrahydrofuran, diethyl ether, methanol, ethanol, isopropanol, 2-butanone or toluene, further preferably acetonitrile, tetrahydrofuran, methanol, ethanol, isopropanol, 2-butanone, toluene, particularly preferably methanol, ethanol, isopropanol, acetonitrile, 2-butanone or toluene.

[0245] The reaction time of at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1) is usually 0.01 to 200 hours.

[0246] The reaction temperature of at least one compound selected from the group consisting of compound (M1-2) and compound (M1-3) with compound (M1-1) is usually -100 to 200°C.

[0247] As the compound (M1-1), there can be mentioned the compounds described below and the like.

[0248]

[0249] As the compound (M1-2) and the compound (M1-3), commercially available products can be used. For example, mention can be made of cyanogen chloride, cyanogen bromide, p-toluenesulfonyl cyanide, trifluoromethanesulfonyl cyanide, benzyl thiocyanate, tert-butyl isocyanide, copper (I) cyanide, potassium cyanide, 1-cyano-4-(dimethylamino) pyridine tetrafluoroborate, p-toluenesulfonylmethyl isocyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane di(tetrafluoroborate) (also called Selectfluor (registered trademark of Air Products and Chemicals)), benzoyl(phenyl iodide)(trifluoromethanesulfonyl)methanide (Japanese: benzoil(phenyl iodonio)(trifluoromethanesulfonyl) methanide), 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate, 1-fluoro-3,3-dimethyl-1,2-benziodoxolane (Japanese: 1-fluoro-3,3-dimethyl-1,2-benziodoxolane), N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide, tetramethylammonium tribromide, fluorine (F2), bromine (Br2), chlorine (Cl2), iodine (I2), N-bromophthalimide, N-chlorophthalimide, N-iodophthalimide, N-bromosaccharin, N-(trifluoromethylthio)saccharin, N-(trifluoromethylthio)saccharin, N-(trifluoromethylthio)aniline, N-methyl-N-[(trifluoromethyl)thio]-p-toluenesulfonamide, 1-trifluoromethyl-3,3-dimethyl-1,2-benziodoxolane, 1-trifluoromethyl-1,2-benziodoxolane-3(1H)-one, nitric acid, iodomethane, dimethyl sulfate, methyl trifluoromethanesulfonate, ethyl trifluoromethanesulfonate, n-butyl trifluoromethanesulfonate, acetyl chloride, and the like.

[0250] Note that, in R 1’ is the same group as R 2’ is the same group as R

[0251] If at least one compound selected from the compound (M1-2) and the compound (M1-3) is allowed to react with the compound (M1-1), a compound (I) having a cation from the compound (M1-1) and an anion represented by the formula (I) can be obtained.

[0252] In the case where the cation of the compound (I) is desired to be exchanged for a desired cation, the ion exchange can be performed by mixing the compound (I) with a salt having the desired cation. The above ion exchange can be performed in the presence of a solvent. The salt having the desired cation can be exemplified by a chloride salt containing the desired cation and a chloride ion, a bromide salt containing the desired cation and a bromide ion, an iodide salt containing the desired cation and an iodide ion, a fluoride salt containing the desired cation and a fluoride ion, a nitrate salt containing the desired cation and a nitrate ion, a sulfate salt containing the desired cation and a sulfate ion, a perchlorate salt containing the desired cation and a perchlorate ion, a sulfonic acid salt containing the desired cation and a sulfonic acid ion, a carboxylic acid salt containing the desired cation and a carboxylic acid ion, a hypochlorite salt containing the desired cation and a hypochlorite ion, a hexafluorophosphate salt containing the desired cation and a hexafluorophosphate ion, an imide salt containing the desired cation and an imide ion, and the like.

[0253] Note that the compound (I) having a cation of 2 valence or more can be obtained by performing ion exchange after obtaining the compound (I) having a cation of 1 valence. Alternatively, it can be obtained by using a compound (M1-1) having a cation of 2 valence or more at the time of reacting at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) with the compound (M1-1).

[0254] The anion portion in the compound (M1-1) can be produced by reacting a compound represented by the formula (M1-4) (hereinafter, sometimes referred to as the compound (M1-4)), a compound represented by the formula (b-2) (hereinafter, sometimes referred to as the compound (b-2)), and a compound represented by the formula (b-3) (hereinafter, sometimes referred to as the compound (b-3)).

[0255]

[0256] [In the formula (M1-4), the ring W 1 and the ring W 2 represent the same meanings as described above.

[0257] In the formula (b-2), R 3 and R 4 represent the same meanings as described above, and X1 represents a 2-valent linking group.

[0258] In the formula (b-3), R 5 and R 6 represent the same meanings as described above, and X2 represents a 2-valent linking group.

[0259] The reaction of the compound (Ml-4) with the compound (b-2) with the compound (b-3) is carried out by mixing the compound (Ml-4) with the compound (b-2) with the compound (b-3).

[0260] The reaction of the compound (Ml-4) with the compound (b-2) with the compound (b-3) is preferably carried out in the presence of a base, and preferably the compound (Ml-4) is mixed with the compound (b-2) with the compound (b-3) with the base.

[0261] The mixing of the compound (Ml-4) with the compound (b-2) with the compound (b-3) with the base is preferably carried out by adding the compound (b-2) to a mixture (1) of the compound (Ml-4) with a part of the base to obtain a mixture (2), and adding a mixture (3) of the compound (b-3) with the remaining part of the base to the obtained mixture (2).

[0262] The reaction of the compound (Ml-4) with the compound (b-2) with the compound (b-3) with the base can be carried out in the presence of a solvent. As the solvent, the same solvent as that which can be used at the time of the reaction of at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3) with the compound (Ml-l) can be cited. Acetonitrile, ethanol, methanol, 2-butanone, toluene, 2-butanone, tetrahydrofuran, dioxane are preferred.

[0263] Further, the solvent is preferably a dehydrated solvent.

[0264] The reaction time of the compound (Ml-4) with the compound (b-2) with the compound (b-3) with the base is usually 0.05 to 100 hours.

[0265] The reaction temperature of the compound (Ml-4) with the compound (b-2) with the compound (b-3) with the base is usually -100 to 200°C.

[0266] The amount of use of the compound (b-2) is usually 0.01 to 10 moles per 1 mole of the compound (Ml-4).

[0267] The amount of use of the compound (b-3) is usually 0.01 to 10 moles per 1 mole of the compound (Ml-4).

[0268] The amount of use of the base is usually 0.01 to 10 moles per 1 mole of the compound (Ml-4).

[0269] As the compound (Ml-4), a commercially available product can be used, and 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one and the like can be cited.

[0270] The compound (b-2) and the compound (b-3) can each independently be used as a commercially available product, 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, pivaloyl cyanide, cyanoacetohydrazide, benzoyl cyanide, 2-cyanoacetanilide, 3-oxo-3-(2-thienyl)propionitrile, methyl acetoacetate, dimethyl ketone, 1,3-cyclopropanedione, tetronic acid, acetylacetone, malondiamide, malonic acid, 1,3-cyclohexanedione, 2,4-piperidinedione, 1,3-cycloheptanedione, barbituric acid, 3,5-heptanedione, dimethyl malonate, mel drum 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.

[0271] Note that, in the case where X1and X2are the same group, R 3 and R 4 are the same group, and R 5 and R 6 are the same group, the compound (b-2) and the compound (b-3) are the same compound.

[0272] As the base, the same base as that which can be used in the reaction of at least one compound selected from the group consisting of the compound (M1-2) and the compound (M1-3) and the compound (M1-1) can be used.

[0273] The compound (M1-1) generally has a cation derived from a base. For example, if the cation derived from the base is monovalent, a compound containing a monovalent cation and one anion represented by the formula (M1-1) can be obtained. If the cation derived from the base is divalent, a compound containing a divalent cation and two anions represented by the formula (M1-1) can be obtained.

[0274] <Method for producing the compound (I) (2)>

[0275] The anion portion of the compound (I) can also be produced by reacting a compound represented by the formula (M-A) (hereinafter, sometimes referred to as the compound (M-A)) and the compound (b-3).

[0276]

[0277] [In the formula, R 1 , R 2 , R 3 , R 4, R 5 , R 6 , X2, W 1 and W 2 respectively represent the same meanings as described above.

[0278] The reaction of the compound (M-A) with the compound (b-3) is preferably carried out in the presence of a catalyst.

[0279] As the catalyst, there can be mentioned carboxylic acids such as formic acid, acetic acid, trifluoroacetic acid; ammonium chloride; Lewis acids such as titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride, lanthanum triflate; sulfonic acid anhydrides such as methanesulfonic acid anhydride, p-toluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, nonafluorobutanesulfonic acid anhydride; sulfonic acids such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid; electrophilic alkylating agents such as dimethyl sulfate, methyl trifluoromethanesulfonate (methyl triflate), iodomethane, trimethyloxosulfonium tetrafluoroborate, dimethyl fluorosulfate; and sulfonic acid halides such as p-toluenesulfonyl chloride, trifluoromethanesulfonyl chloride. Preferred are electrophilic alkylating agents, sulfonic acid anhydrides or sulfonic acid halides, more preferred are dimethyl sulfate, methyl trifluoromethanesulfonate, p-toluenesulfonic acid anhydride or trifluoromethanesulfonic acid anhydride, p-toluenesulfonyl chloride or trifluoromethanesulfonyl chloride, and further preferred are methyl trifluoromethanesulfonate or trifluoromethanesulfonic acid anhydride.

[0280] The reaction of the compound (M-A) with the compound (b-3) is preferably carried out in the presence of a base.

[0281] As the base, there can be mentioned the same bases as those which can be used in 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).

[0282] The reaction of the compound (M-A) with the compound (b-3) can be carried out in the presence of a solvent. As the solvent, there can be mentioned the same solvents as those which can be used in 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).

[0283] Further, the solvent is preferably a dehydrating solvent.

[0284] The reaction of the compound (M-A) with the compound (b-3) is preferably carried out by mixing the catalyst with the compound (M-A) and the compound (b-3), and more preferably by mixing the catalyst with the base with the compound (M-A) and the compound (b-3).

[0285] The reaction of the compound (M-A) with the compound (b-3) is preferably carried out under a deoxidized atmosphere (for example, under a nitrogen atmosphere).

[0286] The amount of use of the compound (b-3) is usually 0.01 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M-A).

[0287] The amount of use of the catalyst is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M-A).

[0288] The amount of use of the base is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M-A).

[0289] The reaction time of the compound (M-A) with the compound (b-3) is usually 0.01 to 200 hours.

[0290] The reaction temperature of the compound (M-A) with the compound (b-3) is usually -100 to 200°C.

[0291] As the compound (M-A), for example, the following compounds can be mentioned.

[0292]

[0293] If the compound (M-A) is allowed to react with the compound (b-3) in the presence of a base, a compound (I) having a cation from the base and an anion represented by the formula (I) can be obtained.

[0294] In the case where the cation of the compound (I) is desired to be exchanged for a desired cation, ion exchange can be performed by mixing the compound (I) with a salt having the desired cation. The above ion exchange can be performed in the presence of a solvent. The salt having the desired cation is, for example, a chloride salt containing the desired cation and a chloride ion, a bromide salt containing the desired cation and a bromide ion, an iodide salt containing the desired cation and an iodide ion, a fluoride salt containing the desired cation and a fluoride ion, a nitrate salt containing the desired cation and a nitrate ion, a sulfate salt containing the desired cation and a sulfate ion, a perchlorate salt containing the desired cation and a perchlorate ion, a sulfonic acid salt containing the desired cation and a sulfonic acid ion, a carboxylic acid salt containing the desired cation and a carboxylic acid ion, a hypochlorite salt containing the desired cation and a hypochlorite ion, a hexafluorophosphate salt containing the desired cation and a hexafluorophosphate ion, an imide salt containing the desired cation and an imide ion, and the like.

[0295] The compound (M-A) can be produced by allowing a compound represented by the formula (M) (hereinafter, sometimes referred to as a compound (M)) to react with the compound (b-2) in the presence of a catalyst.

[0296]

[0297] [In the formula, ring W 1 , ring W 2 , R 1 , R 2 , R 3 , R 4 and X1 each represent the same meaning as described above.]

[0298] As the catalyst, the same catalyst as that which can be used at the time of the reaction of the compound (M-A) with the compound (b-3) can be cited. An electrophilic alkylating agent, a sulfonic acid anhydride, or a sulfonic acid halide is preferable, and dimethyl sulfate, methyl triflate, p-toluenesulfonic acid anhydride or triflic acid anhydride, p-toluenesulfonyl chloride, triflic sulfonyl chloride is more preferable, and methyl triflate or triflic acid anhydride is further preferable.

[0299] The reaction of the compound (M) with the compound (b-2) is preferably further carried out in the presence of a base.

[0300] As the base, the same base as that which can be used at the time of 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) can be cited, and a metal alkoxide, a metal hydroxide, a metal hydride, a metal carbonate, an organic lithium, a metal amide compound, an amine compound, or a metal carboxylate is preferable, and 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, methyl lithium, n-butyllithium, tert-butyllithium, diisopropylamino lithium, 2,2,6,6-tetramethylpiperidyl lithium, (bistrimethylsilyl)amino lithium, tetramethylpiperidyl lithium, pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, sodium acetate, sodium formate, ammonium acetate is more preferable.

[0301] The reaction of the compound (M) with the compound (b-2) can be carried out in the presence of a solvent. As the solvent, the same solvent as that which can be used at the time of 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) can be cited. Acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide, or dimethylacetamide is preferable.

[0302] In addition, the solvent is preferably a dehydrated solvent.

[0303] The reaction of the compound (M) with the compound (b-2) is carried out by mixing the catalyst with the compound (M) and the compound (b-2), preferably by mixing the catalyst with the base with the compound (M) and the compound (b-2).

[0304] The reaction of the compound (M) with the compound (b-2) is preferably carried out under a deoxidized atmosphere (for example, under a nitrogen atmosphere).

[0305] The amount of use of the compound (b-2) is usually 0.01 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M).

[0306] The amount of use of the catalyst is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M).

[0307] The amount of use of the base is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M).

[0308] The reaction time of the compound (M) with the compound (b-2) is usually 0.1 to 200 hours.

[0309] The reaction temperature of the compound (M) with the compound (b-2) is usually -100 to 200°C.

[0310] <Compound (M)>

[0311] The compound (M) is a novel compound having a structure shown by the following formula, and is a synthetic intermediate of the compound (I).

[0312]

[0313] [In the formula, ring W 1 , ring W 2 , R 1 , and R 2 have the same meanings as described above.]

[0314] As the compound (M), the following compounds and the like can be given.

[0315]

[0316] <Production method of compound (M)>

[0317] The compound (M) can be produced by reacting a compound shown by the formula (M1-4) (hereinafter, sometimes referred to as compound (M1-4)) with at least one compound selected from the group consisting of the compound (M1-2) and the formula (M1-3).

[0318]

[0319] [In the formula, ring W 1 , ring W 2 , R 1 , R 2 , R 1’ , R 2’ , E1and E2represent the same meaning as described above.]

[0320] The leaving group represented by E2may be the same group as the leaving group represented by E1.

[0321] The reaction 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 preferably carried out in the presence of a base.

[0322] As the base, the same base as that which can be used at the time of 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) can be mentioned, and a metal alkoxide, a metal hydroxide, a metal hydride, a metal carbonate, an organic lithium, a metal amide compound, an amine compound or a metal carboxylate is preferable, and 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, methyl lithium, n-butyl lithium, tert-butyl lithium, diisopropyl amide lithium, 2,2,6,6-tetramethyl piperidyl lithium, (bis-trimethylsilyl) amide lithium, tetramethyl piperidyl lithium, pyridine, 2,6-dimethyl pyridine, 2,6-di-tert-butyl pyridine, triethyl amine, diisopropyl ethyl amine, triisopropyl amine, 2,2,6,6-tetramethyl piperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethyl aniline, sodium acetate, sodium formate, ammonium acetate are more preferable.

[0323] The amount of the base used is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (M1-4).

[0324] The reaction 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) can be carried out in the presence of a solvent. As the solvent, the same solvent as that which can be used at the time of 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) can be mentioned. Acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethyl sulfoxide, dimethyl formamide, dimethyl acetamide are preferable.

[0325] Further, the solvent is preferably a dehydrated solvent.

[0326] The reaction of the compound (Ml-4) with at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3) is preferably carried out by mixing the compound (Ml-4) with at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3), more preferably by mixing a base with the compound (Ml-4) and at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3).

[0327] The reaction of the compound (Ml-4) with at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3) is preferably carried out under a deoxidized atmosphere (for example, under a nitrogen atmosphere).

[0328] The amount of use of the compound (Ml-2) is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, relative to 1 mole of the compound (Ml-4).

[0329] The amount of use of the compound (Ml-3) is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, relative to 1 mole of the compound (Ml-4).

[0330] The amount of use of the base is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, relative to 1 mole of the compound (Ml-4).

[0331] The reaction time of the reaction of the compound (Ml-4) with at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3) is usually 0.1 to 200 hours.

[0332] The reaction temperature of the reaction of the compound (Ml-4) with at least one compound selected from the group consisting of the compound (Ml-2) and the compound (Ml-3) is usually -100 to 200°C.

[0333] <Composition Containing Compound (I)>

[0334] The present application also includes a composition containing the compound (I). A molded body formed from the composition containing the compound (I) preferably has a transmittance of 50% or less, more preferably 30% or less, further preferably 15% or less, particularly preferably 10% or less, at the maximum absorption wavelength [nm] of the compound (I) contained therein.

[0335] The composition containing the compound (I) is preferably a resin composition containing the compound (I) and a resin (hereinafter, sometimes referred to as "resin composition") or a composition containing the compound (I) and a polymerizable monomer (hereinafter, sometimes referred to as "composition (1)").

[0336] The composition containing the compound (I) can be used for all uses, and can be particularly suitable for uses which can be exposed to sunlight or light containing ultraviolet rays. As specific examples, for example, glass substitutes and surface coating materials thereof; coating materials for window glasses, lighting glasses, and light source protective glasses of houses, facilities, transportation equipment, and the like; window films of houses, facilities, transportation equipment, and the like; interior and exterior decoration materials of houses, facilities, transportation equipment, and the like, and paints for interior and exterior decoration and coating films formed using the paints; alkyd resin paint and coating films formed using the paint; acrylic paint and coating films formed using the paint; members for light sources which emit ultraviolet rays such as fluorescent lamps and mercury lamps; shielding materials for electromagnetic waves generated from precision machines, electronic and electric equipment, various displays, and the like; containers or packaging materials for foods, chemicals, pharmaceuticals, and the like; bottles, boxes, blister packs, cups, special packaging, optical disc coatings, sheet or film materials for industrial and agricultural uses; anti-fading agents for printed matters, dyed matters, dyes, pigments, and the like; protective films for polymer supports (for example, plastic parts for mechanical and automobile parts); overcoatings for printed matters; inkjet medium films; interlayer ground glass; optical films; safety glass / windshield interlayer; electrochromic / photochromic uses; overprotective films; solar heat control films; sunscreens, shampoos, hair conditioners, styling agents, and the like cosmetic products; fiber products and fibers for clothing materials such as sportswear, stockings, hats, and the like; household interior products such as curtains, carpets, wallpapers, and the like; medical instruments such as plastic lenses, contact lenses, artificial eyes, and the like; optical products such as optical filters, back light display films, prisms, mirrors, photographic materials, and the like; stationery such as mold films, transfer labels, anti-graffiti films, adhesive tapes, inks, and the like; signs, markers, and the like and surface coating materials thereof, and the like.

[0337] The shape of the shaped body formed from the composition of the present application can be any shape such as a flat film shape, a powder shape, a spherical particle shape, a broken particle shape, a massive continuum shape, a fiber shape, a tube shape, a hollow filament shape, a granular shape, a plate shape, a porous shape, and the like.

[0338] As the resin used in the above-mentioned resin composition, various thermoplastic resins and thermosetting resins and the like which have been used in the manufacture of known shaped bodies, sheets, films, and the like can be mentioned.

[0339] As the thermoplastic resin, for example, an olefin-based resin such as a polyethylene resin, a polypropylene resin, a polycycloolefin resin, a poly(meth)acrylate-based resin, a polystyrene-based resin, a styrene-acrylonitrile-based resin, an acrylonitrile-butadiene-styrene-based resin, a polyvinyl chloride-based resin, a polyvinylidene chloride-based resin, a polyvinyl acetate-based resin, a polyvinyl butyral-based resin, an ethylene-vinyl acetate copolymer, an ethylene-vinyl alcohol resin, a polyethylene terephthalate resin, a polybutylene terephthalate resin, a liquid crystal polyester resin, and the like are exemplified. These resins can be used as a polymer blend or a polymer alloy of one or more kinds.

[0340] As the thermosetting resin, for example, an epoxy resin, a melamine resin, an unsaturated polyester resin, a phenol resin, a urea resin, an alkyd resin, a thermosetting polyimide resin, and the like are exemplified.

[0341] In the case where the above-described resin composition is used as an ultraviolet absorbing filter or an ultraviolet absorbing film, the resin is preferably a transparent resin.

[0342] The above-described resin composition can be obtained by mixing the compound (I) with a resin. The compound (I) can be contained in an amount necessary to impart a desired property, for example, 0.00001 to 99 parts by mass, relative to 100 parts by mass of the resin.

[0343] The resin composition can contain, as needed, a solvent, a crosslinking catalyst, an adhesion promoter, a plasticizer, a softening agent, a dye, a pigment, an inorganic filler, and the like.

[0344] As the polymerizable monomer used in the above-described composition (1), there is no particular limitation, and a radical polymerizable monomer is preferred, a photoradical polymerizable monomer is more preferred, and a (meth)acrylate is further preferred.

[0345] As the (meth)acrylate, a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule, a difunctional (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 are exemplified.

[0346] The composition (1) preferably further contains a polymerization initiator. In the case where the polymerizable monomer is a radical polymerizable monomer, the polymerization initiator is preferably a radical polymerization initiator, and more preferably a photopolymerization initiator.

[0347] The composition (1) can be obtained by mixing the compound (I) with a polymerizable monomer. The compound (I) can be contained in an amount necessary to impart desired properties, for example, 0.01 to 20 parts by mass, relative to 100 parts by mass of the polymerizable monomer.

[0348] The composition (1) can contain, as needed, a solvent, a crosslinking catalyst, an adhesion-improving agent, a plasticizer, a softening agent, a dye, a pigment, an inorganic filler, and other additives.

[0349] In the case where the composition of the present application is used for an optical article such as an optical film, it can be applied to an image display device, for example. In the case where the composition of the present application is applied to an image display device, the optical layer formed from the composition of the present application can be applied to any one of a film layer, an adhesive layer, a coating layer, and the like, and is preferably an adhesive layer or a coating layer.

[0350] In the case where the composition of the present application is used for an optical article, it can be an optical layer formed from the composition of the present application alone, or an optical laminate in which the optical layer formed from the composition of the present application is laminated with other layers. As the other layers, a polarizing film, a phase difference film, a thermoplastic resin film, and the like can be given, for example. If the optical laminate is a laminate in which the optical layer of the present application, an adhesive layer, and a polarizing film are sequentially laminated, the optical layer of the present application is preferably an optical layer (optical film) formed from the composition of the present application. If the optical laminate is a laminate in which the optical layer of the present application, a thermoplastic resin film, an adhesive layer, and a polarizing film are sequentially laminated, the optical layer of the present application is preferably an optical layer (coating layer) formed from the composition of the present application. If the optical laminate is a laminate in which a phase difference film, the optical layer of the present application, and a phase difference film are sequentially laminated, the optical layer of the present application is preferably an optical layer (adhesive layer) formed from the composition of the present application.

[0351] <Adhesive Composition>

[0352] In the case where the layer formed from the composition of the present application is an adhesive layer, it is formed from an adhesive composition containing the resin (A), the compound (I), the crosslinking agent (B), and the silane compound (C) (hereinafter, sometimes referred to as an adhesive composition (i)). The adhesive composition (i) can further contain a radical-curable component (D), an initiator (E), a light-absorbing compound (F) other than the compound (I) (hereinafter, sometimes referred to as a light-selective absorbing compound (F)), an antistatic agent, and the like, 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).

[0353] The resin (A) is not particularly limited as long as it is a resin used in an adhesive composition. The resin (A) preferably does not show a great absorption in the range of a wavelength of 300 nm to a wavelength of 780 nm.

[0354] The resin (A) is preferably a resin having 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, further preferably 10°C or lower, and particularly preferably 0°C or lower. In addition, 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, further preferably -55°C or higher, and particularly preferably -50°C or higher. If the glass transition temperature of the resin (A) is 40°C or lower, the adhesion of the adhesive layer formed from the adhesive composition (i) to the adherend is improved. In addition, if the glass transition temperature of the resin (A) is -80°C or higher, the durability of the adhesive layer formed from the adhesive composition (i) is improved. Note that the glass transition temperature can be measured using a differential scanning calorimeter (DSC).

[0355] As the resin (A), a (meth)acrylic resin, a silicone resin, a rubber-based resin, a urethane-based resin, and the like can be given, and a (meth)acrylic resin is preferred.

[0356] As the (meth)acrylic resin, a polymer in which a structural unit derived from a (meth)acrylic ester is a main component (preferably contains 50% by mass or more) is preferred. The structural unit derived from a (meth)acrylic ester can contain one or more structural units derived from a monomer other than a (meth)acrylic ester (for example, a structural unit derived from a monomer having a polar functional group such as a hydroxyl group, a carboxyl group, an amino group, and the like).

[0357] The content of the resin (A) is usually 50% by mass or more to 99.9% by mass or less, preferably 60% by mass or more to 95% by mass or less, and more preferably 70% by mass or more to 90% by mass or less, in 100% by mass of the solid content of the adhesive composition (i).

[0358] The content of the compound (I) is usually 0.01 parts by mass or more to 20 parts by mass or less, preferably 0.1 parts by mass or more to 20 parts by mass or less, and more preferably 0.2 parts by mass or more to 10 parts by mass or less, and particularly preferably 0.5 parts by mass or more to 5 parts by mass or less, relative to 100 parts by mass of the resin (A).

[0359] As the crosslinking agent (B), an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent, an aziridine-based crosslinking agent, a metal chelate-based crosslinking agent, and the like can be given, and an isocyanate-based crosslinking agent is particularly preferred from the viewpoints of the pot life of the adhesive composition, the durability and the crosslinking speed of the adhesive layer, and the like.

[0360] 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, further 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).

[0361] As the silane compound (C), for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3- glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3- glycidoxypropylethyldimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3- chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3- methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, and the like can be given.

[0362] The silane compound (C) can be a silicone oligomer.

[0363] 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, further 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).

[0364] As the radical-curable component (D), a compound or an oligomer which is cured by a radical polymerization reaction, and the like can be given.

[0365] As the radical-polymerizable component (D), a (meth)acrylate compound, a styrene compound, a vinyl compound, and the like can be given.

[0366] The adhesive composition (i) can contain two or more kinds of the radical-curable component (D).

[0367] As the (meth)acrylate compound, a (meth)acrylate monomer, a (meth)acrylamide monomer, and a (meth)acrylic oligomer having at least two (meth)acryloyl groups in the molecule, and the like containing a (meth)acryloyl group can be given. The (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. The (meth)acrylate compound can be used alone only one kind, or two or more kinds in combination.

[0368] As the (meth)acrylate monomer, 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 can be given.

[0369] The (meth)acrylate compound is preferred, and a polyfunctional (meth)acrylate compound is more preferred. The polyfunctional (meth)acrylate compound is preferably trifunctional or higher.

[0370] 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, further 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).

[0371] The initiator (E) can be either a compound that causes a polymerization reaction by absorbing the energy of heat (a thermal polymerization initiator) or a compound that causes a polymerization reaction by absorbing the energy of light (a photopolymerization initiator). Note that, here, light is preferably active energy rays such as visible light, ultraviolet light, X-rays, or electron beams.

[0372] As the thermal polymerization initiator, a compound that generates radicals by heating or the like (a thermal radical generator), a compound that generates acid by heating or the like (a thermal acid generator), a compound that generates base by heating or the like (a thermal base generator), and the like can be given.

[0373] As the photopolymerization initiator, a compound that generates radicals by absorbing the energy of light (a photoradical generator), a compound that generates acid by absorbing the energy of light (a photoacid generator), a compound that generates base by absorbing the energy of light (a photobase generator), and the like can be given.

[0374] The initiator (E) is preferably selected so as to be suitable for the polymerization reaction of the radical-curable component (D) described above, and is preferably a radical polymerization initiator, and more preferably a photoradical polymerization initiator.

[0375] The radical polymerization initiator can be given, for example, an alkylphenone compound, a benzoin compound, a benzophenone compound, an oxime ester compound, a phosphine compound, and the like. The radical polymerization initiator is preferably a photoradical polymerization initiator, and more preferably an oxime ester-based photoradical polymerization initiator from the viewpoint of the reactivity of the polymerization reaction. By using an oxime ester-based photoradical polymerization initiator, the reaction rate of the radical-curable component (D) can be improved even under curing conditions in which the illuminance or the amount of light is weak.

[0376] 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, further 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).

[0377] The light-selective absorption compound (F) is a light-absorbing compound other than the compound (I), for example, a compound (ultraviolet absorber) that absorbs light having a wavelength of 250 nm to 380 nm (preferably, 250 nm or more and less than 360 nm), a compound (colorant) that absorbs 380 to 780 nm, or a compound (infrared absorber) that absorbs 780 to 1500 nm.

[0378] The ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light having a wavelength of 250 nm to 380 nm, and is preferably a benzotriazole-based compound, a benzophenone-based compound, a triazine-based compound, a salicylic acid-based compound, a cyanoacrylate-based compound, a benzoxazine-based compound, or the like.

[0379] 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, further 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).

[0380] The optical layer and the optical layer stack including the optical layer of the present application can be stacked on a display element such as an organic EL element or a liquid crystal cell, and used for an image display device (FPD: flat panel display) such as an organic EL display device or a liquid crystal display device.

[0381] Examples

[0382] Hereinafter, the present application will be described more specifically by showing examples and comparative examples, but the present application is not limited to these examples. In the examples, % and parts indicating the content or the amount of use are based on mass unless otherwise specified.

[0383] (Synthesis of the compound represented by formula (1))

[0384]

[0385] A 300 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, and 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one 7 parts, ethanol 70 parts, potassium hydroxide 2.4 parts, and malononitrile 6.2 parts were charged, and stirred at 80°C under reflux for 3 hours. To the resulting mixture, ethanol 62 parts, malononitrile 6.2 parts, and potassium hydroxide 4.8 parts were added, and stirred at 80°C under reflux for 3 hours. After distilling off the solvent from the resulting mixture, purification was performed, and 6.9 parts of a compound represented by formula (al) was obtained.

[0386]

[0387] A 20 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, and 1.5 parts of a compound represented by formula (al), 1.0 part of p-toluenesulfonyl cyanide, 0.3 part of potassium hydroxide, and 10 parts of ethanol were charged, and stirred at 80°C under reflux for 3 hours. After distilling off the solvent from the resulting mixture, purification was performed, and 0.7 parts of a compound represented by formula (1) was obtained.

[0388] LC-MS measurement and 1 H-NMR analysis confirmed that a compound represented by formula (1) was produced. In addition, the presence of potassium cation was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis).

[0389] 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)

[0390] LC-MS: [M] - = 284.2

[0391] <Maximum absorption wavelength and extinction coefficient ε measurement>

[0392] A 2-butanone solution (0.003 g / L) of the resulting compound represented by formula (1) was put into a 1 cm quartz cell, and the quartz cell was set to a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance in the wavelength range of 300 to 800 nm was measured by a double-beam method at a step length of 1 nm. 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, the extinction coefficient at each wavelength was calculated.

[0393] ε(λ) = A(λ) / CL

[0394] (In the formula, 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 a quartz cell.)

[0395] The maximum absorption wavelength of the obtained compound represented by formula (1) was 518 nm. The ε(λmax) of the obtained compound represented by formula (1) was 444 L / (g-cm).

[0396] Measurement of Full Width at Half Maximum of Compound

[0397] A 2-butanone solution (concentration: 0.003 g / L) of the obtained compound represented by formula (1) was placed in a 1-cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). The absorbance in the wavelength range of 300 to 800 nm was measured by a double-beam method at a step length of 1 nm. The wavelengths of two points at which the absorbance was half the maximum absorbance wavelength were confirmed. The wavelength on the long-wavelength side was subtracted from the wavelength on the short-wavelength side among the wavelengths of the two points, and the result was taken as the full width at half maximum. The full width at half maximum of the compound represented by formula (1) was 26 nm.

[0398] Synthesis of Compound Represented by Formula (M-2) (Example 2)

[0399]

[0400] A 500-mL four-necked flask equipped with a Dimroth condenser and a thermometer was set under a nitrogen atmosphere, and 25 parts of a 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 p-toluenesulfonyl cyanide were added. The mixture was stirred in an ice bath for 4 hours. After the solvent was distilled off from the obtained mixture, purification was performed, and 17.4 parts of a compound represented by formula (M-2) was obtained.

[0401] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (M-2) was produced.

[0402] 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)

[0403] LC-MS; [M] = 188.1

[0404] Synthesis of Compound Represented by Formula (M-3) (Example 3)

[0405]

[0406] A 300 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to nitrogen atmosphere, and 5 parts of a 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 for 10 minutes in an ice bath. To the resulting mixture, 2.1 parts of malononitrile and 4.4 parts of diisopropylethylamine were added, and further stirred for 30 minutes. After distilling off the solvent from the resulting mixture, purification was performed, and 5.4 parts of a compound represented by formula (M-3) was obtained.

[0407] LC-MS measurement and 1 H-NMR analysis confirmed that a compound represented by formula (M-3) was produced.

[0408] 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)

[0409] LC-MS; [M] = 236.3

[0410] (Synthesis of a compound represented by formula (1))

[0411]

[0412] A 100 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to nitrogen atmosphere, and 2 parts of a 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 for 2 hours in an ice bath. To the resulting mixture, 0.7 parts of malononitrile and 1.4 parts of diisopropylethylamine were added, and further stirred for 30 minutes. After distilling off the solvent from the resulting mixture, purification was performed, and 1.4 parts of a compound represented by formula (1) was obtained.

[0413] LC-MS measurement and 1 H-NMR analysis confirmed that a compound represented by formula (1) was produced. In addition, the presence of potassium cation was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis).

[0414] 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)

[0415] LC-MS; [M] -= 284.2

[0416] (Synthesis of the compound represented by formula (2))

[0417]

[0418] A 50 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, and 0.5 parts of the compound represented by formula (al), 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. After distilling off the solvent from the resulting mixture, purification was performed, and 0.4 parts of the compound represented by formula (2) was obtained.

[0419] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (2) was produced. In addition, the presence of potassium cation was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Furthermore, in the same manner as described above, the maximum absorption wavelength, the gram absorption coefficient, and the full width at half maximum were measured, and as a result, 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.

[0420] 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)

[0421] LC-MS; [M] - = 359.4

[0422] (Synthesis of the compound represented by formula (3))

[0423]

[0424] A 20 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, and 0.5 parts of the compound represented by formula (al), 5 parts of dehydrated acetonitrile, and 0.3 parts of N-chlorosuccinimide were added, and stirred in an ice bath for 3 hours. After distilling off the solvent from the resulting mixture, purification was performed, and 0.4 parts of the compound represented by formula (3) was obtained.

[0425] LC-MS measurement was performed to confirm that the compound represented by formula (3) was produced. In addition, the presence of potassium cation was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Furthermore, in the same manner as described above, the maximum absorption wavelength, the molar extinction coefficient, and the full width at half maximum were measured, and as a result, the maximum absorption wavelength of the compound represented by formula (3) was 551 nm, the molar extinction coefficient ε (λmax) at the maximum absorption wavelength was 130 L / (g-cm), and the full width at half maximum was 28 nm.

[0426] LC-MS; [M] - = 293.5

[0427] (Synthesis of the compound represented by formula (4))

[0428]

[0429] A 20 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, and 0.5 parts of the compound represented by formula (al), 5 parts of dehydrated dimethylformamide, and 0.5 parts of N-chlorosuccinimide were added, and stirred in an ice bath for 3 hours. After distilling off the solvent from the obtained mixture, purification was performed to obtain 0.4 parts of the compound represented by formula (4).

[0430] LC-MS measurement and 1 H-NMR analysis was performed to confirm that the compound represented by formula (4) was produced. In addition, the presence of potassium cation was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Furthermore, in the same manner as described above, the maximum absorption wavelength, the molar extinction coefficient, and the full width at half maximum were measured, and as a result, the maximum absorption wavelength of the compound represented by formula (4) was 572 nm, the molar extinction coefficient ε (λmax) at the maximum absorption wavelength was 126 L / (g-cm), and the full width at half maximum was 44 nm.

[0431] LC-MS; [M] - = 328.2

[0432] 1 H-NMR (deuterated dimethyl sulfoxide) δ: 1.24-1.25 (m, 2H), 1.88-2.33 (m, 7H)

[0433] (Synthesis of the compound represented by formula (5))

[0434]

[0435] A 20 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set under nitrogen atmosphere, and 1 part of a compound represented by formula (a1), 10 parts of dehydrated dimethylformamide, and 0.7 part of N-bromosuccinimide were added, and stirred in an ice bath for 3 hours. After distilling off the solvent from the resulting mixture, purification was performed to obtain 0.7 part of a compound represented by formula (5).

[0436] LC-MS measurement and 1 H-NMR analysis confirmed that a compound represented by formula (5) was produced. In addition, the presence of potassium cation was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Furthermore, in the same manner as described above, the maximum absorption wavelength, the gram absorption coefficient, and the full width at half maximum were measured, and as a result, 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.

[0437] LC-MS; [M] - = 338.2

[0438] 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)

[0439] (Synthesis of a compound represented by formula (M-4) (Example 9))

[0440]

[0441] A 100 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set under nitrogen atmosphere, and 5 parts of a compound represented by formula (M-2), 50 parts of dehydrated acetonitrile, and 0.7 part of sodium hydride were added, and stirred in an ice bath for 30 minutes. To the resulting mixture, 9.6 parts of p-toluenesulfonyl cyanide was added, and stirred at 50°C for 4 hours. After distilling off the solvent from the resulting mixture, purification was performed to obtain 3.8 parts of a compound represented by formula (M-4).

[0442] LC-MS measurement and 1 H-NMR analysis confirmed that a compound represented by formula (M-4) was produced.

[0443] LC-MS; [M] - = 213.1

[0444] 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)

[0445] (Example 10) Synthesis of the compound represented by formula (6)

[0446]

[0447] A 200 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to 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. To the resulting mixture, 7.1 parts of triflic anhydride was added, and stirred in an ice bath for 30 minutes, and further 1.7 parts of malononitrile and 3.5 parts of potassium carbonate were added, and stirred at 50°C for 2 hours. After distilling off the solvent from the resulting mixture, purification was performed, and 2.1 parts of the compound represented by formula (M-5) was obtained.

[0448]

[0449] A 300 mL-four necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, 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 p-toluenesulfonic anhydride, and 1.5 parts of malononitrile were mixed, and stirred in an ice bath for 24 hours. After distilling off the solvent from the resulting mixture, purification was performed, and 0.4 parts of the compound represented by formula (6) was obtained. Note that the potassium ion in the compound represented by formula (6) was derived from potassium bicarbonate used in the purification.

[0450] LC-MS measurement and 1 H-NMR analysis confirmed that the anion in the compound represented by formula (6) was generated. In addition, the presence of potassium atoms (potassium cations) was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis).

[0451] Further, the maximum absorption wavelength, the gram absorption coefficient, and the full width at half maximum were measured in the same manner as described above, and as a result, 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.

[0452] LC-MS; [M] - = 309.3

[0453] 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)

[0454] Preparation of an acrylic resin

[0455] Preparation of acrylic resin (Al)

[0456] A mixed solution of 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 3 parts of 2-hydroxyethyl methyl acrylate and 1 part of acrylic acid as a solvent was charged in a reaction vessel equipped with a condenser, a nitrogen inlet tube, a thermometer and a stirrer, while replacing the air in the apparatus with nitrogen to make it free from oxygen and raising the internal temperature to 55°C. Then, a solution of 0.14 parts of azobisisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added in the entire amount. After the addition of the polymerization initiator, the temperature was maintained for 1 hour, and then, while maintaining the internal temperature at 54 to 56°C, ethyl acetate was continuously added to the reaction vessel at an addition rate of 17.3 parts / hr. The addition of ethyl acetate was stopped at the point when the concentration of the acrylic resin became 35%, and further, the temperature was maintained for 12 hours from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, and an ethyl acetate solution of the acrylic resin was prepared. The weight average molecular weight Mw of the acrylic resin obtained based on polystyrene by GPC was 1.4 million, and Mw / Mn was 5.5. This was used as the acrylic resin (Al).

[0457] Preparation of acrylic resin (Al)

[0458] A mixed solution of 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 3 parts of 2-hydroxyethyl methyl acrylate and 1 part of acrylic acid as a solvent was charged in a reaction vessel equipped with a condenser, a nitrogen inlet tube, a thermometer and a stirrer, while replacing the air in the apparatus with nitrogen to make it free from oxygen and raising the internal temperature to 55°C. Then, a solution of 0.14 parts of azobisisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added in the entire amount. After the addition of the polymerization initiator, the temperature was maintained for 1 hour, and then, while maintaining the internal temperature at 54 to 56°C, ethyl acetate was continuously added to the reaction vessel at an addition rate of 17.3 parts / hr. The addition of ethyl acetate was stopped at the point when the concentration of the acrylic resin became 35%, and further, the temperature was maintained for 12 hours from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, and an ethyl acetate solution of the acrylic resin was prepared. The weight average molecular weight Mw of the acrylic resin obtained based on polystyrene by GPC was 1.4 million, and Mw / Mn was 5.5. This was used as the acrylic resin (Al).

[0459] (Example 11) Production of Resin Composition (1) (Adhesive Composition (1))

[0460] Preparation of Resin Composition (1)

[0461] With respect to 100 parts of an ethyl acetate solution of the acrylic resin (A1) (resin concentration: 20%), 0.5 parts of a crosslinking agent (manufactured by DKS Co., Ltd., trade name "Coronate L", isocyanate-based compound, solid 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) were mixed, and 2-butanone was further added so that the solid content concentration became 14%, to obtain a resin composition (1) (adhesive composition (1)). Note that the amount of the crosslinking agent added was in terms of the mass of the active ingredient.

[0462] (Examples 12 to 18, Comparative Example 1) Preparation of Resin Compositions (2) to (9)

[0463] The 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. Note that the amount of the crosslinking agent added was in terms of the mass of the active ingredient, and the amount of the resin (A) added was in terms of the mass of the solid content.

[0464] [Table 7]

[0465]

[0466] Note that each of the abbreviations in Table 7 represents the following meaning.

[0467] Acrylic resin (A1): the acrylic resin (A1) synthesized in Polymerization Example 1

[0468] Acrylic resin (A2): the acrylic resin (A2) synthesized in Polymerization Example 2

[0469] Formula (1): the compound represented by formula (1) synthesized in Example 1 or Example 4 Formula (6): the compound represented by formula (6) synthesized in Example 10

[0470] Coronate L: manufactured by DKS Co., Ltd., trade name: Coronate L, isocyanate-based crosslinking agent

[0471] KBM3066: manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, silane coupling agent

[0472] A-DPH-12E: manufactured by Shin Nakamura Chemical Co., Ltd., trade name: A-DPH-12E, 6-functional (meth)acrylate compound

[0473] NCI-730: manufactured by ADEKA Corporation, trade name: NCI-730, oxime ester compound as a photoradical generator

[0474] RUV-93: manufactured by Takachiho Chemical Industries, Ltd., benzotriazole-based ultraviolet absorber, trade name: RUV A-93, maximum absorption wavelength λmax= 337 nm

[0475] Formula (B): The compound (3-butyl-2-[3-(-3-butyl-5-phenyl-2(3H)-benzoxazolium)-1-propen-1-yl]-5-phenyl-benzoxazolium p-toluenesulfonate) shown in the following Formula (B) synthesized with reference to the specification of U.S. Patent No. 6004536, and the full width at half maximum was 44 nm, as calculated in the same manner as above.

[0476]

[0477] Evaluation of the molded body of the resin composition (1)

[0478] Preparation of the resin molded body (1)

[0479] The obtained resin composition (1) (adhesive composition (1)) was applied to the release-treated surface of a separator comprising a polyethylene terephthalate film (trade name "PLR-382190" obtained from Toray Industries, Inc.) on which a release treatment was performed, using an applicator, and dried at 100°C for 1 minute to form a resin molded body (adhesive layer) (1), and a resin molded body (1) with a separator was prepared. The thickness of the obtained resin molded body (1) was 15 μm.

[0480] The obtained resin molded body (1) with a separator was attached to a 23-μm cycloolefin film containing an ultraviolet absorber (trade name "ZEONOR" obtained from ZEON Corporation, Japan) using a laminator, and a laminate (1-1) having a layered structure of cycloolefin film / resin molded body (1) / separator was obtained by curing under conditions of a temperature of 23°C and a relative humidity of 65% for 7 days.

[0481] Absorbance measurement of the resin molded body (1)

[0482] The obtained laminate (1-1) was cut into a size of 30 mm x 30 mm, the separator was peeled off, and the resin molded body (1) was bonded to an alkali-free glass (trade name "EAGLE XG" manufactured by Corning Inc.) to serve as a sample (1). Using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation), the absorbance of the sample (1) produced was measured at a wavelength of 300 to 800 nm at a step of 1 nm. The absorbance at a wavelength of 330 nm measured was taken as the absorbance of the resin molded body (1) at a wavelength of 330 nm. Note that the absorbance at a wavelength of 330 nm of each of the alkali-free glass alone and the cyclic olefin film alone was 0.

[0483] In addition, the transmittance at a wavelength of 330 nm was calculated based on the following equation. The result is shown in the transmittance column of Table 8.

[0484] T = 10 -A x 100 (T represents transmittance, and A represents absorbance.)

[0485] The maximum absorption wavelength of the sample (1) was determined from the absorbance measured above, and the absorbance at the determined maximum absorption wavelength was taken as the absorbance of the resin molded body (1) at the above-mentioned maximum absorption wavelength. Note that the absorbance at the above-mentioned maximum absorption wavelength of each of the alkali-free glass alone and the cyclic olefin film alone was 0.

[0486] The transmittance (%) at the above-mentioned maximum absorption wavelength was calculated based on the following equation. The result is shown in Table 9.

[0487] T1 = 10 -A1 x 100

[0488] (T1 represents the transmittance at the above-mentioned maximum absorption wavelength, and A1 represents the absorbance at the above-mentioned maximum absorption wavelength.)

[0489] [Resistance to exudation of resin molded body (1)]

[0490] A separator was further laminated to one face of the obtained resin molded body (1) with a separator to obtain an adhesive layer (1) with a separator on both faces. The obtained adhesive layer (1) with a separator on both faces was stored in air at 23 to 25°C for 1 month. For the adhesive layer (1) with a separator on both faces after storage, a microscope was used to confirm whether or not crystallization of a compound had occurred in the plane. If no crystallization had occurred, a was noted, and if crystallization had occurred, b was noted. The evaluation result is shown in the resistance to exudation column of Table 8.

[0491] [Measurement of absorbance retention rate of resin molded body (1)]

[0492] A polarizing plate in which a 13-μm-thick cyclic olefin film was bonded to one face of a polarizing plate using an adhesive layer was prepared.

[0493] After the resin-molded body (1) side of the resin-molded body (1) with a separator was attached to the polarizing plate side of the polarizing plate using a laminator, the laminate having a stacked structure of a cyclic olefin film / polarizing plate / resin-molded body (1) / separator was obtained by curing for 7 days under conditions of a temperature of 23°C and a relative humidity of 65%.

[0494] The obtained laminate was cut to a size of 30 cm x 30 cm, the separator was peeled off, and the resin-molded body (1) was attached to an alkali-free glass (trade name "EAGLE XG" manufactured by Corning Inc.) to obtain a laminate (1-2) having a stacked structure of a cyclic olefin film / polarizing plate / resin-molded body (1) / glass.

[0495] The obtained laminate (1-2) was subjected to a weather resistance test by being left in a sunlight weather resistance tester (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. The absorbance of the removed laminate (1-2) was measured by the same method as described above. Based on the measured absorbance, the absorbance retention rate [%] 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 rate is to 100%, the less the light selective absorption function is deteriorated, and the better the weather resistance is.

[0496] Note that, regarding the absorption wavelength used for evaluating the absorbance retention rate, among the measured absorbances, a wavelength at which the absorbance on the long wavelength side of the wavelength of maximum absorption becomes 1 to 1.5 was selected. This is because the above wavelength is the most sensitive absorbance region in terms of the measurement accuracy of the spectrometer.

[0497] Absorbance retention rate (%)

[0498] = (A(540) after durability test / A(540) before durability test) x 100

[0499] [A(540) indicates the absorbance of the laminate (1-2) at a wavelength of 540 nm.]

[0500] Using the resin composition (2) instead of the resin composition (1), a resin-molded body (2), a laminate (2-1), and a laminate (2-2) were produced, and evaluation was similarly performed. The results are shown in Table 8.

[0501] Using the resin composition (3) instead of the resin composition (1), a resin-molded body (3), a laminate (3-1), and a laminate (3-2) were produced, and evaluation was similarly performed. The results are shown in Table 8.

[0502] A resin-molded body (5) having a thickness of 20 μm was produced using the resin composition (5) instead of the resin composition (1). Using the resin-molded body (5) instead of the resin-molded body (1), the same operation was performed except for this, to produce a laminate (5-1) and a laminate (5-2), and the bleeding resistance evaluation, the absorbance retention rate evaluation were performed. Note that the absorbance retention rate evaluation was performed at a wavelength of 520 nm. The results are shown in Table 8.

[0503] A resin-molded body (6) having a thickness of 20 μm was produced using the resin composition (6) instead of the resin composition (1). Using the resin-molded body (6) instead of the resin-molded body (1), the same operation was performed except for this, to produce a laminate (6-1) and a laminate (6-2), and the bleeding resistance evaluation, the absorbance retention rate evaluation were performed. Note that the absorbance retention rate evaluation was performed at a wavelength of 530 nm. The results are shown in Table 8.

[0504] A resin-molded body (7) having a thickness of 20 μm was produced using the resin composition (7) instead of the resin composition (1). Using the resin-molded body (7) instead of the resin-molded body (1), the same operation was performed except for this, to produce a laminate (7-1) and a laminate (7-2), and the bleeding resistance evaluation, the absorbance retention rate evaluation were performed. Note that the absorbance retention rate evaluation was performed at a wavelength of 520 nm. The results are shown in Table 8.

[0505] A resin-molded body (8) having a thickness of 20 μm was produced using the resin composition (8) instead of the resin composition (1). Using the resin-molded body (8) instead of the resin-molded body (1), the same operation was performed except for this, to produce a laminate (8-1) and a laminate (8-2), and the bleeding resistance evaluation, the absorbance retention rate evaluation were performed. Note that the absorbance retention rate evaluation was performed at a wavelength of 520 nm. The results are shown in Table 8.

[0506] A resin-molded body (9) having a thickness of 20 μm was produced using the resin composition (9) instead of the resin composition (1). Using the resin-molded body (9) instead of the resin-molded body (1), the same operation was performed except for this, to produce a laminate (9-1) and a laminate (9-2), and the bleeding resistance evaluation, the absorbance retention rate evaluation were performed. Note that the absorbance retention rate evaluation was performed at a wavelength of 510 nm. The results are shown in Table 8.

[0507] Evaluation of the resin-molded body (4)

[0508] Production of the resin-molded body (4)

[0509] The resin composition (4) was applied to the release-treated surface of a separator comprising a polyethylene terephthalate film (trade name "PLR-382190" available from Toray Industries, Inc.) that had been subjected to release treatment using an applicator so as to have a dry thickness of 5 μm, and dried at 100°C for 1 minute. Then, using an ultraviolet irradiation device (Fusion UV Systems, "Electrodeless UV Lamp System H Bulb"), the ultraviolet rays were irradiated in such a manner that the intensity of UV-A (wavelength 320 to 390 nm) was 500 mW and the cumulative light amount was 500 mJ, whereby a resin molded body (adhesive layer) (4) was formed, and a separator-equipped resin molded body (4) was produced.

[0510] The obtained separator-equipped resin molded body (4) was attached to an alkali-free glass, and after the separator was peeled off, a 23-μm cycloolefin film containing an ultraviolet absorber (trade name "ZEONOR" available from ZEON Corporation) was attached to the resin molded body (4), and a laminate (4-1) having a layered structure of cycloolefin film / resin molded body (4) / glass was produced.

[0511] The produced laminate (4-1) was set in a spectrophotometer UV-2450 (Shimadzu Corporation), and the absorbance was measured by a double-beam method at a wavelength range of 300 to 800 nm at a step of 1 nm. The absorbance at a wavelength of 330 nm as measured was taken as the absorbance of the resin molded body (4) at a wavelength of 330 nm. Note that the absorbance at a wavelength of 330 nm of the alkali-free glass alone and the cycloolefin film alone was 0.

[0512] In addition, the transmittance (%) at a wavelength of 330 nm was calculated based on the following formula. The results are shown in Table 8.

[0513] T = 10 -A x 100 (T represents transmittance, and A represents absorbance.)

[0514] Based on the absorbance measured above, the wavelength of the maximum absorption of the laminate (4-1) was determined, and the absorbance at the determined wavelength of the maximum absorption was taken as the absorbance of the resin molded body (4) at the wavelength of the maximum absorption. Note that the absorbance at the wavelength of the maximum absorption of the alkali-free glass alone and the cycloolefin film alone was 0.

[0515] The transmittance (%) at the wavelength of the maximum absorption was calculated based on the following formula. The results are shown in Table 9.

[0516] T1 = 10 -A1 x 100

[0517] (T1 represents the transmittance at the wavelength of the maximum absorption, and A1 represents the absorbance at the wavelength of the maximum absorption.)

[0518] 〔Evaluation of the permeation resistance of the resin molded body (4)〕

[0519] A diaphragm was further laminated on one face of the obtained resin molded body (4) with a diaphragm to obtain an adhesive layer (4) with diaphragms on both faces. The obtained adhesive layer (4) with diaphragms on both faces was stored in air at 23 to 25°C for 1 month. For the adhesive layer (4) with diaphragms on both faces after storage, a microscope was used to confirm the presence or absence of crystallization of the compound in the plane. If there was no crystallization, it was recorded as a, and if there was crystallization, it was recorded as b. The evaluation results are shown in the column for permeation resistance in Table 8.

[0520] 〔Measurement of the absorbance retention rate of the resin molded body (4)〕

[0521] A polarizing plate in which a 13-μm cycloolefin film was attached to one face of a polarizing plate with an adhesive layer was prepared.

[0522] The resin molded body (4) side of the resin molded body (4) with a diaphragm was attached to the polarizing plate side of the polarizing plate using a laminator, and the obtained laminate was stored under conditions of a temperature of 23°C and a relative humidity of 65% for 7 days to obtain a laminate having a laminated structure of cycloolefin film / polarizing plate / resin molded body (4) / diaphragm.

[0523] The diaphragm was peeled from the obtained laminate, and the resin molded body (4) was attached to an alkali-free glass (trade name "EAGLE XG" manufactured by Corning Inc.) to obtain a laminate (4-2) having a laminated structure of cycloolefin film / polarizing plate / resin molded body (4) / glass.

[0524] The obtained laminate (4-2) was subjected to a weather resistance test in a sunlight weather resistance tester (manufactured by Suga Test Instruments Co., Ltd.) under conditions of a temperature of 63°C and a relative humidity of 50% RH for 75 hours. The absorbance of the removed laminate (4-2) was measured using the same method as described above. Based on the measured absorbance, the absorbance retention rate 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 rate is to 100%, the less the light selective absorption function is deteriorated, and the better the weather resistance.

[0525] Absorbance retention rate (%)

[0526] = (A(540) after durability test / A(540) before durability test) x 100

[0527] [A(540) indicates the absorbance of the laminate (4-2) at a wavelength of 540 nm.]

[0528] [Table 8]

[0529]

[0530] [Table 9]

[0531]

[0532] The values of the transmittance at the wavelengths of the maximum absorption of Examples 11 to 13 exceeded the measurement limit (absorbance: 5) based on the spectrophotometer.

[0533] The compound of the present application has high absorption selectivity for light around the wavelength of the maximum absorption. In addition, the resin composition containing the compound of the present application also has high absorbance retention rate after the weather resistance test, and has good weather resistance.

Claims

1. A compound having an anion represented by the following formula (I-A), in formula (I-A), R 1 and R 2 each independently represents a hydrogen atom or an electron- withdrawing group selected from R 1 and R 2 at least 1 of which is an electron- withdrawing group, R 3 , R 4 , R 5 and R 6 each independently represent an electron-attracting group, said electron withdrawing group is cyano, nitro, haloalkyl, haloaryl, -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9, -OCF3, -SCF3, -SF5, -SF3, -SO2H or -SO3H, wherein, R1, R2, R3, R 3z R4, R5, R6, R7, R8and R9each independently represent a hydrocarbon group or a halogen atom.

2. The compound according to claim 1, which shows an absorption maximum at a wavelength of 400 nm to 700 nm.

3. The compound of claim 1, wherein, The extinction coefficient at the absorption maximum wavelength is 50 L / (g cm) or more.

4. A resin composition comprising the compound according to claim 1 and a resin.

5. A composition comprising the compound according to claim 1 and a polymerizable monomer.

6. A shaped body shaped from the resin composition according to claim 4 or the composition according to claim 5.

7. An optical layer comprising the resin composition according to claim 4 or the composition according to claim 5.

8. An optical layer stack comprising the optical layer according to claim 7.

9. An image display device comprising the optical layer stack according to claim 8.

10. A production method of a compound having an anion represented by the following formula (I): In formula (I), the ring W 1 forms a fused ring represented by formula (W 2 1 -1).​ R 1 and R 2 each independently represents a hydrogen atom or an electron- withdrawing group selected from R 1 and R 2 at least 1 of which is an electron- withdrawing group, R 3 , R 4 , R 5 and R 6 each independently represent an electron-attracting group, said electron withdrawing group is cyano, nitro, haloalkyl, haloaryl, -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9, -OCF3, -SCF3, -SF5, -SF3, -SO2H or -SO3H, wherein, R1, R2, R3, R 3z R4, R5, R6, R7, R8and R9each independently represent a hydrocarbon group or a halogen atom, The production method of the compound includes a step of reacting a compound represented by the following formula (M-A) with a compound represented by the following formula (b-3), In formula (M-A), ring W 1 , ring W 2 , R 1 , R 2 , R 3 , and R 4 each independently represent the same meaning as described above. In formula (b-3), R 5 and R 6 each independently represent the same meaning as described above, X2 represents -CH2-.

11. The production method according to claim 10, further comprising a step of reacting a compound represented by the following formula (M) with a compound represented by the following formula (b-2) in the presence of a catalyst to obtain a compound represented by the following formula (M-A), In formula (M), ring W 1 , ring W 2 , R 1 and R 2 each independently represent the same meaning as described above, In formula (b-2), R 3 and R 4 each independently represent the same meaning as described above, X1 represents -CH2-.

12. A production method of a compound having an anion represented by the following formula (I): In formula (I), ring W 1 , ring W 2 , R 3 , R 4 , R 5 and R 6 respectively represent the same meaning as described below, R 1 and R 2 each independently represents a hydrogen atom or an electron- withdrawing group selected from R 1 and R 2 at least 1 of which is an electron- withdrawing group, The production method of the compound includes a step of reacting at least one compound selected from a compound represented by the following formula (M1-2) and a compound represented by the following formula (M1-3) with a compound having an anion represented by the following formula (M1-1), In formula (M1-2), R 2’ cyano, nitro, haloalkyl, haloaryl, -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9, -OCF3, -SCF3, -SF5, -SF3, -SO2H, or -SO3H, wherein, R1, R2, R3, R 3z R4, R5, R6, R7, R8and R9each independently represent a hydrocarbon group or a halogen atom, E1represents a leaving group, In formula (M1-3), R 1’ is a cyano group, a nitro group, a haloalkyl group, a haloaryl group, -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9, -OCF3, -SCF3, -SF5, -SF3, -SO2H, or -SO3H, wherein R1, R2, R 3z , R4, R5, R6, R7, R8, and R9 each independently represent a hydrocarbon group or a halogen atom, and E2 represents a leaving group. In formula (M1-1), the ring W 1 forms a fused ring represented by formula (W 2 -1). 1 -1). R 3 , R 4 , R 5 and R 6 each independently represent an electron withdrawing group, said electron-withdrawing group is cyano, nitro, haloalkyl, haloaryl, -CO-R1, -CO-O-R2, -CO-NR3R 3z , -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9, -OCF3, -SCF3, -SF5, -SF3, -SO2H or -SO3H, wherein R1, R2, R 3z , R4, R5, R6, R7, R8 and R9 each independently represent a hydrocarbon group or a halogen atom.

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