CN115443265A - Compound (I) - Google Patents

Abstract

The present invention provides a novel compound that sufficiently absorbs light near a wavelength of 440 nm and has high weather resistance. A compound comprising an anion having a partial structure represented by formula (X). [In formula (X), ring W ¹ represents a ring structure having at least one substituent. Ring ^W1 is preferably a ring having 5 to 7 carbon atoms. ].

Description

compound

technical field

The present invention relates to compounds.

Background technique

In recent years, due to the popularity of mobile devices such as smartphones, the time spent watching displays at close range has continued to increase. With the increase of the time spent visually viewing the display at a close distance, the health effects of light in the wavelength range of 400nm to 500nm (so-called blue light) are also attracting strong attention.

As one of the methods for reducing the health effects of blue light, there is a method of imparting a blue light cutoff function to the surface of a display, glasses, contact lenses, and the like. A blue light cut function can be imparted by mixing an absorber that absorbs light with a wavelength of 400 to 500 nm on the surface of a display, glasses, contact lenses, or the like, or by laminating a layer including an absorber that absorbs light with a wavelength of 400 to 500 nm.

For example, reference 1 describes the use of C.I. Solvent Yellow 33, which is a quinoline compound, as a compound that efficiently absorbs light near a wavelength of 440 nm among blue light.

prior art literature

patent documents

Patent Document 1: Japanese Patent Laid-Open No. 2015-17152

Contents of the invention

The problem to be solved by the invention

However, quinoline compounds such as C.I. Solvent Yellow 33 may not have sufficient weather resistance.

means to solve the problem

The present invention includes the following inventions.

[1] A compound comprising an anion having a partial structure represented by formula (X).

[In formula (X), ring W ¹ represents a ring structure having at least one substituent. ]

[2] The compound according to [1], wherein the anion having a partial structure represented by formula (X) is any one of the anion represented by formula (I) to the anion represented by formula (VIII).

[ ^In the formula, ring W1 represents the same meaning as above.

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ , Ring W ¹² , Ring W ¹³ and Ring W ¹⁴ each independently represent a ring structure, and this ring structure may have a substituent.

R ¹ , R ² , R ⁴ , R ⁵ , R ¹² , R ¹⁴ , R ¹⁵ , R ²² , R ²⁴ , R ²⁵ , R ³² , R ³⁴ , R ³⁵ , R ⁴² , R ⁴⁴ , R ⁴⁵ , R ⁵² , R ⁵⁴ , R ⁵⁵ , R ⁶² , R ⁶⁴ , R ⁶⁵ , R ⁷¹ , R ⁷² , R ⁷⁴ , R ⁷⁵ , R ⁸¹ , R ⁸² , R ⁸⁴ , R ⁸⁵ , R ⁹¹ , R ⁹² , R ⁹⁴ , R ⁹⁵ , R ¹⁰¹ , R ¹⁰² , R ¹⁰⁴ , R ¹⁰⁵ , R ¹¹¹ , R ¹¹² , R ¹¹⁴ , R ¹¹⁵ , R ¹²¹ , R ¹²² , R ¹²⁴ , R ¹²⁵ , R ¹³¹ , R ¹³² , R ¹³⁴ , and R ¹³⁵ independently represents an electron-withdrawing group.

R ³ represents a monovalent substituent.

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ and R ¹³³ represent monovalent substituents.

R ¹ and R ² may be connected to each other to form a ring.

R ² and R ³ may be connected to each other to form a ring.

R ³ and R ⁴ may be connected to each other to form a ring.

R ⁴ and R ⁵ may be connected to each other to form a ring.

R ¹² and R ¹³ may be connected to each other to form a ring.

R ¹³ and R ¹⁴ may be connected to each other to form a ring.

R ¹⁴ and R ¹⁵ may be connected to each other to form a ring.

R ²² and R ²³ may be connected to each other to form a ring.

R ²³ and R ²⁴ may be connected to each other to form a ring.

R ²⁴ and R ²⁵ may be connected to each other to form a ring.

R ³² and R ³³ may be connected to each other to form a ring.

R ³³ and R ³⁴ may be connected to each other to form a ring.

R ³⁴ and R ³⁵ may be connected to each other to form a ring.

R ⁴² and R ⁴³ may be connected to each other to form a ring.

R ⁴³ and R ⁴⁴ may be connected to each other to form a ring.

R ⁴⁴ and R ⁴⁵ may be connected to each other to form a ring.

R ⁵² and R ⁵³ may be connected to each other to form a ring.

R ⁵³ and R ⁵⁴ may be connected to each other to form a ring.

R ⁵⁴ and R ⁵⁵ may be connected to each other to form a ring.

R ⁶² and R ⁶³ may be connected to each other to form a ring.

R ⁶³ and R ⁶⁴ may be connected to each other to form a ring.

R ⁶⁴ and R ⁶⁵ may be connected to each other to form a ring.

R ⁷¹ and R ⁷² may be connected to each other to form a ring.

R ⁷⁴ and R ⁷⁵ may be connected to each other to form a ring.

R ⁸¹ and R ⁸² may be connected to each other to form a ring.

R ⁸⁴ and R ⁸⁵ may be connected to each other to form a ring.

R ⁹¹ and R ⁹² may be connected to each other to form a ring.

R ⁹⁴ and R ⁹⁵ may be connected to each other to form a ring.

R ¹⁰¹ and R ¹⁰² may be connected to each other to form a ring.

R ¹⁰⁴ and R ¹⁰⁵ may be connected to each other to form a ring.

R ¹¹¹ and R ¹¹² may be connected to each other to form a ring.

R ¹¹⁴ and R ¹¹⁵ may be connected to each other to form a ring.

R ¹²¹ and R ¹²² may be connected to each other to form a ring.

R ¹²⁴ and R ¹²⁵ may be connected to each other to form a ring.

R ¹³¹ and R ¹³² may be connected to each other to form a ring.

R ¹³² and R ¹³³ may be connected to each other to form a ring.

R ¹³³ and R ¹³⁴ may be connected to each other to form a ring.

R ¹³⁴ and R ¹³⁵ may be connected to each other to form a ring.

R ^x1 , R ^x4 and R ^x7 each independently represent a single bond or a divalent linking group.

R ^x2 and R ^x5 each independently represent a trivalent linking group.

R ^x3 and R ^x6 each independently represent a tetravalent linking group. ]

[3] The compound according to [2], wherein R ³ is an electron-withdrawing group.

[4] The compound according to [2] or [3], wherein at least one selected from R ¹ , R ² , R ³ , R ⁴ and R ⁵ is cyano, nitro, haloalkyl, halo Aryl, -CO-R ₁ , -CO-OR ₂ , -CO-NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , -CS-OR ₆ , -CS-SR ₇ , -SO- R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent a hydrocarbon group that may have a substituent or Halogen atom.), -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ or -SO ₃ H.

[5] The compound according to any one of [2] to [4], wherein at least one selected from R ¹ , R ² , R ³ , R ⁴ and R ⁵ is cyano, nitro, - CO-R ₁ , -CO-OR ₂ , -SO ₂ -R ₉ (R ₁ , R ₂ and R ₉ each independently represent a hydrocarbon group or a halogen atom which may have a substituent.), -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -OCF ₃ or -SCF ₃ .

[6] The compound according to any one of [2] to [5], wherein at least one selected from R ¹ , R ² , R ³ , R ⁴ and R ⁵ is cyano or nitro.

[7] The compound according to any one of [1] to [6], which exhibits maximum absorption between a wavelength of 400 nm and a wavelength of 550 nm.

[8] The compound according to any one of [1] to [7], which has a molar absorption coefficient at the maximum absorption wavelength of 0.5 or more.

[9] The compound according to any one of [1] to [8], which satisfies the following formula (a).

ε(λ _max )/ε(λ _max +30nm)≥10 (a)

[wherein, ε(λmax) represents the molar absorptivity at the maximum absorption wavelength (λ _max ).

ε(λ _max +30nm) represents the molar absorption coefficient at the wavelength of the maximum absorption wavelength (λ _max )+30nm.

It should be noted that the unit of the molar absorptivity is L/(g·cm). ]

[10] A composition comprising the compound described in any one of [1] to [9].

[11] A molded article obtained by molding the resin composition described in [10].

[12] The molded article according to [11], which has a transmittance at a wavelength of 440 nm of 50% or less.

Invention effect

The present invention provides a novel compound that sufficiently absorbs light near a wavelength of 440 nm and has high weather resistance.

detailed description

The compound of the present invention is an anionic compound (hereinafter, may be referred to as compound (X)) having a partial structure represented by formula (X).

[In formula (X), ring W ¹ represents a ring having at least one substituent. ]

^The ring structure of ring W1 is not particularly limited. Ring W ¹ may be a single ring or a condensed ring.

Ring W1 may be ^a heterocyclic ring containing a heteroatom (such as an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a constituent element of the ring, or may be an aliphatic hydrocarbon ring containing a carbon atom and a hydrogen atom.

The ring W1 is usually ^a ring having 5 to 18 carbon atoms, preferably a 5 to 7-membered ring structure, more preferably a 6-membered ring structure. The ring W ¹ is preferably a ring structure having 5 to 7 carbon atoms, more preferably a ring structure having 6 carbon atoms.

Ring W ¹ is preferably a monocyclic ring.

Ring W ¹ is preferably an aliphatic hydrocarbon ring (alicyclic hydrocarbon group).

^The ring W1 includes, for example, the following ring structures.

Ring W1 has at least ^one substituent present between two double bonds bonded to ring ^W1 . That is, the compound of the present invention is preferably a compound containing an anion having a partial structure represented by formula (X-1).

[In formula (X-1), ring W ¹ represents the same meaning as above, and R ³ represents a monovalent substituent. ]

^R3 is not particularly limited as long as it is a monovalent substituent, and examples thereof include a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron-withdrawing group, an electron-donating group, and a heterocyclic group.

Examples of the monovalent aliphatic hydrocarbon group represented by ^R 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 and other straight-chain or branched-chain alkyl groups with 1 to 25 carbon atoms: cyclopropyl, cyclobutyl, cyclo Cycloalkyl groups with 3 to 25 carbon atoms such as pentyl and cyclohexyl; cycloalkyl groups with 4 to 25 carbon atoms such as cyclohexylmethyl; alkylcycloalkanes with 4 to 25 carbon atoms such as isobornyl base. It is preferably a linear or branched alkyl group having 1 to 12 carbon atoms.

基、三亚苯基、四苯基、芘基、苝基、晕苯基(日文：コロネニル基)、联苯基等碳原子数6～18的芳基；苄基、苯基乙基、萘基甲基等碳原子数7～18的芳烷基；苯氧基乙基、苯氧基二乙二醇基、苯氧基聚亚烷基二醇基之类的芳基烷氧基等，优选为碳原子数6～18的芳基，更优选为苯基或苄基。As the monovalent aromatic hydrocarbon group represented by ^R3 , phenyl, naphthyl, anthracenyl, naphthacene, pentacene, phenanthrenyl,

Aryl groups with 6 to 18 carbon atoms such as triphenylene, tetraphenyl, pyrenyl, perylenyl, coronene phenyl (Japanese: Coronyl), biphenyl, etc.; benzyl, phenylethyl, naphthyl Aralkyl groups with 7 to 18 carbon atoms such as methyl groups; arylalkoxy groups such as phenoxyethyl groups, phenoxydiethylene glycol groups, and phenoxy polyalkylene glycol groups, etc., preferably It is an aryl group having 6 to 18 carbon atoms, more preferably a phenyl group or a benzyl group.

Examples of the electron-donating group represented by ^R include hydroxyl; carbon such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy; Alkoxy groups with 1 to 12 atoms; amino, monomethylamino, monoethylamino, dimethylamino, diethylamino, methylethylamino, etc. can be replaced by 1 or 2 carbon atoms 6's alkyl-substituted amino group, etc.

As the heterocyclic group represented by ^R3 , pyrrolidine ring group, pyrroline ring group, imidazolidine ring group, imidazoline ring group, oxazoline ring group, thiazoline ring group, piperidine ring group, Aliphatics with 4 to 20 carbon atoms such as line ring group, piperazine ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group and furan ring group An aromatic heterocyclic group or an aromatic heterocyclic group having 3 to 20 carbon atoms, etc.

Examples of the electron-withdrawing group represented by R ³ include a halogen atom, a nitro group, a cyano group, a carboxyl group, a haloalkyl group, a haloaryl group, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, and a group represented by the formula (z-1).

*-X ¹ -R ²²² (z-1)

[In formula (z-1), R ²²² represents a hydrogen atom, a halogen atom, or a hydrocarbon group which may have a substituent.

X ¹ means -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO-, -SO ₂ -, -NR ²²³ CO- or -CONR ²²⁴ - .

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

* Indicates a connection key. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of haloalkyl groups include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluoro-sec-butyl, perfluoro-t-butyl, perfluoropentyl, Haloalkyl groups having 1 to 25 carbon atoms such as perfluorohexyl, dichloromethyl, bromomethyl, and iodomethyl. It is preferably a haloalkyl group having 1 to 12 carbon atoms, more preferably a fluoroalkyl group having 1 to 12 carbon atoms, and even more preferably a perfluoroalkyl group having 1 to 12 carbon atoms.

Examples of the halogenated aryl group include halogenated aryl groups having 6 to 18 carbon atoms such as fluorophenyl, chlorophenyl, and bromophenyl, preferably fluoroaryl groups having 6 to 18 carbon atoms, more preferably carbon The perfluoroaryl group having 6 to 12 atoms is more preferably pentafluorophenyl.

X ¹ is preferably -CO-, -COO- or -SO ₂ -.

Examples of the halogen atom represented by ^R222 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the hydrocarbon group represented by ^R222 include aliphatic hydrocarbon groups having 1 to 25 carbon atoms, aromatic hydrocarbon groups having 6 to 18 carbon atoms, and the like.

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1- Methylbutyl, 3-methylbutyl, n-octyl, n-decyl, 2-hexyl-octyl, cyclohexyl, and other linear, branched, and cyclic alkyl groups with 1 to 25 carbon atoms, It is preferably an alkyl group having 1 to 12 carbon atoms.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include aryl groups having 6 to 18 carbon atoms such as phenyl, naphthyl, anthracenyl, and biphenyl; benzyl, phenylethyl, and naphthylmethyl Aralkyl groups with 7 to 18 carbon atoms, etc.

Examples of substituents that the hydrocarbon group represented by ^R222 may have include halogen atoms, hydroxyl groups, and the like.

Examples of alkyl groups having 1 to 6 carbon atoms represented by ^R223 and ^R224 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl Straight-chain or branched C1-C6 alkyl group such as n-hexyl group, 1-methylbutyl group, etc.

The group represented by formula (z-1) is preferably -CO-R ₁ , -CO-OR ₂ , -CO-NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , -CS-OR ₆ , -CS-SR ₇ , -SO-R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent a hydrocarbon group or a halogen atom which may have a substituent.),

More preferably -CO-R ₁ , -CO-OR ₂ , -SO ₂ -R ₉ ,

More preferably -SO ₂ -R ₉ ,

More preferably -SO ₂ -R ₁₀ (R ₁₀ is an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms), -SO ₂ CF ₃ , -SO ₂ CHF ₂ , -SO ₂ CH ₂ F.

^R3 is preferably an electron-withdrawing group,

More preferably cyano, nitro, haloalkyl, haloaryl, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -CO- NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , -CS-OR ₆ , -CS-SR ₇ , -SO-R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R8 and R9 each independently represent a hydrocarbon group or a halogen atom that may have a substituent.), -OCF ₃ or -SCF ₃ ,

More preferably, cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -SO _{2 -R9} ,

Still more preferably cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SO ₂ CF ₃ , -SO ₂ -R ₁₀ ,

Very particular preference is given to cyano or nitro.

The ring W ¹ may have a substituent other than the substituent indicated by R ³ . Examples of such substituents include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and nonyl; Aliphatic hydrocarbon group with 1 to 25 atoms (preferably an alkyl group with 1 to 12 carbon atoms); fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2,2-pentafluoroethyl and other haloalkyl groups with 1 to 12 carbon atoms; Methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and other alkoxy groups with 1 to 12 carbon atoms; methylthio, ethylthio, propylthio, butylthio , pentylthio, hexylthio and other alkylthio groups with 1 to 12 carbon atoms; monofluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 1,1,2 , 2,2-pentafluoroethoxy and other fluoroalkoxy groups with 1 to 12 carbon atoms; trifluoromethylthioalkoxy and other fluoroalkoxy groups with 1 to 12 carbon atoms; amino, methyl Amino group, ethylamino group, dimethylamino group, diethylamino group, methylethyl group, etc., which may be substituted by one or two alkyl groups with 1 to 6 carbon atoms; carbamoyl group, N-methylamino group Formyl, N,N-dimethylcarbamoyl and other carbamoyl groups whose N-position can be substituted by an alkyl group with 1 to 6 carbon atoms; methylcarbonyloxy, ethylcarbonyloxy and other carbon atoms with 2 Alkylcarbonyloxy to 12; alkylsulfonyl groups with 1 to 12 carbon atoms such as methylsulfonyl and ethylsulfonyl; aromatics with 6 to 25 carbon atoms such as phenyl, naphthyl, and diphenyl Hydrocarbyl (preferably aryl with 6 to 18 hydrocarbons); arylsulfonyl with 6 to 12 carbon atoms such as phenylsulfonyl; alkoxy with 1 to 12 carbon atoms such as methoxysulfonyl and ethoxysulfonyl Sulfonyl; acetyl, ethylcarbonyl and other acyl groups with 2 to 12 carbon atoms; aldehyde group; methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl and other acyl groups with 2 to 12 carbon atoms Alkoxycarbonyl; methoxythiocarbonyl, ethoxythiocarbonyl and other alkoxythiocarbonyl groups with 2 to 12 carbon atoms; cyano; nitro; hydroxyl; thiol; sulfo; aminomethyl Acyl; Carboxyl; -SF ₃ ; -SF ₅ etc.

The anion having a partial structure represented by formula (X-1) is preferably an anion represented by formula (I) to an anion represented by formula (IV) or an anion represented by formula (VIII).

[In the formula, the rings W ¹ and R ³ represent the same meanings as above, respectively.

Ring W ² , ring W ³ , ring W ⁴ , ring W ⁵ , ring W ⁶ , ring W ⁷ and ring W ¹⁴ each independently represent a ring structure, which may have a substituent.

R ¹ , R ² , R ⁴ , R ⁵ , R ¹² , R ¹⁴ , R ¹⁵ , R ²² , R ²⁴ , R ²⁵ , R ³² , R ³⁴ , R ³⁵ , R ⁴² , R ⁴⁴ , R ⁴⁵ , R ⁵² , R ⁵⁴ , R ⁵⁵ , R ⁶² , R ⁶⁴ , R ⁶⁵ , R ¹³¹ , R ¹³² , R ¹³⁴ and R ¹³⁵ each independently represent an electron-withdrawing group.

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ and R ¹³³ represent monovalent substituents.

R ¹ and R ² may be connected to each other to form a ring.

R ² and R ³ may be connected to each other to form a ring.

R ³ and R ⁴ may be connected to each other to form a ring.

R ⁴ and R ⁵ may be connected to each other to form a ring.

R ¹² and R ¹³ may be connected to each other to form a ring.

R ¹³ and R ¹⁴ may be connected to each other to form a ring.

R ¹⁴ and R ¹⁵ may be connected to each other to form a ring.

R ²² and R ²³ may be connected to each other to form a ring.

R ²³ and R ²⁴ may be connected to each other to form a ring.

R ²⁴ and R ²⁵ may be connected to each other to form a ring.

R ³² and R ³³ may be connected to each other to form a ring.

R ³³ and R ³⁴ may be connected to each other to form a ring.

R ³⁴ and R ³⁵ may be connected to each other to form a ring.

R ⁴² and R ⁴³ may be connected to each other to form a ring.

R ⁴³ and R ⁴⁴ may be connected to each other to form a ring.

R ⁴⁴ and R ⁴⁵ may be connected to each other to form a ring.

R ⁵² and R ⁵³ may be connected to each other to form a ring.

R ⁵³ and R ⁵⁴ may be connected to each other to form a ring.

R ⁵⁴ and R ⁵⁵ may be connected to each other to form a ring.

R ⁶² and R ⁶³ may be connected to each other to form a ring.

R ⁶³ and R ⁶⁴ may be connected to each other to form a ring.

R ⁶⁴ and R ⁶⁵ may be connected to each other to form a ring.

R ¹³¹ and R ¹³² may be connected to each other to form a ring.

R ¹³² and R ¹³³ may be connected to each other to form a ring.

R ¹³³ and R ¹³⁴ may be connected to each other to form a ring.

R ¹³⁴ and R ¹³⁵ may be connected to each other to form a ring.

R ^x1 and R ^x7 each independently represent a single bond or a divalent linking group.

^Rx2 represents a trivalent linking group.

^Rx3 represents a tetravalent linking group. ]

The ring structures of ring W ² , ring W ³ , ring W ⁴ , ring W ⁵ , ring W ⁶ , ring W ⁷ and ring W ¹⁴ are not particularly limited. Each of ring W ² to ring W ⁷ and ring ¹⁴ may be a single ring or a condensed ring. Ring W ² to W ⁷ and ring ¹⁴ may be heterocyclic rings containing heteroatoms (for example, oxygen atoms, sulfur atoms, nitrogen atoms, etc.) as ring constituents.

Ring W ² to W ⁷ and ring ¹⁴ are usually rings having 5 to 18 carbon atoms, preferably have a 5 to 7-membered ring structure, and more preferably have a 6-membered ring structure. Ring W ² to W ⁷ and ring ¹⁴ preferably have a ring structure having 5 to 7 carbon atoms, more preferably a ring structure having 6 carbon atoms.

Ring W ² to W ⁷ and ring ¹⁴ are each independently preferably a monocyclic ring.

Ring W ² to ring W ⁷ and ring ¹⁴ may have substituents, and specifically, the same substituents as substituents that ring W ¹ may have other than the substituent represented by R ³ may be mentioned.

The substituents of ring W ² to ring W ⁷ and ring ¹⁴ are preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or An amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms.

Specific examples of ring W ² to ring W ⁷ and ring ¹⁴ include the same groups as specific examples of ring W ¹ .

The monovalent substituents represented by R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ and R ¹³³ are not particularly limited, and examples thereof include the same groups as the monovalent substituents represented by R ³ . Specifically, a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron-withdrawing group, an electron-donating group, a heterocyclic group, and the like are exemplified.

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ and R ¹³³ are each independently preferably an electron-withdrawing group,

More preferably cyano, nitro, haloalkyl, haloaryl, -CO-R ₁ , -CO-OR ₂ , -CO-NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , - CS-OR ₆ , -CS-SR ₇ , -SO-R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent a hydrocarbon group or a halogen atom which may have a substituent.), -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₂ H or -SO ₃ H,

More preferably, cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -SO _{2 -R9} ,

Still more preferably cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SO ₂ CF ₃ , -SO ₂ -R ₁₀ ,

Very particular preference is given to cyano or nitro.

as R ¹ , R ² , R ⁴ , R ⁵ , R ¹² , R ¹⁴ , R ¹⁵ , R ²² , R ²⁴ , R ²⁵ , R ³² , R ³⁴ , R ³⁵ , R ⁴² , R ⁴⁴ , R ⁴⁵ , R ⁵² , R ⁵⁴ , R ⁵⁵ , R ⁶² , R ⁶⁴ , R ⁶⁵ , R ¹³¹ , R ¹³² , R ¹³⁴ , and R ¹³⁵ represent electron-withdrawing groups, including electron-withdrawing groups represented by R ³ same group.

More preferably R ¹ , R ² , R ⁴ , R ⁵ , R ¹² , R ¹⁴ , R ¹⁵ , R ²² , R ²⁴ , R ²⁵ , R ³² , R ³⁴ , R ³⁵ , R ⁴² , R ⁴⁴ , R ⁴⁵ , R ⁵² , R ⁵⁴ , R ⁵⁵ , R ⁶² , R ⁶⁴ , R ⁶⁵ , R ¹³¹ , R ¹³² , R ¹³⁴ and R ¹³⁵ are each independently cyano, nitro, haloalkyl, haloaryl, -CO- R ₁ , -CO-OR ₂ , -CO-NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , -CS-OR ₆ , -CS-SR ₇ , -SO-R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent a hydrocarbon group or a halogen atom which may have a substituent.), - OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₂ H or -SO ₃ H,

More preferably, cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -SO _{2 -R9} ,

Still more preferably cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SO ₂ CF ₃ , -SO ₂ -R ₁₀ ,

Very particular preference is given to cyano or nitro.

R ¹ and R ² may be bonded to each other to form a ring. The ring formed by bonding R ¹ and R ² to each other may be a single ring or a condensed ring, but is preferably a single ring. The ring formed by bonding R ¹ and R ² to each other may contain a heteroatom (nitrogen atom, oxygen atom, sulfur atom) or the like as a constituent element of the ring.

The ring formed by bonding R ¹ and R ² to each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.

Examples of the ring formed by R ¹ and R ² being bonded to each other include ring structures described below and the like.

[In the formula, * represents a connecting key. ]

The ring formed by bonding R1 and R2 to each other is preferably ^formula (w- ¹ ) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ⁴ and R ⁵ to each other include the same rings as the ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting R ⁴ and R ⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹⁴ and R ¹⁵ to each other include the same rings as the ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting ^R14 and ^R15 to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ²⁴ and R ²⁵ to each other include the same rings as the ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting ^R24 and ^R25 to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ³⁴ and R ³⁵ to each other include the same rings as the ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting ^R34 and ^R35 to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ⁴⁴ and R ⁴⁵ to each other include the same rings as the ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting R ⁴⁴ and R ⁴⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

^The ring formed by linking ^R54 and ^R55 to each other includes the same ring as the ring formed by linking R1 and ^R2 to each other. The ring formed by connecting ^R54 and ^R55 to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ⁶⁴ and R ⁶⁵ to each other include the same ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting ^R64 and ^R65 to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹³¹ and R ¹³² to each other include the same rings as the ring formed by connecting R ¹ and R ² to each other. The ring formed by connecting R ¹³¹ and R ¹³² to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by linking R ¹³⁴ and R ¹³⁵ to each other include the same ring formed by linking R ¹ and R ² to each other. The ring formed by connecting R ¹³⁴ and R ¹³⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula ( w-35) to the ring structure shown in formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

R ² and R ³ may be connected to each other to form a ring. The ring formed by linking R2 and ^R3 includes a ^double bond bonded to ring W1 as ^a constituent element of the ring. ^In addition, the ring formed by linking R2 and ^R3 forms ^a condensed ring with ring W1. Examples of the condensed ring formed by the bonded ring formed by R ² and R ³ and the ring W ¹ include ring structures represented by formulas (w11-1) to (w11-12) described below.

[ ^In the formula, ring W1 represents the same meaning as above.

* ¹ represents the connection bond with R1, * ² represents the connection bond with R4, and * ³ represents the connection bond with R5.

R ^f1 , R ^f2 and R ^f3 each independently represent an electron-withdrawing group, a hydrocarbon group, or a hydroxyl group.

m1 represents an integer of 0-6, m2 represents an integer of 0-4, and m3 represents an integer of 0-2. ]

More specific examples of the condensed ring formed by the ring formed by R ² and R ³ being bonded to each other and the ring W ¹ include ring structures described below and the like.

R ¹² and R ¹³ may be connected to each other to form a ring. The ring formed by linking R ¹² and R ¹³ includes a double bond bonded to ring W ² as a constituent element of the ring. In addition, the ring formed by linking R ¹² and R ¹³ forms a condensed ring with ring W ² . Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ²² and R ²³ may be connected to each other to form a ring. The ring formed by linking R ²² and R ²³ includes a double bond bonded to ring W ³ as a constituent element of the ring. ^In addition, the ring formed by linking ^R22 and ^R23 forms a condensed ring with ring W3. Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ³² and R ³³ may be connected to each other to form a ring. The ring formed by linking R ³² and R ³³ includes a double bond bonded to ring W ⁴ as a constituent element of the ring. In addition, the ring formed by linking ^R32 and ^R33 forms a condensed ring with ring W4 ^. Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ⁴² and R ⁴³ may be connected to each other to form a ring. The ring formed by linking R ⁴² and R ⁴³ includes a double bond bonded to ring W ⁵ as a constituent element of the ring. In addition, the ring formed by linking R ⁴² and R ⁴³ forms a condensed ring with ring W ⁵ . Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ⁵² and R ⁵³ may be connected to each other to form a ring. The ring formed by linking R ⁵² and R ⁵³ to the double bond to ring W ⁶ is included as a constituent element of the ring. In addition, the ring formed by linking ^{R52 and R53 forms} a condensed ring with ring ^W6 . Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ⁶² and R ⁶³ may be connected to each other to form a ring. The ring formed by linking R ⁶² and R ⁶³ includes a double bond bonded to ring W ⁷ as a constituent element of the ring. In addition, the ring formed by linking R ⁶² and R ⁶³ forms a condensed ring with ring W ⁷ . Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ¹³² and R ¹³³ may be connected to each other to form a ring. The ring formed by linking R ¹³² and R ¹³³ includes a double bond bonded to ring W ¹⁴ as a constituent element of the ring.

In addition, the ring formed by linking R ¹³² and R ¹³³ forms a condensed ring with ring W ¹⁴ .

Specifically, the same ring as the condensed ring formed by the ring formed by ^R2 and ^R3 bonded to each other and the ring ^W1 can be mentioned.

R ³ and R ⁴ may be connected to each other to form a ring. The ring formed by linking R ³ and R ⁴ includes a double bond bonded to ring W ¹ as a constituent element of the ring. ^In addition, the ring formed by linking ^R3 and R4 forms ^a condensed ring with ring W1. As the condensed ring formed by the ring formed by R ³ and R ⁴ being bonded to each other and the ring W ¹ , specifically, the rings described below are exemplified.

[ ^In the formula, ring W1 represents the same meaning as above.

* ⁴ represents the connection bond with R1, * ⁵ represents the connection bond with R2, and * ⁶ represents the connection bond with R5.

R ^f4 , R ^f5 , and R ^f6 each independently represent an electron-withdrawing group, a hydrocarbon group, or a hydroxyl group.

m4 represents an integer of 0-6, m5 represents an integer of 0-4, and m6 represents an integer of 0-2. ]

More specific examples of the condensed ring formed by the ring formed by R ³ and R ⁴ being bonded to each other and the ring W ¹ include ring structures described below, and the like.

R ¹³ and R ¹⁴ may be connected to each other to form a ring. The ring formed by linking R ¹³ and R ¹⁴ includes a double bond bonded to ring W ² as a constituent element of the ring. In addition, the ring formed by linking R ¹³ and R ¹⁴ forms a condensed ring with ring W ² . Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

R ²³ and R ²⁴ may be connected to each other to form a ring. The ring formed by linking R ²³ and R ²⁴ includes a double bond bonded to ring W ³ as a constituent element of the ring. ^In addition, the ring formed by linking ^R23 and ^R24 forms a condensed ring with ring W3. Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

R ³³ and R ³⁴ may be connected to each other to form a ring. The ring formed by linking R ³³ and R ³⁴ includes a double bond bonded to ring W ⁴ as a constituent element of the ring. In addition, the ring formed by linking ^R33 and ^R34 forms a condensed ring with ring W4 ^. Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

R ⁴³ and R ⁴⁴ may be connected to each other to form a ring. The ring formed by linking R ⁴³ and R ⁴⁴ includes a double bond bonded to ring W ⁵ as a constituent element of the ring. In addition, the ring formed by linking R ⁴³ and R ⁴⁴ forms a condensed ring with ring W ⁵ . Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

R ⁵³ and R ⁵⁴ may be connected to each other to form a ring. The ring formed by linking R ⁵³ and R ⁵⁴ includes a double bond bonded to ring W ⁶ as a constituent element of the ring. In addition, the ring formed by linking R ⁵³ and R ⁵⁴ forms a condensed ring with ring W ⁶ . Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

R ⁶³ and R ⁶⁴ may be connected to each other to form a ring. The ring formed by linking R ⁶³ and R ⁶⁴ includes a double bond bonded to ring W ⁷ as a constituent element of the ring. In addition, the ring formed by linking R ⁶³ and R ⁶⁴ forms a condensed ring with ring W ⁷ . Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

R ¹³³ and R ¹³⁴ may be connected to each other to form a ring. The ring formed by linking R ¹³³ and R ¹³⁴ includes a double bond bonded to ring W ¹⁴ as a constituent element of the ring. In addition, the ring formed by linking R ¹³³ and R ¹³⁴ forms a condensed ring with ring W ¹⁴ . Specifically, the same ring as the condensed ring formed by the ring formed by ^R3 and R4 bonded to each other and the ring ^W1 can be mentioned ^.

Examples of the divalent linking group represented by R ^x1 and R ^x7 each independently include a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms that may have a substituent or a carbon number 6 that may have a substituent. -18 divalent aromatic hydrocarbon groups, etc. The -CH ₂ - contained in the above-mentioned divalent aliphatic hydrocarbon group and divalent aromatic hydrocarbon group may be replaced by -O-, -S-, -NR ^1B - (R ^1B represents a hydrogen atom or an alkane having 1 to 6 carbon atoms base), -CO-, -SO ₂ -, -SO-, -PO ₃ -substitution.

In addition, examples of substituents that the above-mentioned divalent aliphatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxyl group, an amino group, an aryl group having 6 to 16 carbon atoms, and the like.

As a substituent which the said divalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxyl group, an amino group, an aldehyde group etc. are mentioned.

Specific examples of the divalent linking group represented by R ^x1 and R ^x7 include linking groups described below. In the formula, * represents a connection key.

The divalent linking groups represented by R ^x1 and R ^x7 are each independently preferably a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent and a divalent aliphatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent. A divalent aromatic hydrocarbon group (the divalent aliphatic hydrocarbon group and the -CH ₂ - contained in the divalent aromatic hydrocarbon group may be replaced by -O-, -S-, -NR ^1B -, -CO-, -SO ₂ -substituted), more preferably a linking group described below.

Examples of the trivalent linking group represented by R ^x2 include an optionally substituted trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms or an optionally substituted trivalent aliphatic hydrocarbon group having 6 to 18 carbon atoms. Aromatic hydrocarbon group. The -CH ₂ - contained in the above-mentioned trivalent aliphatic hydrocarbon group and the above-mentioned trivalent aromatic hydrocarbon group may be replaced by -O-, -S-, -CS-, -CO-, -SO-, -SO ₂ -, - NR ^11B - (R ^11B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) Substitution.

As a substituent which the said trivalent aliphatic hydrocarbon group and the said trivalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxyl group, an amino group etc. are mentioned.

The trivalent linking group represented by R ^x2 is preferably a trivalent aliphatic hydrocarbon group with 1 to 18 carbon atoms (the -CH ₂ - contained in the above trivalent aliphatic hydrocarbon group can be replaced by -O-, -CO- , -SO ₂ -substituted.) and a trivalent aromatic hydrocarbon group with 6 to 18 carbon atoms (the -CH ₂ - contained in the above trivalent aromatic hydrocarbon group can be replaced by -O-, -CO-, -SO ₂ -replace.).

Specific examples of the trivalent linking group represented by R ^x2 include linking groups described below.

Examples of the tetravalent linking group represented by R ^x3 include a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a tetravalent aliphatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Aromatic hydrocarbon group. The -CH ₂ - contained in the above-mentioned tetravalent aliphatic hydrocarbon group and the above-mentioned tetravalent aromatic hydrocarbon group may be replaced by -O-, -S-, -CS-, -CO-, -SO-, -SO ₂ -, - NR ^11C - (R ^11C represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) Substitution.

As a substituent which the said tetravalent aliphatic hydrocarbon group and the said tetravalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxyl group, an amino group etc. are mentioned.

The 4-valent linking group represented by R ^x3 is preferably a 4-valent aliphatic hydrocarbon group with 1 to 18 carbon atoms (the -CH ₂ - contained in the above-mentioned 4-valent aliphatic hydrocarbon group can be replaced by -O-, -CO- , -SO ₂ -substituted.) and a 4-valent aliphatic hydrocarbon group with 6 to 18 carbon atoms (the -CH ₂ - contained in the above-mentioned 4-valent aromatic hydrocarbon group can be replaced by -O-, -CO-, -SO ₂ -replace.).

Specific examples of the tetravalent linking group represented by R ^x3 include linking groups described below.

The anion represented by formula (I) is more preferably an anion represented by formula (I-A).

[In the formula (IA), R ¹ , R ² , R ³ , R ⁴ and R ⁵ respectively represent the same meanings as above.

_RE1 , _RE2 , _RE3 , _RE4 , _RE5 and _RE6 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 25 carbon atoms, or an alkoxy group. ]

In formula (IA), at least one selected from R ¹ , R ² , R ³ , R ⁴ and R ⁵ is preferably cyano, nitro, haloalkyl, haloaryl, -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -CO-NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , -CS-OR ₆ , -CS-SR ₇ , -SO-R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ Each independently represents a hydrocarbon group or a halogen atom which may have a substituent.) -OCF ₃ or -SCF ₃ ,

More preferably cyano, nitro, -OCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -SO ₂ -R ₉ ,

More preferably cyano, nitro, -CO-R ₁ , -CO-OR ₂ , -SO ₂ -R ₉ , -OCF ₃ , -SCF ₃ or -SF ₅ ,

Still more preferably cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SO ₂ CF ₃ , -SO ₂ -R ₁₀ (R ₁₀ is a C6-18 carbon atom which may have a substituent Aromatic hydrocarbon group),

Very particular preference is given to cyano or nitro.

Examples of the anion represented by the formula (I) include the anions described below.

Examples of the anion represented by the formula (II) include the anions described below.

Examples of the anion represented by the formula (III) include the anions described below.

Examples of the anion represented by the formula (IV) include the anions described below.

Examples of the anion represented by the formula (VIII) include the anions described below.

When at least one substituent of ring W ¹ is other than R ³ , examples of the anion having a partial structure represented by formula (X) include anions represented by formula (V) to formula (VII) The anions shown, etc.

[In the formula, the rings W ¹ , R ¹ , R ² , R ⁴ and R ⁵ have the same meanings as above, respectively.

Ring W ⁸ , ring W ⁹ , ring W ¹⁰ , ring W ¹¹ , ring W ¹² and ring W ¹³ each independently represent a ring structure, which may have a substituent.

R ⁷¹ , R ⁷² , R ⁷⁴ , R ⁷⁵ , R ⁸¹ , R ⁸² , R ⁸⁴ , R ⁸⁵ , R ⁹¹ , R ⁹² , R ⁹⁴ , R ⁹⁵ , R ¹⁰¹ , R ¹⁰² , R ¹⁰⁴ , R ¹⁰⁵ , R ¹¹¹ , R ¹¹² , R ¹¹⁴ , R ¹¹⁵ , R ¹²¹ , R ¹²² , R ¹²⁴ and R ¹²⁵ each independently represent an electron-withdrawing group.

R ⁷¹ and R ⁷² may be connected to each other to form a ring.

R ⁷⁴ and R ⁷⁵ may be connected to each other to form a ring.

R ⁸¹ and R ⁸² may be connected to each other to form a ring.

R ⁸⁴ and R ⁸⁵ may be connected to each other to form a ring.

R ⁹¹ and R ⁹² may be connected to each other to form a ring.

R ⁹⁴ and R ⁹⁵ may be connected to each other to form a ring.

R ¹⁰¹ and R ¹⁰² may be connected to each other to form a ring.

R ¹⁰⁴ and R ¹⁰⁵ may be connected to each other to form a ring.

R ¹¹¹ and R ¹¹² may be connected to each other to form a ring.

R ¹¹⁴ and R ¹¹⁵ may be connected to each other to form a ring.

R ¹²¹ and R ¹²² may be connected to each other to form a ring.

R ¹²⁴ and R ¹²⁵ may be connected to each other to form a ring.

R ^x4 represents a single bond or a divalent linking group.

R ^x5 represents a trivalent linking group.

^Rx6 represents a tetravalent linking group. ]

The ring structures of ring W ⁸ , ring W ⁹ , ring W ¹⁰ , ring W ¹¹ , ring W ¹² and ring W ¹³ are not particularly limited. Each of ring W ⁹ to ring W ¹² may be a single ring or a condensed ring. Ring W ⁹ to W ¹² may be heterocyclic rings containing heteroatoms (for example, oxygen atoms, sulfur atoms, nitrogen atoms, etc.) as ring constituents.

Ring W ⁹ to W ¹² are usually rings having 5 to 18 carbon atoms, preferably have a 5 to 7-membered ring structure, and more preferably have a 6-membered ring structure. Ring W ⁹ to W ¹² preferably have a ring structure having 5 to 7 carbon atoms, more preferably a ring structure having 6 carbon atoms.

Ring W ⁹ to W ¹² are each independently preferably a monocyclic ring.

The ring W ⁹ to the ring W ¹² may have a substituent, and specifically, the same substituents as the substituent that the ring W ¹ may have other than the substituent represented by R ³ may be mentioned.

The substituents of ring W ⁹ to ring W ¹² are preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or a carbon An amino group substituted with an alkyl group having 1 to 6 atoms.

Specific examples of the ring W ⁹ to W ¹² include the same examples as the specific example of the ring W ¹ .

As R ⁷¹ , R ⁷² , R ⁷⁴ , R ⁷⁵ , R ⁸¹ , R ⁸² , R ⁸⁴ , R ⁸⁵ , R ⁹¹ , R ⁹² , R ⁹⁴ , R ⁹⁵ , R ¹⁰¹ , R ¹⁰² , R ¹⁰⁴ , R ¹⁰⁵ , R The electron-withdrawing groups represented by ¹¹¹ , R ¹¹² , R ¹¹⁴ , R ¹¹⁵ , R ¹²¹ , R ¹²² , R ¹²⁴ , and R ¹²⁵ include the same electron-withdrawing groups as those represented by R ³ group.

R ⁷¹ , R ⁷² , R ⁷⁴ , R ⁷⁵ , R ⁸¹ , R ⁸² , R ⁸⁴ , R ⁸⁵ , R ⁹¹ , R ⁹² , R ⁹⁴ , R ⁹⁵ , R ¹⁰¹ , R ¹⁰² , R ¹⁰⁴ , R ¹⁰⁵ , R ¹¹¹ , R ¹¹² , R ¹¹⁴ , R ¹¹⁵ , R ¹²¹ , R ¹²² , R ¹²⁴ and R ¹²⁵ are each independently preferably cyano, nitro, haloalkyl, haloaryl, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -CO-NR ₃ R _3k , -CO-SR ₄ , -CS-R ₅ , -CS-OR ₆ , -CS-SR ₇ , -SO-R ₈ , -SO ₂ -R ₉ (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent that they may have Hydrocarbyl or halogen atom of the substituent.), -OCF ₃ or -SCF ₃ ,

More preferably cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -SO _{2 -R9} ,

More preferably cyano, nitro, -CO-R ₁ , -CO-OR ₂ , -SO ₂ -R ₉ , -OCF ₃ , -SCF ₃ or -SF ₅ ,

Still more preferably cyano, nitro, -OCF ₃ , -SCF ₃ , -SF ₅ , -SO ₂ CF ₃ , -SO ₂ -R ₁₀ (R ₁₀ is a C6-18 carbon atom which may have a substituent Aromatic hydrocarbon group),

Very particular preference is given to cyano or nitro.

R ⁷¹ and R ⁷² may be bonded to each other to form a ring. The ring formed by bonding R ⁷¹ and R ⁷² to each other may be a single ring or a condensed ring, and is preferably a single ring. The ring formed by bonding R ⁷¹ and R ⁷² to each other may contain a heteroatom (nitrogen atom, oxygen atom, sulfur atom) or the like as a constituent element of the ring.

The ring formed by bonding R ⁷¹ and R ⁷² to each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.

Examples of the ring formed by bonding R ⁷¹ and R ⁷² to each other include the same rings as the ring formed by bonding R ¹ and R ² to each other.

The ring formed by bonding R ⁷¹ and R ⁷² to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) ~ formula (w-42) and the ring shown in formula (w-44), more preferably formula (w-1) ~ formula (w-6), formula (w-13), formula ( w-35), the ring structure shown in formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ⁷⁴ and R ⁷⁵ to each other include the same rings as the ring formed by connecting R ⁷¹ and R ⁷² to each other. The ring formed by bonding R ⁷⁴ and R ⁷⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ⁸¹ and R ⁸² to each other include the same rings as the ring formed by connecting R ⁷¹ and R ⁷² to each other. The ring formed by bonding R ⁸¹ and R ⁸² to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ⁸⁴ and R ⁸⁵ to each other include the same rings as the ring formed by connecting R ⁷¹ and R ⁷² to each other. The ring formed by bonding R ⁸⁴ and R ⁸⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by linking ^R91 and ^R92 to each other include the same rings as the ring formed by linking ^R71 and ^R72 to each other. The ring formed by R ⁹¹ and R ⁹² bonding to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting ^R94 and ^R95 to each other include the same rings as the ring formed by connecting ^R71 and ^R72 to each other. The ring formed by bonding R ⁹⁴ and R ⁹⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹⁰¹ and R ¹⁰² to each other include the same rings as the ring formed by connecting R ⁷¹⁷¹ and R ⁷²⁷² to each other. The ring formed by bonding R ¹⁰¹ and R ¹⁰² to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹⁰⁴ and R ¹⁰⁵ to each other include the same rings as the ring formed by connecting R ⁷¹⁷¹ and R ⁷²⁷² to each other. The ring formed by bonding R ¹⁰⁴ and R ¹⁰⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹¹¹ and R ¹¹² to each other include the same rings as the ring formed by connecting R ⁷¹⁷¹ and R ⁷²⁷² to each other. The ring formed by bonding R ¹¹¹ and R ¹¹² to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹¹⁴ and R ¹¹⁵ to each other include the same rings as the ring formed by connecting R ⁷¹ and R ⁷² to each other. The ring formed by bonding R ¹¹⁴ and R ¹¹⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting ^R121 and ^R122 to each other include the same rings as the ring formed by connecting ^R7171 and ^R7272 to each other. The ring formed by R ¹²¹ and R ¹²² being bonded to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the ring formed by connecting R ¹²⁴ and R ¹²⁵ to each other include the same rings as the ring formed by connecting R ⁷¹ and R ⁷² to each other. The ring formed by bonding R ¹²⁴ and R ¹²⁵ to each other is preferably formula (w-1) to formula (w-15), formula (w-17), formula (w-31), formula (w-32), formula (w-35) to the ring structure represented by formula (w-42) and formula (w-44), more preferably formula (w-1) to formula (w-6), formula (w-13), formula Ring structures represented by (w-35), formula (w-36), formula (w-42) and formula (w-44).

Examples of the divalent linking group represented by R ^x4 include an optionally substituted divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms or an optionally substituted divalent aliphatic hydrocarbon group having 6 to 18 carbon atoms. Aromatic hydrocarbon groups, etc. The -CH ₂ - contained in the above-mentioned divalent aliphatic hydrocarbon group and divalent aromatic hydrocarbon group may be replaced by -O-, -S-, -NR ^1B - (R ^1B represents a hydrogen atom or an alkane having 1 to 6 carbon atoms base), -CO-, -SO ₂ -, -SO-, -PO ₃ -substitution.

Moreover, a halogen atom, a hydroxyl group, a carboxyl group, an amino group etc. are mentioned as a substituent which the said divalent aliphatic hydrocarbon group and a divalent aromatic hydrocarbon group may have.

Specific examples of the divalent linking group represented by ^Rx4 include the same examples as specific examples of the divalent linking group represented by ^Rx1 .

The divalent linking group represented by R ^x4 is preferably a linking group described below.

Examples of the divalent linking group represented by R ^x5 include an optionally substituted trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms or an optionally substituted trivalent aliphatic hydrocarbon group having 6 to 18 carbon atoms. Aromatic hydrocarbon group. The -CH ₂ - contained in the above-mentioned trivalent aliphatic hydrocarbon group can be replaced by -O-, -S-, -CS-, -CO-, -SO-, -NR ^11B (R ^11B represents a hydrogen atom or a carbon number of 1 ~6 alkyl.)-substituted.

As a substituent which the said trivalent aliphatic hydrocarbon group and the said trivalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxyl group, an amino group etc. are mentioned.

The trivalent linking group represented by R ^x5 is preferably a trivalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent.

Specific examples of the trivalent linking group represented by ^Rx5 include the same examples as specific examples of the trivalent linking group represented by Rx2.

The linking group represented by R ^x5 is preferably a linking group described below.

Examples of the tetravalent linking group represented by R ^x6 include a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a tetravalent aliphatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Aromatic hydrocarbon group. The -CH ₂ - contained in the above-mentioned 4-valent aliphatic hydrocarbon group can be replaced by -O-, -S-, -CS-, -CO-, -SO-, -NR ^11C - (R ^11C represents the number of hydrogen atoms or carbon atoms 1 to 6 alkyl groups.) Substitution.

As a substituent which the said tetravalent aliphatic hydrocarbon group and the said tetravalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxyl group, an amino group etc. are mentioned.

The tetravalent linking groups represented by R ^x6 are each independently preferably a tetravalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent.

Specific examples of the tetravalent linking group represented by ^Rx6 include the same examples as specific examples of the tetravalent linking group represented by ^Rx3 .

The tetravalent linking group represented by R ^x6 is preferably a linking group described below.

Examples of the anion represented by the formula (V) include the anions described below.

Examples of the anion represented by the formula (VI) include the anions described below.

Examples of the anion represented by the formula (VII) include the anions described below.

<cation>

The compound of the present invention consists of an anion represented by formula (X) and a pair of cations. As long as the valence number of the anion represented by formula (X) is the same as that of the cation, the combination is not limited. When the valence of the anion shown in formula (X) is 2 or more, the cation may be a cation with the same valence as the anion shown in formula (X), or may be the same as the valence of the anion shown in formula (X). There are a plurality of monovalent cations having the same valence as the anion. Moreover, if it becomes the same valence number as the anion represented by formula (X), it may have a monovalent cation and a cation other than monovalent (for example, a divalent cation etc.). On the other hand, when the valence of the cation is 2 or more, it may have a plurality of monovalent anions represented by the formula (X) so as to have the same valence as the cation. Moreover, if it becomes the same valence number as a cation, you may have the anion represented by the formula (X) which is monovalent, and the anion represented by the formula (X) which is not monovalent.

The cation may be an organic cation or an inorganic cation. In addition, when the valence of the anion represented by the formula (X) is 2 or more, the compound (X) may have an organic cation and an inorganic cation as the cation.

Examples of organic cations include N-methylpyridinium, N-ethylpyridinium, N-propylpyridinium, N-ethyl-2-methylpyridinium, N-ethyl-3-methylpyridinium Onium, 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- Pyridinium cations such as 4,4'-bipyridinium;

Piperidinium cations such as 1-butyl-1-methylpiperidinium and 1-methyl-1-propylpiperidinium;

1-allyl-1-methylpyrrolidinium, 1-butyl-1-methylpyrrolidinium, 1-ethyl-1-methylpyrrolidinium, 1-methyl-1-propylpyrrole Alkylium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, 1-methyl-1-n-octylpyrrolidinium, 1-methyl-1-pentylpyrrolidinium, etc. Pyrrolidinium cation;

2-methyl-1-pyrrolinium and other cations with a pyrroline skeleton;

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 -Imidazolium cations such as 3-(4-sulfobutyl)imidazolium, 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium;

Amyl triethyl ammonium, butyl trimethyl ammonium, benzyl (ethyl) dimethyl ammonium, cyclohexyl trimethyl ammonium, diethyl (methyl) propyl ammonium, diethyl (2-methyl) ammonium Oxyethyl)methylammonium, ethyl(2-methoxyethyl)dimethylammonium, ethyl(dimethyl)(2-phenylethyl)ammonium, methyltri-n-octylammonium, Tetrabutylammonium, tetrahexylammonium, tetrapentylammonium, tetra-n-octylammonium, tetraheptylammonium, tetrapropylammonium, N, N, N, N', N', N'-hexamethyl-3 Ammonium cations such as -[2-(trimethylammonium)ethyl]-1,5-pentane diammonium;

Trimethylsulfonium, tributylsulfonium, triethylsulfonium and other trialkylsulfonium cations;

Tributyl hexadecyl phosphonium, tributyl methyl phosphonium, tributyl n-octyl phosphonium, tributyl n-octyl phosphonium, tetra-n-octyl phosphonium, tributyl (2-methoxyethyl) phosphonium, Phosphonium cations such as tributylmethylphosphonium, trihexyl (tetradecyl) phosphonium, trihexyl (tetradecyl) phosphonium;

Morpholinium cations such as 4-ethyl-4-methylmorpholinium;

Triarylmethane cations such as triphenylmethylium, etc.

Examples of inorganic cations include alkali metal ions such as lithium ions, sodium ions, potassium ions, rubidium ions, and cesium ions;

Monovalent metal ions such as copper (I) ions, silver ions, and iron (I) ions;

Beryllium ions, magnesium ions, calcium ions, strontium ions, barium ions and other alkaline earth metal ions;

Copper (II) ions, nickel ions, cobalt ions, iron (II) ions, manganese ions, palladium ions, zinc ions, germanium (IV) ions and other divalent metal ions;

Aluminum ions, cobalt (III) ions, iron (III) ions, chromium (III) ions, scandium ions, yttrium ions, ruthenium (III) ions, gallium ions, indium ions and other trivalent metal ions;

Tetravalent metal ions such as titanium ions, vanadium (IV) ions, zirconium ions, hafnium ions, germanium (IV) ions, and molybdenum (IV) ions;

NH ₄ ⁺ etc.

The cations are preferably alkali metal ions, alkaline earth metal ions, copper(I) ions, copper(II) ions, nickel ions, cobalt(III) ions, iron(II) ions, iron(III) ions, palladium ions and organic cations, Potassium ions, calcium ions, barium ions, magnesium ions, copper (I) ions, copper (II) ions, nickel ions, and organic cations are more preferred, and potassium ions and organic cations are still more preferred.

As a compound (X), the compound described in following Table 1-Table 9 is mentioned, for example. In addition, compound (1) is a compound shown below.

[Table 1]

[Table 2]

[table 3]

[Table 4]

[table 5]

[Table 6]

Compound (X) Anion (1) Cationic (1) Cationic (2) Anion (2) Compound (130) Formula (V-2) Potassium ion Potassium ion Compound (131) Formula (V-3) Potassium ion Potassium ion Compound (132) Formula (V-15) Potassium ion Potassium ion Compound (133) Formula (V-17) Potassium ion Potassium ion Compound (134) Formula (V-18) Potassium ion Potassium ion Compound (135) Formula (V-19) Potassium ion Potassium ion Compound (136) Formula (V-2) calcium ion Compound(137) Formula (V-3) Copper(II) ion Compound(138) Formula (V-18) Titanium ions Formula (V-18) Compound (139) Formula (V-18) Titanium ions Formula (V-19)

[Table 7]

Compound (X) Anion (1) Cationic (1) Cationic (2) Cationic (3) Compound(140) Formula (VI-2) Potassium ion Potassium ion Potassium ion Compound (141) Formula (VI-4) Potassium ion Potassium ion Potassium ion Compound 142) Formula (VI-8) Potassium ion Potassium ion Potassium ion Compound (143) Formula (VI-9) Potassium ion Potassium ion Potassium ion Compound(144) Formula (VI-22) Potassium ion Potassium ion Potassium ion

[Table 8]

[Table 9]

Compound (X) Anion (1) Cationic (1) Cationic (2) Anion (2) Compound(154) Formula (VIII-1) Potassium ion Potassium ion Compound (155) Formula (VIII-2) Potassium ion Potassium ion Compound (156) Formula (VIII-11) Potassium ion Potassium ion Compound(157) Formula (VIII-12) Potassium ion Potassium ion Compound (158) Formula (VIII-13) Potassium ion Potassium ion Compound(159) Formula (VII-20) Potassium ion Potassium ion Compound(160) Formula (VIII-21) Potassium ion Potassium ion Compound (161) Formula (VIII-1) Copper(II) ion Compound (162) Formula (VIII-2) Titanium ions Formula (VIII-2) Compound(163) Formula (VIII-11) N-Methylpyridinium N-Methylpyridinium

Compound (X) (hereinafter sometimes referred to as compound (I)) having an anion represented by formula (I) includes compound (1) to compound (63), etc., preferably compound (2), compound (3) , Compound (7)～Compound (11), Compound (13)～Compound (18), Compound (24), Compound (28), Compound (31), Compound (32), Compound (37), Compound (40) ~ Compound (44), Compound (46), Compound (47), Compound (49), Compound (50), Compound (55), Compound (58), Compound (60).

Compound (X) having an anion represented by formula (II) (hereinafter sometimes referred to as compound (II)) includes compound (64) to compound (92), etc., preferably compound (64), compound (65) , Compound (67), Compound (70), Compound (72), Compound (75)～Compound (77), Compound (79), Compound (80), Compound (83), Compound (84), Compound (86) , compound (87).

Compound (X) having an anion represented by formula (III) (hereinafter sometimes referred to as compound (III)) includes compound (93) to compound (118), etc., preferably compound (93), compound (94) , Compound (96), Compound (101) to Compound (105), Compound (107), Compound (109), Compound (111), Compound (115), Compound (116).

Compound (X) having an anion represented by formula (IV) (hereinafter sometimes referred to as compound (IV)) includes compound (119) to compound (129), and compound (125) is preferred.

Compound (X) having an anion represented by formula (V) (hereinafter sometimes referred to as compound (V)) includes compound (130) to compound (139), etc., preferably compound (130), compound (131) , compound (134), compound (135).

Compound (X) having an anion represented by formula (VI) (hereinafter sometimes referred to as compound (VI)) includes compound (140) to compound (144) and the like, preferably compound (140), compound (142) , Compound (144).

Compound (X) (hereinafter, sometimes referred to as compound (VII)) having an anion represented by formula (VII) includes compound (145) to compound (153) and the like.

Compound (X) (hereinafter, sometimes referred to as compound (VIII)) having an anion represented by formula (VIII) includes compound (154) to compound (163) and the like.

<Method for producing compound (I)>

Compound (I), for example, can be obtained by making a compound (hereinafter, sometimes referred to as compound (M-1)) shown in formula (M-1) and a compound shown in formula (M-2) (hereinafter, sometimes referred to as compound (M-2).) reaction to obtain.

[In formula (M-1), R ³ , R ⁴ and R ⁵ represent the same meanings as above, and ring W ^1A represents a ring structure.

In formula (M-2), R ¹ and R ² represent the same meanings as above. ]

The reaction of compound (M-1) with compound (M-2) is usually carried out by mixing compound (M-1) with compound (M-2), preferably adding compound to the mixture of base and compound (M-1) (M-2).

The reaction of compound (M-1) and compound (M-2) is preferably further carried out in the presence of a methylating agent,

More preferably, compound (M-2) is added to a mixture of compound (M-1), a methylating agent and a base.

Examples of the base include metal hydroxides (preferably alkali metal hydroxides) such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, calcium hydroxide, barium hydroxide, and magnesium hydroxide. ; sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide, potassium tert-butoxide and other metal alkoxides (preferably alkali metal alkoxides); lithium hydride, sodium hydride, potassium hydride, Lithium aluminum hydride, sodium borohydride, aluminum hydride, sodium aluminum hydride and other metal hydrides; calcium oxide, magnesium oxide and other metal oxides; sodium bicarbonate, sodium carbonate, potassium carbonate and other metal carbonates (preferably alkaline earth metal carbonates ); n-butyllithium, tert-butyllithium, methyllithium, Grignard reagent and other organoalkyl metal compounds; ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidine, piperidine, diazepine Bicycloundecene, diazabicyclononene, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, dimethoxyaniline, ammonium acetate, β-alanine and other amine compounds ( Preferred are tertiary amines such as triethylamine and diisopropylethylamine); amino metal compounds such as lithium diisopropylamide, sodium amide, and potassium hexamethyldisilazide (preferably alkali metal amino); trimethylhydrogen Sulfonium compounds such as sulfoxonium; iodonium compounds such as diphenyliodonium hydroxide; phosphazene bases, etc.

The usage-amount of a base is 0.1-10 mol normally with respect to 1 mol of compound (M-1), Preferably it is 0.5-5 mol.

Examples of the methylating agent include methyl iodide, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl p-toluenesulfonate, methyl trifluoromethanesulfonate, trimethyloxonium tetra Fluoborate, etc.

The usage-amount of a methylating agent is 0.1-10 mol normally with respect to 1 mol of compound (M-1), Preferably it is 0.5-5 mol.

The reaction of compound (M-1) and compound (M-2) can be performed in the presence of a solvent. Examples of solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, t-butanol, 2-butanone, tetrahydrofuran, diethyl ether , dimethylsulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, water, etc. Acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether are preferable, acetonitrile, tetrahydrofuran, and chloroform are more preferable, and acetonitrile is still more preferable.

In addition, the solvent is preferably a dehydration solvent.

The reaction time of compound (M-1) and compound (M-2) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.

The reaction temperature of compound (M-1) and compound (M-2) is usually -50 to 150°C, preferably -20 to 100°C.

The usage-amount of compound (M-2) is 0.1-10 mol normally with respect to 1 mol of compound (M-1), Preferably it is 0.5-5 mol.

Examples of the compound (M-1) include compounds described below and the like.

As a compound (M-2), a commercial item can be used, for example, malononitrile etc. are mentioned.

Compound (I) obtained by reacting compound (M-1) with compound (M-2) in the presence of a base usually has a cation derived from the base as a counter cation. When it is desired to exchange the cation of the compound (I) with a desired cation, ion exchange may 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. Salts having desired cations, for example, chloride salts containing desired cations and chloride ions, bromide salts containing desired cations and bromide ions, iodide salts containing desired cations and iodide ions , Fluoride salt containing the desired cation and fluoride ion, nitrate salt containing the desired cation and nitrate ion, sulfate salt containing the desired cation and sulfate ion, containing the desired cation and perchlorate ion perchlorate, sulfonate containing the desired cation and sulfonate ion, carboxylate containing the desired cation and carboxylate ion, hypochlorite containing the desired cation and hypochlorite ion, A hexafluorophosphate containing a desired cation and hexafluorophosphate, an imide salt containing a desired cation and an imide, and the like.

Compound (M-1) can be obtained by making a compound (hereinafter, sometimes referred to as compound (M-3) shown in formula (M-3).) and a compound (hereinafter, sometimes referred to as compound (M-3) shown in formula (M-4). Compound (M-4).) reaction to obtain.

[In formula (M-3), ring W ^1A , R ⁴ and R ⁵ have the same meanings as above.

In formula (M-4), R ³ represents the same meaning as above, and E ₁ represents a leaving group. ]

Examples of the leaving group represented by E1 include _a halogen atom, p-toluenesulfonyl group, trifluoromethanesulfonyl group and the like.

The reaction of compound (M-3) and compound (M-4) can be carried out by mixing compound (M-3) and compound (M-4).

The usage-amount of compound (M-4) is 0.1-5 mol normally with respect to 1 mol of compound (M-3), Preferably it is 0.5-2 mol.

The reaction of compound (M-3) and compound (M-4) is preferably performed in the presence of a base.

Examples of the base include metal alkoxides (preferably alkali metal alkoxides) such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide, and potassium tert-butoxide; lithium hydroxide , sodium hydroxide, potassium hydroxide and other metal hydroxides, sodium hydride, lithium aluminum hydride, sodium borohydride and other metal hydrides; lithium diisopropylamide, pyridine, triethylamine, diisopropylethylamine, piperazine Amine compounds such as pyridine, pyrrolidine, and proline.

The usage-amount of a base is 0.1-10 mol normally with respect to 1 mol of compound (M-3), Preferably it is 0.5-5 mol.

The reaction of compound (M-3) and compound (M-4) can be performed in the presence of a solvent. Examples of solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, t-butanol, 2-butanone, tetrahydrofuran, diethyl ether , dimethylsulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, water, etc. Preferred are acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether, more preferably acetonitrile, tetrahydrofuran, and chloroform, and still more preferably methanol, ethanol, isopropanol, and acetonitrile.

The reaction time of compound (M-3) and compound (M-4) is usually 0.1 to 10 hours.

The reaction temperature of the compound (M-3) and the compound (M-4) is usually -50 to 150°C.

Examples of the compound (M-3) include compounds described below and the like.

As the compound (M-4), a commercially available item can be used. Examples include cyanogen chloride, cyanogen bromide, p-toluenesulfonyl cyanide, trifluoromethanesulfonyl cyanide, 1-chloromethyl-4-fluoro-1,4-diazacation bicyclo[2.2.2]octane Bis(tetrafluoroborate) (also known as Selectfluor (registered trademark of Air Products and Chemicals)), benzoyl(phenyliodo)(trifluoromethanesulfonyl)methanate, 2,8-difluoro- 5-(Trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate, N-bromosuccinimide, N-chlorosuccinimide, N-iodo succinimide, etc.

Compound (M-3) can be obtained by reacting a compound represented by formula (M-5) (hereinafter, may be referred to as compound (M-5).) with compound (M-2a).

[In formula (M-5), ring W ^1A , R ⁴ and R ⁵ have the same meanings as above. ]

The reaction of compound (M-5) and compound (M-2a) can be carried out by mixing compound (M-5) and compound (M-2a).

The reaction of compound (M-5) and compound (M-2a) is preferably carried out in the presence of a base. Examples of the base include the same bases as those used in the reaction between the compound (M-1) and the compound (M-2). The use of the base is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (M-5).

The reaction of compound (M-5) and compound (M-2a) can be performed in the presence of a solvent. The solvent is preferably methanol, ethanol, isopropanol, toluene, acetonitrile.

The reaction time between compound (M-5) and compound (M-2a) is usually 0.1 to 10 hours.

The reaction temperature between compound (M-5) and compound (M-2a) is usually -50 to 150°C.

The usage-amount of compound (M-2a) is 0.1-10 mol normally with respect to 1 mol of compound (M-5), Preferably it is 0.5-2 mol.

As a compound (M-5), the compound etc. which are described below are mentioned.

In compound (I), when the combination of R ¹ and R ² is the same as the combination of R ⁴ and R ⁵ , compound (I) can also be obtained by making the compound shown in formula (M-6) (hereinafter, sometimes Referred to as compound (M-6).) and compound (M-2) reaction.

[In formula (M-6), ring W ^1A and R ³ have the same meanings as above. ]

The reaction of compound (M-6) and compound (M-2) can be carried out by mixing compound (M-6) and compound (M-2).

The reaction of compound (M-6) and compound (M-2) is preferably carried out in the presence of a base or a methylating agent, more preferably in the presence of a base and a methyl group.

The reaction of compound (M-6) and compound (M-2) is more preferably compound (M-6), compound (M-2), base and methylating agent are mixed,

It is further preferred to mix compound (M-2) and a base into a mixture of compound (M-6) and a methylating agent.

As the base used in the reaction between the compound (M-6) and the compound (M-2), the same base as the base used in the reaction between the compound (M-1) and the compound (M-2) can be mentioned, preferably a metal Carbonates, more preferably alkaline earth metal carbonates.

The usage-amount of a base is 0.1-5 mol normally with respect to 1 mol of compound (M-6), Preferably it is 0.5-2 mol.

Examples of the methylating agent used in the reaction between compound (M-6) and compound (M-2) include the same methylating agent used in the reaction between compound (M-1) and compound (M-2). The methylating agent is preferably dimethyl sulfate.

The usage-amount of a methylating agent is 0.1-5 mol normally with respect to 1 mol of compound (M-6), Preferably it is 0.5-2 mol.

The reaction of compound (M-6) and compound (M-2) can be performed in the presence of a solvent. Examples of solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, t-butanol, 2-butanone, tetrahydrofuran, diethyl ether , dimethylsulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, water, etc. Acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether are preferable, acetonitrile, tetrahydrofuran, and chloroform are more preferable, and acetonitrile is still more preferable.

In addition, the solvent is preferably a dehydration solvent.

The reaction time between compound (M-6) and compound (M-2) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.

The reaction temperature of compound (M-6) and compound (M-2) is usually -50 to 150°C, preferably -20 to 100°C.

The usage-amount of compound (M-2) is 0.1-10 mol normally with respect to 1 mol of compound (M-6), Preferably it is 0.5-5 mol.

Examples of the compound (M-6) include 2-methyl-1,3-cyclohexanedione and the like.

The molecular weight of the compound (X) is preferably 3000 or less, more preferably 2000 or less, still more preferably 1000 or less. In addition, it is preferably 50 or more, more preferably 100 or more, and still more preferably 200 or more.

Compound (X) preferably exhibits maximum absorption at a wavelength of 400 to 550 nm. The maximum absorption wavelength (λmax) of compound (X) is preferably a wavelength of 410 to 500 nm, more preferably a wavelength of 420 to 480 nm, and still more preferably a wavelength of 430 to 450 nm.

The molar absorption coefficient ε at the maximum absorption wavelength (λmax) is preferably 0.5 or more, more preferably 1.0 or more, particularly preferably 1.5 or more. The upper limit is not particularly limited, and is usually 10 or less.

When the molar absorption coefficient ε at λmax of the compound (X) is 0.5 or more, it is preferable from the viewpoint of efficiently absorbing light called blue light.

Compound (X) preferably satisfies the following formula (a).

ε(λ _max )/ε(λ _max +30nm)≥5 (a)

[In the formula, ε(λ _max ) represents the molar absorption coefficient at the maximum absorption wavelength (λ _max ).

ε(λ _max +30nm) represents the molar absorption coefficient at the wavelength of the maximum absorption wavelength (λ _max )+30nm.

It should be noted that the unit of the molar absorptivity is L/(g·cm). ]

ε(λmax)/ε(λmax+30nm) of the compound (X) is preferably 5 or more, more preferably 10 or more, particularly preferably 20 or more. The upper limit is not particularly limited, and is usually 1,000 or less.

When ε(λmax)/ε(λmax+30nm) is 5 or more, it is preferable from the viewpoint that only blue light can be selectively absorbed while suppressing the coloring of the composition containing compound (X) to a minimum. In particular, it is preferable because it can contribute to suppressing the influence of a display or the like on color display and expanding the color gamut.

<Composition Containing Compound (X)>

The present invention also includes a composition containing compound (X) (preferably any one of compound (I) to compound (VIII)).

The composition comprising compound (X) of the present invention (preferably any of compound (I) to compound (VIII)) preferably comprises any of compound (X) (preferably compound (I) to compound (VIII) species) and the resin composition of the resin.

The composition described above can be used for all purposes, among which it can be particularly suitable for applications where exposure to sunlight or light including ultraviolet rays is possible. Specific examples include glass substitutes and surface coating materials thereof; window glass, lighting glass, and light source protection glass for houses, facilities, and transportation equipment; coating materials for windows of houses, facilities, and transportation equipment, etc. film; interior and exterior decoration materials and paints for interior and exterior decoration of houses, facilities, transportation equipment, etc., and the coating film formed by the paint; alkyd resin paint and the paint film formed by the paint; acrylic paint and the paint film formed by the paint coating film; components for light sources emitting ultraviolet rays such as fluorescent lamps and mercury lamps; components for precision machinery, electronic and electrical equipment, and shielding materials for electromagnetic waves generated by various displays; containers or packaging for food, chemicals, pharmaceuticals, etc. Materials; bottles, boxes, blisters (Japanese: ブリスター), cups, special packaging, CD coatings, industrial and agricultural sheets or films; anti-fading agents for printed matter, dyed matter, dyes, pigments, etc.; polymer support Protective films for plastic parts such as machinery and automotive parts; printed outer coatings; inkjet media coatings; interlayer frosting; optical light films; safety glass/windshield interlayers; electrochromic/ Photochromic application; outer protective film; solar thermal control film; cosmetics such as sunscreen, shampoo, hair conditioner, and styling agent; fiber products and fibers for clothing such as sportswear, stockings, and hats; curtains, fleece Household interior products such as blankets and wallpapers; medical devices such as plastic lenses, contact lenses, and prosthetic eyes; optical products such as filters, backlight display films, prisms, mirrors, and photographic materials; mold films, transfer labels, anti-graffiti film, tape, ink and other stationery; signs, markers, etc. and their surface coating materials, etc.

The molded article formed by molding the above composition is preferably a polymer molded article. The shape of the molded product can be any shape such as flat film, powder, spherical particle, crushed particle, block continuous body, fiber, tube, hollow fiber, granular, plate, or porous.

When the above-mentioned composition is a resin composition, examples of the resin used in the resin composition include thermoplastic resins and thermosetting resins conventionally used in the production of various known molded articles, sheets, films, and the like.

Examples of thermoplastic resins include olefin resins such as polyethylene resins, polypropylene resins, and polycycloolefin resins; poly(meth)acrylate resins; polystyrene resins; styrene-acrylonitrile resins; acrylic resins; Nitrile-butadiene-styrene resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyvinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, Polyester resins such as ethylene-vinyl alcohol resins, polyethylene terephthalate resins, polybutylene terephthalate resins, liquid crystal polyester resins, polyacetal resins, polyamide resins, polycarbonate Ester resin, polyurethane resin and polyphenylene sulfide resin, etc. One or two or more of these resins may also be used in the form of a polymer blend or a polymer alloy.

Examples of the thermosetting resin include epoxy resins, melamine resins, unsaturated polyester resins, phenol resins, urea resins, alkyd resins, and thermosetting polyimide resins.

When the above-mentioned resin composition is used as an ultraviolet-absorbing color filter or an ultraviolet-absorbing film, the resin is preferably a transparent resin.

The said resin composition can be obtained by mixing compound (X) and resin. What is necessary is just to contain compound (X) in order to provide desired performance, for example, 0.00001-99 mass parts etc. can be contained with respect to 100 mass parts of resins.

The composition of the present invention may contain solvents, crosslinking catalysts, tackifiers, plasticizers, softeners, dyes, pigments, inorganic fillers and other additives as needed.

<Composition for spectacle lenses>

The above-mentioned composition and the above-mentioned resin composition may be compositions for spectacle lenses. Spectacle lenses can be formed by molding or the like using the composition for spectacle lenses. The molding method of the composition for spectacle lenses may be injection molding or injection polymerization molding. Injection polymerization molding refers to a method of injecting a spectacle lens composition mainly containing a monomer or oligomer resin into a lens mold, curing the spectacle lens composition with heat or light, and molding the spectacle lens into a lens.

The composition for spectacle lenses may have an appropriate composition according to the molding method thereof. For example, when forming a spectacle lens by injection molding, it may be a resin composition for spectacle lenses containing a resin and a compound (X). In addition, when forming a spectacle lens by injection polymerization molding, it may be a composition for spectacle lenses containing a curable monomer cured by heat or light and the compound (X).

Examples of the resin contained in the composition for spectacle lenses include the above-mentioned resins, and are preferably transparent resins. The resin contained in the composition for eyeglass lenses is preferably poly(meth)acrylate resin, polycarbonate resin, polyamide resin, polyurethane resin and polythioamino resin in the form of polymer blend or polymer alloy. One or more than two kinds of formate resins. In addition, not only polymers but also monomer components may be included.

The lens composition for eyeglasses may be a composition containing a curable monomer and a compound (X). The curable monomer may contain 2 or more types. Specifically, it may be a mixture of a polyol compound and an isocyanate compound, or a mixture of a thiol compound and an isocyanate compound, preferably a mixture of a thiol compound and an isocyanate, more preferably a mixture of a polyfunctional thiol compound and a polyfunctional isocyanate compound.

The thiol compound is not particularly limited as long as it has at least one thiol group in the molecule. It may be chain or ring. In addition, it may have a thioether bond, a polythioether bond, and other functional groups in the molecule. Examples of specific thiol compounds include aliphatic polythiol compounds, aromatic polythiol compounds, thiol group-containing cyclic compounds, thiol group-containing thioether compounds, etc. JP-A-2004-315556 A thiol group-containing organic compound having one or more thiol groups in one molecule described in . Among them, from the aspect of improving the refractive index and glass transition temperature of the lens, polyfunctional thiol compounds having two or more thiol groups are preferred, aliphatic polythiol compounds having two or more thiol groups are more preferred, and aliphatic polythiol compounds containing Thioether compounds with two or more thiol groups, more preferably bis(mercaptomethyl)sulfide, 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, pentaerythritol tetrathiopropionic acid ester, 4,8-dimercaptomethyl-1,11-mercapto-3,6,9-trithiaundecane. In addition, the above-mentioned thiol-based compounds may be used alone or in combination of two or more.

As the isocyanate compound, polyfunctional isocyanate compounds having at least two isocyanate groups (-NCO) in the molecule are preferable, and examples include aliphatic isocyanate-based compounds (such as hexamethylene diisocyanate, etc.), alicyclic isocyanate-based compounds (such as isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate), aromatic isocyanate compounds (such as toluene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, etc.), etc. In addition, polyol compound-based adducts (adducts) of the above-mentioned isocyanate compounds [for example, glycerin, trimethylolpropane-based adducts, etc.], isocyanurate products, biuret-type Compound, urethane prepolymer type isocyanate compound obtained by addition reaction with polyether polyol, polyester polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol, etc. and other derivatives.

When the lens composition for eyeglasses contains a curable monomer, in order to improve curability, a curing catalyst may be included. Examples of curing catalysts include tin compounds such as dibutyltin chloride, amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary Ionium salts, inorganic acids, Lewis acids, organic acids, silicic acids, tetrafluoroboric acids, peroxides, azo compounds, condensates of aldehydes and ammonia compounds, guanidines, thiourea Classes, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, acid phosphates, etc. These curing catalysts may be used alone or in combination of two or more.

The content of the compound (X) in the spectacle lens composition may contain, for example, 0.01 to 20 parts by mass with respect to 100 parts by mass of the resin when the composition for spectacle lenses is a resin composition. In addition, when the spectacle lens composition is a curable composition, for example, the content of the compound (X) may be 0.00001 to 20 parts by mass relative to 100 parts by mass of the curable component. The content of compound (X) is preferably 0.0001 to 15 parts by mass, more preferably 0.001 to 10 parts by mass, still more preferably 0.01 to 5 parts by mass, particularly preferably 0.1 to 3 parts by mass, based on 100 parts by mass of the resin or curable component.

The amount of the curing catalyst added is preferably 0.0001 to 10.0% by mass, more preferably 0.001 to 5.0% by mass, based on 100% by mass of the lens composition for eyeglasses.

The composition for spectacle lenses may contain other additives.

When using the composition of this invention for optical articles, such as an optical filter, it can apply to an optical display apparatus, for example. When the above-mentioned resin composition is applied to an optical display device, the layer formed by the above-mentioned resin composition may be any one of a film layer, an adhesive layer, a coating, etc., preferably an adhesive layer, a coating, etc. Floor.

<Adhesive composition>

In the case where the layer formed from the composition of the present invention is an adhesive layer, the adhesive layer is composed of an adhesive comprising resin (A), compound (X), crosslinking agent (B) and silane compound (C). Composition (Hereinafter, it may be referred to as an adhesive composition (i).) Formation. The adhesive composition (i) may further contain a radical curable component (D), an initiator (E), and a light-absorbing compound (F) other than the compound (X) (hereinafter sometimes referred to as a light-selective absorbing compound (F) ), antistatic agent, etc., preferably contain at least one selected from the group consisting of radical curable component (D), initiator (E) and photoselective absorption compound (F).

Resin (A) will not be specifically limited if it is resin used for an adhesive composition. The resin (A) preferably does not exhibit maximum absorption in the range of wavelength 300 nm to wavelength 780 nm.

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, particularly preferably 0°C or lower. The glass transition temperature of the resin (A) is usually -80°C or higher, preferably -70°C or higher, more preferably -60°C or higher, further preferably -55°C or higher, particularly preferably -50°C or higher. When the glass transition temperature of the resin (A) is 40° C. or lower, it is advantageous to improve the adhesiveness of the adhesive layer formed from the adhesive composition (i) to an adherend. Moreover, when the glass transition temperature of resin (A) is -80 degreeC or more, it contributes to improvement of the durability of the adhesive layer formed from adhesive composition (i). In addition, glass transition temperature can be measured with a differential scanning calorimeter (DSC).

Examples of the resin (A) include (meth)acrylic resins, silicone-based resins, rubber-based resins, and urethane-based resins, and are preferably (meth)acrylic resins.

The (meth)acrylic resin is preferably a polymer mainly composed of (meth)acrylate-derived structural units (preferably containing 50% by mass or more). The structural unit derived from (meth)acrylate may contain one or more structural units derived from monomers other than (meth)acrylate (for example, structural units derived from monomers having polar functional groups such as hydroxyl, carboxyl, and amino groups) .

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

Content of compound (X) is 0.01-20 mass parts normally with respect to 100 mass parts of resin (A), Preferably it is 0.1-20 mass parts, More preferably, it is 0.2-10 mass parts, Especially preferably, it is 0.5-5 mass parts.

Examples of the cross-linking agent (B) include isocyanate-based cross-linking agents, epoxy-based cross-linking agents, aziridine-based cross-linking agents, and metal chelate-based cross-linking agents. (i) From the viewpoint of the pot life, the durability of the pressure-sensitive adhesive layer, and the cross-linking speed, an isocyanate-based cross-linking agent is preferable.

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, and even more preferably 0.2 to 5 parts by mass relative to 100 parts by mass of the resin (A). , particularly preferably 0.25 to 2 parts by mass.

Examples of the silane compound (C) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyl Trimethoxysilane, 3-Glycidoxypropyltriethoxysilane, 3-Glycidoxypropylmethyldimethoxysilane, 3-Glycidoxypropylethoxydi Methylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methyl Acryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc.

The silane compound (C) may be a silicone oligomer.

The content of the silane compound (C) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, more preferably 0.15 to 7 parts by mass, and still more preferably 0.2 to 5 parts by mass, based on 100 parts by mass of the resin (A), Especially preferably, it is 0.25-2 mass parts.

Examples of the radical curable component (D) include radical curable components such as compounds and oligomers cured by radical polymerization.

As a radically polymerizable component (D), a (meth)acrylate type compound, a styrene type compound, a vinyl type compound, etc. are mentioned.

The adhesive composition (i) may contain two or more radical curable components (D).

Examples of (meth)acrylate compounds include (meth)acrylate monomers having at least one (meth)acryloyloxy group in the molecule, (meth)acrylamide monomers, and Compounds containing (meth)acryloyl groups such as (meth)acryloyl oligomers having at least two (meth)acryloyl groups in them. The (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. The (meth)acrylate-based compound may be used alone or in combination of two or more.

Examples of (meth)acrylate monomers include monofunctional (meth)acrylate monomers having one (meth)acryloyloxy group in the molecule, monofunctional (meth)acrylate monomers having two (meth)acryloxy groups in the molecule, Bifunctional (meth)acrylate monomers of acyloxy groups, polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule.

It is preferably a (meth)acrylate compound, more preferably a polyfunctional (meth)acrylate compound. It is preferable that a polyfunctional (meth)acrylate compound is trifunctional or more.

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, and still more preferably 5 to 30 parts by mass, based on 100 parts by mass of the resin (A). Parts by mass are particularly preferably 7.5 to 25 parts by mass.

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

Examples of thermal polymerization initiators include compounds that generate radicals by heating or the like (thermal radical generators), compounds that generate acids by heating or the like (thermal acid generators), compounds that generate bases by heating or the like (thermal base generators) agent), etc.

Examples of photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), And produce base compounds (photobase generators), etc.

The initiator (E) is preferably selected from an initiator suitable for the polymerization reaction of the radical curable component (D), more preferably a radical polymerization initiator, and even more preferably a photoradical polymerization initiator.

As a radical polymerization initiator, an alkylphenone compound, a benzoin compound, a benzophenone compound, an oxime ester compound, a phosphine compound, etc. are mentioned, for example. 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 type photoradical polymerization initiator, the reaction rate of a radical hardening component (D) can be raised even under the hardening conditions with weak illumination intensity or light intensity.

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, and still more preferably 0.75 to 4 parts by mass, relative to 100 parts by mass of the resin (A), Especially preferably, it is 1-3 mass parts.

The light selective absorption compound (F) is a light-absorbing compound other than the compound (X), for example, a compound (ultraviolet absorber) that absorbs light with a wavelength of 250 nm to a wavelength of 380 nm (preferably a wavelength of 250 nm or more and less than a wavelength of 360 nm), and an absorption wavelength of 380 nm. A compound (pigment) that absorbs light with a wavelength of 780 nm to 780 nm, and a compound that absorbs light with a wavelength of 780 nm to 1500 nm (infrared absorber).

The structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light with a wavelength of 250nm to 380nm. Preferred are benzotriazole-based compounds, benzophenone-based compounds, triazine-based compounds, salicylic acid-based compounds, and cyanide-based compounds. Compounds such as acrylate-based compounds, benzoxazine-based compounds, etc.

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, and still more preferably 1 to 25 parts by mass, based on 100 parts by mass of the resin (A). parts, particularly preferably 2 to 20 parts by mass.

The transmittance at a wavelength of 440 nm of the molded article molded from the composition containing compound (X) is preferably 50% or less, more preferably 30% or less.

Example

Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated more concretely, this invention is not limited to these examples. In the examples, % and parts indicating content or usage-amount are based on mass unless otherwise specified.

(Embodiment 1) Synthesis of the compound shown in formula (1)

Set a 100 mL four-necked flask equipped with a Dimrot condenser tube and a thermometer as a nitrogen atmosphere, add 2 parts of 2-methyl-1,3-cyclohexanedione, 1.3 parts of dimethyl sulfate, and 10 parts of acetonitrile, Heat to reflux and stir for 3 hours. 0.75 parts of malononitrile, 1.2 parts of potassium carbonate, and 10 parts of isopropanol were mixed with the obtained mixture, followed by heating under reflux for 3 hours and stirring. After distilling off the solvent from the obtained mixture, purification was performed to obtain 0.1 part of the compound represented by the formula (1).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (1) was produced.

¹ H-NMR: 1.70(m, 2H), 2.16(s, 3H), 2.50～2.62(m, 4H)

LC-MS; [M] ^- = 221.3

<Measurement of Maximum Absorption Wavelength and Molar Absorptivity ε>

The 2-butanone solution (0.006g/L) of the compound represented by the obtained formula (1) was added to a 1cm 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 at every 1 nm step by the double beam method. From the obtained absorbance value, the concentration of the compound represented by the formula (1) in the solution, and the optical path length of the quartz cell, the molar absorptivity for each wavelength was calculated.

ε(λ)=A(λ)/CL

[In the formula, ε (λ) represents the molar absorptivity (L/(g·cm)) of the compound shown in the formula (1) at the wavelength λ nm place, A (λ) represents the absorbance at the wavelength λ nm place, and C represents the concentration (g/L), L represents the optical path length (cm) of the quartz cell. 〕

The maximum absorption wavelength of the obtained compound represented by the formula (1) was 457 nm. The ε (λmax) of the compound shown in the obtained formula (1) is 150.6L/(g cm), ε (λmax+30nm) is 3.8L/(g cm), ε(λmax)/ε(λmax +30nm) was 39.6.

(Embodiment 2) Synthesis of the compound shown in formula (2)

Set a 300mL four-neck flask equipped with a Dimrot condenser tube and a thermometer as a nitrogen atmosphere, put 70 parts of dimedone, 10.4 parts of malononitrile, 40.6 parts of diisopropylethylamine, and 100 parts of ethanol, and heat to reflux Stirring was carried out for 3 hours. The solvent was distilled off from the obtained mixture, and purification was carried out to obtain 15.1 parts of the compound represented by the formula (M-5).

Under a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-5), 5.8 parts of p-toluenesulfonyl cyanide, 3 parts of potassium tert-butoxide and 50 parts of ethanol were mixed. The resulting mixture was stirred at a temperature of 0-5°C for 3 hours. The solvent was distilled off from the obtained mixture, followed by purification to obtain 3.3 parts of a compound represented by the formula (M-6).

Under a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-6), 7.7 parts of methyl triflate, 3.2 parts of potassium carbonate and 50 parts of methyl ethyl ketone were mixed. The resulting mixture was stirred at a temperature of 0-5°C for 3 hours. 4.6 parts of malononitrile and 13.0 parts of potassium carbonate were added to the obtained mixture, and it stirred at the temperature of 0-5 degreeC for 3 hours. The solvent was distilled off from the obtained mixture, followed by purification to obtain 3.1 parts of a compound represented by formula (2).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (2) was produced.

¹ H-NMR (deuterated DMSO) δ: 0.92(s, 6H), 2.45～2.52(s, 4H)

LC-MS; [M] ^- = 260.2

In addition, the maximum absorption wavelength and the molar absorptivity were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (2) was 432 nm. The ε (λmax) of the compound shown in the obtained formula (2) is 237L/(g cm), ε (λmax+30nm) is 4.4L/(g cm), ε(λmax)/ε(λmax+ 30nm) is 53.9.

(Example 3) Preparation of resin composition (1) (adhesive composition (1)) Polymerization example 1: Preparation of acrylic resin (A)

Into the reaction vessel equipped with condenser tube, nitrogen introduction tube, thermometer and stirrer, drop into the 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 solvent, The air in the reaction vessel was replaced with nitrogen to free from oxygen, and the inner temperature was raised to 55°C. Then, a solution obtained by dissolving 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added thereto. After adding the polymerization initiator, keep it at this temperature for 1 hour, and then keep the internal temperature at 54-56°C, while continuously adding ethyl acetate to the reaction vessel at an addition rate of 17.3 parts/hr. The addition of ethyl acetate was stopped when the concentration reached 35%, and the temperature was further kept at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The polystyrene conversion weight average molecular weight Mw by GPC of the obtained acrylic resin was 1.47 million, and Mw/Mn was 5.5. Let this be an acrylic resin (A).

<Preparation of resin composition (1)>

With respect to 100 parts of solid content of ethyl acetate solution (resin concentration: 20%) of acrylic resin (A), crosslinking agent (manufactured by Tosoh Corporation: trade name "Coronate L", isocyanate compound, solid content 75%) 0.3 parts, 0.28 parts of a silane compound (manufactured by Shin-Etsu Chemical Co., Ltd.: trade name "KBM3066"), and 1.5 parts of a compound represented by formula (2) were mixed, and ethyl acetate was further added so that the solid content concentration became 14%. ester to obtain a resin composition (1) (adhesive composition). In addition, the compounding quantity of the said crosslinking agent is the mass part which is an active ingredient.

(Examples 4-7 and Comparative Example 1) Production of Resin Compositions (2)-(6)

Except having changed each component and content of each component as shown in Table 10, it carried out similarly to Example 3, and produced the adhesive composition (2) - adhesive composition (6). In addition, the compounding quantity of a crosslinking agent is the mass part which is an active ingredient, and resin (A) is the mass part of a solid content.

[Table 10]

It should be noted that each abbreviation in Table 1 has the following meanings.

Acrylic resin (A): Acrylic resin (A) synthesized in Polymerization Example 1

Formula (2): the compound shown in the formula (2) synthesized in embodiment 2

Coronate L: manufactured by Tosoh Corporation, brand name: Coronate L, isocyanate-based crosslinking agent

KBM3066: Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, silane coupling agent

A-DPH-12E: manufactured by Shin-Nakamura Chemical Industry Co., Ltd., brand name; A-DPH-12E, hexafunctional (meth)acrylate compound

NCI-730: manufactured by ADEKA Co., Ltd., trade name: NCI-730, photoradical generator as an oxime ester compound

RUVA-93: Otsuka Chemical Co., Ltd., benzotriazole-based ultraviolet absorber, brand name: RUVA-93, maximum absorption wavelength λmax=337 nm

C.I.Y33: Sumiplast Lemon Yellow HL (C.I. Solvent Yellow 33, manufactured by Sumika Chemtex Co., Ltd.)

<Evaluation of molded article of resin composition (1)>

〔Production of resin molding (1)〕

Using an applicator, apply the obtained resin composition (1) to a separator formed of a polyethylene terephthalate film subjected to mold release treatment [trade name "PLR-382190" obtained from LINTEC Corporation] ], and dried at a temperature of 100 for 1 minute to produce a resin molded body (adhesive layer) (1). The obtained resin molded body (1) had a thickness of 15 μm.

After laminating the obtained resin molded body (1) to a cycloolefin film containing an ultraviolet absorber with a thickness of 23 μm [trade name "ZEONOR" obtained from Japan ZEON Co., Ltd.], the temperature was 23 ° C, relatively Aging was carried out for 7 days at a humidity of 65% to obtain a laminate (1) of cycloolefin film/resin molded article (1)/separator.

[Measurement of Absorbance of Resin Molded Article (1)]

The obtained laminated body (1) was cut into a size of 30 mm × 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 Incorporated], which was used as Sample (1). Using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation), the absorbance of the prepared sample (1) in a wavelength range of 300 to 800 nm was measured in steps of 1 nm. The measured absorbance at a wavelength of 440 nm was defined as the absorbance at a wavelength of 440 nm of the resin molded article (1). The results are shown in Table 11. It should be noted that the absorbance of each of the alkali-free glass monomer and the cycloolefin film monomer at a wavelength of 330 nm and a wavelength of 440 nm is zero.

In addition, the transmittances at a wavelength of 440 nm and a wavelength of 330 nm were obtained based on the following equations. The results are shown in the T440 column of Table 11 as the transmittance at a wavelength of 440 nm, and in the T330 nm column as the wavelength of 330 nm.

T=10 ^-A ×100 (T means transmittance, A means absorbance.)

[Measurement of Absorbance Retention of Resin Molded Article (1)]

The sample (1) after the absorbance measurement was placed in a sunlight weather resistance tester (manufactured by Suga Test Instruments Co., Ltd.) under the conditions of a temperature of 63° C. and a relative humidity of 50% RH for 75 hours to implement a weather resistance test. The absorbance of the sample (1) taken out was measured by the same method as above. From the measured absorbance, the absorbance retention rate of the sample at a wavelength of 440 nm was calculated based on the following formula. In the following formula, A(440) represents the absorbance at a wavelength of 440 nm. The results are shown in Table 11. The closer the absorbance retention is to 100, the less the light selective absorption function is degraded, and the material has good weather resistance.

Absorbance retention (%)

=(A(440) after the durability test/A(440) before the durability test)×100

[Evaluation of bleeding resistance of resin molded article (1)]

A separator was further laminated on one side of the obtained resin molded body (1) to obtain a resin molded body (1) with separators on both sides. The obtained resin molded article (1) with separators on both sides was stored in air at a temperature of 23 to 25° C. for one month. The presence or absence of crystallization of the compound in the surface of the stored resin molded article (1) with separators on both surfaces was confirmed using a microscope. The case where no crystals precipitated was set to a, and the case where crystals were precipitated was set to b. The evaluation results are shown in the column of bleeding resistance in Table 11.

Using the resin composition (2) instead of the resin composition (1), a resin molded body (2), a laminate (2) and a resin molded body (2) with separators on both sides were prepared and evaluated in the same manner. The results are shown in Table 11.

Using the resin composition (3) instead of the resin composition (1), a resin molded body (3), a laminate (3) and a resin molded body (3) with separators on both sides were prepared and evaluated in the same manner. The results are shown in Table 11.

Using the resin composition (6) instead of the resin composition (1), a resin molded body (6), a laminate (6) and a resin molded body (6) with separators on both sides were prepared and evaluated in the same manner. The results are shown in Table 11.

<Evaluation of molded article of resin composition (4)>

〔Production of resin molded body (4)〕

Using an applicator, apply the resin composition (4) to a separator formed of a polyethylene terephthalate film that has been subjected to a release treatment so that the thickness after drying becomes 5 μm [commercial product obtained from LINTEC Corporation] Name "PLR-382190"], the release treatment surface was dried at a temperature of 100°C for 1 minute. Then, UV-A (wavelength 320 to 390 nm) was adjusted to an illuminance of 500 mW and a cumulative light intensity of 500 mJ using an ultraviolet irradiation device ("electrodeless UV lamp system H bulb" manufactured by Fusion UV Systems Co., Ltd.) from the diaphragm side, and ultraviolet irradiation was performed, thereby A resin molded body (adhesive layer) (4) is produced.

The obtained resin molded body (4) was bonded to the non-alkali glass, and after the separator was peeled off, a 23 μm cycloolefin film containing an ultraviolet absorber was bonded on the resin molded body (4) [commercial product obtained from Japan ZEON Corporation]. Named "ZEONOR"], a laminate (4) having a composition of cycloolefin film/resin molded body (4)/glass was produced.

[Measurement of Absorbance of Resin Molded Article (4)]

The produced laminate (4) was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured in a wavelength range of 300 to 800 nm in steps of 1 nm by a two-beam method. The measured absorbance at a wavelength of 440 nm was defined as the absorbance at a wavelength of 440 nm of the resin molded article (4). It should be noted that the absorbance of each of the alkali-free glass monomer and the cycloolefin film monomer at a wavelength of 330 nm and a wavelength of 440 nm is zero.

In addition, the transmittances at a wavelength of 440 nm and a wavelength of 330 nm were obtained based on the following equations. The results are shown in the T440 column of Table 11 as the transmittance at a wavelength of 440 nm, and in the T330 nm column as the wavelength of 330 nm.

T=10 ^-A ×100 (T means transmittance, A means absorbance.)

[Measurement of Absorbance Retention of Resin Molded Article (4)]

The laminate (4) after the absorbance measurement was placed 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 to implement a weather resistance test. The absorbance of the resin molded body ( 4 ) of the taken out laminate ( 4 ) was measured by the same method as above. From the measured absorbance, the absorbance retention rate of the sample at a wavelength of 440 nm was calculated based on the following formula. In the following formula, A(440) represents the absorbance at a wavelength of 440 nm. The results are shown in Table 11. The closer the absorbance retention is to 100, the less the light selective absorption function is degraded, and the material has good weather resistance.

Absorbance retention (%)

=(A(440) after the durability test/A(440) before the durability test)×100

[Evaluation of bleeding resistance of resin molded article (4)]

A separator was further laminated on one surface of the obtained resin molded body (4) to obtain a resin molded body (4) with separators on both sides. The obtained resin molded article (4) with separators on both sides was stored in air at a temperature of 23 to 25° C. for one month. The presence or absence of crystallization of the compound in the surface of the stored resin molded article (4) with separators on both surfaces was confirmed using a microscope. The case where no crystals precipitated was set to a, and the case where crystals were precipitated was set to b. The evaluation results are shown in the column of bleeding resistance in Table 11.

Using the resin composition (5) instead of the resin composition (4), a resin molded body (5), a laminate (5) and a resin molded body (5) with separators on both sides were prepared and evaluated in the same manner. The results are shown in Table 11.

[Table 11]

(Example 8) Preparation of resin composition for spectacle lens and molded body thereof

With 40 parts of xylylene diisocyanate, 60 parts of trimethylolpropane three (thioglycolic acid esters), 0.01 part of compound shown in the formula (2) synthesized in the embodiment 2, release agent (trade name : ZELEC-UN, obtained from Sigma-Aldrich) 0.2 parts, and 0.03 parts of dibutyltin dichloride as a curing catalyst were mixed and stirred. The obtained mixture was left to stand in a vacuum drier for 1 hour to degas. The resulting mixture was poured into a glass mold and heated at a temperature of 120° C. for 1 hour. Only the molded body was peeled off from the glass mold, and a resin plate having a thickness of 2 mm and 3 cm×3 cm was produced as a molded body.

(Examples 9-12) Preparation of the resin composition for spectacle lenses and its molded body

Except having changed content of the compound represented by formula (2) into content [part] shown in Table 12, it carried out similarly to Example 8, and obtained the resin composition for spectacle lenses, and the resin plate which is the molded object.

[Table 12]

<Evaluation of resin board>

[Measurement of absorbance of resin plate]

Using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation), the absorbance in the wavelength range of 300 to 800 nm of the resin plate obtained above was measured every 1 nm step.

In addition, the transmittance at a wavelength of 440 nm was obtained based on the following formula. The results are shown in the T440 column of Table 13.

T=10 ^-A ×100 (T means transmittance, A means absorbance.)

[Measurement of Absorbance Retention of Resin Plate]

The resin plate after the absorbance measurement was placed 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 to implement a weather resistance test. The absorbance of the taken-out resin plate was measured by the same method as above. From the measured absorbance, the absorbance retention rate of the resin plate at a wavelength of 440 nm was calculated based on the following formula. In the following formula, A(440) represents the absorbance at a wavelength of 440 nm. The results are shown in Table 13. The closer the absorbance retention is to 100, the less the light selective absorption function is degraded, and the material has good weather resistance.

Absorbance retention (%)

=(A(440) after the durability test/A(440) before the durability test)×100

[Table 13]

T440 Absorbance retention Example 8 0.048 93.3 Example 9 1.4 85.1 Example 10 14 81.9 Example 11 14.9 81 Example 12 30 78.9

(Examples 13-15) Preparation of resin compositions (7)-(9) (adhesive compositions (7)-(9))

Polymerization example 2: Preparation of acrylic resin (A1)

81.8 parts of ethyl acetate, 70 parts of butyl acrylate, 1 part of 2-hydroxyethyl methyl acrylate, 1 part of acrylic acid, phenoxy A mixed solution of 8 parts of methyl ethyl ester and 0.5 parts of butoxymethacrylamide was used to replace the air in the reaction vessel with nitrogen to make it free of oxygen, and at the same time, the inner temperature was raised to 55°C. Then, a solution obtained by dissolving 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added thereto. After adding the polymerization initiator, keep it at this temperature for 1 hour, then keep the internal temperature at 54-56°C, and continuously add ethyl acetate to the reaction vessel at an addition rate of 17.3 parts/hr. The addition of ethyl acetate was stopped when it reached 35%, and the temperature was further kept at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The polystyrene conversion weight average molecular weight Mw by GPC of the obtained acrylic resin was 1.25 million, and Mw/Mn was 4.5. Let this be an acrylic resin (A1).

Except having changed each component and content of each component as shown in Table 14, it carried out similarly to Example 3, and produced the adhesive composition (7) - adhesive composition (9). In addition, the compounding quantity of a crosslinking agent is the mass part which is an active ingredient, and resin (A) is the mass part of a solid content.

[Table 14]

It should be noted that each abbreviation in Table 14 has the following meanings.

Acrylic resin (A1): Acrylic resin (A1) synthesized in Polymerization Example 2

Formula (2): the compound shown in the formula (2) synthesized in embodiment 2

Coronate L: manufactured by Tosoh Corporation, brand name: Coronate L, isocyanate-based crosslinking agent

KBM3066: Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, silane coupling agent

KBM403: Shin-Etsu Chemical Co., Ltd., trade name: KBM403, silane coupling agent

M-130G: manufactured by Shin-Nakamura Chemical Industry Co., Ltd., brand name: M-130G, monofunctional methoxy polyethylene glycol methacrylate

Ionic compound: an ionic compound represented by the following formula

<Evaluation of molded article of resin composition (7)>

〔Production of resin molding (7)〕

Using an applicator, apply the obtained resin composition (7) to a separator formed of a polyethylene terephthalate film subjected to mold release treatment [trade name "PLR-382190" obtained from LINTEC Corporation] ], and dried at a temperature of 100° C. for 1 minute to produce a resin molded body (adhesive layer) (7). The obtained resin molded body ( 7 ) had a thickness of 20 μm.

After laminating the obtained resin molded body (7) to a cycloolefin film containing an ultraviolet absorber with a thickness of 23 μm [trade name “ZEONOR” obtained from Japan ZEON Co., Ltd.], the resulting resin molded body (7) was heated at a temperature of 23° C. Aging was carried out for 7 days at a humidity of 65%, to obtain a laminate (7) of cycloolefin film/resin molded article (7)/separator.

[Measurement of Absorbance of Resin Molded Article (7)]

The obtained laminated body (7) was cut into a size of 30 mm × 30 mm, the separator was peeled off, and the resin molded body (7) was bonded to an alkali-free glass [trade name "EAGLE XG" manufactured by Corning Incorporated], which was used as Sample (7). Using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation), the absorbance of the prepared sample (7) in a wavelength range of 300 to 800 nm was measured in steps of 1 nm. The measured absorbance at a wavelength of 440 nm was defined as the absorbance at a wavelength of 440 nm of the resin molded article (7). The results are shown in Table 15. It should be noted that the absorbance of each of the alkali-free glass monomer and the cycloolefin film monomer at a wavelength of 330 nm and a wavelength of 440 nm is zero.

In addition, the transmittances at a wavelength of 440 nm and a wavelength of 330 nm were obtained based on the following equations. The results are shown in the T440 column of Table 15 for the transmittance at a wavelength of 440 nm, and in the T330 nm column for a wavelength of 330 nm.

T=10 ^-A ×100 (T means transmittance, A means absorbance.)

[Measurement of Absorbance Retention of Resin Molded Article (7)]

The sample (7) after the absorbance measurement was placed 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 to implement a weather resistance test. The absorbance of the sample (7) taken out was measured by the same method as above. From the measured absorbance, the absorbance retention rate of the sample at a wavelength of 440 nm was calculated based on the following formula. In the following formula, A(440) represents the absorbance at a wavelength of 440 nm. The results are shown in Table 15. The closer the absorbance retention is to 100, the less the light selective absorption function is degraded and the weather resistance is good.

Absorbance retention (%)

=(A(440) after the durability test/A(440) before the durability test)×100

[Evaluation of bleeding resistance of resin molded article (7)]

A separator was further laminated on one side of the obtained resin molded body ( 7 ) to obtain a resin molded body ( 7 ) with separators on both sides. The obtained resin molded body (7) with separators on both sides was stored in the air at 23 to 25° C. for one month. Presence or absence of precipitation of compound crystals in the surfaces of the stored resin molded article ( 7 ) with separators on both surfaces was confirmed using a microscope. The case where no crystals precipitated was set to a, and the case where crystals were precipitated was set to b. The evaluation results are shown in the column of bleeding resistance in Table 15.

Using resin composition (8) instead of resin composition (7), resin molded body (8), laminated body (8), and resin molded body (7) with separators on both sides were prepared and evaluated in the same manner. The results are shown in Table 15.

Using the resin composition (9) instead of the resin composition (7), a resin molded body (9), a laminate (9) and a resin molded body (9) with separators on both sides were prepared and evaluated in the same manner. The results are shown in Table 15.

[Table 15]

The compound of the present invention has high absorption selectivity to short-wavelength visible light with a wavelength of 440 nm. In addition, the resin composition containing the compound of the present invention also has a high absorbance retention rate after the weather resistance test, and has good weather resistance.

Claims (12)

1. A compound comprising an anion having a partial structure represented by formula (X),

in the formula (X), ring W ¹ Represents a ring structure having at least one substituent.

2. The compound according to claim 1, wherein the anion having a partial structure represented by formula (X) is any one of an anion represented by formula (I) to an anion represented by formula (VIII),

in the formula, ring W ¹ Are meant to have the same meaning as above,

ring W ² Ring W ³ Ring W ⁴ Ring W ⁵ Ring W ⁶ Ring W ⁷ Ring W ⁸ Ring W ⁹ Ring W ¹⁰ Ring W ¹¹ Ring W ¹² Ring W ¹³ And a ring W ¹⁴ Each independently represents a ring structure optionally having a substituent,

R ¹ 、R ² 、R ⁴ 、R ⁵ 、R ¹² 、R ¹⁴ 、R ¹⁵ 、R ²² 、R ²⁴ 、R ²⁵ 、R ³² 、R ³⁴ 、R ³⁵ 、R ⁴² 、R ⁴⁴ 、R ⁴⁵ 、R ⁵² 、R ⁵⁴ 、R ⁵⁵ 、R ⁶² 、R ⁶⁴ 、R ⁶⁵ 、R ⁷¹ 、R ⁷² 、R ⁷⁴ 、R ⁷⁵ 、R ⁸¹ 、R ⁸² 、R ⁸⁴ 、R ⁸⁵ 、R ⁹¹ 、R ⁹² 、R ⁹⁴ 、R ⁹⁵ 、R ¹⁰¹ 、R ¹⁰² 、R ¹⁰⁴ 、R ¹⁰⁵ 、R ¹¹¹ 、R ¹¹² 、R ¹¹⁴ 、R ¹¹⁵ 、R ¹²¹ 、R ¹²² 、R ¹²⁴ 、R ¹²⁵ 、R ¹³¹ 、R ¹³² 、R ¹³⁴ and R ¹³⁵ Each independently represents an electron-withdrawing group,

R ³ represents a substituent having a valence of 1,

R ¹³ 、R ²³ 、R ³³ 、R ⁴³ 、R ⁵³ 、R ⁶³ and R ¹³³ Represents a substituent having a valence of 1,

R ¹ and R ² Optionally linked to each other to form a ring,

R ² and R ³ Optionally linked to each other to form a ring,

R ³ and R ⁴ Optionally linked to each other to form a ring,

R ⁴ and R ⁵ Optionally linked to each other to form a ring,

R ¹² and R ¹³ Optionally linked to each other to form a ring,

R ¹³ and R ¹⁴ Optionally linked to each other to form a ring,

R ¹⁴ and R ¹⁵ Optionally linked to each other to form a ring,

R ²² and R ²³ Optionally linked to each other to form a ring,

R ²³ and R ²⁴ Optionally linked to each other to form a ring,

R ²⁴ and R ²⁵ Optionally linked to each other to form a ring,

R ³² and R ³³ Optionally linked to each other to form a ring,

R ³³ and R ³⁴ Optionally linked to each other to form a ring,

R ³⁴ and R ³⁵ Optionally linked to each other to form a ring,

R ⁴² and R ⁴³ Optionally linked to each other to form a ring,

R ⁴³ and R ⁴⁴ Optionally linked to each other to form a ring,

R ⁴⁴ and R ⁴⁵ Optionally linked to each other to form a ring,

R ⁵² and R ⁵³ Optionally linked to each other to form a ring,

R ⁵³ and R ⁵⁴ Optionally linked to each other to form a ring,

R ⁵⁴ and R ⁵⁵ Optionally linked to each other to form a ring,

R ⁶² and R ⁶³ Optionally to each otherAre connected to form a ring,

R ⁶³ and R ⁶⁴ Optionally linked to each other to form a ring,

R ⁶⁴ and R ⁶⁵ Optionally linked to each other to form a ring,

R ⁷¹ and R ⁷² Optionally linked to each other to form a ring,

R ⁷⁴ and R ⁷⁵ Optionally linked to each other to form a ring,

R ⁸¹ and R ⁸² Optionally linked to each other to form a ring,

R ⁸⁴ and R ⁸⁵ Optionally linked to each other to form a ring,

R ⁹¹ and R ⁹² Optionally linked to each other to form a ring,

R ⁹⁴ and R ⁹⁵ Optionally linked to each other to form a ring,

R ¹⁰¹ and R ¹⁰² Optionally linked to each other to form a ring,

R ¹⁰⁴ and R ¹⁰⁵ Optionally linked to each other to form a ring,

R ¹¹¹ and R ¹¹² Optionally linked to each other to form a ring,

R ¹¹⁴ and R ¹¹⁵ Optionally linked to each other to form a ring,

R ¹²¹ and R ¹²² Optionally linked to each other to form a ring,

R ¹²⁴ and R ¹²⁵ Optionally linked to each other to form a ring,

R ¹³¹ and R ¹³² Optionally linked to each other to form a ring,

R ¹³² and R ¹³³ Optionally linked to each other to form a ring,

R ¹³³ and R ¹³⁴ Optionally linked to each other to form a ring,

R ¹³⁴ and R ¹³⁵ Optionally linked to each other to form a ring,

R ^x1 、R ^x4 and R ^x7 Each independently represents a single bond or a 2-valent linking group,

R ^x2 and R ^x5 Each independently represents a linking group having a valence of 3,

R ^x3 and R ^x6 Each independently represents a linking group having a valence of 4.

3. The compound of claim 2, wherein R ³ Is an electron-withdrawing group.

4. A compound according to claim 2 or 3, wherein R is selected from ¹ 、R ² 、R ³ 、R ⁴ And R ⁵ At least one of which is cyano, nitro, haloalkyl, haloaryl, -CO-R ₁ 、-CO-O-R ₂ 、-CO-NR ₃ R _3k 、-CO-S-R ₄ 、-CS-R ₅ 、-CS-O-R ₆ 、-CS-S-R ₇ 、-SO-R ₈ 、-SO ₂ -R ₉ 、-OCF ₃ 、-SCF ₃ 、-SF ₅ 、-SF ₃ 、-SO ₂ H or-SO ₃ H，

Wherein R is ₁ 、R ₂ 、R ₃ 、R _3k 、R ₄ 、R ₅ 、R ₆ 、R ₇ 、R ₈ And R ₉ Each independently represents a hydrocarbon group optionally having a substituent or a halogen atom.

5. A compound according to any one of claims 2 to 4, selected from R ¹ 、R ² 、R ³ 、R ⁴ And R ⁵ At least one of which is cyano, nitro, -CO-R ₁ 、-CO-O-R ₂ 、-SO ₂ -R ₉ 、-SF ₅ 、-SF ₃ 、-SO ₃ H、-SO ₂ H、-OCF ₃ or-SCF ₃ ，

Wherein R is ₁ 、R ₂ And R ₉ Each independently represents a hydrocarbon group optionally having a substituent or a halogen atom.

6. A compound according to any one of claims 2 to 5, selected from R ¹ 、R ² 、R ³ 、R ⁴ And R ⁵ At least one of which is cyanogenA group or a nitro group.

7. The compound according to any one of claims 1 to 6, which exhibits an absorption maximum between a wavelength of 400nm and a wavelength of 550 nm.

8. The compound according to any one of claims 1 to 7, which has an molar absorption coefficient at the maximum absorption wavelength of 0.5 or more.

9. The compound according to any one of claims 1 to 8, which satisfies the following formula (a),

ε(λ _max )/ε(λ _max +30nm)≥5 (a)

in the formula,. Epsilon. (λ max) represents the maximum absorption wavelength λ _max The molar absorptivity of (a) ∈ (epsilon) (. Lambda.) _max +30 nm) represents the maximum absorption wavelength λ _max Molar absorptivity at a wavelength of +30nm,

the molar absorption coefficient is expressed in units of L/(g · cm).

10. A composition comprising a compound of any one of claims 1-9.

11. A molded article obtained by molding the composition according to claim 10.

12. The molded article according to claim 11, having a transmittance at a wavelength of 440nm of 50% or less.