JP2023013166A - Compound - Google Patents

Abstract

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

Description

The present invention relates to compounds.

Dye compounds that absorb visible light are used in textiles, inks, paints, containers, packaging materials, printed matter, optical goods, eyeglasses, display devices, etc., for the purpose of coloring objects and transmitting or absorbing light of specific wavelengths. Used for a wide range of purposes. Important properties of dye compounds include selective absorption (sharpness of absorption spectrum) and durability (especially weatherability). Among dye compounds, cyanine dyes can control a wide range of wavelengths exhibiting maximum absorption from the ultraviolet region with a wavelength of 380 nm or less to the near-infrared region with a wavelength of 780 nm or more by controlling the number of methine carbon atoms in the polymethine skeleton. Many of the cyanine dyes have been widely used because they exhibit relatively high selective absorption (for example, Patent Document 1).

U.S. Pat. No. 6,004,536

However, although cyanine dyes have high selective absorbability, many of them are inferior in durability (especially weather resistance), and compounds with good durability have been desired.

［式（Ｉ）中、
環Ｗ^１及び環Ｗ^２は、それぞれ独立して、少なくとも１つの二重結合を環の構成要素として有する環構造を表す。
環Ｗ^１及び環Ｗ^２は、それぞれ独立して、置換基を有していてもよい。
Ｒ^１及びＲ^２は、それぞれ独立して、水素原子又は１価の置換基を表し、Ｒ^１及びＲ^２の少なくとも一方は１価の置換基である。］
［２］ Ｒ^１及びＲ^２から選ばれる少なくとも１つが、電子求引性基である［１］に記載の化合物。
［３］ Ｒ^１及びＲ^２から選ばれる少なくとも１つが、シアノ基、ニトロ基、ハロゲン化アルキル基、ハロゲン化アリール基、－ＣＯ－Ｒ_１、－ＣＯ－Ｏ－Ｒ_２、－ＣＯ－ＮＲ_３Ｒ_３ｋ、－ＣＯ－Ｓ－Ｒ_４、－ＣＳ－Ｒ_５、－ＣＳ－Ｏ－Ｒ_６、－ＣＳ－Ｓ－Ｒ_７、－ＳＯ－Ｒ_８、－ＳＯ_２－Ｒ_９（Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_３ｋ、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８及びＲ_９はそれぞれ独立して、置換基を有していてもよい炭化水素基又はハロゲン原子を表す。）、－ＯＣＦ_３、－ＳＣＦ_３、－ＳＦ_５、－ＳＦ_３、－ＳＯ_２Ｈ又は－ＳＯ_３Ｈである［２］に記載の化合物。
［４］ Ｒ^１及びＲ^２から選ばれる少なくとも１つが、シアノ基である［３］に記載の化合物。
［５］ 式（Ｉ）で表される部分構造を含むカチオンが、式（Ｉ－Ａ）で表されるカチオンである［１］～［４］のいずれかに記載の化合物。

［式（Ｉ－Ａ）中、
環Ｗ^１、環Ｗ^２、Ｒ^１及びＲ^２は、それぞれ上記と同じ意味を表す。
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立して、水素原子、複素環基、置換基を有していてもよい炭素数１～２４の炭化水素基を表し、該炭化水素基に含まれる－ＣＨ_２－又は＝ＣＨ－は、－Ｏ－又は－Ｓ－に置換されていてもよい。
Ｒ^３及びＲ^４は互いに連結して環を形成してもよい。
Ｒ^５及びＲ^６は互いに連結して環を形成してもよい。］
［６］ 式（Ｉ－Ａ）で表されるカチオンが、式（Ｉ－Ｂ）で表されるカチオン又は式（Ｉ－Ｃ）で表されるカチオンである［５］に記載の化合物。

［式（Ｉ－Ｂ）及び式（Ｉ－Ｃ）中、
環Ｗ^１、環Ｗ^２、Ｒ^１及びＲ^２は、それぞれ上記と同じ意味を表す。
Ａｒ^１及びＡｒ^２は、それぞれ独立して、置換基を有していてもよい炭素数６～２４の芳香族炭化水素基を表す。
Ｒ^４Ａ及びＲ^６Ａは、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数６～２４の炭化水素基を表す。
環Ｗ^３及び環Ｗ^４は、それぞれ独立して、含窒素複素環基を表す。］
［７］ 波長４００ｎｍ～波長７００ｎｍの間に極大吸収を示す［１］～［６］のいずれかに記載の化合物。
［８］ ［１］～［７］のいずれかに記載の化合物と樹脂とを含む樹脂組成物。
［９］ ［１］～［７］のいずれかに記載の化合物と重合性モノマーとを含む組成物。
［１０］ ［８］又は［９］に記載の組成物から成形される成形体。
［１１］ ［１］～［７］のいずれかに記載の化合物によって染色された染色物。
［１２］ 下記式（Ｉ）で表される部分構造を含むカチオンを含む光学層。

［式（Ｉ）中、
環Ｗ^１及び環Ｗ^２は、それぞれ独立して、少なくとも１つの二重結合を環の構成要素として有する環構造を表す。
環Ｗ^１及び環Ｗ^２は、それぞれ独立して、置換基を有していてもよい。
Ｒ^１及びＲ^２は、それぞれ独立して、水素原子又は１価の置換基を表し、Ｒ^１及びＲ^２の少なくとも一方は１価の置換基である。］ The present invention includes the following inventions.
[1] A compound having a cation containing a partial structure represented by the following formula (I).

[in the formula (I),
Ring W ¹ and ring W ² each independently represent a ring structure having at least one double bond as a ring constituent.
Ring W ¹ and ring W ² may each independently have a substituent.
R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent, and at least one of R ¹ and R ² is a monovalent substituent. ]
[2] The compound according to [1], wherein at least one selected from R ¹ and R ² is an electron-withdrawing group.
[3] at least one selected from R ¹ and R ² is a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, —CO—R ₁ , —CO—OR ₂ , —CO—NR ₃ R _3k , —CO—S—R ₄ , —CS—R ₅ , —CS—OR ₆ , —CS—S—R 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 an optionally substituted hydrocarbon group or halogen atom.) , -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₂ H or -SO ₃ H.
[4] The compound according to [3], wherein at least one selected from R ¹ and R ² is a cyano group.
[5] The compound according to any one of [1] to [4], wherein the cation containing the partial structure represented by formula (I) is a cation represented by formula (IA).

[In the formula (IA),
Ring W ¹ , ring W ² , R ¹ and R ² each have the same meaning as above.
R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the hydrocarbon group -CH ₂ - or =CH- contained in may be substituted with -O- or -S-.
R ³ and R ⁴ may be linked together to form a ring.
^R5 and ^R6 may be linked together to form a ring. ]
[6] The compound according to [5], wherein the cation represented by formula (IA) is a cation represented by formula (IB) or a cation represented by formula (IC).

[In formula (IB) and formula (IC),
Ring W ¹ , ring W ² , R ¹ and R ² each have the same meaning as above.
Ar ¹ and Ar ² each independently represent an optionally substituted aromatic hydrocarbon group having 6 to 24 carbon atoms.
R ^4A and R ^6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
Ring W3 and ring W4 ^each independently represent a nitrogen ^- containing heterocyclic group. ]
[7] The compound according to any one of [1] to [6], which exhibits a maximum absorption between wavelengths of 400 nm and 700 nm.
[8] A resin composition comprising the compound according to any one of [1] to [7] and a resin.
[9] A composition comprising the compound according to any one of [1] to [7] and a polymerizable monomer.
[10] A molded article molded from the composition according to [8] or [9].
[11] A dyed article dyed with the compound according to any one of [1] to [7].
[12] An optical layer containing a cation containing a partial structure represented by the following formula (I).

[in the formula (I),
Ring W ¹ and ring W ² each independently represent a ring structure having at least one double bond as a ring constituent.
Ring W ¹ and ring W ² may each independently have a substituent.
R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent, and at least one of R ¹ and R ² is a monovalent substituent. ]

An object of the present invention is to provide a novel compound that efficiently absorbs light in the visible light region (400 nm to 750 nm wavelength, preferably 450 nm to 600 nm wavelength) and has good weather resistance.

［式（Ｉ）中、
環Ｗ^１及び環Ｗ^２は、それぞれ独立して、少なくとも１つの二重結合を環の構成要素として有する環構造を表す。
環Ｗ^１及び環Ｗ^２は、それぞれ独立して、置換基を有していてもよい。
Ｒ^１及びＲ^２は、それぞれ独立して、水素原子又は１価の置換基を表し、Ｒ^１及びＲ^２の少なくとも一方は１価の置換基である。］ The compound of the present invention is a compound containing a cation having a partial structure represented by the following formula (I) (hereinafter sometimes referred to as compound (I)).

[in the formula (I),
Ring W ¹ and ring W ² each independently represent a ring structure having at least one double bond as a ring constituent.
Ring W ¹ and ring W ² may each independently have a substituent.
R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent, and at least one of R ¹ and R ² is a monovalent substituent. ]

<Cation>
A cation having a partial structure represented by formula (I) also includes all resonance structures shown below.

Ring W ¹ and ring W ² each independently represent a ring structure having at least one double bond as a ring constituent. Ring W ¹ and ring W ² have one or more double bonds as ring constituents, and the number of double bonds contained in ring W ¹ and ring W ² is usually 1 to 4, preferably 1 to 3. is preferred, 1 or 2 is more preferred, and 1 is even more preferred.
Ring W ¹ and ring W ² may each independently be monocyclic or polycyclic. Ring W ¹ and ring W ² may each independently be an aromatic ring or a ring having no aromaticity (aliphatic ring), but have no aromaticity. A ring is preferred. A ring having no aromaticity can further enhance the selective absorption.
Ring W ¹ and ring W ² may each independently be a heterocyclic ring containing a heteroatom (e.g., a nitrogen atom, an oxygen atom, a sulfur atom, etc.) or a ring composed of a hydrocarbon. . Ring W ¹ and ring W ² are each independently preferably a hydrocarbon ring.
Ring W ¹ and ring W ² are each independently preferably a 3- to 20-membered ring structure, more preferably a 3- to 12-membered ring, and a 4- to 6-membered ring. A ring is preferred.
Ring W ¹ and ring W ² are each independently preferably monocyclic.

Ring ^W1 and ring W2 form ^a condensed ring. The condensed ring formed by ring W ¹ and ring W ² is preferably a condensed ring of aliphatic hydrocarbon, more preferably a condensed ring of aliphatic hydrocarbon having 6 to 40 carbon atoms.
Examples of the condensed ring formed by ring ^W1 and ring ^W2 include the condensed rings described below. * in the following formula represents a bond.

Ring W ¹ and ring W ² may each independently have a substituent. The substituents include halogen atoms such as fluorine, chlorine, bromine and iodine atoms; methyl, ethyl, propyl, normal butyl, isobutyl, tertiary butyl, pentyl, hexyl and heptyl. group, octyl group, nonyl group, decyl group, 2-ethylhexyl group, 4-butyloctyl group, ethenyl group, propenyl group, butenyl group, pentenyl group, ethynyl group, propynyl group, allyl group, cyclohexenyl group, butadienyl aliphatic hydrocarbon groups having 1 to 25 carbon atoms (preferably alkyl groups having 1 to 12 carbon atoms) such as groups; fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2- Carbon such as difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, nonafluorobutyl group Halogenated alkyl groups of numbers 1 to 25; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tertiary butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, 4-butyloctyloxy alkoxy groups having 1 to 25 carbon atoms such as groups; alkylthio groups having 1 to 12 carbon atoms such as methylthio, ethylthio, propylthio, butylthio, pentylthio, and hexylthio groups; fluorinated alkoxy groups having 1 to 12 carbon atoms such as fluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group and hexafluoroisopropoxy group; trifluoromethanethioalkoxy group and the like; Fluorinated alkoxy groups having 1 to 12 carbon atoms; one or two of amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, diphenylamino group, piperidino group, pyrrolidino group, methylethyl, etc. Amino group optionally substituted with a substituent having 1 to 25 carbon atoms; N-position substituted with an alkyl group having 1 to 6 carbon atoms such as carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group a carbamoyl group that may be substituted; an alkylcarbonyloxy group having 2 to 12 carbon atoms such as a methylcarbonyloxy group and an ethylcarbonyloxy group; an alkylsulfonyl group having 1 to 12 carbon atoms such as a methylsulfonyl group and an ethylsulfonyl group; phenyl 6 to 25 carbon atoms such as groups, naphthyl groups, biphenyl groups, anthracenyl groups (preferably an aryl group having 6 to 18 hydrocarbons); an arylsulfonyl group having 6 to 12 carbon atoms such as a phenylsulfonyl group; sulfonyl group; fluoroalkylsulfonyl group having 1 to 12 carbon atoms such as trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group and trifluoroethylsulfonyl group; acyl group having 2 to 12 carbon atoms such as acetyl group and ethylcarbonyl group; aldehyde group; alkoxycarbonyl group having 2 to 12 carbon atoms such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group and butyloxycarbonyl group; alkoxythio group having 2 to 12 carbon atoms such as methoxythiocarbonyl group and ethoxythiocarbonyl group carbonyl group; cyano group; nitro group; hydroxyl group; thiol group; _{sulfo group} ;
^The condensed ring formed by ring W1 and ring W2 may also have ^a substituent, and the substituent may be ^a substituent that ring W1 or ring ^W2 may have.

R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent, and at least one selected from R ¹ and R ² is a monovalent substituent.
The monovalent substituents represented by R ¹ and R ² are not particularly limited as long as they are not hydrogen atoms, and examples include monovalent aliphatic hydrocarbon groups, monovalent aromatic hydrocarbon groups, electron-withdrawing group, an electron-donating group, a heterocyclic group, a group having a polyoxyalkylene group, and the like.

The monovalent aliphatic hydrocarbon groups represented by R ¹ and R ² include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n -pentyl group, isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, Linear or branched alkyl groups having 1 to 25 carbon atoms such as lauryl group, myristyl group, cetyl group, stearyl group, 2-ethylhexyl group, 4-butyloctyl group: cyclopropyl group, cyclobutyl group, cyclopentyl group , a cycloalkyl group having 3 to 25 carbon atoms such as a cyclohexyl group; a cycloalkylalkyl group having 4 to 25 carbon atoms such as a cyclohexylmethyl group; an alkylcycloalkyl group having 4 to 25 carbon atoms such as an isobornyl group; unsaturated aliphatic hydrocarbon groups such as a penyl group, a butenyl group, a pentenyl group, an ethynyl group, a propynyl group, an allyl group, a cyclohexenyl group, and a butadienyl group; A linear or branched alkyl group having 1 to 12 carbon atoms is preferred.

Examples of monovalent aromatic hydrocarbon groups represented by R ¹ and R ² include phenyl, naphthyl, anthracenyl, tetracenyl, pentacenyl, phenanthryl, chrysenyl, triphenylenyl, tetraphenyl, and pyrenyl groups. , a perylenyl group, a coronenyl group, an aryl group having 6 to 18 carbon atoms such as a biphenyl group; an aralkyl group having 7 to 18 carbon atoms such as a benzyl group, a phenylethyl group and a naphthylmethyl group; Examples thereof include arylalkoxy groups of polyalkylene glycol groups, etc., preferably an aryl group having 6 to 18 carbon atoms, more preferably a phenyl group or a benzyl group.

Electron donating groups represented by R ¹ and R ² include hydroxyl group; methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group; an alkoxy group having 1 to 25 carbon atoms such as a 4-butyloctyloxy group; an alkylthio group having 1 to 12 carbon atoms such as a methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group and hexylthio group; Examples thereof include amino groups optionally substituted with one or two alkyl groups having 1 to 6 carbon atoms such as monomethylamino group, monoethylamino group, dimethylamino group, diethylamino group and methylethylamino group.

Examples of the heterocyclic group represented by R ¹ and R ² include a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, a piperidine ring group, and a morpholine ring. C4-C20 aliphatic heterocycles such as group, piperazine ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group, furan ring group, tetrahydrofuran ring group, etc. group or an aromatic heterocyclic group having 3 to 20 carbon atoms.

Groups having a polyoxyalkylene group represented by R ¹ and R ² include groups having an oxyethylene group (--CH ₂ CH ₂ O--), an oxypropyl group (--CH ₂ CH ₂ CH ₂ O--), and the like. is. More specifically, a group represented by —(X ¹¹ O)m—R ¹¹ (X ¹¹ represents an alkylene group having 1 to 6 carbon atoms, R ¹¹ may have a represents an alkyl group of 1 to 6, and m represents an integer of 1 to 6.) and the like.

［式（ｚ－１）中、
Ｒ^２２２は、水素原子、ハロゲン原子、置換基を有していてもよい炭化水素基、ポリオキシアルキレン基を有する基を表す。
Ｘ^１は、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＳ－、－ＣＳＳ－、－ＣＯＳ－、－ＣＳＯ－、－ＳＯ_２－、－ＮＲ^２２３ＣＯ－又は－ＣＯＮＲ^２２４－を表す。
Ｒ^２２３及びＲ^２２４は、それぞれ独立して、水素原子、炭素数１～６のアルキル基又はフェニル基を表す。
＊は結合手を表す。］ Electron-withdrawing groups represented by R ¹ and R ² include, for example, a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -OCF ₃ , -SCF ₃ , - Examples include SF ₅ , —SF ₃ , —SO ₃ H, —SO ₂ H, and groups represented by formula (z-1).

[In the formula (z-1),
R ²²² represents a group having a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, or a polyoxyalkylene group.
X ¹ represents -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO ₂ -, -NR ²²³ CO- or -CONR ²²⁴ -.
R ²²³ and R ²²⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
* represents a bond. ]

Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
Halogenated alkyl groups include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, perfluorohexyl, and dichloromethyl. halogenated alkyl groups having 1 to 25 carbon atoms such as groups, bromomethyl groups and iodomethyl groups. A halogenated alkyl group having 1 to 12 carbon atoms is preferred, a fluoroalkyl group having 1 to 12 carbon atoms is more preferred, and a perfluoroalkyl group having 1 to 12 carbon atoms is even more preferred.
Examples of the halogenated aryl group include halogenated aryl groups having 6 to 18 carbon atoms such as a fluorophenyl group, a chlorophenyl group, and a bromophenyl group. It is more preferably a perfluoroaryl group of 6 to 12, more preferably a pentafluorophenyl group.

X ¹ is preferably -CO-, -COO- or -SO ₂ -.
Halogen atoms represented by R ²²² include fluorine, chlorine, bromine and iodine atoms.
The hydrocarbon group represented by R ²²² includes an aliphatic hydrocarbon group having 1 to 25 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms.
Examples of aliphatic hydrocarbon groups having 1 to 25 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n- Hexyl group, 1-methylbutyl group, 3-methylbutyl group, n-octyl group, n-decyl, 2-hexyl-octyl group, 4-butyloctyl group, cyclohexyl group, etc. Linear, branched, cyclic Alkyl groups having 1 to 25 carbon atoms; unsaturated aliphatic hydrocarbon groups such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl, and butadienyl groups; and preferably an alkyl group having 1 to 12 carbon atoms.
Aromatic hydrocarbon groups having 6 to 18 carbon atoms include aryl groups having 6 to 18 carbon atoms such as phenyl group, naphthyl group, anthracenyl group and biphenyl group; 7 to 18 aralkyl groups and the like.
Substituents which the hydrocarbon group represented by R ²²² may have include halogen atoms, hydroxy groups, alkoxy groups, thioalkyl groups, dialkylamino groups and the like.
Examples of the polyoxyalkylene group-containing group represented by R ²²² include the same polyoxyalkylene group-containing groups represented by R ¹ .

Examples of alkyl groups having 1 to 6 carbon atoms represented by R ²²³ and R ²²⁴ include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n -Pentyl group, n-hexyl group, 1-methylbutyl group and other linear or branched C 1-6 alkyl groups.

The group represented by formula (z-1) includes -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 (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent an optionally substituted hydrocarbon group or halogen atom.), preferably
-CO-R ₁ , -CO-OR ₂ , -SO ₂ -R ₉ are more preferred,
more preferably —SO ₂ —R ₉ ,
—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 is even more preferred.

At least one selected from R ¹ and R ² is preferably an electron-withdrawing group,
cyano group, nitro group, halogenated alkyl group, halogenated aryl group, -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , —CO—NR ₃ R _3k , —CO—S—R ₄ , —CS—R ₅ , —CS—OR ₆ , —CS—S—R 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 are each independently a hydrocarbon group optionally having a substituent or represents a halogen atom.), more preferably _-OCF3 ,
cyano group, nitro group, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, -CO-R ₁ , -CO-OR ₂ , -SO ₂ - more preferably R ₉ ,
more preferably a cyano group, a nitro group, -OCF ₃ , -SCF ₃ , -SF ₅ , -SO ₂ CF ₃ , -SO ₂ -R ₁₀ ,
A cyano group or a nitro group is particularly preferred,
A cyano group is more particularly preferred.

［式（Ｉ－Ａ）中、
環Ｗ^１、環Ｗ^２、Ｒ^１及びＲ^２は、それぞれ上記と同じ意味を表す。
Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立して、水素原子、複素環基、置換基を有していてもよい炭素数１～２４の炭化水素基を表し、該炭化水素基に含まれる－ＣＨ_２－又は＝ＣＨ－は、－Ｏ－又は－Ｓ－に置換されていてもよい。
Ｒ^３及びＲ^４は互いに連結して環を形成してもよい。
Ｒ^５及びＲ^６は互いに連結して環を形成してもよい。］ A cation having a partial structure represented by formula (I) is preferably a cation represented by formula (IA).

[In the formula (IA),
Ring W ¹ , ring W ² , R ¹ and R ² each have the same meaning as above.
R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the hydrocarbon group -CH ₂ - or =CH- contained in may be substituted with -O- or -S-.
R ³ and R ⁴ may be linked together to form a ring.
^R5 and ^R6 may be linked together to form a ring. ]

The hydrocarbon group having 1 to 24 carbon atoms represented by R ³ , R ⁴ , R ⁵ and R ⁶ includes an aliphatic hydrocarbon group having 1 to 24 carbon atoms and an aromatic hydrocarbon group having 6 to 24 carbon atoms. etc.
Examples of aliphatic hydrocarbon groups having 1 to 24 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n- Hexyl group, 1-methylbutyl group, 3-methylbutyl group, n-octyl group, n-decyl, 2-hexyl-octyl group, 4-butyloctyl group, cyclohexyl group, etc. Linear, branched, cyclic Alkyl groups having 1 to 24 carbon atoms; unsaturated aliphatic hydrocarbon groups such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl and butadienyl groups; be done.
Aromatic hydrocarbon groups having 6 to 24 carbon atoms include aryl groups having 6 to 24 carbon atoms such as phenyl group, naphthyl group, anthracenyl group and biphenyl group; 7 to 24 aralkyl groups and the like.
—CH ₂ — or ═CH— contained in the hydrocarbon groups having 1 to 24 carbon atoms represented by R ³ , R ⁴ , R ⁵ and R ⁶ may be substituted with —O— or —S—. good. For example, the group in which -CH ₂ - or =CH- contained in the hydrocarbon group having 1 to 24 carbon atoms is substituted with -O- includes alkoxy group; aryloxy group having ₆ to 18 carbon _atoms such as _{phethoxy group} ; - ₍ X ¹² O) A group represented by _m1 -R ¹² (X ¹² represents an alkylene group having 1 to 6 carbon atoms, and R ¹² represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group. , m1 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less).
The group in which -CH ₂ - or =CH- contained in the hydrocarbon group having 1 to 24 carbon atoms is substituted with -S- includes a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, and the like. an alkylthio group having 1 to 18 carbon atoms; an arylthio group having ₆ to 18 carbon atoms such as a phenylthio group; a thioethylene group _{( -CH2CH2S-} ), a thiopropyl group _{( -CH2CH2CH2S-} ), etc. a group represented by -(X ¹³ S) _m2 -R ¹³ (X ¹³ represents an alkylene group having 1 to 6 carbon atoms, and R ¹³ is a C 1 to 6 group optionally having a hydroxyl group represents an alkyl group, m2 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less).

Examples of substituents which the hydrocarbon groups having 1 to 24 carbon atoms represented by R ³ , R ⁴ , R ⁵ and R ⁶ may have include halogen atoms such as fluorine, chlorine, bromine and iodine atoms. Atom; fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro Halogenated alkyl groups having 1 to 25 carbon atoms such as ethyl group, 1,1,2,2,2-pentafluoroethyl group, nonafluorobutyl group; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group , tertiary butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, alkoxy group having 1 to 25 carbon atoms such as 4-butyloctyloxy group; methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio alkylthio group having 1 to 12 carbon atoms such as hexylthio group; monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, fluorinated alkoxy groups having 1 to 12 carbon atoms such as hexafluoroisopropoxy group; fluorinated alkoxy groups having 1 to 12 carbon atoms such as trifluoromethanethioalkoxy group; amino group, methylamino group, ethylamino group, dimethylamino group , diethylamino group, diphenylamino group, piperidino group, pyrrolidino group, amino group optionally substituted with one or two substituents having 1 to 25 carbon atoms such as methylethyl; carbamoyl group, N-methylcarbamoyl a carbamoyl group optionally substituted with alkyl having 1 to 6 carbon atoms at the N-position such as N,N-dimethylcarbamoyl group; alkyl having 2 to 12 carbon atoms such as methylcarbonyloxy group and ethylcarbonyloxy group; carbonyloxy group; alkylsulfonyl group having 1 to 12 carbon atoms such as methylsulfonyl group and ethylsulfonyl group; arylsulfonyl group having 6 to 12 carbon atoms such as phenylsulfonyl group; 1 carbon atom such as methoxysulfonyl group and ethoxysulfonyl group Alkoxysulfonyl groups of ~12; fluoroalkylsulfonyl groups of 1 to 12 carbon atoms such as trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group and trifluoroethylsulfonyl group; 2 to 12 carbon atoms of acetyl group and ethylcarbonyl group etc. acyl group; aldehyde group; alkoxycarbonyl groups having 2 to 12 carbon atoms such as aryl, ethoxycarbonyl, propoxycarbonyl and butyloxycarbonyl groups; alkoxythiocarbonyl groups having 2 to 12 carbon atoms such as methoxythiocarbonyl and ethoxythiocarbonyl groups; cyano nitro group; hydroxyl group; thiol group; _sulfo group; _carbamoyl group; carboxyl group;

The heterocyclic groups represented by R ³ , R ⁴ , R ⁵ and R ⁶ include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, an imidazolidine ring group, a pyrazolidine ring group, imidazolidine ring group, imidazoline ring group, oxazoline ring group, thiazoline ring group, piperidine ring group, morpholine ring group, piperazine ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, Aliphatic heterocyclic groups having 4 to 20 carbon atoms such as thiazoline ring group, furan ring group and tetrahydrofuran ring group, and aromatic heterocyclic groups having 3 to 20 carbon atoms are included.

The ring formed by combining R ³ and R ⁴ is a ring containing a nitrogen atom as a ring constituent. The ring formed by combining R ³ and R ⁴ may contain a heteroatom other than a nitrogen atom as a ring constituent. The ring formed by combining R ³ and R ⁴ may be a monocyclic ring or a condensed ring. Examples of the ring formed by connecting R ³ and R ⁴ together include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a morpholine ring group, an indoline ring group, an imidazoline ring group, a pyrazole ring group, imidazole ring group, triazole ring group, tetrazole ring group, thiazolidinedione ring group, succinimide ring group, oxazolidone ring group, piperazine ring group, thiomorpholine ring group, decahydroisoquinoline ring group, decahydroquinoline ring group, tetrahydroquinoline ring group, carbazole ring group, phenothiazine ring group, azaadamantane ring group, azocane ring group, azonane ring group, and the like. A hydrogen atom contained in a ring formed by connecting R ³ and R ⁴ to each other may be substituted with an optional substituent, and the optional substituent includes, for example, ring W ¹ and ring W ² . The same groups as the optional substituents can be mentioned.

The ring formed by combining R ⁵ and R ⁶ is a ring containing a nitrogen atom as a ring constituent. The ring formed by combining R ⁵ and R ⁶ may contain a heteroatom other than a nitrogen atom as a ring constituent. The ring formed by combining R ⁵ and R ⁶ may be a monocyclic ring or a condensed ring. The ring formed by connecting R ⁵ and R ⁶ together includes the same ring as the ring formed by connecting R ³ and R ⁴ together. A hydrogen atom contained in a ring formed by connecting R ⁵ and R ⁶ to each other may be substituted with an optional substituent, and the optional substituent includes, for example, ring W ¹ and ring W ² . The same groups as the optional substituents can be mentioned.

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

［式（Ｉ－Ｂ）及び式（Ｉ－Ｃ）中、
環Ｗ^１、環Ｗ^２、Ｒ^１及びＲ^２は、それぞれ上記と同じ意味を表す。
Ａｒ^１及びＡｒ^２は、それぞれ独立して、置換基を有していてもよい炭素数６～２４の芳香族炭化水素基を表す。
Ｒ^４Ａ及びＲ^６Ａは、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数６～２４の炭化水素基を表す。
環Ｗ^３及び環Ｗ^４は、それぞれ独立して、含窒素複素環基を表す。］ The cation represented by formula (IA) is preferably a cation represented by formula (IB) or a cation represented by formula (IC).

[In formula (IB) and formula (IC),
Ring W ¹ , ring W ² , R ¹ and R ² each have the same meaning as above.
Ar ¹ and Ar ² each independently represent an optionally substituted aromatic hydrocarbon group having 6 to 24 carbon atoms.
R ^4A and R ^6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
Ring W3 and ring W4 ^each independently represent a nitrogen ^- containing heterocyclic group. ]

The aromatic hydrocarbon group having 6 to 24 carbon atoms represented by Ar ¹ and Ar ² includes the same aromatic hydrocarbon group represented by R ³ . Ar ¹ and Ar ² are each independently preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms.
The hydrocarbon group having 6 to 24 carbon atoms represented by R ^4A and R ^6A includes the same hydrocarbon group represented by R ³ . R ^4A and R ^6A are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 24 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 24 carbon atoms, A hydrogen atom or an alkyl group having 1 to 6 carbon atoms is more preferable.
The substituents that Ar ¹ , Ar ² , R ^4A and R ^6A may have include the substituents that the hydrocarbon group represented by R ³ may have.

The nitrogen ^- containing heterocyclic group represented by ring W3 and ring ^W4 may be a monocyclic ring or a condensed ring, preferably a condensed ring.
Ring W3 and Ring ^W4 are ^each independently azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, imidazoline ring, pyrazole ring, imidazole ring, triazole ring, tetrazole ring, piperazine ring, thiomorpholine ring, indoline A ring is preferred.

［式（Ｉ－Ｂ１）及び式（Ｉ－Ｃ１）中、環Ｗ^３、環Ｗ^４、Ｒ^１、Ｒ^２、Ｒ^４Ａ、Ｒ^６Ａ、Ａｒ^１及びＡｒ^２は、それぞれ上記と同じ意味を表す。］ The cation represented by formula (IB) is preferably a cation represented by formula (I-B1), and the cation represented by formula (IC) is represented by formula (I-C1). is preferably a cation.

[In formulas (I-B1) and (I-C1), ring W ³ , ring W ⁴ , R ¹ , R ² , R ^4A , R ^6A , Ar ¹ and Ar ² each have the same meaning as above. . ]

Examples of the cation containing the partial structure represented by formula (I) include the cations described below.

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

<Anion>
Compound (I) is usually composed of a cation represented by formula (I) and a paired anion. The combination of the cation and anion represented by formula (I) that compound (I) has is not limited. When the anion has a valence of 2 or more, it may have a plurality of cations represented by formula (I). Moreover, when the valence of the anion is 2 or more, it may have a cation other than the cation represented by the formula (I) and the cation represented by the formula (I).
The anion may be an organic anion or an inorganic anion.

Examples of the organic anion include acetate anion, methide anion, amide anion, sulfonate anion, borate anion, and the like, preferably methide anion, amide anion, sulfonate anion, or borate anion.

［式（ｃ－Ａ）中、Ｒ_１ｃ、Ｒ_２ｃ及びＲ_３ｃは、それぞれ独立して、１価の置換基を表す。］
Ｒ_１ｃ、Ｒ_２ｃ及びＲ_３ｃで表される１価の置換基は特に限定されないが、フッ素原子；モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、テトラフルオロエチル基等の炭素数１～１２のフルオロアルキル基；モノフルオロフェニル基、テトラフルオロフェニル基等の炭素数６～１８のフルオロアリール基；シアノ基；ニトロ基；－ＳＯ_２－Ｒ_１１ｃ（Ｒ_１１ｃは、フッ素原子を有していてもよい炭素数１～１２の炭化水素基を表す。）であることが好ましい。 The methide anion is preferably an anion represented by formula (cA).

[In formula (cA), R _1c , R _2c and R _3c each independently represent a monovalent substituent. ]
The monovalent substituents represented by R _1c , R _2c and R _3c are not particularly limited, but fluorine atoms; 12 _fluoroalkyl groups; _fluoroaryl groups having ₆ to 18 carbon atoms such as a monofluorophenyl group and a tetrafluorophenyl group; a cyano group; a nitro group; represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted).

［式（ｃ－Ｂ）中、Ｒ_４ｃ及びＲ_５ｃは、それぞれ独立して、１価の置換基を表す。］
Ｒ_４ｃ及びＲ_５ｃで表される１価の置換基は特に限定されないが、フッ素原子；モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、テトラフルオロエチル基等の炭素数１～１２のフルオロアルキル基；モノフルオロフェニル基、テトラフルオロフェニル基等の炭素数６～１８のフルオロアリール基；シアノ基；ニトロ基；－ＳＯ_２－Ｒ_１１ｃ（Ｒ_１１ｃは、フッ素原子を有していてもよい炭素数１～１２の炭化水素基を表す。）であることが好ましい。 The amide anion is preferably an anion represented by formula (cB).

[In formula (cB), R _4c and R _5c each independently represent a monovalent substituent. ]
The monovalent substituents represented by R _4c and R _5c are not particularly limited, but fluorine atoms; Alkyl group; fluoroaryl group having 6 to 18 carbon atoms such as monofluorophenyl group and tetrafluorophenyl group; cyano group; nitro group; -SO ₂ -R _11c (R _11c may have a fluorine atom represents a hydrocarbon group having 1 to 12 carbon atoms.) is preferred.

［式（ｃ－Ｃ）中、Ｒ_６ｃは、１価の置換基を表す。］
Ｒ_６ｃで表される１価の置換基は特に限定されないが、フッ素原子；モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、テトラフルオロエチル基等の炭素数１～１２のフルオロアルキル基；モノフルオロフェニル基、テトラフルオロフェニル基等の炭素数６～１８のフルオロアリール基；シアノ基；ニトロ基；－ＳＯ_２－Ｒ_１１ｃ（Ｒ_１１ｃは、フッ素原子を有していてもよい炭素数１～１２の炭化水素基を表す。）であることが好ましい。 The sulfonate anion is preferably an anion represented by formula (cC).

[In the formula (cC), R _6c represents a monovalent substituent. ]
The monovalent substituent represented by R _6c is not particularly limited, but a fluorine atom; a fluoroalkyl group having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a tetrafluoroethyl group; a _fluoroaryl group having ₆ to 18 carbon atoms such as a _{monofluorophenyl} group and a tetrafluorophenyl group; a cyano group; a nitro group; represents a hydrocarbon group of ∼12).

［式（ｃ－Ｄ）中、Ｒ_７ｃ、Ｒ_８ｃ、Ｒ_９ｃ及びＲ_１０ｃは、それぞれ独立して、１価の置換基を表す。］
Ｒ_７ｃ、Ｒ_８ｃ、Ｒ_９ｃ及びＲ_１０ｃで表される１価の置換基は特に限定されないが、フッ素原子；モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、テトラフルオロエチル基等の炭素数１～１２のフルオロアルキル基；モノフルオロフェニル基、テトラフルオロフェニル基等の炭素数６～１８のフルオロアリール基；シアノ基；ニトロ基；－ＳＯ_２－Ｒ_１１ｃ（Ｒ_１１ｃは、フッ素原子を有していてもよい炭素数１～１２の炭化水素基を表す。）であることが好ましい。 The borate anion is preferably an anion represented by formula (cD).

[In formula (cD), R _7c , R _8c , R _9c and R _10c each independently represent a monovalent substituent. ]
The monovalent substituents represented by R _7c , R _8c , R _9c and R _10c are not particularly limited, but fluorine atom; carbon such as monofluoromethyl group, difluoromethyl group, trifluoromethyl group and tetrafluoroethyl group a fluoroalkyl group having a number of 1 to 12; a _fluoroaryl group having ₆ to 18 carbon atoms such as a _{monofluorophenyl} group and a tetrafluorophenyl group; a cyano group; a nitro group; represents a hydrocarbon group having 1 to 12 carbon atoms which may be present).

［式（ｃ－Ａ１）中、Ｒｆ_１、Ｒｆ_２及びＲｆ_３は、それぞれ独立して、炭素数１～１２のフルオロアルキル基を表す。
式（ｃ－Ｂ１）中、Ｒｆ_４及びＲｆ_５は、それぞれ独立して、フッ素原子又は炭素数１～１２のフルオロアルキル基を表す。
式（ｃ－Ｃ１）中、Ｒｆ_６は炭素数１～１２のフルオロアルキル基を表す。
式（ｃ－Ｄ２）中、Ｒ_１ｄ、Ｒ_２ｄ、Ｒ_３ｄ及びＲ_４ｄは、それぞれ独立して、フッ素原子又は炭素数１～１２のフルオロアルキル基を表す。ｎ１～ｎ４は、それぞれ独立して、０～５の整数を表す。］ The anion represented by formula (cA) is preferably an anion represented by formula (c-A1),
The anion represented by formula (cB) is preferably an anion represented by formula (c-B1),
The anion represented by formula (c-C) is preferably an anion represented by formula (c-C1),
The anion represented by formula (cD) is preferably an anion represented by formula (c-D1) or an anion represented by formula (c-D2).

[In formula (c-A1), Rf ₁ , Rf ₂ and Rf ₃ each independently represent a fluoroalkyl group having 1 to 12 carbon atoms.
In formula (c-B1), Rf ₄ and Rf ₅ each independently represent a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms.
In formula (c-C1), Rf ₆ represents a fluoroalkyl group having 1 to 12 carbon atoms.
In formula (c-D2), R _1d , R _2d , R _3d and R _4d each independently represent a fluorine atom or a C 1-12 fluoroalkyl group. n1 to n4 each independently represent an integer of 0 to 5; ]

More specific organic anions include, for example, acetate anion [CH ₃ COO ⁻ ], trifluoroacetate anion [CF ₃ COO ⁻ ], methanesulfonate anion [CH ₃ SO ₃ ⁻ ], trifluoromethanesulfonate anion [CF ₃ SO ₃ ⁻ ], p-toluenesulfonate anion [p-CH ₃ C ₆ H ₄ SO ₃ ⁻ ], bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ⁻ ], bis(nonafluorobutylsulfonyl) imide anion [(C ₄ F ₉ SO ₂ ) ₂ N ⁻ ], tris(trifluoromethanesulfonyl)methanide anion [(CF ₃ SO ₂ ) ₃ C ⁻ ], dimethylphosphinate anion [(CH ₃ ) ₂ POO ⁻ ] , (poly)hydrofluorofluoride anion [F(HF) _m ⁻ ] (m is about 1 to 3), perfluorobutanesulfonate anion [C ₄ F ₉ SO ₃ ⁻ ], bis(pentafluoroethanesulfonyl)imide anion [(C ₂ F ₅ SO ₂ ) ₂ N ⁻ ], perfluorobutanoate anion [C ₃ F ₇ COO ⁻ ], (trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion [(CF ₃ SO ₂ )( CF ₃ CO)N ⁻ ], perfluoropropane-1,3-disulfonate anion [ ⁻ O ₃ S(CF ₂ ) ₃ SO ₃ ⁻ ], carbonate anion [CO ₃ ²⁻ ], tetracyanoborate, tetrakis(penta fluorophenyl)borate, tetrakisphenylborate _, tris ₍ pentafluoroethyl)trifluorophosphate [P- ⁽ _C2F5 ) _3F3 ] and the like.

Examples of inorganic anions include fluoride ion, chloride anion, bromide anion, iodide anion, tetrachloroaluminate anion [AlCl ₄ ⁻ ], heptachlorodialuminate anion [Al ₂ Cl ₇ ⁻ ], tetrafluoroborate anion. [BF ₄ ⁻ ], hexafluorophosphate anion [PF ₆ ⁻ ], perchlorate anion [ClO ₄ ⁻ ], nitrate anion [NO ₃ ⁻ ], hexafluoroarsenate anion [AsF ₆ ⁻ ], hexafluoroantimonate anion [SbF ₆ ⁻ ], hexafluoroniobate anion [NbF ₆ ⁻ ], hexafluorotantalate anion [TaF ₆ ⁻ ], dicyanamide anion [(CN) ₂ N ⁻ ], bis(fluorosulfonyl)imide anion [(FSO ₂ ) ₂ N ⁻ ], phosphate anion (PO ₄ ³⁻ ), thiocyanate anion [SCN ⁻ ], and the like.

The inorganic anion is preferably bis(fluorosulfonyl)imide anion (N ⁻ (SO ₂ F) ₂ ). Examples of organic anions include trifluoroacetate anion [CF ₃ COO ⁻ ], trifluoromethanesulfonate anion [CF ₃ SO ₃ ⁻ ], bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ⁻ ], tris(trifluoro romethanesulfonyl) metanide anion [(CF ₃ SO ₂ ) ₃ C ⁻ ], perfluorobutanesulfonate anion [C ₄ F ₉ SO ₃ ⁻ ], bis(pentafluoroethanesulfonyl) imide anion [(C ₂ F ₅ SO ₂ ) ₂ N ⁻ ], perfluorobutanoate anion [C ₃ F ₇ COO ⁻ ], (trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion [(CF ₃ SO ₂ )(CF ₃ CO)N ⁻ ], perfluorobutanoate anion [C 3 F 7 COO − ], _{Fluoropropane -} 1,3-disulfonate anion ^[ _-O3S (CF2) _3SO3- ^] , tetrakisarylborate anion (tetrakisphenylborate, tetrakis(pentafluorophenyl)borate), tetracyanoborate are preferred, and further Preferably bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ⁻ ], tris(trifluoromethanesulfonyl)methanide anion [(CF ₃ SO ₂ ) ₃ C ⁻ ], tetrakis(pentafluorophenyl)borate , tetracyanoborate, and particularly preferably tetrakis(pentafluorophenyl)borate.

Compound (I) includes, for example, the compounds shown in Tables 1 to 8 below. Compound (1) in Table 1 is a compound having a cation represented by formula (I-1) and a chloride anion, and is a compound described below.

Compound (I) includes compound (3), compound (39), compound (40), compound (41), compound (43), compound (45), compound (46), compound (47), compound (49 ), compound (53), compound (55), compound (56), compound (57), compound (58), compound (59), compound (60), compound (65), compound (66), compound (67 ), compound (70), compound (72), compound (75), compound (115), compound (116), compound (117), compound (119), compound (121), compound (122), compound (123 ), compound (125), compound (129), compound (131), compound (132), compound (133), compound (134), compound (135), compound (136), compound (141), compound (142 ), compound (143), compound (146), compound (148), compound (151), compound (153), compound (154), compound (155), compound (157), compound (159), compound (160 ), compound (161), compound (163), compound (167), compound (169), compound (170), compound (171), compound (172), compound (173), compound (174), compound (179 ), compound (180), compound (181), compound (184), compound (186), compound (189), compound (191), compound (192), compound (193), compound (195), compound (197 ), compound (198), compound (199), compound (201), compound (205), compound (207), compound (208), compound (209), compound (210), compound (211), compound (212 ), compound (217), compound (218), compound (219), compound (222), compound (224), compound (227), compound (267), compound (268), compound (269), compound (271 ), compound (273), compound (274), compound (275), compound (277), compound (281), compound (283), compound (284), compound (285), compound (286), compound (287 ), compound (288), compound (293), compound (294), compound (295), compound (298) and compound (300).

［式中、環Ｗ^１、環Ｗ^２、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ上記と同じ意味を表す。］ <Method for producing compound (I)>
The cation containing the partial structure represented by formula (I) possessed by compound (I) is a compound represented by formula (M) (hereinafter sometimes referred to as compound (M)) and formula (b-1). A compound represented by (hereinafter sometimes referred to as compound (b-1)) and a compound represented by formula (b-2) (hereinafter sometimes referred to as compound (b-2)) are reacted It can be manufactured by

[In the formula, ring W ¹ , ring W ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each have the same meaning as above. ]

The reaction of compound (M), compound (b-1) and compound (b-2) is preferably carried out in the presence of a catalyst.
Carboxylic acids such as formic acid, acetic acid, trifluoroacetic acid; ammonium chloride; titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride , Lewis acids such as lanthanoid triflate; sulfonic anhydrides such as methanesulfonic anhydride, paratoluenesulfonic anhydride, trifluoromethanesulfonic anhydride, and nonafluorobutanesulfonic anhydride; paratoluenesulfonic acid, trifluoromethanesulfone acid, sulfonic acids such as fluorosulfuric acid; electrophilic alkylating agents such as dimethylsulfuric acid, methyltriflate, iodomethane, trimethyloxonium tetrafluoroborate, and dimethylfluorosulfate; sulfonic acid halogens such as paratoluenesulfonyl chloride and trifluoromethanesulfonyl chloride compounds and the like.
The amount of the catalyst to be used is generally 0.001-10 mol, preferably 0.05-2 mol, per 1 mol of compound (M).

The reaction of compound (M), compound (b-1) and compound (b-2) is preferably carried out in the presence of a base.
Examples of the base include metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tert-butoxide, potassium tert-butoxide (preferably alkaline metal alkoxides), etc.; metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide; metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride, sodium borohydride; sodium carbonate, carbonate Metal carbonates such as sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, lithium carbonate, lithium hydrogen carbonate, and cesium carbonate; organic lithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, and phenyllithium; Alkyl metal halides such as methylmagnesium bromide, isopropylmagnesium bromide, n-butylmagnesium bromide, and isopropylmagnesium chloride; lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide , metal amide compounds such as lithium tetramethylpiperidide; pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6- Amine compounds such as tetramethylpiperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, ethylenediamine; metal carboxylates such as sodium acetate, potassium acetate, sodium formate; carboxylate ammonium salts such as ammonium acetate; are mentioned.
The amount of the base to be used is generally 0.1-10 mol, preferably 0.5-2 mol, per 1 mol of compound (M).

The reaction of compound (M), compound (b-1) and compound (b-2) may be carried out in the presence of a solvent.
Examples of solvents include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents such as benzene, toluene, xylene and anisole; aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane and methylcyclohexane; Halogen-based solvents such as dichlorobenzene, meta-dichlorobenzene, para-dichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and n-propyl acetate; methanol, ethanol, isopropanol , hexafluoroisopropanol, n-butanol, isobutanol, tert-butanol and other alcohol solvents; acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone and other ketone solvents; tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentyl methyl ether, 4 - ether solvents such as methyltetrahydropyran, dioxane, diethyl ether, tert-butyl methyl ether, diisopropyl ether, dimethoxyethane, diethoxymethane; amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; dimethylsulfoxide 1,3-dimethyl-2-imidazolidinone; hexamethylphosphoric acid triamide; water and the like. The solvent is preferably a nitrile solvent, a ketone solvent or an aromatic hydrocarbon solvent, more preferably acetonitrile, toluene, methyl ethyl ketone or methyl isobutyl ketone.
The amount of the solvent to be used is generally 0.5 to 1000 parts by mass, preferably 1 to 10 parts by mass, per 1 part by mass of compound (M).

The reaction of compound (M), compound (b-1) and compound (b-2) is carried out by mixing compound (M), compound (b-1) and compound (b-2). .
The reaction of compound (M), compound (b-1) and compound (b-2) involves adding compound (b-1) and compound (b-2) to a mixture of compound (M), a base and a catalyst. preferably added.
The amount of compound (b-1) to be used is generally 0.1 to 20 mol, preferably 0.5 to 4 mol equivalents, per 1 mol of compound (M).
The amount of compound (b-2) to be used is generally 0.1 to 20 mol, preferably 0.5 to 4 mol equivalents, per 1 mol of compound (M).

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

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

Compounds (M) include the compounds described below.

［式中、環Ｗ^１、環Ｗ^２、Ｒ^１及びＲ^２は、上記と同じ意味を表す。
Ｅ_１及びＥ_２は、それぞれ独立して、脱離基を表す。］ Compound (M) is a compound represented by formula (M1-1) (hereinafter sometimes referred to as compound (M1-1)), a compound represented by formula (M1-2) (hereinafter compound (M1- 2)) and a compound represented by formula (M1-3) (hereinafter sometimes referred to as compound (M1-3)).

[In the formula, ring W ¹ , ring W ² , R ¹ and R ² have the same meanings as above.
E ₁ and E ₂ each independently represent a leaving group. ]

Leaving groups represented by E ₁ and E ₂ each independently include halogen atom, succinimide group, maleimide group, saccharin, methylsulfonyl group, p-methoxybenzenesulfonyl group, p-toluenesulfonyl group, trifluoro Examples include a methylsulfonyl group and a nonafluorobutanesulfonyl group.

The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is preferably carried out in the presence of a base.
Examples of the base include the same bases as those used in the reaction of the compound (M), the compound (b-1) and the compound (b-2), and include metal alkoxides, metal hydroxides, metal hydrides, metal It is preferably carbonate, organic lithium, metal amide compound, amine compound or metal carboxylate, potassium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, sodium hydroxide, potassium hydroxide, sodium hydride, hydrogen lithium aluminum chloride, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, methyl lithium, n-butyl lithium, tert-butyl lithium, lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, lithium tetramethylpiperidide, pyridine, 2,6-dimethylpyridine, 2,6-ditertiarybutylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethyl More preferred are piperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, sodium acetate, sodium formate and ammonium acetate.
The amount of the base to be used is generally 0.001-20 mol, preferably 0.1-10 mol, per 1 mol of compound (M1-1).

The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents that can be used in the reaction of compound (M), compound (b-1) and compound (b-2). Acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethylsulfoxide, dimethylformamide and dimethylacetamide are preferred.
Also, the solvent is preferably a dehydrated solvent.

The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is carried out by mixing compound (M1-1), compound (M1-2) and compound (M1-3). It is preferably carried out by mixing the base, compound (M1-1), compound (M1-2) and compound (M1-3).
The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is preferably carried out under a deoxygenating atmosphere (for example, under a nitrogen atmosphere).

The amount of compound (M1-2) to be used is generally 0.1-20 mol, preferably 0.5-10 mol, per 1 mol of compound (M1-1).
The amount of compound (M1-3) to be used is generally 0.1-20 mol, preferably 0.5-10 mol, per 1 mol of compound (M1-1).
The amount of the base to be used is generally 0.001-20 mol, preferably 0.1-10 mol, per 1 mol of compound (M1-1).
The reaction time of compound (M1-1), compound (M1-2) and compound (M1-3) is generally 0.1 to 200 hours.
The reaction temperature of compound (M1-1), compound (M1-2) and compound (M1-3) is usually -100 to 200°C.

As the compound (M1-1), a commercial product may be used, including 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one.
Commercially available products may be used as the compound (M1-2) and the compound (M1-3). For example, chlorocyanate, bromocyanide, p-toluenesulfonyl cyanide, trifluoromethanesulfonyl cyanide, benzyl thiocyanate, tert-butyl isocyanide, copper(I) cyanide, potassium cyanide, 1-cyano-4-(dimethylamino)pyridinium tetrafluoro Borate, p-toluenesulfonylmethyl isocyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Select Floor from Air Products and Chemicals (registered trademark)), benzoyl(phenyliodonio)(trifluoromethanesulfonyl)methanide, 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethane sulfonate, 1-fluoro-3,3-dimethyl-1,2-benzoiodoxol, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide, tetramethylammonium tribromide, fluorine (F ₂ ), Bromine (Br ₂ ), chlorine (Cl ₂ ), iodine (I ₂ ), N-bromophthalimide, N-chlorophthalimide, N-iodophthalimide, N-bromosaccharin, N-(trifluoromethylthio)saccharin, N-( trifluoromethylthio)saccharin, N-(trifluoromethylthio)aniline, N-methyl-N-[(trifluoromethyl)thio]-p-toluenesulfonamide, 1-trifluoromethyl-3,3-dimethyl-1,2 -benzoiodoxol, 1-trifluoromethyl-1,2-benzoiodoxol-3(1H)-one, nitric acid, iodomethane, dimethyl sulfate, methyltriflate, ethyltriflate, n-butyltriflate, acetyl chloride and the like. be done.

When the compound (M), the compound (b-1) and the compound (b-2) are reacted in the presence of a base, a compound ( I) can be obtained.
When the anion of compound (I) is to be exchanged for a desired anion, ion exchange can be carried out by mixing compound (I) with a salt having the desired anion. The ion exchange may be performed in the presence of a solvent. Salts having desired anions include, for example, lithium salts, sodium salts, potassium salts, cesium salts, barium salts, calcium salts, magnesium salts, ammonium salts and the like.

<Composition containing compound (I)>
The present invention also includes compositions containing compound (I).
A composition containing compound (I) can be used for any purpose, and is particularly suitable for use where there is a possibility of exposure to sunlight or light including ultraviolet rays. Specific examples include, for example, glass substitutes and surface coating materials thereof; window glass for housing, facilities, transportation equipment, etc., coating materials for daylighting glass and light source protection glass; window films for housing, facilities, transportation equipment, etc.; Interior and exterior materials such as facilities and transportation equipment, interior and exterior paints, and coating films formed by the paints; alkyd resin lacquer paints and coating films formed by the paints; acrylic lacquer paints and the coating films formed by the paints; Materials for light sources that emit ultraviolet light such as fluorescent lamps and mercury lamps; Materials for shielding electromagnetic waves generated by precision machinery, electronic and electrical equipment, and various displays; For blisters, cups, special packaging, compact disc coats, agricultural and industrial sheet or film materials; anti-fading agents for printed matter, dyed matter, dyes and pigments; for polymer substrates (e.g. plastic parts such as machine and automobile parts optical light films; safety glass and windshield interlayers; electrochromic or photochromic applications; overlaminate films; solar thermal control films; , conditioners, hairdressings, and other cosmetics; sportswear, stockings, hats, and other clothing textiles and fibers; curtains, carpets, wallpaper, and other home interior goods; plastic lenses, contact lenses, artificial eyes, and other medical instruments; Optical supplies such as filters, backlight display films, prisms, mirrors, and photographic materials; stationery such as mold films, decals, anti-graffiti films, tapes, and inks; can be mentioned.

The composition containing compound (I) is a resin composition containing compound (I) and a resin (hereinafter sometimes referred to as "resin composition") or a composition containing compound (I) and a polymerizable monomer. (hereinafter sometimes referred to as “composition (1)”).

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 polyethylene resins, polypropylene resins, olefin resins such as polycycloolefin resins, poly(meth)acrylic acid ester resins, polystyrene resins, styrene-acrylonitrile resins, acrylonitrile-butadiene-styrene resins. Resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyvinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol resin, polyethylene terephthalate resin, polybutylene terephthalate resin, Examples include polyester resins such as liquid crystal polyester resins, polyacetal resins, polyamide resins, polycarbonate resins, polyurethane resins, polyphenylene sulfide resins, and the like. One or more of these resins may be used as a polymer blend or polymer alloy.

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

Shapes of polymer molded articles (molded bodies) formed from the resin composition include flat film, powder, spherical particles, crushed particles, continuous lumps, fibrous, tubular, hollow fiber, granular, plate-like, etc. Any shape such as a porous shape may be used.
When the resin composition is used as an ultraviolet absorbing filter or an ultraviolet absorbing film, the resin is preferably a transparent resin.
A resin composition can be obtained by mixing compound (I) and a resin. Compound (I) may be contained in an amount necessary to impart desired performance, and can be contained, for example, in an amount of 0.00001 to 99 parts by mass with respect to 100 parts by mass of the resin.
The resin composition may contain other additives such as solvents, crosslinking catalysts, tackifiers, plasticizers, softeners, dyes, pigments, inorganic fillers, etc., if necessary.

The polymerizable monomer used in the composition (1) is not particularly limited, but is preferably a radically polymerizable monomer, more preferably a radically photopolymerizable monomer, and further preferably a (meth)acrylate. preferable.
(Meth)acrylates include monofunctional (meth)acrylate monomers having one (meth)acryloyloxy group in the molecule, and bifunctional (meth)acrylate monomers having two (meth)acryloyloxy groups in the molecule. , polyfunctional (meth)acrylate monomers having 3 or more (meth)acryloyloxy groups in the molecule.
Composition (1) preferably further contains a polymerization initiator. When the polymerizable monomer is a radically polymerizable monomer, the polymerization initiator is preferably a radical polymerization initiator, more preferably a photopolymerization initiator.
Composition (1) can be obtained by mixing compound (I) and a polymerizable monomer. Compound (I) may be contained in an amount necessary to impart desired performance, and may be contained, for example, in an amount of 0.01 to 20 parts by mass with respect to 100 parts by mass of the polymerizable monomer.
Composition (1) may contain other additives such as solvents, crosslinking catalysts, tackifiers, plasticizers, softeners, dyes, pigments, inorganic fillers, etc., if necessary.

<Layer containing compound (I)>
The present invention includes optical layers containing cations containing partial structures represented by formula (I). An optical layer containing a cation containing the partial structure represented by formula (I) is usually formed from an optical layer containing compound (I). An optical layer containing the compound (I) can be used, for example, in an image display device (FPD: flat panel display) such as an organic EL display device or a liquid crystal display device by laminating it on a display device such as an organic EL device or a liquid crystal cell. can be done. The optical layer may be formed using the resin composition of the present invention. When the resin composition of the present invention is applied to an image display device, the optical layer formed from the resin composition of the present invention may be applied to any of a film layer, an adhesive layer, a coat layer, and the like. A layer or coat layer is preferred.
The optical layer containing compound (I) is preferably formed from the resin composition or composition (1) described above.
The optical layer containing compound (I) may consist of only the optical layer containing compound (I), or may be an optical layered body in which a layer containing compound (I) and another layer are laminated. . Other layers include, for example, a polarizing film (polarizer), a retardation film, a thermoplastic resin film, a wavelength conversion layer, and the like. If the optical layered body is a layered body in which an optical layer of the present invention, an adhesive layer and a polarizing film are laminated in this order, the optical layer of the present invention is an optical layer (optical film) formed from a resin composition. Preferably. If the optical laminate is a laminate in which the optical layer of the present invention, a thermoplastic resin film, an adhesive layer, and a polarizing film are laminated in this order, the optical layer of the present invention is formed from the composition (1). It is preferably an optical layer (coat layer). If the optical laminate is a laminate in which the retardation film, the optical layer of the present invention, and the retardation film are laminated in this order, the optical layer of the present invention is an optical layer (adhesive layer) formed from a resin composition. Preferably. When the optical layer of the present invention and the wavelength conversion layer are laminated, it is preferable that the optical layer of the present invention is arranged on the viewing side of the wavelength conversion layer.

<Adhesive composition>
When the layer formed from the composition of the present invention is a pressure-sensitive adhesive layer, a pressure-sensitive adhesive composition (hereinafter referred to as pressure-sensitive adhesive may be referred to as composition (1)). The pressure-sensitive adhesive composition (1) further includes a radical-curable component (D), an initiator (E), and a light-absorbing compound (F) other than the compound (I) (hereinafter sometimes referred to as a light-selective absorbing compound (F). ), may contain an antistatic agent, etc., and preferably contains at least one selected from the group consisting of a radical curing component (D), an initiator (E) and a photoselective absorption compound (F) .

The resin (A) is not particularly limited as long as it is a resin used in adhesive compositions. It is preferable that the resin (A) does not exhibit maximum absorption in the wavelength range of 300 nm to 780 nm.
Resin (A) is preferably a resin having a glass transition temperature (Tg) of 40° C. or lower. The glass transition temperature (Tg) of resin (A) is more preferably 20° C. or lower, still more preferably 10° C. or lower, and particularly preferably 0° C. or lower. The glass transition temperature of the resin (A) is usually −80° C. or higher, preferably −70° C. or higher, more preferably −60° C. or higher, further preferably −55° C. or higher. , −50° C. or higher. When the glass transition temperature of the resin (A) is 40° C. or lower, it is advantageous for improving the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (1) to the adherend. Moreover, when the glass transition temperature of the resin (A) is −80° C. or higher, it is advantageous for improving the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (1). The glass transition temperature can be measured with a differential scanning calorimeter (DSC).

Examples of the resin (A) include (meth)acrylic resins, silicone resins, rubber resins, urethane resins, etc., and (meth)acrylic resins are preferred.

The (meth)acrylic resin is preferably a polymer containing (preferably at least 50% by mass) a structural unit derived from (meth)acrylic ester as a main component. (Meth)acrylic resins are structural units derived from monomers other than one or more (meth)acrylic acid esters (e.g., hydroxyl groups, carboxyl groups, derived from monomers having polar functional groups such as amino groups) structural unit).

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

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. An isocyanate-based cross-linking agent is preferred from the viewpoint of speed and the like.
The content of the cross-linking agent (B) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, more preferably 0.15 parts by mass, relative to 100 parts by mass of the resin (A). 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.

Examples of the silane compound (C) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3 - glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane and the like.
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 parts by mass, relative to 100 parts by mass of the resin (A). 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.

Examples of the radical-curable component (D) include radical-curable components such as compounds or oligomers that cure by a radical polymerization reaction.
Examples of the radically polymerizable component (D) include (meth)acrylate compounds, styrene compounds, vinyl compounds and the like.
The pressure-sensitive adhesive composition (1) may contain two or more radical-curable components (D).

The (meth)acrylate compound includes a (meth)acrylate monomer having at least one (meth)acryloyloxy group in the molecule, a (meth)acrylamide monomer, and at least two (meth)acryloyl groups in the molecule. (Meth)acryloyl group-containing compounds such as (meth)acrylic oligomers having The (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. Only one type of (meth)acrylate compound may be used alone, or two or more types may be used in combination.

(Meth)acrylate monomers include monofunctional (meth)acrylate monomers having one (meth)acryloyloxy group in the molecule, and bifunctional (meth)acrylates having two (meth)acryloyloxy groups in the molecule. Examples include monomers and polyfunctional (meth)acrylate monomers having 3 or more (meth)acryloyloxy groups in the molecule.
(Meth)acrylate compounds are preferable, and polyfunctional (meth)acrylate compounds are more preferable. The polyfunctional (meth)acrylate compound is preferably trifunctional or higher.

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

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

Examples of thermal polymerization initiators include compounds that generate radicals by heating (thermal radical generators), compounds that generate acids by heating (thermal acid generators), and compounds that generate bases by heating (thermal base generators). ) and the like.
Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), and light energy and a compound (photobase generator) that generates a base by absorbing the .

The initiator (E) is preferably selected from those suitable for the polymerization reaction of the radical-curable component (D) described above, preferably a radical polymerization initiator, more preferably a radical photopolymerization initiator. preferable.
Examples of radical polymerization initiators include alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, phosphine compounds and the like. The radical polymerization initiator is preferably a radical photopolymerization initiator, and more preferably an oxime ester-based radical photopolymerization initiator from the viewpoint of the reactivity of the polymerization reaction. By using an oxime ester photoradical polymerization initiator, the reaction rate of the radical curing component (D) can be increased even under curing conditions with a weak illumination 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, and 0.5 to 5 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably 0.75 to 4 parts by mass, particularly preferably 1 to 3 parts by mass.

The photoselective absorption compound (F) is a light absorption compound other than the compound (I), for example, a compound (ultraviolet absorber) that absorbs light with a wavelength of 250 nm to 380 nm (preferably 250 nm or more and less than 360 nm). , a compound (dye) that absorbs wavelengths from 380 nm to 780 nm, and a compound (infrared absorber) that absorbs wavelengths from 780 nm to 1500 nm.
The structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light with a wavelength of 250 nm to 380 nm. Benzotriazole compounds, benzophenone compounds, triazine compounds, salicylic acid compounds, cyanoacrylate compounds, Compounds such as benzoxazine compounds are preferred.
The content of the photoselective absorption compound (F) is usually 0.1 to 50 parts by mass, preferably 0.2 to 40 parts by mass, more preferably 0, per 100 parts by mass of the resin (A). .5 to 30 parts by mass, more preferably 1 to 25 parts by mass, and particularly preferably 2 to 20 parts by mass.

<Dyed article dyed with compound (I)>
The present invention includes dyed articles (eg, textiles, films, resins, etc.) dyed with compound (I). Dyeing with compound (I) is carried out, for example, by immersing articles such as fibers, films, and resins in a solution obtained by dissolving compound (I) in a solvent.

EXAMPLES The present invention will be described in more detail below with reference to examples and comparative examples. "%" and "parts" in Examples and Comparative Examples are "% by mass" and "parts by mass" unless otherwise specified.

ジムロート冷却管及び温度計を設置した５００ｍＬ－四ツ口フラスコ内を窒素雰囲気とし、式（Ｍ－１）で表される化合物（７－ヒドロキシ－２，３，４，４ａ，５，６－ヘキサヒドロナフタレン－２－オン）２５部、エタノール１５０部、水酸化カリウム１０．３部、パラトルエンスルホニルシアニド３３．１１部を加えて氷浴中で４時間撹拌した。得られた混合物から溶媒を留去した後、精製し、式（Ｍ－２）で表される化合物１７．４部を得た。
ジムロート冷却管及び温度計を設置した１００ｍＬ－四ツ口フラスコ内を窒素雰囲気とし、式（Ｍ－２）で表される化合物４部、脱水アセトニトリル４０部、ジイソプロピルエチルアミン６．６部を加えて氷浴撹拌した。得られた混合物にトリフルオロメタンスルホン酸無水物７．２部を加えて１５分間氷浴撹拌した後、さらにインドリン３部を加えて２時間氷浴撹拌した。得られた混合物から溶媒を留去した後、塩酸と酢酸エチルとを用いて精製し、式（１）で表される化合物を得た。 Example 1: Synthesis of compound represented by formula (1)

A 500 mL-four-necked flask equipped with a Dimroth condenser and a thermometer was set to a nitrogen atmosphere, and the compound represented by the formula (M-1) (7-hydroxy-2,3,4,4a,5,6-hexa 25 parts of hydronaphthalene-2-one), 150 parts of ethanol, 10.3 parts of potassium hydroxide and 33.11 parts of p-toluenesulfonyl cyanide were added and stirred for 4 hours in an ice bath. After distilling off the solvent from the obtained mixture, the mixture was purified to obtain 17.4 parts of the compound represented by the formula (M-2).
A 100 mL-four-necked flask equipped with a Dimroth condenser and a thermometer is set to a nitrogen atmosphere, and 4 parts of the compound represented by the formula (M-2), 40 parts of dehydrated acetonitrile, and 6.6 parts of diisopropylethylamine are added to ice. Agitate the bath. After adding 7.2 parts of trifluoromethanesulfonic anhydride to the resulting mixture and stirring in an ice bath for 15 minutes, 3 parts of indoline was added and the mixture was stirred in an ice bath for 2 hours. After distilling off the solvent from the resulting mixture, the mixture was purified using hydrochloric acid and ethyl acetate to obtain a compound represented by formula (1).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by formula (1) was produced. Also, the presence of chloride anions was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis).
¹ H-NMR (heavy dimethyl sulfoxide) δ: 7.07-7.42 (m, 8H), 5.95 (s, 1H), 4.11-4.16 (m, 4H), 2.99- 3.20 (m, 5H), 2.50 (m, 2H), 2.05 (m, 2H), 1.56 (m, 4H)
LC-MS; [M] = 392.5

<Measurement of maximum absorption wavelength and gram extinction coefficient ε>
The resulting 2-butanone solution (0.003 g/L) of the compound represented by formula (1) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Then, the absorbance in the wavelength range from 300 to 800 nm was measured at every 1 nm step by the double beam method.
The gram extinction coefficient for each wavelength was calculated 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.
ε(λ)=A(λ)/CL
[Wherein, ε (λ) represents the gram extinction coefficient (L/(g cm)) of the compound represented by the formula (1) at the wavelength λ nm, A (λ) represents the absorbance at the wavelength λ nm, and C represents the concentration (g/L) and L represents the optical path length (m) of the quartz cell. ]
The maximum absorption wavelength of the obtained compound represented by formula (1) was 509 nm. The gram extinction coefficient ε (λmax) at the maximum absorption wavelength of the obtained compound represented by formula (1) was 52 L/(g·cm).

Also, from the measured absorbance, two wavelengths were confirmed at which the absorbance was half the absorbance at the maximum absorption wavelength. Of the wavelengths at the two points, the wavelength on the short wavelength side was subtracted from the wavelength on the long wavelength side to obtain the full width at half maximum. The full width at half maximum of the compound represented by formula (1) was 67 nm.

Polymerization Example 1: Preparation of acrylic resin (A1) Into a reaction vessel equipped with a condenser, a nitrogen inlet tube, a thermometer and a stirrer, 81.8 parts of ethyl acetate, 96 parts of butyl acrylate and 2-hydroxy acrylate were added as solvents. A mixed solution of 3 parts of ethyl methyl and 1 part of acrylic acid was charged, and the internal temperature was raised to 55° C. while replacing the air in the apparatus with nitrogen gas to make it oxygen-free. Thereafter, a solution obtained by dissolving 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added to the whole amount. This temperature was maintained for 1 hour after the addition of the initiator, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C to obtain a concentration of the acrylic resin. When the concentration reached 35%, the addition of ethyl acetate was stopped, and the mixture was maintained at this temperature until 12 hours had passed since 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 obtained acrylic resin had a polystyrene-equivalent weight average molecular weight Mw of 1,400,000 and an Mw/Mn of 5.5 by GPC. This is designated as acrylic resin (A1).

Example 2: Preparation of resin composition (1) (adhesive composition (1)) A cross-linking agent (Tosoh Co., Ltd.: product name “Coronate L”, isocyanate compound, solid content 75%) 0.5 parts, silane compound (manufactured by Shin-Etsu Chemical Co., Ltd.: product name “KBM3066”) 0.28 parts, formula (1) 0.5 part of the compound represented by is mixed, and 2-butanone is added so that the solid content concentration becomes 14% to obtain a resin composition (1) (adhesive composition). In addition, the compounding amount of the said crosslinking agent is the number of mass parts as an active ingredient.

Example 3, Comparative Example 1: Preparation of resin compositions (2) and (3) Resin compositions ( 2), to prepare a resin composition (3). The amount of the cross-linking agent is the number of parts by mass as the active ingredient, and the amount of the resin (A) is the number of parts by mass of the solid content.

Each abbreviation in Table 9 has the following meaning.
Acrylic resin (A1): Acrylic resin (A1) synthesized in Polymerization Example 1
Formula (1): compound represented by formula (1) synthesized in Example 1 Coronate L: manufactured by Tosoh Corporation, trade name: Coronate L, isocyanate-based cross-linking agent KBM3066: manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, silane coupling agent Formula (B): Compound (3-butyl-2-[3-(-3-butyl-5 -phenyl-2(3H)-benzolylidene)-1-propen-1-yl]-5-phenyl-benzoxazolium p-toluenesulfonate), and the full width at half maximum determined in the same manner as above was 44 nm.

<Evaluation of Molded Body of Resin Composition (1)>
[Preparation of resin molding (1)]
The resulting resin composition (1) was applied to the release-treated surface of a release-treated polyethylene terephthalate film [PLR-382190, available from Lintec Corporation] using an applicator. and dried at 100° C. for 1 minute to prepare a resin molding (adhesive layer) (1). The thickness of the obtained resin molding (1) was 20 μm.

[Evaluation of bleeding resistance of resin molded product (1)]
A separate film was further laminated on one side of the obtained resin molding (1) to obtain a pressure-sensitive adhesive layer with a double-sided separate film. The obtained resin layer (1) with a double-sided separate film was stored in air at a temperature of 23 to 25° C. for 1 month. The presence or absence of in-plane crystal precipitation of the compound was confirmed using a microscope for the resin molding (1) with the double-sided separate film after storage. A case where there was no crystal precipitation was designated as a, and a case where there was crystal precipitation was designated as b. Table 10 shows the evaluation results.

[Measurement of absorbance retention rate of resin molding (1)]
A polarizing plate was prepared by laminating a cycloolefin film having a thickness of 13 μm using an adhesive layer on one side of a polarizer having a thickness of 8 μm.
After laminating the resin molded body (1) on the polarizer side of the polarizing plate with a laminator, it is cured for 7 days under the conditions of a temperature of 23° C. and a relative humidity of 65%, and a cycloolefin film/polarizer/resin molded body (1) is obtained. / A laminate of separate films was obtained. The resulting laminate was cut into a size of 30 cm x 30 cm, the separate film was peeled off, and the resin molding (1) and non-alkali glass [trade name "EAGLE XG" manufactured by Corning] were laminated. A laminate (1-1) having a laminate structure of cycloolefin film/polarizer/resin molding (1)/glass was obtained.
The resulting laminate (1-1) was placed in a Sunshine Weather Meter (manufactured by Suga Test Instruments Co., Ltd.) for 75 hours under the conditions of a temperature of 63° C. and a relative humidity of 50% RH to carry out a weather resistance test. The absorbance of the laminate (1-1) taken out was measured in the same manner as above. Based on the measured absorbance, the absorbance retention rate of the sample at a wavelength of 500 nm was calculated according to the following formula. Table 10 shows the results. The closer the absorbance retention rate is to 100, the better the weather resistance without deterioration of the selective light absorption function.
As the absorption wavelength for evaluating the absorbance retention rate, the wavelength at which the absorbance is 1 to 1.5 on the longer wavelength side of the maximum absorption wavelength was selected among the measured absorbances. This is because the wavelength is the most sensitive absorbance region in terms of measurement accuracy of the spectrometer.
Absorbance retention rate (%)
= (A (500) after weather resistance test/A (500) before weather resistance test) x 100
[In the formula, A(500) represents the absorbance of the laminate (1-1). ]

Using the resin composition (2) instead of the resin composition (1), a resin molding (2) and a laminate (2-1) were produced and evaluated in the same manner. Table 10 shows the results.

Using the resin composition (3) instead of the resin composition (1), a resin molding (3) and a laminate (3-1) were produced and evaluated in the same manner. The absorbance retention rate was evaluated at a wavelength of 510 nm. Table 10 shows the results.

The compounds of the present invention have high absorption selectivity for light near the maximum absorption wavelength. Moreover, the resin composition containing the compound of the present invention has high absorbance retention even after the weather resistance test, and has good weather resistance.

Claims (12)

A compound having a cation containing a partial structure represented by the following formula (I).

[in the formula (I),
Ring W ¹ and ring W ² each independently represent a ring structure having at least one double bond as a ring constituent.
Ring W ¹ and ring W ² may each independently have a substituent.
R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent, and at least one of R ¹ and R ² is a monovalent substituent. ] 2. The compound according to claim 1, wherein at least one selected from ^R1 and ^R2 is an electron-withdrawing group. at least one selected from R ¹ and R ² is a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -CO-R ₁ , -CO-OR 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 (R ₁ , R ₂ , R ₃ , R _3k , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each independently represent an optionally substituted hydrocarbon group or a halogen atom.), —OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₂ H or -SO ₃ H. 4. The compound according to claim 3, wherein at least one selected from ^R1 and ^R2 is a cyano group. 5. The compound according to any one of claims 1 to 4, wherein the cation containing the partial structure represented by formula (I) is a cation represented by formula (IA).

[In the formula (IA),
Ring W ¹ , ring W ² , R ¹ and R ² each have the same meaning as above.
R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the hydrocarbon group -CH ₂ - or =CH- contained in may be substituted with -O- or -S-.
R ³ and R ⁴ may be linked together to form a ring.
^R5 and ^R6 may be linked together to form a ring. ] 6. The compound according to claim 5, wherein the cation represented by formula (IA) is a cation represented by formula (IB) or a cation represented by formula (IC).

[In formula (IB) and formula (IC),
Ring W ¹ , ring W ² , R ¹ and R ² each have the same meaning as above.
Ar ¹ and Ar ² each independently represent an optionally substituted aromatic hydrocarbon group having 6 to 24 carbon atoms.
R ^4A and R ^6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
Ring W3 and ring W4 ^each independently represent a nitrogen ^- containing heterocyclic group. ] The compound according to any one of claims 1 to 6, which exhibits a maximum absorption between wavelengths of 400 nm and 700 nm. A composition comprising the compound according to any one of claims 1 to 7 and a resin. A composition comprising the compound according to any one of claims 1 to 7 and a polymerizable monomer. A molded article molded from the composition according to claim 8 or 9. A dyed article dyed with the compound according to any one of claims 1 to 7. An optical layer containing a cation containing a partial structure represented by the following formula (I).

[in the formula (I),
Ring W ¹ and ring W ² each independently represent a ring structure having at least one double bond as a ring constituent.
Ring W ¹ and ring W ² may each independently have a substituent.
R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent, and at least one of R ¹ and R ² is a monovalent substituent. ]