KR20230131232A - Compounds, compositions containing them, molded products, dyes, optical layers, and laminates - Google Patents

Abstract

The present invention aims to provide a novel compound that efficiently absorbs light in the visible region and at the same time has good weather resistance, comprising at least one cation selected from the cation represented by formula (I-A) and the cation represented by formula (I-B). Provided are compounds containing cations and anions, compositions containing the same, molded products, dyes, optical layers, and laminates.

Description

Compounds, compositions containing them, molded products, dyes, optical layers, and laminates

The present invention relates to compounds, compositions containing the same, molded products, dyes, optical layers, and laminates.

Pigment compounds that absorb visible light are widely used in textiles, inks, paints, containers, packaging materials, printed materials, optical products, glasses, and display devices for the purpose of coloring objects or transmitting or absorbing light of a specific wavelength. It is being used. Important properties of colorant compounds include selective absorption (sharpness of the absorption spectrum) and durability (especially weather resistance). Among pigment compounds, cyanine pigments can control the wavelength showing maximum absorption over a wide range 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 carbons in the polymethine skeleton. In addition, the majority of cyanine pigments are relatively It has been widely used because it exhibits high selective absorption (e.g., U.S. Patent No. 6004536).

However, although cyanine pigments have high selective absorption, they are often poor in durability (especially weather resistance), so compounds with good durability are required.

The present invention includes the following inventions.

[1] A compound containing at least one cation and an anion selected from the cation represented by formula (I-A) and the cation represented by formula (I-B).

[Formula 1]

[In formulas (I-A) and (I-B),

Ring W ¹ and Ring W ² each independently represent a ring structure having at least one double bond as a ring component.

Ring W ¹ and ring W ² may each independently have a substituent.

Ring W ³ and Ring W ⁴ each independently represent a nitrogen-containing heterocyclic group that may have a substituent. However, ring W ³ and ring W ⁴ do not contain a pyrrole ring structure and a sulfur atom.

Ar ¹ and Ar ² each independently represent an aromatic group.

R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent.]

[2] The compound according to [1], wherein the anion is an organic anion.

[3] The compound according to [2], wherein the anion is a methide anion, an amide anion, a sulfonate anion, or a borate anion.

[4] [2] or [3], wherein the anion is an anion represented by the formula (c-A), an anion represented by the formula (c-B), an anion represented by the formula (c-C), and an anion represented by the formula (c-D). A compound that is one of the anions.

[Formula 2]

[In formula (cA), R _1c , R _2c and R _3c each independently represent a monovalent substituent.

In formula (cB), R _4c and R _5c each independently represent a monovalent substituent.

In formula (cC), R _6c represents a monovalent substituent.

In formula (cD), R _7c , R _8c , R _9c and R _10c each independently represent a monovalent substituent.]

[5] In [4], R _1c , R _2c , R _3c , R _4c , R _5c , R _6c , R _7c , R _8c , R _9c and R _10c are each independently a fluorine atom, a carbon number of 1 to 12 A fluoroalkyl group, a fluoroaryl group having 6 to 18 carbon atoms, a cyano group, a nitro group, and/or -SO ₂ -R _11c (R _11c represents a hydrocarbon group having 1 to 12 carbon atoms that may have a fluorine atom). compound.

[6] [4] or [5], wherein the anion is an anion represented by formula (c-A1), an anion represented by formula (c-B1), an anion represented by formula (c-C1), formula A compound that is either an anion represented by (c-D1) or an anion represented by the formula (c-D2).

[Formula 3]

[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 fluoroalkyl group having 1 to 12 carbon atoms. n1 to n4 each independently represent an integer from 0 to 5.]

[7] The compound according to [6], wherein the anion is tetrakis(pentafluorophenyl)borate anion.

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

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

[12] An optical layer containing the compound according to any one of [1] to [7].

[13] A laminate in which an optical layer and a wavelength conversion layer according to [12] are laminated.

[14] A compound represented by the following formula (M-A).

[Formula 4]

[In formula (M-A),

Ring W ¹ and Ring W ² each independently represent a ring structure having at least one double bond as a ring component.

Ring W ¹ and ring W ² may each independently have a substituent.

Ring W ⁴ represents a nitrogen-containing heterocyclic group that may have a substituent. However, ring W ⁴ does not contain a pyrrole ring structure and a sulfur atom.]

The purpose of the present invention is to provide a novel compound that efficiently absorbs light in the visible light range (wavelength 400 nm to 750 nm, preferably wavelength 450 nm to 600 nm) and at the same time has good weather resistance.

Best mode for carrying out the invention

The compound of the present invention is a compound containing at least one cation and an anion selected from the cation represented by formula (I-A) and the cation represented by formula (I-B) (hereinafter sometimes referred to as compound (I)).

[Formula 5]

[In formulas (I-A) and (I-B),

Ring W ¹ and Ring W ² each independently represent a ring structure having at least one double bond as a ring component.

Ring W ¹ and ring W ² may each independently have a substituent.

Ring W ³ and Ring W ⁴ each independently represent a nitrogen-containing heterocyclic group that may have a substituent. However, ring W ³ and ring W ⁴ do not contain a pyrrole ring structure and a sulfur atom.

Ar ¹ and Ar ² each independently represent an aromatic group.

R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent.]

<cation>

The cation represented by formula (I-A) contains the following resonance structure.

[Formula 6]

Additionally, the cation represented by formula (I-B) contains the following resonance structure.

[Formula 7]

Ring W ¹ and Ring W ² each independently represent a ring structure having at least one double bond as a ring component. Ring W ¹ and Ring W ² have one or more double bonds as ring components, but the double bonds contained in Ring W ¹ and Ring W ² are usually 1 to 4, preferably 1 to 3, and 1 or It is more preferable that it is 2, and it is still more preferable that it is 1.

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 non-aromatic ring (aliphatic ring), but it is preferable that they are a non-aromatic ring. If it is a ring that does not have aromaticity, selective absorption can be further improved.

Ring W ¹ and ring W ² may each independently be a heterocycle containing a hetero atom (eg, a nitrogen atom, an oxygen atom, a sulfur atom, etc.), or may be a ring made of hydrocarbon. It is preferable that ring W ¹ and ring W ² are each independently a hydrocarbon ring.

Ring W ¹ and Ring W ² are each independently preferably a ring structure of a 3-membered ring to a 20-membered ring, more preferably a 3-membered ring to a 12-membered ring, and preferably a 4-membered ring to a 6-membered ring. .

It is preferable that ring W ¹ and ring W ² are each independently monocyclic.

Ring W ¹ and ring W ² form a condensed ring. The condensed ring formed by ring W ¹ and ring W ² is preferably an aliphatic hydrocarbon condensed ring, and more preferably is an aliphatic hydrocarbon condensed ring having 6 to 40 carbon atoms.

The condensed ring formed by ring W ¹ and ring W ² includes, for example, a condensed ring represented by the following formula (W ¹ -1) to a condensed ring represented by the formula (W ¹ -18). * in the following formula represents a binding site.

[Formula 8]

Ring W ¹ and ring W ² may each independently have a substituent. The substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; Methyl group, ethyl group, propyl group, normal butyl group, isobutyl group, tertiary butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, 2-ethylhexyl group, 4-butyloctyl group, aliphatic hydrocarbon groups having 1 to 25 carbon atoms such as ethenyl group, propenyl group, butenyl group, pentenyl group, ethynyl group, propynyl group, allyl group, cyclohexenyl group, butadienyl group (preferably an alkyl group having 1 to 12 carbon atoms); 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 loethyl group, 1,1,2,2,2-pentafluoroethyl group, and nonafluorobutyl group; 1 to 25 carbon atoms such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tertiary butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, 4-butyloctyloxy group, etc. alkoxy group; Alkylthio groups having 1 to 12 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, and hexylthio group; Monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, hexafluoroisopropoxy group fluorinated alkoxy groups having 1 to 12 carbon atoms, such as; Fluorinated alkoxy groups having 1 to 12 carbon atoms, such as trifluoromethane thioalkoxy groups; An amino group that may be substituted with one or two substituents having 1 to 25 carbon atoms, such as amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, diphenylamino group, piperidino group, pyrrolidino group, and methylethyl; Carbamoyl groups in which the N-position may be substituted with an alkyl group having 1 to 6 carbon atoms, such as carbamoyl group, N-methylcarbamoyl group, and N,N-dimethylcarbamoyl group; Alkylcarbonyloxy groups having 2 to 12 carbon atoms, such as methylcarbonyloxy group and ethylcarbonyloxy group; Alkylsulfonyl groups having 1 to 12 carbon atoms, such as methylsulfonyl group and ethylsulfonyl group; aromatic hydrocarbon groups having 6 to 25 carbon atoms such as phenyl group, naphthyl group, biphenyl group, and anthracenyl group (preferably an aryl group having 6 to 18 hydrocarbons); Arylsulfonyl groups having 6 to 12 carbon atoms, such as phenylsulfonyl group; Alkoxysulfonyl groups having 1 to 12 carbon atoms, such as methoxysulfonyl group and ethoxysulfonyl group; Fluoroalkyl sulfonyl groups having 1 to 12 carbon atoms, such as trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, and trifluoroethylsulfonyl group; Acyl groups having 2 to 12 carbon atoms, such as acetyl group and ethyl carbonyl group; aldehyde group; Alkoxycarbonyl groups having 2 to 12 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, and butyloxycarbonyl group; Alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as methoxythiocarbonyl group and ethoxythiocarbonyl group; Cyano group; nitro group; hydroxyl group; Thiol group; tongue group; Cavamo Diary; Carboxyl group; -SF ₃ ; -SF ₅ , etc.

The condensed ring formed by ring W ¹ and ring W ² may also have a substituent, and the substituent includes substituents that ring W ¹ or ring W ² may have.

Ring W ³ and ring W ⁴ each independently represent a nitrogen-containing heterocyclic group. However, ring W ³ and ring W ⁴ do not contain a pyrrole ring structure and a sulfur atom. In addition, not containing a pyrrole ring structure and a sulfur atom means that when ring W ³ and ring W ⁴ have a substituent, the substituent does not contain a pyrrole ring structure and a sulfur atom.

Ring W ³ and ring W ⁴ are not particularly limited as long as they do not contain a pyrrole ring structure and a sulfur atom. Ring W ³ and ring W ⁴ include, for example, a piperidine ring group, an aziridine ring group, a morpholine ring group, an indoline ring group, an imidazole ring group, an imidazoline ring group, a tetrazole ring group, and an oxazoline ring group. etc. can be mentioned.

Ring W ³ and ring W ⁴ are preferably the same group.

It is preferable that ring W ³ and ring W ⁴ are each independently an indoline ring group, an imidazole ring group, or an imidazoline ring group.

Ring W ³ and ring W ⁴ may each independently have a substituent. The substituents include substituents that ring W ¹ and ring W ² described above may have.

The aromatic group represented by Ar ¹ and Ar ² includes an aromatic hydrocarbon group and an aromatic heterocyclic group.

Examples of the aromatic hydrocarbon group represented by Ar ¹ and Ar ² include aryl groups having 6 to 24 carbon atoms such as phenyl group, naphthyl group, anthracenyl group, biphenyl group, tertiary phenyl group, and phenyl tertiary phenyl group; and aralkyl groups having 7 to 24 carbon atoms, such as benzyl group, phenylethyl group, and naphthylmethyl group.

Examples of the aromatic heterocyclic group represented by Ar ¹ and Ar ² include groups containing an aromatic heterocycle having 3 to 20 carbon atoms, such as a furan ring group, a thiopyrrole ring group, an imidazole ring group, a pyridine ring group, and an oxazole ring group. there is.

The aromatic group represented by Ar ¹ and Ar ² may have a substituent. Substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine 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 12 carbon atoms, such as loethyl group and 1,1,2,2,2-pentafluoroethyl group; Alkoxy groups having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, and hexyloxy group; Alkylthio groups having 1 to 12 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, and hexylthio group; Fluorination of 1 to 12 carbon atoms such as monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, and 1,1,2,2,2-pentafluoroethoxy group. Alkoxy group; Fluorinated alkoxy groups having 1 to 12 carbon atoms, such as trifluoromethane thioalkoxy groups; An amino group that may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, and methylethyl; Carbamoyl groups in which the N-position may be substituted with an alkyl group having 1 to 6 carbon atoms, such as carbamoyl group, N-methylcarbamoyl group, and N,N-dimethylcarbamoyl group; Alkylcarbonyloxy groups having 2 to 12 carbon atoms, such as methylcarbonyloxy group and ethylcarbonyloxy group; Alkylsulfonyl groups having 1 to 12 carbon atoms, such as methylsulfonyl group and ethylsulfonyl group; Arylsulfonyl groups having 6 to 12 carbon atoms, such as phenylsulfonyl group; Alkoxysulfonyl groups having 1 to 12 carbon atoms, such as methoxysulfonyl group and ethoxysulfonyl group; Acyl groups having 2 to 12 carbon atoms, such as acetyl group and ethyl carbonyl group; aldehyde group; Alkoxycarbonyl groups having 2 to 12 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, and butyloxycarbonyl group; Alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as methoxythiocarbonyl group and ethoxythiocarbonyl group; Cyano group; nitro group; hydroxyl group; Thiol group; tongue group; Cavamo Diary; Carboxyl group; -SF ₃ ; -SF ₅ , etc.

Ar ¹ and Ar ² are preferably the same group.

Ar ¹ and Ar ² are preferably each independently an aromatic hydrocarbon group that may have a substituent.

Monovalent substituents represented by R ¹ and R ² include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; Alkoxy groups having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, and hexyloxy group; Alkylthio groups having 1 to 12 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, and hexylthio group; Fluorination of 1 to 12 carbon atoms such as monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, and 1,1,2,2,2-pentafluoroethoxy group. Alkoxy group; Fluorinated thioalkoxy groups having 1 to 12 carbon atoms, such as trifluoromethane thioalkoxy groups; An amino group that may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, and methylethyl; Carbamoyl groups in which the N-position may be substituted with an alkyl group having 1 to 6 carbon atoms, such as carbamoyl group, N-methylcarbamoyl group, and N,N-dimethylcarbamoyl group; Alkylcarbonyloxy groups having 2 to 12 carbon atoms, such as methylcarbonyloxy group and ethylcarbonyloxy group; Alkylsulfonyl groups having 1 to 12 carbon atoms, such as methylsulfonyl group and ethylsulfonyl group; Arylsulfonyl groups having 6 to 12 carbon atoms, such as phenylsulfonyl group; Alkoxysulfonyl groups having 1 to 12 carbon atoms, such as methoxysulfonyl group and ethoxysulfonyl group; Acyl groups having 2 to 12 carbon atoms, such as acetyl group and ethyl carbonyl group; aldehyde group; Alkoxycarbonyl groups having 2 to 12 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, and butyloxycarbonyl group; Alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as methoxythiocarbonyl group and ethoxythiocarbonyl group; Cyano group; nitro group; hydroxyl group; Thiol group; tongue group; Cavamo Diary; Carboxyl group; -SF ₃ ; -SF ₅ , etc.

Hydrocarbon groups represented by R ¹ and R ² include aliphatic hydrocarbon groups with 1 to 24 carbon atoms, aromatic hydrocarbon groups with 6 to 24 carbon atoms, and the like.

Aliphatic hydrocarbon groups having 1 to 24 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, and 1-methyl. Straight-chain, branched-chain, or cyclic carbon atoms having 1 to 24 carbon atoms, such as butyl group, 3-methylbutyl group, n-octyl group, n-decyl, 2-hexyl-octyl group, 4-butyloctyl group, and cyclohexyl group. Alkyl group; and unsaturated aliphatic hydrocarbon groups such as ethenyl group, propenyl group, butenyl group, pentenyl group, ethynyl group, propynyl group, allyl group, cyclohexenyl group, and butadienyl group.

Examples of 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; and aralkyl groups having 7 to 24 carbon atoms, such as benzyl group, phenylethyl group, and naphthylmethyl group.

The hydrocarbon group represented by R ¹ and R ² may have a substituent, such as a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; Alkylthio groups having 1 to 12 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, and hexylthio group; Fluorination of 1 to 12 carbon atoms such as monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, and 1,1,2,2,2-pentafluoroethoxy group. Alkoxy group; Fluorinated alkoxy groups having 1 to 12 carbon atoms, such as trifluoromethane thioalkoxy groups; An amino group that may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, and methylethyl; Carbamoyl groups in which the N-position may be substituted with an alkyl group having 1 to 6 carbon atoms, such as carbamoyl group, N-methylcarbamoyl group, and N,N-dimethylcarbamoyl group; Alkylcarbonyloxy groups having 2 to 12 carbon atoms, such as methylcarbonyloxy group and ethylcarbonyloxy group; Alkylsulfonyl groups having 1 to 12 carbon atoms, such as methylsulfonyl group and ethylsulfonyl group; Aromatic hydrocarbon groups having 6 to 25 carbon atoms, such as phenyl group, naphthyl group, and diphenyl group (preferably aryl groups having 6 to 18 hydrocarbons); Arylsulfonyl groups having 6 to 12 carbon atoms, such as phenylsulfonyl group; Alkoxysulfonyl groups having 1 to 12 carbon atoms, such as methoxysulfonyl group and ethoxysulfonyl group; Acyl groups having 2 to 12 carbon atoms, such as acetyl group and ethyl carbonyl group; aldehyde group; Alkoxycarbonyl groups having 2 to 12 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, and butyloxycarbonyl group; Alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as methoxythiocarbonyl group and ethoxythiocarbonyl group; Cyano group; nitro group; hydroxyl group; Thiol group; tongue group; Cavamo Diary; Carboxyl group; -SF ₃ ; -SF ₅ , etc.

R ¹ and R ² are preferably the same group.

R ¹ and R ² are preferably a hydrogen atom or a hydrocarbon group having 1 to 24 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 24 carbon atoms.

The cation represented by formula (I-A) is preferably a cation represented by formula (I-A-1), and the cation represented by formula (I-B) is preferably a cation represented by formula (I-B-1).

[Formula 9]

[In formula (IA-1) and formula (IB-1), ring W ³ , ring W ⁴ , Ar ¹ , Ar ² , R ¹ and R ² each have the same meaning as above.]

Examples of the cation represented by formula (I-A) include the cations described below.

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

The cation represented by formula (I-A) is formula (I-1), formula (I-2), formula (I-3), formula (I-9), formula (I-13), formula (I-17) , Formula (I-18), Formula (I-19), Formula (I-24), Formula (I-26), Formula (I-27), Formula (I-28), Formula (I-30), It is preferable that it is a cation represented by formula (I-32), formula (I-39), or formula (I-58).

Examples of the cation represented by formula (I-B) include the cations described below.

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

Cations represented by formula (I-B) are formula (I-59), formula (I-60), formula (I-61), formula (I-62), formula (I-67a), formula (I-67b) , Formula (I-68), Formula (I-69), Formula (I-78), Formula (I-79), Formula (I-84), Formula (I-85), Formula (I-89) or It is preferable that it is a cation represented by formula (I-92).

<Anion>

Compound (I) consists of at least one cation and an anion selected from the cation represented by formula (I-A) and the cation represented by formula (I-B). The combination of at least one cation and an anion selected from the cation represented by formula (I-A) and the cation represented by formula (I-B) constituting compound (I) is not limited. When the valence of the anion is 2 or more, it may have a plurality of cations represented by the formula (I-A), and may have a plurality of cations represented by the formula (I-B), and the cation represented by the formula (I-A) and the cation represented by the formula (I-B) ) may have a cation represented by . Additionally, when the valence of the anion is 2 or more, it may have cations other than the cation represented by the formula (I-A) and the cation represented by the formula (I-B).

The anion may be an organic anion or an inorganic anion.

Organic anions include, for example, acetate anions, methide anions, amide anions, sulfonate anions, or borate anions, and are preferably methide anions, amide anions, sulfonate anions, or borate anions.

The methide anion is preferably an anion represented by the formula (c-A).

[Formula 18]

[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 include a fluorine atom; Fluoroalkyl groups having 1 to 12 carbon atoms, such as monofluoromethyl group, difluoromethyl group, trifluoromethyl group, and tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as monofluorophenyl group and tetrafluorophenyl group; Cyano group; nitro group; and/or -SO ₂ -R _11c (R _11c represents a hydrocarbon group having 1 to 12 carbon atoms that may have a fluorine atom).

The amide anion is preferably an anion represented by the formula (c-B).

[Formula 19]

[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 include a fluorine atom; Fluoroalkyl groups having 1 to 12 carbon atoms, such as monofluoromethyl group, difluoromethyl group, trifluoromethyl group, and tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as monofluorophenyl group and tetrafluorophenyl group; Cyano group; nitro group; and/or -SO ₂ -R _11c (R _11c represents a hydrocarbon group having 1 to 12 carbon atoms that may have a fluorine atom).

The sulfonate anion is preferably an anion represented by the formula (c-C).

[Formula 20]

[In formula (cC), R _6c represents a monovalent substituent.]

The monovalent substituent represented by R _6c is not particularly limited, but includes a fluorine atom; Fluoroalkyl groups having 1 to 12 carbon atoms, such as monofluoromethyl group, difluoromethyl group, trifluoromethyl group, and tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as monofluorophenyl group and tetrafluorophenyl group; Cyano group; nitro group; and/or -SO ₂ -R _11c (R _11c represents a hydrocarbon group having 1 to 12 carbon atoms that may have a fluorine atom).

The borate anion is preferably an anion represented by the formula (c-D).

[Formula 21]

[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 include a fluorine atom; Fluoroalkyl groups having 1 to 12 carbon atoms, such as monofluoromethyl group, difluoromethyl group, trifluoromethyl group, and tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as monofluorophenyl group and tetrafluorophenyl group; Cyano group; nitro group; and/or -SO ₂ -R _11c (R _11c represents a hydrocarbon group having 1 to 12 carbon atoms that may have a fluorine atom).

The anion represented by formula (c-A) is preferably an anion represented by formula (c-A1),

The anion represented by formula (c-B) is preferably an anion represented by formula (c-B1),

The anion represented by the formula (c-C) is preferably an anion represented by the formula (c-C1),

The anion represented by the formula (c-D) is preferably an anion represented by the formula (c-D1) or an anion represented by the formula (c-D2).

[Formula 22]

[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 fluoroalkyl group having 1 to 12 carbon atoms. n1 to n4 each independently represent an integer from 0 to 5.]

Organic anions include, for example, acetate anion [CH ₃ COO ^- ], trifluoroacetate anion [CF ₃ COO ^- ], methane sulfonate anion [CH ₃ SO ₃ ^- ], and trifluoromethane sulfonate 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 ^- ], tris(tris) Fluoromethanesulfonyl) methanide anion [(CF ₃ SO ₂ ) ₃ C ^- ], dimethylphosphinate anion [(CH ₃ ) ₂ POO ^- ], perfluorobutane sulfonate 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 ^- 〕, (trifluoromethane Sulfonyl)(trifluoromethanecarbonyl)imide anion [(CF ₃ SO ₂ )(CF ₃ CO)N ^- ], perfluoropropane-1,3-disulfonate anion [ ^- O ₃ S (CF) ₂ ) ₃ SO ₃ ^- ], tetrakisaryl borate anion (tetrakisphenyl borate, tetrakis (pentafluorophenyl) borate), tetracyanoborate, tris (pentafluoroethyl) trifluorophosphate [P ^- ( C ₂ F ₅ ) ₃ F ₃ ], etc.

Inorganic anions include, for example, fluoride anion, chloride anion, bromide anion, iodide anion, tetrachloroaluminate anion [AlCl ₄ ^- ], heptachlorodialluminate anion [Al ₂ Cl ₇ ^- ], and tetrafluoroborate. Anion [BF ₄ ^- ], hexafluorophosphate anion [PF ₆ ^- ], perchlorate anion [ClO ₄ ^- ], nitrate anion [NO ₃ ^- ], hexafluoroarsenate anion [AsF ₆ ^- ], hexafluoro Roantimonate anion [SbF ₆ ^- ], hexafluoroniobate anion [NbF ₆ ^- ], hexafluorotantalate anion [TaF ₆ ^- ], dicyanamide anion [(CN) ₂ N ^- ], bis( Fluorosulfonyl)imide anion (N ^- (SO ₂ F) ₂ ), (poly)hydrofluorofluoride anion [F(HF)m ^- ] (m is about 1 or more and 3 or less), thiocyanine anion [ SCN ^- ], carbonate anion [CO ₃ ^2- ], etc. can be mentioned.

The inorganic anion is preferably bis(fluorosulfonyl)imide anion (N ^- (SO ₂ F) ₂ ). Organic anions include trifluoroacetate anion [CF ₃ COO ^- ], trifluoromethane sulfonate anion [CF ₃ SO ₃ ^- ], and bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ). ₂ N ^- ], tris (trifluoromethanesulfonyl) methanide anion [(CF ₃ SO ₂ ) ₃ C ^- ], perfluorobutanesulfonate anion [C ₄ F ₉ SO ₃ ^- ], bis (pentafluor Roethanesulfonyl) imide anion [(C ₂ F ₅ SO ₂ ) ₂ N ^- ], perfluorobutanoate anion [C ₃ F ₇ COO ^- ], (trifluoromethanesulfonyl) (trifluoro Methanecarbonyl)imide anion [(CF ₃ SO ₂ )(CF ₃ CO)N ^- ], perfluoropropane-1,3-disulfonate anion [ ^- O ₃ S(CF ₂ ) ₃ SO ₃ ^- 〕 , tetrakisaryl borate anion (tetrakisphenyl borate, tetrakis (pentafluorophenyl) borate), tetracyanoborate are preferred, and more 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, especially preferred. It is 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 containing a cation represented by formula (I-1) and a chloride anion, and is a compound shown below.

[Formula 23]

number cation negative ion Compound (1) Equation (I-1) Cl ^- Compound (2) Equation (I-2) Cl ^- Compound (3) Equation (I-3) Cl ^- Compound (4) Equation (I-9) Cl ^- Compound (5) Equation (I-13) Cl ^- Compound (6) Equation (I-17) Cl ^- Compound (7) Equation (I-18) Cl ^- Compound (8) Equation (I-19) Cl ^- Compound (9) Equation (I-24) Cl ^- Compound (10) Equation (I-26) Cl ^- Compound (11) Equation (I-27) Cl ^- Compound (12) Equation (I-28) Cl ^- Compound (13) Equation (I-30) Cl ^- Compound (14) Equation (I-32) Cl ^- Compound (15) Equation (I-39) Cl ^- Compound (16) Equation (I-58) Cl ^- Compound (17) Equation (I-59) Cl ^- Compound (18) Equation (I-60) Cl ^- Compound (19) Equation (I-61) Cl ^- Compound (20) Equation (I-62) Cl ^- Compound (21a) Formula (I-67a) Cl ^- Compound (21b) Formula (I-67b) Cl ^- Compound (22) Equation (I-68) Cl ^- Compound (23) Equation (I-69) Cl ^- Compound (24) Equation (I-78) Cl ^- Compound (25) Equation (I-79) Cl ^- Compound (26) Equation (I-84) Cl ^- Compound (27) Equation (I-85) Cl ^- Compound (28) Equation (I-89) Cl ^- Compound (29) Equation (I-92) Cl ^-

number cation negative ion Compound (30) Equation (I-1) (FSO ₂ ) ₂ N ^- Compound (31) Equation (I-2) (FSO ₂ ) ₂ N ^- Compound (32) Equation (I-3) (FSO ₂ ) ₂ N ^- Compound (33) Equation (I-9) (FSO ₂ ) ₂ N ^- Compound (34) Equation (I-13) (FSO ₂ ) ₂ N ^- Compound (35) Equation (I-17) (FSO ₂ ) ₂ N ^- Compound (36) Equation (I-18) (FSO ₂ ) ₂ N ^- Compound (37) Equation (I-19) (FSO ₂ ) ₂ N ^- Compound (38) Equation (I-24) (FSO ₂ ) ₂ N ^- Compound(39) Equation (I-26) (FSO ₂ ) ₂ N ^- Compound (40) Equation (I-27) (FSO ₂ ) ₂ N ^- Compound (41) Equation (I-28) (FSO ₂ ) ₂ N ^- Compound (42) Equation (I-30) (FSO ₂ ) ₂ N ^- Compound (43) Equation (I-32) (FSO ₂ ) ₂ N ^- Compound (44) Equation (I-39) (FSO ₂ ) ₂ N ^- Compound (45) Equation (I-58) (FSO ₂ ) ₂ N ^- Compound (46) Equation (I-59) (FSO ₂ ) ₂ N ^- Compound (47) Equation (I-60) (FSO ₂ ) ₂ N ^- Compound(48) Equation (I-61) (FSO ₂ ) ₂ N ^- Compound(49) Equation (I-62) (FSO ₂ ) ₂ N ^- Compound (50a) Formula (I-67a) (FSO ₂ ) ₂ N ^- Compound (50b) Formula (I-67b) (FSO ₂ ) ₂ N ^- Compound (51) Equation (I-68) (FSO ₂ ) ₂ N ^- Compound (52) Equation (I-69) (FSO ₂ ) ₂ N ^- Compound (53) Equation (I-78) (FSO ₂ ) ₂ N ^- Compound (54) Equation (I-79) (FSO ₂ ) ₂ N ^- Compound(55) Equation (I-84) (FSO ₂ ) ₂ N ^- Compound (56) Equation (I-85) (FSO ₂ ) ₂ N ^- Compound (57) Equation (I-89) (FSO ₂ ) ₂ N ^- Compound(58) Equation (I-92) (FSO ₂ ) ₂ N ^-

number cation negative ion Compound(59) Equation (I-1) C F ₃ S O ₃ ^- Compound (60) Equation (I-2) C F ₃ S O ₃ ^- Compound(61) Equation (I-3) C F ₃ S O ₃ ^- Compound (62) Equation (I-9) C F ₃ S O ₃ ^- Compound (63) Equation (I-13) C F ₃ S O ₃ ^- Compound(64) Equation (I-17) C F ₃ S O ₃ ^- Compound (65) Equation (I-18) C F ₃ S O ₃ ^- Compound(66) Equation (I-19) C F ₃ S O ₃ ^- Compound(67) Equation (I-24) C F ₃ S O ₃ ^- Compound(68) Equation (I-26) C F ₃ S O ₃ ^- Compound(69) Equation (I-27) C F ₃ S O ₃ ^- Compound (70) Equation (I-28) C F ₃ S O ₃ ^- Compound(71) Equation (I-30) C F ₃ S O ₃ ^- Compound (72) Equation (I-32) C F ₃ S O ₃ ^- Compound (73) Equation (I-39) C F ₃ S O ₃ ^- Compound(74) Equation (I-58) C F ₃ S O ₃ ^- Compound(75) Equation (I-59) C F ₃ S O ₃ ^- Compound (76) Equation (I-60) C F ₃ S O ₃ ^- Compound(77) Equation (I-61) C F ₃ S O ₃ ^- Compound (78) Equation (I-62) C F ₃ S O ₃ ^- Compound (79a) Formula (I-67a) C F ₃ S O ₃ ^- Compound (79b) Formula (I-67b) C F ₃ S O ₃ ^- Compound(80) Equation (I-68) C F ₃ S O ₃ ^- Compound(81) Equation (I-69) C F ₃ S O ₃ ^- Compound(82) Equation (I-78) C F ₃ S O ₃ ^- Compound(83) Equation (I-79) C F ₃ S O ₃ ^- Compound(84) Equation (I-84) C F ₃ S O ₃ ^- Compound(85) Equation (I-85) C F ₃ S O ₃ ^- Compound(86) Equation (I-89) C F ₃ S O ₃ ^- Compound (87) Equation (I-92) C F ₃ S O ₃ ^-

number cation negative ion Compound(88) Equation (I-1) (CF ₃ SO ₂ ) ₂ N ^- Compound(89) Equation (I-2) (CF ₃ SO ₂ ) ₂ N ^- Compound (90) Equation (I-3) (CF ₃ SO ₂ ) ₂ N ^- Compound(91) Equation (I-9) (CF ₃ SO ₂ ) ₂ N ^- Compound (92) Equation (I-13) (CF ₃ SO ₂ ) ₂ N ^- Compound (93) Equation (I-17) (CF ₃ SO ₂ ) ₂ N ^- Compound(94) Equation (I-18) (CF ₃ SO ₂ ) ₂ N ^- Compound(95) Equation (I-19) (CF ₃ SO ₂ ) ₂ N ^- Compound(96) Equation (I-24) (CF ₃ SO ₂ ) ₂ N ^- Compound (97) Equation (I-26) (CF ₃ SO ₂ ) ₂ N ^- Compound(98) Equation (I-27) (CF ₃ SO ₂ ) ₂ N ^- Compound(99) Equation (I-28) (CF ₃ SO ₂ ) ₂ N ^- Compound (100) Equation (I-30) (CF ₃ SO ₂ ) ₂ N ^- Compound (101) Equation (I-32) (CF ₃ SO ₂ ) ₂ N ^- Compound (102) Equation (I-39) (CF ₃ SO ₂ ) ₂ N ^- Compound (103) Equation (I-58) (CF ₃ SO ₂ ) ₂ N ^- Compound (104) Equation (I-59) (CF ₃ SO ₂ ) ₂ N ^- Compound (105) Equation (I-60) (CF ₃ SO ₂ ) ₂ N ^- Compound (106) Equation (I-61) (CF ₃ SO ₂ ) ₂ N ^- Compound (107) Equation (I-62) (CF ₃ SO ₂ ) ₂ N ^- Compound (108a) Formula (I-67a) (CF ₃ SO ₂ ) ₂ N ^- Compound (108b) Formula (I-67b) (CF ₃ SO ₂ ) ₂ N ^- Compound (109) Equation (I-68) (CF ₃ SO ₂ ) ₂ N ^- Compound (110) Equation (I-69) (CF ₃ SO ₂ ) ₂ N ^- Compound (111) Equation (I-78) (CF ₃ SO ₂ ) ₂ N ^- Compound (112) Equation (I-79) (CF ₃ SO ₂ ) ₂ N ^- Compound (113) Equation (I-84) (CF ₃ SO ₂ ) ₂ N ^- Compound (114) Equation (I-85) (CF ₃ SO ₂ ) ₂ N ^- Compound (115) Equation (I-89) (CF ₃ SO ₂ ) ₂ N ^- Compound (116) Equation (I-92) (CF ₃ SO ₂ ) ₂ N ^-

number cation negative ion Compound (117) Equation (I-1) (CF ₃ SO ₂ ) ₃ C ^- Compound (118) Equation (I-2) (CF ₃ SO ₂ ) ₃ C ^- Compound (119) Equation (I-3) (CF ₃ SO ₂ ) ₃ C ^- Compound (120) Equation (I-9) (CF ₃ SO ₂ ) ₃ C ^- Compound (121) Equation (I-13) (CF ₃ SO ₂ ) ₃ C ^- Compound (122) Equation (I-17) (CF ₃ SO ₂ ) ₃ C ^- Compound (123) Equation (I-18) (CF ₃ SO ₂ ) ₃ C ^- Compound (124) Equation (I-19) (CF ₃ SO ₂ ) ₃ C ^- Compound (125) Equation (I-24) (CF ₃ SO ₂ ) ₃ C ^- Compound (126) Equation (I-26) (CF ₃ SO ₂ ) ₃ C ^- Compound (127) Equation (I-27) (CF ₃ SO ₂ ) ₃ C ^- Compound (128) Equation (I-28) (CF ₃ SO ₂ ) ₃ C ^- Compound (129) Equation (I-30) (CF ₃ SO ₂ ) ₃ C ^- Compound (130) Equation (I-32) (CF ₃ SO ₂ ) ₃ C ^- Compound (131) Equation (I-39) (CF ₃ SO ₂ ) ₃ C ^- Compound (132) Equation (I-58) (CF ₃ SO ₂ ) ₃ C ^- Compound (133) Equation (I-59) (CF ₃ SO ₂ ) ₃ C ^- Compound (134) Equation (I-60) (CF ₃ SO ₂ ) ₃ C ^- Compound (135) Equation (I-61) (CF ₃ SO ₂ ) ₃ C ^- Compound (136) Equation (I-62) (CF ₃ SO ₂ ) ₃ C ^- Compound (137a) Formula (I-67a) (CF ₃ SO ₂ ) ₃ C ^- Compound (137b) Formula (I-67b) (CF ₃ SO ₂ ) ₃ C ^- Compound (138) Equation (I-68) (CF ₃ SO ₂ ) ₃ C ^- Compound (139) Equation (I-69) (CF ₃ SO ₂ ) ₃ C ^- Compound (140) Equation (I-78) (CF ₃ SO ₂ ) ₃ C ^- Compound (141) Equation (I-79) (CF ₃ SO ₂ ) ₃ C ^- Compound (142) Equation (I-84) (CF ₃ SO ₂ ) ₃ C ^- Compound (143) Equation (I-85) (CF ₃ SO ₂ ) ₃ C ^- Compound (144) Equation (I-89) (CF ₃ SO ₂ ) ₃ C ^- Compound (145) Equation (I-92) (CF ₃ SO ₂ ) ₃ C ^-

number cation negative ion Compound (146) Equation (I-1) (CN) ₄ B ^- Compound (147) Equation (I-2) (CN) ₄ B ^- Compound (148) Equation (I-3) (CN) ₄ B ^- Compound (149) Equation (I-9) (CN) ₄ B ^- Compound (150) Equation (I-13) (CN) ₄ B ^- Compound (151) Equation (I-17) (CN) ₄ B ^- Compound (152) Equation (I-18) (CN) ₄ B ^- Compound (153) Equation (I-19) (CN) ₄ B ^- Compound (154) Equation (I-24) (CN) ₄ B ^- Compound (155) Equation (I-26) (CN) ₄ B ^- Compound (156) Equation (I-27) (CN) ₄ B ^- Compound (157) Equation (I-28) (CN) ₄ B ^- Compound(158) Equation (I-30) (CN) ₄ B ^- Compound (159) Equation (I-32) (CN) ₄ B ^- Compound (160) Equation (I-39) (CN) ₄ B ^- Compound (161) Equation (I-58) (CN) ₄ B ^- Compound (162) Equation (I-59) (CN) ₄ B ^- Compound (163) Equation (I-60) (CN) ₄ B ^- Compound (164) Equation (I-61) (CN) ₄ B ^- Compound(165) Equation (I-62) (CN) ₄ B ^- Compound (166a) Formula (I-67a) (CN) ₄ B ^- Compound (166b) Formula (I-67b) (CN) ₄ B ^- Compound(167) Equation (I-68) (CN) ₄ B ^- Compound(168) Equation (I-69) (CN) ₄ B ^- Compound(169) Equation (I-78) (CN) ₄ B ^- Compound (170) Equation (I-79) (CN) ₄ B ^- Compound (171) Equation (I-84) (CN) ₄ B ^- Compound (172) Equation (I-85) (CN) ₄ B ^- Compound(173) Equation (I-89) (CN) ₄ B ^- Compound (174) Equation (I-92) (CN) ₄ B ^-

number cation negative ion Compound(175) Equation (I-1) (C ₆ H ₅ ) ₄ B ^- Compound(176) Equation (I-2) (C ₆ H ₅ ) ₄ B ^- Compound(177) Equation (I-3) (C ₆ H ₅ ) ₄ B ^- Compound(178) Equation (I-9) (C ₆ H ₅ ) ₄ B ^- Compound (179) Equation (I-13) (C ₆ H ₅ ) ₄ B ^- Compound (180) Equation (I-17) (C ₆ H ₅ ) ₄ B ^- Compound (181) Equation (I-18) (C ₆ H ₅ ) ₄ B ^- Compound (182) Equation (I-19) (C ₆ H ₅ ) ₄ B ^- Compound (183) Equation (I-24) (C ₆ H ₅ ) ₄ B ^- Compound (184) Equation (I-26) (C ₆ H ₅ ) ₄ B ^- Compound (185) Equation (I-27) (C ₆ H ₅ ) ₄ B ^- Compound (186) Equation (I-28) (C ₆ H ₅ ) ₄ B ^- Compound (187) Equation (I-30) (C ₆ H ₅ ) ₄ B ^- Compound (188) Equation (I-32) (C ₆ H ₅ ) ₄ B ^- Compound (189) Equation (I-39) (C ₆ H ₅ ) ₄ B ^- Compound (190) Equation (I-58) (C ₆ H ₅ ) ₄ B ^- Compound (191) Equation (I-59) (C ₆ H ₅ ) ₄ B ^- Compound (192) Equation (I-60) (C ₆ H ₅ ) ₄ B ^- Compound (193) Equation (I-61) (C ₆ H ₅ ) ₄ B ^- Compound (194) Equation (I-62) (C ₆ H ₅ ) ₄ B ^- Compound (195a) Formula (I-67a) (C ₆ H ₅ ) ₄ B ^- Compound (195b) Formula (I-67b) (C ₆ H ₅ ) ₄ B ^- Compound (196) Equation (I-68) (C ₆ H ₅ ) ₄ B ^- Compound (197) Equation (I-69) (C ₆ H ₅ ) ₄ B ^- Compound (198) Equation (I-78) (C ₆ H ₅ ) ₄ B ^- Compound (199) Equation (I-79) (C ₆ H ₅ ) ₄ B ^- Compound (200) Equation (I-84) (C ₆ H ₅ ) ₄ B ^- Compound (201) Equation (I-85) (C ₆ H ₅ ) ₄ B ^- Compound (202) Equation (I-89) (C ₆ H ₅ ) ₄ B ^- Compound (203) Equation (I-92) (C ₆ H ₅ ) ₄ B ^-

number cation negative ion Compound (204) Equation (I-1) (C ₆ F ₅ ) ₄ B ^- Compound (205) Equation (I-2) (C ₆ F ₅ ) ₄ B ^- Compound (206) Equation (I-3) (C ₆ F ₅ ) ₄ B ^- Compound (207) Equation (I-9) (C ₆ F ₅ ) ₄ B ^- Compound (208) Equation (I-13) (C ₆ F ₅ ) ₄ B ^- Compound (209) Equation (I-17) (C ₆ F ₅ ) ₄ B ^- Compound (210) Equation (I-18) (C ₆ F ₅ ) ₄ B ^- Compound (211) Equation (I-19) (C ₆ F ₅ ) ₄ B ^- Compound(212) Equation (I-24) (C ₆ F ₅ ) ₄ B ^- Compound(213) Equation (I-26) (C ₆ F ₅ ) ₄ B ^- Compound (214) Equation (I-27) (C ₆ F ₅ ) ₄ B ^- Compound(215) Equation (I-28) (C ₆ F ₅ ) ₄ B ^- Compound(216) Equation (I-30) (C ₆ F ₅ ) ₄ B ^- Compound(217) Equation (I-32) (C ₆ F ₅ ) ₄ B ^- Compound(218) Equation (I-39) (C ₆ F ₅ ) ₄ B ^- Compound(219) Equation (I-58) (C ₆ F ₅ ) ₄ B ^- Compound (220) Equation (I-59) (C ₆ F ₅ ) ₄ B ^- Compound(221) Equation (I-60) (C ₆ F ₅ ) ₄ B ^- Compound(222) Equation (I-61) (C ₆ F ₅ ) ₄ B ^- Compound(223) Equation (I-62) (C ₆ F ₅ ) ₄ B ^- Compound (224a) Formula (I-67a) (C ₆ F ₅ ) ₄ B ^- Compound (224b) Formula (I-67b) (C ₆ F ₅ ) ₄ B ^- Compound (225) Equation (I-68) (C ₆ F ₅ ) ₄ B ^- Compound (226) Equation (I-69) (C ₆ F ₅ ) ₄ B ^- Compound(227) Equation (I-78) (C ₆ F ₅ ) ₄ B ^- Compound(228) Equation (I-79) (C ₆ F ₅ ) ₄ B ^- Compound(229) Equation (I-84) (C ₆ F ₅ ) ₄ B ^- Compound (230) Equation (I-85) (C ₆ F ₅ ) ₄ B ^- Compound(231) Equation (I-89) (C ₆ F ₅ ) ₄ B ^- Compound (232) Equation (I-92) (C ₆ F ₅ ) ₄ B ^-

Compound (I) includes compound (3), compound (5), compound (8), compound (20), compound (24), compound (33), compound (34), compound (36), compound (37), Compound (42), Compound (48), Compound (49), Compound (50a), Compound (50b), Compound (52), Compound (53), Compound (91), Compound (92), Compound (94), Compound (95), Compound (100), Compound (106), Compound (107), Compound (108a), Compound (108b), Compound (110), Compound (120), Compound (121), Compound (123), Compound (124), Compound (129), Compound (135), Compound (136), Compound (137a), Compound (137b), Compound (139), Compound (140), Compound (149), Compound (150), Compound (152), Compound (153), Compound (158), Compound (164), Compound (166a), Compound (166b), Compound (168), Compound (169), Compound (178), Compound (179), Compound (181), Compound (182), Compound (187), Compound (193), Compound (194), Compound (195a), Compound (195b), Compound (197), Compound (198), Compound (206), Compound (207), Compound (208), Compound (210), Compound (211), Compound (216), Compound (222), Compound (223), Compound (224a), Compound (224b), Compound (226), Compound (227) is preferred.

<Method for producing Compound (I)>

The cation represented by formula (I-A), which is the cation in compound (I), is the compound represented by formula (M) (hereinafter sometimes referred to as compound (M)) and the compound represented by formula (b-1) ( It can be produced by reacting (hereinafter sometimes referred to as compound (b-1)) with a compound represented by formula (b-2) (hereinafter sometimes referred to as compound (b-2)).

[Formula 24]

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

The reaction between compound (M), compound (b-1), and compound (b-2) is preferably carried out in the presence of a catalyst.

Catalysts include carboxylic acids such as formic acid, acetic acid, and trifluoroacetic acid; ammonium chloride; Lewis acids such as titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride, and lanthanoid triflate; Sulfonic acid anhydrides such as methanesulfonic acid anhydride, p-toluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, and nonafluorobutanesulfonic acid anhydride; Sulfonic acids such as paratoluenesulfonic acid, trifluoromethanesulfonic acid, and fluorosulfuric acid; Electrophilic alkylating agents such as dimethyl sulfate, methyl triflate, iodomethane, trimethyloxonium tetrafluoroborate, and dimethyl fluorosulfate; Sulfonic acid halides such as paratoluenesulfonyl chloride and trifluoromethanesulfonyl chloride; bismuth nitrate; Carboxylate salts such as ammonium formate and ammonium acetate can be mentioned.

The amount of catalyst used is usually 0.0001 to 100 mole, preferably 0.1 to 10 mole, per 1 mole 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.

Bases include metals such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tertiary butoxide, and potassium tertiary butoxide. alkoxides (preferably alkali metal alkoxides), etc.; Metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride, and sodium borohydride; metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, lithium carbonate, lithium bicarbonate, and cesium carbonate; Organic lithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, and phenyllithium; Alkyl metal halides such as methyl magnesium bromide, isopropyl magnesium bromide, n-butyl magnesium bromide, and isopropyl magnesium chloride; Metal amide compounds such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, and lithium tetramethylpiperidide; Pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, p Amine compounds such as ferridine, pyrrolidine, proline, aniline, N,N-dimethylaniline, and ethylenediamine; Metal carboxylates such as sodium acetate, potassium acetate, and sodium formate; Ammonium carboxylate salts such as ammonium acetate; etc. can be mentioned.

The amount of base used is usually 0.01 to 100 mol, preferably 0.1 to 10 mol, per 1 mol of compound (M).

The reaction of compound (M), compound (b-1), and compound (b-2) can be carried out in the presence of a solvent.

Solvents include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents of benzene, toluene, xylene, and anisole; Aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, and methylcyclohexane; Halogen-based solvents such as chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; Ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and normal propyl acetate; alcohol solvents such as methanol, ethanol, isopropanol, hexafluoroisopropanol, n-butanol, isobutanol, and tert-butanol; Ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; Tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentylmethyl ether, 4-methyltetrahydropyran, dioxane, diethyl ether, tert-butylmethyl ether, diisopropyl ether, dimethoxyethane, diethoxymethane, etc. ether solvent; Amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; hexamethyl phosphate triamide; Water, etc. may be mentioned. The solvent is preferably a nitrile solvent, an aromatic hydrocarbon solvent, an alcohol solvent, or a ketone solvent, and is more preferably acetonitrile, toluene, methanol, ethanol, methyl ethyl ketone, or methyl isobutyl ketone.

The amount of solvent used is usually 0.1 to 100 parts by mass, preferably 1 to 50 parts by mass, per 1 part by mass of compound (M).

The reaction between compound (M), compound (b-1), and compound (b-2) is carried out by mixing compound (M), compound (b-1), and compound (b-2).

For the reaction of compound (M), compound (b-1), and compound (b-2), it is preferable to add compound (b-1) and compound (b-2) to a mixture of compound (M), base, and catalyst. .

The reaction of compound (M), compound (b-1), and compound (b-2) is preferably carried out under a nitrogen atmosphere.

The amount of compound (b-1) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (M).

The amount of compound (b-2) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (M).

The reaction time of compound (M), compound (b-1), and compound (b-2) is usually 0.01 to 100 hours.

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

Compound (b-1) and compound (b-2) include, for example, indoline, methylindoline, nitroindoline, aminobiphenyl, cyanoaminobiphenyl (such as 4-amino-4'-cyanobiphenyl), and diphenyl. Examples include phenylaniline (4-(3,5-diphenylphenyl)aniline, etc.), pyrrolidine, piperidine, morpholine, imidazole, and triazole.

Compound (M) includes 4,4a,5,6-tetrahydro-7-hydroxy-2(3H)-naphthalenone.

Additionally, the reaction between compound (M), compound (b-1), and compound (b-2) can be carried out stepwise. For example, compound (M) and compound (b-2) are reacted to obtain a compound represented by the formula (M-A) (hereinafter sometimes referred to as compound (M-A)), and the obtained compound (M-A) and compound (b-1) are obtained. ) can be reacted to obtain a cation represented by formula (I-A).

[Formula 25]

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

The reaction between compound (M) and compound (b-2) is carried out by mixing compound (M) and compound (b-2).

The reaction between compound (M) and compound (b-2) is preferably carried out under a nitrogen atmosphere.

The reaction between compound (M) and compound (b-2) can be performed in the presence of a solvent. Solvents include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents of benzene, toluene, xylene, and anisole; Aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, and methylcyclohexane; Halogen-based solvents such as chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; Ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and normal propyl acetate; alcohol solvents such as methanol, ethanol, isopropanol, hexafluoroisopropanol, n-butanol, isobutanol, and tert-butanol; Ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; Tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentylmethyl ether, 4-methyltetrahydropyran, dioxane, diethyl ether, tert-butylmethyl ether, diisopropyl ether, dimethoxyethane, diethoxymethane, etc. ether solvent; Amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; hexamethyl phosphate triamide; Water, etc. may be mentioned. The solvent is preferably a nitrile solvent, an aromatic hydrocarbon solvent, an alcohol solvent, or a ketone solvent, and more preferably acetonitrile, toluene, methanol, ethanol, methyl ethyl ketone, or methyl isobutyl ketone.

The amount of solvent used is usually 0.1 to 100 parts by mass, preferably 1 to 50 parts by mass, per 1 part by mass of compound (M).

The amount of compound (b-2) used is usually 0.1 to 10 mole, preferably 0.5 to 5 mole, per 1 mole equivalent of compound (M).

The reaction time between compound (M) and compound (b-2) is usually 0.01 to 100 hours.

The reaction temperature between compound (M) and compound (b-2) is usually -100 to 150°C.

The reaction between compound (M-A) and compound (b-1) is carried out by mixing compound (M-A) and compound (b-1). The reaction between compound (M-A) and compound (b-1) is preferably carried out in the presence of a catalyst.

Catalysts include carboxylic acids such as formic acid, acetic acid, and trifluoroacetic acid; ammonium chloride; Lewis acids such as titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride, and lanthanoid triflate; Sulfonic acid anhydrides such as methanesulfonic acid anhydride, p-toluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, and nonafluorobutanesulfonic acid anhydride; Sulfonic acids such as paratoluenesulfonic acid, trifluoromethanesulfonic acid, and fluorosulfuric acid; Electrophilic alkylating agents such as dimethyl sulfate, methyl triflate, iodomethane, trimethyloxonium tetrafluoroborate, and dimethyl fluorosulfate; Sulfonic acid halides such as paratoluenesulfonyl chloride and trifluoromethanesulfonyl chloride; Carboxylate salts such as ammonium formate and ammonium acetate can be mentioned.

The amount of catalyst used is usually 0.0001 to 100 mole, preferably 0.1 to 10 mole, per 1 mole equivalent of compound (M-A).

The reaction between compound (M-A) and compound (b-1) is preferably carried out in the presence of a base.

Bases include metals such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tertiary butoxide, and potassium tertiary butoxide. alkoxides (preferably alkali metal alkoxides), etc.; Metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride, and sodium borohydride; metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, lithium carbonate, lithium bicarbonate, and cesium carbonate; Organic lithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, and phenyllithium; Alkyl metal halides such as methyl magnesium bromide, isopropyl magnesium bromide, n-butyl magnesium bromide, and isopropyl magnesium chloride; Metal amide compounds such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, and lithium tetramethylpiperidide; Pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, p Amine compounds such as ferridine, pyrrolidine, proline, aniline, N,N-dimethylaniline, and ethylenediamine; Metal carboxylates such as sodium acetate, potassium acetate, and sodium formate; Ammonium carboxylate salts such as ammonium acetate; etc. can be mentioned.

The amount of base used is usually 0.0001 to 100 mol, preferably 0.1 to 10 mol, per 1 mol of compound (M-A).

The reaction between compound (M-A) and compound (b-1) can be performed in the presence of a solvent.

Solvents include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents of benzene, toluene, xylene, and anisole; Aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, and methylcyclohexane; Halogen-based solvents such as chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; Ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and normal propyl acetate; alcohol solvents such as methanol, ethanol, isopropanol, hexafluoroisopropanol, n-butanol, isobutanol, and tert-butanol; Ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; Tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentylmethyl ether, 4-methyltetrahydropyran, dioxane, diethyl ether, tert-butylmethyl ether, diisopropyl ether, dimethoxyethane, diethoxymethane, etc. ether solvent; Amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; hexamethyl phosphate triamide; Water, etc. may be mentioned. The solvent is preferably a nitrile solvent, an aromatic hydrocarbon solvent, an alcohol solvent, or a ketone solvent, and is more preferably acetonitrile, toluene, methanol, ethanol, methyl ethyl ketone, or methyl isobutyl ketone.

The amount of solvent used is usually 0.1 to 100 parts by mass, preferably 1 to 50 parts by mass, per 1 part by mass of compound (M-A).

The amount of compound (b-1) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (M-A).

The reaction time between compound (M-A) and compound (b-1) is usually 0.01 to 100 hours. The reaction temperature between compound (M-A) and compound (b-1) is usually -100 to 150°C.

Examples of the compound (M-A) include the compounds described below.

[Formula 26]

[Formula 27]

The cation represented by formula (I-B) is compound (M), the compound represented by formula (b-3) (hereinafter sometimes referred to as compound (b-3)), and the compound represented by formula (b-4). It can be produced by reacting (hereinafter sometimes referred to as compound (b-4)).

[Formula 28]

[In the formula, ring W ¹ , ring W ² , Ar ¹ , Ar ² , R ¹ and R ² each have the same meaning as above.]

The reaction of compound (M), compound (b-3), and compound (b-4) is preferably carried out in the presence of a catalyst.

Catalysts include the same catalysts that can be used for the reaction of compound (M), compound (b-1), and compound (b-2).

The amount of catalyst used is usually 0.0001 to 100 mole, preferably 0.1 to 10 mole, per 1 mole of compound (M).

The reaction of compound (M), compound (b-3), and compound (b-4) is preferably carried out in the presence of a base.

Examples of the base include the same bases that can be used in the reaction of compound (M), compound (b-1), and compound (b-2).

The amount of base used is usually 0.0001 to 100 mol, preferably 0.1 to 10 mol, per 1 mol of compound (M).

The reaction between compound (M), compound (b-3), and compound (b-4) is carried out by mixing compound (M), compound (b-3), and compound (b-4). Mixing compound (M), compound (b-3), and compound (b-4) is mixing the catalyst, compound (b-3), and compound (b-4) with the mixture of compound (M) and base. It is preferable, and it is more preferable to mix compound (b-3) and compound (b-4) with the mixture obtained by adding a catalyst to the mixture of compound (M) and a base.

The amount of compound (b-3) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (M).

The amount of compound (b-4) used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of compound (M).

The reaction time of compound (M), compound (b-3), and compound (b-4) is usually 0.1 to 100 hours.

The reaction temperature of compound (M), compound (b-3), and compound (b-4) is usually -100 to 150°C.

When the anion of Compound (I) is to be exchanged for a desired anion, ion exchange can be performed by mixing Compound (I) with a salt containing the desired anion. The ion exchange can be performed in the presence of a solvent. Salts containing the desired anion include, for example, lithium salts, sodium salts, potassium salts, cesium salts, barium salts, calcium salts, magnesium salts, and ammonium salts.

<Composition containing compound (I)>

The present invention also includes compositions containing compound (I).

The composition containing compound (I) can be used for all purposes, but it can be particularly suitably used for applications that may be exposed to light including sunlight or ultraviolet rays. Specific examples include, for example, glass substitutes and their surface coatings; Coatings for window glass, skylight glass, and light source protection glass for residences, facilities, transportation equipment, etc.; Window films for residences, facilities, transportation equipment, etc.; Interior and exterior materials and interior and exterior paints for housing, facilities, transportation equipment, etc., and coating films formed by the paints; Alkyd resin lacquer paints and coating films formed by the paints; Acrylic lacquer paint and the coating film formed by the paint; Members for light sources that emit ultraviolet rays, such as fluorescent lamps and mercury lamps; Materials for blocking electromagnetic waves generated from precision machinery, electronic and electrical equipment members, and various displays; Containers or packaging materials for food, chemicals, drugs, etc.; Bottles, boxes, blisters, cups, special packaging, compact disc coats, agricultural and industrial sheet or film materials; Anti-fade agents for printed materials, dyes, dyes, pigments, etc.; Protective films for polymer supports (e.g. for plastic parts such as machinery and automobile parts); printed overcoat; inkjet media film; laminated mat; optical light film; Interlayer of safety glass and windshield; Electrochromic or photochromic applications; Overlaminate film; solar control membrane; Cosmetics such as sunscreen cream, shampoo, conditioner, and hair conditioner; Textile products and textiles for clothing such as sportswear, stockings, hats, etc.; Household interior items such as curtains, carpets, wallpaper, etc.; Medical devices such as plastic lenses, contact lenses, artificial eyes, etc.; Optical supplies such as optical filters, backlight display films, prisms, mirrors, photographic materials, etc.; Stationery products such as mold films, transfer stickers, anti-graffiti films, tapes, and ink; Examples include display boards, indicators, etc., and their surface coating materials.

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 referred to as “composition”). (1) It is preferable that it is sometimes referred to as “(1)”.

Resins used in the resin composition include thermoplastic resins and thermosetting resins that have been conventionally used in the production of various known molded bodies, sheets, films, etc.

Thermoplastic resins include, for example, olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin, poly(meth)acrylic acid ester resin, polystyrene resin, styrene-acrylonitrile resin, and acrylonitrile-butadiene-styrene. -based resin, polyvinyl chloride-based resin, polyvinylidene chloride-based resin, polyvinyl acetate-based resin, polyvinyl butyral-based resin, ethylene-vinyl acetate-based copolymer, ethylene vinyl alcohol-based resin, polyethylene terephthalate resin, polybutylene Examples include polyester resins such as terephthalate resin and liquid crystal polyester resin, polyacetal resin, polyamide resin, polycarbonate resin, polyurethane resin, and polyphenylene sulfide resin. These resins can also be used as a blend of one or more types of polymers or polymer alloys.

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

The shape of the polymer molded article (molded body) formed from the resin composition may be any of the following shapes: flat film, powder, spherical particle, crushed particle, bulky continuum, fiber, tubular, hollow fiber, granular, plate, porous, etc. there is.

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

The resin composition can be obtained by mixing compound (I) and resin. Compound (I) may be contained in the amount necessary to provide the desired performance, for example, 0.00001 to 99 parts by mass per 100 parts by mass of the resin.

The resin composition may contain other additives, such as solvents, crosslinking catalysts, tackifiers, plasticizers, softeners, dyes, pigments, inorganic fillers, etc., as needed.

The polymerizable monomer used in composition (1) is not particularly limited, but is preferably a radically polymerizable monomer, more preferably a radically photopolymerizable monomer, and even more preferably a (meth)acrylate.

(Meth)acrylates include monofunctional (meth)acrylate monomers containing one (meth)acryloyloxy group in the molecule, and bifunctional (meth)acrylates containing two (meth)acryloyloxy groups in the molecule. Examples include rate monomers and polyfunctional (meth)acrylate monomers containing three 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, and more preferably a photopolymerization initiator.

Composition (1) can be obtained by mixing compound (I) and a polymerizable monomer. Compound (I) may be contained in the amount necessary to provide the desired performance, for example, 0.01 to 20 parts by mass per 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., as necessary.

<Layer containing compound (I)>

The present invention includes an optical layer containing compound (I). The optical layer containing compound (I) can be laminated on a display device such as an organic EL device or a liquid crystal cell and used in an image display device (FPD: flat panel display) such as an organic EL display device or a liquid crystal display device. The optical layer can be formed using the resin composition of the present invention. When applying the resin composition of the present invention 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, or a coating layer, and is preferably an adhesive layer or a coating layer.

The optical layer containing compound (I) is preferably formed from the above-described resin composition or composition (1).

The optical layer containing compound (I) may be composed of only the optical layer containing compound (I), or may be an optical laminate in which a layer containing compound (I) and other layers are laminated. Other layers include, for example, a polarizing film (polarizer), retardation film, thermoplastic resin film, wavelength conversion layer, etc. If the optical laminate is a laminate in which the optical layer of the present invention, the adhesive layer, and the polarizing film are laminated in that order, it is preferable that the optical layer of the present invention is an optical layer (optical film) formed from a resin composition. 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 that order, the optical layer of the present invention is preferably an optical layer (coating layer) formed from composition (1). . 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 that order, the optical layer of the present invention is preferably an optical layer (adhesive layer) formed from a resin composition. When the optical laminate includes a wavelength conversion layer, it is preferable to arrange the optical layer of the present invention on the viewing side further than the wavelength conversion layer. The optical layer of the present invention may be an optical layer formed from a resin composition, and the composition (1 ) may also be an optical layer formed from.

<Adhesive composition>

When the layer formed from the composition of the present invention is a pressure-sensitive adhesive layer, the pressure-sensitive adhesive composition (hereinafter referred to as pressure-sensitive adhesive composition (1)) includes resin (A), compound (I), crosslinking agent (B), and silane compound (C). It is formed from). The adhesive composition (1) further includes a radical curable component (D), an initiator (E), a light absorption compound (F) other than compound (I) (hereinafter sometimes referred to as a light selective absorption compound (F)), and charging. It may contain an inhibitor, etc., and preferably contains at least one selected from the group consisting of a radical curing component (D), an initiator (E), and a light selective absorption compound (F).

The resin (A) is not particularly limited as long as it is a resin used in the adhesive composition. It is preferable that the resin (A) does not exhibit maximum absorption in the wavelength range of 300 nm to 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, and particularly preferably 0°C or lower. In addition, the glass transition temperature of the resin (A) is usually -80 ℃ or higher, preferably -70 ℃ or higher, more preferably -60 ℃ or higher, even more preferably -55 ℃ or higher, and especially -50 ℃ or higher. desirable. If the glass transition temperature of the resin (A) is 40°C or lower, it is advantageous for improving the adhesion of the adhesive layer formed from the adhesive composition (1) to the adherend. Additionally, if the glass transition temperature of the resin (A) is -80°C or higher, it is advantageous for improving the durability of the adhesive layer formed from the adhesive composition (1). Additionally, the glass transition temperature can be measured by differential scanning calorimetry (DSC).

Resins (A) include (meth)acrylic resins, silicone resins, rubber resins, urethane resins, etc., and are preferably (meth)acrylic resins.

The (meth)acrylic resin is preferably a polymer containing a structural unit derived from (meth)acrylic acid ester as a main component (preferably containing 50% by mass or more). The (meth)acrylic resin may contain structural units derived from monomers other than one or more types of (meth)acrylic acid esters (e.g., structural units derived from monomers having polar functional groups such as hydroxyl groups, carboxyl groups, 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, and more preferably 70% by mass to 90% by mass, based on 100% by mass of solid content of the adhesive composition (1). %am.

The content of compound (I) is usually 0.01 to 20 parts by mass, preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, and especially preferably 0.5 to 5 parts by mass, based on 100 parts by mass of resin (A). It is the mass part.

Examples of the crosslinking agent (B) include isocyanate-based crosslinking agents, epoxy-based crosslinking agents, aziridine-based crosslinking agents, and metal chelate-based crosslinking agents. In particular, from the viewpoint of pot life of the adhesive composition, durability of the adhesive layer, and crosslinking speed, the isocyanate-based crosslinking agent is preferred. desirable.

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, based on 100 parts by mass of the resin (A). It is a mass part, and is especially preferably 0.25 to 2 mass parts.

Silane compounds (C) include, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropyltriene. Toxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane , 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc.

The silane compound (C) may be a silicon 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 7 parts by mass, based on 100 parts by mass of the resin (A). It is 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.

The radically curable component (D) includes a radically curable component such as a compound or oligomer that hardens by a radical polymerization reaction.

Examples of the radically polymerizable component (D) include (meth)acrylate-based compounds, styrene-based compounds, and vinyl-based compounds.

The adhesive composition (1) may contain two or more types of radically curable components (D).

(meth)acrylate-based compounds include (meth)acrylate monomers having at least one (meth)acryloyloxy group in the molecule, (meth)acrylamide monomers, and at least two (meth)acryloyl groups in the molecule. (meth)acryloyl group-containing compounds, such as (meth)acrylic oligomers, are included. The (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. One type of (meth)acrylate-based compound can be used independently, or two or more types can be used in combination.

(meth)acrylate monomers include monofunctional (meth)acrylate monomers with one (meth)acryloyloxy group in the molecule, and bifunctional (meth)acrylate monomers with two (meth)acryloyloxy groups in the molecule. Monomers include polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule.

It is preferable that it is a (meth)acrylate compound, and it is more preferable that it is a polyfunctional (meth)acrylate compound. It is preferable that the 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 5 to 30 parts by mass, relative to 100 parts by mass of the resin (A). It is more preferable that it is negligible, and it is especially preferable that it is 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). In addition, the light here is preferably active energy rays such as visible rays, ultraviolet rays, X-rays, or electron beams.

Thermal polymerization initiators include compounds that generate radicals by heating, etc. (thermal radical generators), compounds that generate acids by heating, etc. (thermal acid generators), and compounds that generate bases by heating, etc. (thermal base generators). I can hear it.

Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), and compounds that generate bases by absorbing light energy. (Photobase generator) etc. are mentioned.

The initiator (E) is preferably selected to be suitable for the polymerization reaction of the radically curable component (D), and is preferably a radical polymerization initiator, and more preferably a radical photopolymerization initiator.

Radical polymerization initiators include, for example, alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, and phosphine compounds. The radical polymerization initiator is preferably a radical photopolymerization initiator, and is more preferably an oxime ester-based radical photopolymerization initiator from the viewpoint of the reactivity of the polymerization reaction. By using an oxime ester-based radical photopolymerization initiator, the reaction rate of the radical curing component (D) can be increased even under curing conditions with low illuminance or light amount.

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 0.75 to 4 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferable, and particularly preferably 1 to 3 parts by mass.

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

The structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light with a wavelength of 250 nm to 380 nm, but may include benzotriazole-based compounds, benzophenone-based compounds, triazine-based compounds, salicylic acid-based compounds, cyanoacrylate-based compounds, Compounds such as benzoxazine-based compounds are preferable.

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

<Dyeing material dyed with compound (I)>

The present invention includes dyed materials (such as 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.

Forms for practicing the invention

The present invention will be described in more detail below through examples and comparative examples. “%” and “part” in examples and comparative examples are “% by mass” and “part by mass” unless otherwise specified.

Example 1: Synthesis of the compound represented by formula (1)

[Formula 29]

A 100 mL-4-necked flask equipped with a Dimro cooling pipe and a thermometer was placed in a nitrogen atmosphere, and the compound represented by formula (m) (4,4a,5,6-tetrahydro-7-hydroxy-2(3H) -naphthalenone), 30 parts of dichloromethane, 4.8 parts of indoline, and 0.9 parts of bismuth nitrate were mixed, and the resulting mixture was stirred at a temperature of 25°C for 40 hours. After distilling off the solvent from the obtained mixture, the mixture was purified with hydrochloric acid and ethyl acetate to obtain 1.3 parts of the 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. Additionally, the presence of chloride anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis).

¹ H-NMR (dimethyl sulfoxide) δ: 7.18 ~ 7.63 (m, 8H), 6.39 (m, 2H), 4.21 ~ 4.40 (m, 4H), 3.64 ~ 4.05 (m, 2H), 3.11 ~ 3.35 ( m, 4H), 2.50 ~ 2.73 (m, 2H), 2.09 (m, 2H), 1.56 ~ 1.59 (m, 2H), 0.90 (m, 1H)

LC-MS; [M] = 367.2

<Measurement of maximum absorption wavelength and gram extinction coefficient ε>

The obtained 2-butanone solution (0.006 g/L) of the compound represented by formula (1) was placed in a 1 cm quartz cell, and the quartz cell was set to a spectrophotometer UV-2450 (manufactured by Shimazu Seisakusho Co., Ltd.). Absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps 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 formula (1) in the solution, and the optical path length of the quartz cell.

ε(λ) = A(λ)/CL

[In the formula, ε(λ) represents the gram extinction coefficient (L/(g·cm)) of the compound represented by equation (1) at the wavelength λ nm, and A(λ) represents the absorbance at the wavelength λ nm. , C represents the concentration (g/L), and L represents the optical path length (m) of the quartz cell.]

The maximum absorption wavelength of the obtained compound represented by formula (1) was 523 nm. The gram extinction coefficient ε(λmax) at the maximum absorption wavelength of the obtained compound represented by formula (1) was 309 L/(g·cm).

<Measurement of the full width at half maximum of the compound>

The obtained 2-butanone solution (concentration: 0.006 g/L) of the compound represented by formula (1) was placed in a 1 cm quartz cell, and the quartz cell was subjected to a spectrophotometer UV-2450 (manufactured by Shimazu Seisakusho Co., Ltd.). After setting, the absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps using the double beam method. Two wavelengths were identified where the absorbance was half that of the maximum absorption wavelength. Among the two wavelengths, the short-wave wavelength was subtracted from the long-wave wavelength to obtain the full width at half maximum. The full width at half maximum of the compound represented by formula (1) was 44 nm.

Example 2: Synthesis of the compound represented by formula (2)

[Formula 30]

A 100 mL-4-necked flask equipped with a Dimro cooling pipe and a thermometer was placed in a nitrogen atmosphere, and the compound represented by formula (m) (4,4a,5,6-tetrahydro-7-hydroxy-2(3H) -naphthalenone), 20 parts of dichloromethane, 3.2 parts of methylindoline, and 1.5 parts of bismuth nitrate were mixed, and the resulting mixture was stirred at a temperature of 25°C for 40 hours. After distilling off the solvent from the obtained mixture, the mixture was purified with hydrochloric acid and ethyl acetate to obtain 1.4 parts of the compound represented by formula (2).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by formula (2) was produced. Additionally, the presence of chloride anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Additionally, the maximum absorption wavelength, gram extinction coefficient, and full width at half maximum were measured in the same manner as described above. As a result, the maximum absorption wavelength of the compound represented by equation (2) was 530 nm, and the gram extinction coefficient ε( λmax) was 237 L/(g·cm), and the full width at half maximum was 54 nm.

¹ H-NMR (dimethyl sulfoxide) δ: 1.58 (m, 2H), 2, 31 (m, 2H), 2.50 (s, 6H), 2.66 (m, 1H), 3.14 ~ 3.35 (m, 8H) , 4.20 ~ 4.30 (m, 4H), 6.31 (m, 2H), 7.09 ~ 7.45 (m, 6H)

LC-MS; [M] = 395.5

Example 3: Synthesis of the compound represented by formula (3)

[Formula 31]

A 100 mL-4-necked flask equipped with a Dimro cooling pipe and a thermometer was placed in a nitrogen atmosphere, and the compound represented by formula (m) (4,4a,5,6-tetrahydro-7-hydroxy-2(3H) -naphthalenone), 30 parts of dehydrated acetonitrile, and 6.6 parts of nitroindoline were mixed, and the resulting mixture was stirred at a temperature of 80°C for 8 hours. After distilling off the solvent from the obtained mixture, it was purified to obtain 1.7 parts of the compound represented by the formula (m-A).

[Formula 32]

A 100 mL-4-neck flask equipped with a Dimro cooling pipe and a thermometer was placed in a nitrogen atmosphere, 0.5 parts of the compound represented by the formula (m-A), 5 parts of dehydrated acetonitrile, and 0.3 parts of diisopropylethylamine were added and stirred in an ice bath. To the resulting mixture, 0.6 parts of trifluoromethanesulfonic anhydride was added and stirred in an ice bath for 15 minutes. 0.27 parts of nitroindoline was added and the mixture was stirred in an ice bath for 1 hour. After distilling off the solvent from the obtained mixture, the mixture was purified with hydrochloric acid and ethyl acetate to obtain 0.6 parts of the compound represented by formula (3).

¹ H-NMR analysis was performed to confirm that the compound represented by formula (3) was produced. Additionally, the presence of chloride anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Additionally, the maximum absorption wavelength, gram extinction coefficient, and full width at half maximum were measured in the same manner as described above. As a result, the maximum absorption wavelength of the compound represented by equation (3) was 521 nm, and the gram extinction coefficient ε( λmax) was 192 L/(g·cm), and the full width at half maximum was 52 nm.

¹ H-NMR (dimethyl sulfoxide) δ: 1.58 (m, 2H), 2.08 (m, 2H), 2.73 (m, 1H), 3.30 (m, 2H), 4.30 (m, 4H), 6.34 (m) , 4H), 7.27 ~ 7.64 (m, 6H), 8.00 ~ 8.11 (m, 2H)

Example 4: Synthesis of the compound represented by formula (4)

[Formula 33]

A 100 mL-4-neck flask equipped with a Dimro cooling pipe and a thermometer was placed in a nitrogen atmosphere, 2 parts of the compound represented by formula (m), 40 parts of dehydrated acetonitrile, and 1.9 parts of diisopropylethylamine were added and stirred in an ice bath. 4.1 parts of trifluoromethanesulfonic anhydride were added and stirred in an ice bath for 15 minutes. 5.2 parts of the compound represented by formula (b1) was added to the obtained mixture and stirred at a temperature of 60°C for 2 hours. After distilling off the solvent from the obtained mixture, the mixture was purified with hydrochloric acid and ethyl acetate to obtain 2 parts of the compound represented by formula (4).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by formula (4) was produced. Additionally, the presence of chloride anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Additionally, the maximum absorption wavelength, gram extinction coefficient, and full width at half maximum were measured in the same manner as described above. As a result, the maximum absorption wavelength of the compound represented by equation (4) was 459 nm, and the gram extinction coefficient ε( λmax) was 100 L/(g·cm), and the full width at half maximum was 70 nm.

¹ H-NMR (dimethyl sulfoxide) δ: 11.2 (m, 2H), 7.44 ~ 7.95 (12H), 7.44 ~ 7.46 (m, 4H), 6.09 (s, 2H), 2.69 ~ 3.00 (m, 5H) , 2.50 (m, 2H), 1.56 ~ 1.59 (m, 2H)

LC-MS; [M] = 552.5

Example 5: Synthesis of the compound represented by formula (5)

[Formula 34]

A 100 mL-4-necked flask equipped with a Dimro cooling pipe and a thermometer was placed in a nitrogen atmosphere, and 0.2 parts of the compound represented by the formula (m), 4 parts of dehydrated acetonitrile, and 0.2 parts of diisopropylethylamine were added and stirred in an ice bath. 0.4 parts of trifluoromethanesulfonic anhydride was added to the resulting mixture and stirred in an ice bath for 15 minutes. 0.9 parts of the compound represented by formula (b2) was added to the obtained mixture and stirred at a temperature of 60°C for 2 hours. After distilling off the solvent from the obtained mixture, the mixture was purified with hydrochloric acid and ethyl acetate to obtain 0.3 part of the compound represented by formula (5).

¹ H-NMR analysis was performed to confirm that the compound represented by formula (5) was produced. Additionally, the presence of chloride anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Additionally, the maximum absorption wavelength, gram extinction coefficient, and full width at half maximum were measured in the same manner as described above. As a result, the maximum absorption wavelength of the compound represented by equation (5) was 457 nm, and the gram extinction coefficient ε( λmax) was 58 L/(g·cm), and the full width at half maximum was 74 nm.

¹ H-NMR (dimethyl sulfoxide) δ: 10.9 (m, 2H), 7.85 ~ 8.00 (m, 22H), 7.42 ~ 7.48 (m, 12H), 6.08 (s, 2H), 2.61 ~ 3.00 (m, 5H), 2.09 (m, 2H), 1.60 ~ 1.65 (m, 2H)

Example 6: Synthesis of the compound represented by formula (6)

[Formula 35]

0.2 parts of the compound represented by formula (1), 100 parts of methyl ethyl ketone, and 0.4 parts of ammonium tetrakis(pentafluorophenyl)borate were added and stirred at a temperature of 25°C for 2 hours. After distilling off the solvent from the obtained mixture, it was purified to obtain 0.3 parts of the compound represented by formula (6).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by formula (6) was produced. Additionally, the presence of tetrakis(pentafluorophenyl)borate anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis). Additionally, the maximum absorption wavelength, gram extinction coefficient, and full width at half maximum were measured in the same manner as described above. As a result, the maximum absorption wavelength of the compound represented by equation (6) was 523 nm, and the gram extinction coefficient ε( λmax) was 121 L/(g·cm), and the full width at half maximum was 48 nm.

¹ H-NMR (dimethyl sulfoxide) δ: 7.18 ~ 7.63 (m, 8H), 6.39 (s, 2H), 4.21 ~ 4.40 (m, 4H), 3.11 ~ 3.35 (m, 4H), 0.81 ~ 2.73 ( m, 9H)

LC-MS; [M＋H] = 367.5, [Nega] = 679.2

Polymerization Example 1: Preparation of acrylic resin (A1)

A mixed solution of 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 3 parts of 2-hydroxyethylmethyl acrylate, and 1 part of acrylic acid as a solvent was injected into a reaction vessel equipped with a cooling pipe, a nitrogen introduction pipe, a thermometer, and a stirrer, and nitrogen gas was added to the reaction vessel equipped with a thermometer and a stirrer. The air inside the furnace was replaced to make it oxygen-free, and the internal temperature was raised to 55°C. After that, the entire solution of 0.14 parts of azobisisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added. After adding the initiator, this temperature was maintained for 1 hour, 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, and when the concentration of the acrylic resin reached 35%, acetic acid was added. The addition of ethyl was stopped, and the temperature was maintained 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 acrylic resin. The obtained acrylic resin had a weight average molecular weight Mw of 1.4 million and Mw/Mn of 5.5 in terms of polystyrene according to GPC. This is referred to as acrylic resin (A1).

Example 7: Preparation of resin composition (1) (adhesive composition (1))

Based on 100 parts of solid content of the ethyl acetate solution (resin concentration: 20%) of the acrylic resin (A1), 0.5 part of crosslinking agent (Tosoh Corporation: brand name "Coronate L", isocyanate-based compound, solid content of 75%), silane 0.28 parts of the compound (manufactured by Shinetsu Chemical Co., Ltd.: product name "KBM3066") was mixed with 0.5 parts of the compound represented by formula (1), and 2-butanone was added so that the solid content concentration was 14% to obtain a resin composition. (1) (adhesive composition) was obtained. In addition, the compounding amount of the crosslinking agent is the number of parts by mass as the active ingredient.

Examples 8 to 18, Comparative Examples 1 and 2: Preparation of resin compositions (2) to (14)

As shown in Table 9, resin compositions (2) to (14) were produced in the same manner as in Example 7, except that each component and the content of each component were changed. In addition, the compounding amount of the crosslinking agent is the number of parts by mass as the active ingredient, and the resin (A) is the number of parts by mass of the solid content.

Additionally, 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

Formula (2): Compound represented by formula (2) synthesized in Example 2

Formula (3): Compound represented by formula (3) synthesized in Example 3

Formula (4): Compound represented by formula (4) synthesized in Example 4

Formula (5): Compound represented by formula (5) synthesized in Example 5

Formula (6): Compound represented by formula (6) synthesized in Example 6

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

KBM3066: manufactured by Shinetsu Kagaku Kogyo Co., Ltd., product name: KBM3066, silane coupling agent

Formula (B1): Compound represented by the following formula (B) (3-butyl-2-[3-(-3-butyl-5-phenyl-2(3H)-) synthesized with reference to the specification of U.S. Patent No. 6004536 Benzolylidene)-1-propen-1-yl]-5-phenyl-benzoxazolium paratoluenesulfonate). The maximum absorption wavelength was 498 nm, and the gram extinction coefficient ε(λmax) at the maximum absorption wavelength was 230 L/(g·cm).

[Formula 36]

Equation (B2): C.I. Solvent Orange 15. The maximum absorption wavelength was 498 nm, and the gram extinction coefficient ε(λmax) at the maximum absorption wavelength was 581 L/(g·cm).

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

[Production of the resin molded body (1)]

The obtained resin composition (1) was applied using an applicator to the release-treated surface of a separate film made of a polyethylene terephthalate film to which release treatment had been performed [trade name "PLR-382190" obtained from Lintech Co., Ltd.], and applied at 100°C. After drying for 1 minute, a resin molded body (adhesive layer) (1) was produced. The thickness of the obtained resin molded body (1) was 20 μm.

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

A polarizing plate was prepared by bonding a cycloolefin film with a thickness of 13 μm to one side of a polarizer with a thickness of 8 μm using an adhesive layer.

After bonding the resin molded body (1) to the polarizer side of the polarizing plate using a laminator, curing for 7 days at a temperature of 23°C and 65% relative humidity to laminate the cycloolefin film/polarizer/resin molded body (1)/separate film. got a sieve The obtained laminate was cut to a size of 30 cm Х 30 cm, the separate film was peeled off, and the resin molded body (1) and alkali-free glass [trade name "EAGLE 1)/A laminate (1-1) containing a laminate structure of glass was obtained.

The obtained laminate (1-1) was subjected to a weather resistance test by putting it into a Sunshine Weather Meter (manufactured by Suga Shikenki Co., Ltd.) for 75 hours under the conditions of a temperature of 63°C and a relative humidity of 50% RH. The absorbance of the extracted laminate (1-1) was measured in the same manner as above. From the measured absorbance, the absorbance retention rate of the sample at a wavelength of 535 nm was determined based on the following equation. The results are shown in Table 10. The closer the absorbance retention rate is to 100, the better the weather resistance is without deterioration of the light selective absorption function.

In addition, the absorption wavelength for evaluating the absorbance retention rate was selected as the wavelength with an absorbance of 1 to 1.5 on the long-wavelength side of the maximum absorption wavelength among the measured absorbances. This is because the wavelength is the absorbance region with the highest sensitivity in terms of measurement precision of the spectroscopic measurement device.

Absorbance retention rate (%)

= (A(535) after weathering test/A(535) before weathering test) Х 100

[In the formula, A(535) represents the absorbance of the laminate (1-1).]

A resin molded body (2) and a laminate (2-1) were manufactured using the resin composition (2) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 560 nm.

A resin molded body (3) and a laminate (3-1) were produced using the resin composition (3) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 550 nm.

A resin molded body (4) and a laminate (4-1) were produced using the resin composition (4) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 550 nm.

A resin molded body (5) and a laminate (5-1) were produced using the resin composition (5) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 535 nm.

A resin molded body (6) and a laminate (6-1) were produced using the resin composition (6) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 570 nm.

A resin molded body (7) and a laminate (7-1) were produced using the resin composition (7) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 535 nm.

A resin molded body (8) and a laminate (8-1) were produced using the resin composition (8) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 540 nm.

A resin molded body (9) and a laminate (9-1) were produced using the resin composition (9) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 485 nm.

A resin molded body (10) and a laminate (10-1) were produced using the resin composition (10) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 485 nm.

A resin molded body (11) and a laminate (11-1) were produced using the resin composition (11) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 485 nm.

A resin molded body (12) and a laminate (12-1) were produced using the resin composition (12) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 485 nm.

A resin molded body (13) and a laminate (13-1) were produced using the resin composition (13) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 510 nm.

A resin molded body (14) and a laminate (14-1) were produced using the resin composition (14) instead of the resin composition (1), and the absorbance retention rate was evaluated in the same manner. The results are shown in Table 10. Absorbance retention evaluation was performed at a wavelength of 485 nm.

Absorbance retention rate Example 7 80.8 Example 8 99.6 Example 9 84.7 Example 10 86.0 Example 11 73.6 Example 12 72.6 Example 13 94.1 Example 14 96.6 Example 15 78.6 Example 16 90.1 Example 17 87.1 Example 18 92.9 Comparative Example 1 3.5 Comparative Example 2 21.8

[Evaluation of bleed resistance of resin molded body (1)]

A separate film was further laminated on one side of the obtained resin molded body (1) to obtain an adhesive layer with a double-sided separate film attached. The obtained resin layer (1) with the double-sided separate film attached was stored in air at a temperature of 23 to 25°C for 1 month. The resin molded body (1) with the double-sided separator film attached after storage was checked for the presence or absence of crystal precipitation of the compound in the surface using a microscope. The case without crystal precipitation was designated as a, and the case with crystal precipitation was designated as b. The evaluation results are shown in Table 11.

Bleed resistance evaluation was similarly performed using resin molded bodies (2) to (14). The results are shown in Table 11.

[Adhesion evaluation]

(sample production)

A polarizing plate was prepared by bonding a cycloolefin film with a thickness of 52 μm and a (meth)acrylic resin film (hereinafter sometimes referred to as PMMA film) with a thickness of 80 μm to both sides of a polarizer with a thickness of 23 μm using an adhesive layer.

After the resin molded body (1) is bonded to the cycloolefin film side of the polarizing plate using a laminator, it is cured for 7 days at a temperature of 23°C and a relative humidity of 65% to form a PMMA film/polarizer/cycloolefin film/resin molded body (1). /A laminate of separate films was obtained. The obtained laminate was cut to a size of 150 mm Х 25 mm so that the absorption axis of the polarizer was parallel to the long side, the separate film was peeled off, and the resin molded body (1) was placed on an alkali-free glass substrate [product name "EAGLE 160 mm, 50 mm in width, 0.7 mm in thickness.] The obtained laminate was pressurized in an autoclave at a temperature of 50°C and a pressure of 5 kgf/cm ² (490.3 kPa) for 20 minutes, and this was used as a sample.

(Adhesion measurement at a temperature of 23°C)

The sample was stored for 24 hours in an environment with a temperature of 23°C and a relative humidity of 55% RH. After that, a cutter blade is inserted between the glass substrate and the adhesive layer to peel 30 mm from the end in the longitudinal direction, and the peeled portion is held by the handle of a universal tensile tester [trade name "AGS-50 NX" manufactured by Shimadzu Seisakusho Co., Ltd.]. I took it as a fortune. The sample in this state was tested in an atmosphere with a temperature of 23°C and a relative humidity of 55% RH, in accordance with JIS K 6854-2: 1999 “Adhesive-Peel Adhesion Strength Test Method-Part 2: 180 Degree Peel” at a handle movement speed of 300 mm/min. A 180-degree peeling test was performed, and the average peeling force over a length of 120 mm excluding the 30 mm of the handle was determined, and this was taken as the adhesion force at a temperature of 23°C. The results are shown in Table 11.

Bleed resistance Adhesion [N/25 mm] Example 7 a 1.55 Example 8 b 1.73 Example 9 b 2.10 Example 10 b 1.92 Example 11 a 2.04 Example 12 a 2.78 Example 13 a 2.55 Example 14 a 2.14 Example 15 a 1.79 Example 16 b 1.76 Example 17 b 2.14 Example 18 b 3.04

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

The purpose of the present invention is to provide a novel compound that efficiently absorbs light in the visible light range (wavelength 400 nm to 750 nm, preferably wavelength 450 nm to 600 nm) and at the same time has good weather resistance.

Claims (15)

A compound containing at least one cation and an anion selected from the cation represented by formula (IA) and the cation represented by formula (IB).

[In formulas (IA) and (IB),
Ring W ¹ and Ring W ² each independently represent a ring structure having at least one double bond as a ring component.
Ring W ¹ and ring W ² may each independently have a substituent.
Ring W ³ and Ring W ⁴ each independently represent a nitrogen-containing heterocyclic group that may have a substituent. However, ring W ³ and ring W ⁴ do not contain a pyrrole ring structure and a sulfur atom.
Ar ¹ and Ar ² each independently represent an aromatic group.
R ¹ and R ² each independently represent a hydrogen atom or a monovalent substituent.] According to paragraph 1,
A compound wherein the anion is an organic anion. According to paragraph 2,
A compound wherein the anion is a methide anion, an amide anion, a sulfonate anion, or a borate anion. According to paragraph 2,
A compound wherein the anion is any one of the anion represented by the formula (cA), the anion represented by the formula (cB), the anion represented by the formula (cC), and the anion represented by the formula (cD).

[In formula (cA), R _1c , R _2c and R _3c each independently represent a monovalent substituent.
In formula (cB), R _4c and R _5c each independently represent a monovalent substituent.
In formula (cC), R _6c represents a monovalent substituent.
In formula (cD), R _7c , R _8c , R _9c and R _10c each independently represent a monovalent substituent.] According to paragraph 4,
R _1c , R _2c , R _3c , R _4c , R _5c , R _6c , R _7c , R _8c , R _9c and R _10c are each independently a fluorine atom, a fluoroalkyl group having 1 to 12 carbon atoms, or a fluoroalkyl group having 6 to 18 carbon atoms A compound that is a fluoroaryl group, cyano group, nitro group, or -SO ₂ -R _11c (R _11c represents a hydrocarbon group having 1 to 12 carbon atoms that may have a fluorine atom). According to paragraph 4,
The anion represented by the formula (c-A1), the anion represented by the formula (c-B1), the anion represented by the formula (c-C1), the anion represented by the formula (c-D1), and the anion represented by the formula (c) A compound that is one of the anions represented by -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 fluoroalkyl group having 1 to 12 carbon atoms. n1 to n4 each independently represent an integer from 0 to 5.] According to clause 6,
A compound wherein the anion is tetrakis(pentafluorophenyl)borate anion. 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 body molded from the composition according to claim 8. A molded body molded from the composition according to claim 9. A dyed material dyed with the compound according to any one of claims 1 to 7. An optical layer comprising the compound according to any one of claims 1 to 7. A laminate in which the optical layer and the wavelength conversion layer according to claim 13 are laminated. A compound represented by the following formula (MA).

[In equation (MA),
Ring W ¹ and Ring W ² each independently represent a ring structure having at least one double bond as a ring component.
Ring W ¹ and ring W ² may each independently have a substituent.
Ring W ⁴ represents a nitrogen-containing heterocyclic group that may have a substituent. However, ring W ⁴ does not contain a pyrrole ring structure and a sulfur atom.]