TWI577748B - Dye with salt - Google Patents

Description

Dye salt

The present invention relates to a dye containing a cation derived from a cyanine compound and an anion derived from a phthalocyanine compound, a dye containing the above salt as an active ingredient, and a colored composition containing the above dye.

In a display device such as a liquid crystal panel, an electroluminescence panel, or a plasma display panel, a color filter can be used.

Further, C.I. (Colour Index) Direct Blue 86 described in Japanese Laid-Open Patent Publication No. Hei 8-146215 is known as a phthalocyanine dye for use in a color filter.

The Mohr absorption coefficient of C.I. Direct Blue 86 described in Patent Document 1 is not necessarily sufficient.

The present invention provides the following [1] to [9].

[1] A salt comprising a cation (A) derived from a cyanine compound and an anion (B) derived from a compound of Phthalocyanine.

[2] The salt according to [1] above, wherein (A) is a cation represented by formula (1) or formula (2),

(In the formula (1), the ring Z ¹ and the ring Z ² independently of each other represent an aromatic ring which may have a substituent; and R ¹ and R ² independently of each other represent an aliphatic group having a substituent of 1 to 12 carbon atoms; a hydrocarbon group or a hydrogen atom; R ³ and R ⁴ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ³ and R ⁴ may form an alkanediyl group together; R ⁵ And R ⁶ may independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ⁵ and R ⁶ may together form an alkanediyl group; R ⁷ and R ⁸ may independently of each other An aliphatic hydrocarbon group or a hydrogen atom having a carbon number of 1 to 12 which may have a substituent, or R ⁷ and R ⁸ may together form an alkanediyl group; X ¹ and X ² independently represent a hydrogen atom or a halogen atom; ₁ means 0 or 1).

(In the formula (2), the ring Z ³ , the ring Z ⁴ , the ring Z ⁵ and the ring Z ⁶ independently of each other represent an aromatic ring which may have a substituent; and R ⁹ and R ¹⁶ represent a carbon number which may have a substituent An aliphatic hydrocarbon group or a hydrogen atom of ～12; R ¹⁰ and R ¹¹ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹⁰ and R ¹¹ may form an alkane together. a dibasic group; R ¹² and R ¹³ independently of each other represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹² and R ¹³ may together form an alkanediyl group; R ¹⁴ and R ¹⁵ may independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁴ and R ¹⁵ may together form an alkanediyl group; and R ¹⁷ and R ¹⁸ may independently represent each other. An aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁷ and R ¹⁸ may form an alkanediyl group together; and R ¹⁹ and R ²⁰ may independently represent a carbon number which may have a substituent. aliphatic hydrocarbon group of 1 to 12 or a hydrogen atom, or R ¹⁹ and R ²⁰ may together form an alkanediyl group; R ²¹ and R ²² independently of each other may represent a substituent having a carbon number of an aliphatic group having 1 to 12 of the Group or a hydrogen atom, or R ²¹ may together form an alkanediyl group with R ^22; L ₁ represents a substituent group may have a carbon number of the two alkyl groups of 1 to ^{12; X 3, X 4, X} 5 and X ⁶ each Independently represents a hydrogen atom or a halogen atom; n ₂ and n ₃ independently represent 0 or 1).

[3] The salt according to [1] above, wherein (A) is a cation represented by the formula (1).

[4] The salt of the above [3], wherein the ring Z ¹ and the ring Z ² are each independently a naphthalene ring which may have a substituent.

[5] The salt of [3] or [4] above, wherein R ¹ and R ² are each n-butyl.

[6] The salt according to any one of the above [3] to [5] wherein R ³ to R ⁶ are each a methyl group.

[7] The salt according to any one of the above [1] to [6] wherein the anion (B) derived from the phthalocyanine compound is an anion derived from C.I. Direct Blue 86, C.I. Direct Blue 87 or C.I. Acid Blue 249.

[8] A dye comprising the salt according to any one of the above [1] to [7] as an active ingredient.

[9] A coloring composition comprising the dye according to [8] above.

The anion derived from the phthalocyanine compound of the present invention and the salt derived from the cation of the cyanine compound have a good Mohr absorption coefficient.

The salt of the present invention contains a cation (A) derived from a cyanine compound (hereinafter referred to as "cation (A)") and an anion (B) derived from a phthalocyanine compound (hereinafter referred to as "anion (B)" "The situation".

The cation (A) can be selected depending on the color of the target color filter.

The cation (A) is preferably sufficiently dissolved in a solvent. Further, the cation (A) is preferably dissolved in a developing solution for forming a pattern to such an extent that it can be patterned. The cation (A) is preferably a cation represented by the formula (1) (hereinafter referred to as "cation (1)") or a cation represented by the formula (2) (hereinafter referred to as "cation (2)"). situation).

(In the formula (1), the ring Z ¹ and the ring Z ² independently of each other represent an aromatic ring which may have a substituent; and R ¹ and R ² independently of each other represent an aliphatic group having a substituent of 1 to 12 carbon atoms; a hydrocarbon group or a hydrogen atom; R ³ and R ⁴ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ³ and R ⁴ may form an alkanediyl group together; R ⁵ And R ⁶ may independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ⁵ and R ⁶ may together form an alkanediyl group; R ⁷ and R ⁸ may independently of each other An aliphatic hydrocarbon group or a hydrogen atom having a carbon number of 1 to 12 which may have a substituent, or R ⁷ and R ⁸ may together form an alkanediyl group; X ¹ and X ² independently represent a hydrogen atom or a halogen atom; ₁ means 0 or 1).

(In the formula (2), the ring Z ³ , the ring Z ⁴ , the ring Z ⁵ and the ring Z ⁶ independently of each other represent an aromatic ring which may have a substituent; and R ⁹ and R ¹⁶ represent a carbon number which may have a substituent An aliphatic hydrocarbon group or a hydrogen atom of ～12; R ¹⁰ and R ¹¹ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹⁰ and R ¹¹ may form an alkane together. a dibasic group; R ¹² and R ¹³ independently of each other represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹² and R ¹³ may together form an alkanediyl group; R ¹⁴ and R ¹⁵ may independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁴ and R ¹⁵ may together form an alkanediyl group; and R ¹⁷ and R ¹⁸ may independently represent each other. An aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁷ and R ¹⁸ may form an alkanediyl group together; and R ¹⁹ and R ²⁰ may independently represent a carbon number which may have a substituent. aliphatic hydrocarbon group of 1 to 12 or a hydrogen atom, or R ¹⁹ and R ²⁰ may together form an alkanediyl group; R ²¹ and R ²² independently of each other may represent a substituent having a carbon number of an aliphatic group having 1 to 12 of the Group or a hydrogen atom, or R ²¹ may together form an alkanediyl group with R ^22; L ₁ represents a substituent group may have a carbon number of the two alkyl groups of 1 to ^{12; X 3, X 4, X} 5 and X ⁶ each Independently represents a hydrogen atom or a halogen atom; n ₂ and n ₃ independently represent 0 or 1).

Further, since both the cation (1) and the cation (2) have a resonance structure, the cations obtained by transferring the respective charges of the formulas (1) and (2) also constitute the salt of the present invention.

The cation (1) has a ring Z ¹ and a ring Z ² .

In the formula (1), the ring Z ¹ and the ring Z ² independently of each other represent an aromatic ring which may have a substituent. The aromatic ring is preferably a benzene ring or a naphthalene ring.

Examples of the substituent of the benzene ring and the naphthalene ring include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group, and a different group. An aliphatic hydrocarbon group such as pentyl, neopentyl or third pentyl; phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, An aromatic hydrocarbon group such as isopropylidene, m-isopropylphenyl or p-cumyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, Alkoxy group such as second butoxy group, third butoxy group, pentyloxy group; aryloxy group such as phenoxy group; aralkyloxy group such as benzyloxy group; methoxycarbonyl group, ethoxycarbonyl group, propoxy group a methoxy group such as a carbonyl group, an ethoxylated group or a benzamidine group; a methylamine sulfonyl group, a dimethylamine sulfonyl group, an ethylamine sulfonyl group, a diethylamine sulfonyl group, a n-propyl group Aminesulfonyl, di-n-propylaminesulfonyl, isopropylaminesulfonyl, diisopropylaminesulfonyl, n-butylaminesulfonyl, di-n-butylaminesulfonyl, etc. Alkylamine sulfonyl; methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, second butyl An alkylsulfonyl group such as a sulfonyl group or a tert-butylsulfonyl group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a nitro group and a cyano group;

Further, when the above substituent has a hydrogen atom, the hydrogen atom may be a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, or a methoxy group, an ethoxy group, a propoxy group or an isopropyl group. Alkoxy groups such as oxy, butoxy, isobutoxy, second butoxy, tert-butoxy, pentyloxy, aryloxy such as phenoxy, benzyloxy, phenyl, o-tolyl , m-tolyl, p-tolyl, xylyl, Substituted with an aromatic hydrocarbon group such as isopropylphenyl, m-isopropylphenyl or p-cumyl, a carboxyl group, a cyano group, a nitro group or the like.

From the viewpoint of solubility, the ring Z ¹ and the ring Z ² are each preferably a naphthalene ring which may have a substituent, and more preferably a naphthalene ring having no substituent.

In the formula (1), X ¹ and X ² each independently represent a hydrogen atom or a halogen atom. The halogen atom may, for example, be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

R ¹ and R ² each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent.

Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a vinyl group, an ethynyl group, a propyl group, an isopropyl group, an isopropenyl group, a 1-propenyl group, a 2-propenyl group, a 2-propynyl group, and a butyl group. Base, isobutyl, t-butyl, tert-butyl, 2-butenyl, 1,3-butadienyl, pentyl, isopentyl, neopentyl, third amyl, 1-methyl Pentyl, 2-methylpentyl, 2-penten-4-ynyl, hexyl, isohexyl, 5-methylhexyl, heptyl, octyl.

Examples of the substituent of the aliphatic hydrocarbon group include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, and a xylyl group. An aromatic hydrocarbon group such as isopropylidene, m-isopropylphenyl or p-cumyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, An alkoxy group such as a second butoxy group, a third butoxy group, a pentyloxy group, a phenoxy group or a benzyloxy group.

A halogen group such as a fluorine group, a chlorine group, a bromine group or an iodine group; furthermore, a carboxyl group, a nitro group or a cyano group.

R ¹ and R ^{2 are} preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms which does not have a substituent, more preferably an alkyl group having 1 to 4 carbon atoms which does not have a substituent, and further preferably an n-butyl group. R ¹ and R ^{2 are} preferably the same groups. In the case where R ¹ and R ² are the same groups, there is a tendency that the molar absorption coefficient is better.

R ³ and R ⁴ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ³ and R ⁴ may form an alkanediyl group together. R ⁵ and R ⁶ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ⁵ and R ⁶ may form an alkanediyl group together. R ⁷ and R ⁸ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ⁷ and R ⁸ may form an alkanediyl group together.

Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a vinyl group, an ethynyl group, a propyl group, an isopropyl group, an isopropenyl group, a 1-propenyl group, a 2-propenyl group, a 2-propynyl group, and a butyl group. Base, isobutyl, t-butyl, tert-butyl, 2-butenyl, 1,3-butadienyl, pentyl, isopentyl, neopentyl, third amyl, 1-methyl Pentyl, 2-methylpentyl, 2-penten-4-ynyl, hexyl, isohexyl, 5-methylhexyl, heptyl, octyl.

Examples of the substituent of the aliphatic hydrocarbon group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, and a third butoxy group. An alkoxy group such as a pentyloxy group, a phenoxy group or a benzyloxy group.

A halogen group such as a fluorine group, a chlorine group, a bromine group or an iodine group; furthermore, a carboxyl group, a nitro group or a cyano group.

Examples of the alkanediyl group include a methylene group, an ethylidene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1. 5-diyl, hexane-1,6-diyl.

When R ³ to R ⁸ are each independently represent an aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom which may have a substituent, each preferably has an alkyl group having 1 to 3 carbon atoms which may have a substituent. More preferably, it may have a methyl group having a substituent, and further preferably a methyl group having no substituent. Preferably, R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ are each the same group.

In the case where R ³ and R ⁴ together form an alkyldiyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 4 to 7 carbon atoms, more preferably pentane-1,5-di. base.

In the case where R ⁵ and R ⁶ together form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 4 to 7 carbon atoms, more preferably pentane-1,5-di. base.

Examples of the hydrocarbon ring containing the above alkanediyl group include a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. In addition, the hydrocarbon ring may have a substituent, and specific examples of the substituent include an alkyl group having 3 or less carbon atoms such as a methyl group, an ethyl group, a n-propyl group or an isopropyl group.

In the case where R ⁷ and R ⁸ together form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 3 to 5 carbon atoms, more preferably a propane-1,5-diyl group. .

Examples of the hydrocarbon ring containing the above alkanediyl group include a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, and a cycloheptene ring. In addition, the hydrocarbon ring may have a substituent, and specific examples of the substituent include an alkyl group having 3 or less carbon atoms such as a methyl group, an ethyl group, a n-propyl group or an isopropyl group.

n ₁ is 0 or 1, preferably 0.

The cation (2) has a ring Z ³ , a ring Z ⁴ , a ring Z ⁵ and a ring Z ⁶ .

In the formula (2), the ring Z ³ , the ring Z ⁴ , the ring Z ⁵ and the ring Z ⁶ independently of each other represent an aromatic ring which may have a substituent. The aromatic ring is preferably a benzene ring or a naphthalene ring.

Examples of the substituent of the benzene ring and the naphthalene ring include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group, and a different group. An aliphatic hydrocarbon group such as pentyl, neopentyl or third pentyl; phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, An aromatic hydrocarbon group such as isopropylidene, m-isopropylphenyl or p-cumyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, Alkoxy group such as second butoxy group, third butoxy group, pentyloxy group; aryloxy group such as phenoxy group; aralkyloxy group such as benzyloxy group; methoxycarbonyl group, ethoxycarbonyl group, propoxy group a methoxy group such as a carbonyl group, an ethoxylated group or a benzamidine group; a methylamine sulfonyl group, a dimethylamine sulfonyl group, an ethylamine sulfonyl group, a diethylamine sulfonyl group, a n-propyl group Aminesulfonyl, di-n-propylaminesulfonyl, isopropylaminesulfonyl, diisopropylaminesulfonyl, n-butylaminesulfonyl, di-n-butylaminesulfonyl, etc. Alkylamine sulfonyl; methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, second butyl An alkylsulfonyl group such as a sulfonyl group or a tert-butylsulfonyl group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a nitro group and a cyano group;

Further, when the above substituent has a hydrogen atom, the hydrogen atom may be a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, or a methoxy group, an ethoxy group, a propoxy group or an isopropyl group. Alkoxy groups such as oxy, butoxy, isobutoxy, second butoxy, tert-butoxy, pentyloxy, aryloxy such as phenoxy, benzyloxy, phenyl, o-tolyl , m-tolyl, p-tolyl, xylyl, Substituted with an aromatic hydrocarbon group such as isopropylphenyl, m-isopropylphenyl or p-cumyl, a carboxyl group, a cyano group, a nitro group or the like.

From the viewpoint of solubility, the ring Z ³ , the ring Z ⁴ , the ring Z ⁵ and the ring Z ⁶ are each preferably a naphthalene ring which may have a substituent, and more preferably a naphthalene ring having no substituent.

In the formula (2), X ³ , X ⁴ , X ⁵ and X ⁶ each independently represent a hydrogen atom or a halogen atom. The halogen atom may, for example, be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

R ⁹ and R ¹⁶ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent.

Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a vinyl group, an ethynyl group, a propyl group, an isopropyl group, an isopropenyl group, a 1-propenyl group, a 2-propenyl group, a 2-propynyl group, and a butyl group. Base, isobutyl, t-butyl, tert-butyl, 2-butenyl, 1,3-butadienyl, pentyl, isopentyl, neopentyl, third amyl, 1-methyl Pentyl, 2-methylpentyl, 2-penten-4-ynyl, hexyl, isohexyl, 5-methylhexyl, heptyl, octyl.

Examples of the substituent of the aliphatic hydrocarbon group include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, and a xylyl group. An aromatic hydrocarbon group such as isopropylidene, m-isopropylphenyl or p-cumyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, An alkoxy group such as a second butoxy group, a third butoxy group, a pentyloxy group, a phenoxy group or a benzyloxy group.

A halogen group such as a fluorine group, a chlorine group, a bromine group or an iodine group; furthermore, a carboxyl group, a nitro group or a cyano group.

R ⁹ and R ^{16 are} preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms which does not have a substituent, more preferably an alkyl group having 1 to 4 carbon atoms which has no substituent, and further preferably an n-butyl group. R ⁹ and R ^{16 are} preferably the same groups. In the case where R ⁹ and R ¹⁶ are the same groups, there is a tendency that the molar absorption coefficient is better.

R ¹⁰ and R ¹¹ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁰ and R ¹¹ may form an alkanediyl group together. R ¹² and R ¹³ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹² and R ¹³ may form an alkanediyl group together. R ¹⁴ and R ¹⁵ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁴ and R ¹⁵ may form an alkanediyl group together. R ¹⁷ and R ¹⁸ each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁷ and R ¹⁸ may form an alkanediyl group together. R ¹⁹ and R ²⁰ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹⁹ and R ²⁰ may form an alkanediyl group together. R ²¹ and R ²² each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ²¹ and R ²² may form an alkanediyl group together.

Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a vinyl group, an ethynyl group, a propyl group, an isopropyl group, an isopropenyl group, a 1-propenyl group, a 2-propenyl group, a 2-propynyl group, and a butyl group. Base, isobutyl, t-butyl, tert-butyl, 2-butenyl, 1,3-butadienyl, pentyl, isopentyl, neopentyl, third amyl, 1-methyl Pentyl, 2-methylpentyl, 2-penten-4-ynyl, hexyl, isohexyl, 5-methylhexyl, heptyl, octyl.

Examples of the substituent of the aliphatic hydrocarbon group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, and a third butoxy group. An alkoxy group such as a pentyloxy group, a phenoxy group or a benzyloxy group.

A halogen group such as a fluorine group, a chlorine group, a bromine group or an iodine group; furthermore, a carboxyl group, a nitro group or a cyano group.

Examples of the alkanediyl group include a methylene group, an ethylidene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1. 5-diyl, hexane-1,6-diyl.

When R ¹⁰ to R ¹⁵ and R ¹⁷ to R ²² are each independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, it is preferably a carbon number which may have a substituent. The alkyl group of 3 is more preferably a methyl group which may have a substituent, and further preferably a methyl group having no substituent. Preferably, R ¹⁰ and R ¹¹ , R ¹² and R ¹³ , R ¹⁴ and R ¹⁵ , R ¹⁷ and R ¹⁸ , R ¹⁹ and R ²⁰ and R ²¹ and R ²² are each the same group.

In the case where R ¹⁰ and R ¹¹ together form an alkyldiyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 4 to 7 carbon atoms, more preferably pentane-1,5-di. base.

In the case where R ¹² and R ¹³ together form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 4 to 7 carbon atoms, more preferably pentane-1,5-di. base.

In the case where R ¹⁷ and R ^{18 are} together to form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 4 to 7 carbon atoms, more preferably a pentane-1,5-di. base.

In the case where R ¹⁹ and R ²⁰ together form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 4 to 7 carbon atoms, more preferably pentane-1,5-di. base.

Examples of the hydrocarbon ring containing the above alkanediyl group include a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. In addition, the hydrocarbon ring may have a substituent, and specific examples of the substituent include an alkyl group having 3 or less carbon atoms such as a methyl group, an ethyl group, a n-propyl group or an isopropyl group.

In the case where R ¹⁴ and R ¹⁵ together form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 3 to 5 carbon atoms, more preferably a propane-1,5-diyl group. .

In the case where R ²¹ and R ^{22 are} together to form an alkanediyl group having 1 to 12 carbon atoms, the alkanediyl group is preferably an alkanediyl group having 3 to 5 carbon atoms, more preferably a propane-1,5-diyl group. .

Examples of the hydrocarbon ring containing the above alkanediyl group include a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, and a cycloheptene ring. In addition, the hydrocarbon ring may have a substituent, and specific examples of the substituent include an alkyl group having 3 or less carbon atoms such as a methyl group, an ethyl group, a n-propyl group or an isopropyl group.

L ₁ represents a hydrocarbon group which may have a substituent.

Examples of the L ₁ include aliphatic hydrocarbon groups such as methylene, ethyl, vinyl, trimethylene, propenyl, propylene, tetramethylene, pentamethylene, and hexamethylene. An alicyclic hydrocarbon group such as a cyclopentyl group, a cyclohexenyl group or a cyclohexylenediene group; an aromatic hydrocarbon group such as a phenyl group, an exophenyl group, a paraphenyl group or a naphthyl group;

Further, in L ₁ , one or a plurality of hydrogen atoms may pass through an amine group, a carboxyl group, or a cyanide as long as it does not impair the brightness of the color filter obtained from the coloring composition containing the salt of the present invention. Substituted with a nitro group, a halogen group, a hydroxyl group or the like.

The L ₁ is preferably an alkanediyl group having 1 to 16 carbon atoms, more preferably an alkanediyl group having 1 to 10 carbon atoms, from the viewpoint of easiness of synthesis or solubility in an organic solvent. Good is a carbon number of 3 to 8 alkanediyl.

n ₂ and n ₃ independently represent 0 or 1, preferably 0.

The cation (A) represents a cation (1) or a cation (2), preferably a cation (1).

Examples of the cation (A) include the following cations.

The anion (B) can be selected depending on the color of the target color filter.

The anion (B) is preferably sufficiently dissolved in a solvent. Further, the anion (B) is preferably dissolved in the developer for forming a pattern to the extent that the pattern can be formed.

The anion (B) is preferably an anion represented by the formula (3) (hereinafter referred to as "anion (3)").

(Formula (3) represents that n hydrogen atoms contained in the compound represented by Formula (4) are substituted by -SO ₃ ^-. n is an integer of 1 or more and 4 or less ;)

Specific examples of the salt containing the anion (3) include C.I. Direct Blue 86, C.I. Direct Blue 87, C.I. Acid Blue 249, and the like, and preferably C.I. Direct Blue 86.

The following anions are mentioned as an anion (B).

Examples of the salt containing the cation (A) and the anion (B) include the following salts.

The salt of the present invention can be produced by contacting the cation (A) with the anion (B) in a solvent. Specifically, the salt containing the anion (B) and the salt containing the cation (A) may be subjected to a salt exchange reaction in a solvent. In this case, it is preferred to react the salt containing the anion (B) with the salt containing the cation (A) at a molar ratio of 1:1 to 1:4.

The method for obtaining the salt of the objective compound from the reaction mixture is not particularly limited, and various known methods can be employed. For example, the reaction mixture may be mixed with an inorganic salt (for example, common salt, etc.) and water, and the precipitated crystals may be collected by filtration. It is preferred to prepare the above inorganic salt as an aqueous solution of an inorganic salt in advance, and then add the reaction mixture to the above aqueous solution. The temperature at the time of adding the reaction mixture is preferably 10 ° C or more and 50 ° C or less, more preferably 10 ° C or more and 40 ° C or less, and further preferably 10 ° C or more and 25 ° C or less. Further, it is preferred to add the reaction mixture to an aqueous solution of an inorganic salt, and then stir at the same temperature for about 0.5 to 2 hours. Preferably, the filtered crystals are washed with water or the like, followed by drying. Further, it may be further purified by a known method such as recrystallization as needed.

The salt of the present invention thus obtained is useful as a dye. In particular, since the salt of the present invention has a high spectral concentration, it is useful as a dye used for a color filter or a fiber material of a display device such as a liquid crystal display device that reflects light or transmits light.

The dye of the present invention is a dye containing a salt formed of a cation (A) and an anion (B) as an active ingredient.

The coloring composition of the present invention contains the dye of the present invention as a coloring agent (hereinafter referred to as "coloring agent (C)"), and preferably further contains a resin (D). More preferably, the coloring composition of the present invention further contains a polymerizable compound (E), a polymerization initiator (F), and a solvent (G).

The colorant (C) may further contain, in addition to the dye of the present invention, a pigment and/or a dye different from the dye of the present invention.

As a dye different from the dye of the present invention, it can be exemplified as a solvent index (Solvent), acidity (Acid), basicity (Basic), reactivity in a Colour Index (published by the British Society of Dyeing and Colorists). Reactive, direct, disperse or reduced (Vat) dyes. More specifically, the dye of the following color index (C.I.) number is mentioned, but it is not limited to these. CI Solvent Yellow 25, 79, 81, 82, 83, 89; CI Acid Yellow 7, 23, 25, 42, 65, 76; CI Reactive Yellow 2, 76, 116; CI Direct Yellow 4, 28, 44, 86 , 132; CI disperse yellow 54, 76; CI solvent orange 41, 54, 56, 99; CI acid orange 56, 74, 95, 108, 149, 162; CI reactive orange 16; CI direct orange 26; CI solvent red 24, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 160, 218; CI acid red 73, 91, 92, 97, 138, 151, 211, 274, 289; CI Acid Violet 102; CI Solvent Green 1, 5; CI Acid Green 3, 5, 9, 25, 28; CI Alkaline Green 1; CI Reducing Green 1 and the like.

As the pigment, an organic pigment or an inorganic pigment which is usually used for a pigment dispersion resist can be mentioned. Examples of the inorganic pigment include a metal compound such as a metal oxide or a metal salt, and specific examples thereof include oxidation of a metal such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc or ruthenium. Or composite metal oxide. Further, specific examples of the organic pigment and the inorganic pigment include a compound classified as a pigment in a Colour Index (published by the British Society of Coloring and Colorists). More specifically, the following pigment index (C.I.) number of pigments may be mentioned, but it is not limited thereto. CI Pigment Yellow 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173 and 180; CI Pigment oranges 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168 , 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264; CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38; CI Pigment Green 7, 10, 15, 25, 36, 47, and 58 etc.

The content of the colorant (C) is preferably from 5 to 60% by mass based on the solid content of the coloring composition. Here, the solid content component means the total of the components other than the solvent in the coloring composition.

The content of the dye of the present invention contained in the colorant (C) is preferably from 3 to 100% by mass.

The dyes and pigments different from the dye of the present invention may be used alone or in combination with the dye of the present invention, or may be used in combination with the dye of the present invention.

The resin (D) is not particularly limited and any resin can be used. The resin (D) is preferably an alkali-soluble resin, more preferably a resin containing a structural unit derived from (meth)acrylic acid. Here, (meth)acrylic acid means acrylic acid and/or methacrylic acid.

Specific examples of the resin (D) include methacrylic acid/phenyl methacrylate copolymer, methacrylic acid/phenyl methacrylate/styrene copolymer, and methacrylic acid/phenyl methacrylate/ Methacrylic acid drop Ester copolymer, methacrylic acid/styrene/phenyl methacrylate/N-phenylmaleimide copolymer, methacrylic acid/styrene/glycidyl methacrylate copolymer, and the like.

The polystyrene-equivalent weight average molecular weight of the resin (D) is preferably from 5,000 to 35,000, more preferably from 6,000 to 30,000.

The acid value of the resin (D) is preferably from 50 to 150, more preferably from 60 to 135.

The content of the resin (D) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, based on the solid content of the coloring composition.

The polymerizable compound (E) is not particularly limited as long as it is a compound which can be polymerized by an active radical, an acid or the like which is produced from the polymerization initiator (F). For example, a polymerizable compound having an ethylenically unsaturated bond or the like can be mentioned.

The polymerizable compound (E) is preferably a polymerizable compound having three or more polymerizable groups. Examples of the polymerizable compound having three or more polymerizable groups include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethyl acrylate, dipentaerythritol hexaacrylate, and Pentaerythritol hexamethacrylate or the like. These polymerizable compounds may be used alone or in combination of two or more.

The content of the polymerizable compound (E) is preferably 5 to 65% by mass, and more preferably 10 to 60% by mass based on the solid content of the coloring composition.

Examples of the polymerization initiator (F) include a living radical generator, an acid generator, and the like. The living radical generator generates active radicals by the action of heat or light. Examples of the living radical generating agent include an alkylphenone compound, a thioxanthone compound, and three Compounds, hydrazine compounds, and the like.

Examples of the alkylphenone compound include 2-methyl-2-morpholinyl-1-(4-methylsulfonylphenyl)propan-1-one and 2-hydroxy-2-methyl. 1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone and the like.

Examples of the above thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthiaxanone, and 2,4-dichloro. Xanthone, 1-chloro-4-propoxythiaxanone, and the like.

As the above three The compound may, for example, be 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-tri , 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-three 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-three Wait.

Examples of the ruthenium compound include an O-fluorenyl ruthenium compound, and specific examples thereof include N-benzylideneoxy-1-(4-phenylsulfonylphenyl)butan-1-one. -2-imine, N-benzylideneoxy-1-(4-phenylsulfonylphenyl)octane-1-one-2-imine, N-acetoxy-1-[9 -ethyl-6-(2-benzylidenyl)-9H-indazol-3-yl]ethane-1-imine, N-ethyloxy-1-[9-ethyl-6-{ 2-methyl-4-(3,3-dimethyl-2,4-dioxycyclopentylmethoxy)benzylidenyl}-9H-indazol-3-yl]ethane-1- Imine and the like.

Further, as the living radical generating agent, for example, 2,4,6-trimethylbenzimidyldiphenylphosphine oxide or 2,2'-bis(o-chlorophenyl)-4,4' can also be used. ,5,5'-tetraphenyl-1,2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethyl hydrazine, diphenylethylenedione, 9,10-phenanthrenequinone, Camphorquinone, methyl phenylglyoxylate, titanocene compound, and the like.

Examples of the acid generator include 4-hydroxyphenyldimethylhydrazine p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, and 4-ethenyloxyphenyldimethylate. Base p-toluenesulfonate, benzyl (4-acetoxyphenyl)methylphosphonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, two An onium salt such as phenylhydrazine p-toluenesulfonate or diphenylphosphonium hexafluoroantimonate; or a nitrobenzyl tosylate or a benzoin tosylate.

These polymerization initiators may be used alone or in combination of two or more.

The content of the polymerization initiator (F) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the total of the resin (D) and the polymerizable compound (E). When the content of the polymerization initiator is in the above range, the sensitivity is improved, the exposure time is shortened, and the productivity is improved, which is preferable.

Examples of the solvent (G) include ethers, aromatic hydrocarbons, ketones, alcohols, esters, and guanamines.

Examples of the above ethers include tetrahydrofuran, tetrahydropyran, and 1,4-two. Alkane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl Ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate , propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol single Butyl ether acetate and the like.

Examples of the aromatic hydrocarbons include benzene, toluene, xylene, and mesitylene.

Examples of the ketones include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, and 4-hydroxy-4-methyl- 2-pentanone, cyclopentanone, cyclohexanone, and the like.

Examples of the alcohols include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.

Examples of the esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, and butyric acid. Ethyl ester, butyl butyrate, alkyl ester, methyl lactate, ethyl lactate, butyl lactate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethoxy acetic acid Methyl ester, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, Methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, Methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate Ethyl acetate, ethyl 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, γ-butyrolactone, and the like.

Examples of the above guanamines include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

These solvents may be used alone or in combination of two or more.

The content of the solvent (G) in the coloring composition is preferably from 70 to 95% by mass, more preferably from 75 to 90% by mass, based on the coloring composition.

The colored composition of the present invention may contain various additives such as a surfactant, a filler, another polymer compound, an adhesion promoter, an antioxidant, an ultraviolet absorber, a light stabilizer, and a chain transfer agent as needed.

The salts of the invention are useful as dyes. From the viewpoint of a high molar absorption coefficient and exhibiting solubility in an organic solvent, it is particularly useful as a dye used for a color filter of a display device such as a liquid crystal display device.

Further, the coloring composition containing the salt of the present invention can be known in a known manner as a display device having a color filter as a part of its constituent parts (for example, a known liquid crystal display device, organic EL (Electroluminescence), electroluminescence) Various devices for coloring images, such as devices and solid-state imaging devices, are used.

Example

Next, the present invention will be specifically described by way of examples.

In the examples and comparative examples, the % or the part of the content or the amount used is based on the mass unless otherwise specified.

In the following examples, the compounds were identified by elemental analysis (VARIO-EL, manufactured by Elementar Co., Ltd.).

Example 1

7.8 g of C.I. Direct Blue 86 (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 20 g of N,N-dimethylformamide to prepare a solution (s1). Further, 12.5 g of the compound represented by the following formula (d-1) was dissolved in 20 g of N,N-dimethylformamide to prepare a solution (t1). The (s1) solution was added dropwise to (t1) at 25 ° C for 1 hour, followed by stirring for 2 hours. Thereafter, 100 g of ion-exchanged water was added, followed by stirring for 1 hour. Thereafter, suction filtration was carried out and washed with 100 g of ion-exchanged water to obtain 10.5 g of the salt represented by the formula (I-1).

Identification of the compound represented by formula (I-1); (elemental analysis) C: 72.3 H: 5.4 N: 9.4 Cu: 3.6 S: 3.6

Example 2

7.8 g of C.I. Direct Blue 86 (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 20 g of N,N-dimethylformamide to prepare a solution (s3). Further, 6.2 g of the compound represented by the following formula (d-1) was dissolved in 20 g of N,N-dimethylformamide to prepare a solution (t2). The solution (t2) was added dropwise to (s2) at 25 ° C for 1 hour, followed by stirring for 2 hours. Thereafter, 100 g of ion-exchanged water was added, followed by stirring for 1 hour. Thereafter, suction filtration was carried out and washed with 100 g of ion-exchanged water to obtain 6.9 g of the salt represented by the formula (I-2).

Identification of the compound represented by formula (I-2); (elemental analysis) C: 65.7 H: 5.1 N: 10.5 Cu: 4.7 S: 4.8

Example 3

2.5 g of C.I. Direct Blue 86 (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 20 g of N,N-dimethylformamide to prepare a solution (s3). Further, 3.5 g of the compound represented by the following formula (d-2) was dissolved in 30 g of N,N-dimethylformamide to prepare a solution (t3). The (t3) solution was added dropwise to (s3) over 1 hour at 25 ° C, followed by stirring for 2 hours. Thereafter, 150 g of ion-exchanged water was added, followed by stirring for 1 hour. Thereafter, suction filtration was carried out and washed with 100 g of ion-exchanged water to obtain 3.2 g of the salt represented by the formula (I-3).

Identification of the compound represented by formula (I-3); (elemental analysis) C: 71.3 H: 5.4 N: 9.9 Cu: 3.7 S: 3.8

<Measurement of absorbance>

A solution of 0.35 g of the compound was dissolved in ethyl lactate to a volume of 250 cm ³ , and 2 cm ^{3 of} the compound was diluted with ethyl lactate to 100 cm ³ to adjust the concentration to 0.028 g/L. For the solution, a maximum absorption wavelength (λ _max ) and a molar absorption coefficient were measured using an ultraviolet-visible spectrophotometer (V-650DS, manufactured by JASCO Corporation) (quartz cuvette, optical path length 1 cm). The results are shown in Table 1.

Example 4 [Preparation of coloring composition]

will

(C) Colorant: Compound (I-1), compound synthesized in Example 1 20 parts

(D) Resin: methacrylic acid/phenyl methacrylate copolymer (mol ratio 30/70, weight average molecular weight 10700, acid value 70 mgKOH/g) 70 parts

(E) Polymeric compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 30 parts

(F) Polymerization initiator: benzyl dimethyl ketal (Irgacure (registered trademark) 651, manufactured by Ciba-JAPAN Co., Ltd.) 15 parts

(G) Solvent: ethyl lactate 680 parts

Mixing to obtain a coloring composition.

Production of color filters

The coloring composition obtained above was applied to the glass by a spin coating method to volatilize the volatile component. After cooling, light irradiation was performed using a patterned quartz glass reticle and an exposure machine. After light irradiation, development was carried out in an aqueous potassium hydroxide solution, and the mixture was heated to 200 ° C in an oven to obtain a color filter.

From the results of Table 1, it is understood that the salt of the present invention has a high molar absorption coefficient and exhibits a high spectral concentration. Further, the coloring composition containing the compound has excellent color properties and can be utilized in the production of high quality color filters.

Industrial availability

The salt of the present invention is useful as a coloring agent. The salt of the present invention is useful as a coloring agent used for a color filter of a display device such as a liquid crystal display device from the viewpoint of a high molar absorption coefficient and a high spectral concentration.

Claims (8)

a salt comprising a cation (A) derived from a cyanine compound and an anion (B) derived from a phthalocyanine compound, wherein (A) is a cation represented by the formula (1) or the formula (2), (In the formula (1), the ring Z ¹ and the ring Z ² independently of each other represent an aromatic ring which may have a substituent, and R ¹ and R ² independently of each other represent an aliphatic group having 1 to 12 carbon atoms which may have a substituent. a hydrocarbon group or a hydrogen atom, and R ³ and R ⁴ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ³ and R ⁴ may form an alkanediyl group together, R ⁵ And R ⁶ may independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ⁵ and R ⁶ may together form an alkanediyl group, and R ⁷ and R ⁸ may independently of each other. An aliphatic hydrocarbon group or a hydrogen atom having a carbon number of 1 to 12 which may have a substituent, or R ⁷ and R ⁸ may together form an alkanediyl group; X ¹ and X ² independently represent a hydrogen atom or a halogen atom, n ₁ means 0 or 1) (In the formula (2), the ring Z ³ , the ring Z ⁴ , the ring Z ⁵ and the ring Z ⁶ independently of each other represent an aromatic ring which may have a substituent, and R ⁹ and R ¹⁶ represent a carbon number which may have a substituent. An aliphatic hydrocarbon group or a hydrogen atom of ～12, R ¹⁰ and R ¹¹ each independently represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹⁰ and R ¹¹ may form an alkane together. The diradical group, R ¹² and R ¹³ independently of each other represent an aliphatic hydrocarbon group or a hydrogen atom which may have a substituent of 1 to 12 carbon atoms, or R ¹² and R ¹³ may form an alkanediyl group together, R ¹⁴ and R ¹⁵ may independently represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁴ and R ¹⁵ may form an alkanediyl group together, and R ¹⁷ and R ¹⁸ may independently represent each other. An aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, or R ¹⁷ and R ¹⁸ may form an alkanediyl group together, and R ¹⁹ and R ²⁰ may independently represent each other and may have a carbon number of a substituent. aliphatic hydrocarbon group of 1 to 12 or a hydrogen atom, or R ¹⁹ and R ²⁰ may together form a -alkanediyl, R ²¹ and R ²² independently of each other may represent a substituent having a carbon number of an aliphatic group having 1 to 12 of the Group or a hydrogen atom, or R ²¹ and R ²² may together form an alkanediyl group; L ₁ represents a substituent group may have a carbon number of the two alkyl groups of 1 to ^{12, X 3, X 4, X} 5 and X ⁶ each Independently represents a hydrogen atom or a halogen atom, and n ₂ and n ₃ independently represent 0 or 1). The salt of claim 1, wherein (A) is a cation represented by formula (1). The salt of claim 2, wherein the ring Z ¹ and the ring Z ² are each independently a naphthalene ring which may have a substituent. A salt according to claim 2, wherein R ¹ and R ² are n-butyl. The salt of claim 2, wherein R ³ to R ⁶ are methyl. The salt of claim 1, wherein the anion (B) derived from the phthalocyanine compound is an anion derived from C.I. Direct Blue 86, C.I. Direct Blue 87 or C.I. Acid Blue 249. A dye comprising the salt of claim 1 as an active ingredient. A coloring composition comprising the dye of claim 7.