JP5948858B2 - Dye salt - Google Patents

Description

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

  Color filters are used in display devices such as liquid crystal panels, electroluminescence panels, and plasma display panels. As phthalocyanine dyes used in color filters, C.I. I. Direct Blue 86 is known.

JP-A-8-146215

  The C.I. I. Direct blue 86 was not always satisfactory in terms of its molar extinction coefficient.

（式（１）中、環Ｚ^１及び環Ｚ^２は、互いに独立に、置換基を有していてもよい芳香環を表す。Ｒ^１及びＲ^２は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表す。Ｒ^３及びＲ^４は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^３とＲ^４とが一緒になってアルカンジイル基を形成する。Ｒ^５及びＲ^６は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^５とＲ^６とが一緒になってアルカンジイル基を形成する。Ｒ^７及びＲ^８は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^７とＲ^８とが一緒になってアルカンジイル基を形成する。Ｘ^１及びＸ^２は、互いに独立に、水素原子又はハロゲン原子を表す。ｎ_１は、０又は１を表す。）

（式（２）中、環Ｚ^３、環Ｚ^４、環Ｚ^５及び環Ｚ^６は、互いに独立に、置換基を有していてもよい芳香環を表す。Ｒ^９及びＲ^１６は、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表す。Ｒ^１０及びＲ^１１は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１０とＲ^１１とが一緒になってアルカンジイル基を形成する。Ｒ^１２及びＲ^１３は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１２とＲ^１３とが一緒になってアルカンジイル基を形成する。Ｒ^１４及びＲ^１５は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１４とＲ^１５とが一緒になってアルカンジイル基を形成する。Ｒ^１７及びＲ^１８は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１７とＲ^１８とが一緒になってアルカンジイル基を形成する。Ｒ^１９及びＲ^２０は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１９とＲ^２０とが一緒になってアルカンジイル基を形成する。Ｒ^２１及びＲ^２２は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^２１とＲ^２２とが一緒になってアルカンジイル基を形成する。Ｌ_１は、置換基を有してもよい炭素数１〜１２のアルカンジイル基を表す。Ｘ^３、Ｘ^４、Ｘ^５及びＸ^６は、互いに独立に、水素原子又はハロゲン原子を表す。ｎ_２及びｎ_３は、互いに独立に、０又は１を表す。）
［３］ （Ａ）が、式（１）で表されるカチオンである［１］記載の塩。
［４］ 環Ｚ^１及び環Ｚ^２が、互いに独立に、置換基を有してもよいナフタレン環である［３］記載の塩。
［５］ Ｒ^１及びＲ^２が、ともにｎ−ブチル基である［３］又は［４］記載の塩。
［６］ Ｒ^３〜Ｒ^６が、いずれもメチル基である［３］〜［５］のいずれか記載の塩。
［７］ フタロシアニン化合物に由来するアニオン（Ｂ）が、Ｃ．Ｉ．ダイレクトブルー８６、Ｃ．Ｉ．ダイレクトブルー８７又はＣ．Ｉ．アシッドブルー２４９に由来するアニオンである［１］〜［６］のいずれか記載の塩。
［８］ ［１］〜［７］のいずれか記載の塩を有効成分とする染料。
［９］ ［８］記載の染料を含む着色組成物。 The present invention provides the following [1] to [9].
[1] A salt containing a cation (A) derived from a cyanine compound and an anion (B) derived from a phthalocyanine compound [2] (A) is a cation represented by formula (1) or formula (2) The salt according to [1].

(In formula (1), ring Z ¹ and ring Z ² each independently represent an aromatic ring which may have a substituent. R ¹ and R ² each independently have a substituent. Represents an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, and R ³ and R ⁴ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms. Alternatively, it represents a hydrogen atom, or R ³ and R ⁴ together form an alkanediyl group, and R ⁵ and R ⁶ each independently have 1 to 12 carbon atoms which may have a substituent. Represents an aliphatic hydrocarbon group or a hydrogen atom, or R ⁵ and R ⁶ together form an alkanediyl group, and R ⁷ and R ⁸ are each independently a carbon that may have a substituent. Represents an aliphatic hydrocarbon group of formula 1 to 12 or a hydrogen atom, or R ⁷ and R ⁸ together form an alkanediyl group X ¹ and X ² each independently represent a hydrogen atom or a halogen atom, and n ₁ represents 0 or 1.)

(In Formula (2), Ring Z ³ , Ring Z ⁴ , Ring Z ⁵ and Ring Z ⁶ each independently represent an aromatic ring which may have a substituent. R ⁹ and R ¹⁶ are substituted. Represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a group or a hydrogen atom, and R ¹⁰ and R ¹¹ are each independently an aliphatic group having 1 to 12 carbon atoms which may have a substituent. Represents an aromatic hydrocarbon group or a hydrogen atom, or R ¹⁰ and R ¹¹ together form an alkanediyl group, and R ¹² and R ¹³ independently of each other may have a substituent. Represents an aliphatic hydrocarbon group or a hydrogen atom of 1 to 12, or R ¹² and R ¹³ together form an alkanediyl group, and R ¹⁴ and R ¹⁵ each independently have a substituent. or even represents an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms in ^{the R 14} and ^{R 15} is one .R ¹⁷ and R ¹⁸ to form an alkanediyl group is in the are, independently of one another represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, and R ¹⁷ R ¹⁸ and R ¹⁸ together form an alkanediyl group, and R ¹⁹ and R ²⁰ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom. R ¹⁹ and R ²⁰ together form an alkanediyl group, and R ²¹ and R ²² are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. Alternatively, it represents a hydrogen atom, or R ²¹ and R ²² together form an alkanediyl group, and L ₁ represents an alkanediyl group having 1 to 12 carbon atoms which may have a substituent. ^{3, X} 4, ^{X 5} and ^{X 6,} independently of one another, a hydrogen atom .N ₂ and _{n 3} represents a halogen atom is, independently, represent 0 or 1.)
[3] The salt according to [1], wherein (A) is a cation represented by the formula (1).
[4] The salt according to [3], wherein ring Z ¹ and ring Z ² are each independently a naphthalene ring which may have a substituent.
[5] The salt according to [3] or [4], wherein R ¹ and R ² are both n-butyl groups.
[6] The salt according to any one of [3] to [5], wherein R ^{3 to} R ⁶ are all methyl groups.
[7] The anion (B) derived from the phthalocyanine compound is C.I. I. Direct Blue 86, C.I. I. Direct Blue 87 or C.I. I. The salt according to any one of [1] to [6], which is an anion derived from Acid Blue 249.
[8] A dye comprising the salt according to any one of [1] to [7] as an active ingredient.
[9] A coloring composition comprising the dye according to [8].

  The salt of the anion derived from the phthalocyanine compound according to the present invention and the cation derived from the cyanine compound has a good molar extinction coefficient.

  The salt of the present invention has a cation (A) derived from a cyanine compound (hereinafter sometimes referred to as “cation (A)”) and an anion (B) derived from a phthalocyanine compound (hereinafter referred to as “anion (B)”). ).

（式（１）中、環Ｚ^１及び環Ｚ^２は、互いに独立に、置換基を有していてもよい芳香環を表す。Ｒ^１及びＲ^２は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表す。Ｒ^３及びＲ^４は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^３とＲ^４とが一緒になってアルカンジイル基を形成する。Ｒ^５及びＲ^６は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^５とＲ^６とが一緒になってアルカンジイル基を形成する。Ｒ^７及びＲ^８は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^７とＲ^８とが一緒になってアルカンジイル基を形成する。Ｘ^１及びＸ^２は、互いに独立に、水素原子又はハロゲン原子を表す。ｎ_１は、０又は１を表す。）

（式（２）中、環Ｚ^３、環Ｚ^４、環Ｚ^５及び環Ｚ^６は、互いに独立に、置換基を有していてもよい芳香環を表す。Ｒ^９及びＲ^１６は、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表す。Ｒ^１０及びＲ^１１は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１０とＲ^１１とが一緒になってアルカンジイル基を形成する。Ｒ^１２及びＲ^１３は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１２とＲ^１３とが一緒になってアルカンジイル基を形成する。Ｒ^１４及びＲ^１５は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１４とＲ^１５とが一緒になってアルカンジイル基を形成する。Ｒ^１７及びＲ^１８は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１７とＲ^１８とが一緒になってアルカンジイル基を形成する。Ｒ^１９及びＲ^２０は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^１９とＲ^２０とが一緒になってアルカンジイル基を形成する。Ｒ^２１及びＲ^２２は、互いに独立に、置換基を有してもよい炭素数１〜１２の脂肪族炭化水素基又は水素原子を表すか、Ｒ^２１とＲ^２２とが一緒になってアルカンジイル基を形成する。Ｌ_１は、置換基を有してもよい炭素数１〜１２のアルカンジイル基を表す。Ｘ^３、Ｘ^４、Ｘ^５及びＸ^６は、互いに独立に、水素原子又はハロゲン原子を表す。ｎ_２及びｎ_３は、互いに独立に、０又は１を表す。） The cation (A) can be selected according to the color of the target color filter.
It is preferable that the cation (A) is sufficiently dissolved in the solvent. Furthermore, the cation (A) is preferably dissolved in the developer used for pattern formation to the extent that pattern formation is possible. The cation (A) may be a cation represented by the formula (1) (hereinafter may be referred to as “cation (1)”) or a cation represented by the formula (2) (hereinafter referred to as “cation (2)”). ) Is preferred.

(In formula (1), ring Z ¹ and ring Z ² each independently represent an aromatic ring which may have a substituent. R ¹ and R ² each independently have a substituent. Represents an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, and R ³ and R ⁴ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms. Alternatively, it represents a hydrogen atom, or R ³ and R ⁴ together form an alkanediyl group, and R ⁵ and R ⁶ each independently have 1 to 12 carbon atoms which may have a substituent. Represents an aliphatic hydrocarbon group or a hydrogen atom, or R ⁵ and R ⁶ together form an alkanediyl group, and R ⁷ and R ⁸ are each independently a carbon that may have a substituent. Represents an aliphatic hydrocarbon group of formula 1 to 12 or a hydrogen atom, or R ⁷ and R ⁸ together form an alkanediyl group X ¹ and X ² each independently represent a hydrogen atom or a halogen atom, and n ₁ represents 0 or 1.)

(In Formula (2), Ring Z ³ , Ring Z ⁴ , Ring Z ⁵ and Ring Z ⁶ each independently represent an aromatic ring which may have a substituent. R ⁹ and R ¹⁶ are substituted. Represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a group or a hydrogen atom, and R ¹⁰ and R ¹¹ are each independently an aliphatic group having 1 to 12 carbon atoms which may have a substituent. Represents an aromatic hydrocarbon group or a hydrogen atom, or R ¹⁰ and R ¹¹ together form an alkanediyl group, and R ¹² and R ¹³ independently of each other may have a substituent. Represents an aliphatic hydrocarbon group or a hydrogen atom of 1 to 12, or R ¹² and R ¹³ together form an alkanediyl group, and R ¹⁴ and R ¹⁵ each independently have a substituent. or even represents an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms in ^{the R 14} and ^{R 15} is one .R ¹⁷ and R ¹⁸ to form an alkanediyl group is in the are, independently of one another represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, and R ¹⁷ R ¹⁸ and R ¹⁸ together form an alkanediyl group, and R ¹⁹ and R ²⁰ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom. R ¹⁹ and R ²⁰ together form an alkanediyl group, and R ²¹ and R ²² are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. Alternatively, it represents a hydrogen atom, or R ²¹ and R ²² together form an alkanediyl group, and L ₁ represents an alkanediyl group having 1 to 12 carbon atoms which may have a substituent. ^{3, X} 4, ^{X 5} and ^{X 6,} independently of one another, a hydrogen atom .N ₂ and _{n 3} represents a halogen atom is, independently, represent 0 or 1.)

  In addition, since both the cation (1) and the cation (2) have a resonance structure, the cation having the transferred charge in the formula (1) and the formula (2), respectively, constitutes the salt of the present invention.

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

In formula (1), ring Z ¹ and ring Z ² each independently 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 on the benzene ring and the naphthalene ring include
Aliphatic hydrocarbon groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl;
Aromatic hydrocarbon groups such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group;
Alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group;
Aryloxy groups such as phenoxy groups;
An aralkyloxy group such as a benzyloxy group;
Acyloxy groups such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, acetoxy group, benzoyloxy group;
Methylsulfamoyl group, dimethylsulfamoyl group, ethylsulfamoyl group, diethylsulfamoyl group, n-propylsulfamoyl group, di-n-propylsulfamoyl group, isopropylsulfamoyl group, diisopropylsulfamoyl group Alkylsulfamoyl groups such as a famoyl group, n-butylsulfamoyl group, di-n-butylsulfamoyl group;
Alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
Examples thereof include a nitro group and a cyano group.
When the substituent has a hydrogen atom, the hydrogen atom is, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, or a butoxy group. , Isobutoxy group, sec-butoxy group, tert-butoxy group, alkoxy group such as pentyloxy group; aryloxy group such as phenoxy group, benzyloxy group; phenyl group, o-tolyl group, m-tolyl group, p-tolyl group An aromatic hydrocarbon group such as a group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group; carboxy group; cyano group; nitro group;

From the viewpoint of solubility, each of the ring Z ¹ and the ring Z ² is 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. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

R ¹ and R ² each independently represent a C 1-12 aliphatic hydrocarbon group or hydrogen atom 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. , Isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 1,3-butadienyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group Group, 2-pentene-4-ynyl group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group and octyl group.
Examples of the substituent in the aliphatic hydrocarbon group include:
Aromatic hydrocarbon groups such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group;
Examples thereof include alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, phenoxy group and benzyloxy group.
Halogen groups such as fluoro, chloro, bromo and iodo groups;
Furthermore, a carboxy group, a nitro group, and a cyano group are mentioned.

R ¹ and R ² are preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms having no substituent, and more preferably an alkyl group having 1 to 4 carbon atoms having no substituent. More preferably, it is an n-butyl group. R ¹ and R ² are preferably the same group. When R ¹ and R ² are the same group, the molar extinction coefficient tends to be better.

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

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. , Isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 1,3-butadienyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group Group, 2-pentene-4-ynyl group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group and octyl group.
Examples of the substituent in the aliphatic hydrocarbon group include:
Examples thereof include alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, phenoxy group and benzyloxy group.
Halogen groups such as fluoro, chloro, bromo and iodo groups;
Furthermore, a carboxy group, a nitro group, and a cyano group are mentioned.
Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, A hexane-1,6-diyl group is mentioned.

When R < ³ > -R < ⁸ > represents the C1-C12 aliphatic hydrocarbon group or hydrogen atom which may have a substituent each independently, Preferably, you may have a substituent, respectively. It is a C1-C3 alkyl group, More preferably, it is a methyl group which may have a substituent, More preferably, it is a methyl group which does not have a substituent. R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁷ and R ⁸ are preferably the same group.

When R ³ and R ⁴ 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 , A pentane-1,5-diyl group.

When 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 , A pentane-1,5-diyl group.

  Examples of the hydrocarbon ring containing the alkanediyl group include a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. 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, an n-propyl group, and an isopropyl group. be able to.

When 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 Propane-1,5-diyl group.

  Examples of the hydrocarbon ring containing the alkanediyl group include a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, and a cycloheptene ring. 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, an n-propyl group, and an isopropyl group. be able to.

n ₁ is 0 or 1, and is 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 each independently represent an aromatic ring which may have a substituent. The aromatic ring is preferably a benzene ring or a naphthalene ring.

Examples of the substituents on the benzene ring and the naphthalene ring include:
Aliphatic hydrocarbon groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl;
Aromatic hydrocarbon groups such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group;
Alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group;
Aryloxy groups such as phenoxy groups;
An aralkyloxy group such as a benzyloxy group;
Acyloxy groups such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, acetoxy group, benzoyloxy group;
Methylsulfamoyl group, dimethylsulfamoyl group, ethylsulfamoyl group, diethylsulfamoyl group, n-propylsulfamoyl group, di-n-propylsulfamoyl group, isopropylsulfamoyl group, diisopropylsulfamoyl group Alkylsulfamoyl groups such as a famoyl group, n-butylsulfamoyl group, di-n-butylsulfamoyl group;
Alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
Examples thereof include a nitro group and a cyano group.
When the substituent has a hydrogen atom, the hydrogen atom is, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, or a butoxy group. , Isobutoxy group, sec-butoxy group, tert-butoxy group, alkoxy group such as pentyloxy group; aryloxy group such as phenoxy group, benzyloxy group; phenyl group, o-tolyl group, m-tolyl group, p-tolyl group An aromatic hydrocarbon group such as a group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group; carboxy group; cyano group; nitro group;

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

In the formula (2), X ³ , X ⁴ , X ⁵ and X ⁶ each independently represent a hydrogen atom or a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

R ⁹ and R ¹⁶ each independently represent a C 1-12 aliphatic hydrocarbon group or hydrogen atom 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. , Isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 1,3-butadienyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group Group, 2-pentene-4-ynyl group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group and octyl group.
Examples of the substituent in the aliphatic hydrocarbon group include:
Aromatic hydrocarbon groups such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group;
Examples thereof include alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, phenoxy group and benzyloxy group.
Halogen groups such as fluoro, chloro, bromo and iodo groups;
Furthermore, a carboxy group, a nitro group, and a cyano group are mentioned.

R ⁹ and R ¹⁶ are preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms having no substituent, and more preferably an alkyl group having 1 to 4 carbon atoms having no substituent. More preferably, it is an n-butyl group. R ⁹ and R ¹⁶ are preferably the same group. When R ⁹ and R ¹⁶ are the same group, the molar extinction coefficient tends to be better.

R ¹⁰ and R ¹¹ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, or R ¹⁰ and R ¹¹ together form an alkanediyl group. Form a group. R ¹² and R ¹³ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, or R ¹² and R ¹³ together form an alkanediyl group. Form a group. R ¹⁴ and R ¹⁵ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, or R ¹⁴ and R ¹⁵ together form an alkanediyl group. Form a group. R ¹⁷ and R ¹⁸ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, or R ¹⁷ and R ¹⁸ together form alkanediyl. Form a group. R ¹⁹ and R ²⁰ each independently represents an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, or R ¹⁹ and R ²⁰ together form an alkanediyl group. Form a group. R ²¹ and R ²² each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, or R ²¹ and R ²² together represent an alkanediyl group. Form.

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. , Isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 1,3-butadienyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group Group, 2-pentene-4-ynyl group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group and octyl group.
Examples of the substituent in the aliphatic hydrocarbon group include:
Examples thereof include alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, phenoxy group and benzyloxy group.
Halogen groups such as fluoro, chloro, bromo and iodo groups;
Furthermore, a carboxy group, a nitro group, and a cyano group are mentioned.
Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, A hexane-1,6-diyl group is mentioned.

When R ^{10 to} R ¹⁵ and R ^{17 to} R ²² each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, it preferably has a substituent. An alkyl group having 1 to 3 carbon atoms, more preferably a methyl group which may have a substituent, and still more preferably a methyl group having no substituent. 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 preferably the same group.

When R ¹⁰ and R ¹¹ 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 , A pentane-1,5-diyl group.

When 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 , A pentane-1,5-diyl group.

When R ¹⁷ and R ¹⁸ 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 , A pentane-1,5-diyl group.

When 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 , A pentane-1,5-diyl group.

  Examples of the hydrocarbon ring containing the alkanediyl group include a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. 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, an n-propyl group, and an isopropyl group. be able to.

When 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 Propane-1,5-diyl group.

When R ²¹ and R ²² 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 Propane-1,5-diyl group.

  Examples of the hydrocarbon ring containing the alkanediyl group include a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, and a cycloheptene ring. 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, an n-propyl group, and an isopropyl group. be able to.

L ₁ represents a hydrocarbon group which may have a substituent.
Examples of L ₁ include:
Aliphatic hydrocarbon groups such as methylene group, ethylene group, vinylene group, trimethylene group, propylene group, propenylene group, tetramethylene group, pentamethylene group, hexamethylene group;
Alicyclic hydrocarbon groups such as cyclopentylene group, cyclohexenylene group, cyclohexadienylene group;
and aromatic hydrocarbon groups such as o-phenylene group, m-phenylene group, p-phenylene group, and naphthylene group.

Note that, in L _1, as long as the lightness is not impaired color filter obtained from the coloring composition containing a salt of the present invention, one or more hydrogen atoms, an amino group, a carboxy group, a cyano group, a nitro group , A halogen group, a hydroxy group and the like may be substituted.
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 ease of synthesis and solubility in an organic solvent, and 3 to 3 carbon atoms. Even more preferred are 8 alkanediyl groups.

n ₂ and n ₃ each independently represents 0 or 1, and is preferably 0.

  Cation (A) represents cation (1) or cation (2), and cation (1) is preferred.

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

An anion (B) can be selected according to the color of the target color filter.
The anion (B) is preferably sufficiently dissolved in the solvent. Furthermore, the anion (B) is preferably dissolved in the developer used for pattern formation to such an extent that the pattern can be formed.

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

（式（３）は、式（４）で表される化合物に含まれるｎ個の水素原子が、−ＳＯ_３ ⁻で置換されていることを表す。ｎは１以上４以下の整数。）

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

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

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

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

  The salt which concerns on this invention can be manufactured by making a cation (A) and an anion (B) contact 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 that case, it is preferable to react the salt containing an anion (B) and the salt containing a cation (A) at a molar ratio of 1: 1 to 1: 4.

  The method for obtaining the target compound salt from the reaction mixture is not particularly limited, and various known techniques can be employed. For example, the reaction mixture can be mixed with an inorganic salt (eg, sodium chloride) and water, and the precipitated crystals can be collected by filtration. The inorganic salt is preferably prepared by preparing an aqueous solution of an inorganic salt in advance and then adding the reaction mixture to the aqueous solution. The temperature at which the reaction mixture is added is preferably 10 ° C. or higher and 50 ° C. or lower, more preferably 10 ° C. or higher and 40 ° C. or lower, and further preferably 10 ° C. or higher and 25 ° C. or lower. Moreover, after adding a reaction mixture to the aqueous solution of an inorganic salt, it is preferable to stir at the same temperature for about 0.5 to 2 hours. The crystals collected by filtration are preferably washed with water and then dried. Moreover, you may refine | purify further by well-known methods, 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 density, it is useful as a dye used for color filters, fiber materials, and the like of display devices such as liquid crystal display devices that perform color display using reflected light or transmitted light.

The dye of the present invention is a dye containing a salt of a cation (A) and an anion (B) as an active ingredient.
The colored composition of the present invention preferably contains the dye of the present invention as a colorant (hereinafter sometimes referred to as “colorant (C)”) and further contains a resin (D). More preferably, the colored composition of the present invention further contains a polymerizable compound (E), a polymerization initiator (F), and a solvent (G).

In addition to the dye of the present invention, the colorant (C) may further contain a pigment and / or a dye different from the dye of the present invention.
As dyes different from the dyes of the present invention, the Color Index (published by The Society of Dyers and Colorists), Solvent, Acid, Basic, reactive, direct And dyes classified as (Direct), Disperse, or Vat. More specifically, dyes having the following color index (CI) numbers can be mentioned, but the dye is not limited thereto.
C. I. Solvent Yellow 25, 79, 81, 82, 83, 89;
C. I. Acid Yellow 7, 23, 25, 42, 65, 76;
C. I. Reactive Yellow 2, 76, 116;
C. I. Direct yellow 4, 28, 44, 86, 132;
C. I. Disperse Yellow 54,76;
C. I. Solvent orange 41, 54, 56, 99;
C. I. Acid Orange 56, 74, 95, 108, 149, 162;
C. I. Reactive Orange 16;
C. I. Direct orange 26;
C. I. Solvent Red 24, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 160, 218;
C. I. Acid Red 73, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 102;
C. I. Solvent Green 1,5;
C. I. Acid Green 3, 5, 9, 25, 28;
C. I. Basic Green 1;
C. I. Bat Green 1 etc.

Examples of the pigment include organic pigments and inorganic pigments usually used for pigment dispersion resists. Examples of inorganic pigments include metal compounds such as metal oxides and metal complex salts. Specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and other metal compounds. Oxides or mixed metal oxides may be mentioned. Specific examples of organic pigments and inorganic pigments include compounds classified as Pigment under the Color Index (published by The Society of Dyers and Colorists). More specifically, the following color index (C.I.
) Numbered pigments, but are not limited thereto.

C. I. 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;
C. I. Pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264;
C. I. Pigment violet 14, 19, 23, 29, 32, 33, 36, 37 and 38;
C. I. Pigment Green 7, 10, 15, 25, 36, 47 and 58 etc.

The content of the colorant (C) is preferably 5 to 60% by mass with respect to the solid content in the colored composition. Here, solid content means the sum total of the component except a solvent in a coloring composition.
The content of the dye of the present invention contained in the colorant (C) is preferably 3 to 100% by mass.
Dyes and pigments different from the dye of the present invention may be used alone or in combination of two or more with the dye of the present invention.

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

  Specific examples of the resin (D) include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / isobornyl methacrylate copolymer, methacrylic acid / styrene. / Benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / styrene / glycidyl methacrylate copolymer, and the like.

The weight average molecular weight in terms of polystyrene 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 50 to 150 mg-KOH / g, more preferably 60 to 135 mg-KOH / g.
Content of resin (D) becomes like this. Preferably it is 7-65 mass% with respect to solid content of a coloring composition, More preferably, it is 13-60 mass%.

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

The polymerizable compound (E) is preferably a polymerizable compound having 3 or more polymerizable groups. Examples of the polymerizable compound having 3 or more polymerizable groups include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, and the like. Can be mentioned. The above polymerizable compounds may be used alone or in combination of two or more.
It is preferable that content of polymeric compound (E) is 5-65 mass% with respect to solid content of a coloring composition, More preferably, it is 10-60 mass%.

As said polymerization initiator (F), an active radical generator, an acid generator, etc. are mentioned. Active radical generators generate active radicals by the action of heat or light. Examples of the active radical generator include alkylphenone compounds, thioxanthone compounds, triazine compounds, and oxime compounds.
Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, Examples include benzyldimethyl ketal, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, and the like.

  Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.

  Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4 -Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl)- 6- [2- (5-Methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (Trichloromethyl 6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

  Examples of the oxime compound include O-acyloxime compounds, and specific examples thereof include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N -Benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] Ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H -Carbazol-3-yl] ethane-1-imine and the like.

  Examples of the active radical generator include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2′-bis (o-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1, 2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene compound and the like may be used.

Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, and benzyl (4-acetoxy Phenyl) methylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, onium salts such as diphenyliodonium hexafluoroantimonate, and nitrobenzyl tosylate And benzoin tosylate.
The above 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 with respect to 100 parts by mass of the total amount of the resin (D) and the polymerizable compound (E). Part by mass. When the content of the polymerization initiator is within the above range, it is preferable because the sensitivity is increased, the exposure time is shortened, and the productivity is improved.

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

  Examples of the ethers include tetrahydrofuran, tetrahydropyran, 1,4-dioxane, 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 monobutyl ether acetate and the like.

Examples of the aromatic hydrocarbons include benzene, toluene, xylene, mesitylene and the like.
Examples of the ketones include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, 4-hydroxy-4-methyl-2-pentanone, and cyclopentanone. And cyclohexanone.
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, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, and lactic acid. Ethyl, butyl lactate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxypropion Ethyl acetate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-methoxy-2-methylpropionic acid Chill, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, γ -Butyrolactone etc. are mentioned.

Examples of the amides include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
These solvents may be used alone or in combination of two or more.

  Content of the solvent (G) in a coloring composition becomes like this. Preferably it is 70-95 mass% with respect to a coloring composition, More preferably, it is 75-90 mass%.

  The coloring composition of the present invention may be added as necessary, such as surfactants, fillers, other polymer compounds, adhesion promoters, antioxidants, ultraviolet absorbers, light stabilizers, chain transfer agents, etc. An agent may be included.

The salt of the present invention is useful as a dye. Since it has a high molar extinction coefficient and shows solubility in organic solvents, it is particularly useful as a dye for use in color filters of display devices such as liquid crystal display devices.
In addition, the colored composition containing the salt of the present invention has various colored images such as a display device (for example, a known liquid crystal display device or an organic EL device) having a color filter as a part of its constituent parts, a solid-state imaging device, or the like. It can be used in a known manner for devices related to the above.

Next, the present invention will be described more specifically with reference to examples.
In Examples and Comparative Examples, “%” and “part” representing content or use amount are based on mass unless otherwise specified.

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

[Example 1]
C. I. A solution (s1) was prepared by dissolving 7.8 g of direct blue 86 (manufactured by Tokyo Chemical Industry Co., Ltd.) in 20 ml of N, N-dimethylformamide. Separately, a solution (t1) was prepared by dissolving 12.5 g of the compound represented by the following formula (d-1) in 20 ml of N, N-dimethylformamide. At 25 ° C., the solution of (s1) was added dropwise to (t1) over 1 hour, and then stirred for 2 hours. Thereafter, 100 ml of ion exchange water was added, and the mixture was further stirred for 1 hour. Then, suction filtration was performed and the product was washed with 100 ml of ion-exchanged water to obtain 10.5 g of a 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]
C. I. A solution (s3) was prepared by dissolving 7.8 g of direct blue 86 (manufactured by Tokyo Chemical Industry Co., Ltd.) in 20 ml of N, N-dimethylformamide. Separately, a solution (t2) was prepared by dissolving 6.2 g of the compound represented by the following formula (d-1) in 20 ml of N, N-dimethylformamide. At 25 ° C., the solution of (t2) was added dropwise to (s2) over 1 hour, and then stirred for 2 hours. Thereafter, 100 ml of ion exchange water was added, and the mixture was further stirred for 1 hour. Then, suction filtration was performed and the product was washed with 100 ml of ion exchange water to obtain 6.9 g of a 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
C. I. A solution (s3) was prepared by dissolving 2.5 g of direct blue 86 (manufactured by Tokyo Chemical Industry Co., Ltd.) in 20 ml of N, N-dimethylformamide. Separately, a solution (t3) was prepared by dissolving 3.5 g of the compound represented by the following formula (d-2) in 30 ml of N, N-dimethylformamide. At 25 ° C., the solution of (t3) was added dropwise to (s3) over 1 hour, and then stirred for 2 hours. Thereafter, 150 ml of ion exchange water was added, and the mixture was further stirred for 1 hour. Then, suction filtration was performed and the product was washed with 100 ml of ion exchange water to obtain 3.2 g of a 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 having a concentration of 0.028 g / L was prepared by dissolving 0.35 g of the compound in ethyl lactate to a volume of 250 cm ³ , 2 cm ^{3 of} which was diluted with ethyl lactate to 100 cm ³ . The maximum absorption wavelength (λmax) and molar extinction coefficient of the solution were measured using an ultraviolet-visible spectrophotometer (V-650DS; manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm). The results are shown in Table 1.

Example 4
[Preparation of colored composition]
(C) Colorant: Compound (I-1): Compound synthesized in Example 1 20 parts (D) Resin: Methacrylic acid / benzyl methacrylate copolymer (molar ratio; 30/70; weight average molecular weight 10700, acid value) 70 mg (KOH / g) 70 parts (E) polymerizable compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 30 parts (F) photopolymerization initiator: benzyl dimethyl ketal (Irgacure (registered trademark) 651; BASF Japan) 15 parts (G) Solvent: 680 parts of ethyl lactate are mixed to obtain a colored composition.

[Production of color filter]
On the glass, the colored composition obtained above is applied by spin coating to volatilize volatile components. After cooling, light irradiation is performed using a quartz glass photomask having a pattern and an exposure machine. After light irradiation, development is performed with an aqueous potassium hydroxide solution, and the color filter is obtained by heating to 200 ° C. in an oven.

  From the results in Table 1, it can be seen that the salt of the present invention has a high molar extinction coefficient and a high spectral concentration. Moreover, the coloring composition containing the said compound has the outstanding color performance, and can be utilized for preparation of a high quality color filter.

  The salt of the present invention is useful as a colorant. Since the salt of the present invention has a high molar extinction coefficient and a high spectral density, it is particularly useful as a colorant used in a color filter of a display device such as a liquid crystal display device.

Claims (8)

A salt containing a cation (A) derived from a cyanine compound and an anion (B) derived from a phthalocyanine compound ,
A salt in which (A) is a cation represented by formula (1) or formula (2).

(In formula (1), ring Z ¹ and ring Z ² each independently represent an aromatic ring which may have a substituent. R ¹ and R ² each independently have a substituent. Represents an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, and R ³ and R ⁴ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms. Alternatively, it represents a hydrogen atom, or R ³ and R ⁴ together form an alkanediyl group, and R ⁵ and R ⁶ each independently have 1 to 12 carbon atoms which may have a substituent. Represents an aliphatic hydrocarbon group or a hydrogen atom, or R ⁵ and R ⁶ together form an alkanediyl group, and R ⁷ and R ⁸ are each independently a carbon that may have a substituent. Represents an aliphatic hydrocarbon group of formula 1 to 12 or a hydrogen atom, or R ⁷ and R ⁸ together form an alkanediyl group X ¹ and X ² each independently represent a hydrogen atom or a halogen atom, and n 1 represents 0 or 1.)

(In Formula (2), Ring Z ³ , Ring Z ⁴ , Ring Z ⁵ and Ring Z ⁶ each independently represent an aromatic ring which may have a substituent. R ⁹ and R ¹⁶ are substituted. Represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a group or a hydrogen atom, and R ¹⁰ and R ¹¹ independently of each other have 1 to 12 carbon atoms which may have a substituent. Represents an aromatic hydrocarbon group or a hydrogen atom, or R ¹⁰ and R ¹¹ together form an alkanediyl group, and R ¹² and R ¹³ independently of each other may have a substituent. Represents an aliphatic hydrocarbon group or a hydrogen atom of 1 to 12, or R ¹² and R ¹³ together form an alkanediyl group, and R ¹⁴ and R ¹⁵ each independently have a substituent. or even represents an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms in ^{the R 14} and ^{R 15} is one .R ¹⁷ and R ¹⁸ to form an alkanediyl group is in the are, independently of one another represent an aliphatic hydrocarbon group or a hydrogen atom having 1 to 12 carbon atoms which may have a substituent, and R ¹⁷ R ¹⁸ and R ¹⁸ together form an alkanediyl group, and R ¹⁹ and R ²⁰ each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom. R ¹⁹ and R ²⁰ together form an alkanediyl group, and R ²¹ and R ²² are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. Alternatively, it represents a hydrogen atom, or R ²¹ and R ²² together form an alkanediyl group, and L ¹ represents an alkanediyl group having 1 to 12 carbon atoms which may have a substituent. ^{3, X} 4, ^{X 5} and ^{X 6,} independently of one another, a hydrogen atom The .n2 and n3 represents a halogen atom, independently of each other, represent 0 or 1.) The salt according to claim 1, wherein (A) is a cation represented by the formula (1). The salt according to claim 1 or 2 , wherein the ring Z ¹ and the ring Z ² are each independently a naphthalene ring which may have a substituent. The salt according to any one of claims 1 to 3 , wherein R ¹ and R ² are both n-butyl groups. The salt according to any one of claims 1 to 4 , wherein R ^{3 to} R ⁶ are all methyl groups. An anion (B) derived from a phthalocyanine compound is C.I. I. Direct Blue 86, C.I. I. Direct Blue 87 or C.I. I. The salt according to any one of claims 1 to 5 , which is an anion derived from Acid Blue 249. The dye which uses the salt in any one of Claims 1-6 as an active ingredient. A coloring composition comprising the dye according to claim 7 .