JP2012207070A - Salt for dye - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a salt exhibiting preferable molar absorbance coefficient, useful as such a dye in which a colored photosensitive resin composition containing a dye is known as a material for producing a color filter, since color filters are used in displays such as liquid crystal panels, electroluminescent panels and plasma display panels; to provide a dye containing the salt as an active component; and a colored resin composition containing the dye.SOLUTION: This salt comprises an anion and a cation expressed by formula (1).

Description

  The present invention relates to a salt represented by the formula (1), 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. Colored photosensitive resin compositions containing dyes are known as materials for producing color filters. . As a dye contained in such a colored photosensitive resin composition, a triphenylmethane compound (0-1) as described in Example 1 of Patent Document 1 is known.

Japanese Patent Laid-Open No. 5-229993

  As described above, the triphenylmethane compound is not always satisfactory in terms of its molar extinction coefficient.

［式（1）中、Ｇ^１は炭素数２〜１２のアルキレン基を表し、該アルキレン基に含まれる−ＣＨ_２−は、−Ｏ−で置き換わっていてもよい。Ｒ^１及びＲ^２は、それぞれ独立に、水素原子又は炭素数１〜８のアルキル基を表し、ｎ^ａは、１〜４の整数を表す。
Ｒ_３〜Ｒ_６は、それぞれ独立に、水素原子；群Ｐ１から選ばれる基を有していてもよい炭素数１〜８のアルキル基；群Ｐ２から選ばれる基を有していてもよい炭素数６〜１０の芳香族炭化水素基を表す。Ｒ^７〜Ｒ^９は、それぞれ独立に、水素原子、炭素数１〜８のアルキル基、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＳＯ_３ ⁻Ｍ^＋を表す。Ｒcは、−ＮＲ^１０Ｒ^１１、−ＣＲ^１２Ｒ^１３、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＳＯ_３ ⁻Ｍ^＋を表す。Ｒ^１０〜Ｒ^１３は、それぞれ独立に、水素原子；群Ｐ１から選ばれる基を有していてもよい炭素数１〜８のアルキル基；群Ｐ２から選ばれる基を有していてもよい炭素数６〜１０の芳香族炭化水素基を表す。
群Ｐ１は、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、および−ＳＯ_３ ⁻Ｍ^＋からなり、
群Ｐ２は、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＳＯ_３ ⁻Ｍ^＋および炭素数１〜８のアルコキシ基からなり、Ｍ^＋は、Ｎａ^＋、Ｋ^＋を表す。]
［２］ Ｒ^１およびＲ^２が、メチル基である［１］記載の塩。
［３］ Ｇ^１が、プロピレン基である［１］又は［２］記載の塩。
［４］ ｎ^ａが、３である［１］〜［３］のいずれかに記載の塩。
［５］ Ｒcが、−ＮＲ^１０Ｒ^１１である［１］〜［４］のいずれかに記載の塩。
［６］ Ｒ^５及びＲ^１０が、−ＳＯ_３ ⁻を有するベンジル基であり、Ｒ^６及びＲ^１１が、エチル基である［１］〜［５］のいずれかに記載の塩。
［７］ Ｒ^８及びＲ^９が、エチル基であり、Ｒ^７が水素原子である［１］〜［６］のいずれかに記載の塩。
［８］ ［１］〜［７］のいずれかに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 [10].
[1] A salt represented by the following formula (1).

[In Formula (1), G ¹ represents an alkylene group having 2 to 12 carbon atoms, and —CH ₂ — contained in the alkylene group may be replaced by —O—. R ¹ and ^{R 2} each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, ^{n a} represents an integer of 1 to 4.
R _{3 to} R ₆ are each independently a hydrogen atom; an alkyl group having 1 to 8 carbon atoms that may have a group selected from group P1; and a carbon that may have a group selected from group P2. The aromatic hydrocarbon group of several 6-10 is represented. R ⁷ to R ⁹ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon _atoms, ^-SO 3 _- representing the ^{M + -, -SO 3 H,} -SO 3. Rc ^{is, -NR 10 R 11, -CR 12} R 13, -SO 3 -, -SO 3 H, -SO 3 - represents an ^{M +.} R ^{10 to} R ¹³ are each independently a hydrogen atom; an alkyl group having 1 to 8 carbon atoms that may have a group selected from group P1; and a carbon that may have a group selected from group P2. The aromatic hydrocarbon group of several 6-10 is represented.
Group P1 _{^{is, -SO 3 -, -SO 3 H}} , and _-SO ³ - consists ^{M +,}
Group P2 _{^{is, -SO 3 -, -SO 3 H}} , -SO 3 - consists ^{M +} and alkoxy group having 1 to 8 carbon atoms, ^{M + is,} Na +, representative of ^{K +.} ]
[2] The salt according to [1], wherein R ¹ and R ² are methyl groups.
[3] The salt according to [1] or [2], wherein G ¹ is a propylene group.
[4] ^{n a} is A salt according to any one of a 3 [1] to [3].
[5] Rc ^is, salts according to any one of the ^{-NR 10 R 11 [1] ~} [4].
[6] The salt according to any one of [1] to [5], wherein R ⁵ and R ¹⁰ are benzyl groups having —SO ₃ ^— , and R ⁶ and R ¹¹ are ethyl groups.
[7] The salt according to any one of [1] to [6], wherein R ⁸ and R ⁹ are an ethyl group, and R ⁷ is a hydrogen atom.
[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 according to the present invention has a good molar extinction coefficient.

The salt of the present invention includes a cation represented by the following formula (A) (hereinafter sometimes referred to as “cation (A)”) and an anion represented by the following formula (B) (hereinafter referred to as “anion (B)”). Is a salt consisting of.

  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.

  In addition, since the cation (A) has a resonance structure, a cation in which the charge of the cation in the formula (1) is transferred is also included in the present invention. Further, the cation (A) is +2 as a whole cation.

In the cation (A), G ¹ is preferably an alkylene group having 2 to 8 carbon atoms, more preferably an alkylene group having 2 to 4 carbon atoms, from the viewpoint of solubility.

Preferred alkylene groups as G ¹ include a methylene group, an ethylene group, a propylene group, a butylene group, and the like. Among these, a propylene group is preferable.

In the cation (A), as —CH ₂ — contained in the alkylene group of G ¹ is replaced by —O—, for example, a group represented by the formula (G-1) and a formula (G-2) Group to be used.

［式（Ｇ−１）及び式（Ｇ−２）中、Ｇ^２〜Ｇ^５は、それぞれ独立に、炭素数１〜８のアルキレン基を表す。
ｎ^１及びｎ^２は、１〜３の整数を表す。
ただし、式（Ｇ−１）で表される基及び式（Ｇ−１）で表される基に含まれる炭素原子
及び酸素原子の合計数は、ぞれぞれ２〜１２である。 ＊は、−ＮＨ−との結合手を表す。］

[In Formula (G-1) and Formula (G-2), G ^{2 to} G ⁵ each independently represents an alkylene group having 1 to 8 carbon atoms.
n ¹ and ^{n 2} represents an integer of 1 to 3.
However, the total number of carbon atoms and oxygen atoms contained in the group represented by Formula (G-1) and the group represented by Formula (G-1) is 2 to 12, respectively. * Represents a bond with -NH-. ]

Next, R ^{3 to} R ⁶ of the cation (A) will be described with specific examples.
In the cation (A), examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, and a butyl group.

  In the cation (A), examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl group, tolyl group, xylyl group, mesityl group, cumenyl group, benzyl group, and phenethyl group.

From the viewpoint of improving solubility, R ¹ and R ² are preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group. R ¹ and R ² are preferably the same group.

In the cation (A), examples of —SO ₂ —NH—G ¹ -J ¹ include groups represented by the following formulae.

Ｇ^１が、式（Ｇ−１）で表される基である場合、−ＳＯ_２−ＮＨ−Ｇ^１−Ｊ^１としては
、例えば下記式で表される基が挙げられる。

When G ¹ is a group represented by the formula (G-1), examples of —SO ₂ —NH—G ¹ -J ¹ include a group represented by the following formula.

When G ¹ is a group represented by the formula (G-2), examples of —SO ₂ —NH—G ¹ -J ¹ include a group represented by the following formula.

When J ¹ is —NR ^a R ^b , examples of —SO ₂ —NH—G ¹ —J ¹ include groups represented by the following formulae.

N ^a cation (A) is an integer of 1 to 4, from the viewpoint of the solubility of the salt enhancing containing cation (A), n ^a is 3 are preferred.

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.

  In addition, since an anion (B) takes a resonance structure, the anion which the electric charge in Formula (1) moved is also contained in this invention. The anion (B) is −1 as a whole anion.

［式（２）中、Ｒ^３〜Ｒ^１１は、それぞれ式（１）と同じ定義である。］ From the viewpoint of improving the solubility of the salt containing the anion (B), Rc is preferably —NR ¹⁰ R ¹¹ in the anion (B). The anion (B) is represented by the formula (2) (hereinafter sometimes referred to as “anion (2)”).

[In Formula (2), R < ³ > -R < ¹¹ > is the same definition as Formula (1), respectively. ]

［式（４）中、＊は、Ｎ−との結合手を表す。］
Ｒ^１０及びＲ^１１の他方は、置換基を有さない炭素数１〜８のアルキル基が好ましく、エチル基がより好ましい。 In the anion ^(2), one of ^{R 10} and ^{R 11,} -SO ₃ ^- preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms having, -SO ₃ ^- and more preferably a benzyl group having the formula The group represented by (3) is particularly preferred.

[In formula (4), * represents a bond with N-. ]
The other of R ¹⁰ and R ¹¹ is preferably a C 1-8 alkyl group having no substituent, and more preferably an ethyl group.

In the anion (2), one of ^{R 5} and ^{R 6,} -SO ₃ ^- preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms having, -SO ₃ ^- and more preferably a benzyl group having the formula The group represented by (4) is particularly preferred.
The other of R ⁵ and R ⁶ is preferably a C 1-8 alkyl group having no substituent, and more preferably an ethyl group.

From the viewpoint of solubility, R ⁷ is preferably a hydrogen atom, and R ⁸ and R ⁹ are each independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and more preferably an ethyl group.

［式（４）中、Ｒ^５〜Ｒ^１１は、それぞれ式（１）と同じ定義である。］ In the anion (2), any one of R ³ and R ⁴ is preferably an aromatic ring which may have an alkoxy group having 1 to 8 carbon atoms, and more preferably a benzene ring having an ethoxy group. The other of R ³ and R ⁴ is preferably a hydrogen atom. The anion (2) is preferably an anion represented by the formula (4) (hereinafter sometimes referred to as “anion (4)”) from the viewpoint of improving the solubility of the salt containing the anion (2).

[In Formula (4), R < ⁵ > -R < ¹¹ > is the same definition as Formula (1), respectively. ]

  In the anion (B), the alkyl group having 1 to 8 carbon atoms includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, and isopentyl group. , Neopentyl group, tert-pentyl group and the like.

  In the anion (B), the aromatic hydrocarbon group having 6 to 10 carbon atoms includes phenyl group, tolyl group, xylyl group, mesityl group, cumenyl group, benzyl group, phenethyl group, α-methylbenzyl group, benzhydryl group, Examples include a benzylidene group, a styryl group, a cinnamyl group, a cinnamylidene group, and a naphthyl group.

  In the anion (B), examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and a pentyloxy group. Is mentioned.

In the anion (B), examples of M ⁺ include Na ⁺ and K ⁺ .

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

  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 according to the present invention can be produced by subjecting a salt containing a cation (A) and a salt containing an anion (B) to a salt exchange reaction in a solvent. It is preferable to react the salt containing the cation (A) and the salt containing the anion (B) at a molar ratio of 1: 1 to 4: 1.

  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, it is preferable that the reaction mixture is mixed with an inorganic salt (for example, sodium chloride) and water, and the precipitated crystals are 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, the compound of the present invention 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 performs color display using reflected light or transmitted light.

The dye of the present invention is a dye containing a cation (A) and an anion (B) as active ingredients.
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, and more preferably 60 to 135.
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 photopolymerizable compound having 3 or more polymerizable groups. Examples of the photopolymerizable compound having 3 or more polymerizable groups include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate and the like. Is mentioned. The photopolymerizable compound (E) 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, 4-acetoxyphenyl, Onium salts such as methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyl tosylate And benzoin tosylate.
The polymerization initiators (F) 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, the structure of the compound was confirmed by elemental analysis (VARIO-EL; (Elemental Co., Ltd.)).

[Example 1]
C. I. Astra Blue base 6GLL (1-1), 1.67 parts were mixed with 40 parts of a 5% weight ratio acetic acid aqueous solution and sufficiently stirred to prepare a completely dissolved astrouble solution (s1). In a separate container, 1.80 parts of triphenylmethane dye (2-1) was mixed with 60 parts of an acetic acid aqueous solution having a 5% weight ratio and sufficiently stirred to prepare a completely dissolved solution (t1). C. at 25 ° C. I. The Astra Blue base 6GLL solution (s1) was added dropwise to the prepared liquid (t1) little by little, and then stirred at 20 to 30 ° C. for 2 to 3 hours. Thereafter, 100 parts of ultrapure water was added and stirred for an additional hour. Thereafter, suction filtration was carried out, followed by washing with 5% by weight acetic acid aqueous solution and then with water. The salt-forming compound that was washed with methanol and remained on the filter paper was dried by removing moisture with a dryer, and 2.3 parts of the salt represented by the formula (I-1) was obtained.

Identification of the compound represented by formula (I-1);
(Elemental analysis) C: 58.9 H: 5.1 N: 12.3 Cu: 3.8 S: 9.0

<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.

〔実施例２〕
［着色組成物の調製］
（Ｃ）着色剤：化合物（Ｉ−１）：実施例１で合成した化合物 ２０部
（Ｄ）樹脂：メタクリル酸／ベンジルメタクリレート共重合体（モル比；３０／７０；重量平均分子量１０７００、酸価７０ｍｇＫＯＨ／ｇ） ７０部
（Ｅ）重合性化合物：ジペンタエリスリトールヘキサアクリレート（日本化薬社製） ３０部
（Ｆ）光重合開始剤：ベンジルジメチルケタール（イルガキュア６５１；チバ・ジャパン社製） １５部
（Ｇ）溶剤：乳酸エチル ６８０部
を混合して着色組成物を得る。

[Example 2]
[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 parts (E) polymerizable compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 30 parts (F) photopolymerization initiator: benzyldimethyl ketal (Irgacure 651; manufactured by Ciba 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 compound of the present invention has a high absorbance because of its high absorbance. Moreover, the coloring composition containing the said compound has the outstanding color performance, and it is possible to produce 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 (9)

A salt represented by the following formula (1).

[In Formula (1), G ¹ represents an alkylene group having 2 to 12 carbon atoms, and —CH ₂ — contained in the alkylene group may be replaced by —O—. R ¹ and ^{R 2} each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, ^{n a} represents an integer of 1 to 4.
R ^{3 to} R ⁶ are each independently a hydrogen atom; an alkyl group having 1 to 8 carbon atoms that may have a group selected from group P1; and a carbon that may have a group selected from group P2. The aromatic hydrocarbon group of several 6-10 is represented. R ⁷ to R ⁹ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon _atoms, ^-SO 3 _- representing the ^{M + -, -SO 3 H,} -SO 3. Rc ^{is, -NR 10 R 11, -CR 12} R 13, -SO 3 -, -SO 3 H, -SO 3 - represents an ^{M +.} R ^{10 to} R ¹³ are each independently a hydrogen atom; an alkyl group having 1 to 8 carbon atoms that may have a group selected from group P1; and a carbon that may have a group selected from group P2. The aromatic hydrocarbon group of several 6-10 is represented.
Group P1 _{^{is, -SO 3 -, -SO 3 H}} , and _-SO ³ - consists ^{M +,}
Group P2 _{^{is, -SO 3 -, -SO 3 H}} , -SO 3 - consists ^{M +} and alkoxy group having 1 to 8 carbon atoms, ^{M + is,} Na +, representative of ^{K +.} ] The salt according to claim 1, wherein R ¹ and R ² are methyl groups. The salt according to claim 1 or 2, wherein G ¹ is a propylene group. n ^a is A salt according to claim 1 which is 3. Rc ^is, salts according to any of claims 1 to 4 is ^-NR 10 ^{R 11.} R ⁵ and ^{R 10,} -SO ₃ ^- a benzyl group having, ^{R 6} and ^{R 11} is A salt according to claim 1 is an ethyl group. The salt according to any one of claims 1 to 6, wherein R ⁸ and R ⁹ are an ethyl group, and R ⁷ is a hydrogen atom.   A dye comprising the salt according to any one of claims 1 to 7 as an active ingredient.   A coloring composition comprising the dye according to claim 8.