JP2011148992A - Compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having a high molar extinction coefficient and high spectral density. <P>SOLUTION: The compound is expressed by formula (0). In formula (0), R<SP>1</SP>represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms or the like; R<SP>2</SP>represents a hydrogen atom, -CN or the like; R<SP>3</SP>represents an alkyl group having 1 to 4 carbon atoms or the like; R<SP>4a</SP>to R<SP>7a</SP>each represents -R<SP>8</SP>, -COOR<SP>8</SP>, -CN or the like; R<SP>8</SP>represents a hydrogen atom, an aliphatic hydrocarbon group or the like; and A<SP>+</SP>represents a sodium cation or the like. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to compounds useful as dyes.

  Conventionally, a dye of a metal complex salt compound has been used for color display using reflected light or transmitted light in various fields (for example, fiber materials, liquid crystal display devices, etc.). Examples of such a dye include C.I. represented by the following formula, which is a dye of a chromium complex having an azo compound as a ligand. I. Solvent Yellow 21 is widely known.

Industrial Dies Chemistry, Properties, Applications, WILEY-VCH, 2003.

  Conventionally known compounds described above have a small molar extinction coefficient and are not sufficiently satisfactory in terms of spectral concentration.

The present invention provides the following [1] to [7].
[1] A compound represented by the formula (0).

Wherein (0), R ¹ represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, hydrogen atoms contained in the saturated hydrocarbon ^{group, -OR 8, -COOR 8, -OCOR} 8 , -CONR ⁸ R ⁹ , a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and —O— among —CH ₂ — contained in the saturated hydrocarbon group Unbonded —CH ₂ — may be replaced by —CO—.
R ² represents a hydrogen atom, —CN, or —CONH ₂ .
R ³ represents an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
R ^{4a to} R ^7a are independently of each other, —R ⁸ , —OR ⁸ , —COOR ⁸ , —COR ⁸ , —OCOOR ⁸ , —OCOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, It represents a _{-SO 3 Na, -SO 3 K,} -SO 2 NR 8 R 9 or ^-NR 11 ^{R 12.} R ^4a and R ^5a , R ^5a and R ^6a , and R ^6a and R ^7a may be bonded to each other to form a 6- to 7-membered ring containing carbon of a benzene ring.
R ⁸ and R ⁹ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a monovalent aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon group, and a hydrogen atom contained in the aliphatic hydrocarbon group, the aralkyl group and the aromatic hydrocarbon group may be substituted with -OR ¹⁰ .
R ¹⁰ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
R ¹¹ and R ¹² each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, or a tetrahydrofurfuryl group. R ¹¹ and R ¹² may be bonded to each other to form a ring containing a nitrogen atom.
A ⁺ represents a hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms. ]

[2] A compound represented by the formula (I).

[In the formula (I), R ¹ represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group is —OR ⁸ , —COOR ⁸ , —OCOR ^8. , -CONR ⁸ R ⁹ , a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and —O— among —CH ₂ — contained in the saturated hydrocarbon group Unbonded —CH ₂ — may be replaced by —CO—.
R ² represents a hydrogen atom, —CN or —CONH ₂ .
R ³ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
R ^{4 to} R ⁷ are independently of each other —R ⁸ , —OR ⁸ , —COOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, —SO ₃ Na, —SO ₃ K, or —SO. ₂ represents NR ⁸ R ⁹
R ⁸ and R ⁹ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a monovalent aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon group, and a hydrogen atom contained in the aliphatic hydrocarbon group, the aralkyl group and the aromatic hydrocarbon group may be substituted with -OR ¹⁰ .
R ¹⁰ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
A ⁺ represents a hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms. ]

[3] The compound according to [1] or [2] above, wherein R ¹ is a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms which may be substituted with —OH or —OCOR ⁸ .
[4] The compound according to any one of [1] to [3], wherein at least three of R ^{4a to} R ^7a are hydrogen atoms, or at least three of R ^{4 to} R ⁷ are hydrogen atoms. is there.
[5] The compound according to any one of [1] to [4], wherein R ² is —CN.
[6] A dye comprising the compound according to any one of [1] to [5] as an active ingredient.
[7] A colored resin composition comprising the dye, resin and solvent according to [6] above.

  The compound of the present invention has a high molar extinction coefficient and a high spectral concentration.

  The compound of the present invention is a compound represented by the formula (0) (hereinafter sometimes referred to as “compound (0)”). The compounds of the present invention also include tautomers thereof.

Wherein (0), R ¹ represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, hydrogen atoms contained in the saturated hydrocarbon ^{group, -OR 8, -COOR 8, -OCOR} 8 , -CONR ⁸ R ⁹ , a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and —O— among —CH ₂ — contained in the saturated hydrocarbon group Unbonded —CH ₂ — may be replaced by —CO—.
R ² represents a hydrogen atom, —CN, or —CONH ₂ .
R ³ represents an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
R ^{4a to} R ^7a are independently of each other, —R ⁸ , —OR ⁸ , —COOR ⁸ , —COR ⁸ , —OCOOR ⁸ , —OCOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, It represents a _{-SO 3 Na, -SO 3 K,} -SO 2 NR 8 R 9 or ^-NR 11 ^{R 12.} R ^4a and R ^5a , R ^5a and R ^6a , and R ^6a and R ^7a may be bonded to each other to form a 6- to 7-membered ring containing carbon of a benzene ring.
R ⁸ and R ⁹ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a monovalent aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon group, and a hydrogen atom contained in the aliphatic hydrocarbon group, the aralkyl group and the aromatic hydrocarbon group may be substituted with -OR ¹⁰ .
R ¹⁰ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
R ¹¹ and R ¹² each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, or a tetrahydrofurfuryl group. R ¹¹ and R ¹² may be bonded to each other to form a ring containing a nitrogen atom.
A ⁺ represents a hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms. ]

  The compound of the present invention is preferably a compound represented by the formula (I) (hereinafter sometimes referred to as “compound (I)”).

[In the formula (I), R ¹ represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group is —OR ⁸ , —COOR ⁸ , —OCOR ^8. , -CONR ⁸ R ⁹ , a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and —O— among —CH ₂ — contained in the saturated hydrocarbon group Unbonded —CH ₂ — may be replaced by —CO—.
R ² represents a hydrogen atom, —CN or —CONH ₂ .
R ³ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
R ^{4 to} R ⁷ are independently of each other —R ⁸ , —OR ⁸ , —COOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, —SO ₃ Na, —SO ₃ K, or —SO. ₂ represents NR ⁸ R ⁹
R ⁸ and R ⁹ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a monovalent aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon group, and a hydrogen atom contained in the aliphatic hydrocarbon group, the aralkyl group and the aromatic hydrocarbon group may be substituted with -OR ¹⁰ .
R ¹⁰ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
A ⁺ represents a hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms. ]

R ¹ is a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, preferably a monovalent saturated hydrocarbon group having 1 to 6 carbon atoms, and monovalent saturated carbon group having 1 to 4 carbon atoms. A hydrogen group is more preferable, a monovalent saturated hydrocarbon group having 2 to 4 carbon atoms is further preferable, and a monovalent saturated hydrocarbon group having 2 or 4 carbon atoms is particularly preferable.
Further, when a hydrogen atom contained in the saturated hydrocarbon group is substituted, it may be substituted with —OR ⁸ , —OCOR ⁸ or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms. Preferably, when substituted with —OR ⁸ , R ⁸ is preferably a hydrogen atom, and when substituted with —OCOR ⁸ , R ⁸ is a monovalent aliphatic hydrocarbon group having 6 to ⁸ carbon atoms. Or it is preferable that it is a phenyl group.

Examples of the monovalent saturated hydrocarbon group having 1 to 8 carbon atoms in R ¹ and R ¹⁰ include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, a linear saturated hydrocarbon group such as an n-heptyl group and an n-octyl group;
Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1- Methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-propylbutyl Group, 1- (1-methylethyl) butyl group, 1- (1-methylethyl) -2-methylpropyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group Group, 5-methylheptyl group, 6-methylheptyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl 4-ethylhexyl group, 1-n-propylpentyl group, 2-propylpentyl group, 1- (1-methylethyl) pentyl group, 1-butylbutyl group, 1-butyl-2-methylbutyl group, 1-butyl-3 -Methylbutyl group, 1- (1,1-dimethylethyl) butylbutyl group, tert-butyl group, 1,1-dimethylpropyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3- Dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethyl-2-methylpropyl group, 1,1-dimethylpentyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentyl group, 1,4- Dimethylpentyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethylpentyl group, 3,4-dimethyl Rupentyl group, 1-ethyl-1-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-3-methylbutyl group, 2-ethyl-1-methylbutyl group, 2-ethyl-3-methylbutyl group, 1, 1-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group, 2,2-dimethylhexyl group, 2,3- Dimethylhexyl group, 2,4-dimethylhexyl group, 2,5-dimethylhexyl group, 3,3-dimethylhexyl group, 3,4-dimethylhexyl group, 3,5-dimethylhexyl group, 4,4-dimethylhexyl Group, 4,5-dimethylhexyl group, 1-ethyl-2-methylpentyl group, 1-ethyl-3-methylpentyl group, 1-ethyl-4-methylpentyl group 2-ethyl-1-methylpentyl group, 2-ethyl-2-methylpentyl group, 2-ethyl-3-methylpentyl group, 2-ethyl-4-methylpentyl group, 3-ethyl-1-methylpentyl group 3-ethyl-2-methylpentyl group, 3-ethyl-3-methylpentyl group, 3-ethyl-4-methylpentyl group, 1-propyl-1-methylbutyl group, 1-propyl-2-methylbutyl group, 1 -Propyl-3-methylbutyl group, 1- (1-methylethyl) -1-methylbutyl group, 1- (1-methylethyl) -2-methylbutyl group, 1- (1-methylethyl) -3-methylbutyl group, Branched saturated hydrocarbon groups such as 1,1-diethylbutyl group and 1,2-diethylbutyl group;
Examples thereof include cyclic saturated hydrocarbon groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group.

As the monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms in R ⁸ and R ⁹ , in addition to the groups mentioned in the above-mentioned linear saturated hydrocarbon group and branched saturated hydrocarbon group, a vinyl group, Examples include a propenyl group, an isopropenyl group, a butenyl group, and a 2-methylpropenyl group.
Examples of the aralkyl group having 7 to 12 carbon atoms in R ⁸ and R ⁹ include a benzyl group, a phenylethyl group, a phenylpropyl group, a naphthylmethyl group, and a naphthylethyl group.
Examples of the monovalent aromatic hydrocarbon group having 6 to ¹⁰ carbon atoms in R ⁸ , R ⁹ and R ¹⁰ include a phenyl group, a toluyl group, a xylyl group and a naphthyl group.

Examples of the saturated hydrocarbon group in which —CH ₂ — is replaced by —CO— include, for example, an acetyl group, a 3-oxobutyl group, a 2-oxobutyl group, a 3-oxopentyl group, a 2-oxopentyl group, and a 3-oxohexyl group. An oxo group-containing saturated hydrocarbon group such as
Phenacyl group, 2-oxo-2-naphthylethyl group, 2-oxo-2-hydroxyphenylethyl group, 2-oxo-2-hydroxynaphthylethyl group, 2-oxo-2-methoxyphenylethyl group, 2-oxo- Examples include 2-methoxynaphthylethyl group, 2-oxo-3-phenylpropyl group, 2-oxo-3-naphthylpropyl group aromatic hydrocarbon group and oxo group-containing saturated hydrocarbon group.

  Examples of the saturated hydrocarbon group in which a hydrogen atom is substituted with a halogen atom include a fluoromethyl group, a trifluoromethyl group, a fluoromethyl group, a fluoropropyl group, a fluorobutyl group, a chloromethyl group, a chloroethyl group, and a chloropropyl group. Chlorobutyl group, bromomethyl group, bromoethyl group, bromopropyl group, bromobutyl group, iodomethyl group, iodoethyl group, iodopropyl group, iodobutyl group and the like.

As —OR ⁸ , for example, hydroxy group, methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, phenoxy group, benzyloxy Group, benzoyloxy group and the like.
Examples of —OR ⁸ substituted with —OR ¹⁰ include methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, methoxypentyl group, 1-ethoxypropyl group, 2-ethoxypropyl group, 1- Ethoxy-1-methylethyl group, 1-methyl-2-ethoxyethyl group, 1- (1-methylethoxy) propyl group, 2- (1-methylethoxy) propyl group, 1- (1-methylethoxy) -1 -Methylethyl group, 2- (1-methylethoxy) -1-methylethyl group, 3-ethoxypropyl group and the like can be mentioned.

Examples of the saturated hydrocarbon group in which a hydrogen atom is substituted with —OR ⁸ include, for example, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxymethoxymethyl group, a 2-hydroxyethoxymethyl group, 2- Hydroxy group-containing saturated hydrocarbon groups such as hydroxymethoxyethyl group, 2- (2-hydroxyethoxy) ethyl group, 2-oxo-4-hydroxybutyl group;
Contains alkoxy groups such as methoxymethyl group, ethoxymethyl group, propoxymethyl group, methoxyethyl group, ethoxyethyl group, propoxyethyl group, methoxypropyl group, ethoxypropyl group, propoxypropyl group, 2-oxo-4-methoxybutyl group Saturated hydrocarbon groups;
Methoxymethoxymethyl group, 2-methoxyethoxymethyl group, ethoxymethoxymethyl group, 2-ethoxyethoxymethyl group, propoxymethoxymethyl group, 2-propoxyethoxymethyl group, 2-methoxymethoxyethyl group, 2- (2-methoxyethoxy ) Saturated hydrocarbon groups containing alkoxyalkyl groups such as ethyl group, 2-ethoxymethoxyethyl group, 2- (2-ethoxyethoxy) ethyl group, 2-propoxymethoxyethyl group, 2- (2-propoxyethoxy) ethyl group;
Phenyloxymethyl group, 1-naphthyloxymethyl group, 2-naphthyloxymethyl group, hydroxyphenyloxymethyl group, hydroxynaphthyloxymethyl group, methoxyphenyloxymethyl group, methoxynaphthyloxymethyl group, 3-phenoxy-2-oxo Aryloxy group-containing saturated hydrocarbon group such as propyl group;
Aralkyloxy groups such as benzyloxymethyl group, naphthylmethoxymethyl group, hydroxybenzyloxymethyl group, hydroxynaphthylmethoxymethyl group, methoxybenzyloxymethyl group, methoxynaphthylmethoxymethyl group, phenyloxyethoxymethyl group, naphthyloxyethoxymethyl group Examples thereof include saturated hydrocarbon groups.

Examples of —COOR ⁸ include a methoxycarbonyl group, an ethoxycarbonyl group, and a benzyloxycarbonyl group.

Examples of the saturated hydrocarbon group in which a hydrogen atom is substituted with —COOR ⁸ include a carboxy group-containing saturated hydrocarbon group such as a carboxymethyl group, a carboxyethyl group, a carboxypropyl group, and a carboxybutyl group;
Methoxycarbonylmethyl group, methoxycarbonylethyl group, ethoxycarbonylmethyl group, ethoxycarbonylethyl group, propoxycarbonylmethyl group, propoxycarbonylethyl group, butoxycarbonylmethyl group, butoxycarbonylethyl group, phenoxymethoxycarbonylmethyl group, 2-hydroxyethoxy Alkoxycarbonyl group-containing saturated hydrocarbon group such as carbonylmethyl group, 2-methoxyethoxycarbonylmethyl group, etc .;
Aryloxycarbonyl-containing saturated hydrocarbon groups such as phenoxycarbonylmethyl group and naphthyloxycarbonylmethyl group;
Aralkyloxycarbonyl-containing saturated hydrocarbon groups such as benzyloxycarbonylmethyl group and naphthylmethoxycarbonylmethyl group;
2-oxopropoxycarbonylmethyl group, 2- (2-oxopropoxycarbonyl) ethyl group, 3- (2-oxopropoxycarbonyl) propyl group, 2-oxobutoxycarbonylmethyl group, 2- (2-oxobutoxycarbonyl) ethyl Group, 3- (2-oxobutoxycarbonyl) propyl group, 2-oxopentyloxycarbonylmethyl group, 2- (2-oxopentyloxycarbonyl) ethyl group, 3- (2-oxopentyloxycarbonyl) propyl group, 3 -Oxobutoxycarbonylmethyl group, 2- (3-oxobutoxycarbonyl) ethyl group, 3- (3-oxobutoxycarbonyl) propyl group, 3-oxopentyloxycarbonylmethyl group, 2- (3-oxopentyloxycarbonyl) Ethyl group, 3- (3-oxope It is -CO - chill oxycarbonyl) propyl group, 2-oxo-hexyl oxycarbonyl methyl group, 2- (2-oxo-hexyl oxycarbonyl) ethyl group, 3- (2-oxo-hexyl oxycarbonyl) -CH ₂ and propyl group A saturated hydrocarbon group containing an alkoxycarbonyl group replaced with-;
3-methoxycarbonyl-2-oxopropyl group, 4-methoxycarbonyl-3-oxobutyl group, 5-methoxycarbonyl-4-oxopentyl group, 3-ethoxycarbonyl-2-oxopropyl group, 4-ethoxycarbonyl-3- Oxobutyl group, 5-ethoxycarbonyl-4-oxopentyl group, 3-propoxycarbonyl-2-oxopropyl group, 4-propoxycarbonyl-3-oxobutyl group, 5-propoxycarbonyl-4-oxopentyl group, 4-methoxycarbonyl 2-oxobutyl group, 4-methoxycarbonyl-3-oxopentyl group, 5-methoxycarbonyl-4-oxohexyl group, 4-ethoxycarbonyl-2-oxobutyl group, 4-ethoxycarbonyl-3-oxopentyl group, 5 -Ethoxycarbonyl-4 Oxo-hexyl group, 4-propoxycarbonyl-2-oxobutyl group, 4-propoxycarbonyl-3-oxopentyl group, and a content alkoxycarbonyl groups such as 5-propoxycarbonyl-4-oxo-hexyl group -CH ₂ - is -CO A saturated hydrocarbon group replaced by-; and the like.

Examples of the saturated hydrocarbon group in which a hydrogen atom is substituted with —CONR ⁸ R ⁹ include, for example, N-methylaminocarbonylmethyl group, N-methylaminocarbonylethyl group, N, N-dimethylaminocarbonylmethyl group, N, Alkyl-substituted carbamoyl group-containing saturated hydrocarbon groups such as N-dimethylaminocarbonylethyl group, N, N-ethylmethylaminocarbonylmethyl group, N, N-ethylmethylcarbonylethyl group;
Aryl-substituted carbamoyl group-containing saturated hydrocarbon groups such as N-phenylaminocarbonylmethyl group, N, N-phenylmethylcarbonylmethyl group, N, N-diphenylcarbonylmethyl group, N, N-phenylbenzylcarbonylmethyl group;
Aralkyl group-substituted carbamoyl group-containing saturated hydrocarbon group such as N-benzylaminocarbonylmethyl group, N, N-dibenzylcarbonylmethyl group, N, N-bis (2-phenylethyl) carbonylmethyl group; and the like.

Examples of —OCOR ⁸ include an acetyloxy group, a pivaloyloxy group, and a benzoyloxy group.

Examples of the saturated hydrocarbon group in which the hydrogen atom is substituted with —OCOR ⁸ include acetyloxymethyl group, acetyloxyethyl group, ethylcarbonyloxymethyl group, ethylcarbonyloxyethyl group, propylcarbonyloxymethyl group, propylcarbonyl Oxyethyl, butylcarbonyloxymethyl, butylcarbonyloxyethyl, hexanoyloxyethyl, 2-ethylbutyryloxyethyl, 2-ethylhexanoyloxyethyl, 2-propylhexanoyloxyethyl, Alkylcarbonyloxy group-containing saturated hydrocarbon groups such as valoyloxyethyl group and 2-methylpropionyloxyethyl group;
Benzoyloxymethyl group, benzoyloxyethyl group, naphthyloxycarbonylmethyl group, benzylcarbonyloxymethyl group, naphthylmethylcarbonyloxymethyl group, methylbenzoyloxymethyl group, 2-methylbenzoyloxyethyl group, 4-methylbenzoyloxyethyl group 3,4-dimethylbenzoyloxyethyl group, hydroxybenzoyloxymethyl group, methoxybenzoyloxymethyl group, 4-methoxybenzoyloxyethyl group, 3,4-dimethoxybenzoyloxyethyl group and other aromatic hydrocarbon groups and carbonyloxy And group-containing saturated hydrocarbon groups.

Examples of —COR ⁸ include an acetyl group, a propionyl group, an isobutyryl group, a valeryl group, and an isovaleryl group.
-OCOOR ⁸ includes, for example, methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, isopropoxycarbonyloxy group, n-butoxycarbonyloxy group, isobutoxycarbonyloxy group, sec-butoxycarbonyloxy group , N-pentyloxycarbonyloxy group, phenoxycarbonyloxy group and the like.

  Examples of the saturated hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms include a benzyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, and a group represented by the following formula: Etc.

As R ¹ , a saturated hydrocarbon group in which a hydrogen atom is substituted with —COOR ⁸ and a saturated hydrocarbon group in which a hydrogen atom is substituted with —OCOR ⁸ are preferable, and Formula (f-1) to Formula (f— The group represented by 14) is more preferable. When R ¹ is the above group, the compound of the present invention tends to exhibit high solubility in an organic solvent. In formula (f-1) to formula (f-14), * represents a bonding position with a nitrogen atom on the pyridone ring.

R ² is a hydrogen atom, —CN or —CONH ₂ . Especially, -CN is preferable at the point which is easy to acquire a raw material.

R ³ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an N-butyl group, a sec-butyl group, and a tert-butyl group.
As a C1-C4 alkyl group substituted by the halogen atom, a trifluoromethyl group, a pentafluoroethyl group, etc. are mentioned, for example.
R ³ is preferably a methyl group or a trifluoromethyl group, and particularly preferably a methyl group.

R ^{4a to} R ^7a are, independently of each other, —R ⁸ , —OR ⁸ , —COOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, —SO ₃ Na, —SO ₃ K, —SO ₃ . it is preferably ₂ NR ⁸ R ⁹ or ^-NR 11 ^{R 12.} When R ^{4a to} R ^7a are these groups, it is easy to obtain raw materials.
R ^{4 to} R ⁷ are independently of each other —R ⁸ , —OR ⁸ , —COOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, —SO ₃ Na, —SO ₃ K, or —SO. ₂ NR ⁸ R ⁹ .

Examples of —NR ¹¹ R ¹² in R ^{4a to} R ^7a include N-methylamino group, N, N-dimethylamino group, N-ethylamino group, N, N-diethylamino group, N-propylamino group, N , N-dipropylamino group, N-butylamino group, N, N-dibutylamino group, N-pentylamino group, N-acetylamino group and the like.
Examples of —NR ¹¹ R ¹² in which R ¹¹ and R ¹² are bonded to each other to form a ring containing a nitrogen atom include a 1-pyrazolyl group, a pyrrolidino group, a piperidino group, and a morpholino group.
Among these, an N-acetylamino group is preferable from the viewpoint of solubility in an organic solvent.

Examples of —SO ₂ NR ⁸ R ⁹ in R ^{4a to} R ^7a and R ^{4 to} R ⁷ include an unsubstituted sulfamoyl group, an N-1 substituted sulfamoyl group, and an N, N-2 substituted sulfamoyl group.

Examples of the N-1-substituted sulfamoyl group include N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, and N-butylsulfamoyl group. N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- ( 2-methylbutyl) sulfamoyl group, N- (3-methylbutyl) sulfamoyl group, N-cyclopentyl Rufamoyl group, N-hexylsulfamoyl group, N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N-heptylsulfamoyl group, N- (1- Methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5-dimethyl) hexylsulfamoyl group An N-1 substituted sulfamoyl group substituted with an aliphatic hydrocarbon group such as a group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group, N-allylsulfamoyl group;
N- (2-hydroxyethyl) sulfamoyl group, N- (3-hydroxypropyl) sulfamoyl group, N- (2-hydroxypropyl) sulfamoyl group, N- (2,3-dihydroxypropyl) sulfamoyl group, N- (2 -Hydroxybutyl) sulfamoyl group, N- (4-hydroxybutyl) sulfamoyl group, N-substituted sulfamoyl group substituted with an aliphatic hydrocarbon group having a hydroxy group such as N- (1-hydroxymethylethyl) sulfamoyl group ;
N- (2-methoxyethyl) sulfamoyl group, N- (2-ethoxyethyl) sulfamoyl group, N- (1-methoxypropyl) sulfamoyl group, N-methoxypropylsulfamoyl group, N-ethoxypropylsulfamoyl group N-propoxypropylsulfamoyl group, N-isopropoxypropylsulfamoyl group, N-hexyloxypropylsulfamoyl group, N- (2-ethylhexyloxypropyl) sulfamoyl group, N- (3-tert- Butoxypropyl) sulfamoyl group, N- (4,4-dimethoxybutyl) sulfamoyl group, N-substituted sulfamoyl group substituted with an alkyl group or cycloalkyl group having an alkoxy group such as N-methoxyhexylsulfamoyl group;
An N-1 substituted sulfamoyl group substituted with an aliphatic hydrocarbon group having an alkoxyalkyl group such as an N- [1- (2-ethoxyethoxy) propyl] sulfamoyl group;
An N-1-substituted sulfamoyl group substituted with an aryl group such as an N-phenylsulfamoyl group and an N- (1-naphthyl) sulfamoyl group;
N-benzylsulfamoyl group, N- (1-phenylethyl) sulfamoyl group, N- (2-phenylethyl) sulfamoyl group, N- (3-phenylpropyl) sulfamoyl group, N- (4-phenylbutyl) sulfamoyl Group, N- [2- (2-naphthyl) ethyl] sulfamoyl group, N- [2- (4-methylphenyl) ethyl] sulfamoyl group, N- (3-phenyl-1-propyl) sulfamoyl group, N- ( N-1-substituted sulfamoyl group substituted with an aralkyl group such as 3-phenyl-1-methylpropyl) sulfamoyl group;
N- (3,4,5-trimethoxybenzyl) sulfamoyl group, N- [2- (3,4-dimethoxyphenyl) ethyl] sulfamoyl group, N- [2- (2-ethoxyphenyl) ethyl] sulfamoyl group, etc. N-1 substituted sulfamoyl group substituted with an aralkyl group having the following substituents;

Examples of the N, N-2 substituted sulfamoyl group include N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, and N, N-propylmethyl. Sulfamoyl group, N, N-isopropylmethylsulfamoyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) ) N, N-substituted sulfamoyl group substituted by two aliphatic hydrocarbon groups such as sulfamoyl group, N, N-heptylmethylsulfamoyl group;
N, N-bis (2-hydroxyethyl) sulfamoyl group, N, N-bis (2-methoxyethyl) sulfamoyl group, aliphatic hydrocarbon having substitution such as N, N-bis (2-ethoxyethyl) sulfamoyl group And N, N-2 substituted sulfamoyl group substituted with a group.

The ^{R 8} and ^{R 9} in the -SO ₂ NR ⁸ R ^9, branched alkyl groups having 6 to 8 carbon atoms, an allyl group, a phenyl group, an aralkyl group having 8 to 10 carbon atoms, 2 to 8 carbon atoms A hydroxy group-containing alkyl group or aryl group, or an alkoxy group-containing alkyl group or aryl group having 2 to 8 carbon atoms is preferable, and a 2-ethylhexyl group is particularly preferable.

A ⁺ is hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms.
The tetraalkylammonium cation is a quaternary ammonium cation having four alkyl groups, and one alkyl group has 1 to 4 carbon atoms.
Examples of the tetraalkylammonium cation include a tetramethylammonium cation, a tetraethylammonium cation, a tetrabutylammonium cation, and a dimethyldibutylammonium cation, and a tetrabutylammonium cation is preferable.

Examples of compound (0) include compound (I-1) to compound (I-177). In Table 1, ⁿ Bu represents an n-butyl group. In Table 1, if the expression number R ¹ column is described, it referred to the formula numbers of the groups indicated above and below. In formula (f-15) to formula (f-18), * represents a bonding position with a nitrogen atom on the pyridone ring.

  Especially, since spectral density is high, a compound (I-1)-a compound (I-5), a compound (I-143), and a compound (I-156) are preferable.

As an example of a method for producing the compound of the present invention, a method for producing compound (I) will be described. Among compounds (0), a compound that is not compound (I) can also be produced by a method similar to the method for producing compound (I) shown below.
Compound (I) can be produced by forming a complex using a compound represented by formula (d) (hereinafter sometimes referred to as “compound (d)”) and a chromium compound.

[In formula (d), R ^{1 to} R ⁷ represent the same meaning as in formula (I). ]

As a method for producing the compound (d), it can be produced by diazo coupling a diazonium salt and a pyridone compound as described in JP-B-7-88633.
Specifically, the compound (d) can be produced by diazo coupling a diazonium salt represented by the formula (b) and a pyridone compound represented by the formula (c). The diazonium salt represented by the formula (b) can be obtained, for example, by diazotizing the amine represented by the formula (a) with nitrous acid, nitrite or nitrite.

[In formula (a), formula (b) and formula (c), R ^{1 to} R ⁷ represent the same meaning as in formula (I). A ¹ represents an inorganic anion or an organic anion. ]

Examples of the inorganic anion include fluoride ion, chloride ion, bromide ion, iodide ion, perchlorate ion, hypochlorite ion, and the like. Examples of the organic anion include CH ₃ —COO ⁻ and C ₆ H ₅ —COO ^— . Preferred are chloride ion, bromide ion and CH ₃ —COO ^— .

  Compound (d) can be produced by reacting the diazonium salt represented by formula (b) with the pyridone compound represented by formula (c) in an aqueous solvent. The reaction temperature is preferably -5 ° C to 60 ° C, more preferably 0 ° C to 30 ° C. The reaction time is preferably 1 hour to 12 hours, more preferably 1 hour to 4 hours. Examples of the aqueous solvent include N-methylpyrrolidone and the like.

  The method for obtaining the target compound (d) from the reaction mixture is not particularly limited, and various known techniques can be employed. For example, the reaction mixture is preferably mixed with an acid (for example, acetic acid and the like) and water, and the precipitated crystals are collected by filtration. The acid is preferably prepared by preparing an aqueous solution of the acid in advance, and then adding the reaction mixture to the aqueous solution. The temperature when adding the reaction mixture is 10 ° C. or higher and 50 ° C. or lower, preferably 20 ° C. or higher and 50 ° C. or lower, preferably 20 ° C. or higher and 30 ° C. or lower. Moreover, after adding a reaction mixture to the aqueous solution of acid, 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.

  In the compound (I), the compound (d) is reacted with the chromium compound in an aqueous solvent (for example, N, N-dimethylformamide, N-methylpyrrolidone, etc.), preferably at 70 to 150 ° C. for 3 to 10 hours. Can be manufactured.

Examples of the chromium compound include chromium formate, chromium acetate, chromium chloride, chromium fluoride, ammonium sulfate chromium, and preferably chromium formate, ammonium sulfate, and the like.
It is preferable that the usage-amount of a chromium compound is 0.5-1 mol with respect to 1 mol of compounds (d).

  In order to promote the reaction, an inorganic base can be present together.

  Examples of the inorganic base include sodium hydroxide, calcium hydroxide, sodium carbonate, calcium carbonate, sodium acetate, calcium acetate and the like, preferably sodium carbonate and sodium acetate.

  The method for obtaining the target compound (I) 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 compound of the present invention thus obtained is useful as a dye. In addition, since the compound of the present invention has a high spectral density, it is useful as a dye used in color filters, fiber materials, etc. of display devices such as liquid crystal display devices that display colors using reflected light or transmitted light.

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

In addition to the dye of the present invention, the colorant (A) 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 (A) is preferably 5 to 60% by mass with respect to the solid content in the colored resin composition. Here, solid content means the sum total of the component except a solvent in a colored resin composition.
The content of the dye of the present invention contained in the colorant (A) 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 (B) is not particularly limited, and any resin may be used. The resin (B) 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 (B) 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 (B) is preferably 5,000 to 35,000, and more preferably 6,000 to 30,000.
The acid value of the resin (B) is preferably 50 to 150, and more preferably 60 to 135.
Content of resin (B) becomes like this. Preferably it is 7-65 mass% with respect to solid content of a colored resin composition, More preferably, it is 13-60 mass%.

  The polymerizable compound (C) 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 (D). For example, the compound etc. which have a polymerizable carbon-carbon unsaturated bond are mentioned.

The polymerizable compound (C) 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 compounds (C) may be used alone or in combination of two or more.
It is preferable that content of a polymeric compound (C) is 5-65 mass% with respect to solid content of a colored resin composition, More preferably, it is 10-60 mass%.

As said polymerization initiator (D), 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 (D) may be used alone or in combination of two or more.

  The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). 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 (E) 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 (E) in a colored resin composition becomes like this. Preferably it is 70-95 mass% with respect to a colored resin composition, More preferably, it is 75-90 mass%.

  The colored resin composition of the present invention can be used in various ways such as surfactants, fillers, other polymer compounds, adhesion promoters, antioxidants, ultraviolet absorbers, light stabilizers, chain transfer agents, etc. An additive may be included.

The compounds of the present invention are useful as dyes. In addition, since the compound of the present invention has a high molar extinction coefficient and a high spectral density, it is particularly useful as a dye for use in a color filter of a display device such as a liquid crystal display device.
In addition, the colored resin composition containing the compound of the present invention includes various display devices such as a display device (for example, a known liquid crystal display device, an organic EL device) having a color filter as a part of its constituent parts, and a solid-state imaging device. It can be used in a known manner for equipment related to colored images.

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

  In the following Examples, the structure of the compound was confirmed by NMR (JMM-ECA-500; manufactured by JEOL Ltd.) and mass spectrometry (LC: Agilent 1200 type, MASS: Agilent LC / MSD type).

[Example 1]
After 90 parts of water was added to 13.0 parts of anthranilic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.1 parts of sodium hydroxide was added and dissolved. Under ice cooling, 19.5 parts of sodium nitrite was added, and then 58.53 parts of 35% hydrochloric acid was added little by little. Thereafter, the mixture was stirred for 2 hours under ice cooling, and 200 parts of a 9% amidosulfuric acid aqueous solution was slowly added to quench excess nitrous acid, followed by stirring for about 5 minutes to obtain a suspension containing a diazonium salt.

Subsequently, 21.4 parts of the compound represented by the formula (c-1) was suspended in 150 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. The suspension containing the diazonium salt was added dropwise by a pump over about 30 minutes while maintaining the pH of the suspension at 8.0 to 9.5. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours to obtain a yellow suspension. The yellow solid obtained after filtration was dried at 60 ° C. under reduced pressure to obtain 30.5 parts of a compound represented by the formula (d-1). ^The structure was confirmed by ¹ H-NMR.

Identification of compound represented by formula (d-1)
¹ H-NMR (500 MHz, δ value (ppm, TMS standard), DMSO-d ₆ ); 0.90 (3H, t), 1.29 (2H, sextet), 1.48 (2H, quintet), 2 .58 (3H, s), 3.84 (2H, t), 7.31 (1H, t), 7.57 (1H, td), 7.84 (1H, d), 8.05 (1H, dd), 16.4 (1H, s).

  After adding 225 parts of N-methylpyrrolidone to 4.5 parts of the compound represented by the formula (d-1) and heating to 80 ° C. to dissolve, chromium formate n hydrate (manufactured by Nacalai Tesque) 1 8 parts was added and stirred at 130 ° C. for about 7 hours to obtain a dark orange solution. This solution was poured into 500 parts of a 1N aqueous hydrochloric acid solution, and the resulting orange solid was filtered, washed twice with 50 parts of water, and then vacuum-dried at 60 ° C. to obtain the formula (I-1). 3.9 parts of the compound obtained (yield 78%).

Identification of compound represented by formula (I-1) (mass spectrometry) ionization mode = ESI−: m / z = 756.2 [M−H] ⁻
Exact Mass: 757.2

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[Example 2]
After adding 170 parts of water to 17.0 parts of anthranilic acid, 5.4 parts of sodium hydroxide was added and dissolved. Under ice cooling, 25.5 parts of sodium nitrite was added, and then 79.5 parts of 35% hydrochloric acid was added little by little. Thereafter, the mixture was stirred for 2 hours under ice cooling, and 250 parts of 9% amidosulfuric acid aqueous solution was slowly added to quench excess nitrous acid, followed by stirring for about 10 minutes to obtain a suspension containing a diazonium salt.

Next, 24.1 parts of the compound represented by the formula (c-2) was suspended in 170 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. The suspension containing the diazonium salt was added dropwise by a pump over about 30 minutes while maintaining the pH of the suspension at 8.0 to 9.5. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60 ° C. under reduced pressure to obtain 39.9 parts of a compound represented by the formula (d-2). ^The structure was confirmed by ¹ H-NMR.

Identification of compound represented by formula (d-2)
¹ H-NMR (500 MHz, δ value (ppm, TMS standard), DMSO-d ₆ ); 1.08 (3H, t), 2.58 (3H, s), 3.88 (2H, q), 7 .32 (1H, t), 7.58 (1H, td), 7.85 (1H, d), 8.05 (1H, dd), 16.4 (1H, s).

  After adding 200 parts of N-methylpyrrolidone to 10 parts of the compound represented by the formula (d-2) and heating to 80 ° C. to dissolve, 3.7 parts of chromium formate n hydrate was added at 135 ° C. The mixture was stirred for about 2 hours, then the temperature was lowered to 80 ° C., 1.2 parts of sodium carbonate was added, and the mixture was again stirred at 135 ° C. for about 2 hours to obtain a dark orange solution. This solution was poured into 1000 parts of a 1N aqueous hydrochloric acid solution, and the resulting orange solid was filtered, washed twice with 80 parts of water, and then vacuum-dried at 60 ° C. to obtain the formula (I-2). 7.5 parts (yield 68%) of the obtained compound were obtained.

Identification of compound represented by formula (I-2) (mass spectrometry) ionization mode = ESI−: m / z = 700.1 [M−Na] ⁻
Exact Mass: 723.1

Example 3
After adding 150 parts of water to 13.0 parts of 2-amino-1,4-benzenedicarboxylic acid, 5.1 parts of sodium hydroxide was added and dissolved. Under ice cooling, 14.8 parts of sodium nitrite was added, and then 59.4 parts of 35% hydrochloric acid was added little by little. Thereafter, the mixture was stirred for 3 hours under ice-cooling, and 150 parts of 9% amidosulfuric acid aqueous solution was slowly added to quench excess nitrous acid, followed by stirring for about 10 minutes to obtain a suspension containing a diazonium salt.

Next, 16.2 parts of the compound represented by the formula (c-1) was suspended in 120 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. Here, the suspension containing the diazonium salt was dropped by a pump over about 1 hour while maintaining the pH of the suspension at 8.5 to 10.5. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours to obtain a dark orange solution. When the pH was adjusted to 3 by adding 1N aqueous hydrochloric acid, a yellow suspension was obtained. The yellow solid obtained by filtration was dried at 60 ° C. under reduced pressure to obtain 24.9 parts of a compound represented by the formula (d-3). ^The structure was confirmed by ¹ H-NMR.

Identification of compound represented by formula (d-3)
¹ H-NMR (500 MHz, δ value (ppm, TMS standard), DMSO-d ₆ ); 0.91 (3H, t), 1.31 (2H, sextet), 1.50 (2H, quintet), 2 .47 (3H, s), 3.78 (2H, t), 7.74 (1H, d), 8.02 (1H, d), 8.30 (1H, s), 15.5 (1H, s).

  After adding 125 parts of water to 2.5 parts of the compound represented by the formula (d-3) and heating to 75 ° C. to dissolve, 1.2 parts of chromium formate n hydrate was added at about 100 ° C. Stir for 8 hours to give a dark orange solution. This solution was poured into 300 parts of a 1N aqueous hydrochloric acid solution, and the resulting orange solid was filtered, followed by vacuum drying at 60 ° C., whereby 1.7 parts of the compound represented by the formula (I-3) (yield) 65%).

Identification of compound represented by formula (I-3) (mass spectrometry) ionization mode = ESI−: m / z = 844.2 [M−H] ⁻
Exact Mass) 845.2

Example 4
After adding 70 parts of water to 10.0 parts of 2-amino-5-nitrobenzoic acid, 2.4 parts of sodium hydroxide was added to obtain a yellow suspension. Under ice cooling, 11.3 parts of sodium nitrite was added, and then 35.2 parts of 35% hydrochloric acid was added little by little. Thereafter, the mixture was stirred for 3.5 hours under ice cooling, and 120 parts of 9% amidosulfuric acid aqueous solution was slowly added to quench excess nitrous acid, followed by stirring for about 10 minutes to obtain a suspension containing a diazonium salt.

Next, 11.8 parts of the compound represented by the formula (c-3) was suspended in 85 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. Here, the suspension containing the diazonium salt was dropped by a pump over about 1 hour while maintaining the pH of the suspension at 7.5 to 9.5. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60 ° C. under reduced pressure to obtain 15.9 parts of a compound represented by the formula (d-4). ^The structure was confirmed by ¹ H-NMR.

Identification of compound represented by formula (d-4)
¹ H-NMR (500 MHz, δ value (ppm, TMS standard), DMSO-d ₆ ); 1.14 (3H, t), 2.24 (3H, s), 3.86 (2H, dd), 7 .69 (2H, dd), 8.06 (1H, d), 8.40 (1H, dd), 8.67 (1H, d), 15.3 (1H, s).

  After adding 150 parts of N-methylpyrrolidone to 5.0 parts of the compound represented by formula (d-4) and heating to 50 ° C. to dissolve it, 1.8 parts of chromium formate n hydrate is added to 120 ° C. After stirring for about 2 hours, 0.6 part of sodium carbonate was added and the mixture was further stirred for 3 hours to obtain a dark orange solution. This solution was poured into 20% brine, and the resulting orange solid was filtered, followed by vacuum drying at 60 ° C., whereby 2.9 parts of the compound represented by the formula (I-4) (yield: 53). %).

Identification of compound represented by formula (I-4) (mass spectrometry) ionization mode = ESI−: m / z = 826.1 [M−Na] ⁻
Exact Mass: 849.1

Example 5
After adding 88 parts of water to 5.5 parts of anthranilic acid, 3.2 parts of sodium hydroxide was added to obtain a yellow suspension. Under ice cooling, 8.9 parts of sodium nitrite was added, and then 33.2 parts of 35% hydrochloric acid was added little by little. Thereafter, the mixture was stirred for 3 hours under ice cooling. To quench excess nitrous acid, 100 parts of 9% aqueous amidosulfuric acid solution was slowly added and stirred for about 10 minutes to obtain a suspension containing a diazonium salt.

  On the other hand, 26.0 parts of acetoacetic acid ethyl ester (manufactured by Tokyo Chemical Industry Co., Ltd.), 20.8 parts of methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 24.4 parts of 2-aminoethanol (manufactured by Wako Pure Chemical Industries, Ltd.) The parts were mixed and stirred at 95 ° C. for 24 hours. The reaction solution was cooled to room temperature, added to a mixed solution of 304 parts of water and 35 parts of 35% hydrochloric acid, and stirred at room temperature for 1 hour. The precipitated crystals were obtained as a residue of suction filter and dried to obtain 20.4 parts of a compound represented by the formula (c-4).

Next, 8.5 parts of the compound represented by the formula (c-4) was suspended in 77 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. The suspension containing the diazonium salt was added dropwise by a pump over about 1 hour while maintaining the pH of the suspension at 8.0 to 9.5. After completion of dropping, the mixture was further stirred at room temperature for 2 hours to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60 ° C. under reduced pressure to obtain 11.2 parts of the compound represented by the formula (d-5). ^The structure was confirmed by ¹ H-NMR.

Identification of compound represented by formula (d-5)
¹ H-NMR (270 MHz, δ value (ppm, TMS standard), DMSO-d ₆ ); 2.56 (3H, s), 3.52 (2H, t), 3.93 (2H, t), 4 .82 (1H, brs), 7.36 (1H, t) 7.74 (1H, t), 8.02-8.06 (1H, 1H, overlapped), 15.7 (1H, s).

  To 10 parts of the compound represented by the formula (d-5), 150 parts of N, N-dimethylformamide, 7.7 parts of ammonium chromium sulfate and 2.6 parts of sodium acetate were added and stirred at 135 ° C. for about 6 hours. An orange solution was obtained. This solution was poured into 20% brine, and the resulting orange solid was filtered and then vacuum dried at 60 ° C. to give 8.0 parts of the compound represented by the formula (I-5) (yield: 73). %).

Identification of compound represented by formula (I-5) (mass spectrometry) ionization mode = ESI−: m / z = 732.1 [M−Na] ⁻
Exact Mass: 755.1

Example 6
After adding 80 parts of water to 19.4 parts of 5- (N-acetylamino) anthranilic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.4 parts of sodium hydroxide was added and dissolved. Under ice-cooling, 19.7 parts of 35% aqueous sodium nitrite solution was added, and then 26.2 parts of 35% hydrochloric acid was added little by little to dissolve and stirred for 2 hours to obtain a suspension containing a diazonium salt.

  Next, 20.4 parts of the compound represented by the formula (c-4) was suspended in 100 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. The suspension containing the diazonium salt was added dropwise thereto using a pump over 15 minutes. After completion of dropping, the mixture was further stirred for 30 minutes to obtain a yellow suspension. Stir for 1 hour. The yellow solid obtained by filtration was dried at 60 ° C. under reduced pressure to obtain 39.1 parts of a compound represented by the formula (d-6).

Next, to 39.9 parts of the compound represented by the formula (d-6), 32.5 parts of an acid chloride represented by the formula (e-1) (manufactured by Wako Pure Chemical Industries, Ltd.) is added. The mixture was stirred in methyl pyrrolidone at 70 ° C. for 3 hours. After completion of the reaction, the reaction mixture was charged in water to obtain 50.1 parts of a compound represented by the formula (d-7). The obtained compound was orange and the maximum absorption wavelength (λmax) was measured in an ethyl lactate solvent to show 459 nm. The structure was confirmed by ¹ H-NMR.
¹ H-NMR: 0.72 (3H, m), 0.75 (3H, m), 1.02 (2H, m), 1.07 (2H, m), 1.23 (2H, m), 1.31 (2H, m), 2.06 (3H , s), 2.11 (1H, m), 4.10 (2H, m), 4.24 (2H, m), 7.88 (1H, m), 7.92 (1H, m), 8.32 (1H, d), 10.26 (1H, s), 15.63 (1H, s).

  To 10.0 parts of the compound represented by the formula (d-7), 150 parts of N, N-dimethylformamide, 7.7 parts of ammonium chromium sulfate and 2.6 parts of sodium acetate were added and stirred at 135 ° C. for about 6 hours. A dark orange solution was obtained. This solution was poured into 20% brine, and the resulting orange solid was filtered and then vacuum dried at 60 ° C. to obtain 4.9 parts of a compound represented by the formula (I-143).

Identification of compound represented by formula (I-143) (mass spectrometry) ionization mode = ESI−: m / z = 1098.3 [M−Na] ⁻
Exact Mass: 1121.34

Example 7
Next, 32.4 parts of benzoyl chloride (manufactured by Wako Pure Chemical Industries, Ltd.) is added to 30.0 parts of the compound represented by the formula (d-6), and the mixture is kept at 70 ° C. for 3 hours in N-methylpyrrolidone. Stir. After completion of the reaction, the reaction mixture was charged in water to obtain 35.8 parts of a compound represented by the formula (d-8). The obtained compound was orange and the maximum absorption wavelength (λmax) was measured in an ethyl lactate solvent to show 459 nm. The structure was confirmed by ¹ H-NMR.
¹ H-NMR: 2.70 (3H, s), 2.50 (3H, s), 4.28 (2H, t), 4.44 (2H, t), 7.43 (1H, t), 7.57 (1H, m), 7.89 (1H m), 7.95 (1H, m), 8.35 (1H, m), 10.27 (1H, s), 15.67 (1H, s).

  Next, 150 parts of N, N-dimethylformamide, 7.7 parts of ammonium chromium sulfate, and 2.6 parts of sodium acetate are added to 9.6 parts of the compound represented by the formula (d-8), and the mixture is about 6 at 135 ° C. Stir for hours to give a dark orange solution. This solution was poured into 20% brine, and the resulting orange solid was filtered, followed by vacuum drying at 60 ° C. to obtain 7.1 parts of a compound represented by the formula (I-156).

Identification (mass spectrometry) ionization mode of the compound represented by formula (I-156) = ESI−: m / z = 1054.20 [M−Na] ⁻
Exact Mass: 1077.19

<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 absorbance at the maximum absorption wavelength (λmax) and the maximum absorption wavelength (λmax) of the solution was measured using an ultraviolet-visible spectrophotometer (V-650DS; manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm). It was measured. The results are shown in Table 2.

  In the table, compound (R-1) is C.I. I. Solvent Yellow 21 (Oleosol Fast Yellow 2G; manufactured by Taoka Chemical Industry Co., Ltd.).

Example 8
<Preparation of colored resin composition>
(A) Colorant: Compound (I-1): Compound synthesized in Example 1 20 parts (B-1) Resin: Methacrylic acid / benzyl methacrylate copolymer (molar ratio; 30/70; weight average molecular weight 10700, Acid value 70 mg KOH / g) 70 parts (C-1) polymerizable compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 30 parts (D-1) photopolymerization initiator: benzyl dimethyl ketal (Irgacure 651; BASF Japan) 15 parts (E-1) solvent: 680 parts of ethyl lactate are mixed to obtain a colored resin composition.

<Preparation of color filter>
On the glass, the colored resin composition obtained above is applied by a spin coating method 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.

Example 9
A colored resin composition and a color filter are obtained in the same manner as in Example 8, except that the compound (I-1) synthesized in Example 1 is replaced with the compound (I-2) synthesized in Example 2.

Example 10
A colored resin composition and a color filter are obtained in the same manner as in Example 8, except that the compound (I-1) synthesized in Example 1 is replaced with the compound (I-3) synthesized in Example 3.

Example 11
A colored resin composition and a color filter are obtained in the same manner as in Example 8, except that the compound (I-1) synthesized in Example 1 is replaced with the compound (I-4) synthesized in Example 4.

Example 12
A colored resin composition and a color filter are obtained in the same manner as in Example 8, except that the compound (I-1) synthesized in Example 1 is replaced with the compound (I-5) synthesized in Example 5.

Example 13
A colored resin composition and a color filter are obtained in the same manner as in Example 8, except that the compound (I-1) synthesized in Example 1 is replaced with the compound (I-143) synthesized in Example 6.

Example 14
A colored resin composition and a color filter are obtained in the same manner as in Example 8, except that the compound (I-1) synthesized in Example 1 is replaced with the compound (I-156) synthesized in Example 7.

  From the results in Table 2, it can be seen that the compound of the present invention has a high absorbance because of its high absorbance. In addition, the colored resin composition containing the compound has excellent color performance and can produce a high-quality color filter.

  The compounds of the present invention are useful as dyes. Since the compound of the present invention has a high molar extinction coefficient and a high spectral density, it is particularly useful as a dye for use in a color filter of a display device such as a liquid crystal display device.

Claims (7)

Compound represented by formula (0).

Wherein (0), R ¹ represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, hydrogen atoms contained in the saturated hydrocarbon ^{group, -OR 8, -COOR 8, -OCOR} 8 , -CONR ⁸ R ⁹ , a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and —O— among —CH ₂ — contained in the saturated hydrocarbon group Unbonded —CH ₂ — may be replaced by —CO—.
R ² represents a hydrogen atom, —CN, or —CONH ₂ .
R ³ represents an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
R ^{4a to} R ^7a are independently of each other, —R ⁸ , —OR ⁸ , —COOR ⁸ , —COR ⁸ , —OCOOR ⁸ , —OCOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, It represents a _{-SO 3 Na, -SO 3 K,} -SO 2 NR 8 R 9 or ^-NR 11 ^{R 12.} R ^4a and R ^5a , R ^5a and R ^6a , and R ^6a and R ^7a may be bonded to each other to form a 6- to 7-membered ring containing carbon of a benzene ring.
R ⁸ and R ⁹ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a monovalent aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon group, and a hydrogen atom contained in the aliphatic hydrocarbon group, the aralkyl group and the aromatic hydrocarbon group may be substituted with -OR ¹⁰ .
R ¹⁰ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
R ¹¹ and R ¹² each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an acyl group having 2 to 8 carbon atoms, or a tetrahydrofurfuryl group. R ¹¹ and R ¹² may be bonded to each other to form a ring containing a nitrogen atom.
A ⁺ represents a hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms. ] A compound represented by formula (I).

[In the formula (I), R ¹ represents a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group is —OR ⁸ , —COOR ⁸ , —OCOR ^8. , -CONR ⁸ R ⁹ , a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and —O— among —CH ₂ — contained in the saturated hydrocarbon group Unbonded —CH ₂ — may be replaced by —CO—.
R ² represents a hydrogen atom, —CN or —CONH ₂ .
R ³ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom.
R ^{4 to} R ⁷ are independently of each other —R ⁸ , —OR ⁸ , —COOR ⁸ , —CN, —NO ₂ , a halogen atom, —SO ₃ H, —SO ₃ Na, —SO ₃ K, or —SO. ₂ represents NR ⁸ R ⁹
R ⁸ and R ⁹ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a monovalent aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon group, and a hydrogen atom contained in the aliphatic hydrocarbon group, the aralkyl group and the aromatic hydrocarbon group may be substituted with -OR ¹⁰ .
R ¹⁰ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
A ⁺ represents a hydrone, a sodium cation, a potassium cation or a tetraalkylammonium cation having 1 to 4 carbon atoms. ] The compound according to claim 1, wherein R ¹ is a monovalent saturated hydrocarbon group having 1 to 8 carbon atoms which may be substituted with —OH or —OCOR ⁸ . The compound according to any one of claims 1 to 3, wherein at least three of R ^{4a to} R ^7a are hydrogen atoms, or at least three of R ^{4 to} R ⁷ are hydrogen atoms. R ² is A compound according to claim 1 is -CN.   The dye which uses the compound in any one of Claims 1-5 as an active ingredient.   The coloring resin composition containing the dye of Claim 6, resin, and a solvent.