JP2019123856A - Yellow compound, coloring composition containing the compound, colorant for color filters and color filter - Google Patents

Abstract

To provide a yellow compound excellent in solubility to an organic solvent (e.g. propylene glycol monomethyl ether (PGME)) and in heat resistance during film making, a coloring composition containing the compound, a colorant for color filters containing the coloring composition, and a color filter employing the colorant for color filters.SOLUTION: The present invention provides a compound represented by formula (1) (R-Rindependently represent H, OH or the like, Rand Rindependently represent H, an optionally substituted C1-25 linear or branched alkyl group or the like, n is an integer of 1-3, Z is a monovalent group).SELECTED DRAWING: None

Description

  The present invention relates to a yellowish compound, a coloring composition containing the compound, a coloring agent for color filters containing the coloring composition, and a color filter using the coloring composition.

  Many pigments have been developed so far, for example, quinophthalone pigments, azo pigments, diketopyrrolopyrrole pigments, etc. (see, for example, Patent Documents 1 to 4). These pigments are used, for example, for coloring when making a color filter used for a liquid crystal or an electroluminescent (EL) display device. The color filter is manufactured by laminating a colored layer on a light transmitting substrate such as glass by a dyeing method, a pigment dispersion method, a printing method, an electrodeposition method or the like. The above-mentioned quinophthalone-based pigment is a yellowish compound synthesized by condensation of quinaldine and phthalic anhydride, and is used as a coloring agent for color filters because of its sharpness (Patent Document 1, Non-patent Document 1). However, as the image quality of displays increases, the performance required for color filters increases, and it is necessary to further improve coloring strength, lightness and contrast.

  Since pigments are generally insoluble in solvents, they are present in the form of fine particles in color filters containing resins and the like. Therefore, a color filter using a pigment affects transparency and color purity by transmitting and reflecting light on the surface of the pigment particles in the filter, and has a depolarizing effect by reflection, so that color liquid crystal display It is known that the contrast ratio of the device is reduced.

  In order to solve the problem of the decrease in contrast ratio, a method using only a dye as a colorant or a method using a dye and a pigment in combination has been proposed. Since the dye is soluble in the solvent, the color filter using the dye is less depolarizing than the case where only the pigment is used as the colorant, has excellent spectral characteristics, and improves the contrast and brightness. It is expected.

Japanese Patent Publication No. 47-3476 JP 2012-193318 A JP 2012-12498 A JP 2001-220520 A

Ichimura Kunihiro Supervised, "Advanced Color Filter Process Technology and Chemicals", CMC Publishing Co., Ltd., 2006, p. 80

  The present invention has been made to solve the above problems, and improves the solubility of a yellowish compound in an organic solvent (such as propylene glycol monomethyl ether (PGME)), contains the compound, and has coloring power and sharpness. It is an object of the present invention to provide a coloring composition excellent in color characteristics such as color and hue, a coloring agent for color filter containing the coloring composition, and a color filter using the coloring agent.

  The present invention is obtained as a result of earnest studies to achieve the above object, and the following is a summary.

1. The compound represented by following General formula (1).

[Wherein, R ^{1 to} R ⁶ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, —SO ₃ H, —SO ₃ M,
A substituted or unsubstituted indanedione group having 9 to 25 carbon atoms, preferably 9 to 20 carbon atoms,
A sulfo group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent,
A linear or branched alkoxy group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
An acyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms, which may have a substituent,
The ring forming atoms having 5 to 25 atoms, preferably 5 to 20, which may have a substituent, or the ring forming atoms having 5 to 20, preferably 5 to 20, which may have a substituent. Represents an aryloxy group of
R ^{1 to} R ⁶ may be bonded to each other in adjacent groups to form a ring.
M represents an alkali metal atom.
And any n of R ^{1 to} R ⁶ are replaced by -NR ⁷ R ⁸ ,
R ⁷ and R ⁸ each independently represent a hydrogen atom,
A linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
The aromatic hydrocarbon group having 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms, which may have a substituent, or 5 to 25 ring forming atoms which may have a substituent, preferably 5 to 5 carbon atoms 20 heterocyclic groups,
R ⁷ and R ⁸ may be bonded to each other to form a ring.
n represents an integer of 1 to 3;
Z represents a monovalent group. ]

2. The compound whose Z is a monovalent group represented by following General formula (2) in said General formula (1).

[Wherein, R ^{9 to} R ¹² each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, —SO ₃ H, —SO ₃ M,
A substituted or unsubstituted indanedione group having 9 to 25 carbon atoms, preferably 9 to 20 carbon atoms,
A sulfo group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent,
A linear or branched alkoxy group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
An acyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms, which may have a substituent,
The ring forming atoms having 5 to 25 atoms, preferably 5 to 20, which may have a substituent, or the ring forming atoms having 5 to 20, preferably 5 to 20, which may have a substituent. Represents an aryloxy group of
R ^{9 to} R ¹² may be bonded to each other in adjacent groups to form a ring.
M represents an alkali metal atom. ]

3. The compound whose Z is a monovalent group represented by following General formula (3) in said General formula (1).

[Wherein, R ^{13 to} R ¹⁸ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, —SO ₃ H, —SO ₃ M,
A substituted or unsubstituted indanedione group having 9 to 25 carbon atoms, preferably 9 to 20 carbon atoms,
A sulfo group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent,
A linear or branched alkoxy group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, which may have a substituent,
An acyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms, which may have a substituent,
The ring forming atoms having 5 to 25 atoms, preferably 5 to 20, which may have a substituent, or the ring forming atoms having 5 to 20, preferably 5 to 20, which may have a substituent. The aryloxy groups R ^{9 to} R ¹² may be bonded to each other between adjacent groups to form a ring.
M represents an alkali metal atom. ]

4. In the above general formula (1), compounds wherein n is 1 or 2 and R ² , R ⁴ or R ⁶ is —NR ⁷ R ⁸ .

5. In the above general formula (1), compounds wherein R ⁷ and R ⁸ each represent a linear or branched alkyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent.

6. A compound wherein the solubility of the compound in propylene glycol monomethyl ether (PGME) at 25 ° C. ± 2 ° C. is 0.1% by weight or more.

7. The compound whose maximum absorption wavelength of the range of 350-700 nm in the solution of said compound is in the range of 370-430 nm.

8. A colored composition containing the compound.

9. The coloring agent for color filters containing the said coloring composition.

10. A color filter using the colorant for color filter.

  The compound according to the present invention is excellent in the solubility in organic solvents such as PGME as compared with the conventional yellowish compound, and is excellent in the heat resistance at the time of film formation, so the compound according to the present invention The coloring composition containing is useful as a coloring agent for color filters.

  Hereinafter, embodiments of the present invention will be described in detail. In addition, this invention is not limited to the following embodiment, It can variously deform and implement within the range of the summary. First, the compound represented by the general formula (1) will be described.

In the general formula (1), the part represented by the following general formula (1-a) can be represented as "(-NR ⁷ R ⁸ ) _n ". Further, in the general formula (1), “—NR ⁷ R ⁸ ” represents that any one position of R ^{1 to} R ⁶ may be bound, and the number of “—NR ⁷ R ⁸ ” Is n, and n is an integer of 1 to 3. When n is 2 or more, a plurality of R ⁷ and R ⁸ may be the same or different.

As the “halogen atom” represented by R ^{1 to} R ^{6 in} the general formula (1), R ^{9 to} R ¹² in the general formula (2), or R ^{13 to} R ¹⁸ in the general formula (3) , Chlorine atom, bromine atom, iodine atom and the like. As the "halogen atom", a fluorine atom or a chlorine atom is preferable.

In the general formula ^(1), R 1 ~R ⁶ represented by "substituted carbon atoms, which may atoms 9 to 25, preferably indanedione group having 9 to 20""number of carbon atoms 9 to the “25, preferably 9 to 20 indanedione groups” mean groups having the same structure as the group represented by the general formula (2). Provided that “substituent” in “the optionally substituted indanedione group having 9 to 25 carbon atoms, preferably 9 to 20” represented by R ^{1 to} R ⁶ in the general formula (1) And the groups represented by R ^{9 to} R ¹² in the general formula (2) may be identical to or different from one another. In addition, when a "substituent" contains a carbon atom, the carbon atom is not included in said "C9-C25, Preferably 9-20".

“1 to 25 carbon atoms” in “the optionally substituted sulfo group having 1 to 25 carbon atoms, preferably 1 to 20 sulfo groups” represented by R ^{1 to} R ⁶ in the general formula (1) Preferably, a sulfo group of 1 to 20 means a group represented as "-SO ₃ -R", and R is a group having 1 to 25 carbon atoms which may have a substituent, preferably 1 to The “substituent” in the “20 sulfo group” means

In the general formula (1), “a linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms which may have a substituent,” represented by R ^{1 to} R ⁶ Specific examples of the “linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms” in the above include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, Linear alkyl groups such as heptyl group, octyl group, nonyl group and decyl group; branched alkyl groups such as isopropyl group, isobutyl group, s-butyl group, t-butyl group, isooctyl group and 2-ethylhexyl group Can be mentioned.

In the general formula (1), “C 5 carbon atoms in the“ C 5 -C 25 optionally substituted cycloalkyl group, preferably 5 20 cycloalkyl group ”represented by R ^{1 to} R ⁶ Specifically, examples of the "cycloalkyl group of 25 to 25 and preferably 5 to 20" include cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl. Be

In the general formula (1), “a linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms which may have a substituent,” represented by R ^{1 to} R ⁶ Specific examples of “a linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms” in the following include vinyl, 1-propenyl, allyl, 1-butenyl, 2- Examples thereof include alkenyl groups such as butenyl group, 1-pentenyl group, 1-hexenyl group, isopropenyl group and isobutenyl group, and linear or branched alkenyl groups in which a plurality of these alkenyl groups are bonded.

In the general formula (1), “a linear or branched alkoxy group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms which may have a substituent,” preferably represented by R ^{1 to} R ⁶ Specific examples of the “linear or branched alkoxy group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms” in the above include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy A linear alkoxy group such as heptyloxy group, octyloxy group, nonyloxy group, decyloxy group; branched such as isopropoxy group, isobutoxy group, s-butoxy group, t-butoxy group, isooctyloxy group, etc. An alkoxy group is mentioned.

In the general formula (1), “C 5 carbon atoms in the“ optionally substituted carbon atoms having 5 to 25 carbon atoms, preferably 5 to 20 cycloalkoxy groups ”represented by R ^{1 to} R ⁶ Specifically, examples of the "cycloalkoxy group" of 25 to 25 and preferably 5 to 20 include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl; 1-adamantyl; 2-adamantyl group and the like.

In the general formula (1), “C ¹ to C ⁶ carbon atoms in the optionally substituted acyl groups having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms” represented by R ^{1 to} R ⁶ Specific examples of the 25, preferably 1 to 20 acyl group "include acyl groups having 1 to 19 carbon atoms such as formyl, acetyl, propionyl, acrylyl and benzoyl.

In the general formula ^(1), represented by R 1 to R ^6, "carbon atoms which may have a substituent having 6 to 25, preferably an aromatic hydrocarbon group having 6 to 20" number "carbon in 6 Specifically, examples of the “aromatic hydrocarbon group” of 25 to 25 and preferably 6 to 20 include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group (anthryl group), a phenanthryl group, a fluorenyl group, an indenyl group, Aromatic hydrocarbon groups such as pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group (in the present invention, "aromatic hydrocarbon group" also includes aryl group or fused polycyclic aromatic group).

In the general formula (1), a “ring-forming atom” in the “optionally substituted ring-forming atom having 5 to 25, preferably 5 to 20, heterocyclic group” represented by R ^{1 to} R ⁶ Specific examples of the heterocyclic group having a number of 5 to 25, preferably 5 to 20 include a pyridyl group, a pyrimidinyl group, a triazinyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a thienyl group and a furyl group (furanyl group), Pyrrolyl group, quinolyl group, isoquinolyl group, naphthyridinyl group, indolyl group, acridinyl group, phenanthrolinyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group Group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl Group, a Hajime Tamaki such as carbolinyl group (or a heteroaromatic hydrocarbon group).

In the general formula (1), a “ring-forming atom” in the “optionally substituted ring-forming atom having 5 to 25, preferably 5 to 20, aryloxy group” represented by R ^{1 to} R ⁶ Specific examples of the aryloxy group having a number of 5 to 25, preferably 5 to 20 include aryl such as phenyloxy group, biphenylyloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, etc. An oxy group is mentioned.

In the general formula (1), “a linear or branched alkyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms having a substituent,” represented by R ^{1 to} R ⁶ , or “a substituent carbon atoms from 2 to 25 having, preferably as the "substituent" in a linear or branched alkenyl group "having 2 to 20, specifically, a deuterium atom, a hydroxyl group, -SO 3 ^_-, a cyano group, A nitro group; a halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; a cycloalkyl group having 3 to 19 carbon atoms; a linear or branched alkoxy group having 1 to 19 carbon atoms; 3-19 cycloalkoxy group or 1-adamantyloxy group, 2-adamantyloxy group; C6-C19 aromatic hydrocarbon group or condensed polycyclic aromatic group; C2-C19 heterocycle ; Mono- or di-substituted amino group of 1 to 19 carbon atoms; unsubstituted amino group; an aryloxy group having a carbon number of 6 to 19 acyl group 1 to 19 carbon atoms, and the like. In addition, when a "substituent" contains a carbon atom, the carbon atom has the above "9 to 25 carbon atoms, preferably 9 to 20 carbon atoms,""1 to 25 carbon atoms, preferably 1 to 20 carbon atoms," It is not included in 5 to 25 carbon atoms, preferably 5 to 20 carbon atoms, 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, and 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms. One or more of these "substituents" may be contained, or two or more of them may be contained. Moreover, these "substituents" may further have the substituents exemplified above. In addition, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

In the general formula (1), "a carbon number of 9 to 25 carbon atoms, preferably 9 to 20 carbon atoms having a substituent," represented by R ^{1 to} R ^6; 25, preferably 5 to 20 cycloalkyl groups, "a substituted or unsubstituted linear or branched alkoxy group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms", or "the number of carbon atoms having a substituent group 5 to 25, preferably 5 to 20 cycloalkoxy groups, "an acyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms having a substituent,""6 to 25 carbon atoms having a substituent, preferably Is an aromatic hydrocarbon group of 6 to 20, "a heterocyclic group having 5 to 25, preferably 5 to 20 ring-forming atoms having a substituent,""5 to 25 ring-forming atoms having a substituent, preferably Is an aryloxy group of 5 to 20 "or Carbon atoms 0 to 25 which has a substituent, examples of "substituent" in preferably 0 to 20 amino groups ", specifically, a deuterium atom, a hydroxyl group, -SO ₃ ^-, a cyano group, a nitro group, fluorine A halogen atom such as an atom, a chlorine atom, a bromine atom or an iodine atom; a linear or branched alkyl group having 1 to 19 carbon atoms; a cycloalkyl group having 3 to 19 carbon atoms; A linear or branched alkenyl group; a linear or branched alkoxy group having 1 to 19 carbon atoms; a cycloalkoxy group having 3 to 19 carbon atoms, a 1-adamantyloxy group, a 2-adamantyloxy group; An acyl group having 1 to 19 carbon atoms; an aromatic hydrocarbon group having 6 to 19 carbon atoms or a fused polycyclic aromatic group; a heterocyclic group having 2 to 19 carbon atoms; an aryl having 6 to 19 carbon atoms Aryloxy group; an unsubstituted amino group; mono- or di-substituted amino group of 1 to 19 carbon atoms; and the like. In addition, when a "substituent" contains a carbon atom, the carbon atom has the above-mentioned "C9 to C25, preferably 9 to 20", "C5 to 25, preferably 5 to 20", " The carbon number is not included in 1 to 25, preferably 1 to 20, "6 to 25 carbon atoms, preferably 6 to 20", and "0 to 25 carbon atoms, preferably 0 to 20". One or more of these "substituents" may be contained, or two or more of them may be contained. Moreover, these "substituents" may further have the substituents exemplified above. In addition, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

In the above-mentioned various “groups” having “substituents” represented by R ^{1 to} R ⁶ in the general formula (1), mention is made as “substituents”,
"C1-C19 linear or branched alkyl group",
"C3-C19 cycloalkyl group",
“A linear or branched alkenyl group having 2 to 19 carbon atoms”,
"C1-C19 linear or branched alkoxy group",
"C3-C19 cycloalkoxy group",
"Acyl group having 1 to 19 carbon atoms",
"C6-C19 aromatic hydrocarbon group or fused polycyclic aromatic group",
"Heterocyclic group having 2 to 19 carbon atoms",
"C6-C19 aryloxy group",
As the "monosubstituted or disubstituted amino group having 1 to 19 carbon atoms" or the "acyl group having 1 to 19 carbon atoms", specifically,
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, n-hexyl group, 2-ethylhexyl group, A linear or branched alkyl group having 1 to 19 carbon atoms, such as heptyl group, octyl group, isooctyl group, nonyl group, decyl group;
A cycloalkyl group having 3 to 19 carbon atoms, such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, cyclononyl group and cyclodecyl group;
Vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 1-pentenyl group, 1-hexenyl group, isopropenyl group, isobutenyl group, or the number of carbon atoms to which these alkenyl groups are bonded 2 to 19 linear or branched alkenyl groups;
Methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, isopropoxy, isobutoxy, s-butoxy and t-butoxy groups , A linear or branched alkoxy group having 1 to 19 carbon atoms such as isooctyloxy group;
Cycloalkoxy groups having 3 to 19 carbon atoms such as cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cyclononyloxy, cyclodecyloxy and the like;
An acyl group having 1 to 19 carbon atoms such as formyl group, acetyl group, propionyl group, acrylyl group, benzoyl group;
Phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl (anthryl), phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, etc. Aromatic hydrocarbon group or fused polycyclic aromatic group;
Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group (furanyl group), pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, quinolyl group, isoquinolyl group, naphthyridinyl group, acridinyl group, phenanthrolinyl group, benzofuranyl group Groups such as benzothienyl group, oxazolyl group, indolyl group, carbazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group, etc. A heterocyclic group having 2 to 19 atoms;
An aryloxy group having 6 to 19 carbon atoms such as phenyloxy group, tolyloxy group, biphenylyloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group;
Straight or branched alkyl having 1 to 19 carbon atoms, such as methylamino, dimethylamino, diethylamino, ethylmethylamino, methylpropylamino, di-t-butylamino, diphenylamino and the like And a mono- or di-substituted amino group having an aromatic hydrocarbon group having 6 to 19 carbon atoms, and the like.

In the general formula (1), R ^{1 to} R ⁶ may be bonded to each other via adjacent groups, a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring Good.

In the general formula (1), as R ^{1 to} R ⁶ ,
Hydrogen atom, hydroxyl group, halogen atom, nitro group,
Indanedione group having 9 to 20 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
Or -NR ⁷ R ⁸ is preferable, and a hydrogen atom or -NR ⁷ R ⁸ is more preferable.

In the general formula (1), n represents an integer of 1 to 3, preferably 1 or 2. Further, in the general formula (1), it is preferable that R ² , R ⁴ or R ⁶ is —NR ⁷ R ⁸ .

In general formula (1), represented by R ⁷ or R ⁸ ,
“C1-C25, preferably 1-20 linear or branched alkyl group optionally having substituent (s),”
“C 5-25, preferably 5-20 cycloalkyl group optionally having substituent (s),”
“A linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent,”
“C 5-25, preferably 5-20, cycloalkoxy group optionally having substituent (s),”
“Aromatic hydrocarbon group having 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms which may have a substituent,” or “5 to 25 ring forming atoms which may have a substituent, is preferable As various “groups” of “5 to 20 heterocyclic groups”,
The same ones as the “group” similarly represented by R ^{1 to} R ⁶ in the general formula (1) can be mentioned. Also,
Also for the “substituents” that these “groups” represented by R ⁷ or R ⁸ may have, the same ones as the “substituents” in R ^{1 to} R ⁶ can be mentioned.

As R ⁷ and R ⁸ in the general formula (1), a hydrogen atom,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
The C6-C20 aromatic hydrocarbon group which may have a substituent is preferable.

  In the general formula (1), Z represents a monovalent group and is preferably a monovalent group represented by the general formula (2) or (3).

In the general formula (1), “—NR ⁷ R ⁸ ” represents that any position of R ^{1 to} R ⁶ may be bonded, but in the general formula (1), Z in the general formula is When it is a monovalent group represented by (2) or (3), “—NR ⁷ R ⁸ ” may be at any position among R ^{1 to} R ⁶ , R ^{9 to} R ¹² or R ^{13 to} R ¹⁸ Even in this case, the number of “—NR ⁷ R ⁸ ” is n, and n represents an integer of 1 to 3. When n is 2 or more, a plurality of R ⁷ and R ⁸ may be the same or different.

“Indanedione group having 9 to 20 carbon atoms which may have a substituent, represented by R ^{9 to} R ¹² in the general formula (2) or R ^{13 to} R ¹⁸ in the general formula (3) ",
“Sulfo group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms which may have a substituent,”
“C1-C25, preferably 1-20 linear or branched alkyl group optionally having substituent (s),”
“C 5-25, preferably 5-20 cycloalkyl group optionally having substituent (s),”
“A linear or branched alkenyl group having 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms, which may have a substituent,”
“C1-C25, preferably 1-20 linear or branched alkoxy group optionally having substituent (s),”
“C 5-25, preferably 5-20, cycloalkoxy group optionally having substituent (s),”
“An acyl group having 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms which may have a substituent,”
“Aromatic hydrocarbon group having 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms which may have a substituent,”
“A heterocyclic group having 5 to 25, preferably 5 to 20 ring atoms, which may have a substituent,” or “5 to 25 ring atoms, which may have a substituent, preferably Examples of various “groups” in the 5 to 20 aryloxy group ”include the same ones as the“ groups ”similarly represented by R ^{1 to} R ⁶ in the general formula (1). Moreover, as for the "substituent" that may be possessed by these "groups" in the general formula (2) or (3), the same ones as the "substituent" in the general formula (1) can be exemplified.

In the general formulas (2) and (3), R ^{9 to} R ¹² and R ^{13 to} R ¹⁸ are each adjacent to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. It may combine to form a ring.

In the general formulas (2) and (3), R ^{9 to} R ¹² and R ^{13 to} R ¹⁸ are a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group,
Indanedione group having 9 to 20 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
Or -NR ⁷ R ⁸ is preferred.

  In the general formulas (1), (2) or (3), "M" represents an alkali metal atom, preferably a lithium atom, a sodium atom or a potassium atom, more preferably a lithium atom or a sodium atom, particularly preferably a sodium atom preferable.

  In the present invention, preferred examples of the compound represented by the general formula (1) are shown below, but the invention is not limited to these compounds. In the following structural formula, some hydrogen atoms are omitted. In addition, even when a stereoisomer exists, its plane structural formula is described.

The compounds of the present invention represented by the general formula (1) can be synthesized by known methods (for example, Patent Document 1). In the following, a synthesis example in the case of an indandione group in which n = 1, R ² = —NR ⁷ R ⁸ and Z in the general formula (1) is represented by the general formula (2) is shown.
By using a cross coupling reaction of a 4-chloro-2-methylquinoline derivative having the corresponding substituent and an amine such as H-NR ⁷ R ⁸ having the corresponding substituent according to a suitable solvent and temperature, A 2-methylquinoline derivative having —NR ⁷ R ⁸ as a substituent is obtained.
Furthermore, by subjecting the obtained 2-methylquinoline derivative and a phthalic anhydride having the corresponding substituent to a dehydration condensation reaction according to a suitable solvent and temperature, the compound of the present invention represented by the general formula (1) Compounds can be obtained.

  As a method of purifying the product during the synthesis of the compound of the present invention, purification by column chromatography; adsorption purification by silica gel, activated carbon, activated clay or the like; known methods such as recrystallization or crystallization with a solvent Be In addition, as necessary, identification and analysis of these compounds include nuclear magnetic resonance analysis (NMR), absorbance measurement with a spectrophotometer, ultraviolet-visible absorption spectrum (UV-Vis) measurement, thermogravimetry-differential thermal analysis ( TG-DTA) etc. can be performed. Moreover, these methods can be used also for the solubility of the obtained compound, color evaluation, and heat resistance evaluation.

  The solubility of the compound in the present invention is expressed by solubility, and the solubility represents the ratio of the maximum amount that the substance can dissolve in a particular solvent, and, for example, "weight% (solvent name, temperature)" etc. It is expressed in units of. Solubility can be obtained, for example, by mixing a sample in a specific solvent, stirring the solvent at a constant temperature for a fixed time, and measuring the concentration of the prepared saturated solution, liquid chromatography (LC) or absorbance of the dissolved part It can also be obtained by measuring the concentration by measurement.

  By performing thermogravimetry-differential thermal analysis (TG-DTA) of the compound of the present invention, the thermal decomposition temperature can be analyzed, and can be used as an indicator of heat resistance. In the coloring composition, the thermal decomposition temperature of the compound of the dye portion is preferably 250 ° C. or more. When applied to a color filter, the higher the thermal decomposition temperature, the better.

A coating film can be produced by mixing the compound of the present invention with various resin solutions and coating the solution on a glass substrate. The obtained coating film can be subjected to color measurement using a spectrocolorimeter to obtain a color value of the coating film, whereby color evaluation can be performed. As the color value, a CIE L ^* a ^* b ^* color system or the like is generally used. Specifically, the color values L ^* , a ^* and b ^* of the film sample are measured, and the heat resistance can be judged from the color difference (ΔE ^* _ab ) of the color values before and after heating at an appropriate temperature. When applied to a color filter, the color difference at a temperature of around 230 ° C. can be used as an indicator of heat resistance. The smaller the value of ΔE ^* _ab , the smaller the color change due to thermal decomposition, and therefore, it is preferably 3 or less.

  Since the coloring composition contained in the coloring agent for color filter needs to be well dissolved or dispersed in the resin and the organic solvent, the compound contained in these coloring compositions is to the organic solvent It is preferred that the solubility is high. Specific examples of the organic solvent include esters such as ethyl acetate and n-butyl acetate; ethers such as diethyl ether and propylene glycol monomethyl ether (PGME); ether esters such as propylene glycol monomethyl ether acetate (PGMEA); Ketones such as acetone and cyclohexanone; alcohols such as methanol and ethanol; diacetone alcohol (DAA) and the like; aromatic hydrocarbons such as benzene, toluene and xylene; N, N-dimethylformamide (DMF), N-methyl Amides such as pyrrolidone (NMP); dimethyl sulfoxide (DMSO) and the like. These solvents may be used alone or in combination of two or more. Among these, the compound according to the present invention is excellent in solubility in PGME and PGMEA, for example, solubility (% by weight) in PGME at 25 ± 2 ° C. (solvent PGME, 25 ± 2 ° C.) is 0.1 wt. % Or more is preferable, 1% by weight or more is more preferable, and 2% by weight or more is particularly preferable. In other words, at any temperature between 23 ° C. and 27 ° C., the solubility (% by weight) of the compound according to the present invention in PGME (solvent PGME, 25 ± 2 ° C.) is 0.1% by weight or more Is preferably 1% by weight or more, and particularly preferably 2% by weight or more.

  The compound represented by the general formula (1) preferably has a visible light region in a solution, for example, a maximum absorption wavelength in the range of 350 to 700 nm, in the range of 370 to 430 nm.

  The coloring composition of the present invention contains the compound of the present invention represented by the general formula (1), and may contain a compound of one type of structure, and two or more types of structures are compounds May be contained. In the present invention, the structure of the compound is preferably of one type.

  The coloring composition of the present invention can be used as a surfactant, a dispersing agent, an antifoaming agent, a leveling agent and other coloring agent for color filter as another component of the compound in order to enhance its performance as a coloring agent for color filter. Additives mixed at the time of production, organic compounds such as organic compounds can be added. However, the content of these additives in the coloring composition is preferably an appropriate amount, and the solubility of the coloring composition of the present invention in the solvent may be reduced or it may be improved more than necessary. It is preferable that it is a content rate of the range which does not affect the effect of the other same kind of additive used at the time of manufacture. These additives can be introduced at any time of preparation of the coloring composition.

  The coloring agent for color filters of the present invention comprises a coloring composition containing a compound represented by the general formula (1) and components generally used for the production of color filters. For example, in the case of a method using a photolithography process, a general color filter is a liquid prepared by mixing a dye such as a dye or a pigment with a resin component (including a monomer, an oligomer, a binder component, and a resist component) or a solvent. Is coated on a substrate such as glass or resin and photopolymerized using a photomask to prepare a colored pattern of a dye / resin composite film soluble / insoluble in a solvent, washed, and then heated. Be Since the compound of the present invention is excellent in solubility, it is excellent in dispersibility with the materials used for the production of these color filters, and therefore, it is mixed with other materials as necessary to form a film, heat resistance and light absorption The characteristics can be evaluated. Moreover, also in the electrodeposition method and the printing method, a coloring pattern can be produced using what mixed the pigment | dye with resin and other components. Accordingly, specific components in the colorant for color filters of the present invention include compounds represented by the general formula (1), dyes such as other dyes and pigments, resin components, organic solvents, photopolymerization initiators, etc. Other additives may be mentioned. Also, it is possible to select from these components or add other components as needed.

  When using the coloring composition of this invention as a coloring agent for color filters, it can be used as a yellowish color filter, but it can also be mixed and used for the color filter for other colors, such as red and green. In addition, the coloring composition of the present invention may be used alone, or known dyes such as other dyes or pigments may be mixed to adjust the color tone. For example, basic dyes; acid dyes; disperse dyes; spiro dyes; azo dyes, disazo dyes, quinoline dyes, stilbene dyes, (poly) methine dyes, cyanine dyes, indigo dyes, phthalocyanine dyes, anthraquinone dyes, acridine dyes, triaryls Methane type, indanthrene type, oxazine type, dioxazine type, naphthol AS type, benzimidazolone type, pyrazolone type, perylene type, perinone type, quinacridone type, isoindolinone type, xanthene type, diketopyrrolopyrrole type, etc. Dyes or pigments of

  The mixing ratio of the other pigment in the coloring composition of the present invention and the coloring agent for color filter is preferably 5 to 2000% by weight, and 10 to 1000% by weight based on the compound represented by the general formula (1). Is more preferred. The mixing ratio of dye components such as dyes in the liquid color filter colorant is preferably 0.5 to 70% by weight, and more preferably 1 to 50% by weight, based on the total colorant.

  As resin components in the coloring composition and the coloring agent for color filter of the present invention, known ones may be used if they have the required production method of the color filter resin film formed using them and the properties required at the time of use. It can be used. For example, acrylic resin, olefin resin, styrene resin, polyimide resin, urethane resin, polyester resin, epoxy resin, vinyl ether resin, phenol (novolak) resin, other transparent resin, photocurable resin, thermosetting resin, binder resin, A photoresist resin is mentioned, and these can be used in combination as appropriate. Moreover, the copolymer of these resin can also be used combining. In the case of a liquid colorant, the content of the resin in these colorants for color filters is preferably 5 to 95% by weight, and more preferably 10 to 50% by weight.

  Examples of other additives in the coloring composition of the present invention and the coloring agent for color filter include components necessary for polymerization and curing of the resin such as a photopolymerization initiator and a crosslinking agent, and further, coloring for liquid color filter Surfactants and dispersants necessary for stabilizing the properties of the components in the agent can be mentioned. Any of these may be used known ones for producing a color filter, and is not particularly limited. 5 to 60 weight% is preferable and, as for the mixing ratio of the total amount of these additives in the whole solid content of the coloring agent for color filters, 10 to 40 weight% is more preferable.

Hereinafter, the embodiments of the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples. In addition, the identification of the compound obtained in the synthesis example was performed by < ¹ > H-NMR analysis (Nihon Denshi Co., Ltd. nuclear magnetic resonance apparatus, JNM-ECA-600).

Synthesis Example 1 Synthesis of Compound (A-1) In a reaction vessel, 3.0 g of 4-chloro-2-methylquinoline, 4.4 g of dibutylamine, and 0.96 g of p-toluenesulfonic acid monohydrate are charged. The mixture was stirred at 130 ° C. for 5 hours. Toluene and water were added to the reaction solution, and the mixture was extracted with toluene. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane) to obtain 4-dibutylamino-2-methylquinoline (3.1 g, yield 68%).
Subsequently, 3.1 g of 4-dibutylamino-2-methylquinoline obtained above, 2.6 g of phthalic anhydride, 2.1 g of benzoic acid and 16 mL of 1,2,4-trichlorobenzene are put into a reaction vessel, Stir at 170 ° C. for 6 hours. After cooling to 25 ° C., purification by column chromatography (carrier: silica gel, solvent: dichloromethane) was performed to obtain a yellow powder (3.1 g, yield 68%).

  The NMR measurement of the obtained yellow powder was performed, the following 27 hydrogen signals were detected, and the structure of the compound represented by the following formula (A-1) was identified.

¹ H-NMR (600 MHz, CDCl ₃ ): δ (ppm) = 8.07 (1 H), 7.86 (1 H), 7.60-7.66 (3 H), 7.50-7.55 (3 H) ), 7.34 (1 H), 3.50 (4 H), 1.70 (4 H), 1.35 (4 H), 0.95 (6 H).

Synthesis Example 2 Synthesis of Compound (A-8) In a reaction vessel, 3.0 g of 4-dibutylamino-2-methylquinoline obtained by the same method as in Synthesis Example 1 above, 1,8-naphthalic acid 3.3 g of anhydride, 2.1 g of benzoic acid and 15 mL of 1,2,4-trichlorobenzene were added and stirred at 170 ° C. for 8 hours. After cooling to 25 ° C., the residue was purified by column chromatography (carrier: silica gel, solvent: dichloromethane) to obtain a yellow powder (2.2 g, yield 50%).

  The NMR measurement of the obtained yellow powder was performed, the following 29 hydrogen signals were detected, and the structure of the compound represented by the following formula (A-8) was identified.

¹ H-NMR (600 MHz, CDCl ₃ ): δ (ppm) = 9.31 (1 H), 8.67 (2 H), 8.10 (2 H), 7.98 (1 H), 7.80 (1 H) , 7.65-7.78 (3 H), 7.43 (1 H), 3.60 (4 H), 1.80 (4 H), 1.39 (4 H), 0.95 (6 H).

Synthesis Example 3 Synthesis of Compound (A-16) In a reaction vessel, 13.4 g of 4-dibutylamino-2-methylquinoline obtained by the same method as in Synthesis Example 1 above, trimellitic anhydride 9 The mixture was charged with .0 g, 6.0 g of benzoic acid and 67 mL of 1,2,4-trichlorobenzene, and stirred at 200 ° C. for 48 hours. After cooling to 25 ° C., toluene and ethanol were added and filtered to obtain a yellow powder (A-16) (14.6 g, yield 66%).

  The NMR measurement of the obtained yellow pigment was performed, and the following 27 hydrogen signals were detected, and the structure of the compound represented by the following formula (A-16) was identified.

¹ H-NMR (600 MHz, DMSO-d ₆ ): δ (ppm) = 13.20 (1 H), 8.15 (1 H), 8.00-7.84 (4 H), 7.75 (1 H), 7.62 (1 H), 7.47 (1 H), 3.54 (4 H), 1.72 (4 H), 1.35 (4 H), 0.92 (6 H).

Example 1
For the compound (A-1) obtained in Synthesis Example 1, the solubility (weight%) (solvent PGME, 25 ± 2 ° C.) in a PGME solvent at room temperature was measured. In addition, solubility was evaluated in the following four steps based on the value of the measured solubility. The results are shown in Table 1.
"◎": Solubility 2% by weight or more "○": 1 to 2% by weight
"△": 0.1 to 1% by weight
"X": less than 0.1 wt%

5.0 g of a 2 wt% DMF solution of a copolymer of methacrylic acid and an acrylic ester and 20 mg of the compound (A-1) obtained in Synthesis Example 1 were placed in a sample bottle and mixed with stirring for 30 minutes. The obtained colored resin solution was applied onto a glass substrate, and was heated at 100 ° C. for 2 minutes to form a film. The color value of the obtained film was measured using a spectrocolorimeter (CM-5, manufactured by Konica Minolta Co., Ltd.). Then, it heated at 230 degreeC for 20 minutes, and measured the color value similarly. The color difference (ΔE ^* _ab ) of the color value before and after heating at 230 ° C. is used as an index of heat resistance, and the results of evaluation in the following three stages are shown together in Table 1.
"○": ΔE ^* _ab <3.0
“△”: ΔE ^* _ab = 3.0 to 10.0
“×”: ΔE ^* _ab > 10.0

[Example 2 and Example 3]
The same method as in Example 1 except that the compounds (A-8) and (A-16) obtained in Synthesis Example 2 and Synthesis Example 3 were used instead of (A-1) as a compound. The solubility (% by weight) in PGME solvent at room temperature (solvent PGME, 25 ± 2 ° C) was measured at room temperature, and the color difference (ΔE ^* _ab ) of the color value before and after heating at 230 ° C was measured for the formed film. And evaluated. The results are summarized in Table 1 below.

Comparative Example 1
As a compound, instead of (A-1), C.I. which is a conventional dye compound represented by the following formula (B-1) not belonging to the present invention. I. The solubility (% by weight) (solvent PGME, 25 ± 2 ° C.) in PGME solvent at room temperature was measured in the same manner as in Example 1 except that solvent yellow 33 was used, and the film formed at 230 ° C. The color difference (ΔE ^* _ab ) of the color values before and after heating was measured and evaluated. The results are summarized in Table 1 below.

  As shown in Table 1, the compounds of the examples of the present invention show high solubility in PGME and high heat resistance at the time of film formation, and a coloring composition containing the compound of the present invention is a colored filter for color filters There is no problem in practical use as an agent. In addition, the solubility of the compound of Example 1 in PGME is twice or more the solubility of the compound of Comparative Example 1, and has higher heat resistance than that of Comparative Example 1 at the time of film formation. It turned out that it is useful as a filter coloring agent.

  The coloring composition containing the compound (yellowish compound) according to the present invention is excellent in solubility in an organic solvent (such as PGME) and is excellent in heat resistance at the time of film formation. It is useful as a coloring agent.

Claims (10)

The compound represented by following General formula (1).

[Wherein, R ^{1 to} R ⁶ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, —SO ₃ H, —SO ₃ M,
An optionally substituted indanedione group having 9 to 25 carbon atoms,
A sulfo group having 1 to 25 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms which may have a substituent,
An acyl group having 1 to 25 carbon atoms which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent,
A heterocyclic group having 5 to 25 ring atoms which may have a substituent, or an aryloxy group having 5 to 25 ring atoms which may have a substituent,
R ^{1 to} R ⁶ may be bonded to each other in adjacent groups to form a ring.
M represents an alkali metal atom.
And any n of R ^{1 to} R ⁶ are replaced by -NR ⁷ R ⁸ ,
R ⁷ and R ⁸ each independently represent a hydrogen atom,
A linear or branched alkyl group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent, or a heterocyclic group having 5 to 25 ring atoms which may have a substituent,
R ⁷ and R ⁸ may be bonded to each other to form a ring.
n represents an integer of 1 to 3;
Z represents a monovalent group. ] The compound according to claim 1, wherein Z in the general formula (1) is a monovalent group represented by the following general formula (2).

[Wherein, R ^{9 to} R ¹² each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, —SO ₃ H, —SO ₃ M,
An optionally substituted indanedione group having 9 to 25 carbon atoms,
A sulfo group having 1 to 25 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms which may have a substituent,
An acyl group having 1 to 25 carbon atoms which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent,
A heterocyclic group having 5 to 25 ring atoms which may have a substituent, or an aryloxy group having 5 to 25 ring atoms which may have a substituent,
R ^{9 to} R ¹² may be bonded to each other in adjacent groups to form a ring.
M represents an alkali metal atom. ] The compound according to claim 1, wherein Z in the general formula (1) is a monovalent group represented by the following general formula (3).

[Wherein, R ^{13 to} R ¹⁸ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, —SO ₃ H, —SO ₃ M,
An optionally substituted indanedione group having 9 to 25 carbon atoms,
A sulfo group having 1 to 25 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkyl group having 5 to 25 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 25 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 25 carbon atoms which may have a substituent,
A cycloalkoxy group having 5 to 25 carbon atoms which may have a substituent,
An acyl group having 1 to 25 carbon atoms which may have a substituent,
An aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent,
A heterocyclic group having 5 to 25 ring atoms which may have a substituent, or an aryloxy group having 5 to 25 ring atoms which may have a substituent,
R ^{9 to} R ¹² may be bonded to each other in adjacent groups to form a ring.
M represents an alkali metal atom. ] The compound according to any one of claims 1 to 3, wherein in the general formula (1), n is 1 or 2, and R ² , R ⁴ or R ⁶ is -NR ⁷ R ⁸ . 5. The method according to claim 1, wherein in the general formula (1), R ⁷ and R ⁸ each represent a linear or branched alkyl group having 2 to 25 carbon atoms which may have a substituent. The compound according to any one of the preceding claims.   The compound according to any one of claims 1 to 5, wherein the solubility of the compound in propylene glycol monomethyl ether (PGME) at 25 ° C ± 2 ° C is 0.1% by weight or more.   The compound according to any one of claims 1 to 6, wherein the maximum absorption wavelength in the range of 350 to 700 nm in the solution of the compound is in the range of 370 to 430 nm.   The coloring composition containing the compound as described in any one of Claims 1-7.   The coloring agent for color filters containing the coloring composition of Claim 8.   The color filter using the coloring agent for color filters of Claim 9.