Anthraquinone compound, coloring composition, and cured product

Abstract

To provide a novel anthraquinone compound that exhibits excellent thermal resistance and can be used in a color filter or a solder resist with suppressed absorption in the ultraviolet region.SOLUTION: An anthraquinone compound represented by formula (1), which is exemplified by, for example, Compound 1.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a novel anthraquinone compound, a colored composition containing the anthraquinone compound, and a cured product of the colored composition. [Background technology]

[0002] Color filters are optical filters primarily used in liquid crystal displays (LCDs) and organic light-emitting diodes (OLEDs). Color filters generally use the three primary colors of RGB, but it is difficult to achieve a pure RGB hue using a single color material, and efforts have been made to blend multiple color materials to approximate the desired RGB hue. Similarly, attempts have been made to blend multiple color materials to achieve the desired hue in solder resist for printed wiring boards.

[0003] Known colorants used in color filters and solder resists include Pigment Blue 15, a copper phthalocyanine pigment. A colored photosensitive resin composition that uses copper phthalocyanine to form a highly bright color filter has also been proposed (Patent Document 1).

[0004] In addition, anthraquinone dyes such as Solvent Blue 11 are also known, and photosensitive resins that use specific anthraquinone compounds and have excellent sensitivity, storage stability after lamination to a substrate, and color stability have also been proposed (Patent Document 2). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 2019-152852 [Patent Document 2] Japanese Patent Application Laid-Open No. 2013-57902 Summary of the Invention [Problem to be solved by the invention]

[0006] Copper phthalocyanine pigments have good heat resistance, but have the problem of high absorption of light in the ultraviolet region (especially at a wavelength of 365 nm), while anthraquinone dyes have the problem of poor heat resistance. Under these circumstances, there is a demand for a novel compound that can function as a colorant. An object of the present invention is to provide a novel compound, a colored composition containing the compound, and a cured product of the colored composition. [Means for solving the problem]

[0007] As a result of extensive investigations, the present inventors have discovered that an anthraquinone compound having a specific structure provides excellent heat resistance and suppresses absorption of light in the ultraviolet region (particularly at a wavelength of 365 nm), thereby completing the present invention.

[0008] The gist of the present invention is as follows. [1] An anthraquinone compound represented by the following formula (1): [ka] In formula (1), X1 and X2 each independently represent -O-, -NH-, or -S-; Y1 is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R s -R t -R s wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y1 is a single bond; Y2 is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R s -R t -R s wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y2 is a single bond; where R seach independently represents an alkyl group having 1 to 6 carbon atoms, a phenyl group, or an aralkyl group, and the alkyl group having 1 to 6 carbon atoms, the phenyl group, and the aralkyl group are optionally substituted; R t is a group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-, R1 and R2 each independently represent a hydrogen atom, -OH, or -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4), and a group represented by formula (5), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted; R3 each independently represents -OH, -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M aand a monovalent hydrocarbon group having 1 to 30 carbon atoms, which may be substituted; p is an integer from 1 to 9, q is an integer from 1 to 9, r is an integer from 0 to 4, R a represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R b represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R c represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R d represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; M a is sodium or potassium, however, Formula (1) has at least one group selected from the group represented by formula (2), the group represented by formula (3), the group represented by formula (4), and the group represented by formula (5). [ka] In formulas (2) to (5), R5 and R6 each independently represent -OH, -OX a , -SX a , -NX b X c , -NX b -C(=O)X d , -C(=O)NX b X c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OX d , -OC(=O)X d , -COOM b , -SO3H, -S(=O)2OXd , -OS(=O)2X d , -SO3M b and a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted; R7 is independently a hydrogen atom, -C(=O)Xe, -C(=O)OXe, or -C(=O)OM b , an alkyl group, an aralkyl group, or a monovalent aromatic cyclic group, the alkyl group, the aralkyl group, and the monovalent aromatic cyclic group may be substituted, and two R7 may be bonded to each other to form a ring; L is a linking group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-; s is an integer from 0 to 3, t is an integer from 0 to 4, u is an integer from 0 to 3, v is an integer from 0 to 2, X a represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X b represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X c represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X d represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; Xe is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X frepresents a single bond, an alkylene group, an alkenylene group, an alkynylene group, an aralkylene group or a divalent aromatic ring group, and these groups may be substituted; M b is sodium or potassium. [2] The anthraquinone compound of [1], wherein the formula (1) has at least two groups selected from the group represented by the formula (2), the group represented by the formula (3), the group represented by the formula (4), and the group represented by the formula (5). [3] The anthraquinone compound of [2], wherein the formula (1) has at least one R1 selected from the group represented by the formula (2), the group represented by the formula (3), the group represented by the formula (4), and the group represented by the formula (5), and has at least one R2 selected from the group represented by the formula (2), the group represented by the formula (3), the group represented by the formula (4), and the group represented by the formula (5). [4] A coloring composition containing the anthraquinone compound according to any one of [1] to [3]. [5] The coloring composition according to [4], further comprising a coloring material other than the anthraquinone compound according to [1]. [6] The coloring composition according to [4], which is a photosensitive coloring composition. [7] The coloring composition according to [5], which is a photosensitive coloring composition. [8] A cured product of the coloring composition according to any one of [4] to [7]. [Effects of the Invention]

[0009] According to the present invention, a novel anthraquinone compound, a coloring composition containing the anthraquinone compound, and a cured product of the coloring composition are provided. The anthraquinone compound of the present invention has excellent heat resistance and suppresses light absorption in the ultraviolet region (particularly, a wavelength of 365 nm). Due to these properties, the coloring composition of the present invention can be suitably used as a curable composition, and is particularly suitable for use as a photosensitive coloring composition. [Brief explanation of the drawings]

[0010] [Figure 1] 1 is an FT-IR chart of Compound 1 of an example. [Figure 2]1 is an FT-IR chart of Compound 2 of an example. [Figure 3] 1 is an FT-IR chart of Compound 3 of an example. [Figure 4] 1 is a chart of the absorbance of dry films of compounds 1, 2, 4 and 5 of the examples. [Figure 5] 1 is a chart showing ultraviolet-visible absorption spectra of solutions of compounds 1, 2, and 4 of the examples. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be described in detail below.

[0012] <Terminology> In this specification, the alkyl group may be branched or linear, and examples thereof include alkyl groups having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, an n-pentyl group, an n-hexyl group, a cyclohexyl group, and a 2-ethylhexyl group. The alkenyl group may be branched or linear, and examples thereof include alkenyl groups having 2 to 20 carbon atoms, preferably 2 to 8 carbon atoms. Specific examples thereof include vinyl groups, 1-propenyl groups, 2-propenyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, butadienyl groups, pentenyl groups, pentadienyl groups, and hexadienyl groups. The alkynyl group may be branched or linear, and examples thereof include alkynyl groups having 2 to 20 carbon atoms, preferably 2 to 8 carbon atoms. Specific examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a butidienyl group, a pentynyl group, a pentidienyl group, and a 1-hexynyl group. The aralkyl group is a group in which one hydrogen atom of an alkyl group is substituted with an aryl group, and examples thereof include aralkyl groups having 7 to 30 carbon atoms. Specific examples include a benzyl group, a methylbenzyl group, a 1-phenylethyl group, and a naphthylmethyl group. An alkylene group, an alkenylene group, and an alkynylene group are divalent groups formed by removing one hydrogen atom from an alkyl group, an alkenyl group, or an alkynyl group. An aralkylene group is a divalent group formed by removing one hydrogen atom from the aromatic ring of an aralkyl group. The hydrocarbon group is not particularly limited as long as it is a group having one or more carbon atoms, and includes alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, cycloalkenyl groups, cycloalkynyl groups, aryl groups, aralkyl groups, and the like. When the above groups are substituted, examples of the substituent include a hydroxyl group, an alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted amide group, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyano group, a nitro group, a carboxyl group (which may be in the form of a salt), a carboxylic acid ester residue, a sulfonic acid group (which may be in the form of a salt), a sulfonic acid ester residue, a hydrocarbon group, etc. The hydrocarbon group as a substituent may be substituted with any substituent, and may be interrupted by a heteroatom (an oxygen atom, a nitrogen atom, a sulfur atom, etc.) or a bond (an ester bond, an amide bond, etc.). The ring includes a carbocycle and a heterocycle. The carbocycle is not particularly limited as long as all of the ring-constituting atoms are carbon atoms, and examples thereof include 4- to 20-membered rings, preferably 4- to 14-membered rings. The carbocycle may be aromatic or non-aromatic, and may be monocyclic or polycyclic. Examples thereof include cycloalkanes (e.g., cyclopropane, cyclopentane, cyclohexane, etc.) and arenes (e.g., benzene, naphthalene, etc.). The carbocycle may contain the above-mentioned substituents and hydrocarbon groups. The heterocycle is not particularly limited as long as the ring-constituting atoms are carbon atoms and hetero atoms, and examples thereof include 4- to 20-membered rings, preferably 4- to 14-membered rings. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms. The heterocycle may be aromatic or non-aromatic, and may be monocyclic or polycyclic. Examples thereof include a pyridine ring, lactone ring, imidazole ring, thiazole ring, and oxazole ring. The heterocycle may contain the above-mentioned substituents and hydrocarbon groups. The aromatic ring may be a carbocyclic or heterocyclic ring, and includes the examples of aromatic rings listed above.

[0013] <Anthraquinone Substituent> The anthraquinone compound of the present invention is characterized by having at least one substituent having an anthraquinone structure (hereinafter also referred to as an anthraquinone substituent).

[0014] The anthraquinone substituents are represented by formulas (2) to (5). [ka] In formulas (2) to (5), R5 and R6 each independently represent -OH, -OX a , -SX a , -NX b X c , -NX b -C(=O)X d , -C(=O)NX b X c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OX d , -OC(=O)X d , -COOM b , -SO3H, -S(=O)2OX d , -OS(=O)2X d , -SO3M b and a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted; R7 is independently a hydrogen atom, -C(=O)Xe, -C(=O)OXe, or -C(=O)OM b , an alkyl group, an aralkyl group, or a monovalent aromatic cyclic group, the alkyl group, the aralkyl group, and the monovalent aromatic cyclic group may be substituted, and two R7 may be bonded to each other to form a ring; L is a linking group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-; s is an integer from 0 to 3, t is an integer from 0 to 4, u is an integer from 0 to 3, v is an integer from 0 to 2, X a represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X b represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X c represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X d represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; Xe is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X f represents a single bond, an alkylene group, an alkenylene group, an alkynylene group, an aralkylene group or a divalent aromatic ring group, and these groups may be substituted; M b is sodium or potassium.

[0015] In formula (2), L is preferably bonded to the α-position (5th and 8th positions) of the anthraquinone structure. In formula (3), L is preferably bonded to the β-position (2nd and 3rd positions) of the anthraquinone structure, where the position to which -N(R7)2 is bonded in the anthraquinone structure is defined as the 1st position.

[0016] In formula (2), L is preferably —O—. In the formula (3), L is preferably —O— or —S—. In formula (4), L is preferably a single bond. In formula (5), L is preferably a single bond.

[0017] In formula (2), s is preferably 0 or 1, and u is preferably 0 or 1. In formula (3), t is preferably 0 or 1, and v is preferably 0 or 1. In formula (4), t is preferably 0 or 1, and u is preferably 0 or 1. In formula (5), t is preferably 0 or 1, and v is preferably 0 or 1.

[0018] In formulas (2) to (5), when R5 and / or R6 are present, they each independently represent -NX b X c , -OH, -OX a or -SX a It is preferable that:

[0019] R7 in formulas (2) to (4) is preferably independently a hydrogen atom, an alkyl group, or a monovalent aromatic ring group, and more preferably a hydrogen atom or an alkyl group.

[0020] Examples of the anthraquinone substituent of formula (2) include groups represented by the following formulae (2-1) to (2-4), of which formulae (2-1) and (2-4) are preferred. [ka] In formulas (2-1) to (2-4), L is a linking group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-; Z1 to Z4 and Z5 to Z7 each independently represent a hydrogen atom, -OH, or -OX. a , -SX a , -NX b X c , -NX b -C(=O)X d , -C(=O)NX b X c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OX d , -OC(=O)X d , -COOM b , -SO3H, -S(=O)2OX d , -OS(=O)2X d , -SO3M b and a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, R7 is independently a hydrogen atom, -C(=O)Xe, -C(=O)OXe, or -C(=O)OM b , an alkyl group, an aralkyl group, or a monovalent aromatic cyclic group, and the alkyl group, aralkyl group, and monovalent aromatic cyclic group may be substituted.

[0021] L is preferably —O—. Z1 to Z4 each independently represent a hydrogen atom, -NX b X c , -OH or -OX a is preferred. Z5 to Z7 each independently represent a hydrogen atom, -NX b X c , -OH or -OX a is preferred. Each R7 is preferably independently a hydrogen atom, an alkyl group, or a monovalent aromatic ring group.

[0022] Examples of the anthraquinone substituent of formula (3) include the following formulae (3-1) to (3-3), of which formulae (3-2) and (3-3) are preferred. [ka] In formulas (3-1) to (3-3), L is a linking group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-; Z1 to Z4 and Z5 to Z7 each independently represent a hydrogen atom, -OH, or -OX. a , -SX a , -NX b X c , -NX b -C(=O)X d , -C(=O)NX b X c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OX d , -OC(=O)X d , -COOM b , -SO3H, -S(=O)2OX d , -OS(=O)2X d , -SO3M b and a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted; R7 is independently a hydrogen atom, -C(=O)Xe, -C(=O)OXe, or -C(=O)OM b , an alkyl group, an aralkyl group, or a monovalent aromatic cyclic group, and the alkyl group, aralkyl group, and monovalent aromatic cyclic group may be substituted.

[0023] L is preferably —O— or —S—. Z1 to Z4 each independently represent a hydrogen atom, -NX b X c , -OH or -OX a is preferred. Z5 to Z7 each independently represent a hydrogen atom, -NX b X c , -OH or -OX a is preferred. Each R7 is preferably independently a hydrogen atom, an alkyl group, or a monovalent aromatic ring group.

[0024] The anthraquinone substituent in formula (4) can be rewritten as formula (4-1). [ka] In formula (4-1), L is a linking group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-; Z1 to Z4 and Z5 to Z7 each independently represent a hydrogen atom, -OH, or -OX. a , -SX a , -NX b X c , -NX b -C(=O)X d , -C(=O)NX b X c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OX d , -OC(=O)X d , -COOM b , -SO3H, -S(=O)2OX d , -OS(=O)2X d , -SO3M b and a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, R7 is independently a hydrogen atom, -C(=O)Xe, -C(=O)OXe, or -C(=O)OMb , an alkyl group, an aralkyl group, or a monovalent aromatic cyclic group, and the alkyl group, aralkyl group, and monovalent aromatic cyclic group may be substituted.

[0025] L is preferably a single bond. Z1 to Z4 each independently represent a hydrogen atom, -NX b X c , -OH, or -OX a is preferred. Z5 to Z7 each independently represent a hydrogen atom, -NX b X c , -OH, -OX a , or -SX a is preferred. R7 is preferably a hydrogen atom or an alkyl group.

[0026] The anthraquinone substituent in formula (5) can be rewritten as formula (5-1). [ka] In formula (5-1), L is a linking group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-; Z1 to Z4, Z5 and Z8 each independently represent a hydrogen atom, -OH, -OX a , -SX a , -NX b X c , -NX b -C(=O)X d , -C(=O)NX b X c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OX d , -OC(=O)X d , -COOM b , -SO3H, -S(=O)2OX d , -OS(=O)2X d , -SO3M band monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon groups having 1 to 30 carbon atoms may be substituted.

[0027] L is preferably a single bond. Z1 to Z4 each independently represent a hydrogen atom, -NX b X c , -OH, or -OX a is preferred. Z5 and Z8 each independently represent a hydrogen atom, -NX b X c , -OH, -OX a , or -SX a is preferred.

[0028] <Anthraquinone compounds> The anthraquinone compound of the present invention is represented by formula (1), and has at least one anthraquinone substituent represented by any one of formulas (2) to (5) as R1 and R2. [ka] In formula (1), X1 and X2 each independently represent -O-, -NH-, or -S-; Y1 is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R s -R t -R s wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y1 is a single bond; Y2 is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R s -R t -R s wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y2 is a single bond; where R seach independently represents an alkyl group having 1 to 6 carbon atoms, a phenyl group, or an aralkyl group, and the alkyl group having 1 to 6 carbon atoms, the phenyl group, and the aralkyl group are optionally substituted; R t is a group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NH-C(=O)- and -C(=O)NH-, R1 and R2 each independently represent a hydrogen atom, -OH, or -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4), and a group represented by formula (5), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted; R3 each independently represents -OH, -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M aand a monovalent hydrocarbon group having 1 to 30 carbon atoms, which may be substituted; p is an integer from 1 to 9, q is an integer from 1 to 9, r is an integer from 0 to 4, R a represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R b represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R c represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R d represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; M a is sodium or potassium, however, Formula (1) has at least one group selected from the group represented by formula (2), the group represented by formula (3), the group represented by formula (4), and the group represented by formula (5).

[0029] As shown in formula (1), the anthraquinone compound of the present invention has a rigid structure, such as an aromatic amide structure, an aromatic ester structure, or an aromatic thioester structure, and is therefore presumed to have excellent heat resistance while maintaining the excellent performance of anthraquinone compounds as colorants.

[0030] Formula (1) preferably has at least two anthraquinone substituents represented by any of formulas (2) to (5), more preferably has at least one anthraquinone substituent R1 and at least one anthraquinone substituent R2, and particularly preferably has one anthraquinone substituent R1 and one anthraquinone substituent R2.

[0031] R1 and R2 other than the anthraquinone substituent are preferably hydrogen atoms.

[0032] In the anthraquinone compound of the present invention, X1 and X2 are preferably -O- or -NH-, and it is more preferable that both X1 and X2 are -O- or both X1 and X2 are -NH-.

[0033] In the anthraquinone compound of the present invention, Y1 is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R s -R t -R s wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group may each be substituted, or Y1 is a single bond. Y2 is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R s -R t -R s wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y2 is a single bond. Here, p is an integer from 1 to 9, and q is an integer from 1 to 9.

[0034] When p or q is 1, Y1 and Y2 are alkylene groups having 1 to 6 carbon atoms, phenylene groups (1,4-phenylene groups, 1,3-phenylene groups, etc.), or divalent residues derived from Rs-Rt-Rs; when p or q is 2 to 9, they are alkyl groups having 1 to 6 carbon atoms, phenyl groups, or R s -R t -R sIt is a trivalent to decavalent residue in which 2 to 9 hydrogen atoms have been removed from

[0035] In Rs-Rt-Rs, at least one of Rs is preferably a phenyl group, and Rt is preferably -C(=O)O-, -OC(=O)-, -C(=O)NH-, or -NHC(=O). In particular, it is preferred that both Rs are phenyl groups, and Rt is -C(=O)O-, -OC(=O)-, -C(=O)NH-, or -NHC(=O).

[0036] Y1 and Y2 can be single bonds. When Y1 is a single bond, it is preferable that p is 1 and R1 is a hydrogen atom. When X1 is -O-, the terminal is a carboxyl group. When Y2 is a single bond, it is preferable that q is 1 and R2 is a hydrogen atom. When X2 is -O-, the terminal is a carboxyl group.

[0037] Formula (1) has at least one anthraquinone substituent represented by any one of formulas (2) to (5).

[0038] r is preferably 0 or 1, and more preferably 0.

[0039] The compound of formula (1) includes compounds represented by formulas (1-1α), (1-1β), and (1-1γ). Formula (1-1α) is a compound in which X1 and X2 are -O- and Y1 and Y2 are phenylene groups, formula (1-1β) is a compound in which X1 and X2 are -NH- and Y1 and Y2 are phenylene groups, and formula (1-1γ) is a compound in which one of X1 and X2 is -O- and the other is -NH- and Y1 and Y2 are phenylene groups.

[0040] [ka] In formulas (1-1α), (1-1β) and (1-1γ), Z 10 ~Z 19 are each independently a hydrogen atom, -OH, or -OR a , -SXa , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a , a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4) or a group represented by formula (5), and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, with the proviso that Z 10 ~Z 19 At least one of the groups is a group represented by any one of formulas (2) to (5).

[0041] Z 10 ~Z 19 With regard to the group other than the group represented by any one of formulas (2) to (5), a hydrogen atom, an alkyl group or a halogen atom is preferred, and a hydrogen atom is more preferred.

[0042] Z 10 ~Z 19 It is preferred that one or two of these be a group represented by any one of formulas (2) to (5). Z 10 ~Z 19 When two of the groups are represented by any of the formulas (2) to (5), Z 10 ~Z 14 is a group represented by any one of formulas (2) to (5), and Z 15 ~Z 19 may be a group represented by any one of formulas (2) to (5), and preferably, Z 10 ~Z 19 Among them, Z 12 and Z 17 Either one or both of Z 11 and Z 16 Either one or both of these, or Z13 and Z 18 Either one or both of the following is a group represented by any one of formulas (2) to (5): A group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a The monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, and is preferably a hydrogen atom, an alkyl group, or a halogen atom, more preferably a hydrogen atom.

[0043] The compound of formula (1) includes compounds represented by formulas (1-2α), (1-2β), and (1-2γ). Formula (1-2α) is a compound in which X1 and X2 are -O- and Y1 and Y2 are Rs-Rt-Rs, formula (1-2β) is a compound in which X1 and X2 are -NH- and Y1 and Y2 are Rs-Rt-Rs, and formula (1-2γ) is a compound in which one of X1 and X2 is -O- and the other is -NH- and Y1 and Y2 are Rs-Rt-R.

[0044] [ka] In formulas (1-2α), (1-2β) and (1-2γ), Z 10 ~Z 19 , Z 20 ~Z 21 , Z 23 ~Z 26 and Z 28 ~Z 29are each independently a hydrogen atom, -OH, or -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a , a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4) or a group represented by formula (5), and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, with the proviso that Z 10 ~Z 29 At least one of the groups is a group represented by any one of formulas (2) to (5). Z t are each independently a group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -S(=O)2NH-, -NHS(=O)2-, -NH-C(=O)-, and -C(=O)NH-.

[0045] Z 10 ~Z 19 , Z 20 ~Z 21 , Z 23 ~Z 26 , Z 28 ~Z 29 With regard to the group other than the group represented by any one of formulas (2) to (5), a hydrogen atom, an alkyl group or a halogen atom is preferred, and a hydrogen atom is more preferred.

[0046] Z 10 ~Z 19 , Z 20 ~Z 21 , Z 23 ~Z 26 , Z 28 ~Z 29It is preferred that one or two of the groups are groups represented by any one of formulas (2) to (5), and Z 10 ~Z 19 It is preferred that one or two of these be a group represented by any one of formulas (2) to (5).

[0047] Z 10 ~Z 19 , Z 20 ~Z 21 , Z 23 ~Z 26 , Z 28 ~Z 29 When one or two of the groups are any of (2) to (5), Z 10 ~Z 14 is a group represented by any one of formulas (2) to (5), and Z 15 ~Z 19 may be a group represented by any one of formulas (2) to (5), and preferably, Z 10 ~Z 19 Among them, Z 12 and Z 17 Either one or both of Z 11 and Z 16 Either one or both of these, or Z 13 and Z 18 Either one or both of the following is a group represented by any one of formulas (2) to (5): A group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M aThe monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, and is preferably a hydrogen atom, an alkyl group, or a halogen atom, more preferably a hydrogen atom.

[0048] The compound of formula (1) includes compounds represented by formulas (1-3α), (1-3β), (1-3γ), and (1-3δ). Formula (1-3α) is a compound in which X1 and X2 are -O-, one of Y1 and Y2 is a phenylene group, and the other is Rs-Rt-Rs. Formula (1-2β) is a compound in which X1 and X2 are -NH-, one of Y1 and Y2 is a phenylene group, and the other is Rs-Rt-Rs. Formulas (1-3γ) and (1-3δ) are compounds in which one of X1 and X2 is -O-, the other is -NH-, one of Y1 and Y2 is a phenylene group, and the other is Rs-Rt-Rs.

[0049] [ka] In the formulas (1-3α), (1-3β), (1-3γ) and (1-3δ), Z 10 ~Z 19 , Z 20 ~Z 21 and Z 23 ~Z 24 are each independently a hydrogen atom, -OH, or -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a, a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4) or a group represented by formula (5), and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, with the proviso that Z 10 ~Z 24 At least one of the groups is a group represented by any one of formulas (2) to (5). Z t are each independently a group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -S(=O)2NH-, -NHS(=O)2-, -NH-C(=O)-, and -C(=O)NH-.

[0050] Z 10 ~Z 19 , Z 20 ~Z 21 and Z 23 ~Z 24 With regard to the group other than the group represented by any one of formulas (2) to (5), a hydrogen atom, an alkyl group or a halogen atom is preferred, and a hydrogen atom is more preferred.

[0051] Z 10 ~Z 19 , Z 20 ~Z 21 and Z 23 ~Z 24 It is preferred that one or two of the groups are groups represented by any one of formulas (2) to (5), and Z 10 ~Z 19 It is preferred that one or two of these be a group represented by any one of formulas (2) to (5).

[0052] Z 10 ~Z 19 , Z 20 ~Z 21 and Z 23 ~Z 24 When one or two of the groups are any of (2) to (5), Z 10 ~Z 14 is a group represented by any one of formulas (2) to (5), and Z 15 ~Z 19may be a group represented by any one of formulas (2) to (5), and preferably, Z 10 ~Z 19 Among them, Z 12 and Z 17 Either one or both of Z 11 and Z 16 Either one or both of these, or Z 13 and Z 18 Either one or both of the following is a group represented by any one of formulas (2) to (5): A group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a The monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, and is preferably a hydrogen atom, an alkyl group, or a halogen atom, more preferably a hydrogen atom.

[0053] The compound of formula (1) includes compounds represented by formulas (1-4α), (1-4β), (1-4γ), and (1-4δ). Formula (1-4α) is a compound in which X1 and X2 are -O-, one of Y1 and Y2 is a phenylene group, and the other is a single bond. Formula (1-4β) is a compound in which X1 and X2 are -NH-, one of Y1 and Y2 is a phenylene group, and the other is a single bond. Formulas (1-4γ) and (1-4δ) are compounds in which one of X1 and X2 is -O-, the other is -NH-, one of Y1 and Y2 is a phenylene group, and the other is a single bond.

[0054] [ka] In the formulas (1-4α), (1-4β), (1-4γ) and (1-4δ), Z 10 ~Z 14 are each independently a hydrogen atom, -OH, or -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a , a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4) or a group represented by formula (5), and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, with the proviso that Z 10 ~Z 29 At least one of the groups is a group represented by any one of formulas (2) to (5). Z t are each independently a group selected from a single bond, —O—, —C(═O)O—, —OC(═O)—, —S—, —S(═O)2O—, —OS(═O)2—, —NH—C(═O)—, and —C(═O)NH—. R u represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, and these groups may be substituted, and are preferably a hydrogen atom.

[0055] Z 10 ~Z 14 With regard to the group other than the group represented by any one of formulas (2) to (5), a hydrogen atom, an alkyl group or a halogen atom is preferred, and a hydrogen atom is more preferred.

[0056] Z10 ~Z 14 It is preferable that one of them is a group represented by any one of formulas (2) to (5).

[0057] Z 10 ~Z 14 When one of the groups is a group represented by any of (2) to (5), Z 11 , Z 12 or Z 13 It is preferable that any one of the following is a group represented by any one of formulas (2) to (5). A group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a The monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, and is preferably a hydrogen atom, an alkyl group, or a halogen atom, more preferably a hydrogen atom.

[0058] The compound of formula (1) includes compounds represented by formulas (1-5α), (1-5β), (1-5γ), and (1-5δ). Formula (1-5α) is a compound in which X1 and X2 are -O-, one of Y1 and Y2 is Rs-Rt-Rs, and the other is a single bond. Formula (1-4β) is a compound in which X1 and X2 are -NH-, one of Y1 and Y2 is Rs-Rt-Rs, and the other is a single bond. Formulas (1-5γ) and (1-5δ) are compounds in which one of X1 and X2 is -O-, the other is -NH-, one of Y1 and Y2 is Rs-Rt-Rs, and the other is a single bond.

[0059] [ka] In the formulas (1-5α), (1-5β), (1-5γ) and (1-5δ), Z 10 ~Z 14 , Z 20 ~Z 21 and Z 23 ~Z 24 are each independently a hydrogen atom, -OH, or -OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2OR d , -OS(=O)2R d , -SO3M a , a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4) or a group represented by formula (5), and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, with the proviso that Z 10 ~Z 14 , Z 20 ~Z 21 and Z 23 ~Z 24 At least one of the groups is a group represented by any one of formulas (2) to (5). Z t are each independently a group selected from a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -S(=O)2NH-, -NHS(=O)2-, -NH-C(=O)-, and -C(=O)NH-. R u represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, and these groups may be substituted, and are preferably a hydrogen atom.

[0060] Z 10 ~Z 14 , Z 20 ~Z 21 and Z 23 ~Z 24 With regard to the group other than the group represented by any one of formulas (2) to (5), a hydrogen atom, an alkyl group or a halogen atom is preferred, and a hydrogen atom is more preferred.

[0061] Z 10 ~Z 14 , Z 20 ~Z 21 and Z 23 ~Z 24 is preferably a group represented by any one of formulas (2) to (5), and Z 10 ~Z 14 It is more preferable that one of them is a group represented by any one of formulas (2) to (5).

[0062] Z 10 ~Z 14 , Z 20 ~Z 21 and Z 23 ~Z 24 When one of the groups is a group represented by any one of formulas (2) to (5), Z 10 ~Z 14 is preferably a group represented by any one of formulas (2) to (5), and Z 11 , Z 12 or Z 13 It is more preferable that any one of the following is a group represented by any one of formulas (2) to (5). A group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR a , -SX a , -NR b R c , -NX b -C(=O)X d , -C(=O)NR b R c , halogen atoms, -CN, -NO2, -COOH, -C(=O)OR d , -OC(=O)R d , -COOM a , -SO3H, -S(=O)2ORd , -OS(=O)2R d , -SO3M a The monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted, and is preferably a hydrogen atom, an alkyl group, or a halogen atom, more preferably a hydrogen atom.

[0063] Specific examples of formula (1) include the following: [ka] JPEG2025123096000016.jpg245157JPEG2025123096000017.jpg255168JPEG2025123096000018.jpg255160JPEG2025123096000019.jpg255165JPEG2025123096000020.jpg255163JPEG2025123096000021.jpg242170JPEG2025123096000022.jpg254170JPEG2025123096000023.jpg199170JPEG2025123096000024.jpg244170JPEG2025123096000025.jpg255168JPEG2025123096000026.jpg253170JPEG2025123096000027.jpg250170JPEG2025123096000028.jpg255163JPEG2025123096000029.jpg222170JPEG2025123096000030.jpg255170JPEG2025123096000031.jpg243170JPEG2025123096000032.jpg255158JPEG2025123096000033.jpg215170JPEG2025123096000034.jpg255163JPEG2025123096000035.jpg240170JPEG2025123096000036.jpg246170JPEG2025123096000037.jpg243170JPEG2025123096000038.jpg239170JPEG2025123096000039.jpg255170JPEG2025123096000040.jpg247170JPEG2025123096000041.jpg255170JPEG2025123096000042.jpg250170JPEG2025123096000043.jpg249170JPEG2025123096000044.jpg229170JPEG2025123096000045.jpg39170

[0064] <Manufacturing Method> The anthraquinone compound of the present invention can be obtained by reacting a hydroxy compound having an anthraquinone substituent or an amino compound having an anthraquinone substituent with terephthalic acid or a derivative thereof.

[0065] Examples of hydroxy compounds having an anthraquinone substituent include compounds represented by formulae (2A), (3A), (4A), and (5A). Examples of amino compounds having an anthraquinone substituent include compounds represented by formulae (2B), (3B), (4B), and (5B).

[0066] [ka] JPEG2025123096000047.jpg135170 In formulas (2A), (2B), (3A), (3B), (4A), (4B), (5A) and (5B), R5, R6, R7, R8, L, s, t, u, and v are defined as in formulae (2) to (5), Y has the same meaning as Y1 or Y2 in formula (1). Conventionally known compounds can be used as the compounds represented by formulae (2A), (2B), (3A), (3B), (4A), (4B), (5A) and (5B).

[0067] In addition, the compound represented by (5A) can be obtained, for example, by the method described in JP-A-2013-217964, and the compound represented by (5B) can be obtained, for example, by the method described in U.S. Pat. No. 2,701,802.

[0068] A compound of formula (1) in which X1 or X2 is -O- can be obtained by reacting a hydroxy compound having an anthraquinone substituent with terephthalic acid or a derivative thereof, and a compound of formula (1) in which X1 or X2 is -NH- can be obtained by reacting an amino compound having an anthraquinone substituent with terephthalic acid or a derivative thereof.

[0069] The amino compound having an anthraquinone substituent or the hydroxy compound having an anthraquinone substituent and the terephthalic acid or a derivative thereof may be used in an amount such that the amount of the amino compound or the hydroxy compound is in excess of the amount of the terephthalic acid or the derivative thereof.

[0070] The reaction temperature can be set to 0 to 120° C., and preferably 10 to 80° C. The reaction time can be set to 0.1 to 40 hours, and more preferably 0.5 to 10 hours. The reaction can be carried out under a nitrogen atmosphere.

[0071] The reaction can be carried out using a dehydration condensation agent. The dehydration condensation agent is not particularly limited, and examples thereof include carbodiimides such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide that is not a hydrochloride salt. Furthermore, additives such as 1-hydroxybenzotriazole and N,N-dimethylaminopyridine can be used.

[0072] The reaction is preferably carried out in a solvent, such as amide solvents like N-methyl-2-pyrrolidone, N,N-dimethylacetamide, and dimethylformamide; hydrocarbon solvents like toluene and xylene; halogenated hydrocarbon solvents like chlorobenzene, dichlorobenzene, and chloroform; ketone solvents like methyl isobutyl ketone; ether solvents like tetrahydrofuran and 1,4-dioxane; and nitrile solvents like acetonitrile, among which amide solvents are preferred.

[0073] After the reaction, the resulting product may be subjected to post-treatment and purification, as necessary, to isolate the target compound, for example, by filtration, washing, extraction, concentration under reduced pressure, recrystallization, distillation, column chromatography, etc.

[0074] A specific example of this method is the following scheme. [ka]

[0075] Alternatively, the anthraquinone compounds of the present invention can be reacted with a carboxylic acid compound having an anthraquinone substituent and a compound of formula (6A) or (6B) or a derivative thereof. [ka]

[0076] The compound of formula (6A) can be synthesized, for example, by the method described in Japanese Patent No. 5330013.

[0077] It is known that the compound of formula (6B) can be synthesized by the following reaction. [ka]

[0078] The compound of formula (6B) can also be synthesized by hydrolyzing polyethylene terephthalate (PET), for example, by the method described in Polymer Chemistry (2013), 4(5), 1610-1616.

[0079] Carboxylic acid compounds having an anthraquinone substituent include compounds represented by formulae (2C), (3C) and (4C). [ka] In formulas (2C), (3C), (4C) and (5C), R5, R6, R7, R8, L, s, t, u, and v are defined as in formulae (2) to (5), Y has the same meaning as Y1 or Y2 in formula (1).

[0080] The carboxylic acid compound having an anthraquinone substituent and the compound represented by formula (6A) or (6B) or a derivative thereof may be used in an amount such that the amount of the carboxylic acid compound is in excess of the amount of the compound represented by formula (6A) or (6B) or a derivative thereof.

[0081] The reaction temperature can be 80 to 150° C., and preferably 90 to 110° C. The reaction time can be 1 to 24 hours, and more preferably 12 to 20 hours. The reaction can be carried out under a nitrogen atmosphere.

[0082] The reaction can be carried out using a dehydrating condensation agent in a solvent, and the dehydrating condensation agent and solvent used can be the same as those used in the above method.

[0083] After the reaction, the resulting product may be subjected to post-treatment and purification treatment, if necessary, using the treatments listed above.

[0084] A specific example of this method is the following scheme. [ka]

[0085] In the anthraquinone compound of the present invention, when X1 and X2 are -S-, etc., the compound can be synthesized in the same manner as above. For example, by using a thiol compound having an anthraquinone substituent, a compound in which X1 and X2 are -S- can be obtained.

[0086] In the anthraquinone compound of the present invention, anthraquinone compounds having different numbers of anthraquinone substituents can be produced by changing the equivalent ratio of the compound having an anthraquinone substituent to the compound represented by formula (6A) or (6B) or a derivative thereof, etc. For example, by using a compound having two or more equivalents of anthraquinone substituents, an anthraquinone compound of the present invention having two anthraquinone substituents as described above can be obtained, and by using an anthraquinone compound in an amount of one or less equivalent, an anthraquinone compound of the present invention having one anthraquinone substituent can be obtained.

[0087] Alternatively, the anthraquinone compound of the present invention having an anthraquinone substituent represented by formula (5) can also be obtained by reacting anthraquinone-2,3-dicarboxylic anhydride or a derivative thereof with N,N'-bis(4-aminophenyl)terephthalamide, bis(4-aminophenyl)terephthalate, or the like to obtain an amic acid compound, and then imidizing the amic acid compound.

[0088] The amic acid compound can be obtained by mixing and stirring anthraquinone-2,3-dicarboxylic anhydride or a derivative thereof with N,N'-bis(4-aminophenyl)terephthalamide, bis(4-aminophenyl)terephthalate, or the like in a solvent such as those described above. The reaction temperature can be set to 0°C to 100°C, and the reaction time can be set to 1 to 40 hours. Imidization can be performed using a chemical imidization method or a thermal imidization method under conventionally known reaction conditions.

[0089] <Colored composition and cured product> The anthraquinone compound of the present invention can be used in the production of various paints, water-based or oil-based inks, etc., and is also useful as a functional dye for recording materials, etc. In particular, the anthraquinone compound of the present invention can be used as a pigment because it is insoluble in solvents such as acetone, alcohol, and water.

[0090] The present invention also relates to a coloring composition containing the anthraquinone compound of the present invention. The coloring composition contains the anthraquinone compound of the present invention alone or in any combination of two or more kinds in any ratio.

[0091] The coloring composition may contain a coloring material other than the anthraquinone compound of the present invention. The coloring material is not particularly limited, and known pigments and dyes can be used. For example, Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Purple pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Yellow pigments such as CI Pigment Yellow 24, 93, 108, 110, 120, 138, 147, 185, 193; Examples include green pigments such as CI Pigment Green 7, 36, 58, and 59. Examples of such dyes include compounds classified as having a hue other than CI pigments, and known dyes described in Dyeing Notes (Shikisensha).Furthermore, examples of such dyes, based on their chemical structure, include azo dyes, anthraquinone dyes, cyanine dyes, phthalocyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes.

[0092] Coloring materials other than the anthraquinone compound of the present invention can be used in amounts that do not impair the effects of the present invention.

[0093] The coloring composition of the present invention may contain a binder resin. The binder resin is not particularly limited, and examples thereof include natural polymer materials such as gelatin, casein, starch, cellulose derivatives, and alginic acid; synthetic polymer materials such as polymethyl methacrylate, polyvinyl butyral, polyvinylpyrrolidone, polyvinyl alcohol, polyvinyl chloride, styrene-butadiene copolymer, polystyrene, polyester, polyether, polycarbonate, polyamide, polyimide, polyurethane, melamine resin, and cyclic olefin resin; and adhesives.

[0094] The amount of the binder resin is not particularly limited, and can be, for example, 0.1 to 20 parts by mass per 100 parts by mass of the anthraquinone compound of the present invention. The binder resin may be used alone or in combination of two or more kinds in any ratio.

[0095] The coloring composition of the present invention may contain a solvent. The solvent is not particularly limited, and examples thereof include the following: Examples of suitable alcohols include glycol ethers such as cellosolve, methyl cellosolve, butyl cellosolve, carbitol, methyl carbitol, ethyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol diethyl ether, diethylene glycol monomethyl ether acetate, and tripropylene glycol monomethyl ether; esters such as ethyl acetate, butyl acetate, butyl lactate, cellosolve acetate, butyl cellosolve acetate, carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, and propylene carbonate; and alcohols such as methanol, ethanol, n-propanol, isopropanol, ethylene glycol, propylene glycol, 3-methoxy-1-butanol, ethylene glycol monobutyl ether, 3-hydroxy-2-butanone, and diacetone alcohol.

[0096] The coloring composition of the present invention can be suitably used as a curable composition. For example, a photosensitive coloring composition may be prepared by blending a photosensitive resin and a photosensitizer such as a photopolymerization initiator into the coloring composition of the present invention. Since the anthraquinone compound of the present invention has reduced light absorption in the ultraviolet region (particularly, a wavelength of 365 nm), it is unlikely to affect the photoreaction of the photosensitive coloring composition and can be suitably used. The photosensitive coloring composition may further contain a photosensitive monomer.

[0097] The photosensitive resin may be a resin having an ethylenically unsaturated bond in the molecule. The ethylenically unsaturated group is preferably derived from acrylic acid, methacrylic acid, or a derivative thereof. In order to impart alkaline developability, the photosensitive resin preferably further has an alkali-soluble group such as a phenolic hydroxyl group or a carboxyl group, and more preferably has a carboxyl group. The photosensitive resin is not particularly limited, and examples thereof include the compounds listed below.

[0098] (1) A carboxylic acid-containing copolymer resin obtained by copolymerizing an unsaturated carboxylic acid such as (meth)acrylic acid with one or more other compounds having an unsaturated double bond; (2) Carboxylic acid-containing photosensitive resins obtained by adding ethylenically unsaturated groups as pendants to copolymers of unsaturated carboxylic acids such as (meth)acrylic acid and one or more other compounds having unsaturated double bonds using compounds having epoxy groups and unsaturated double bonds such as glycidyl (meth)acrylate or 3,4-epoxycyclohexylmethyl (meth)acrylate, or (meth)acrylic acid chloride, etc. (3) A photosensitive carboxylic acid-containing copolymer resin obtained by reacting a copolymer of a compound having an epoxy group and an unsaturated double bond, such as glycidyl (meth)acrylate or 3,4-epoxycyclohexylmethyl (meth)acrylate, with another compound having an unsaturated double bond, with an unsaturated carboxylic acid, such as (meth)acrylic acid, and then reacting the resulting secondary hydroxyl group with a polybasic acid anhydride. (4) A carboxylic acid-containing photosensitive resin obtained by reacting a copolymer of an acid anhydride having an unsaturated double bond, such as maleic anhydride, and another compound having an unsaturated double bond with a compound having a hydroxyl group and an unsaturated double bond, such as 2-hydroxyethyl (meth)acrylate. (5) A carboxylic acid-containing photosensitive resin obtained by reacting a polyfunctional epoxy compound with an unsaturated monocarboxylic acid and then reacting the resulting hydroxyl group with a saturated or unsaturated polybasic acid anhydride. (6) A hydroxyl group- and carboxylic acid-containing photosensitive resin obtained by reacting a hydroxyl group-containing polymer such as a polyvinyl alcohol derivative with a saturated or unsaturated polybasic acid anhydride, and then reacting the resulting carboxylic acid with a compound having an epoxy group and an unsaturated double bond in one molecule; (7) A carboxylic acid-containing photosensitive resin obtained by reacting a reaction product of a polyfunctional epoxy compound, an unsaturated monocarboxylic acid, and a compound having at least one alcoholic hydroxyl group and one reactive group other than the alcoholic hydroxyl group that reacts with an epoxy group in one molecule with a saturated or unsaturated polybasic acid anhydride; (8) A carboxylic acid-containing photosensitive resin obtained by reacting an unsaturated monocarboxylic acid with a polyfunctional oxetane compound having at least two oxetane rings in one molecule, and then reacting a saturated or unsaturated polybasic acid anhydride with the primary hydroxyl group in the resulting modified oxetane resin. (9) A carboxylic acid-containing photosensitive resin obtained by reacting a polyfunctional epoxy resin with an unsaturated monocarboxylic acid, followed by reaction with a polybasic acid anhydride, to obtain a carboxylic acid-containing resin, and then reacting the resulting resin with a compound having one oxirane ring and one or more ethylenically unsaturated groups in the molecule; and (10) Carboxylic acid-containing photosensitive resins obtained by reacting a polyfunctional phenolic resin with an alkylene oxide or a cyclic carbonate, reacting the resulting reaction product with a monocarboxylic acid having an unsaturated double bond, and then reacting the resulting reaction product with a saturated or unsaturated polybasic acid anhydride, etc., but are not limited to these.

[0099] The amount of the photosensitive resin can be, for example, 100 to 200 parts by mass per 0.1 to 10 parts by mass of the anthraquinone compound of the present invention. The photosensitive resin may be used alone or in combination of two or more kinds in any ratio.

[0100] The photosensitive monomer is not particularly limited and may be a compound having an ethylenically unsaturated double bond. Examples include polyester (meth)acrylate, polyether (meth)acrylate, urethane (meth)acrylate, carbonate (meth)acrylate, and epoxy (meth)acrylate. Specific examples include hydroxyalkyl acrylates such as 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate; glycol diacrylates such as ethylene glycol, methoxytetraethylene glycol, polyethylene glycol, and propylene glycol; acrylamides such as N,N-dimethylacrylamide, N-methylolacrylamide, and N,N-dimethylaminopropylacrylamide; aminoalkyl acrylates such as N,N-dimethylaminoethyl acrylate and N,N-dimethylaminopropyl acrylate; polyhydric alcohols such as hexanediol, trimethylolpropane, pentaerythritol, dipentaerythritol, and tris-hydroxyethyl isocyanurate, and their ethyleneoxide adducts; and propylene oxide. Examples of suitable photosensitive monomers include polyhydric acrylates such as ethylene oxide adducts and ε-caprolactone adducts of phenoxy acrylate, bisphenol A diacrylate, and ethylene oxide adducts and propylene oxide adducts of these phenols; polyhydric acrylates of glycidyl ethers such as glycerin diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, and triglycidyl isocyanurate; acrylates obtained by directly acridating polyols such as polyether polyols, polycarbonate diols, hydroxyl-terminated polybutadienes, and polyester polyols, or by urethane acrylate via diisocyanates, melamine acrylates, and methacrylates corresponding to the above acrylates. The photosensitive monomers may be used alone or in combination. These photosensitive monomers can also be used as reactive diluents.

[0101] The amount of the photosensitive monomer can be, for example, 0.1 to 60 parts by mass relative to 0.1 to 10 parts by mass of the anthraquinone compound of the present invention. The photosensitive resin may be used alone or in combination of two or more kinds in any ratio.

[0102] The photopolymerization initiator is not particularly limited, and examples thereof include oxime ester-based photopolymerization initiators having an oxime ester group (e.g., Irgacure OXE02 manufactured by BASF Japan Ltd.), alkylphenone-based photopolymerization initiators (e.g., Irgacure 907 manufactured by BASF Japan Ltd.), and acylphosphine oxide-based photopolymerization initiators (e.g., Irgacure TPO manufactured by BASF Japan Ltd.).

[0103] The amount of the photopolymerization initiator can be, for example, 0.1 to 10 parts by mass relative to 0.1 to 10 parts by mass of the anthraquinone compound of the present invention. The photopolymerization initiator may be used alone or in combination of two or more kinds in any ratio.

[0104] The anthraquinone compound of the present invention has excellent heat resistance, and the coloring composition of the present invention may be blended with a thermosetting resin to form a thermosetting coloring composition. The thermosetting resin is not particularly limited, and a known thermosetting resin can be used. In addition, a thermosetting catalyst may be blended with the thermosetting coloring composition.

[0105] The coloring composition of the present invention may contain components other than those described above, as long as the effects of the present invention are not impaired. Examples of components other than those described above include surfactants, polymerization inhibitors, antioxidants, fillers, adhesion promoters, and ultraviolet absorbers. [Example]

[0106] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0107] <Synthesis of Compound 1> [ka]

[0108] A 300 mL two-neck flask was charged with 1-((4-hydroxyphenyl)amino)-4-(methylamino)anthracene-9,10-dione (6.10 g, 17.7 mmol), 4-dimethylaminopyridine (2.21 g, 18.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.73 g, 19.5 mmol), and N-methylpyrrolidone (100 mL). The mixture was heated to 50 °C under a nitrogen atmosphere. After that, a solution of terephthalic acid (1.32 g, 7.95 mmol) in N-methylpyrrolidone (30 mL) was added and reacted at 50 °C for 1 hour under a nitrogen atmosphere. The reaction mixture was filtered, and the resulting solid was washed with acetone (100 mL) and dried under reduced pressure at 100 °C for 15 hours to obtain compound 1 (2.54 g, 3.10 mmol).

[0109] FT-IR: Wave number (cm -1 ) = 3100-3000 (aromatic CH), 1730 (ester C=O) The chart is shown in Figure 1.

[0110] Identification was performed using peaks obtained in positive mode by electron spray ionization on an LC-TofMS (Waters, Xevo G2-S). MS(m / z)=819.25[M+H] +

[0111] <Compound 2> [ka]

[0112] 1-((4-aminophenyl)amino)-4-(methylamino)anthracene-9,10-dione (1.89 g, 5.50 mmol), 4-dimethylaminopyridine (0.710 g, 5.82 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.14 g, 5.96 mmol), and N-methylpyrrolidone (40 mL) were added to a 100 mL two-neck flask and heated to 50°C under a nitrogen atmosphere. After that, a solution of terephthalic acid (0.427 g, 2.57 mmol) dissolved in N-methylpyrrolidone (10 mL) was added, and the reaction was carried out at 50°C under a nitrogen atmosphere for 1 hour. After adding 20 mL of ion-exchanged water to the reaction solution, the solid obtained by filtration was washed successively with ion-exchanged water (50 mL) and acetone (100 mL) and dried at 100°C under reduced pressure for 15 hours to obtain compound 2 (1.28 g, 1.57 mmol).

[0113] FT-IR: Wave number (cm -1 ) = 3100-3000 (aromatic CH), 1640 (amide C=O) The chart is shown in Figure 2.

[0114] Compound 2 was identified from a peak obtained in positive mode by electron spray ionization using LC-TofMS (Waters, Xevo G2-S). MX(m / z)=817.27[M+H] +

[0115] <Compound 3> [ka]

[0116] 0.7 mmol of 4-[[9,10-dihydro-4-(methylamino)-9,10-dioxo-1-anthracenyl]amino]benzoic acid, 0.79 mol of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.79 mmol of 1-hydroxybenzotriazole, and 2.8 mL of N-methylpyrrolidone were mixed and heated under a nitrogen atmosphere. After stirring at 60°C for 30 minutes, the N 1 ,N4 0.28 mmol of N,N'-bis(4-hydroxyphenyl)-1,4-benzenedicarboxamide and 0.7 mmol of N,N'-dimethylformamide were added and reacted. After stirring at 90°C for 15 hours, the mixture was cooled to room temperature. The reaction solution was filtered to obtain a solid, which was washed with 15 mL of N-methylpyrrolidone. After further washing with 15 mL of ethanol, the solid was dried at 100°C under reduced pressure for 15 hours to obtain 0.09 mmol of compound 1.

[0117] FT-IR: Wave number (cm -1 ) = 3340 (amine NH), 3100-3000 (aromatic CH), 1720 (ester C=O), 1640 (amide C=O) The chart is shown in Figure 3.

[0118] Compound 3 was identified from the peak obtained by laser desorption ionization in positive mode using a time-of-flight mass spectrometer (rapifleX (TOF-MS, Bruker Daltonics)). MS (m / z) = 1058.4 ([M+H] + )

[0119] The obtained compound was subjected to the heat resistance temperature measurement by thermogravimetry and the light absorption measurement in the ultraviolet region.In addition, the heat resistance of the dried film of the composition containing the obtained compound was evaluated.In some tests, for comparison, the following compound 4 and compound 5 were also subjected to the same evaluation. Compound 4: Solvent Blue 11 [ka] Compound 5: Pigment Blue 15:3 [ka]

[0120] (Heat-resistant temperature measurement) The onset temperature of each compound was measured by thermogravimetry using a thermogravimetric analyzer (Waters, model name: TGA5500) and was used as the heat resistance temperature. The sample weight used for each measurement was 1-2 mg. The temperature was raised from 50°C to 600°C at a rate of 10°C per minute under a nitrogen atmosphere.

[0121] [Table 1]

[0122] The heat resistance temperature of compounds 1 to 3 was higher than that of compound 4, and they were excellent in heat resistance.

[0123] (Dry film absorbance measurement and heat resistance test: reflow 260℃, 3 times) A mixture of 1 g each of Compound 1, Compound 2, Compound 4, and Compound 5 and 19 g of dipropylene glycol monomethyl ether was mixed with 30 g of 0.3 mm zirconia beads and dispersed for 2 hours using a rocking mill. 3 g of this dispersion was added to 10 g of resin (Daicel Chemical's Cyclomer P (ACA) Z320) to prepare a solution. The resulting solution was applied to a glass plate using a 60 μm gap applicator and prebaked in a circulating drying oven at 90°C for 30 minutes to obtain a dried film. The absorbance of the obtained dried films was measured using a JASCO V-570 equipped with an integrating sphere. As shown in Figure 4, the dried films of Compounds 1 and 2 had significantly reduced light absorption in the UV region compared to the dried film of Compound 5. The film was then placed in a reflow tester (NIS-20-82C). The test conditions were 260°C in an air atmosphere, and the treatment was carried out three times. The film before and after the treatment was measured using a Konica Minolta CM-5 in the L*a*b* color system to determine ΔE*ab. ΔE*ab is calculated using the following formula: ΔE*ab=〔(ΔL*) 2 +(Δa*) 2 +(Δb*) 2 〕 1 / 2

[0124] [Table 2]

[0125] The dried films containing compounds 1 and 2 showed significantly less discoloration before and after the heat resistance test than compound 4, and had heat resistance comparable to that of compound 5.

[0126] (light absorption in the ultraviolet region) Solutions were prepared by dissolving Compound 1, Compound 2, and Compound 4 in NMP as a solvent so that the maximum absorbance was 0.1 or more and less than 1. The absorption spectrum of the prepared solution was measured using a spectrophotometer (manufactured by JASCO Corporation, instrument name: V-570). The spectrum normalized by the maximum absorbance is shown in Figure 5.

[0127] Compounds 1 and 2 exhibited reduced light absorption in the ultraviolet region (particularly at a wavelength of 365 nm). [Industrial Applicability]

[0128] The anthraquinone compound of the present invention has excellent heat resistance, and also has suppressed light absorption in the ultraviolet region (particularly, a wavelength of 365 nm). Due to these properties, the coloring composition of the present invention can be suitably used as a curable composition, and the coloring composition of the present invention can be suitably used as a curable composition, and is particularly suitable for a photosensitive coloring composition, and is highly useful in industry.

Claims

1. An anthraquinone compound represented by the following formula (1): 【Chemical 1】 In formula (1), X １ and X ２ are each independently —O—, —NH—, or —S—, Y １ is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R ｓ -R ｔ -R ｓ wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y １ is a single bond, Y ２ is an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R ｓ -R ｔ -R ｓ wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted; or Y ２ is a single bond, Here, R ｓ each independently represents an alkyl group having 1 to 6 carbon atoms, a phenyl group, or an aralkyl group, and the alkyl group having 1 to 6 carbon atoms, the phenyl group, and the aralkyl group are optionally substituted; R ｔ represents a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O) ２ O-, -S(=O) ２ NH-, -NHS (=O) ２ -, -OS (=O) ２ is a group selected from -, -NH-C(=O)- and -C(=O)NH-, R １ and R ２ are each independently a hydrogen atom, —OH, —OR ａ , -SX ａ , -NR ｂ R ｃ , -NX ｂ -C(=O)X ｄ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2), a group represented by formula (3), a group represented by formula (4), and a group represented by formula (5), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted; R ３ are each independently —OH, —OR ａ , -SX ａ , -NR ｂ R ｃ , -NX ｂ -C(=O)X ｄ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, which may be substituted; p is an integer from 1 to 9, q is an integer from 1 to 9, r is an integer from 0 to 4; R ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, which may be substituted; R ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; R ｄ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, which may be substituted; M ａ is sodium or potassium, however, Formula (1) has at least one group selected from the group represented by formula (2), the group represented by formula (3), the group represented by formula (4), and the group represented by formula (5). 【Chemistry 2】 In formulas (2) to (5), R ５ and R ６ are each independently —OH, —OX ａ , -SX ａ , -NX ｂ X ｃ , -NX ｂ -C(=O)X ｄ , -C(=O)NX ｂ X ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , —O—S(═O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms may be substituted; R ７ are each independently a hydrogen atom, —C(═O)Xe, —C(═O)OXe, or —C(═O)OM ｂ , an alkyl group, an aralkyl group, or a monovalent aromatic cyclic group, and the alkyl group, aralkyl group, and monovalent aromatic cyclic group may be substituted; ７ may be linked to each other to form a ring, L is a single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, or -S(=O) ２ O-, -S(=O) ２ NH-, -NHS (=O) ２ -, -OS (=O) ２ a linking group selected from -, -NH-C(=O)-, and -C(=O)NH-; s is an integer from 0 to 3; t is an integer from 0 to 4, u is an integer from 0 to 3; v is an integer from 0 to 2, X ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, which may be substituted; X ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X ｄ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, which may be substituted; Xe is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic cyclic group, and these groups may be substituted; X ｆ represents a single bond, an alkylene group, an alkenylene group, an alkynylene group, an aralkylene group or a divalent aromatic ring group, and these groups may be substituted; M ｂ is sodium or potassium.

2. The anthraquinone compound according to claim 1, wherein the formula (1) has at least two groups selected from the group represented by the formula (2), the group represented by the formula (3), the group represented by the formula (4), and the group represented by the formula (5).

3. Formula (1) is a group represented by formula (2), a group represented by formula (3), a group represented by formula (4), and a group represented by formula (5), １ and R is a group selected from the group represented by formula (2), the group represented by formula (3), the group represented by formula (4), and the group represented by formula (5). ２ The anthraquinone compound according to claim 2, having at least one of the following:

4. A coloring composition containing the anthraquinone compound according to claim 1.

5. The colored composition according to claim 4, further comprising a coloring material other than the anthraquinone compound according to claim 1.

6. The coloring composition according to claim 4, which is a photosensitive coloring composition.

7. The coloring composition according to claim 5, which is a photosensitive coloring composition.

8. A cured product of the colored composition according to any one of claims 4 to 7.

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