Anthraquinone compound, coloring composition, and cured product

Abstract

Provided is a novel anthraquinone compound. The anthraquinone compound is represented by formula (1).

Description

Anthraquinone compound, colored composition and cured product

[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.

[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. However, it is difficult to achieve pure RGB hues using a single coloring material. Therefore, efforts have been made to blend multiple coloring materials to approximate the desired RGB hues. Furthermore, attempts have also been made to blend multiple coloring materials to achieve the desired hues in solder resists for printed wiring boards.

[0003] Known colorants used in color filters and solder resists include a copper phthalocyanine pigment such as Pigment Blue 15. A colored photosensitive resin composition capable of forming a highly bright color filter using copper phthalocyanine has also been proposed (Patent Document 1).

[0004] In addition, Solvent Blue 11, an anthraquinone dye, and the like are also known, and a photosensitive resin that uses a specific anthraquinone compound and has excellent sensitivity, storage stability after lamination onto a substrate, and hue stability has also been proposed (Patent Document 2).

[0005] JP 2019-152852 A JP 2013-57902 A

[0006] Copper phthalocyanine pigments have good heat resistance, but have the problem of large light absorption in the ultraviolet region (particularly at a wavelength of 365 nm). On the other hand, anthraquinone dyes have the problem of poor heat resistance. Under these circumstances, there is a demand for novel compounds that can function as colorants. 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.

[0007] As a result of extensive investigations, the present inventors have found 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), and have thus completed the present invention.

[0008] The gist of the present invention is as follows: [1] An anthraquinone compound represented by the following formula (1): In formula (1), X １ and X ２ are each independently —O—, —NH—, or —S—, and 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, and 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, where R ｓ are each independently 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 may be 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 -, -NHC(=O)- and -C(=O)NH-, R １ and R ２ are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NRｂ -C(=O)R 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 , -OS(=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 may be substituted; R ３ are each independently —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ -C(=O)R 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 , -OS(=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 of 1 to 9; q is an integer of 1 to 9; r is an integer of 0 to 4; R ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic ring group, which may be substituted; R ｂrepresents 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; R ｃ 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; R ｄ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, which may be substituted; M ａ is sodium or potassium, and with the proviso that 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). 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 , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, 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)X ｅ , -C(=O)OX ｅ , -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 bonded 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-, s is an integer of 0 to 3, t is an integer of 0 to 4, u is an integer of 0 to 3, v is an integer of 0 to 2, X ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring 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 ring 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 ring 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 ring group, which may be substituted; X ｅ 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; M ｂ is sodium or potassium, and * is a bond. [2] An anthraquinone compound according to [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] An anthraquinone compound according to [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). 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). ２The anthraquinone compound of [2], having at least one of the following. [4] A coloring composition containing the anthraquinone compound of any of [1] to [3]. [5] The coloring composition of [4], further containing a coloring material other than the anthraquinone compound of [1]. [6] The coloring composition of [4], which is a photosensitive coloring composition. [7] The coloring composition of [5], which is a photosensitive coloring composition. [8] A cured product of the coloring composition of any of [4] to [7].

[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.

[0010] 1 is an FT-IR chart of Example Compound 1. 2 is an FT-IR chart of Example Compound 2. 3 is an FT-IR chart of Example Compound 3. 4 is an absorbance chart of dry films of Example Compounds 1, 2, 4, and 5. 5 is an ultraviolet-visible absorption spectrum chart of solutions of Example Compounds 1, 2, and 4.

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

[0012] <Terminology> In this specification, the alkyl group may be branched or linear and includes, for example, an alkyl group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, specific examples of which 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, a 2-ethylhexyl group, etc. The alkenyl group may be branched or linear and includes, for example, an alkenyl group having 2 to 20 carbon atoms, preferably 2 to 8 carbon atoms, specific examples of which include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a butadienyl group, a pentenyl group, a pentadienyl group, a hexadienyl group, etc. 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 include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, butidienyl, pentynyl, pentidienyl, and 1-hexynyl groups. Aralkyl groups are groups in which one hydrogen atom of an alkyl group is substituted with an aryl group, and examples include aralkyl groups having 7 to 30 carbon atoms. Specific examples include benzyl, methylbenzyl, 1-phenylethyl, and naphthylmethyl groups. Alkylene, alkenylene, and alkynylene groups are divalent groups formed by removing one hydrogen atom from an alkyl group, alkenyl group, or 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 (fluorine atom, chlorine atom, bromine atom, 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 (oxygen atom, nitrogen atom, sulfur atom, etc.) or a bond (ester bond, 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 include a 4- to 20-membered ring, preferably a 4- to 14-membered ring. The carbocycle may be aromatic or non-aromatic, and may be monocyclic or polycyclic. Examples include cycloalkanes (e.g., cyclopropane, cyclopentane, cyclohexane, etc.), arenes (e.g., benzene, naphthalene, etc.), etc. The carbocyclic ring can contain the above-mentioned substituents and hydrocarbon groups. The heterocyclic ring 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, and preferably 4- to 14-membered rings. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms. The heterocyclic ring can be aromatic or non-aromatic, and can be monocyclic or polycyclic. Examples include a pyridine ring, lactone ring, imidazole ring, thiazole ring, and oxazole ring. The heterocyclic ring can contain the above-mentioned substituents and hydrocarbon groups. The aromatic ring can be a carbocyclic ring or a heterocyclic ring, and includes the above-mentioned examples of aromatic rings.

[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). In formulas (2) to (5), R ５ and R ６ are each independently —OH, —OXａ , -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 , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, 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)X ｅ , -C(=O)OX ｅ , -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 bonded 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-, s is an integer of 0 to 3, t is an integer of 0 to 4, u is an integer of 0 to 3, v is an integer of 0 to 2, X ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, which may be substituted; X ｂrepresents 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; X ｃ 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; X ｄ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, which may be substituted; X ｅ 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; M ｂ is sodium or potassium, and * is a bond.

[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. Here, -N(R ７ ) ２ The position where is bonded is the first position.

[0016] In formula (2), L is preferably -O-. In 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), R ５ and / or R ６ When present, each independently represents -NX ｂ X ｃ , —OH, —OXａ or -SX ａ It is preferable that:

[0019] R in formulas (2) to (4) ７ are 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. In formulas (2-1) to (2-4), * represents a bond, and L represents 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-; Z １ ~Z ４ and Z ５ ~Z ７ are each independently 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, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, 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 ７are each independently a hydrogen atom, -C(=O)X ｅ , -C(=O)OX ｅ , -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—. １ ~Z ４ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH or —OX ａ is preferred. ５ ~Z ７ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH or —OX ａ is preferred. ７ are each independently preferably 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. In formulas (3-1) to (3-3), * represents a bond, and L represents 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-; Z １ ~Z ４ and Z ５ ~Z ７ are each independently 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, —NO ２ , -COOH, -C(=O)OXｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, 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)X ｅ , -C(=O)OX ｅ , -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—. １ ~Z ４ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH or —OX ａ is preferred. ５ ~Z ７ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH or —OX ａ is preferred. ７ are each independently preferably a hydrogen atom, an alkyl group, or a monovalent aromatic ring group.

[0024] The anthraquinone substituent of formula (4) can be rewritten as formula (4-1). In formula (4-1), * represents a bond, and L represents 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-; Z１ ~Z ４ and Z ５ ~Z ７ are each independently 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, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, 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)X ｅ , -C(=O)OX ｅ , -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.

[0025] L is preferably a single bond. １ ~Z ４ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH, or —OX ａ is preferred. ５ ~Z ７ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH, —OX ａ , or -SX ａ is preferred. ７ is preferably a hydrogen atom or an alkyl group.

[0026] The anthraquinone substituent of formula (5) can be rewritten as formula (5-1). In formula (5-1), * represents a bond, and L represents 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-; Z １ ~Z ４ , Z ５ and Z ８ are each independently 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, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , -OS(=O) ２ X ｄ , -SO ３ M ｂ and 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. １ ~Z ４ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH, or —OX ａ is preferred. ５ and Z ８ are each independently a hydrogen atom, -NX ｂ X ｃ , —OH, —OXａ , or -SX ａ is preferred.

[0028] <Anthraquinone Compound> The anthraquinone compound of the present invention is represented by formula (1), １ and R ２ has at least one anthraquinone substituent represented by any one of formulas (2) to (5). In formula (1), X １ and X ２ are each independently —O—, —NH—, or —S—, and 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, and 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, where R ｓ are each independently 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 may be 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 -, -NHC(=O)- and -C(=O)NH-, R １ and R ２ are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NRｂ C(=O)R 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 , -OS(=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 may be substituted; R ３ are each independently —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=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 of 1 to 9; q is an integer of 1 to 9; r is an integer of 0 to 4; R ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic ring group, which may be substituted; R ｂrepresents 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; R ｃ 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; R ｄ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, which may be substituted; M ａ is sodium or potassium, and with the proviso that 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 in its 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), and the anthraquinone substituents R １ and an anthraquinone substituent R ２ It is more preferred that the compound has at least one anthraquinone substituent, R １ and an anthraquinone substituent R ２ It is particularly preferred that the compound has one of the following:

[0031] R other than the anthraquinone substituent １ and R ２ is preferably a hydrogen atom.

[0032] In the anthraquinone compound of the present invention, X １ and X ２ is preferably —O— or —NH—, and X １ and X ２ Both of the following are —O— or X １ and X ２It is more preferred that both of the groups are —NH—.

[0033] In the anthraquinone compound of the present invention, 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. 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, where p is an integer from 1 to 9, and q is an integer from 1 to 9.

[0034] Y １ and Y ２ When p or q is 1, it is an alkylene group having 1 to 6 carbon atoms, a phenylene group (1,4-phenylene group, 1,3-phenylene group, etc.), or R ｓ -R ｔ -R ｓ When p or q is 2 to 9, it is a divalent residue derived from an alkyl group having 1 to 6 carbon atoms, a phenyl group, or R ｓ -R ｔ -R ｓ It is a trivalent to decavalent residue obtained by removing 2 to 9 hydrogen atoms from

[0035] R ｓ -R ｔ -R ｓ In this case, R ｓ At least one of R is preferably a phenyl group, ｔ is preferably —C(═O)O—, —OC(═O)—, —C(═O)NH—, or —NHC(═O)—. ｓ are both phenyl groups, and Rt is -C(=O)O-, -OC(=O)-, -C(=O)NH-, or -NHC(=O).

[0036] Y １ and Y ２ can be a single bond. １ is a single bond, p is 1, and R １ is preferably a hydrogen atom. １ When Y is —O—, the terminal is a carboxyl group. ２ is a single bond, q is 1, and R ２ is preferably a hydrogen atom. ２ When it 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 represented by the formula: X １ and X ２ is —O—, and Y １ and Y ２ is a phenylene group. １ and X ２ is —NH—, and Y １ and Y ２ is a phenylene group. １ and X ２ one of the groups is —O— and the other is —NH—; and Y １ and Y ２ is a phenylene group.

[0040] In the formulas (1-1α), (1-1β) and (1-1γ), Z １０ ~Z １９ are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ -C(=O)R ｄ , —C(═O)NR ｂ Rｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , —OC(═O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , -OS(=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) 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 respect 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 preferable that one or two of Z is a group represented by any one of formulas (2) to (5). １０ ~Z １９ When two of the groups are groups represented by any of 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 the above, or Z １３ and Z １８is a group represented by any one of formulas (2) to (5). Any group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=O) ２ R ｄ , -SO ３ M ａ , a monovalent hydrocarbon group having 1 to 30 carbon atoms, which 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 represented by X １ and X ２ is —O—, and Y １ and Y ２ is R ｓ -R ｔ -R ｓ The compound represented by formula (1-2β) is X １ and X ２ is —NH—, and Y １ and Y ２ is R ｓ -R ｔ -R ｓ The compound of formula (1-2γ) is X １ and X ２ one of the groups is —O— and the other is —NH—; and Y １ and Y ２ is R ｓ -R ｔ -R ｓIt is a compound in which

[0044] In the formulas (1-2α), (1-2β) and (1-2γ), Z １０ ~Z １９ , Z ２０ ~Z ２１ , Z ２３ ~Z ２６ and Z ２８ ~Z ２９ are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ -C(=O)R 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 , -OS(=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) 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 Z is a group represented by any one of formulas (2) to (5). ｔ are each independently a single bond, —O—, —C(═O)O—, —OC(═O)—, —S—, or —S(═O) ２ O-, -OS (=O) ２ -, -S(=O) ２ NH-, -NHS (=O) ２ It is a group selected from -, -NHC(=O)- and -C(=O)NH-.

[0045] Z １０ ~Z １９ , Z ２０ ~Z ２１, Z ２３ ~Z ２６ , Z ２８ ~Z ２９ With respect 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 ２９ 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 the groups 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 the above, or Z １３ and Z １８ is a group represented by any one of formulas (2) to (5). Any group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=O) ２ R ｄ , -SO ３ M ａ , a monovalent hydrocarbon group having 1 to 30 carbon atoms, which 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 represented by X １ and X ２ is —O—, and Y １ and Y ２ one of which is a phenylene group and the other is R ｓ -R ｔ -R ｓ The compound represented by formula (1-2β) is X １ and X ２ is —NH—, and Y １ and Y ２ one of which is a phenylene group and the other is R ｓ -R ｔ -R ｓ and the formulas (1-3γ) and (1-3δ) are compounds represented by X １ and X ２ one of the groups is —O— and the other is —NH—; and Y １ and Y ２ one of which is a phenylene group and the other is R ｓ -R ｔ -R ｓ It is a compound in which

[0049] 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 ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ -C(=O)R 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 , -OS(=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) 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 Z is a group represented by any one of formulas (2) to (5). ｔ are each independently a single bond, —O—, —C(═O)O—, —OC(═O)—, —S—, or —S(═O) ２ O-, -OS (=O) ２ -, -S(=O) ２ NH-, -NHS (=O) ２ It is a group selected from -, -NHC(=O)- and -C(=O)NH-.

[0050] Z １０ ~Z １９ , Z ２０ ~Z ２１ and Z ２３ ~Z ２４ With respect 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 ~Z１９ , 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 the groups 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 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 the above, or Z １３ and Z １８ is a group represented by any one of formulas (2) to (5). Any group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ -C(=O)R 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 , -OS(=O) ２ R ｄ , -SO３ M ａ , a monovalent hydrocarbon group having 1 to 30 carbon atoms, which 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 represented by X １ and X ２ is —O—, and Y １ and Y ２ is a phenylene group and the other is a single bond, and the formula (1-4β) is a compound in which X １ and X ２ is —NH—, and Y １ and Y ２ is a phenylene group and the other is a single bond, and the formulas (1-4γ) and (1-4δ) are compounds in which X １ and X ２ one of the groups is —O— and the other is —NH—; and Y １ and Y ２ is a compound in which one of the groups is a phenylene group and the other is a single bond.

[0054] In the formulae (1-4α), (1-4β), (1-4γ) and (1-4δ), Z １０ ~Z １４ are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=O) ２ R ｄ , -SO３ 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) 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 Z is a group represented by any one of formulas (2) to (5). ｔ are each independently a single bond, —O—, —C(═O)O—, —OC(═O)—, —S—, or —S(═O) ２ O-, -OS (=O) ２ is a group selected from -, -NHC(=O)- and -C(=O)NH-. ｕ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, which may be substituted, and is preferably a hydrogen atom.

[0055] Z １０ ~Z １４ With respect 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] Z １０ ~Z １４ It is preferable that one of the groups 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 one of (2) to (5), Z １１ , Z １２ or Z １３ is preferably a group represented by any one of formulas (2) to (5). Any group other than the group represented by any one of formulas (2) to (5) is preferably 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 , -OS(=O) ２ R ｄ , -SO ３ M ａ , a monovalent hydrocarbon group having 1 to 30 carbon atoms, which 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 represented by X １ and X ２ is —O—, and Y １ and Y ２ One of them is R ｓ -R ｔ -R ｓ and the other is a single bond, and the formula (1-4β) is a compound represented by X １ and X ２ is —NH—, and Y １ and Y ２ One of them is R ｓ -R ｔ -R ｓ and the other is a t single bond, and the formulas (1-5γ) and (1-5δ) are compounds represented by X １ and X ２ one of the groups is —O— and the other is —NH—; and Y １ and Y ２ One of them is R ｓ -R ｔ -R ｓ and the other is a single bond.

[0059] In the formulae (1-5α), (1-5β), (1-5γ) and (1-5δ), Z １０ ~Z １４ , Z ２０ ~Z ２１ and Z ２３ ~Z ２４are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=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) 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 Z is a group represented by any one of formulas (2) to (5). ｔ are each independently a single bond, —O—, —C(═O)O—, —OC(═O)—, —S—, or —S(═O) ２ O-, -OS (=O) ２ -, -S(=O) ２ NH-, -NHS (=O) ２ is a group selected from -, -NHC(=O)- and -C(=O)NH-. ｕ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring group, which may be substituted, and is preferably a hydrogen atom.

[0060] Z １０ ~Z １４ , Z ２０ ~Z ２１ and Z ２３ ~Z ２４With respect 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 the groups 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 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 is a group represented by any one of formulas (2) to (5). Any group other than the group represented by any one of formulas (2) to (5) is a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ -C(=O)R 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 , -OS(=O) ２ R ｄ , -SO ３ M ａ, a monovalent hydrocarbon group having 1 to 30 carbon atoms, which 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.

[0064] <Production 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] In formulas (2A), (2B), (3A), (3B), (4A), (4B), (5A) and (5B), R ５ , R ６ , R ７, R ８ , L, s, t, u, and v have the same meanings as in formulas (2) to (5), and Y is Y in formula (1). １ or Y ２ The compounds represented by formulas (2A), (2B), (3A), (3B), (4A), (4B), (5A) and (5B) may be any known compounds.

[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] By reacting a hydroxy compound having an anthraquinone substituent with terephthalic acid or a derivative thereof, X １ or X ２ By reacting an amino compound having an anthraquinone substituent with terephthalic acid or a derivative thereof, a compound represented by the formula (1) in which X is —O— can be obtained. １ or X ２ A compound having —NH— can be obtained.

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

[0070] The reaction temperature can be 0 to 120° C., preferably 10 to 80° C. The reaction time can be 0.1 to 40 hours, 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. Examples of the solvent include amide solvents such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide, and dimethylformamide; hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; ketone solvents such as methyl isobutyl ketone; ether solvents such as tetrahydrofuran and 1,4-dioxane; and nitrile solvents such as 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.

[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.

[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.

[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). In formulas (2C), (3C), (4C) and (5C), R ５ , R ６ , R ７ , R ８ , L, s, t, u, and v have the same meanings as in formulas (2) to (5), and Y is Y in formula (1). １ or Y ２ is synonymous with.

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

[0081] The reaction temperature can be 80 to 150° C., preferably 90 to 110° C. The reaction time can be 1 to 24 hours, 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.

[0085] In the anthraquinone compound of the present invention, X １ and X ２For example, when a thiol compound having an anthraquinone substituent is used, X １ and X ２ A compound having —S— can be obtained.

[0086] In the anthraquinone compound of the present invention, 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., it is possible to produce an anthraquinone compound of the present invention having a different number of anthraquinone substituents. For example, by using a compound having two or more equivalents of anthraquinone substituents, it is possible to obtain an anthraquinone compound of the present invention having two anthraquinone substituents as described above, and by using an anthraquinone compound of one equivalent or less, it is possible to obtain an anthraquinone compound of the present invention having one anthraquinone substituent.

[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] <Coloring 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. It 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 C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, and 265; blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and 60; purple pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, and 38; C.I. Examples of suitable dyes include yellow pigments such as C.I. Pigment Yellow 24, 93, 108, 110, 120, 138, 147, 185, and 193; and green pigments such as C.I. Pigment Green 7, 36, 58, and 59. Examples of suitable dyes include compounds classified as having a hue other than C.I. Pigments, and known dyes described in Dyeing Notes (Shikisensha). In addition, examples of suitable 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 an amount that does 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 may 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 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. A photosensitive monomer may further be blended into the photosensitive coloring composition.

[0097] As the photosensitive resin, a resin having an ethylenically unsaturated bond in the molecule can be used. The ethylenically unsaturated group is preferably derived from acrylic acid or methacrylic acid or a derivative thereof. Furthermore, from the viewpoint of imparting 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) Carboxylic acid-containing copolymer resins 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 an ethylenically unsaturated group as a pendant to a copolymer of an unsaturated carboxylic acid such as (meth)acrylic acid with one or more other compounds having an unsaturated double bond using a compound having an epoxy group and an unsaturated double bond such as glycidyl (meth)acrylate or 3,4-epoxycyclohexylmethyl (meth)acrylate, or (meth)acrylic acid chloride; (3) Carboxylic acid-containing photosensitive resins obtained by copolymerizing an unsaturated carboxylic acid such as (meth)acrylic acid with one or more other compounds having an unsaturated double bond with glycidyl (meth)acrylate or 3,(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, with a compound having an unsaturated double bond, such as maleic anhydride, and a 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 in one molecule at least one alcoholic hydroxyl group and one reactive group other than the alcoholic hydroxyl group that reacts with an epoxy group, with a saturated or unsaturated polybasic acid anhydride; (8) A carboxylic acid-containing photosensitive resin obtained by reacting a polyfunctional oxetane compound having in one molecule at least two oxetane rings with an unsaturated monocarboxylic acid, 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 further reacting the resulting resin with a compound having in one molecule one oxirane ring and one or more ethylenically unsaturated groups; (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., are examples of the photosensitive resins, 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 can 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 of two or more. These photosensitive monomers can also be used as reactive diluents.

[0101] The amount of the photosensitive monomer may 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), alkylphenone-based photopolymerization initiators (e.g., Irgacure 907 manufactured by BASF Japan), and acylphosphine oxide-based photopolymerization initiators (e.g., Irgacure TPO manufactured by BASF Japan).

[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 any 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.

[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>

[0108] Into a 300 mL two-neck flask, 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) were added and heated to 50°C under a nitrogen atmosphere. After that, a solution of terephthalic acid (1.32 g, 7.95 mmol) dissolved in N-methylpyrrolidone (30 mL) was added and reacted for 1 hour at 50°C under a nitrogen atmosphere. The reaction solution 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 C—H), 1730 (ester C═O). The FT-IR chart is shown in FIG.

[0110] Compound 1 was identified from the peak obtained by electron spray ionization in positive mode using LC-TofMS (Waters, Xevo G2-S). MS (m / z) = 819.25 [M+H] ＋

[0111] <Synthesis of Compound 2>

[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 placed in 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 mixture was allowed to react 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 C-H), 1640 (amide C=O) The FT-IR chart is shown in Figure 2.

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

[0115] <Synthesis of Compound 3>

[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, １ , N ４0.28 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 3.

[0117] FT-IR: wave number (cm －１ ) = 3340 (amine N-H), 3100-3000 (aromatic C-H), 1720 (ester C=O), 1640 (amide C=O). The FT-IR chart is shown in FIG.

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

[0119] The obtained compounds were subjected to heat resistance temperature measurement by thermogravimetry and light absorption measurement in the ultraviolet region. Furthermore, the heat resistance of dried films of compositions containing the obtained compounds was evaluated. For comparison, the following compounds 4 and 5 were also evaluated in the same manner in some tests. Compound 4: Solvent Blue 11 Compound 5: Pigment Blue 15:3

[0120] (Heat Resistance Temperature) Using a thermogravimetric analyzer (manufactured by Waters, device name: TGA5500), the onset temperature of each compound was measured by thermogravimetry and used as the heat resistance temperature. The amount of sample used per measurement was 1 to 2 mg. The measurement was carried out in a nitrogen atmosphere by increasing the temperature from 50°C to 600°C at a rate of 10°C per minute. The results are shown in Table 1.

[0121]

[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] (Absorbance and Heat Resistance of Dried Film) 30 g of φ0.3 mm zirconia beads were added to a mixture of 1 g each of Compound 1, Compound 2, Compound 4, and Compound 5 and 19 g of dipropylene glycol monomethyl ether, and the mixture was dispersed for 2 hours using a rocking mill. 3 g of this dispersion was added to 10 g of resin (Cyclomer P (ACA) Z320, manufactured by Daicel Chemical Industries, Ltd.) to prepare a solution. The resulting solution was applied to a glass plate using an applicator with a 60 μm gap and prebaked at 90°C for 30 minutes in a circulating drying oven to obtain a dried film. The absorbance of the resulting dried film was measured using a JASCO V-570 equipped with an integrating sphere. As shown in Figure 4, the dried films of Compound 1 and Compound 2 exhibited significantly reduced light absorption in the UV region compared to the dried film of Compound 5. The sample was then placed in a reflow tester (NIS-20-82C). The test conditions were 260°C in an air atmosphere, and the treatment was performed three times. The film before and after the treatment was measured for data in the L*a*b* color system using a CM-5 manufactured by Konica Minolta, and ΔE*ab was calculated using the following formula: ΔE*ab=[(ΔL*) ２ +(Δa*) ２ +(Δb*) ２ 〕 １／２ The results are shown in Table 2.

[0124]

[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 FIG. 5.

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

[0128] The anthraquinone compound of the present invention has excellent heat resistance, and light absorption in the ultraviolet region (particularly, a wavelength of 365 nm) is suppressed. Due to these properties, the coloring composition of the present invention can be suitably used as a curable composition. 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): In formula (1), X １ and X ２ are each independently —O—, —NH—, or —S—, and 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, and 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, where R ｓ are each independently 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 may be 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 -, -NHC(=O)- and -C(=O)NH-, R １ and R ２ are each independently a hydrogen atom, —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=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 may be substituted; R ３ are each independently —OH, —OR ａ , -SR ａ , -NR ｂ R ｃ , -NR ｂ C(=O)R 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 , -OS(=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 of 1 to 9; q is an integer of 1 to 9; r is an integer of 0 to 4; R ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, or a monovalent aromatic ring 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 ring 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 ring 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 ring group, which may be substituted; M ａ is sodium or potassium, and with the proviso that 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). 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 , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a monovalent hydrocarbon group having 1 to 30 carbon atoms, 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)X ｅ , -C(=O)OX ｅ , -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 bonded 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 is a linking group selected from -, -NHC(=O)- and -C(=O)NH-, s is an integer of 0 to 3, t is an integer of 0 to 4, u is an integer of 0 to 3, v is an integer of 0 to 2, X ａ represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or a monovalent aromatic ring 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 ring 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 ring 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 ring group, which may be substituted; X ｅ 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; M ｂ is sodium or potassium, and * is a bond.

2. The anthraquinone compound according to claim 1, wherein formula (1) has at least two groups 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).

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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