Anthraquinone compounds, colored compositions, and cured products

Abstract

This invention provides novel anthraquinone compounds. They are anthraquinone compounds represented by formula (1).

Description

Technical Field

[0001] This invention relates to novel anthraquinone compounds, coloring compositions containing the anthraquinone compounds, and cured products of the coloring compositions. Background Technology

[0002] Color filters are found in optical filters primarily used in liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs), and the like. Color filters typically use the three primary colors of RGB, but it's difficult to achieve pure RGB hues using only a single color material. Therefore, efforts have been made to blend multiple color materials to approximate the desired RGB hues. Additionally, attempts have also been made to blend multiple color materials in solder resists for printed circuit boards to obtain the desired hues.

[0003] Among the color materials used in color filters and solder resists, Pigment Blue 15, a copper phthalocyanine pigment, is known as a colorant. Furthermore, a coloring photosensitive resin composition capable of forming a high-brightness color filter using copper phthalocyanine has been proposed (Patent Document 1).

[0004] In addition, Solvent Blue 11 and other anthraquinone dyes are known, and photosensitive resins with excellent sensitivity, storage stability after lamination onto a substrate, and hue stability using specific anthraquinone compounds have been proposed (Patent Document 2).

[0005] Existing technical documents

[0006] Patent documents

[0007] Patent Document 1: Japanese Patent Application Publication No. 2019-152852

[0008] Patent Document 2: Japanese Patent Application Publication No. 2013-57902 Summary of the Invention

[0009] The problem the invention aims to solve

[0010] While copper phthalocyanine pigments exhibit good heat resistance, they suffer from significant light absorption in the ultraviolet region (especially at a wavelength of 365 nm). On the other hand, anthraquinone dyes exhibit poor heat resistance.

[0011] Under such circumstances, there is a need for novel compounds that can function as colorants. The object of this invention is to provide a novel compound, a coloring composition containing the compound, and a cured product of the coloring composition.

[0012] Solution for solving the problem

[0013] The inventors conducted repeated research and found that anthraquinone compounds with specific structures can provide excellent heat resistance and suppress the absorption of light in the ultraviolet region (especially at a wavelength of 365 nm), thus completing this invention.

[0014] The main points of this invention are as follows.

[0015] [1] An anthraquinone compound represented by the following formula (1).

[0016]

[0017] In equation (1),

[0018] X1 and X2 are each independently -O-, -NH-, or -S-.

[0019] Y1 is an alkyl, phenyl, or R group with 1 to 6 carbon atoms. s -R t -R s The derived (p+1) valence residues, wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y1 is a single bond.

[0020] Y2 is an alkyl, phenyl, or R group with 1 to 6 carbon atoms. s -R t -R s The derived (q+1) valence residues, wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group are each optionally substituted, or Y2 is a single bond.

[0021] Here, R s Each of the above-mentioned alkyl, phenyl, or aralkyl groups having 1 to 6 carbon atoms may be optionally substituted.

[0022] R t The group is selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0023] R1 and R2 are each independently hydrogen atoms, selected from -OH and -OR. a -SR a -NR b R c -NR b -C(=O)R d -C(=O)NR b R cHalogen 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 groups in the formula (2), (3), (4), and (5) are: a monovalent hydrocarbon group with 1 to 30 carbon atoms, a group shown in formula (2), a group shown in formula (3), a group shown in formula (4), and a group shown in formula (5), wherein the monovalent hydrocarbon group with 1 to 30 carbon atoms may be optionally substituted.

[0024] R3 is independently selected from -OH, -OR a -SR a -NR b R c -NR b -C(=O)R 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 And groups in monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein the aforementioned monovalent hydrocarbon groups having 1 to 30 carbon atoms may optionally be substituted.

[0025] p is an integer from 1 to 9.

[0026] q is an integer from 1 to 9.

[0027] r is an integer between 0 and 4.

[0028] R a It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0029] R b It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0030] R c It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0031] R dIt is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0032] M a Sodium or potassium,

[0033] in,

[0034] Formula (1) has at least one group selected from the group shown in Formula (2), the group shown in Formula (3), the group shown in Formula (4), and the group shown in Formula (5).

[0035]

[0036] In equations (2) to (5),

[0037] R5 and R6 are each independently selected from -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 groups in monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein adjacent groups may optionally be linked together to form a ring, and the aforementioned monovalent hydrocarbon groups having 1 to 30 carbon atoms may optionally be substituted.

[0038] R7 is independently a hydrogen atom, -C(=O)X e -C(=O)OX e -C(=O)OM b Alkyl, aralkyl, or monovalent aromatic cyclic groups may be substituted, and the two R7 groups may be optionally linked together to form a ring.

[0039] L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0040] s is an integer between 0 and 3.

[0041] t is an integer between 0 and 4.

[0042] u is an integer between 0 and 3.

[0043] v is an integer between 0 and 2.

[0044] X a It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0045] X b It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0046] X c It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0047] X d It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0048] X e It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0049] M b Sodium or potassium,

[0050] For connection keys.

[0051] [2] The anthraquinone compound according to [1], wherein formula (1) has at least two groups selected from the groups shown in formula (2), formula (3), formula (4) and formula (5).

[0052] [3] The anthraquinone compound according to [2], wherein formula (1) has at least one R1 as a group selected from the group shown in formula (2), the group shown in formula (3), the group shown in formula (4) and the group shown in formula (5), and has at least one R2 as a group selected from the group shown in formula (2), the group shown in formula (3), the group shown in formula (4) and the group shown in formula (5).

[0053] [4] A coloring composition containing any one of the anthraquinone compounds in [1] to [3].

[0054] [5] The coloring composition according to [4] also contains coloring materials other than the anthraquinone compounds described in [1].

[0055] [6] The coloring composition according to [4] is a photosensitive coloring composition.

[0056] [7] The coloring composition according to [5] is a photosensitive coloring composition.

[0057] [8] A cured product, which is a cured product of the coloring composition of any one of [4] to [7].

[0058] The effects of the invention

[0059] According to the present invention, novel anthraquinone compounds, coloring compositions containing the anthraquinone compounds, and cured products of the coloring compositions are provided. The anthraquinone compounds of the present invention exhibit excellent heat resistance and, in addition, suppress light absorption in the ultraviolet region (particularly at wavelength 365 nm). Based on these properties, the coloring compositions of the present invention are suitable for use as curable compositions, and are particularly suitable for photosensitive coloring compositions. Attached Figure Description

[0060] Figure 1 The image shows the FT-IR spectrum of compound 1 from the example.

[0061] Figure 2 The image shows the FT-IR spectrum of compound 2 from the example.

[0062] Figure 3 The image shows the FT-IR spectrum of compound 3 from the example.

[0063] Figure 4 The graph shows the absorbance of the dried films of compounds 1, 2, 4 and 5 in the examples.

[0064] Figure 5 The graph shows the UV-Vis absorption spectra of compounds 1, 2 and 4 in solution as examples. Detailed Implementation

[0065] The present invention will now be described in detail.

[0066] Terminology

[0067] In this specification, alkyl groups can be branched or straight-chain. Examples of alkyl groups with 1 to 20 carbon atoms are given, with 1 to 8 carbon atoms being preferred. Specifically, examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, n-pentyl, n-hexyl, cyclohexyl, and 2-ethylhexyl.

[0068] Alkenes can be branched or linear. Examples of alkenes with 2 to 20 carbon atoms are given, with 2 to 8 carbon atoms being preferred. Specifically, examples include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, butadienyl, pentenyl, pentadienyl, hexadienyl, etc.

[0069] The alkynyl group can be branched or straight-chain. Examples of alkynyl groups with 2 to 20 carbon atoms are given, with 2 to 8 carbon atoms being preferred. Specifically, examples include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, butyynyl, pentynyl, pentyynyl, and 1-hexynyl.

[0070] Aryl groups are groups formed by replacing one hydrogen atom of an alkyl group with an aryl group. Examples of aryl groups with 7 to 30 carbon atoms include benzyl, methylbenzyl, 1-phenylethyl, and naphthylmethyl.

[0071] Alkylene, alkenylene, and ynylene are divalent groups obtained by removing a hydrogen atom from an alkyl, alkenyl, or ynyl group.

[0072] A arylene group is a divalent group formed by removing one hydrogen atom from the aromatic ring of an aralkyl group.

[0073] There are no special restrictions on hydrocarbon groups as long as they have one or more carbon atoms, including alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, aralkyl, etc.

[0074] When the above groups are substituted, examples of substituents include hydroxyl, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted amide, halogen atom (fluorine, chlorine, bromine, iodine), cyano, nitro, carboxyl (which can be in salt form), carboxylic acid ester residue, sulfonic acid (which can be in salt form), sulfonate residue, and hydrocarbon group. The hydrocarbon group as a substituent can be replaced by any substituent, or interrupted by heteroatoms (oxygen, nitrogen, sulfur, etc.) or bonds (ester bonds, amide bonds, etc.).

[0075] Rings include carbon rings and heterocycles. There are no particular limitations on the carbon ring, as long as all cyclic atoms are carbon atoms; examples include 4- to 20-membered rings, preferably 4- to 14-membered rings. The carbon ring can be aromatic or non-aromatic, and can be monocyclic or polycyclic. Examples include cycloalkanes (such as cyclopropane, cyclopentane, cyclohexane, etc.) and aromatic hydrocarbons (such as benzene, naphthalene, etc.). The carbon ring can contain the aforementioned substituents and hydrocarbon groups.

[0076] Heterocyclic rings are not particularly limited as long as the cyclic atoms are carbon atoms or heteroatoms; examples include 4- to 20-membered rings, preferably 4- to 14-membered rings. Examples of heteroatoms include nitrogen, oxygen, and sulfur atoms. Heterocyclic rings can be aromatic or non-aromatic, and can be monocyclic or polycyclic. Examples include pyridine rings, lactone rings, imidazole rings, thiazole rings, and oxazole rings. Heterocyclic rings can contain the aforementioned substituents and hydrocarbon groups.

[0077] Aromatic rings can be carbon rings or heterocycles, including examples of the aromatics mentioned above.

[0078] <Anthraquinone substituents>

[0079] The anthraquinone compounds of the present invention are characterized in that they have at least one substituent having an anthraquinone structure (hereinafter also referred to as an anthraquinone substituent).

[0080] Anthraquinone substituents are represented by formulas (2) to (5).

[0081]

[0082] In equations (2) to (5),

[0083] R5 and R6 are each independently selected from -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 groups in a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups are optionally linked together to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted.

[0084] R7 is independently a hydrogen atom, -C(=O)X e -C(=O)OX e -C(=O)OM b Alkyl, aralkyl, or monovalent aromatic cyclic groups may be substituted, and the two R7 groups may be optionally linked together to form a ring.

[0085] L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0086] s is an integer between 0 and 3.

[0087] t is an integer between 0 and 4.

[0088] u is an integer between 0 and 3.

[0089] v is an integer between 0 and 2.

[0090] X a It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0091] X b It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0092] X c It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0093] X d It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0094] X e It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0095] M b Sodium or potassium,

[0096] For connection keys.

[0097] In equation (2), L is preferably bonded to the α-position (5, 8-position) of the anthraquinone structure.

[0098] In equation (3), L is preferably bonded to the β position (2, 3 positions) of the anthraquinone structure. Here, the position of the -N(R7)2 bond in the anthraquinone structure is set to the 1 position.

[0099] In equation (2), L is preferably -O-.

[0100] In equation (3), L is preferably -O- or -S-.

[0101] In equation (4), L is preferably a single bond.

[0102] In equation (5), L is preferably a single bond.

[0103] In equation (2), s is preferably 0 or 1, and u is preferably 0 or 1.

[0104] In equation (3), t is preferably 0 or 1, and v is preferably 0 or 1.

[0105] In equation (4), t is preferably 0 or 1, and u is preferably 0 or 1.

[0106] In equation (5), t is preferably 0 or 1, and v is preferably 0 or 1.

[0107] In equations (2) to (5), when R5 and / or R6 exist, they are preferably each independently -NX. b X c -OH, -OX a or -SX a .

[0108] In formulas (2) to (4), R7 is preferably a hydrogen atom, an alkyl group or a monovalent aromatic cyclic group, and more preferably a hydrogen atom or an alkyl group.

[0109] Examples of anthraquinone substituents in formula (2) include groups represented by formulas (2-1) to (2-4). Formulas (2-1) and (2-4) are preferred.

[0110]

[0111] In equations (2-1) to (2-4),

[0112] For connection key,

[0113] L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0114] Z1~Z4 and Z5~Z7 are each independently hydrogen atoms, selected from -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 groups in monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein adjacent groups may optionally be linked together to form a ring, and the aforementioned monovalent hydrocarbon groups having 1 to 30 carbon atoms may optionally be substituted.

[0115] R7 is independently a hydrogen atom, -C(=O)X e -C(=O)OX e-C(=O)OM b Alkyl, aralkyl, or monovalent aromatic cyclic groups may be substituted.

[0116] L is preferably -O-.

[0117] Z1~Z4 are preferably each independently composed of hydrogen atoms, -NX b X c -OH or -OX a .

[0118] Z5~Z7 are preferably each independently composed of hydrogen atoms, -NX b X c -OH or -OX a .

[0119] R7 is preferably an independent hydrogen atom, alkyl group, or monovalent aromatic cyclic group.

[0120] Examples of anthraquinone substituents in formula (3) include formulas (3-1) to (3-3). Formulas (3-2) and (3-3) are preferred.

[0121]

[0122] In equations (3-1) to (3-3),

[0123] For connection key,

[0124] L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0125] Z1~Z4 and Z5~Z7 are each independently hydrogen atoms, -OH, and -OX atoms. 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 -SO3Mb And groups in a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups are optionally linked together to form a ring, and the monovalent hydrocarbon group having 1 to 30 carbon atoms is optionally substituted.

[0126] R7 is independently a hydrogen atom, -C(=O)X e -C(=O)OX e -C(=O)OM b Alkyl, aralkyl, or monovalent aromatic cyclic groups may be substituted.

[0127] L is preferably -O- or -S-.

[0128] Z1~Z4 are preferably each independently composed of hydrogen atoms, -NX b X c -OH or -OX a .

[0129] Z5~Z7 are preferably each independently composed of hydrogen atoms, -NX b X c -OH or -OX a .

[0130] R7 is preferably an independent hydrogen atom, alkyl group, or monovalent aromatic cyclic group.

[0131] The anthraquinone substituents in formula (4) can be rewritten as in formula (4-1).

[0132]

[0133] In equation (4-1),

[0134] For connection key,

[0135] L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0136] Z1~Z4 and Z5~Z7 are each independently hydrogen atoms, selected from -OH, -OX. a -SX a -NX b X c -NX b C(=O)X d -C(=O)NX b X cHalogen 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 groups in monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein adjacent groups may optionally be linked together to form a ring, and the aforementioned monovalent hydrocarbon groups having 1 to 30 carbon atoms may optionally be substituted.

[0137] R7 is independently a hydrogen atom, -C(=O)X e -C(=O)OX e -C(=O)OM b Alkyl, aralkyl, or monovalent aromatic cyclic groups may be substituted.

[0138] L is preferred for single bonds.

[0139] Z1~Z4 are preferably each independently composed of hydrogen atoms, -NX b X c -OH or -OX a .

[0140] Z5~Z7 are preferably each independently composed of hydrogen atoms, -NX b X c -OH, -OX a or -SX a .

[0141] R7 is preferably a hydrogen atom or an alkyl group.

[0142] The anthraquinone substituents in formula (5) can be rewritten as in formula (5-1).

[0143]

[0144] In equation (5-1),

[0145] For connection key,

[0146] L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0147] Z1~Z4, Z5 and Z8 are each independently hydrogen atoms, selected from -OH, -OX. a -SXa -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 groups in monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein adjacent groups may optionally be linked together to form a ring, and the aforementioned monovalent hydrocarbon groups having 1 to 30 carbon atoms may optionally be substituted.

[0148] L is preferred for single bonds.

[0149] Z1~Z4 are preferably each independently composed of hydrogen atoms, -NX b X c -OH or -OX a .

[0150] Z5 and Z8 are preferably each independently composed of hydrogen atoms, -NX b X c -OH, -OX a or -SX a .

[0151] Anthraquinone compounds

[0152] The anthraquinone compounds of the present invention are represented by formula (1), wherein R1 and R2 have at least one anthraquinone substituent represented by any one of formulas (2) to (5).

[0153]

[0154] In equation (1),

[0155] X1 and X2 are each independently -O-, -NH-, or -S-.

[0156] Y1 is an alkyl, phenyl, or R group with 1 to 6 carbon atoms. s -R t -R s The derived (p+1) valence residues, wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group may be optionally substituted, or Y1 may be a single bond.

[0157] Y2 is an alkyl, phenyl, or R group with 1 to 6 carbon atoms. s -Rt -R s The derived (q+1) valence residues, wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group may be optionally substituted, or Y2 may be a single bond.

[0158] Among them, R s Each of the above-mentioned alkyl, phenyl, or aralkyl groups having 1 to 6 carbon atoms may be optionally substituted.

[0159] R t The group is selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-.

[0160] R1 and R2 are independently hydrogen atoms, -OH, and -OR, respectively. a -SR a -NR b R c -NR b C(=O)R 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 groups in the formula (2), (3), (4), and (5) are: a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group shown in formula (2), a group shown in formula (3), a group shown in formula (4), and a group shown in formula (5), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted.

[0161] R3 is independently selected from -OH, -OR a -SR a -NR b R c -NR b C(=O)R 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 And groups in monovalent hydrocarbon groups having 1 to 30 carbon atoms, wherein the aforementioned monovalent hydrocarbon groups having 1 to 30 carbon atoms may optionally be substituted.

[0162] p is an integer from 1 to 9.

[0163] q is an integer from 1 to 9.

[0164] r is an integer between 0 and 4.

[0165] R a It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0166] R b It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0167] R c It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted.

[0168] R d It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted.

[0169] M a Sodium or potassium,

[0170] in,

[0171] Formula (1) has at least one group selected from the group shown in Formula (2), the group shown in Formula (3), the group shown in Formula (4), and the group shown in Formula (5).

[0172] The anthraquinone compounds of the present invention are shown in formula (1). They have rigid structures such as aromatic amide structure, aromatic ester structure, and aromatic thioester structure. Therefore, it is speculated that they maintain the excellent properties of anthraquinone compounds as colorants while also having excellent heat resistance.

[0173] Formula (1) preferably has at least two anthraquinone substituents represented by any of formulas (2) to (5), more preferably has at least one R1 as an anthraquinone substituent and at least one R2 as an anthraquinone substituent, and particularly preferably has one R1 as an anthraquinone substituent and one R2 as an anthraquinone substituent.

[0174] R1 and R2, other than the anthraquinone substituents, are preferably hydrogen atoms.

[0175] In the anthraquinone compounds of the present invention, X1 and X2 are preferably -O- or -NH-, more preferably both X1 and X2 are -O-, or both X1 and X2 are -NH-.

[0176] In the anthraquinone compounds of the present invention, Y1 is an alkyl, phenyl, or compound with 1 to 6 carbon atoms. s -R t -R s The derived (p+1) valence residues, wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group having 1 to 6 carbon atoms are optionally substituted, or Y1 is a single bond.

[0177] Additionally, Y2 is composed of alkyl, phenyl, or R groups having 1 to 6 carbon atoms. s -R t -R s The derived (q+1) valence residues, wherein the alkyl group having 1 to 6 carbon atoms and the phenyl group having 1 to 6 carbon atoms are optionally substituted, or Y2 is a single bond.

[0178] Here, p is an integer from 1 to 9, and q is an integer from 1 to 9.

[0179] When p or q is 1, Y1 and Y2 are composed of alkylene, phenylene (1,4-phenylene, 1,3-phenylene, etc.) or R atoms having 1 to 6 carbon atoms. s -R t -R s When the derived divalent residues have p or q of 2 to 9, they are alkyl, phenyl, or R groups with 1 to 6 carbon atoms. s -R t -R s It removes 2 to 9 hydrogen atoms from residues with 3 to 10 valences.

[0180] In R s -R t -R s In the middle, R s At least one of them is preferably phenyl, R t Preferably, it is -C(=O)O-, -OC(=O)-, -C(=O)NH-, or -NHC(=O)-. Particularly preferred is R. s All are phenyl groups, and Rt is -C(=O)O-, -OC(=O)-, -C(=O)NH- or -NHC(=O).

[0181] Y1 and Y2 can be single bonds. When Y1 is a single bond, p is preferably 1 and R1 is a hydrogen atom. When X1 is -O-, the terminal group is a carboxyl group. When Y2 is a single bond, q is preferably 1 and R2 is a hydrogen atom. When X2 is -O-, the terminal group is a carboxyl group.

[0182] Formula (1) has at least one anthraquinone substituent as shown in any of Formulas (2) to (5).

[0183] r is preferably 0 or 1, more preferably 0.

[0184] Examples of compounds of formula (1) include those 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. Formula (1-1β) is a compound in which X1 and X2 are -NH- and Y1 and Y2 are phenylene. Formula (1-1γ) is a compound in which either X1 or X2 is -O-, the other is -NH-, and Y1 and Y2 are phenylene.

[0185]

[0186] In equations (1-1α), (1-1β), and (1-1γ),

[0187] Z 10 ~Z 19 Each is independently a hydrogen atom, -OH, or -OR. a -SR a -NR b R c -NR b -C(=O)R 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 group consisting of 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), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, wherein Z 10 ~Z 19 At least one of them is a group represented by any of the formulas (2) to (5).

[0188] Regarding Z 10 ~Z 19 In addition to any of the groups shown in formulas (2) to (5), hydrogen atoms, alkyl groups, halogen atoms are preferred, and hydrogen atoms are more preferred.

[0189] Z 10 ~Z 19 One or two of them are preferably any of the groups shown in formulas (2) to (5).

[0190] Z 10 ~Z 19 When two of the groups in Z are any of the groups shown in formulas (2) to (5), 10 ~Z 14 One of them is any of the groups shown in formulas (2) to (5), Z 15 ~Z 19 One of them can be any of the groups shown in formulas (2) to (5), preferably Z. 10 ~Z 19 Z in 12 and Z 17 either or both of them, Z 11 and Z 16 either or both of them, or Z 13 and Z 18 Any one or both of them are groups represented by any of the formulas (2) to (5).

[0191] Except for any of the groups shown in formulas (2) to (5), hydrogen atoms, -OH, -OR a -SR a -NR b R c -NR b C(=O)R 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, wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, preferably a hydrogen atom, an alkyl group, or a halogen atom, and more preferably a hydrogen atom.

[0192] Examples of compounds of formula (1) include those represented by formulas (1-2α), (1-2β), and (1-2γ). Formula (1-2α) is where X1 and X2 are -O- and Y1 and Y2 are R-. s -R t -R s The compound, of formula (1-2β), has X1 and X2 as -NH- and Y1 and Y2 as R-. s -R t -R s The compound of formula (1-2γ) is such that either X1 or X2 is -O-, the other is -NH-, and Y1 and Y2 are R-.s -R t -R s Compounds.

[0193]

[0194] In equations (1-2α), (1-2β), and (1-2γ),

[0195] Z 10 ~Z 19 Z 20 ~Z 21 Z 23 ~Z 26 and Z 28 ~Z 29 Each is independently a hydrogen atom, -OH, or -OR. a -SR a -NR b R c -NR b -C(=O)R 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 group consisting of 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), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, wherein Z 10 ~Z 29 At least one of them is a group represented by any of the formulas (2) to (5).

[0196] Z t Each is independently selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -S(=O)2NH-, -NHS(=O)2-, -NHC(=O)- and -C(=O)NH-.

[0197] Regarding Z 10 ~Z 19 Z 20 ~Z 21 Z 23 ~Z 26 Z 28 ~Z29 In addition to any of the groups shown in formulas (2) to (5), hydrogen atoms, alkyl groups, halogen atoms are preferred, and hydrogen atoms are more preferred.

[0198] Z 10 ~Z 19 Z 20 ~Z 21 Z 23 ~Z 26 Z 28 ~Z 29 One or two of the groups are preferably represented by any one of formulas (2) to (5), Z 10 ~Z 19 One or two of them are preferably any of the groups shown in formulas (2) to (5).

[0199] Z 10 ~Z 19 Z 20 ~Z 21 Z 23 ~Z 26 Z 28 ~Z 29 If one or two of them are any of the groups shown in (2) to (5), then Z 10 ~Z 14 One of them is any of the groups shown in formulas (2) to (5), Z 15 ~Z 19 One of them can be any of the groups shown in formulas (2) to (5), preferably Z. 10 ~Z 19 Z in 12 and Z 17 either or both of them, Z 11 and Z 16 either or both of them, or Z 13 and Z 18 Any one or both of them are groups represented by any of the formulas (2) to (5).

[0200] Except for any of the groups shown in formulas (2) to (5), hydrogen atoms, -OH, -OR a -SR a -NR b R c -NR b C(=O)R 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, wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, preferably a hydrogen atom, an alkyl group, or a halogen atom, and more preferably a hydrogen atom.

[0201] Examples of compounds of formula (1) include those represented by formulas (1-3α), (1-3β), (1-3γ), and (1-3δ). Formula (1-3α) is where X1 and X2 are -O-, one of Y1 and Y2 is phenylene, and the other is R-. s -R t -R s The compound, of formula (1-2β), has X1 and X2 as -NH-, one of Y1 and Y2 as phenylene, and the other as R. s -R t -R s Compounds of formula (1-3γ) and (1-3δ) wherein either X1 or X2 is -O- and the other is -NH-, and either Y1 or Y2 is phenylene and the other is R- s -R t -R s Compounds.

[0202]

[0203] In equations (1-3α), (1-3β), (1-3γ), and (1-3δ),

[0204] Z 10 ~Z 19 Z 20 ~Z 21 and Z 23 ~Z 24 Each is independently a hydrogen atom, -OH, or -OR. a -SR a -NR b R c -NR b -C(=O)R 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 group consisting of 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), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, wherein Z 10 ~Z 24 At least one of them is a group represented by any of the formulas (2) to (5).

[0205] Z t Each is independently selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -S(=O)2NH-, -NHS(=O)2-, -NHC(=O)- and -C(=O)NH-.

[0206] Regarding Z 10 ~Z 19 Z 20 ~Z 21 and Z 23 ~Z 24 In addition to any of the groups shown in formulas (2) to (5), hydrogen atoms, alkyl groups, halogen atoms are preferred, and hydrogen atoms are more preferred.

[0207] Z 10 ~Z 19 Z 20 ~Z 21 and Z 23 ~Z 24 One or two of the groups are preferably any of the groups shown in formulas (2) to (5), Z 10 ~Z 19 One or two of them are preferably any of the groups shown in formulas (2) to (5).

[0208] Z 10 ~Z 19 Z 20 ~Z 21 and Z 23 ~Z 24 If one or two of them are any of the groups shown in (2) to (5), then Z 10 ~Z 14 One of them is any of the groups shown in formulas (2) to (5), Z 15 ~Z 19 One of them can be any of the groups shown in formulas (2) to (5), preferably Z. 10 ~Z 19 Z in 12 and Z 17 either or both of them, Z 11 and Z16 either or both of them, or Z 13 and Z 18 Any one or both of them are groups represented by any of the formulas (2) to (5).

[0209] Except for any of the groups shown in formulas (2) to (5), hydrogen atoms, -OH, -OR a -SR a -NR b R c -NR b -C(=O)R 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, wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, preferably a hydrogen atom, an alkyl group, or a halogen atom, and more preferably a hydrogen atom.

[0210] Examples of compounds of formula (1) include those 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 phenylene, 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 phenylene, and the other is a single bond; formulas (1-4γ) and (1-4δ) are compounds in which either X1 or X2 is -O-, the other is -NH-, and one of Y1 and Y2 is phenylene, and the other is a single bond.

[0211]

[0212] In equations (1-4α), (1-4β), (1-4γ), and (1-4δ),

[0213] Z 10 ~Z 14 Each is independently a hydrogen atom, -OH, or -OR. a -SR a -NR b R c -NR b C(=O)R d -C(=O)NR b Rc 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 group consisting of 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), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, wherein Z 10 ~Z 29 At least one of them is a group represented by any of the formulas (2) to (5).

[0214] Z t Each is independently selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -NHC(=O)- and -C(=O)NH-.

[0215] R u It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl or a monovalent aromatic cyclic group, which may be optionally substituted, preferably a hydrogen atom.

[0216] Regarding Z 10 ~Z 14 In addition to any of the groups shown in formulas (2) to (5), hydrogen atoms, alkyl groups, halogen atoms are preferred, and hydrogen atoms are more preferred.

[0217] Z 10 ~Z 14 One of the preferred groups is any one of the groups shown in formulas (2) to (5).

[0218] Z 10 ~Z 14 When one of the groups is any one of those shown in (2) to (5), Z 11 Z 12 or Z 13 The group in the formula is preferably any of the groups shown in formulas (2) to (5).

[0219] In addition to any of the groups shown in formulas (2) to (5), hydrogen atoms, -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 A monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, preferably a hydrogen atom, an alkyl group, or a halogen atom, and more preferably a hydrogen atom.

[0220] Examples of compounds of formula (1) include those represented by formulas (1-5α), (1-5β), (1-5γ), and (1-5δ). Formula (1-5α) is where X1 and X2 are -O- and one of Y1 and Y2 is R. s -R t -R s The other is a compound with a single bond, formula (1-5β) where X1 and X2 are -NH- and one of Y1 and Y2 is R. s -R t -R s The other is a compound with a t-single bond, where formulas (1-5γ) and (1-5δ) are either X1 or X2 -O-, the other -NH-, and one of Y1 or Y2 is R. s -R t -R s The other is a compound with a single bond.

[0221]

[0222] In equations (1-5α), (1-5β), (1-5γ), and (1-5δ),

[0223] Z 10 ~Z 14 Z 20 ~Z 21 and Z 23 ~Z 24 Each is independently a hydrogen atom, -OH, or -OR. a -SR a -NR b R c -NR b C(=O)R 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 group consisting of 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), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, wherein Z 10 ~Z 14 Z 20 ~Z 21 and Z 23 ~Z 24 At least one of them is a group represented by any of the formulas (2) to (5).

[0224] Z t Each is independently selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -OS(=O)2-, -S(=O)2NH-, -NHS(=O)2-, -NHC(=O)- and -C(=O)NH-.

[0225] R u It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl or a monovalent aromatic cyclic group, which may be optionally substituted, preferably a hydrogen atom.

[0226] Regarding Z 10 ~Z 14 Z 20 ~Z 21 and Z 23 ~Z 24 In addition to any of the groups shown in formulas (2) to (5), hydrogen atoms, alkyl groups, halogen atoms are preferred, and hydrogen atoms are more preferred.

[0227] Z 10 ~Z 14 Z 20 ~Z 21 and Z 23 ~Z 24 One of the preferred groups is represented by any one of formulas (2) to (5), Z 10 ~Z 14 One of them is more preferably any of the groups shown in formulas (2) to (5).

[0228] Z 10 ~Z 14 Z 20 ~Z 21 and Z 23 ~Z24 When one of the groups is any of the groups shown in formulas (2) to (5), Z 10 ~Z 14 One of the preferred groups is represented by any one of formulas (2) to (5), Z 11 Z 12 or Z 13 More preferably, any of the groups in formulas (2) to (5) are the groups shown.

[0229] Except for any of the groups shown in formulas (2) to (5), hydrogen atoms, -OH, -OR a -SR a -NR b R c -NR b -C(=O)R 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, wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted, preferably a hydrogen atom, an alkyl group, or a halogen atom, and more preferably a hydrogen atom.

[0230] As specific examples of equation (1), the following can be listed.

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262] <Manufacturing Method>

[0263] The anthraquinone compounds 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.

[0264] Examples of hydroxyl compounds having anthraquinone substituents include compounds shown in formulas (2A), (3A), (4A), and (5A), and examples of amino compounds having anthraquinone substituents include compounds shown in formulas (2B), (3B), (4B), and (5B).

[0265]

[0266]

[0267] In equations (2A), (2B), (3A), (3B), (4A), (4B), (5A), and (5B),

[0268] R5, R6, R7, R8, L, s, t, u, and v have the same meaning as in equations (2) to (5).

[0269] Y has the same meaning as Y1 or Y2 in formula (1). The compounds shown in formulas (2A), (2B), (3A), (3B), (4A), (4B), (5A) and (5B) can be conventionally known compounds.

[0270] In addition, the compound shown in (5A) can also be obtained by the method described in Japanese Patent Application Publication No. 2013-217964, and the compound shown in (5B) can also be obtained by the method described in US Patent No. 2,701,802.

[0271] By reacting a hydroxyl compound with an anthraquinone substituent with terephthalic acid or a derivative thereof, a compound in formula (1) where X1 or X2 is -O- can be obtained. By reacting an amino compound with an anthraquinone substituent with terephthalic acid or a derivative thereof, a compound in formula (1) where X1 or X2 is -NH- can be obtained.

[0272] The amount of an amino compound having an anthraquinone substituent or a hydroxy compound having an anthraquinone substituent with terephthalic acid or a derivative thereof may be set as an excess of the amount of the amino compound or hydroxy compound relative to the amount of terephthalic acid or a derivative thereof.

[0273] The reaction temperature can be set to 0~120℃, preferably 10~80℃. The reaction time can be set to 0.1~40 hours, more preferably 0.5~10 hours. The reaction can be carried out under a nitrogen atmosphere.

[0274] The reaction can be carried out using a dehydrating condensing agent. There are no particular limitations on the dehydrating condensing agent; examples 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.

[0275] Furthermore, additives such as 1-hydroxybenzotriazole and N,N-dimethylaminopyridine can be used.

[0276] The reaction is preferably carried out in a solvent. Examples of solvents 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 these, amide solvents are preferred.

[0277] After the reaction, the product can be post-processed and purified as needed to separate the target compound. Examples of post-processing include filtration, washing, extraction, vacuum concentration, recrystallization, distillation, and column chromatography.

[0278] As a specific example of this method, the following scheme can be cited.

[0279]

[0280] As another method, the anthraquinone compounds of the present invention can react carboxylic acid compounds having anthraquinone substituents with compounds or derivatives thereof shown in formula (6A) or (6B).

[0281]

[0282] The compound of formula (6A) can be synthesized, for example, by the method described in Japanese Patent No. 5330013.

[0283] The compound of formula (6B) is known to be synthesized by the following reaction.

[0284]

[0285] The compound of formula (6B) can also be synthesized by hydrolysis of polyethylene terephthalate (PET), for example by the method described in Polymer Chemistry (2013), 4(5), 1610-1616.

[0286] Examples of carboxylic acid compounds with anthraquinone substituents include compounds shown in formulas (2C), (3C), and (4C).

[0287]

[0288] In equations (2C), (3C), (4C), and (5C),

[0289] R5, R6, R7, R8, L, s, t, u, and v have the same meaning as in equations (2) to (5).

[0290] Y has the same meaning as Y1 or Y2 in equation (1).

[0291] The amount of carboxylic acid compounds having an anthraquinone substituent and compounds or derivatives thereof shown in formula (6A) or (6B) can be set as an excess of the amount of carboxylic acid compound relative to the amount of compounds or derivatives thereof shown in formula (6A) or (6B).

[0292] The reaction temperature can be set to 80℃~150℃, preferably 90℃~110℃. The reaction time can be set to 1 hour~24 hours, more preferably 12~20 hours. The reaction can be carried out under a nitrogen atmosphere.

[0293] The reaction can be carried out using a dehydrating condensing agent. Alternatively, the reaction can be carried out in a solvent. The dehydrating condensing agent and solvent can be any substances listed in the methods described above.

[0294] After the reaction, the resulting product can be post-processed and purified as needed. These processes can be performed using the methods listed above.

[0295] As a specific example of this method, the following scheme can be cited.

[0296]

[0297] In the anthraquinone compounds of the present invention, compounds in which X1 and X2 are -S- can also be synthesized in the same manner as described above. For example, compounds in which X1 and X2 are -S- can be obtained by using thiols having anthraquinone substituents.

[0298] In the anthraquinone compounds of the present invention, by changing the equivalence ratio of the compound having anthraquinone substituents to the compound or its derivatives shown in formula (6A) or (6B), anthraquinone compounds of the present invention with different numbers of anthraquinone substituents can be produced. For example, by using a compound having 2 or more anthraquinone substituents, the anthraquinone compound of the present invention having 2 anthraquinone substituents as described above can be obtained, and by using an anthraquinone compound having 1 or less anthraquinone substituents, the anthraquinone compound of the present invention having 1 anthraquinone substituent can be obtained.

[0299] As another method, the anthraquinone compound of the present invention having an anthraquinone substituent as shown in formula (5) can also be obtained by reacting anthraquinone-2,3-dicarboxylic anhydride or its derivative with N,N'-bis(4-aminophenyl)terephthalamide, bis(4-aminophenyl)terephthalate, etc. to obtain an amide acid compound, and then imidizing the amide acid compound.

[0300] Amide acid compounds can be obtained by mixing and stirring anthraquinone-2,3-dicarboxylic anhydride or its derivatives with N,N'-bis(4-aminophenyl)terephthalamide, bis(4-aminophenyl)terephthalate, etc., in the solvents described above. The reaction temperature can be set to 0~100℃, and the reaction time can be set to 1~40 hours. Imidination can be carried out using chemical imidization or thermal imidization methods, under conventionally known reaction conditions.

[0301] <Coloring Compositions and Cured Products>

[0302] The anthraquinone compounds of the present invention can be used in the manufacture of various coatings, water-based or oil-based inks, etc. Furthermore, they are also useful as functional pigments such as recording materials. In particular, the anthraquinone compounds of the present invention are insoluble in solvents such as acetone, alcohols, and water, and therefore can be used as pigments.

[0303] The present invention also relates to coloring compositions containing the anthraquinone compounds of the present invention. The coloring compositions contain only the anthraquinone compounds of the present invention or two or more in any ratio.

[0304] The coloring composition may contain coloring materials other than the anthraquinone compounds of the present invention. The coloring materials are not particularly limited, and known pigments and dyes can be used. Examples include:

[0305] CI pigments include red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc.

[0306] CI pigment blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments;

[0307] CI pigments include purple 1, 19, 23, 29, 32, 36, 38, and other purple pigments;

[0308] CI pigments include yellow pigments 24, 93, 108, 110, 120, 138, 147, 185, and 193.

[0309] CI pigments include green pigments such as green 7, 36, 58, and 59.

[0310] Besides CI pigments, examples include compounds classified as having hue, and well-known dyes listed in dyeing guides (for dyeing companies). Additionally, based on chemical structure, examples include azo dyes, anthraquinone dyes, cyanine dyes, phthalocyanine dyes, naphthoquinone dyes, quinone imine dyes, methylene dyes, azomethyl base dyes, squaric acid dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes.

[0311] Coloring materials other than anthraquinone compounds of the present invention may be used in amounts that do not impair the effects of the present invention.

[0312] The coloring composition of the present invention may include a binder resin. The binder resin is not particularly limited, and examples include natural polymers such as gelatin, casein, starch, cellulose derivatives, and alginate; synthetic polymers 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.

[0313] The amount of adhesive resin is not particularly limited; for example, it can be 0.1 to 20 parts by weight relative to 100 parts by weight of the anthraquinone compound of the present invention. The adhesive resin can be a single type or a combination of two or more types in any ratio.

[0314] The coloring composition of the present invention may contain a solvent. The solvent is not particularly limited, but examples include the following solvents.

[0315] Examples include diol 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.

[0316] The coloring compositions of the present invention can be suitably used as curable compositions. For example, a photosensitive coloring composition can be prepared by blending a photosensitive resin and a photopolymerization initiator, etc., into the coloring compositions of the present invention. The anthraquinone compounds of the present invention have suppressed light absorption in the ultraviolet region (especially at a wavelength of 365 nm), and therefore are less likely to affect the photoreaction of the photosensitive coloring composition, and can therefore be preferred. Photosensitive monomers can be further blended into the photosensitive coloring compositions.

[0317] As a photosensitive resin, a resin having an olefinic unsaturated bond within its molecule can be used. The olefinic unsaturated group is preferably derived from acrylic acid, methacrylic acid, or their derivatives. Furthermore, from the viewpoint of imparting alkali-developable properties, the photosensitive resin preferably further contains alkali-soluble groups such as phenolic hydroxyl groups and carboxyl groups, and more preferably contains carboxyl groups.

[0318] There are no particular limitations on photosensitive resins; for example, the following compounds can be listed.

[0319] Examples include: (1) a copolymer resin containing carboxylic acids obtained by copolymerizing unsaturated carboxylic acids such as (meth)acrylic acid with one or more compounds having unsaturated double bonds, etc.

[0320] (2) A photosensitive resin containing carboxylic acid obtained by using compounds with epoxy groups and unsaturated double bonds, such as glycidyl methacrylate and 3,4-epoxycyclohexyl methyl methacrylate, and compounds with unsaturated double bonds, such as methacryloyl chloride, to add olefinic unsaturated groups as side groups to copolymers of unsaturated carboxylic acids such as methacrylic acid and one or more other compounds with unsaturated double bonds.

[0321] (3) A photosensitive carboxylic acid-containing copolymer resin is obtained by reacting copolymers of compounds with epoxy groups and unsaturated double bonds, such as glycidyl methacrylate and 3,4-epoxycyclohexyl methyl methacrylate, with other compounds with unsaturated double bonds, with unsaturated carboxylic acids such as methacrylic acid, and reacting the resulting secondary hydroxyl groups with polyacid anhydrides.

[0322] (4) A photosensitive resin containing carboxylic acid is obtained by reacting a copolymer of anhydrides such as maleic anhydride with other compounds having unsaturated double bonds with compounds having hydroxyl groups and unsaturated double bonds, such as 2-hydroxyethyl methacrylate.

[0323] (5) A photosensitive resin containing carboxylic acid is obtained by reacting a polyfunctional epoxy compound with an unsaturated monocarboxylic acid, and then reacting the resulting hydroxyl group with a saturated or unsaturated polycarboxylic acid anhydride.

[0324] (6) A photosensitive resin containing hydroxyl groups and carboxylic acid is obtained by reacting hydroxyl-containing polymers such as polyvinyl alcohol derivatives with saturated or unsaturated polyacid anhydrides, followed by reacting the resulting carboxylic acid with a compound containing an epoxy group and an unsaturated double bond.

[0325] (7) A photosensitive resin containing carboxylic acid obtained by reacting the reaction product of a polyfunctional epoxy compound, an unsaturated monocarboxylic acid, or a compound having at least one alcohol hydroxyl group and one reactive group other than the alcohol hydroxyl group that reacts with an epoxy group with a saturated or unsaturated polyacid anhydride.

[0326] (8) A photosensitive resin containing carboxylic acid is obtained by reacting an unsaturated monocarboxylic acid with a polyfunctional oxetane compound having at least two oxetane rings in one molecule, and by reacting a saturated or unsaturated polyacid anhydride with the primary hydroxyl group in the obtained modified oxetane resin.

[0327] (9) A carboxylic acid-containing resin is obtained by reacting a multifunctional epoxy resin with an unsaturated monocarboxylic acid, followed by a reaction with a polyacid anhydride. This carboxylic acid-containing resin is then further reacted with a compound having one ethylene oxide ring and one or more olefinic unsaturated groups to obtain a carboxylic acid-containing photosensitive resin.

[0328] (10) A photosensitive resin containing carboxylic acid is obtained by reacting a polyfunctional phenolic resin with an epoxide or a cyclic carbonate, reacting the resulting reaction product with a monocarboxylic acid having an unsaturated double bond, or reacting the resulting reaction product with a saturated or unsaturated polyacid anhydride, but is not limited to these.

[0329] The amount of photosensitive resin may be, for example, 100 to 200 parts by weight relative to 0.1 to 10 parts by weight of the anthraquinone compound of the present invention. The photosensitive resin may be alone or in any ratio of two or more.

[0330] The photosensitive monomer is not particularly limited and can be a compound with an olefinically unsaturated double bond. Examples include: polyester (meth)acrylates, polyether (meth)acrylates, urethane (meth)acrylates, carbonate (meth)acrylates, epoxy (meth)acrylates, etc. Specifically, examples include hydroxyalkyl acrylates such as 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate; diacrylates of diols such as ethylene glycol, methoxytetraethylene glycol, polyethylene glycol, and propylene glycol; acrylamides such as N,N-dimethylacrylamide, N-hydroxymethylacrylamide, and N,N-dimethylaminopropylacrylamide; aminoalkyl acrylates such as N,N-dimethylaminoethyl acrylate and N,N-dimethylaminopropyl acrylate; polyols such as hexanediol, trimethylolpropane, pentaerythritol, dipentaerythritol, and trihydroxyethyl isocyanurate, and their ethylene oxide adducts, propylene oxide adducts, and ε-caprolactone. Polyacrylates such as adducts; polyacrylates such as phenoxyacrylates, bisphenol A diacrylates, and their ethylene oxide adducts and propylene oxide adducts; polyacrylates of glycidyl ethers such as glycerol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane triglycidyl ether, and triglycidyl isocyanurate; acrylates obtained by directly acrylate-esterifying polyols such as polyether polyols, polycarbonate diols, hydroxyl-terminated polybutadiene, and polyester polyols, or by acrylate-esterifying polyols via diisocyanate; melamine acrylates; and various methacrylates corresponding to the above acrylates. Photosensitive monomers can be used alone or in combination of two or more. Such photosensitive monomers can also be used as reactive diluents.

[0331] The amount of the photosensitive monomer can be set to 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 can be a single type or a combination of two or more types in any ratio.

[0332] There are no particular limitations on photopolymerization initiators. Examples include: oxime ester photopolymerization initiators with oxime ester groups (such as Irgacure OXE02 manufactured by BASF Japan), alkyl phenyl ketone photopolymerization initiators (such as Irgacure 907 manufactured by BASF Japan), and acylphosphine oxide photopolymerization initiators (such as Irgacure TPO manufactured by BASF Japan).

[0333] The amount of photopolymerization initiator can be set to, for example, 0.1 to 10 parts by mass relative to the anthraquinone compound of the present invention. The photopolymerization initiator can be alone or a combination of two or more in any ratio.

[0334] The anthraquinone compounds of the present invention exhibit excellent heat resistance and can also be formulated into thermosetting coloring compositions by blending them with thermosetting resins. The thermosetting resin is not particularly limited and can be any known thermosetting resin. Additionally, a thermosetting catalyst can be blended into the thermosetting coloring composition.

[0335] The coloring composition of the present invention may also contain components other than those described above, without impairing the effects of the present invention. Examples of components other than those described above include surfactants, polymerization inhibitors, antioxidants, fillers, adhesion promoters, and ultraviolet absorbers.

[0336] Example

[0337] The present invention will now be described in more detail with reference to embodiments, but the present invention is not limited to the embodiments.

[0338] <Synthesis of Compound 1>

[0339]

[0340] In a 300 mL two-necked 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. The mixture was heated to 50 °C under a nitrogen atmosphere, and then a solution prepared by dissolving terephthalic acid (1.32 g, 7.95 mmol) in N-methylpyrrolidone (30 mL) was added. The reaction was carried out at 50 °C for 1 hour under a nitrogen atmosphere. The reaction solution was filtered, and the resulting solid was washed with acetone (100 mL) and dried at 100 °C under reduced pressure for 15 hours to obtain compound 1 (2.54 g, 3.10 mmol).

[0341] FT-IR: wave number (cm-1 = 3100-3000 (aromatic CH), 1730 (ester C=O)

[0342] The FT-IR diagram is shown in Figure 1 .

[0343] Compound 1 was identified in LC-TofMS (Waters, Xevo G2-S) by peaks obtained in positive mode using electrospray ionization.

[0344] MS(m / z) = 819.25 [M+H] +

[0345] <Synthesis of Compound 2>

[0346]

[0347] In a 100 mL two-necked flask, 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. After heating to 50 °C under a nitrogen atmosphere, a solution prepared by dissolving terephthalic acid (0.427 g, 2.57 mmol) in N-methylpyrrolidone (10 mL) was added. The mixture was reacted at 50 °C under a nitrogen atmosphere for 1 hour. After adding 20 mL of ion-exchanged water to the reaction solution, the filtered solid was washed sequentially 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).

[0348] FT-IR: wave number (cm -1 = 3100-3000 (aromatic CH), 1640 (amide C=O)

[0349] The FT-IR diagram is shown in Figure 2 .

[0350] Compound 2 was identified in LC-TofMS (Waters, Xevo G2-S) by peaks obtained in positive mode using electrospray ionization.

[0351] MS(m / z) = 817.27 [M+H] +

[0352] <Synthesis of Compound 3>

[0353]

[0354] 0.7 mmol of 4-[[9,10-dihydro-4-(methylamino)-9,10-dioxo-1-anthrayl]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, N was added. 1 N 4 0.28 mmol of bis(4-hydroxyphenyl)-1,4-phenylenediamide and 0.7 mmol of N,N'-dimethylformamide were reacted. The mixture was stirred at 90 °C for 15 hours and then cooled to room temperature. The solid obtained by filtering the reaction solution was washed with 15 mL of N-methylpyrrolidone. After further washing with 15 mL of ethanol, the mixture was dried at 100 °C under reduced pressure for 15 hours to give 0.09 mmol of compound 3.

[0355] FT-IR: wave number (cm -1 = 3340 (amine NH), 3100-3000 (aromatic CH), 1720 (ester C=O), 1640 (amide C=O)

[0356] The FT-IR diagram is shown in Figure 3 .

[0357] Compound 3 was identified by peaks obtained using a time-of-flight mass analyzer (rapifle X (TOF-MS, Bruker Daltonics)) in positive mode based on laser desorption / ionization. MS (m / z) = 1058.4 [M+H] +

[0358] For the obtained compounds, thermogravimetric analysis was performed to determine their heat resistance temperature and light absorption in the ultraviolet region. Additionally, the heat resistance of the dried film containing the obtained compounds was evaluated. For some tests, compounds 4 and 5 were also evaluated in the same way for comparison.

[0359] Compound 4: Solvent Blue 11

[0360]

[0361] Compound 5: Pigment Blue 15:3

[0362]

[0363] (Heat resistance temperature)

[0364] The initial temperature was determined by thermogravimetric analysis (TGA 5500, Waters Corporation) for each compound, and this temperature was used as the heat resistance temperature. The sample size used in each determination was 1–2 mg. The determination was conducted under a nitrogen atmosphere, with the temperature increased from 50 °C to 600 °C at a rate of 10 °C per minute. The results are shown in Table 1.

[0365] [Table 1]

[0366]

[0367] Compounds 1-3 have higher heat resistance temperatures than compound 4, exhibiting excellent heat resistance.

[0368] (Absorbance and heat resistance of the dried film)

[0369] 30g of 0.3mm zirconia beads were added to a mixture of 1g each of compounds 1, 2, 4, and 5 with 19g of dipropylene glycol monomethyl ether, and dispersed using a gyratory mill for 2 hours. 3g of this dispersion was added to 10g of resin (Daicel Chemicals CYCLOMER P(ACA)Z320) to prepare a solution. The resulting solution was coated onto a glass plate using a 60μm gap applicator and pre-baked in a circulating drying oven at 90°C for 30 minutes to obtain a dried film.

[0370] The absorbance of the obtained dried films was measured using a Japanese spectrophotometer V-570 equipped with an integrating sphere. The dried films of compounds 1 and 2 are shown below. Figure 4 As shown, compared with the dried film of compound 5, it significantly suppressed light absorption in the UV region.

[0371] Next, the membrane was placed in a reflux testing machine (NIS-20-82C). The test conditions were set at 260°C in air atmosphere, and the treatment was performed three times. For the membrane before and after treatment, L was measured using a Konica Minolta CM-5 membrane. a b Calculate ΔE based on the color system data. ab.

[0372] ΔE ab is calculated using the following formula.

[0373] ΔE ab=〔(ΔL ) 2 +(Δa ) 2 +(Δb ) 2 ] 1 / 2 The results are shown in Table 2.

[0374] [Table 2]

[0375]

[0376] Compared with compound 4, the dried film containing compounds 1 and 2 showed significantly suppressed discoloration before and after the heat resistance test, and had heat resistance comparable to compound 5.

[0377] (Light absorption in the ultraviolet region)

[0378] Solutions containing compounds 1, 2, and 4 were prepared using NMP as a solvent, with the maximum absorbance being 0.1 or higher and less than 1. The absorption spectra of the prepared solutions were measured using a spectrophotometer (Nippon Spectrophotometer Co., Ltd., instrument name: V-570). The spectra normalized to the maximum absorbance are shown below. Figure 5 .

[0379] The light absorption of compounds 1 and 2 in the ultraviolet region (especially at a wavelength of 365 nm) was suppressed.

[0380] Industrial availability

[0381] The anthraquinone compounds of the present invention exhibit excellent heat resistance and, in addition, suppress light absorption in the ultraviolet region (particularly at wavelength 365 nm). Based on these properties, the coloring compositions of the present invention are suitable for use as curable compositions. The coloring compositions of the present invention are suitable for use as curable compositions, particularly suitable for photosensitive coloring compositions, and have high industrial applicability.

Claims

1. An anthraquinone compound represented by the following formula (1), In equation (1), X1 and X2 are each independently -O-, -NH-, or -S-. Y1is a divalent group derived from a (p+1) valent residue of a C1-6alkyl, phenyl or R s -R t -R s C1-6alkyl, each of said C1-6alkyl and said phenyl being optionally substituted, or Y1is a single bond, Y2 is an alkyl, phenyl, or R group with 1 to 6 carbon atoms. s -R t -R s The derived (q+1) valence residues, 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, R s Each of the alkyl, phenyl, or aralkyl groups having 1 to 6 carbon atoms is independently an alkyl, phenyl, or aralkyl group, wherein the alkyl, phenyl, and aralkyl groups having 1 to 6 carbon atoms may optionally be substituted. R t The group is selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-. R1 and R2 are each independently hydrogen atoms, selected from -OH and -OR. a -SR a -NR b R c -NR b C(=O)R 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 groups in the formula (2), (3), (4), and (5) are: a monovalent hydrocarbon group having 1 to 30 carbon atoms, a group shown in formula (2), a group shown in formula (3), a group shown in formula (4), and a group shown in formula (5), wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted. R3 is independently selected from -OH, -OR a -SR a -NR b R c -NR b C(=O)R 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 And groups in a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein the monovalent hydrocarbon group having 1 to 30 carbon atoms may optionally be substituted. p is an integer from 1 to 9. q is an integer from 1 to 9. r is an integer between 0 and 4. R a It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted. R b It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted. R c It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted. R d It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted. M a Sodium or potassium, in, Formula (1) has at least one group selected from the groups shown in Formula (2), Formula (3), Formula (4), and Formula (5). In equations (2) to (5), R5 and R6 are each independently selected from -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 groups in a monovalent hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups are optionally linked together 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)X e -C(=O)OX e -C(=O)OM b Alkyl, aralkyl, or monovalent aromatic cyclic groups may be substituted, and the two R7 groups may be optionally linked together to form a ring. L is a linking group selected from single bond, -O-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)2O-, -S(=O)2NH-, -NHS(=O)2-, -OS(=O)2-, -NHC(=O)-, and -C(=O)NH-. s is an integer between 0 and 3. t is an integer between 0 and 4. u is an integer between 0 and 3. v is an integer between 0 and 2. X a It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted. X b It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted. X c It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted. X d It is an alkyl, alkenyl, alkynyl, aralkyl, or monovalent aromatic cyclic group, which may optionally be substituted. X e It is a hydrogen atom, alkyl, alkenyl, alkynyl, aralkyl, or a monovalent aromatic cyclic group, which may optionally be substituted. M b Sodium or potassium, For connection keys.

2. The anthraquinone compound according to claim 1, wherein, Formula (1) has at least two groups selected from the groups shown in Formula (2), Formula (3), Formula (4) and Formula (5).

3. The anthraquinone compound according to claim 2, wherein, Formula (1) has at least one R1 which is a group selected from the group shown in Formula (2), Formula (3), Formula (4) and Formula (5), and has at least one R2 which is a group selected from the group shown in Formula (2), Formula (3), Formula (4) and Formula (5).

4. A coloring composition comprising the anthraquinone compound of claim 1.

5. The coloring 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, wherein it is a photosensitive coloring composition.

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

8. A cured product, which is a cured product of the coloring composition according to any one of claims 4 to 7.

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