Quinophthalone compound, coloring composition, and cured product

Abstract

Provided is a novel quinophthalone compound. The present invention is a quinophthalone compound represented by formula (1).

Description

Quinophthalone compound, colored composition and cured product

[0001] The present invention relates to a novel quinophthalone compound, a colored composition containing the quinophthalone 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 approximate the desired RGB hues by blending multiple coloring materials. Therefore, in addition to the three primary colors of RGB, coloring materials for yellow, orange, purple, etc. are also required.

[0003] Furthermore, in recent years, with regard to colorants in solder resists for consumer printed wiring boards and industrial printed wiring boards, from the viewpoint of reducing the environmental impact, phthalocyanine blue and yellow colorants that do not contain halogen atoms have become widespread in place of the conventional green colorant, chlorinated phthalocyanine green (see, for example, Patent Document 1). Furthermore, in order to clearly show that the solder resist is halogen-free from the outside, phthalocyanine blue is sometimes used as it is, retaining its blue color.

[0004] Among the coloring materials used in color filters, a well-known yellow quinophthalone pigment is Pigment Yellow 138. This structure contains halogen atoms, and there is literature (see, for example, Non-Patent Document 1) that suggests that the effect of the halogen atoms increases the fastness to heat, light, etc.

[0005] Japanese Patent Application Laid-Open No. 2000-7974

[0006] Color Materials 55 [9] 677-689 1982

[0007] Under these circumstances, there is a demand for a novel quinophthalone compound. An object of the present invention is to provide a novel quinophthalone compound, a colored composition containing the quinophthalone compound, and a cured product of the colored composition.

[0008] As a result of extensive investigations, the present inventors have found that a quinophthalone compound having a specific amide 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. Here, the specific amide structure according to the present invention refers to a structure having two or more amide bonds (-C(=O)-NH-) in a benzene ring. The gist of the present invention is as follows: [1] A quinophthalone compound represented by the following formula (1): In formula (1), R １ and R ２ are each independently —OH, —OR ａ , -NR ｂ R ｃ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ a hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2) and a group represented by formula (3), wherein the hydrocarbon group having 1 to 30 carbon atoms may be substituted; R ３ are each independently —OH, —OR ａ , -NR ｂ R ｃ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａand a hydrocarbon group having 1 to 30 carbon atoms, which may be substituted; m is an integer of 0 to 5; n is an integer of 0 to 5; p is an integer of 0 to 4; R ａ is an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; R ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; R ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; R ｄ represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; M ａ is sodium or potassium, provided that m+n is an integer of 1 or more, and formula (1) has at least one group selected from a group represented by formula (2) and a group represented by formula (3). In formula (2) and formula (3), X １ , X ２ , X ３ and X ４ are each independently —OH, —OX ａ , -NX ｂ X ｃ , -C(=O)NX ｂ X ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , —O—S(═O) ２ X ｄ , -SO ３ M ｂand a hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be bonded to each other to form a carbocyclic or heterocyclic ring, and the hydrocarbon group having 1 to 30 carbon atoms may be substituted; L １ and L ２ are each independently a single bond, —O—, —C(═O)O—, or —S(═O) ２ is a linking group selected from -O- and -NH-C(=O)-, q is an integer of 0 to 6, r is an integer of 0 to 3, s is an integer of 0 to 5, t is an integer of 0 to 4, X ａ represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; X ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group may be substituted; X ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group may be substituted; X ｄ represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; M ｂ is sodium or potassium. [2] The quinophthalone compound of [1], wherein the formula (1) has at least two groups selected from the group represented by the formula (2) and the group represented by the formula (3). [3] The quinophthalone compound of [1], wherein the formula (1) has at least two groups selected from the group represented by the formula (2) and the group represented by the formula (3). １ and R is a group selected from the group represented by formula (2) and the group represented by formula (3). ２The quinophthalone compound of [2], having at least one of the following. [4] A coloring composition containing the quinophthalone compound of any of [1] to [3]. [5] The coloring composition of [4], further containing a coloring material other than the quinophthalone 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 quinophthalone compound, a colored composition containing the quinophthalone compound, and a cured product of the colored composition are provided. The quinophthalone compound of the present invention is likely to have excellent heat resistance, and light absorption in the ultraviolet region (particularly, a wavelength of 365 nm) can be suppressed. Due to these properties, the colored composition of the present invention can be suitably used as a curable composition, and is particularly suitable for use as a photosensitive colored composition.

[0010] 1 is an FT-IR chart of Compound 1 of an Example. 2 is an FT-IR chart of Compound 2 of an Example. 3 is an FT-IR chart of Compound 3 of an Example. 4 is a TG / DTA chart of Compounds 1 and 4 of an Example. 5 is a TG / DTA chart of Compounds 1 and 5 of an Example. 6 is a chart of UV-visible absorption spectra in solutions of Compounds 1, 4, and 5 of an Example.

[0011] 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 methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, n-pentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, 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 vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, butadienyl, pentenyl, pentadienyl, hexadienyl, 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, such as vinyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, butidienyl, pentynyl, pentidienyl, and 1-hexynyl. 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. The hydrocarbon group is not particularly limited as long as it has one or more carbon atoms, and includes alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, cycloalkenyl groups, cycloalkynyl groups, aryl groups, and aralkyl groups. When the above groups are substituted, examples of the substituent include a hydroxyl group, an alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted amide group, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyano group, a nitro group, a carboxyl group (which may be in the form of a salt), a carboxylic acid ester residue, a sulfonic acid group (which may be in the form of a salt), and a sulfonic acid ester residue. The carbocyclic ring is not particularly limited as long as all of the ring-constituting atoms are carbon atoms, and examples include 4- to 20-membered rings, and preferably 4- to 14-membered rings. The carbocyclic ring may be aromatic or non-aromatic, and may be monocyclic or polycyclic.Examples include cycloalkanes (e.g., cyclopropane, cyclopentane, cyclohexane, etc.) and arenes (e.g., benzene, naphthalene, 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 heteroatoms, and examples include 4- to 20-membered rings, and preferably 4- to 14-membered rings. Examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, etc. The heterocyclic ring may be aromatic or non-aromatic, and may be monocyclic or polycyclic. Examples include a pyridine ring, lactone ring, imidazole ring, thiazole ring, oxazole ring, etc. The heterocyclic ring can contain the above-mentioned substituents and hydrocarbon groups.

[0012] The quinophthalone compound of the present invention is a compound in which at least one substituent having a quinophthalone structure (hereinafter also referred to as a quinophthalone substituent) is introduced into a compound having an amide structure.

[0013] The quinophthalone substituent is represented by formula (2) or formula (3). In formula (2) and formula (3), X １ , X ２ , X ３ and X ４ are each independently —OH, —OX ａ , -NX ｂ X ｃ , -C(=O)NX ｂ X ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , —O—S(═O) ２ X ｄ , -SO ３ M ｂ and a hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be bonded to each other to form a carbocyclic or heterocyclic ring, and the hydrocarbon group having 1 to 30 carbon atoms may be substituted; L １ and L２ are each independently a single bond, —O—, —C(═O)O—, or —S(═O) ２ is a linking group selected from -O- and -NH-C(=O)-, q is an integer of 0 to 6, r is an integer of 0 to 3, s is an integer of 0 to 5, t is an integer of 0 to 4, X ａ represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; X ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group may be substituted; X ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group may be substituted; X ｄ represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; M ｂ is sodium or potassium.

[0014] In formula (2), X １ may be bonded to either the pyridine ring or the benzene ring. ３ and L ２ may be bonded to the pyridine ring or the benzene ring. ２ is preferably bonded to the benzene ring in formula (3).

[0015] L １ and L ２ When L is —C(═O)O— or —NH—C(═O)—, it is preferred that the carbon atom of these groups is directly bonded to formula (2) or formula (3). １ and L ２ is -S (=O) ２ In the case of O—, it is preferred that the sulfur atom of this group is directly bonded to formula (2) or formula (3). １ and L ２are each independently preferably —NH—C(═O)—, —C(═O)O— or —O—, more preferably —C(═O)O— or —O—.

[0016] q is preferably 0 or 1. r is preferably 0 or 1. s is preferably 0 or 1. t is preferably 0 or 1.

[0017] X １ , X ２ , X ３ or X ４ When present, these are preferably each independently -OH, an alkyl group having 1 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms which is partially or fully substituted with fluorine, or a halogen atom.

[0018] The quinophthalone substituent of formula (2) includes groups represented by the following formulae (2-1) to (2-4). In formulas (2-1) to (2-4), L １０ represents a single bond, -O-, -C(=O)O-, -S(=O) ２ is a linking group selected from —O— and —NH—C(═O)—; １ ~Y ６ and Y ７ ~Y １０ are each independently a hydrogen atom, —OH, or —OX ａ , -NX ｂ X ｃ , -C(=O)NX ｂ X ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , —O—S(═O) ２ X ｄ , -SO ３ M ｂ and a hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a carbocyclic ring or a heterocyclic ring, and the hydrocarbon group having 1 to 30 carbon atoms may be substituted.

[0019] L １０ is preferably —C(═O)O—, —NH—C(═O)—, or —O—, and more preferably —C(═O)O— or —O—. １ and Y ２ is preferably a hydrogen atom, —OH, or an alkyl group having 1 to 30 carbon atoms. ３ ~Y ６ is preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 30 carbon atoms. ７ ~Y １０ is preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 30 carbon atoms.

[0020] Examples of the quinophthalone substituent of formula (3) include groups represented by the following formulae (3-1) to (3-5). In formulas (3-1) to (3-5), L ２０ represents a single bond, -O-, -C(=O)O-, -S(=O) ２ is a linking group selected from —O— and —NH—C(═O)—; １ ~Y １０ are each independently a hydrogen atom, —OH, or —OX ａ , -NX ｂ X ｃ , -C(=O)NX ｂ X ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OX ｄ , -OC(=O)X ｄ , -COOM ｂ , -SO ３ H, -S(=O) ２ OX ｄ , —O—S(═O) ２ X ｄ , -SO ３ M ｂ and a hydrocarbon group having 1 to 30 carbon atoms, wherein adjacent groups may be linked to each other to form a carbocyclic ring or a heterocyclic ring, and the hydrocarbon group having 1 to 30 carbon atoms may be substituted.

[0021] L ２０is preferably —C(═O)O—, —NH—C(═O)—, or —O—, and more preferably —C(═O)O— or —O—. １ and Y ２ , a hydrogen atom, —OH, or an alkyl group having 1 to 30 carbon atoms is preferred. ３ ~Y ６ is preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 30 carbon atoms. ７ ~Y １０ is preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 30 carbon atoms.

[0022] The quinophthalone substituent is preferably a group represented by formula (2).

[0023] The quinophthalone compound of the present invention is represented by formula (1), １ and R ２ has at least one quinophthalone substituent represented by formula (2) or formula (3). In formula (1), R １ and R ２ are each independently —OH, —OR ａ , -NR ｂ R ｃ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ a hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2) and a group represented by formula (3), wherein the hydrocarbon group having 1 to 30 carbon atoms may be substituted; R ３ are each independently —OH, —OR ａ , -NR ｂ R ｃ , —C(═O)NR ｂ R ｃ, halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ and a hydrocarbon group having 1 to 30 carbon atoms, which may be substituted; m is an integer of 0 to 5; n is an integer of 0 to 5; p is an integer of 0 to 4; R ａ is an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; R ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; R ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; R ｄ represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; M ａ is sodium or potassium, provided that m+n is an integer of 1 or more, and formula (1) has at least one group selected from a group represented by formula (2) and a group represented by formula (3).

[0024] Formula (1) preferably has at least two quinophthalone substituents represented by formula (2) or formula (3), and the quinophthalone substituents R １ and at least one quinophthalone substituent R ２ It is more preferred that the quinophthalone substituent R １and one quinophthalone substituent, R ２ It is particularly preferred that the compound has one of the following:

[0025] R １ and R ２ Although the quinophthalone group may have only a quinophthalone substituent, other substituents may also be present. When a substituent other than the quinophthalone substituent is present, it is preferably a halogen atom, more preferably a chlorine atom or a bromine atom.

[0026] The quinophthalone compound of the present invention includes a compound of formula (1-1). In formula (1-1), R １１ ~R ２０ Among them, R １３ and R １８ are groups selected from the group represented by formula (2) and the group represented by formula (3), and the others are each independently a hydrogen atom, —OH, —OR ａ , -NR ｂ R ｃ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ , -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ a hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2) and a group represented by formula (3), wherein the hydrocarbon group having 1 to 30 carbon atoms may be substituted; R ２１ ~R ２４ are each independently a hydrogen atom, —OH, —OR ａ , -NR ｂ R ｃ , —C(═O)NR ｂ R ｃ , halogen atoms, —CN, —NO ２ , -COOH, -C(=O)OR ｄ, -OC(=O)R ｄ , -COOM ａ , -SO ３ H, -S(=O) ２ OR ｄ , —O—S(═O) ２ R ｄ , -SO ３ M ａ and hydrocarbon groups having 1 to 30 carbon atoms, which may be substituted.

[0027] In formula (1-1), R １３ and R １８ are both quinophthalone substituents represented by formula (2) or (3), and １３ and R １８ and R are quinophthalone substituents represented by formula (2). １１ ~R １２、 R １４ ~R １７、 R １９ ~R ２０ is preferably a hydrogen atom or a halogen atom (chlorine atom, bromine atom), more preferably a hydrogen atom. ２１ ~R ２４ is preferably a hydrogen atom.

[0028] The quinophthalone compound of the present invention is a compound represented by the formula (1-1), wherein R １３ and R １８ and R is a quinophthalone substituent represented by formula (2) or (3). １３ and R １８ The other is —OH or —NH ２ and the monosubstituted compound is preferably L １０ or L ２０ When L has -NHC(=O)-, the other is preferably -OH. １０ or L ２０ When the other has -NH ２ It is preferable that:

[0029] In formula (1-1), R １３ and R １８and R are quinophthalone substituents represented by formula (2) or (3) (disubstituted compounds), including compounds represented by formulas (i) to (vii) below. １３ and R １８ The compound of formula (i) is a quinophthalone substituent represented by formula (2-1), the compound of formula (ii) is a quinophthalone substituent represented by formula (2-2), the compound of formula (iii) is a quinophthalone substituent represented by formula (3-1), the compound of formula (iv) is a quinophthalone substituent represented by formula (3-2), the compound of formula (v) is a quinophthalone substituent represented by formula (3-3), the compound of formula (vi) is a quinophthalone substituent represented by formula (3-4), and the compound of formula (vii) is a quinophthalone substituent represented by formula (3-5). In formulas (i) to (vii), R １１ , R １２ , R １４ ~R １７ , R １９ , R ２０ , R ２１ ~R ２４ , Y １ ~Y １０ , L １０ and L ２０ The above definitions and preferred examples apply to L. When a plurality of the above groups are present, they may be the same or different. １ and L ２ When L is -C(=O)O- or -NH-C(=O)-, it is preferred that the carbon atom of these groups is directly bonded to the quinophthalone substituent, and that -O- or -NH- of these groups is directly bonded to formula (1-1). １ and L ２ is -S (=O) ２ In the case of O-, it is preferred that the sulfur atom of this group is directly bonded to the quinophthalone substituent, and that -O- of these groups is directly bonded to formula (1-1).

[0030] L １０Examples of compounds of formula (i) in which is —C(═O)O— include the following: In the following chemical formulas, Me represents a methyl group, and Bn represents a benzyl group (the same applies hereinafter in this specification).

[0031] L １０ Examples of the compound of formula (ii) in which is —C(═O)O— include the following:

[0032] L ２０ Examples of the compound of formula (iii) in which is —C(═O)O— include the following:

[0033] L ２０ Examples of the compound of formula (iv) in which is —C(═O)O— include the following:

[0034] L ２０ Examples of compounds of formula (v) in which is —C(═O)O— include the following:

[0035] L ２０ Examples of the compound of formula (vi) in which is —C(═O)O— include the following:

[0036] L ２０ Examples of the compound of formula (vii) in which is —C(═O)O— include the following:

[0037] In formula (1-1), R １３ and R １８and the other is —OH (monosubstituted compounds), １０ or L ２０ Examples of compounds in which is —C(═O)O— include the following:

[0038] Examples of compounds in which the quinophthalone substituent is represented by formula (2-1) include the following:

[0039] Examples of compounds in which the quinophthalone substituent is represented by formula (2-2) include the following:

[0040] Examples of compounds in which the quinophthalone substituent is represented by formula (3-1) include the following:

[0041] Examples of compounds in which the quinophthalone substituent is represented by formula (3-2) include the following:

[0042] Examples of compounds in which the quinophthalone substituent is represented by formula (3-3) include the following:

[0043] Examples of compounds in which the quinophthalone substituent is represented by formula (3-4) include the following:

[0044] Examples of compounds in which the quinophthalone substituent is represented by formula (3-5) include the following.

[0045] L in the compounds of formulas (i) to (vii) １０ or L ２０ Also preferred are compounds in which is —NH—C(═O)— (amide-altered disubstituted compounds). For example, the following compounds can be mentioned:

[0046] In formula (1-1), R １３ and R １８ is a quinophthalone substituent represented by formula (2) or formula (3), and the other is -NH ２ Among the compounds (monosubstituted compounds) in which L １０ Examples of compounds in which is —NHC(═O)— include the following:

[0047] The quinophthalone compound of the present invention can be obtained by reacting a compound having an amide structure with a compound having a quinophthalone substituent.

[0048] As the compound having an amide structure, a compound represented by formula (4) or a derivative thereof (hereinafter, these may be collectively referred to as compounds of formula (4) or the like), a compound represented by formula (4') or a derivative thereof (hereinafter, these may be collectively referred to as compounds of formula (4') or the like), etc. can be used. １１ ~R ２０ and R ２１ ~R ２４ Examples include derivatives having a substituent at a position corresponding to the position of the quinophthalone. The substituent may be introduced after the quinophthalone substituent is introduced.

[0049] It is known that the compound of formula (4) can be synthesized by the following reaction.

[0050] In the above reaction, instead of aminophenol, a substituted aminophenol in which hydrogen atoms on the aromatic ring of aminophenol are substituted with a substituent may be used. By using such a substituted aminophenol, a substituent can be introduced into the compound represented by formula (4). Examples of the substituted aminophenol include aminophenols substituted with alkyl groups such as 4-amino-3-methylphenol and 4-amino-2,3-xylenol; aminophenols substituted with halogen atoms such as 4-amino-3-fluorophenol and 4-amino-3-chlorophenol; and aminophenols substituted with alkoxy groups such as 4-amino-2-methoxyphenol.

[0051] Furthermore, in the above reaction, by using an excess amount of phenylenediamine instead of aminophenol, a compound of formula (4') can be synthesized. Furthermore, instead of phenylenediamine, a substituted phenylenediamine in which hydrogen atoms on the aromatic ring of phenylenediamine are substituted with a substituent may be used. By using such a substituted phenylenediamine, a substituent can be introduced into the compound of formula (4'). Examples of substituted phenylenediamines include phenylenediamines substituted with alkyl groups such as 2,5-diaminotoluene and 2,5-dimethyl-1,4-phenylenediamine; phenylenediamines substituted with halogen atoms such as 2-chloro-1,4-phenylenediamine and 2,3,5,6-tetrafluoro-1,4-phenylenediamine; phenylenediamines substituted with fluoroalkyl groups such as 2-(trifluoromethyl)-1,4-phenylenediamine; and phenylenediamines substituted with sulfo groups such as 1,4-phenylenediamine-2-sulfonic acid.

[0052] The compound of formula (4) can also be synthesized by hydrolyzing polyethylene terephthalate (PET), for example, by the method described in Polymer Chemistry (2013), 4(5), 1610-1616.

[0053] As a compound having a quinophthalone substituent, in formula (2) and formula (3), １, L in formula (3) ２ A compound in which the linking moiety of this compound is replaced with a corresponding monovalent group can be used. The compound of formula (1) can be obtained by reacting the monovalent group corresponding to the linking moiety of this compound with a hydroxyl group of a compound of formula (4) or a derivative thereof, or an amino group of a compound of formula (4') or a derivative thereof.

[0054] In the following, in formula (1-1), R １３ and R １８ Both are represented by formula (2-1), and L １０ The synthesis of compounds in which the quinophthalone substituent is —C(═O)O— (ester bond) will be mainly described.

[0055] For the introduction of a quinophthalone substituent, a compound represented by formula (5) or a derivative thereof (hereinafter, sometimes referred to as a compound of formula (5) or the like) can be used. １ ~Y ８ and Y １０ The corresponding substituent may be introduced after the reaction.

[0056] The compound of formula (5) can be obtained by reacting 2-methylquinoline with trimellitic anhydride by a known method.

[0057] The amounts of the compound of formula (4) etc. and the compound of formula (5) etc. used can be such that the compound of formula (5) etc. is in excess, and preferably the amount of the compound of formula (5) etc. is more than 2 moles per mole of the compound of formula (4) etc. Note that, for example, when the compound of formula (5) etc. is used in an amount of less than 2 moles per mole of the compound of formula (4) etc., a quinophthalone compound having one quinophthalone substituent can also be obtained.

[0058] The reaction temperature for the reaction of the compound of formula (4) or the like with the compound of formula (5) or the like can be 0 to 120°C, preferably 80 to 100°C. The reaction time can be 1 to 24 hours, more preferably 12 to 20 hours. The reaction can be carried out under atmospheric pressure.

[0059] The reaction between the compound of formula (4) or the like and the compound of formula (5) or the like 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 also be used.

[0060] 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.

[0061] 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.

[0062] When the linking moiety is other than -C(=O)O- (ester bond) or when the quinophthalone substituent is represented by formula (3), synthesis can be carried out in the same manner as above. For example, when a compound of formula (4') is used instead of a compound of formula (4), a quinophthalone compound in which the linking moiety is -NH-C(=O)- (amide bond) can be obtained. Furthermore, when a compound of formula (5) is used instead of a compound in which the position of the carboxyl group is different, for example, L of each of formulas (3-1) to (3-5) can be used, ２０ By using a compound having a carboxyl group at the position corresponding to the formula (1), a quinophthalone compound in which the quinophthalone substituent is represented by formula (3) can be obtained.

[0063] A specific example of a method for synthesizing the quinophthalone compound of the present invention is the synthesis scheme shown below.

[0064] The quinophthalone compound of the present invention can be used in the production of various paints, water-based or oil-based inks, etc., and is also useful as a functional dye for recording materials, etc.

[0065] The present invention also relates to a coloring composition containing the quinophthalone compound of the present invention. The coloring composition contains the quinophthalone compound of the present invention alone or in any combination of two or more kinds in any ratio.

[0066] The coloring composition may contain a colorant other than the quinophthalone compound of the present invention. The colorant 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, 265; blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60; purple pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38; green pigments such as C.I. Pigment Green 7, 36, 58, etc. Examples of suitable dyes include compounds classified as compounds having a hue other than 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.

[0067] Coloring materials other than the quinophthalone compound of the present invention can be used in an amount that does not impair the effects of the present invention.

[0068] 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.

[0069] 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 quinophthalone compound of the present invention. The binder resin may be used alone or in combination of two or more kinds in any ratio.

[0070] 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.

[0071] 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 quinophthalone 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 be further blended into the photosensitive coloring composition.

[0072] 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.

[0073] (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 at least one alcoholic hydroxyl group in one molecule and one reactive group other than the alcoholic hydroxyl group that reacts with the 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 at least two oxetane rings in one molecule 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; and (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 one oxirane ring and one or more ethylenically unsaturated groups in the molecule, but these examples are not limited to these.

[0074] The amount of the photosensitive resin may be, for example, 100 to 200 parts by mass per 0.1 to 10 parts by mass of the quinophthalone compound of the present invention. The photosensitive resin may be used alone or in combination of two or more kinds in any ratio.

[0075] 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.

[0076] 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 quinophthalone compound of the present invention. The photosensitive resin may be used alone or in combination of two or more kinds in any ratio.

[0077] 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).

[0078] The amount of the photopolymerization initiator may be, for example, 0.1 to 10 parts by mass relative to 0.1 to 10 parts by mass of the quinophthalone compound of the present invention. The photopolymerization initiator may be used alone or in combination of two or more kinds in any ratio.

[0079] The quinophthalone compound of the present invention is likely to have excellent heat resistance, and a thermosetting resin may be blended into the coloring composition of the present invention to form a thermosetting coloring composition. The thermosetting resin is not particularly limited, and a known thermosetting resin may be used. In addition, a thermosetting catalyst may be blended into the thermosetting coloring composition.

[0080] 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.

[0081] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0082] <Synthesis of Compound 1> Compound 1 was synthesized according to the following scheme.

[0083] 3.6 mmol of 2,3-dihydro-1,3-dioxy-2-(2-quinolinyl)-1H-indene-5-carboxylic acid (compound 4), 4.3 mmol of N,N'-dicyclohexylcarbodiimide, 4.3 mmol of 1-hydroxybenzotriazole, and 57 mL of N-methylpyrrolidone were mixed and heated under a nitrogen atmosphere. After stirring at 60°C for 30 minutes, １ , N ４ 1.4 mmol of N,N'-bis(4-hydroxyphenyl)-1,4-benzenedicarboxamide and 3.6 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 1.4 mmol of Compound 1.

[0084] FT-IR: wave number (cm －１ ) = 3340 (amide N-H), 3100-3000 (aromatic C-H), 1720 (ester C=O), 1640 (amide C=O), 1625 (quinophthalone C=O). The IR chart is shown in Figure 1.

[0085] Compound 1 was identified from the peak obtained in positive mode by laser desorption ionization using a time-of-flight mass spectrometer (rapifleX (TOF-MS, Bruker Daltonics)). MS (m / z) = 947.4 ([M+H] ＋ )

[0086] <Synthesis of Compound 2> Compound 2 was synthesized according to the following scheme.

[0087] 2-(8-nitroquinolin-2(1H)-ylidene)-1,3-dioxo-2,3-dihydro-1H-indene-5-carboxylic acid 2.76 mmol, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 6.87 mmol, 1-hydroxybenzotriazole 3.29 mmol, N-methylpyrrolidone 20 mL, N １ , N ４1.31 mmol of N,N-bis(4-hydroxyphenyl)-1,4-benzenedicarboxamide and 2.7 mmol of N,N-dimethylformamide were mixed and heated under a nitrogen atmosphere. After stirring at 100°C for 27 hours, the mixture was cooled to room temperature. The solid obtained by filtering the reaction solution was washed with 60 mL of N-methylpyrrolidone. After further washing with 60 mL of methanol, the solid was dried at 100°C under reduced pressure for 15 hours to obtain 0.97 mmol of compound 2. FT-IR: Wave number (cm －１ )=3310 (amide N—H), 3100-3000 (aromatic C—H), 1730 (ester C═O), 1640 (amide C═O), 1625 (quinophthalone C═O). The IR chart is shown in FIG. 2.

[0088] Compound 2 was identified from the peak obtained in positive mode by laser desorption ionization using a time-of-flight mass spectrometer (rapifleX (TOF-MS, Bruker Daltonics)). MS (m / z) = 1037.3 ([M+H] ＋ )

[0089] <Synthesis of Compound 3> Compound 3 was synthesized according to the following scheme.

[0090] 2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-1,2-dihydroquinoline-6-carboxylic acid 3.15 mmol, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 6.00 mmol, 1-hydroxybenzotriazole 3.75 mmol, N-methylpyrrolidone 20 mL, N １ , N ４ 1.50 mmol of N,N-bis(4-hydroxyphenyl)-1,4-benzenedicarboxamide and 3.2 mmol of N,N-dimethylformamide were mixed and heated under a nitrogen atmosphere. The mixture was stirred at 100°C for 5 hours and then cooled to room temperature. The solid obtained by filtering the reaction solution was washed with 60 mL of N-methylpyrrolidone. After further washing with 60 mL of methanol, the solid was dried at 100°C under reduced pressure for 15 hours to obtain 1.18 mmol of compound 3.

[0091] FT-IR: wave number (cm －１) = 3360 (amide N-H), 3100-3000 (aromatic C-H), 1725 (ester C=O), 1640 (amide C=O), 1625 (quinophthalone C=O). The IR chart is shown in Figure 3.

[0092] Compound 3 was identified from the peak obtained in positive mode by laser desorption ionization using a time-of-flight mass spectrometer (rapifleX (TOF-MS, Bruker Daltonics)). MS (m / z) = 947.3 ([M+H] ＋ )

[0093] The obtained Compound 1 was evaluated for heat resistance by thermogravimetry, color fastness, and light absorption in the ultraviolet region. For comparison, the following Compounds 4 and 5 were also evaluated in the same manner. Compound 4: 2,3-dihydro-1,3-dioxy-2-(2-quinolinyl)-1H-indene-5-carboxylic acid Compound 5: Pigment Yellow 147 (AGR)

[0094] (Heat Resistance) Compound 1 was subjected to thermogravimetric measurement using a thermogravimetric analyzer (manufactured by Waters, device name: TGA5500) to evaluate its heat resistance. The amount of sample used per measurement was 1 to 2 mg. The measurement was performed in a nitrogen atmosphere, with the temperature rising from 50°C to 600°C at a rate of 10°C per minute. The results are shown in Figures 4 and 5. The Td5 (temperature at which 5% weight loss occurs) was 440°C for Compound 1, 380°C for Compound 4, and 450°C for Compound 5.

[0095] (Color Fixation) Compound 1 and Compound 4 were dispersed in 2 g of N-methylpyrrolidone, and 0.986 g of resin (Cyclomer P (ACA) Z320 manufactured by Daicel Chemical Industries, Ltd.) and 0.014 g of a 4 wt % solution of leveling agent (BYK-333 manufactured by BYK-Chemie Co., Ltd.) in propylene glycol monomethyl ether acetate (PMA) were added to prepare a solution. The obtained solution was applied to a glass plate to a thickness of 2 μm and prebaked on a hot plate at 100° C. for 3 minutes. Next, the film was kept in a thermostatic bath at 230° C. for 2 hours, and the film after keeping was visually observed to confirm the color fixation. Compound 1: No change in color before and after keeping Compound 4: Significant color fading after keeping

[0096] (Light absorption in the ultraviolet region) Using NMP as a solvent, solutions were prepared by dissolving Compounds 1, 4, and 5 so that the concentration in NMP was 1.0 mmol / L. The absorption spectrum of the prepared solution was measured using a spectrophotometer (manufactured by JASCO Corporation, instrument name: V-770). The results are shown in FIG.

[0097] As shown in the thermogravimetric measurement results in Figures 4 and 5, Compound 1 of the present invention has improved heat resistance compared to Compound 4, which is a raw material, and also exhibits heat resistance comparable to that of Compound 5, a conventional yellow pigment (Pigment Yellow 147). On the other hand, as shown in Figure 6, Compound 1 of the present invention had significantly reduced light absorption at 365 nm compared to Compound 5. Furthermore, when a substrate coated with a coloring composition was exposed to heat, significant fading due to heat was observed in the case where Compound 4, which is a raw material, was used in the coloring composition. In contrast, Compound 1 of the present invention did not change color due to heat, and it was confirmed that it has heat resistance even on a substrate coated with a coloring composition.

[0098] The quinophthalone compound of the present invention is likely to have excellent heat resistance, and can suppress light absorption in the ultraviolet region (particularly, a wavelength of 365 nm). Due to these properties, the coloring composition of the present invention can be suitably used as a curable composition, and the coloring composition of the present invention can be suitably used as a curable composition, and is particularly suitable for a photosensitive coloring composition, and is highly useful in industry.

Claims

1. A quinophthalone compound represented by the following formula (1): In formula (1), R １ and R ２ each independently represents -OH, -OR ａ , -NR ｂ R ｃ , -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 hydrocarbon group having 1 to 30 carbon atoms, a group represented by formula (2) and a group represented by formula (3), the hydrocarbon group having 1 to 30 carbon atoms being optionally substituted; R ３ each independently represents -OH, -OR ａ , -NR ｂ R ｃ , -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 hydrocarbon group having 1 to 30 carbon atoms, which may be substituted; m is an integer of 0 to 5; n is an integer of 0 to 5; p is an integer of 0 to 4; R ａ is an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group being optionally substituted; R ｂ R is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; ｃ R is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, and the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group may be substituted; ｄ is an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group being optionally substituted; M ａ is sodium or potassium, with the proviso that m+n is an integer of 1 or more, and formula (1) has at least one group selected from a group represented by formula (2) and a group represented by formula (3). In formula (2) and formula (3), X １ , X ２ , X ３ and X ４ each independently represents -OH, -OX ａ , -NX ｂ X ｃ , -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 O.X. ｄ , -OS(=O) ２ X ｄ , -SO ３ M ｂ and a hydrocarbon group having 1 to 30 carbon atoms, adjacent groups may be bonded to each other to form a carbocyclic or heterocyclic ring, and the hydrocarbon group having 1 to 30 carbon atoms may be substituted; L １ and L ２ are each independently a single bond, -O-, -C(=O)O-, or -S(=O) ２ is a linking group selected from -O- and -NH-C(=O)-, q is an integer of 0 to 6, r is an integer of 0 to 3, s is an integer of 0 to 5, t is an integer of 0 to 4, and X ａ is an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group being optionally substituted; X ｂ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group being optionally substituted; X ｃ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group being optionally substituted; X ｄ is an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, the alkyl group, the alkenyl group, the alkynyl group, and the aralkyl group being optionally substituted; M ｂ is sodium or potassium.

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

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

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

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