Colorant

Abstract

The purpose of the present invention is to provide a colorant capable of producing a coating film having improved green spectral characteristics. The colorant comprises a compound represented by formula (I), and is characterized in that the ratio of the number of groups represented by formula (T-2) in the colorant to the number of Al atoms contained in the compound represented by formula (I) is 0.1-3. [In formula (I), R1 and R2 each independently represent a hydrogen atom, a hydroxyl group,-R13, or-O-R13. When at least one of R1 and R2 represents-R13 or-O-R13, R1 and R2 may bond to each other to form a ring. And ring T1, ring T2, ring T3, and ring T4 each independently represent a group represented by formula (T-1) or formula (T-2). ] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound, a colorant, a colored resin composition, a color filter, a display device, and a solid-state imaging element. Background Art

[0002] Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are manufactured from colored resin compositions. As colorants used in such colored resin compositions, compounds represented by formula (x1) are known (Patent Document 1).

[0003]

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 2022 / 024926 Summary of the invention

[0007] The color filter is required to have good spectral characteristics of a target color. For example, a green color filter preferably exhibits good green spectral characteristics.

[0008] Therefore, an object of the present invention is to provide a coloring agent and a colored resin composition capable of producing a coating film having improved green spectral characteristics.

[0009] The gist of the present invention is as follows.

[0010] [1] A colorant comprising a compound represented by formula (I),

[0011] The ratio of the number of groups represented by the formula (T-2) in the colorant to the number of Al atoms in the compound represented by the formula (I) is 0.1 to 3.

[0012]

[0013] [In formula (I),

[0014] R 1 and R 2 Each independently represents a hydrogen atom, a hydroxyl group, -R 13 or -O-R 13 . R 1 and R 2 At least one of them indicates -R 13 or -O-R 13 When R 1 and R 2 They may be bonded to each other to form a ring.

[0015] Ring T1 , Ring T 2 , Ring T 3 and Ring T 4 Each independently represents a group represented by formula (T-1) or formula (T-2).

[0016]

[0017] (In formula (T-1), R 3 ~R 6 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group. * indicates the bonding site with the pyrrole ring. )

[0018]

[0019] (In formula (T-2), R 7 ~R 12 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group. * indicates the bonding site with the pyrrole ring. )

[0020] R 13 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 13 , they may be the same as or different from each other.

[0021] R 14 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 14 , they may be the same as or different from each other.]

[0022] [2] The colorant according to [1], comprising at least cyclic T 1 , Ring T 2 , Ring T 3 and Ring T 4 The compound wherein 1 to 3 of the groups are groups represented by the formula (T-2) is regarded as the compound represented by the above formula (I).

[0023] [3] A colored resin composition comprising the colorant according to [1] or [2], a resin, and a solvent.

[0024] [4] The colored resin composition according to [3], further comprising a polymerization initiator and a polymerizable compound.

[0025] [5] A color filter formed from the colored resin composition according to [3] or [4].

[0026] [6] A display device comprising the color filter described in [5].

[0027] [7] A solid-state imaging element comprising the color filter described in [5].

[0028] [8] A compound represented by formula (II).

[0029]

[0030] [In formula (II),

[0031] R 1 and R 2 Same as above.

[0032] Ring T 21 , Ring T 22 , Ring T 23 and Ring T 24 Each independently represents a group represented by formula (T-1) or formula (T-2). 21 , Ring T 22 , Ring T 23 and Ring T 24 1 to 3 of them represent groups represented by formula (T-2).

[0033] The groups represented by formula (T-1) and formula (T-2) are the same as those described above.]

[0034] According to the present invention, a coloring agent and a colored resin composition capable of producing a coating film having improved green spectrum characteristics can be provided. DETAILED DESCRIPTION

[0035] <<Coloring Agent>>

[0036] The colorant of the present invention is a colorant containing a compound represented by formula (I), characterized in that the ratio of the number of groups represented by formula (T-2) in the above colorant to the number of Al atoms possessed by the compound represented by formula (I) is 0.1 to 3. By using such a colorant, a coating film with improved green spectral characteristics can be produced. For example, in the obtained coating film, it can be said that the smaller the distance between the xy chromaticity coordinates when measuring the xy chromaticity coordinates in the XYZ color system of CIE and the chromaticity coordinates ((x, y) = (0.30, 0.60)) as the vertex of green in the sRGB standard, the better the green spectral characteristics. In addition, it can be said that the transmittance X of the obtained coating film at a wavelength of 570nm is 570 Transmittance X at wavelength 530nm 530 The ratio (X 570 / X 530 ) is closer to 1, the better the green spectrum characteristics are.

[0037] In a preferred embodiment, the use of the coloring agent of the present invention can also improve the light resistance of the resulting coating film.

[0038]

[0039] [In formula (I),

[0040] R 1 and R 2 Each independently represents a hydrogen atom, a hydroxyl group, -R 13 or -O-R 13 . R 1 and R 2 At least one of them indicates -R 13 or -O-R 13 When R 1 and R 2 They may be bonded to each other to form a ring.

[0041] Ring T 1 , Ring T 2 , Ring T 3 and Ring T 4 Each independently represents a group represented by formula (T-1) or formula (T-2).

[0042]

[0043] (In formula (T-1), R 3 ~R 6 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R14 ) 2 , halogen atom or nitro group. * indicates the bonding site with the pyrrole ring. )

[0044]

[0045] (In formula (T-2), R 7 ~R 12 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group. * indicates the bonding site with the pyrrole ring. )

[0046] R 13 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 13 , they may be the same as or different from each other.

[0047] R 14 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 14 , they may be the same as or different from each other.]

[0048] As long as the ratio of the number of groups represented by formula (T-2) in the colorant to the number of Al atoms possessed by the compound represented by formula (I) is 0.1 to 3, the colorant of the present invention may contain one compound represented by formula (I) alone, or may contain two or more compounds represented by formula (I) in combination. The ratio of the number of groups represented by the above formula (T-2) to the number of Al atoms is 0.1 to 3, preferably 0.1 to 2.5, more preferably 0.25 to 2.0, further preferably 0.4 to 2.0, and further preferably 0.5 to 2.0. By adjusting the ratio to the above range, the green spectral characteristics of the obtained coating film can be improved. It should be noted that the ratio of the number of groups represented by formula (T-2) to the number of Al atoms can be determined by, for example, obtaining the integral value of the signal corresponding to the hydrogen atom possessed by the group represented by formula (T-1) contained in the colorant and the integral value of the signal corresponding to the hydrogen atom possessed by the group represented by formula (T-2) in NMR analysis, and calculating the ratio of the number of groups represented by formula (T-2) possessed by the molecule of compound 1 represented by formula (I).

[0049] In formula (I), ring T 1 , Ring T 2 , Ring T 3 and Ring T 4Each independently represents a group represented by formula (T-1) or formula (T-2). That is, examples of the compound represented by formula (I) include

[0050] Ring T 1 ~Ring T 4 A compound in which all groups are represented by the formula (T-1) (hereinafter, sometimes referred to as compound (Ia));

[0051] Ring T 1 ~Ring T 4 A compound in which any one of them is a group represented by formula (T-2) and the remaining three are groups represented by formula (T-1) (hereinafter, sometimes referred to as compound (Ib));

[0052] Ring T 1 ~Ring T 4 A compound in which any two of the groups are groups represented by formula (T-2) and the remaining two are groups represented by formula (T-1) (hereinafter, sometimes referred to as compound (Icd));

[0053] Ring T 1 ~Ring T 4 A compound in which any three of them are groups represented by formula (T-2) and the remaining one is a group represented by formula (T-1) (hereinafter, sometimes referred to as compound (Ie));

[0054] Ring T 1 ~Ring T 4 A compound in which all groups are represented by the formula (T-2) (hereinafter, sometimes referred to as compound (If)). As compound (Icd), ring T 1 and Ring T 3 is a group represented by formula (T-2) and T 2 and Ring T 4 Compounds having groups represented by formula (T-1) Such compounds in which two groups represented by formula (T-1) and two groups represented by formula (T-2) are arranged in opposite rings (hereinafter sometimes referred to as compound (Ic)) may also be ring T 2 and Ring T 3 is a group represented by formula (T-2) and ring T 1 and Ring T 4 The compound having a group represented by the formula (T-1) is a compound in which two groups represented by the formula (T-1) and two groups represented by the formula (T-2) are arranged on adjacent rings (hereinafter, sometimes referred to as compound (Id)).

[0055] The colorant of the present invention preferably contains a compound represented by the following formula (II) (hereinafter, sometimes referred to as compound (II)). Compound (II) is a compound represented by formula (I) wherein ring T 1 , Ring T2 , Ring T 3 and Ring T 4 A compound wherein one, two or three of the groups are groups represented by formula (T-2). That is, examples of compound (II) include compound (Ib), compound (Ic), compound (Id) and compound (Ie).

[0056]

[0057] [In formula (II),

[0058] R 1 and R 2 Same as above.

[0059] Ring T 21 , Ring T 22 , Ring T 23 and Ring T 24 Each independently represents a group represented by formula (T-1) or formula (T-2). 21 , Ring T 22 , Ring T 23 and Ring T 24 1 to 3 of them represent the group represented by formula (T-2). It should be noted that the groups represented by formula (T-1) and formula (T-2) are the same as those described above.]

[0060] The colorant of the present invention preferably contains at least compound (II) (i.e., at least one selected from compound (Ib), compound (Ic), compound (Id) and compound (Ie)), more preferably contains at least one selected from compound (Ib), compound (Ic) and compound (Id), and further preferably contains at least compound (Ib). In addition, the colorant may contain all of compound (Ia), compound (Ib), compound (Ic), compound (Id), compound (Ie) and compound (If).

[0061] Next, the present invention will be described in more detail with reference to partial structures of compounds represented by formula (I).

[0062] R 13 and R 14 The hydrocarbon group having 1 to 20 carbon atoms represented by may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or cyclic (alicyclic hydrocarbon group).

[0063] Examples of the saturated or unsaturated chain hydrocarbon group include straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-eicosyl;

[0064] Isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl, Branched-chain alkyl groups such as 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butylhexyl;

[0065] ethenyl, vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1,3-butadienyl, 3-methyl-1,2-butadienyl, 1-(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl , 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl and the like alkenyl groups;

[0066] ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), butynyl (e.g., 1-butynyl, 2-butynyl, 3-butynyl), pentynyl (e.g., 2-pentynyl, 3-pentynyl, 4-pentynyl), 1-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, hexynyl (e.g., 2-hexynyl, 5-hexynyl), 1-ethyl-3-butynyl, heptynyl (e.g., 2-heptynyl, 6- alkynyl groups such as 1-octynyl, 2-octynyl, 7-octynyl, nonynyl (e.g., 2-nonynyl, 8-nonynyl), decynyl (e.g., 2-decynyl, 9-decynyl), undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecinyl, octadecynyl, nonadecinyl, and eicosynyl; etc.

[0067] The saturated chain hydrocarbon group (ie, linear alkyl group or branched alkyl group) preferably has 1 to 10 carbon atoms, more preferably 1 to 7 carbon atoms, and even more preferably 1 to 5 carbon atoms.

[0068] The unsaturated chain hydrocarbon group (ie, alkenyl group, alkynyl group) preferably has 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 8 carbon atoms.

[0069] Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl. cycloalkyl groups such as 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl;

[0070] Cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl;

[0071] Saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl; etc.

[0072] The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 10 carbon atoms.

[0073] Examples of the aromatic hydrocarbon group include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di-tert-butylphenyl, 3,5-di-tert-butyl-4-methylphenyl, 4-n-butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl, Base and pyrene base, etc.

[0074] The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-20, more preferably 6-10, and even more preferably 6-8.

[0075] R 13 and R 14 The hydrocarbon group represented by may be a group formed by combining the above-mentioned hydrocarbon groups (e.g., an aromatic hydrocarbon group and at least one of a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group) as long as the total number of carbon atoms is 20 or less, and examples thereof include:

[0076] Aralkyl groups such as benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 1,1-diphenylethyl, (1-naphthyl)methyl and (2-naphthyl)methyl;

[0077] Aroylene groups such as 1-phenylvinyl, 2-phenylvinyl (phenylvinyl), 2,2-diphenylvinyl, and 2-phenyl-2-(1-naphthyl)vinyl;

[0078] Aroalkynyl groups such as phenylethynyl and 3-phenyl-2-propynyl;

[0079] Phenyl groups having one or more phenyl groups bonded thereto, such as biphenyl and terphenyl;

[0080] Cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, and the like.

[0081] The number of carbon atoms in these compounds is preferably 7-18, more preferably 7-15.

[0082] R 13 and R 14 Among the hydrocarbon groups represented by, as a group composed of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), for example, alkyl groups bonded with one or more alicyclic hydrocarbon groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl, and adamantylmethyl may be used. The number of carbon atoms is preferably 4 to 15, and more preferably 4 to 10.

[0083] R 13 and R 14 The hydrocarbon group having 1 to 20 carbon atoms represented by may have a substituent. Examples of the substituent include a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a2 wait.

[0084] Here, R a1 and R a2 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. a1 and R a2 The hydrocarbon group having 1 to 20 carbon atoms represented by 13 and R 14 The same groups are represented by the hydrocarbon groups having 1 to 20 carbon atoms.

[0085] As R 13 and R 14 The heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by may be a monocyclic or polycyclic group, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0086] Examples of the heterocycle containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; monocyclic unsaturated heterocycles such as five-membered unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole; and six-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine and 1,3,5-triazine; condensed bicyclic heterocycles such as indazole, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole and benzopiperidine; and condensed tricyclic heterocycles such as carbazole, acridine and phenazine.

[0087] Examples of the heterocyclic ring containing only oxygen atoms as heteroatoms include ethylene oxide, oxetane, tetrahydrofuran, tetrahydropyran, Alkane, 1,4-di alkane and other monocyclic saturated heterocycles; furan and other five-membered unsaturated heterocycles, 2H-pyran, 4H-pyran and other six-membered unsaturated heterocycles; α-acetolactone, β-propiolactone, γ-butyrolactone, δ-valerolactone and other lactone heterocycles; 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane and other bicyclic saturated heterocycles; 1-benzofuran, benzopyran, benzodione Condensed bicyclic heterocycles such as chrysene, chroman, and isochroman; Condensed tricyclic heterocycles such as xanthene and dibenzofuran; etc.

[0088] Examples of the heterocycle containing only a sulfur atom as a heteroatom include a five-membered saturated heterocycle such as dithiolane, a monocyclic saturated heterocycle such as a six-membered saturated heterocycle such as thiazane and 1,3-dithiane; a five-membered unsaturated heterocycle such as thiophene, a monocyclic unsaturated heterocycle such as a six-membered unsaturated heterocycle such as 4H-thiopyran; a condensed bicyclic heterocycle such as benzothiopyran and benzothiophene; and a condensed tricyclic heterocycle such as thianthrene and dibenzothiophene.

[0089] Examples of the heterocycle containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, and 2-piperidone; Azoles, Iso Monocyclic unsaturated heterocyclic rings such as azoles; benzo Azoles, Benziso Azoles, benzo Azine, benzodioxadiazine Alkane, benzimidazolinium and other fused bicyclic heterocyclic rings; phenanthracene Oxazine and other fused tricyclic heterocyclic rings; etc.

[0090] Examples of the heterocycle containing a nitrogen atom and a sulfur atom as a heteroatom include a monocyclic unsaturated heterocycle such as thiazole; a condensed bicyclic heterocycle such as benzothiazole; and a condensed tricyclic heterocycle such as phenothiazine.

[0091] In addition, the bonding site of the heterocyclic ring is the part after any hydrogen atom contained in each ring leaves.

[0092] The heterocyclic group has preferably 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and even more preferably 3 to 20 carbon atoms.

[0093] The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a2 etc. (Among which, R a1 and R a2 Same as above).

[0094] For R 3 ~R 12 The halogen atom represented by R 13 and R 14 Examples of the halogen atom as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by and the halogen atom as a substituent of the above-mentioned heterocyclic group include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0095] R 1 and R 2 At least one of them indicates -R 13 or -O-R 13 In the case of R 1 and R 2 They may bond to each other to form a ring. 1 and R 2 Examples of the ring formed by mutual bonding include groups represented by formulae (cy1) to (cy6).

[0096]

[0097] [Where R 15 ~R 20 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent. * represents a bonding site.]

[0098] As R 15 ~R 20 The hydrocarbon group having 1 to 8 carbon atoms which may have a substituent may be represented by 13 and R 14 The hydrocarbon group having 1 to 20 carbon atoms which may have a substituent is a group in which the hydrocarbon group in the groups described above has 1 to 8 carbon atoms.

[0099] R 15 ~R 20 As each independently, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an alkenyl group having 1 to 8 carbon atoms which may have a substituent is preferred.

[0100] As R 1 and R 2 Represented by -R 13 AND-O-R 13 R 13 ,

[0101] Preferably, the aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, the aliphatic saturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent (i.e., a linear alkyl group, a branched alkyl group, or a cycloalkyl group), the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent (i.e., an alkenyl group, an alkynyl group, or an unsaturated alicyclic hydrocarbon group), the arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or the arylalkynyl group having 8 to 20 carbon atoms which may have a substituent,

[0102] More preferably, it is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent (i.e., an alkenyl group, an alkynyl group, or an unsaturated alicyclic hydrocarbon group), an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent,

[0103] More preferred are an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent and an alkynyl group having 2 to 20 carbon atoms which may have a substituent.

[0104] As R 1 , preferably -R 13 or -O-R 13 And the above R 13 In the form of an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a linear or branched alkyl group having 2 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 20 carbon atoms which may have a substituent, an alkynyl group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent.

[0105] In particular, as R 1 , preferably -R 13 or -O-R 13 And the above R 13 is a group containing an unsaturated chain hydrocarbon group, specifically,

[0106] More preferably -R 13 or -O-R 13 And the above R 13 In the embodiment of an alkenyl group having 2 to 20 carbon atoms which may have a substituent, an alkynyl group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent,

[0107] More preferably, -R 13 or -O-R 13 And the above R 13 In the embodiment of an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 12 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 12 carbon atoms which may have a substituent,

[0108] Especially preferably -R 13 or -O-R 13 And the above R 13 This is an embodiment of an alkynyl group having 2 to 10 carbon atoms which may have a substituent.

[0109] As R 2 , preferably -R 13 or -O-R 13 And the above R 13 In the form of an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a linear or branched alkyl group having 2 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 20 carbon atoms which may have a substituent, an alkynyl group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent.

[0110] In particular, as R 2 , preferably -R 13 or -O-R 13 And the above R 13 is a group containing an unsaturated chain hydrocarbon group or an aromatic hydrocarbon group which may have a substituent, specifically,

[0111] More preferably -R 13 or -O-R 13 And the above R13 In the embodiment of an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an alkenyl group having 2 to 20 carbon atoms which may have a substituent, an alkynyl group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent,

[0112] More preferably, -R 13 or -O-R 13 And the above R 13 In the embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 12 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 12 carbon atoms which may have a substituent,

[0113] Especially preferably -R 13 or -O-R 13 And the above R 13 In the embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or an alkynyl group having 2 to 10 carbon atoms which may have a substituent.

[0114] As R 3 ~R 12 Represented by -R 13 AND-O-R 13 R 13 , preferably a straight-chain or branched alkyl group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a straight-chain or branched alkyl group having 1 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, further preferably a straight-chain or branched alkyl group having 1 to 5 carbon atoms.

[0115] AS-S-R 13 R 13 , preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a linear or branched alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0116] R 14 Preferred are hydrogen atoms, linear or branched alkyl groups having 1 to 10 carbon atoms, or aromatic hydrocarbon groups having 6 to 12 carbon atoms, and more preferred are hydrogen atoms, linear or branched alkyl groups having 1 to 4 carbon atoms, or aromatic hydrocarbon groups having 6 to 10 carbon atoms.

[0117] R a1 and R a2Each independently is preferably a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferably a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0118] As R in formula (T-1) 3 ~R 6 , each independently preferably a hydrogen atom, -R 13 , or a halogen atom, more preferably a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom, further preferably a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a halogen atom, particularly preferably a hydrogen atom, a tert-butyl group, a phenyl group, a fluorine atom, a chlorine atom or a bromine atom.

[0119] Among them, R is preferred 3 ~R 6 Each of R is independently a hydrogen atom or a halogen atom; 4 or R 5 For -R 13 (preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms) or a halogen atom, and the remainder is hydrogen atoms; R 4 and R 5 For -R 13 (preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms) or a halogen atom and R 3 and R 6 For hydrogen atoms.

[0120] Examples of the group represented by formula (T-1) include groups represented by formulas (t1-1) to (t1-11), and groups represented by formulas (t1-1) to (t1-9) are preferred. In the formula, n represents an integer of 1 to 3, and * represents a bonding site to the pyrrole ring.

[0121]

[0122] As R in formula (T-2) 7 ~R 12 , each independently preferably a hydrogen atom, -R 13or a halogen atom, more preferably a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom, further preferably a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a halogen atom, particularly preferably a hydrogen atom, a tert-butyl group, a phenyl group, a fluorine atom, a chlorine atom or a bromine atom.

[0123] Among them, R is preferred 7 ~R 12 Each of R is independently a hydrogen atom or a halogen atom; 10 or R 11 For -R 13 (preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms) or a halogen atom, and the remainder is hydrogen atoms; R 10 and R 11 For -R 13 (preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms) or a halogen atom and R 7 ~R 9 and R 12 For the hydrogen atom.

[0124] Examples of the group represented by formula (T-2) include groups represented by formulas (t2-1) to (t2-11), and groups represented by formulas (t2-1) to (t2-9) are preferred. In the formula, m represents an integer of 1 to 5, and * represents a bonding site to the pyrrole ring.

[0125]

[0126] When the compound represented by formula (I) has a plurality of groups represented by formula (T-1), the groups represented by the plurality of formula (T-1) may be the same or different, and are preferably the same. In addition, when the colorant contains two or more compounds represented by formula (I), the groups represented by formula (T-1) between the compounds may be the same or different, and are preferably the same.

[0127] When the compound represented by formula (I) has a plurality of groups represented by formula (T-2), the groups represented by the plurality of formula (T-2) may be the same or different, and are preferably the same. In addition, when the colorant contains two or more compounds represented by formula (I), the groups represented by formula (T-2) between the compounds may be the same or different, and are preferably the same.

[0128] From the viewpoint of further improving the green spectrum characteristics of the obtained coating film, the compound represented by formula (I) preferably has a halogen atom, more preferably has a bromine atom and / or a fluorine atom, and further preferably has a bromine atom. It should be noted that all the compounds represented by formula (I) contained in the colorant of the present invention do not need to have a halogen atom, as long as at least one compound represented by formula (I) has a halogen atom. The number of halogen atoms (preferably the total number of bromine atoms and fluorine atoms) possessed by the compound represented by formula (I) in the colorant of the present invention is preferably 0.2 to 8, more preferably 0.5 to 6, and further preferably 1 to 5 relative to the number of Al atoms possessed by the compound represented by formula (I). It should be noted that the substitution position of the above-mentioned halogen atom (preferably a bromine atom and / or a fluorine atom) is not particularly limited, and preferably ring T 1 ~Ring T 4 At least one of them has a halogen atom (preferably a bromine atom and / or a fluorine atom), and more preferably R 3 ~R 12 At least one of them is a halogen atom (preferably a bromine atom or a fluorine atom).

[0129] The compound represented by the formula (I) is preferably a compound represented by the following formula (I-i).

[0130]

[0131] [In formula (I-i),

[0132] R 1a Represents - R 21 or -O-R 21 , R 21 It represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an aliphatic saturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent.

[0133] R 2a Represents - R 22 or -O-R 22 , R 22 It represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an aliphatic saturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 20 carbon atoms which may have a substituent.

[0134] Ring T 1a , Ring T 2a , Ring T3a and Ring T 4a Each independently represents a group represented by formula (T-1a) or formula (T-2a).]

[0135]

[0136] [In formula (T-1a), R 3a ~R 6a Each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom. * represents a bonding site to the pyrrole ring.]

[0137]

[0138] [In formula (T-2a), R 7a ~R 12a Each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom. * represents a bonding site to the pyrrole ring.]

[0139] As R 21 ~R 22 The aliphatic saturated hydrocarbon group having 2 to 20 carbon atoms represented by R includes the groups explained as the above-mentioned linear alkyl group, branched alkyl group and cycloalkyl group. 21 and R 22 The aliphatic saturated hydrocarbon group represented by is preferably 2-15, more preferably 2-10, and even more preferably 2-7.

[0140] As R 21 ~R 22 The aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R includes the groups explained as the alkenyl group, alkynyl group and unsaturated alicyclic hydrocarbon group. 21 and R 22 The aliphatic unsaturated hydrocarbon group represented by is preferably 2-15, more preferably 2-10, and even more preferably 2-7.

[0141] As R 21 ~R 22 Examples of the arylalkenyl group having 8 to 20 carbon atoms and the arylalkynyl group having 8 to 20 carbon atoms include the groups described above as the arylalkenyl group and the arylalkynyl group. The number of carbon atoms in these groups is preferably 7 to 18, and more preferably 7 to 15.

[0142] As R 21 ~R 22 The aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R includes the groups explained as the above-mentioned aromatic hydrocarbon groups. 21 and R 22The number of carbon atoms of the aromatic hydrocarbon group represented by is preferably 6-10, more preferably 6-8.

[0143] As R 21 ~R 22 The substituents that the aromatic hydrocarbon group having 6 to 20 carbon atoms, the aliphatic saturated hydrocarbon group having 2 to 20 carbon atoms, the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms, the arylalkenyl group having 8 to 20 carbon atoms, and the arylalkynyl group having 8 to 20 carbon atoms represented by the present invention may have include: 13 and R 14 The substituents which the hydrocarbon group having 1 to 20 carbon atoms represented may have are the groups described above.

[0144] As R 3a ~R 12a Examples of the alkyl group having 1 to 10 carbon atoms represented by alkyl include groups having 1 to 10 carbon atoms among the groups explained as the above-mentioned linear alkyl group and branched alkyl group.

[0145] As R 3a ~R 12a Examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms represented by include groups having 6 to 12 carbon atoms among the groups explained as the above-mentioned aromatic hydrocarbon groups.

[0146] As R 3a ~R 12a Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, a fluorine atom, a chlorine atom and a bromine atom are preferred.

[0147] As R 1a ,

[0148] Preferably -R 21 or -O-R 21 And the above R 21 In the embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, a linear or branched alkyl group having 2 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 15 carbon atoms which may have a substituent, an alkynyl group having 2 to 15 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 18 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 18 carbon atoms which may have a substituent,

[0149] More preferably -R 21 or -O-R 21 And the above R 21 In the embodiment of an alkenyl group having 2 to 15 carbon atoms which may have a substituent, an alkynyl group having 2 to 15 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 18 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 18 carbon atoms which may have a substituent,

[0150] More preferably, -R 21 or -O-R 21 And the above R 21 In the embodiment of an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 15 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 15 carbon atoms which may have a substituent,

[0151] In particular, any one of the groups represented by the formulae (i-1) to (i-22) and (ii-1) to (ii-22) described below is preferred.

[0152] In addition, -R is also preferred 21 or -O-R 21 And the above R 21 This is an embodiment of an alkynyl group having 2 to 10 carbon atoms which may have a substituent.

[0153] As R 2a ,

[0154] Preferably -R 22 or -O-R 22 And the above R 22 In the embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, a linear or branched alkyl group having 2 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 15 carbon atoms which may have a substituent, an alkynyl group having 2 to 15 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 18 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 18 carbon atoms which may have a substituent,

[0155] More preferably, -R 22 or -O-R 22 And the above R 22 In the embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 15 carbon atoms which may have a substituent, an alkynyl group having 2 to 15 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 18 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 18 carbon atoms which may have a substituent,

[0156] More preferably, -R 22 or -O-R 22 And the above R 22 In the embodiment of an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 15 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 15 carbon atoms which may have a substituent,

[0157] Particularly preferred are any of the groups represented by formula (i-1) to formula (i-22), formula (ii-1) to formula (ii-22), and formula (iii-1) to formula (iii-2) described below.

[0158] In addition, -R is also preferred 22 or -O-R 22 And the above R 22 The embodiment is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent or an alkynyl group having 2 to 10 carbon atoms which may have a substituent.

[0159] In particular, R 1a For-O-R 21 When R 2a ,

[0160] Preferably -R 22 And the above R 22 is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent; or -O-R 22 And the above R 22 In the embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, an alkenyl group having 2 to 15 carbon atoms which may have a substituent, an alkynyl group having 2 to 15 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 18 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 18 carbon atoms which may have a substituent,

[0161] More preferably -O-R 22 And the above R 22 In the form of an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an arylalkenyl group having 8 to 15 carbon atoms which may have a substituent, or an arylalkynyl group having 8 to 15 carbon atoms which may have a substituent.

[0162] In addition, R 1a For -R 21 When R 2a ,

[0163] Preferably -R 22 And the above R 22 This is an embodiment of an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent.

[0164] As R 3a ~R 12a , each independently preferably is a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or a halogen atom, and more preferably is a hydrogen atom, a tert-butyl group, a fluorine atom, a chlorine atom or a bromine atom.

[0165] Among them, as a group represented by formula (T-1a),

[0166] Preferred R 3a ~R 6a Each of R is independently a hydrogen atom or a halogen atom; 4a or R 5a An embodiment in which R is an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom and the remainder is hydrogen atoms; 4a and R 5a is an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom, and R 3a and R 6a For hydrogen atoms,

[0167] More preferably, it is any one of the groups represented by the above formulae (t1-1) to (t1-11),

[0168] More preferably, it is any one of the groups represented by the above formulae (t1-1) to (t1-9).

[0169] In addition, as a group represented by formula (T-2a),

[0170] Preferred R 7a ~R 12a Each of R is independently a hydrogen atom or a halogen atom; 10a or R 11a An embodiment in which R is an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom and the remainder is hydrogen atoms; 10a and R 11a is an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a halogen atom, and R 7a ~R 9a and R 12 For hydrogen atoms,

[0171] More preferably, it is any one of the groups represented by the above formulae (t2-1) to (t2-11),

[0172] More preferably, it is any one of the groups represented by the above formulae (t2-1) to (t2-9).

[0173] From the viewpoint of further improving the green spectral characteristics of the obtained coating film, the compound represented by formula (I-i) preferably has a halogen atom, more preferably has a bromine atom and / or a fluorine atom, and even more preferably has a bromine atom. It should be noted that all the compounds represented by formula (I-i) contained in the colorant of the present invention do not need to have a halogen atom, as long as at least one compound represented by formula (I-i) has a halogen atom. The number of halogen atoms (preferably the total number of bromine atoms and fluorine atoms) possessed by the compound represented by formula (I-i) in the colorant of the present invention is preferably 0.2 to 8, more preferably 0.5 to 6, and even more preferably 1 to 5 relative to the number of Al atoms possessed by the compound represented by formula (I-i). It should be noted that the substitution position of the above-mentioned halogen atom (preferably a bromine atom and / or a fluorine atom) is not particularly limited, and preferably ring T 1a ~Ring T 4a At least one of them has a halogen atom (preferably a bromine atom and / or a fluorine atom), and more preferably R 3a ~R 12a Any one or more of them is a halogen atom (preferably a bromine atom or a fluorine atom).

[0174] Specific examples of the compound represented by formula (I) include compounds represented by the following formulas (Ia-1) to (Ia-11), (Ib-1) to (Ib-22), (Ic-1) to (Ic-22), (Id-1) to (Id-22), (Ie-1) to (Ie-22), (If-1) to (If-7): 1 and R 2 The compound is any one of Nos. 1 to 88 described in Table 1. In the formula, n represents an integer of 1 to 3.

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190] [Table 1]

[0191]

[0192] In Table 1, i-1 to i-22 represent groups represented by the following formulae (i-1) to (i-22), ii-1 to ii-22 represent groups represented by the following formulae (ii-1) to (ii-22), and iii-1 to iii-2 represent groups represented by the following formulae (iii-1) to (iii-2), respectively.

[0193] In the following formula, * to the phosphorus atom represents a bonding site.

[0194]

[0195] The compound represented by formula (I) can be produced, for example, by the following method. That is, aluminum halide is reacted appropriately with a compound represented by formula (t1a) and / or a compound represented by formula (t2a) to synthesize a compound represented by formula (I') (hereinafter, sometimes referred to as compound (I').), and then the obtained compound (I') is reacted appropriately with a compound represented by formula (p1), thereby synthesizing compound (I).

[0196]

[0197] [Where R 1 ~R 12 and Ring T 1 ~Ring T 4 represents the same meaning as above. X represents a halogen atom.]

[0198] Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, a chlorine atom is preferred.

[0199] Alternatively, the compound represented by formula (I) can be synthesized by appropriately reacting aluminum halide, urea, and the compound represented by formula (t1b) and / or the compound represented by formula (t2b) to synthesize compound (I'), and then appropriately reacting the obtained compound (I') with a compound represented by formula (p1).

[0200]

[0201] [Where R 1 ~R 12 , Ring T 1 ~Ring T 4 and X represent the same meanings as above.]

[0202] In the above-mentioned synthesis method, by using only the compound represented by formula (t1a) or only the compound represented by formula (t1b), cyclic T 1 ~Ring T 4 On the other hand, in the above-mentioned synthesis method, by using only the compound represented by formula (t2a) or only the compound represented by formula (t2b), cyclic T can be synthesized. 1 ~Ring T 4 A compound whose entire group is represented by formula (T-2) (i.e., compound (If)). In addition, in the above-mentioned synthesis method, a mixture of compound (Ia), compound (Ib), compound (Ic), compound (Id), compound (Ie) and compound (If) can be synthesized by using a compound represented by formula (t1a) and a compound represented by formula (t2a), or by using a compound represented by formula (t1b) and a compound represented by formula (t2b). It should be noted that the ratio of the number of groups represented by formula (T-2) in the colorant to the number of Al atoms possessed by the compound represented by formula (I) can be adjusted by adjusting the usage ratio of the compound represented by formula (t1a) and the compound represented by formula (t2a), and the usage ratio of the compound represented by formula (t1b) and the compound represented by formula (t2b).

[0203] The colorant of the present invention may further contain a colorant different from the compound represented by formula (I) (hereinafter, sometimes referred to as other colorants). The other colorant may be any of a dye and a pigment.

[0204] Examples of the dye include compounds classified as dyes having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (published by Seishen Co., Ltd.).

[0205] As the dye, for example, an azo dye, a cyanine dye, a triphenylmethane dye, a xanthene dye, a thiazole dye, As the oxazine dye, quinophthalone dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline dye, nitro dye and the like, known dyes are used.

[0206] Specific examples of the dye include CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only the number is described. The same applies to others), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 99, 117, 162, 163, 167, and 189;

[0207] CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0208] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0209] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0210] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0211] CI solvent dyes such as CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0212] CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 156 7, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0213] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 51, 52, 57, 66, 73, 76, 80, 87, 88, 92, 94, 97, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 1 95, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426;

[0214] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0215] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0216] CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120 , 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;

[0217] CI acid green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109 and other CI acid dyes;

[0218] CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;

[0219] CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

[0220] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0221] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0222] CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 190, 192, 193, 194, 195, 196, 198, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

[0223] CI direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82;

[0224] CI Disperse Yellow 51, 54, 76;

[0225] CI Disperse Violet 26, 27;

[0226] CI disperse dyes such as CI disperse blue 1, 14, 56, 60;

[0227] CI basic blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;

[0228] CI Basic Violet 2, 10, 11;

[0229] CI Basic Red 1, 2, 3, 4, 8, 9, 10, 11;

[0230] CI Basic Green 1; etc. CI basic dyes;

[0231] CI Reactive Yellow 2, 76, 116;

[0232] CI Reactive Orange 16;

[0233] CI Reactive Red 36; etc. CI Reactive Dyes,

[0234] CI Medium Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0235] CI Medium Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

[0236] CI Medium Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0237] CI medium violet 1, 1: 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

[0238] CI Medium Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 83, 84;

[0239] CI mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other CI mordant dyes,

[0240] CI vat dyes such as CI vat green 1, etc.

[0241] These dyes may be used alone or in combination for each color.

[0242] Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and the following pigments can be exemplified.

[0243] Green pigment: CI Pigment Green 7, 36, 58, etc.

[0244] Yellow pigment: CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.

[0245] Orange pigment: CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.

[0246] Red pigment: CI Pigment Red 9, 97, 105, 122, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 242, 254, 255, 264, 265, 291, etc.

[0247] Blue pigment: CI Pigment Blue 15, 15:3, 15:4, 15:6, 16, 60, etc.

[0248] Purple pigment: CI pigment violet 19, 23, 29, 32, 36, 38, etc.

[0249] These pigments may be used alone or in combination for each color.

[0250] The pigment may be subjected to the following treatments as required: rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, grafting treatment on the pigment surface using a polymer compound, micronization treatment using a sulfuric acid micronization method, washing treatment using an organic solvent, water, etc. to remove impurities, removal treatment using an ion exchange method for ionic impurities, etc. The particle size of the pigment is preferably substantially uniform.

[0251] The content of the compound represented by formula (I) is preferably 5 to 100% by mass, more preferably 10 to 95% by mass, and even more preferably 15 to 90% by mass in the total amount of the colorant.

[0252] <<Colored resin composition>>

[0253] The present invention includes a colored resin composition containing the above-mentioned colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), and a solvent (hereinafter, sometimes referred to as solvent (E)).

[0254] The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).

[0255] The colored resin composition of the present invention may contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

[0256] In the present specification, the compounds exemplified as the components may be used alone or in combination of two or more unless otherwise specified.

[0257] <Colorant (A)>

[0258] The colorant (A) is the same as the above-mentioned colorant, and preferred embodiments thereof are also the same.

[0259] The content of the compound represented by formula (I) is preferably 0.5 to 70% by mass, more preferably 1 to 55% by mass, further preferably 2 to 50% by mass, and particularly preferably 8 to 40% by mass in the total solid content of the colored resin composition. This can further improve the green spectrum characteristics and light resistance of the resulting coating film.

[0260] In this specification, the "total amount of solid content" refers to the total amount of components obtained by removing the solvent from the colored resin composition of the present invention. The total amount of solid content and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography and gas chromatography.

[0261] The content of the colorant (A) is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, further preferably 2 to 55% by mass, and particularly preferably 8 to 50% by mass in the total amount of the solid content of the colored resin composition. When the content of the colorant (A) is within the above range, a desired spectrum and color density can be easily obtained.

[0262] <Resin (B)>

[0263] The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

[0264] Resin [K1]: a copolymer of at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");

[0265] Resin [K2]: a copolymer of (a), (b), and a monomer (c) copolymerizable with (a) (which is different from (a) and (b) (hereinafter sometimes referred to as "(c)");

[0266] Resin [K3]: a copolymer of (a) and (c);

[0267] Resin [K4]: a resin obtained by reacting a copolymer of (a) and (c) with (b);

[0268] Resin [K5]: a resin obtained by reacting a copolymer of (b) and (c) with (a);

[0269] Resin [K6]: A resin obtained by reacting a copolymer of (b) and (c) with (a), and further reacting the copolymer with a polycarboxylic acid and / or a carboxylic anhydride.

[0270] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid;

[0271] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic acid, etc.;

[0272] Bicyclic unsaturated compounds containing a carboxyl group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;

[0273] Unsaturated dicarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

[0274] Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate;

[0275] Unsaturated acrylic acid esters containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid, etc.

[0276] Among them, acrylic acid, methacrylic acid, maleic anhydride and the like are preferred from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

[0277] (b) refers to a polymerizable compound having, for example, a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) Preferably, the monomer has a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0278] In addition, in this specification, "(meth)acrylic acid" means at least one selected from acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0279] As (b), for example, there can be mentioned a monomer (b1) having an ethylene oxide group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like.

[0280] Examples of (b1) include a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)") and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

[0281] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, α-methyl-o-vinyl benzyl glycidyl ether, α-methyl-m-vinyl benzyl glycidyl ether, α-methyl-p-vinyl benzyl glycidyl ether, 2,3-bis(glycidyl)acrylate, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.

[0282] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), 3,4-epoxytricyclo[5.2.1.0](meth)acrylate, and 3,4-epoxytricyclo[5.2.1.0](meth)acrylate. 2,6 ]decyl ester, a compound represented by formula (R1) and a compound represented by formula (R2), etc.

[0283]

[0284] [In formula (R1) and formula (R2), R ra and R rb It represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group.

[0285] X ra and X rb Indicates a single bond, *-R rc -, * - R rc -O-, *-R rc -S- or *-R rc -NH-.

[0286] R rc It represents an alkanediyl group having 1 to 6 carbon atoms.

[0287] * indicates the bonding site with O. ]

[0288] Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.

[0289] Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl and 4-hydroxybutyl.

[0290] As R ra and R rb , preferably, a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are mentioned, and more preferably, a hydrogen atom and a methyl group are mentioned.

[0291] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

[0292] As X ra and X rb , preferably a single bond, a methylene group, an ethylene group, *-CH 2 -O- and *-CH 2 CH 2 -O-, more preferably a single bond, *-CH 2 CH 2 -O- (* indicates the bonding site with O).

[0293] Examples of the compound represented by formula (R1) include compounds represented by any one of formula (R1-1) to formula (R1-15). Among them, compounds represented by formula (R1-1), formula (R1-3), formula (R1-5), formula (R1-7), formula (R1-9) or formula (R1-11) to formula (R1-15) are preferred, and compounds represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15) are more preferred.

[0294]

[0295]

[0296] Examples of the compound represented by formula (R2) include compounds represented by any one of formula (R2-1) to formula (R2-15). Among them, compounds represented by formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9) or formula (R2-11) to formula (R2-15) are preferred, and compounds represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15) are more preferred.

[0297]

[0298] As (b2), a monomer having an oxetane group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane.

[0299] As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0300] As (b), (b1) is preferred because the reliability of the obtained color filter, such as heat resistance and chemical resistance, can be further improved. Moreover, (b1-2) is more preferred because the storage stability of the colored resin composition is excellent.

[0301] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0](meth)acrylate, 2,6 ] decane-8-yl ester (in the technical field, it is commonly known as "dicyclopentyl (meth)acrylate". It is also sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 (Meth)acrylates such as decen-8-yl ester (in the technical field, it is commonly referred to as "dicyclopentenyl (meth)acrylate"), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0302] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0303] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0304] Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxy Bicyclic unsaturated compounds such as bicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0305] Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;

[0306] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0307] As (c), 2-ethylhexyl (meth)acrylate, dicyclopentyl (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are preferred, and styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are more preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0308] In resin [K1], the ratio of the structural units derived from each unit is preferably 2 to 60 mol% of the structural units derived from (a) and 40 to 98 mol% of the structural units derived from (b), and more preferably 10 to 50 mol% of the structural units derived from (a) and 50 to 90 mol% of the structural units derived from (b), among all the structural units constituting resin [K1].

[0309] When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be excellent.

[0310] The resin [K1] can be produced, for example, by referring to the method described in the document "Experimental Methods for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd., Chemical Dojin, 1st edition, 1st printing, published on March 1, 1972) and the cited documents described in the document.

[0311] Specifically, the following method can be cited: a predetermined amount of (a) and (b), a polymerization initiator, and a solvent are placed in a reaction container, and a deoxygenated atmosphere is formed by replacing oxygen with nitrogen, for example, and heating and heat preservation are performed while stirring. It should be noted that the polymerization initiator and solvent used here are not particularly limited, and polymerization initiators and solvents commonly used in this field can be used. For example, as polymerization initiators, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile) and organic peroxides (benzoyl peroxide and the like) are cited. As solvents, any solvent that dissolves each monomer is sufficient. As solvent (E), the solvents described below and the like can be cited.

[0312] It should be noted that the obtained copolymer may be used as a solution after the reaction, a concentrated or diluted solution, or a substance taken out in a solid (powder) form by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition as a solvent during the polymerization, the solution after the reaction can be used directly for preparing the colored resin composition, so the production process of the colored resin composition can be simplified.

[0313] In resin [K2], the ratio of the structural unit derived from each unit is preferably 2 to 45 mol% of the structural unit derived from (a), 2 to 95 mol% of the structural unit derived from (b), and 1 to 65 mol% of the structural unit derived from (c), among all the structural units constituting resin [K2]. It is more preferred that the structural unit derived from (a) is 5 to 40 mol%, the structural unit derived from (b) is 5 to 80 mol%, and the structural unit derived from (c) is 5 to 60 mol%.

[0314] When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be excellent.

[0315] The resin [K2] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0316] In resin [K3], the ratio of the structural units derived from each unit in all the structural units constituting resin [K3] is preferably 2 to 60 mol% for the structural units derived from (a) and 40 to 98 mol% for the structural units derived from (c), and more preferably 10 to 50 mol% for the structural units derived from (a) and 50 to 90 mol% for the structural units derived from (c).

[0317] The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0318] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic anhydride contained in (a).

[0319] First, a copolymer of (a) and (c) is produced in the same manner as described as the method for producing resin [K1]. In this case, the ratio of the structural units derived from each unit is preferably the same ratio as that exemplified in resin [K3].

[0320] Next, the cyclic ether having 2 to 4 carbon atoms contained in (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the above copolymer.

[0321] After the copolymer of (a) and (c) is produced, the atmosphere in the flask is replaced from nitrogen to air, (b), a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in the flask, and the mixture is reacted at, for example, 60 to 130° C. for 1 to 10 hours, thereby producing resin [K4].

[0322] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). Within this range, there is a tendency for the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern to become good. Since the reactivity of cyclic ethers is high, it is not easy for unreacted (b) to remain. Therefore, as (b) used in resin [K4], (b1) is preferred, and (b1-1) is more preferred.

[0323] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c).

[0324] The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the heat generated by the polymerization, etc. It should be noted that the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the heat generated by the polymerization, etc., similarly to the polymerization conditions.

[0325] As for resin [K5], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as in the production method of resin [K1]. As in the above, the obtained copolymer may be used directly as a solution after the reaction, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) obtained by a method such as reprecipitation.

[0326] The ratio of the structural units derived from (b) and (c) to the total molar number of all structural units constituting the above-mentioned copolymer is preferably 5 to 95 mol% for the structural units derived from (b) and 5 to 95 mol% for the structural units derived from (c), and more preferably 10 to 90 mol% for the structural units derived from (b) and 10 to 90 mol% for the structural units derived from (c).

[0327] Furthermore, resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride contained in (a) with the cyclic ether derived from (b) contained in the copolymer of (b) and (c) under the same conditions as those in the method for producing resin [K4].

[0328] The amount of (a) to be reacted with the copolymer is preferably 5 to 100 mol per 100 mol of (b). Since cyclic ethers have high reactivity and unreacted (b) is less likely to remain, (b1) is preferably used as (b1-1), and more preferably (b1-1) as (b) in the resin [K5].

[0329] The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic anhydride. The carboxylic anhydride is reacted with the hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic anhydride.

[0330] Examples of the carboxylic anhydride include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic anhydride used is preferably 0.1 to 1 mol relative to 1 mol of the amount of (a) used.

[0331] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid copolymer resin [K1]; acrylic acid 3,4-epoxy tricyclic [5.2.1.0 2,6 ]decyl ester / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; resins obtained by adding benzyl (meth)acrylate / (meth)acrylic acid copolymer to glycidyl (meth)acrylate, resins obtained by adding tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer to glycidyl (meth)acrylate, resins obtained by adding tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer to glycidyl (meth)acrylate, Resins such as resins obtained by addition of oil esters [K4]; resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid, etc. [K5]; resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and further reacting with tetrahydrophthalic anhydride, resins obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate / dicyclopentanyl (meth)acrylate with (meth)acrylic acid and further reacting with succinic anhydride, etc. [K6], etc.

[0332] Among them, as resin (B), a copolymer (resin [K1] or resin [K2]) or resin [K6] containing a structural unit derived from at least one selected from unsaturated carboxylic acid and unsaturated carboxylic anhydride, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond is preferred, and resin [K1] or resin [K2] is more preferred.

[0333] The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 500 to 100000, more preferably 600 to 50000, and even more preferably 700 to 30000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

[0334] The dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1-6, more preferably 1.2-4.

[0335] The acid value of the resin (B) is preferably 10 to 170 mg-KOH / g, more preferably 20 to 150 mg-KOH / g, and further preferably 30 to 135 mg-KOH / g, based on solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration using a potassium hydroxide aqueous solution.

[0336] The content of the resin (B) is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, further preferably 17 to 70% by mass, and further preferably 17 to 55% by mass relative to the total solid content of the colored resin composition. When the content of the resin (B) is within the above range, a colored pattern can be formed, and there is a tendency for the resolution and residual film rate of the colored pattern to be improved.

[0337] The content of the colorant (A) relative to 100 parts by mass of the resin (B) is preferably 1 to 100 parts by mass, more preferably 8 to 70 parts by mass, and even more preferably 15 to 50 parts by mass.

[0338] <Polymerizable compound (C)>

[0339] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylate compounds.

[0340] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0341] Among them, it is preferred that at least one selected from trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate be contained, and it is more preferred that at least one selected from trimethylolpropane triacrylate, dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate be contained.

[0342] The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0343] The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass relative to the total amount of the solid content of the colored resin composition. When the content of the polymerizable compound (C) is within the above range, there is a tendency for the residual film rate during color pattern formation and the chemical resistance of the optical filter to be improved.

[0344] <Polymerization initiator (D)>

[0345] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. under the action of light or heat to initiate polymerization, and a known polymerization initiator can be used.

[0346] Examples of the polymerization initiator that generates active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0347] The O-acyl oxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bonding site.

[0348]

[0349] Examples of the O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethoxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, alkyl-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[4-(2-hydroxyethoxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, and the like. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (all manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) may also be used. Among them, the O-acyl oxime compound is preferably selected from N-acetoxy-1-[4-(2-hydroxyethoxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, At least one selected from the group consisting of N-acetoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably at least one selected from the group consisting of N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, and N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine. When these O-acyl oxime compounds are used, there is a tendency that a color filter with high brightness can be obtained.

[0350] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

[0351]

[0352] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

[0353] Examples of the compound having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzil dimethyl ketal.

[0354] In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0355] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine. [2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, and the like.

[0356] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.

[0357] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open Nos. 6-75372 and 6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole. , 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.), biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with alkoxycarbonyl groups (for example, see Japanese Patent Application Laid-Open No. 7-10913, etc.), etc.

[0358] In addition, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, and titanocene compounds, etc. These are preferably used in combination with the polymerization initiator aid (D1) (particularly amines) described later.

[0359] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, nitrobenzyl toluenesulfonates, and benzoin toluenesulfonates.

[0360] The polymerization initiator (D) preferably contains at least one selected from an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound, and more preferably contains an O-acyloxime compound.

[0361] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten exposure time, thereby improving the productivity of the optical filter.

[0362] <Polymerization initiator aid (D1)>

[0363] The polymerization initiator aid (D1) is a compound or sensitizer for accelerating the polymerization of the polymerizable compound to be polymerized by the polymerization initiator. When the polymerization initiator aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0364] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0365] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Among them, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

[0366] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0367] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0368] Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0369] When these polymerization initiation aids (D1) are used, their content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and there is a tendency for the productivity of the optical filter to be improved.

[0370] <Solvent (E)>

[0371] The solvent (E) is not particularly limited, and a solvent commonly used in this field can be used. For example, ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO- and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. can be mentioned.

[0372] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0373] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole.

[0374] Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0375] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0376] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0377] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0378] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0379] The solvent (E) is preferably at least one selected from ether solvents, ether ester solvents and amide solvents, and more preferably at least one selected from diethylene glycol methyl ethyl ether, propylene glycol monomethyl ether acetate and N-methylpyrrolidone.

[0380] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, relative to the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness during coating becomes good, and the color density is not insufficient when forming an optical filter, so there is a tendency that the display characteristics become good.

[0381] <Leveling agent (F)>

[0382] Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms, etc. These may have a polymerizable group in a side chain.

[0383] Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule, and more specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.).

[0384] Examples of the fluorine-based surfactant include surfactants having a fluorine carbon chain in the molecule. Specifically, examples include FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Laboratories, Ltd.), etc.

[0385] Examples of the above-mentioned organosilicon-based surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, and more specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0386] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass %, more preferably 0.002 to 0.1 mass %, and further preferably 0.005 to 0.05 mass % relative to the total amount of the colored resin composition. It should be noted that the content does not include the content of the pigment dispersant described later. When the content of the leveling agent (F) is within the above range, the flatness of the optical filter can be improved.

[0387] <Other ingredients>

[0388] The colored resin composition may contain additives known in the technical field such as a filler, other polymer compounds, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent, as required.

[0389] <Method for producing colored resin composition>

[0390] The colored resin composition can be prepared by mixing, for example, a colorant (A), a resin (B), a solvent (E), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), a polymerization initiation aid (D1), and other components. The mixed colored resin composition is preferably filtered using a filter having a pore size of about 0.01 to 10 μm.

[0391] The compound represented by formula (I) as the colorant (A) and the pigment used as needed can be dispersed by containing a pigment dispersant to prepare a dispersion in a state of being uniformly dispersed in a dispersant solution. By mixing the remaining components in such a dispersion to reach a predetermined concentration, the target colored resin composition can be prepared. The compound represented by formula (I) and the pigment can be dispersed alone or in a mixture of multiple types.

[0392] As pigment dispersant, surfactant etc. can be enumerated, and can be any one of cationic, anionic, nonionic and amphoteric surfactants. Specifically, surfactants such as polyester, polyamine and acrylic acid can be enumerated. These dispersants can be used alone or in combination of two or more. As dispersant, when represented by trade name, KP (Shin-Etsu Chemical Industry (Strain) system), FLOWLEN (Kyoeisha Chemical (Strain) system), Solsperse (registered trademark) (Zeneca (Strain) system), EFKA (registered trademark) (BASF company system), AJISPER (registered trademark) (Ajinomoto Fine Chemicals (Strain) system), Disperbyk (registered trademark), BYK (registered trademark) (BYK company system) etc. can be enumerated.

[0393] When a pigment dispersant is used, its usage amount is preferably 10 to 200 parts by mass, more preferably 15 to 180 parts by mass, and further preferably 20 to 160 parts by mass, relative to 100 parts by mass of the compound represented by formula (I) and the pigment in the dispersion. When the usage amount of the pigment dispersant is within the above range, there is a tendency to obtain a dispersion in a more uniform dispersed state.

[0394] When the colorant (A) contains a dye, the dye may be dissolved in part or all of the solvent (E) to prepare a solution, and the solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0395] [Color Filter]

[0396] As a method for manufacturing a coloring pattern of a color filter by the colored resin composition of the present invention, photolithography, inkjet method, printing method, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method of applying the above-mentioned colored resin composition to a substrate and drying it to form a composition layer, exposing the composition layer through a photomask and developing it. In the photolithography, a colored coating film as a cured product of the above-mentioned composition layer can be formed without using a photomask and / or developing it during exposure.

[0397] The film thickness of the color filter is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, further preferably 3 μm or less, further preferably 1.5 μm or less, particularly preferably 0.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, further preferably 0.3 μm or more.

[0398] As the substrate, quartz glass, borosilicate glass, aluminosilicate glass, glass plates such as soda-lime glass coated with silicon dioxide on the surface, resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, and substrates on which aluminum, silver, silver / copper / palladium alloy thin films are formed can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates. In addition, a substrate treated with HMDS (1,1,1,3,3,3-hexamethyldisilazane) on a silicon substrate can also be used.

[0399] The formation of each color pixel based on the photolithography method can be carried out using known or customary devices and conditions. For example, it can be produced as described below. First, the colored resin composition is applied to the substrate, and the volatile components such as the solvent are removed and dried to obtain a smooth composition layer. As the coating method, spin coating, slit coating, slit·spin coating, etc. can be cited. The temperature during heating and drying is preferably 30 to 120°C, more preferably 50 to 110°C. In addition, as the heating time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When the reduced pressure drying is carried out, it is preferably carried out at a pressure of 50 to 150Pa and a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.

[0400] Next, the composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target application is used. As the light source used in the exposure, a light source that produces light with a wavelength of 250 to 450 nm is preferably used. For example, light less than 250 nm can be cut off using a filter that cuts off the wavelength region, or light near 436 nm, near 408 nm, and near 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, and halogen lamps can be cited. In order to be able to evenly irradiate parallel light to the entire exposure surface and accurately align the photomask with the substrate, it is preferred to use a reduced projection exposure device or a proximity exposure device such as a mask aligner and a stepper.

[0401] The exposed composition layer is brought into contact with a developer for development to form a colored pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. In addition, the developer may contain a surfactant. The development method may be any one of a puddle method, an immersion method, and a spray method. Furthermore, the substrate is tilted at an arbitrary angle during development.

[0402] After development, water washing is preferably performed.

[0403] The obtained colored pattern is preferably further post-baked. The post-baking temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0404] The colored pattern and colored coating film thus obtained are useful as a color filter, and the color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, etc.), electronic paper, a solid-state imaging element, and the like.

[0405] In particular, the color filter of the present invention improves the green spectral characteristics. For example, in the above-mentioned colored pattern and colored coating film, the distance between the xy chromaticity coordinates in the XYZ colorimetric system of CIE when the converted film thickness is 1.0 μm and the chromaticity coordinates ((x, y) = (0.30, 0.60)) of the vertex of green under the sRGB standard when the converted film thickness is 1.0 μm is as small as possible, and specifically, the distance is preferably 3.3 or less, and more preferably 3.1 or less.

[0406] The transmittance X of the colored pattern and the colored coating film at a wavelength of 570 nm when the film thickness is converted to 1.0 μm is 570 Transmittance X at wavelength 530nm 530 The ratio (X 570 / X 530 ) is as close to 1 as possible. Specifically, the ratio is preferably greater than 0.60, more preferably greater than 0.65.

[0407] Example

[0408] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples, and can certainly be implemented by adding appropriate changes within the scope of the above-mentioned and later-described purport, which are all included in the technical scope of the present invention. It should be noted that, below, "parts" means "parts by mass", and "%" means "% by mass", unless otherwise specified.

[0409] In the following examples, the structures of the compounds were confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.) and / or SEM-EDX measurement (SEM: Helios G4UX (manufactured by FEI), EDX: Ultim Max (manufactured by Oxford Instruments)).

[0410] In the following examples, the ratio of the number of groups represented by formula (T-2) to the number of Al atoms is expressed by 1 The results were confirmed by H-NMR (400 MHz). 1 The measurement conditions of H-NMR (400 MHz) are as follows.

[0411] Measuring device: Varian 400-MR

[0412] Determination solvent: deuterated dimethyl sulfoxide

[0413] Sample concentration: 10mg / 0.6mL

[0414] Measuring temperature: room temperature

[0415] Pulse angle: 45 degrees

[0416] Delay time: 3.5 seconds

[0417] Cumulative times: 1024 times

[0418] Determination basis: Based on (CH 3 ) 2 The chemical shift value of SO proton is 2.5 ppm

[0419] The number of hydrogen atoms in the group represented by formula (T-1) is N1, and 1 The total integrated value of the signal from the hydrogen atom possessed by the group represented by the formula (T-1) contained in the colorant calculated by the H-NMR spectrum is defined as S1, the number of hydrogen atoms possessed by the group represented by the formula (T-2) is defined as N2, and the total integrated value of the signal from the group represented by the formula (T-1) contained in the colorant is defined as S1. 1 The total integrated value of the signal of the hydrogen atom possessed by the group represented by formula (T-2) contained in the colorant calculated by H-NMR spectrum is defined as S2, and the ratio of the number of groups represented by formula (T-2) to the number of Al atoms is calculated based on the following formula (1).

[0420] Formula (1): The ratio of the number of groups represented by formula (T-2) to the number of Al atoms =

[0421] {(S2 / N2) / [(S1 / N1)+(S2 / N2)]}*4

[0422] The integrated value of each signal was calculated by automatically integrating the integrated value using analysis software (Delta 6.0.0 manufactured by JEOL) after setting the integrated range so as to include all peaks belonging to each signal.

[0423] (Synthesis example 1)

[0424] <Preparation of mixture (1)>

[0425] Under nitrogen atmosphere, 20 parts of aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 50 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of 2,3-dicyanonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 69 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 140 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 12 hours. After the reaction liquid was cooled to room temperature, 6.7 parts of aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 23 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the reaction liquid, and the temperature was raised to 150°C and stirred for 23 hours. After the reaction liquid was cooled to room temperature, 840 parts of ethyl acetate were added. The obtained precipitate was obtained as a suction filtration residue, washed with 840 parts of ethyl acetate, and then washed with 1680 parts of ion exchange water. The obtained solid component was dried under reduced pressure at 60°C to obtain 39 parts of a mixture (1). The obtained mixture (1) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (1-a) to (1-f).

[0426]

[0427] <Identification of Compound (1-a)>

[0428] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 574

[0429] Exact mass: 574

[0430] <Identification of Compound (1-b)>

[0431] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 624

[0432] Exact mass: 624

[0433] <Identification of Compound (1-c)>

[0434] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 674

[0435] Exact mass: 674

[0436] <Identification of Compound (1-d)>

[0437] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 674

[0438] Exact mass: 674

[0439] <Identification of Compound (1-e)>

[0440] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 724

[0441] Exact mass: 724

[0442] <Identification of Compound (1-f)>

[0443] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 774

[0444] Exact mass: 774

[0445] (Synthesis example 2)

[0446] <Preparation of Compound (2)>

[0447] The compound represented by formula (2) (compound (2)) is obtained in the same manner as the synthesis method of the compound represented by formula (8) described in Example 4 of International Publication No. 2022 / 024926.

[0448]

[0449] (Example 1)

[0450] <Preparation of coloring agent (3)>

[0451] 30 parts of the mixture (1) prepared in Synthesis Example 1, 15 parts of the compound (2) prepared in Synthesis Example 2 and 150 parts of propylene glycol monomethyl ether acetate (produced by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 27 hours. After the reaction solution was cooled to room temperature, 1500 parts of ethyl acetate were added. The obtained precipitate was obtained in the form of a suction filtration residue and washed with 1500 parts of ethyl acetate. After the obtained solid component and 750 parts of ethyl acetate were mixed and stirred at room temperature, the solid component was recovered by suction filtration, washed with 750 parts of ethyl acetate, and dried under reduced pressure at 60°C to obtain 35 parts of a mixture of compounds represented by formulas (3-a) to (3-f) (colorant (3)). The obtained mixture (colorant (3)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compounds represented by formulas (3-a) to (3-f). In addition, the obtained mixture (colorant (3)) was subjected to 1 As a result of H-NMR measurement, S1 / N1=3.4, S2 / N2=0.44, and the ratio of the number of groups represented by the formula (T-2) in the colorant (3) to the number of Al atoms was calculated to be 0.45.

[0452]

[0453] <Identification of Compound (3-a)>

[0454] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 740

[0455] Exact mass: 740

[0456] <Identification of Compound (3-b)>

[0457] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 790

[0458] Exact mass: 790

[0459] <Identification of Compound (3-c)>

[0460] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 840

[0461] Exact mass: 840

[0462] <Identification of Compound (3-d)>

[0463] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 840

[0464] Exact mass: 840

[0465] <Identification of Compound (3-e)>

[0466] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 890

[0467] Exact mass: 890

[0468] <Identification of Compound (3-f)>

[0469] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 940

[0470] Exact mass: 940

[0471] (Synthesis example 3)

[0472] <Preparation of mixture (4)>

[0473] Under nitrogen atmosphere, 18 parts of aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 44 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 20 parts of 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 180 parts of urea (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.41 parts of hexaammonium heptamolybdate tetrahydrate (manufactured by Kanto Chemical Co., Ltd.), and 320 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 230°C, and stirred for 18 hours. After the reaction liquid was cooled to 60°C, 1600 parts of ion-exchanged water was added. The obtained precipitate was obtained as a suction filtration residue and washed with 320 parts of ion-exchanged water. The obtained residue was washed with 320 parts of 1M hydrochloric acid and 320 parts of ion-exchanged water, and then further washed with 320 parts of 1M sodium hydroxide aqueous solution and 320 parts of ion-exchanged water. The obtained solid component and 320 parts of acetone were mixed at room temperature, heated to 50°C and stirred for 30 minutes. After the reaction solution was cooled to room temperature, the solid component was recovered by suction filtration, washed with 320 parts of acetone, and dried under reduced pressure at 60°C to obtain 64 parts of a mixture (4). The obtained mixture (4) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (1-a) to the compound represented by formula (1-f).

[0474] (Example 2)

[0475] <Preparation of Colorant (5)>

[0476] 55 parts of the mixture (4), 20 parts of the compound (2) prepared in Synthesis Example 2 and 280 parts of propylene glycol monomethyl ether acetate (produced by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 14 hours. After the reaction solution was cooled to room temperature, 1400 parts of ethyl acetate were added. The precipitate obtained was obtained in the form of a suction filtration residue and washed with 1400 parts of ethyl acetate. After the obtained solid component and 690 parts of ethyl acetate were mixed and stirred at room temperature, the solid component was recovered by suction filtration, washed with 690 parts of ethyl acetate, and then dried under reduced pressure at 60°C to obtain 65 parts of a mixture of compounds represented by formula (3-a) to formula (3-f) (colorant (5)). The obtained mixture (colorant (5)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (3-a) to formula (3-f). In addition, the obtained mixture (colorant (5)) was subjected to 1 As a result of H-NMR measurement, S1 / N1=3.2, S2 / N2=0.87, and the ratio of the number of groups represented by the formula (T-2) in the colorant (5) to the number of Al atoms was calculated to be 0.86.

[0477] (Synthesis Example 4)

[0478] <Preparation of mixture (6)>

[0479] Under nitrogen atmosphere, 1.0 part of aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 2.3 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.4 parts of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of urea (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.023 parts of hexaammonium heptamolybdate tetrahydrate (manufactured by Kanto Chemical Co., Ltd.), and 20 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 230°C, and stirred for 6 hours. After the reaction liquid was cooled to 60°C, 200 parts of methanol was added. The obtained precipitate was obtained as a suction filtration residue and washed with 100 parts of ion-exchanged water. The obtained residue was washed with 100 parts of 1M hydrochloric acid and 100 parts of ion-exchanged water, and then further washed with 100 parts of 1M sodium hydroxide aqueous solution and 100 parts of ion-exchanged water. The obtained solid component and 100 parts of acetone were mixed at room temperature, heated to 50°C and stirred for 30 minutes. After the reaction solution was cooled to room temperature, the solid component was recovered by suction filtration, washed with 100 parts of acetone, and dried under reduced pressure at 60°C to obtain 2.1 parts of a mixture (6). The obtained mixture (6) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (1-a) to formula (1-f).

[0480] (Example 3)

[0481] <Preparation of Colorant (7)>

[0482] 1.8 parts of the mixture (6), 0.61 parts of the compound (2) prepared in Synthesis Example 2 and 12 parts of propylene glycol monomethyl ether acetate (produced by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 10 hours. After the reaction solution was cooled to room temperature, 120 parts of ethyl acetate were added. The obtained precipitate was obtained in the form of a suction filtration residue and washed with 120 parts of ethyl acetate. After 120 parts of ethyl acetate was added to the obtained residue and stirred, the residue was filtered and washed with 120 parts of ethyl acetate. The obtained residue was dried under reduced pressure while heating at 60°C to obtain 1.9 parts of a mixture of compounds represented by formulas (3-a) to (3-f) (colorant (7)). The obtained mixture (colorant (7)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (3-a) to formula (3-f). In addition, the obtained mixture (colorant (7)) was subjected to 1 As a result of H-NMR measurement, S1 / N1=2.9, S2 / N2=1.1, and the ratio of the number of groups represented by the formula (T-2) in the colorant (7) to the number of Al atoms was calculated to be 1.1.

[0483] (Synthesis Example 5)

[0484] <Preparation of mixture (8)>

[0485] Under a nitrogen atmosphere, 1.0 part of aluminum chloride (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 1.9 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.0 parts of 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of urea (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.023 part of hexaammonium heptamolybdate tetrahydrate (manufactured by Kanto Chemical Co., Ltd.), and 20 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, and the temperature was raised to 230 °C and stirred for 6 hours. After cooling the reaction solution to 60 °C, 200 parts of methanol was added. The obtained precipitate was taken in the form of a suction filtration residue and washed with 100 parts of ion-exchanged water. After washing the obtained residue with 100 parts of 1M hydrochloric acid and 100 parts of ion-exchanged water, it was further washed with 100 parts of 1M aqueous sodium hydroxide solution and 100 parts of ion-exchanged water. The obtained solid component and 100 parts of acetone were mixed at room temperature, the temperature was raised to 50 °C and stirred for 30 minutes. After cooling the reaction solution to room temperature, the solid component was recovered by suction filtration, washed with 100 parts of acetone, and dried under reduced pressure at 60 °C to obtain 2.2 parts of mixture (8). The obtained mixture (8) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of six compounds represented by formula (1-a) to formula (1-f).

[0486] (Example 4)

[0487] <Preparation of Colorant (9)>

[0488] 1.8 parts of mixture (8), 0.60 part of compound (2) manufactured in Synthesis Example 2, and 12 parts of propylene glycol monomethyl ether acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, and the temperature was raised to 150 °C and stirred for 10 hours. After cooling the reaction solution to room temperature, 120 parts of ethyl acetate was added. The obtained precipitate was taken in the form of a suction filtration residue and washed with 120 parts of ethyl acetate. After adding 120 parts of ethyl acetate to the obtained residue and stirring, the residue was filtered and washed with 120 parts of ethyl acetate. The obtained residue was dried under reduced pressure at 60 °C to obtain 1.9 parts of a mixture (colorant (9)) of compounds represented by formula (3-a) to (3-f). The obtained mixture (colorant (9)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of six compounds represented by formula (3-a) to formula (3-f). In addition, the obtained mixture (colorant (9)) was subjected to 1 1H-NMR measurement, and as a result, S1 / N1 = 2.4 and S2 / N2 = 1.7, and the ratio of the number of groups represented by formula (T-2) to the number of Al atoms in colorant (9) was calculated to be 1.7.

[0489] (Synthesis Example 6)

[0490] <Preparation of mixture (10)>

[0491] In a nitrogen atmosphere, 1.0 part of aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 1.7 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.2 parts of 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of urea (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.023 parts of hexaammonium heptamolybdate tetrahydrate (manufactured by Kanto Chemical Co., Ltd.), and 20 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 230°C, and stirred for 6 hours. After the reaction liquid was cooled to 60°C, 200 parts of methanol was added. The obtained precipitate was obtained as a suction filtration residue and washed with 100 parts of ion-exchanged water. The obtained residue was washed with 100 parts of 1M hydrochloric acid and 100 parts of ion-exchanged water, and then further washed with 100 parts of 1M sodium hydroxide aqueous solution and 100 parts of ion-exchanged water. The obtained solid component and 100 parts of acetone were mixed at room temperature, heated to 50°C and stirred for 30 minutes. After the reaction solution was cooled to room temperature, the solid component was recovered by suction filtration, washed with 100 parts of acetone, and dried under reduced pressure at 60°C to obtain 2.8 parts of a mixture (10). The obtained mixture (10) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (1-a) to formula (1-f).

[0492] (Example 5)

[0493] <Preparation of Colorant (11)>

[0494] 2.5 parts of the mixture (10), 0.82 parts of the compound (2) prepared in Synthesis Example 2 and 16 parts of propylene glycol monomethyl ether acetate (produced by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 10 hours. After the reaction solution was cooled to room temperature, 170 parts of ethyl acetate were added. The obtained precipitate was obtained in the form of a suction filtration residue and washed with 170 parts of ethyl acetate. After 170 parts of ethyl acetate was added to the obtained residue and stirred, the residue was filtered and washed with 170 parts of ethyl acetate. The obtained residue was heated at 60°C and dried under reduced pressure to obtain 2.4 parts of a mixture of compounds represented by formulas (3-a) to (3-f) (colorant (11)). The obtained mixture (colorant (11)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (3-a) to formula (3-f). In addition, the obtained mixture (colorant (11)) was subjected to 1 As a result of H-NMR measurement, S1 / N1=2.1, S2 / N2=1.9, and the ratio of the number of groups represented by the formula (T-2) in the colorant (11) to the number of Al atoms was calculated to be 1.9.

[0495] (Synthesis Example 7)

[0496] <Preparation of mixture (12)>

[0497] 1.5 parts of mixture (4), 0.76 part of 1,3 - dibromo - 5,5 - dimethylhydantoin and 15 parts of concentrated sulfuric acid were mixed under an ice bath, and then stirred at room temperature for 6 hours. Subsequently, the solution was poured into 150 parts of cold water, and the resulting precipitate was obtained in the form of a suction filtration residue and washed with 105 parts of ion - exchanged water. The obtained solid component was mixed with 15 parts of 2.5% aqueous sodium hydroxide solution at room temperature, stirred, and then filtered. The resulting precipitate was washed with 30 parts of ion - exchanged water and then dried under reduced pressure by heating at 60 °C to obtain 1.2 parts of mixture (12). According to the mass spectrometry analysis of the obtained mixture (12), it was confirmed that it contained a peak corresponding to the same molecular weight as the bromo - substituted compound of formula (1 - b) represented by formula (12), and mixture (12) was identified as the bromo - substituted product of the target mixture of compounds represented by formula (1 - a) to formula (1 - f).

[0498]

[0499] (Example 6)

[0500] <Preparation of colorant (13)>

[0501] 1.0 part of mixture (12), 0.32 part of compound (2) prepared in Synthesis Example 2 and 5 parts of propylene glycol monomethyl ether acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature and heated to 150 °C and stirred for 10 hours. After the reaction solution was cooled to room temperature, 25 parts of ethyl acetate was added. The resulting precipitate was obtained in the form of a suction filtration residue and washed with 25 parts of ethyl acetate. The obtained residue was dried under reduced pressure by heating at 60 °C to obtain 2.4 parts of mixture (colorant (13)). The ratio of the number of groups represented by formula (T - 2) to the number of Al atoms in this mixture was 0.86, the same as that of colorant (5). SEM - EDX measurement was performed on this mixture, and it was confirmed that the average number of bromine substitutions per 1 molecule of the compound was 1. According to the mass spectrometry analysis of the obtained colorant (13), it was confirmed that it contained a peak corresponding to the same molecular weight as the bromo - substituted compound of formula (3 - b) represented by formula (13), and colorant (13) was identified as the bromo - substituted product of the target mixture of compounds represented by formula (3 - a) to formula (3 - f).

[0502]

[0503] (Synthesis Example 8)

[0504] <Preparation of mixture (14)>

[0505] 1.4 parts of a mixture (14) were prepared in the same manner as the preparation of the mixture (12), except that the amount of 1,3-dibromo-5,5-dimethylhydantoin was changed from 0.76 parts to 2.8 parts. The obtained mixture (14) was confirmed to contain a peak having the same molecular weight as the bromine-substituted compound of the formula (1-b) represented by the formula (14) by mass spectrometry analysis, and the mixture (14) was identified as a bromine-substituted product of the target compound, i.e., a mixture of the compounds represented by the formulas (1-a) to (1-f).

[0506]

[0507] (Example 7)

[0508] <Preparation of Colorant (15)>

[0509] 0.52 parts of a mixture (colorant (15)) was prepared in the same manner as the preparation of colorant (13), except that 1.0 parts of mixture (12) was changed to 1.0 parts of mixture (14) and the amount of compound (2) prepared in Synthesis Example 2 was changed from 0.32 parts to 0.24 parts. The ratio of the number of groups represented by formula (T-2) to the number of Al atoms in the mixture was 0.86, similar to colorant (5). The mixture was subjected to SEM-EDX measurement, and it was confirmed that the average number of bromine substitutions per molecule of the compound was 5. According to the mass spectrometry analysis of the obtained colorant (15), it was confirmed that it contained a peak with the same molecular weight as the bromine-substituted compound of formula (3-b) represented by formula (15), and was identified as a bromine-substituted product of the target compound, i.e., a mixture of compounds represented by formula (3-a) to formula (3-f).

[0510]

[0511] (Synthesis Example 9)

[0512] <Preparation of mixture (16)>

[0513] 3.3 parts of a mixture (16) were synthesized by the same method as the method described in

[0071] to

[0072] of JP-A-2012-507743 except that 1-chloronaphthalene, urea, 4-fluorophthalonitrile and aluminum trichloride as raw materials were changed to 3.8 parts of 1-chloronaphthalene, 0.057 parts of urea, 2.5 parts of 4-fluorophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.0 parts of 2,3-dicyanonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 0.75 parts of aluminum trichloride. The obtained mixture (16) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of compounds represented by formulas (16-a) to (16-e) and 6 compounds represented by formula (1-f).

[0514]

[0515] <Identification of Compound (16-a)>

[0516] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 646

[0517] Exact mass: 646

[0518] <Identification of Compound (16-b)>

[0519] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 678

[0520] Exact mass: 678

[0521] <Identification of Compound (16-c)>

[0522] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 710

[0523] Exact mass: 710

[0524] <Identification of Compound (16-d)>

[0525] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 710

[0526] Exact mass: 710

[0527] <Identification of Compound (16-e)>

[0528] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 742

[0529] Exact mass: 742

[0530] <Identification of Compound (1-f)>

[0531] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 774

[0532] Exact mass: 774

[0533] (Example 8)

[0534] <Preparation of Colorant (17)>

[0535] 2.5 parts of the mixture (16), 0.82 parts of the compound (2) prepared in Synthesis Example 2, and 16 parts of propylene glycol monomethyl ether acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C, and stirred for 10 hours. After the reaction solution was cooled to room temperature, 170 parts of ethyl acetate was added. The obtained precipitate was obtained as a suction filtration residue and washed with 170 parts of ethyl acetate. After 170 parts of ethyl acetate was added to the obtained residue and stirred, the residue was filtered and washed with 170 parts of ethyl acetate. The obtained residue was heated at 60°C and dried under reduced pressure to obtain 1.0 parts of a mixture (colorant (17)) of compounds represented by formula (17-a) to (17-e) and a compound represented by formula (3-f). The obtained mixture (colorant (17)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of compounds represented by formula (17-a) to (17-e) and 6 compounds represented by formula (3-f). In addition, the obtained mixture (colorant (17)) is subjected to 1 As a result of H-NMR measurement, S1 / N1=3.5, S2 / N2=0.75, and the ratio of the number of groups represented by the formula (T-2) in the colorant (17) to the number of Al atoms was calculated to be 0.69.

[0536]

[0537] <Identification of Compound (17-a)>

[0538] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 812

[0539] Exact mass: 812

[0540] <Identification of Compound (17-b)>

[0541] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 844

[0542] Exact mass: 844

[0543] <Identification of Compound (17-c)>

[0544] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 876

[0545] Exact mass: 876

[0546] <Identification of Compound (17-d)>

[0547] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] – 876

[0548] Exact mass: 876

[0549] <Identification of Compound (17-e)>

[0550] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 908

[0551] Exact mass: 908

[0552] <Identification of Compound (3-f)>

[0553] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 940

[0554] Exact mass: 940

[0555] (Synthesis Example 10)

[0556] <Preparation of mixture (18)>

[0557] 3.0 parts of a mixture (18) were synthesized by the same method as described in

[0071] to

[0072] of JP-A-2012-507743 except that 1-chloronaphthalene, urea, 4-fluorophthalonitrile and aluminum trichloride as raw materials were changed to 12 parts of 1-chloronaphthalene, 0.046 parts of urea, 2.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.0 parts of 6-bromo-2,3-dicyanonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 0.60 parts of aluminum trichloride. The obtained mixture (18) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by formula (18-a) to formula (18-f).

[0558]

[0559] <Identification of Compound (18-a)>

[0560] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 798

[0561] Exact mass: 798

[0562] <Identification of Compound (18-b)>

[0563] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 870

[0564] Exact mass: 870

[0565] <Identification of Compound (18-c)>

[0566] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 942

[0567] Exact mass: 942

[0568] <Identification of Compound (18-d)>

[0569] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 942

[0570] Exact mass: 942

[0571] <Identification of Compound (18-e)>

[0572] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 1014

[0573] Exact mass: 1014

[0574] <Identification of Compound (18-f)>

[0575] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 1086

[0576] Exact mass: 1086

[0577] (Example 9)

[0578] <Preparation of Colorant (19)>

[0579] 1.0 part of the mixture (18), 0.82 parts of the compound (2) prepared in Synthesis Example 2 and 5.0 parts of propylene glycol monomethyl ether acetate (produced by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 10 hours. After the reaction solution was cooled to room temperature, 25 parts of ethyl acetate were added. The obtained precipitate was obtained in the form of a suction filtration residue and washed with 25 parts of ethyl acetate. After 13 parts of ethyl acetate were added to the obtained residue and stirred, the residue was filtered and washed with 13 parts of ethyl acetate. The obtained residue was heated at 60°C and dried under reduced pressure to obtain 0.79 parts of a mixture of compounds represented by formulas (19-a) to (19-f) (colorant (19)). The obtained mixture (colorant (19)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (19-a) to formula (19-f). In addition, the obtained product was subjected to 1 As a result of H-NMR measurement, S1 / N1=3.9, S2 / N2=0.69, and the ratio of the number of groups represented by the formula (T-2) in the colorant (19) to the number of Al atoms was calculated to be 0.60.

[0580]

[0581] <Identification of Compound (19-a)>

[0582] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 964

[0583] Exact mass: 964

[0584] <Identification of Compound (19-b)>

[0585] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 1036

[0586] Exact mass: 1036

[0587] <Identification of Compound (19-c)>

[0588] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 1108

[0589] Exact mass: 1108

[0590] <Identification of Compound (19-d)>

[0591] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] - 1108

[0592] Exact mass: 1108

[0593] <Identification of Compound (19-e)>

[0594] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 1180

[0595] Exact mass: 1180

[0596] <Identification of Compound (19-f)>

[0597] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 1252

[0598] Exact mass: 1252

[0599] (Synthesis Example 11)

[0600] <Preparation of Compound (20)>

[0601] A compound represented by formula (20) (compound (20)) is obtained in the same manner as the synthesis method of the compound represented by formula (6) described in Example 3 of International Publication No. 2022 / 024926.

[0602]

[0603] (Example 10)

[0604] <Preparation of Colorant (21)>

[0605] 1.0 part of the mixture (4), 0.36 parts of the compound (20) prepared in Synthesis Example 11 and 5.0 parts of propylene glycol monomethyl ether acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 8 hours. After the reaction solution was cooled to room temperature, 25 parts of ethyl acetate were added. The obtained precipitate was obtained as a suction filtration residue and washed with 25 parts of ethyl acetate. The obtained solid component and 13 parts of ethyl acetate were mixed and stirred at room temperature, and the solid component was recovered by suction filtration, washed with 13 parts of ethyl acetate, and dried under reduced pressure at 60°C to obtain 1.1 parts of a mixture (colorant (21)). The ratio of the number of groups represented by formula (T-2) to the number of Al atoms in the mixture was 0.86, similar to that of the colorant (5). In addition, the obtained mixture (colorant (21)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (21-a) to formula (21-f).

[0606]

[0607] <Identification of Compound (21-a)>

[0608] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 744

[0609] Exact mass: 744

[0610] <Identification of Compound (21-b)>

[0611] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 794

[0612] Exact mass: 794

[0613] <Identification of Compound (21-c)>

[0614] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 844

[0615] Exact mass: 844

[0616] <Identification of Compound (21-d)>

[0617] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 844

[0618] Exact mass: 844

[0619] <Identification of Compound (21-e)>

[0620] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 894

[0621] Exact mass: 894

[0622] <Identification of Compound (21-f)>

[0623] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 944

[0624] Exact mass: 944

[0625] (Synthesis Example 12)

[0626] <Preparation of Compound (22)>

[0627] A compound represented by formula (22) (compound (22)) was obtained by the same method as the method for synthesizing the compound represented by formula (25) described in Example 13 of International Publication No. 2022 / 024926, except that 3-butyn-1-ol was changed to 4-pentyn-2-ol.

[0628]

[0629] (Example 11)

[0630] <Preparation of Colorant (23)>

[0631] 1.0 part of the mixture (4), 0.42 parts of the compound (22) prepared in Synthesis Example 12 and 5.0 parts of propylene glycol monomethyl ether acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed at room temperature, heated to 150°C and stirred for 8 hours. After the reaction solution was cooled to room temperature, 25 parts of ethyl acetate were added. The obtained precipitate was obtained as a suction filtration residue and washed with 25 parts of ethyl acetate. The obtained solid component and 13 parts of ethyl acetate were mixed and stirred at room temperature, and the solid component was recovered by suction filtration, washed with 13 parts of ethyl acetate, and dried under reduced pressure at 60°C to obtain 0.9 parts of a mixture (colorant (23)). The ratio of the number of groups represented by formula (T-2) to the number of Al atoms in the mixture was 0.86, similar to that of the colorant (5). In addition, the obtained mixture (colorant (23)) was subjected to mass spectrometry analysis, and it was confirmed that the mixture was a mixture of 6 compounds represented by the compound represented by formula (23-a) to formula (23-f).

[0632]

[0633] <Identification of Compound (23-a)>

[0634] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 778

[0635] Exact mass: 778

[0636] <Identification of Compound (23-b)>

[0637] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 828

[0638] Exact mass: 828

[0639] <Identification of Compound (23-c)>

[0640] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 878

[0641] Exact mass: 878

[0642] <Identification of Compound (23-d)>

[0643] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] –- 878

[0644] Exact mass: 878

[0645] <Identification of Compound (23-e)>

[0646] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 928

[0647] Exact mass: 928

[0648] <Identification of Compound (23-f)>

[0649] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M] -– 978

[0650] Exact mass: 978

[0651] (Comparative Example 1)

[0652] According to the synthesis method described in Example 4 of International Publication No. 2022 / 024926, a compound represented by formula (x1) (hereinafter referred to as compound (x1)) was obtained.

[0653]

[0654] (Resin Synthesis Example 1)

[0655] <Preparation of Resin B-1>

[0656] A suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 340 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Then, 57 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0 2,6 ] A mixed solution of 54 parts of a mixture of decane-9-yl ester (containing a molar ratio of 1:1), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution of 40 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition of the initiator solution was completed, it was kept at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a viscosity of 127 mPas and a solid content of 37.0% as measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer is 9.4×10 3 , the dispersion degree was 1.89, and the acid value converted to solid content was 114 mg-KOH / g. Resin B-1 had the following structural units.

[0657]

[0658] (Dispersion Preparation Example 1)

[0659] 5 parts of the colorant (3) obtained in Example 1, 3 parts of a dispersant (BYK LPN-6919 manufactured by BYK) (in terms of solid content), 3 parts of a resin (B-1) (in terms of solid content), and 89 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 μm zirconium oxide beads were added, and the mixture was shaken for 0.5 hours using a paint conditioner (manufactured by LAU). The zirconium oxide beads were then removed by filtration to obtain a dispersion (A-1).

[0660] (Dispersion Preparation Example 2)

[0661] 5 parts of the compound (x1) obtained in Comparative Example 1, 4 parts of a dispersant (BYK LPN-6919 manufactured by BYK) (in terms of solid content), 4 parts of a resin (B-1) (in terms of solid content), and 87 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 μm zirconium oxide beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). The zirconium oxide beads were then removed by filtration to obtain a dispersion (X-1).

[0662] (Preparation of Colored Resin Composition 1)

[0663] The colored resin composition 1 is obtained by mixing the following components.

[0664] Dispersion liquid (A-1) 415 parts

[0665] Resin (B-1) (solid content conversion) 48 parts

[0666] Polymerizable compound (C-1): dipentaerythritol polyacrylate: trade name A-9550: manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 20 parts

[0667] Polymerizable compound (C-2): trimethylolpropane triacrylate: trade name A-TMPT: manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 20 parts

[0668] Polymerization initiator (D): N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine: trade name PBG-327: O-acyl oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd. 5 parts

[0669] Solvent (E): 645 parts of propylene glycol monomethyl ether acetate

[0670] Leveling agent (F): Polyether-modified silicone oil: Trade name Toray Silicone SH8400: manufactured by Dow Corning Toray Co., Ltd. 0.1 part

[0671] (Preparation of Comparative Colored Resin Composition 1)

[0672] Comparative colored resin composition 1 was obtained by mixing the following components.

[0673] Dispersion liquid (X-1) 432 parts

[0674] Resin (B-1) (solid content conversion) 43 parts

[0675] Polymerizable compound (C-1): dipentaerythritol polyacrylate: trade name A-9550: manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 20 parts

[0676] Polymerizable compound (C-2): trimethylolpropane triacrylate: trade name A-TMPT: manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 20 parts

[0677] Polymerization initiator (D): N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine: trade name PBG-327: O-acyl oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd. 5 parts

[0678] Solvent (E): 680 parts of propylene glycol monomethyl ether acetate

[0679] Leveling agent (F): Polyether-modified silicone oil: Trade name Toray Silicone SH8400: manufactured by Dow Corning Toray Co., Ltd. 0.1 part

[0680] (Formation of Colored Coating Film)

[0681] Colored resin composition 1 and comparative colored resin composition 1 were applied onto 5 cm square glass substrates (EAGLE 2000; manufactured by CORNING) by spin coating, and then pre-baked at 100°C for 3 minutes to obtain colored coating films. The pre-baked colored coating films were then post-baked at 230°C for 10 minutes.

[0682] (Color measurement of colored coating films)

[0683] The color coating film after post-baking was spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and the stimulus value Y in the XYZ color system of CIE were measured using the characteristic function of the C light source. The distance between the obtained xy chromaticity coordinate measurement value (converted film thickness 1.0 μm) and the chromaticity coordinates (0.30, 0.60) of the green vertex under the sRGB standard when the converted film thickness was 1.0 μm was calculated. The smaller the distance, the more ideal the characteristics as a green color material.

[0684] In addition, the transmittance of the color coating film after post-baking was measured. At this time, the transmittance X at a wavelength of 570 nm when the film thickness was 1.0 μm was calculated.570 Transmittance X at wavelength 530nm 530 The ratio (X 570 / X 530 ). The closer this value is to 1, the higher the transmittance of the green region is, so it is preferred as a characteristic of a green color material.

[0685] The results are shown in Table 2, with the colored coating film obtained from the colored resin composition 1 being referred to as Example A1 and the colored coating film obtained from the comparative colored resin composition 1 being referred to as Comparative Example A1.

[0686] [Table 2]

[0687]

[0688] Industrial Applicability

[0689] According to the compound, the colorant, and the colored resin composition of the present invention, the green spectrum characteristics of the obtained coating film can be further improved, and thus a color filter excellent in various characteristics can be provided.

Claims

1. A colorant comprising a compound represented by formula (I), The ratio of the number of groups represented by formula (T-2) in the colorant to the number of Al atoms in the compound represented by formula (I) is 0.1 to 3, In formula (I), R 1 and R 2 Each independently represents a hydrogen atom, a hydroxyl group, -R 13 or -O-R 13 , R 1 and R 2 At least one of them indicates -R 13 or -O-R 13 When R 1 and R 2 can bond to each other to form a ring, Ring T 1 , Ring T 2 , Ring T 3 and Ring T 4 Each independently represents a group represented by formula (T-1) or formula (T-2), In formula (T-1), R 3 ~R 6 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group, * indicates the bonding site with the pyrrole ring, In formula (T-2), R 7 ~R 12 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group, * indicates the bonding site with the pyrrole ring, R 13 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 13 , they may be the same or different from each other, R 14 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, and when there are a plurality of Rs 14 they may be the same as or different from each other.

2. The colorant according to claim 1, in, At least ring T 1 , Ring T 2 , Ring T 3 and Ring T 4 The compound represented by the formula (I) is a compound in which 1 to 3 of the groups are groups represented by the formula (T-2).

3. A colored resin composition comprising the colorant according to claim 1 or 2, a resin and a solvent.

4. The colored resin composition according to claim 3, in, It further contains a polymerization initiator and a polymerizable compound. A color filter formed from the colored resin composition according to claim 4. A display device comprising the color filter according to claim 5 . 7 . A solid-state imaging element comprising the color filter according to claim 5 .

8. A compound represented by formula (II), In formula (II), R 1 and R 2 Each independently represents a hydrogen atom, a hydroxyl group, -R 13 or -O-R 13 , R 1 and R 2 At least one of them indicates -R 13 or -O-R 13 When R 1 and R 2 can bond to each other to form a ring, Ring T 21 , Ring T 22 , Ring T 23 and Ring T 24 Each independently represents a group represented by formula (T-1) or formula (T-2), in, Ring T 21 , Ring T 22 , Ring T 23 and Ring T 24 1 to 3 of them represent groups represented by formula (T-2), In formula (T-1), R 3 ~R 6 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group, * indicates the bonding site with the pyrrole ring, In formula (T-2), R 7 ~R 12 Each independently represents a hydrogen atom, -R 13 , -O-R 13 , -S-R 13 , -SO 2 N(R 14 ) 2 , -N(R 14 ) 2 , halogen atom or nitro group, * indicates the bonding site with the pyrrole ring, R 13 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 13 , they may be the same or different from each other, R 14 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and there are multiple R 14 , they may be the same as or different from each other.

Images