Coloring composition, compound, color filter and display device

Abstract

The present invention aims to provide a compound having a maximum absorption wavelength on the longest wavelength side of an absorption spectrum at a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of conventionally known CI Pigment Yellow 138, and / or a compound having a wavelength of a shoulder peak on the longest wavelength side of an absorption spectrum, and a coloring composition containing the compound. A compound represented by formula (I) (wherein Q 1 and Q 2 At least one of them is a group represented by formula (QQ20)).

Description

Technical Field

[0001] The present invention relates to a coloring composition, a compound, a color filter and a display device. Background Art

[0002] The coloring composition is used for producing a color filter used in a display device such as a liquid crystal display device, an electroluminescent display device, etc. As a colorant contained in the coloring composition, CI Pigment Yellow 138 is known (Patent Document 1).

[0003]

[0004] (CI Pigment Yellow 138)

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Publication No. 2013-82906 Summary of the invention

[0008] In recent years, displays have been developed to expand the color reproduction range that can be displayed, and as part of this, color filters are also required to have deeper colors. In order to meet this requirement, a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum on a longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the conventionally known CI Pigment Yellow 138, and / or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum, and a coloring composition containing the compound are required.

[0009] The wavelength of the shoulder peak on the longest wavelength side of the above-mentioned absorption spectrum refers to the wavelength of the average value of the wavelength of the inflection point on the longest wavelength side of the absorption spectrum and the wavelength of the inflection point on the second longest wavelength side of the absorption spectrum, when the compound does not have a maximum absorption wavelength on the longest wavelength side of the absorption spectrum on a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of CI Pigment Yellow 138 and has two or more inflection points of the absorption spectrum on a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum.

[0010] The present invention provides the following [1] to [5].

[0011] [1] A compound represented by the following formula (I).

[0012]

[0013] [In formula (I),

[0014] R 1 ~R 5each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

[0015] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0016] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0017] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0018] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0019] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0020] R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 They may be bonded to each other to form a ring.

[0021] M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).

[0022] MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).

[0023] Z 1 ~Z 4 each independently represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

[0024] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0025] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0026] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0027] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0028] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0029] Q 1 and Q 2 may each independently represent a divalent hydrocarbon group or a divalent heterocyclic group

[0030] -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-,

[0031] -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-,

[0032] -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=,

[0033] The -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0034] The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0035] Z 1 ~Z 4 When there are plural numbers of , M and MM respectively, they may be the same as or different from each other.

[0036] Q 1 and Q 2 At least one of them is a group represented by formula (QQ20).

[0037]

[0038] [In formula (QQ20),

[0039] p is an integer greater than 0,

[0040] q is an integer greater than 0,

[0041] The sum of p and q is an integer greater than or equal to 1.

[0042] L represents a (2p+2q+2)-valent hydrocarbon group or a (2p+2q+2)-valent heterocyclic group,

[0043] The -C(-)(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -Si(-)(-)-,

[0044] The -CH(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -N(-)-,

[0045] The -CH= constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -N=,

[0046] The -CH2- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0047] The hydrogen atoms constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0048] Q 3 and Q 4 each independently represents a divalent hydrocarbon group or a divalent heterocyclic group,

[0049] -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-,

[0050] -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-,

[0051] -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=,

[0052] The -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0053] The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0054] R Q95 ~R Q104 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

[0055] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0056] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0057] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0058] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0059] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0060] R Q95 ~R Q104 can be selected from R Q95 ~R Q104 One or more of them are bonded to each other to form a ring.

[0061] M and MM have the same meanings as described above.

[0062] ※Indicates bonding site.

[0063] Q 3 , Q 4 , R Q95 ~R Q104 When , M and MM exist in plural numbers, they may be the same as or different from each other. ]]

[0064] [2] A coloring composition comprising the compound described in [1] and a resin.

[0065] [3] The colored composition according to [2], comprising a polymerizable compound and a polymerization initiator.

[0066] [4] A color filter formed from the coloring composition according to [2] or [3].

[0067] [5] A display device comprising the color filter described in [4].

[0068] According to the present invention, a coloring composition and a compound that can be used to form a color filter with a darker color than a coloring composition containing CI Pigment Yellow 138 are provided. DETAILED DESCRIPTION

[0069] [Coloring composition]

[0070] The colored composition of the present invention contains a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a resin (hereinafter, sometimes referred to as resin (B)).

[0071]

[0072] [In formula (I),

[0073] R 1 ~R 5 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

[0074] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0075] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0076] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0077] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0078] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0079] R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 They may be bonded to each other to form a ring.

[0080] M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).

[0081] MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).

[0082] Z 1 ~Z 4 each independently represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

[0083] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0084] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0085] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0086] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0087] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0088] Q 1 and Q 2 may each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,

[0089] -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-,

[0090] -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-,

[0091] -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=,

[0092] The -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0093] The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0094] Z 1 ~Z 4 When there are plural numbers of , M and MM respectively, they may be the same as or different from each other.

[0095] Q 1 and Q 2 At least one of them is a group represented by formula (QQ20).

[0096]

[0097] [In formula (QQ20),

[0098] p is an integer greater than 0,

[0099] q is an integer greater than 0,

[0100] The sum of p and q is an integer greater than or equal to 1.

[0101] L represents a (2p+2q+2)-valent hydrocarbon group or a (2p+2q+2)-valent heterocyclic group,

[0102] The -C(-)(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -Si(-)(-)-,

[0103] The -CH(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -N(-)-,

[0104] The -CH= constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -N=,

[0105] The -CH2- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0106] The hydrogen atoms constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0107] Q 3 and Q 4 each independently represents a divalent hydrocarbon group or a divalent heterocyclic group,

[0108] -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-,

[0109] -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-,

[0110] -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=,

[0111] The -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0112] The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0113] R Q95 ~R Q104 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

[0114] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0115] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0116] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0117] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0118] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0119] R Q95 ~R Q104 can be selected from R Q95 ~R Q104 One or more of them are bonded to each other to form a ring.

[0120] M and MM have the same meanings as described above.

[0121] ※Indicates bonding site.

[0122] Q 3 , Q 4 , R Q95 ~R Q104 When , M and MM exist in plural numbers, they may be the same as or different from each other. ]]

[0123] Compound (I) also includes its tautomers and salts thereof.

[0124] Compound (I) can be used as a colorant.

[0125] The colored composition of the present invention may contain one or more compounds (I).

[0126] The colored composition of the present invention may contain a solvent (hereinafter, sometimes referred to as a solvent (E)).

[0127] The colored composition of the present invention may contain a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)).

[0128] The colored composition of the present invention may contain a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).

[0129] The colored composition of the present invention may contain a polymerization initiation aid (hereinafter, sometimes referred to as a polymerization initiation aid (D1)).

[0130] The colored composition of the present invention may contain a colorant other than the compound (I) (hereinafter, sometimes referred to as a colorant (A1). Also, hereinafter, the compound (I) and the colorant (A1) may be collectively referred to as a "colorant (A)").

[0131] The colorant (A1) may contain one or more colorants.

[0132] The colorant (A1) preferably contains one or more selected from the group consisting of a yellow colorant, an orange colorant, a red colorant, and a green colorant.

[0133] The colored composition of the present invention may contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

[0134] The colored composition of the present invention may contain an antioxidant (hereinafter, sometimes referred to as antioxidant (G)).

[0135] [Compound (I)]

[0136] The present invention is described in more detail below by giving partial structures of compound (I). In each partial structure, even if only a substituent bonded to a ring structure is bonded to a certain part of the ring structure, the following examples also include the substituents bonded to all parts of the ring structure. One or more substituents may be bonded to the ring structure, and when more than two substituents are bonded to the ring structure, the substituents may be the same or different.

[0137] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom, a chlorine atom and a bromine atom are preferred.

[0138] R 1 ~R 5 and Z 1 ~Z 4 The number of carbon atoms of the hydrocarbon group represented is 1 to 40, preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 18, and particularly preferably 1 to 12.

[0139] R 1 ~R 5 and Z 1 ~Z 4 The monovalent hydrocarbon group having 1 to 40 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).

[0140] As R 1 ~R 5 and Z 1 ~Z 4The saturated or unsaturated chain hydrocarbon group represented by , may be a straight-chain alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, trineicosyl, dotriacontyl, trictriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, heptatriacontyl, octatriacontyl, nonacosyl and tetracontyl; 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, 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 branched alkyl groups such as vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1-(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,2-dimethyl-1-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- alkenyl groups such as 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, 1,1-dimethyl-2-propenyl, 1-ethyl-2-propenyl, and 1-methyl-1-butenyl; ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), octynyl (e.g., 1-octynyl, 7-octynyl), butynyl, pentynyl, hexynyl, heptynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 1,1-dimethyl-2-propenyl, 1-ethyl-2-propenyl, and 1-methyl-1-butenyl; carbonAlkynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecanyl, octadecynyl, nonadecanyl and eicosynyl; etc. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 18, and particularly preferably 1 to 12. Among them, a linear or branched alkyl group having 1 to 12 carbon atoms is particularly preferred.

[0141] As R 1 ~R 5 and Z 1 ~Z 4 The saturated or unsaturated alicyclic hydrocarbon group represented by 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, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3- Cycloalkyl groups such as 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; 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; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl; etc. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20, further preferably 3 to 18, and particularly preferably 3 to 12. Among them, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and adamantyl are particularly preferred.

[0142] As R 1 ~R 5 and Z 1 ~Z 4The aromatic hydrocarbon group represented by phenyl includes 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-butyl)phenyl, 3,5-di(tert-butyl)-4-methylphenyl, Phenyl, 4-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, The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, further preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms.

[0143] R 1 ~R 5 and Z 1 ~Z 4 The hydrocarbon group represented by may be a group obtained by combining the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include 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, Aralkyl groups such as methyl, 1-phenylethyl, 1,1-diphenylethyl, phenethyl, 1-methyl-1-phenylethyl, (1-naphthyl)methyl and (2-naphthyl)methyl; arylalkenyl groups such as 1-phenylvinyl, 2-phenylvinyl (phenylvinyl), 2,2-diphenylvinyl and 2-phenyl-2-(1-naphthyl)vinyl; arylalkynyl groups such as phenylethynyl; phenyl groups having one or more phenyl groups bonded thereto such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl and (dimethyl(phenyl)methyl)phenyl, etc.

[0144] The number of carbon atoms in these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12. The lower limit of these ranges is preferably 7.

[0145] R1 ~R 5 and Z 1 ~Z 4 The group represented is a group obtained by combining the above-mentioned hydrocarbon groups (for example, chain hydrocarbon groups and alicyclic hydrocarbon groups), and can be, for example, an alkyl group to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl, and adamantylmethyl.

[0146] The number of carbon atoms in these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12.

[0147] R 1 ~R 5 and Z 1 ~Z 4 The monovalent heterocyclic group having 1 to 40 carbon atoms represented by means of a group containing a heteroatom as a constituent element of the ring. The monovalent heterocyclic group having 1 to 40 carbon atoms may be a monocyclic ring or a polycyclic ring. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0148] The heterocyclic group has preferably 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, further preferably 3 to 18 carbon atoms, particularly preferably 3 to 12 carbon atoms.

[0149] Examples of the heterocyclic ring containing a nitrogen atom include aziridine, azetidine, pyrrolidine, piperidine and piperazine, monocyclic saturated heterocyclic rings such as pyrrole, 1-methylpyrrole and 2,5-dimethylpyrrole, pyrroles such as 1-methylpyrrole, 2-methylpyrrole, 3-methylpyrrole, 4-methylpyrazole and 5-methylpyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole, and pyridine, pyridazine, pyrimidine, 6- Pyrimidines such as methylpyrimidine, 6-membered unsaturated heterocycles such as pyrazine and 1,3,5-triazine; condensed bicyclic heterocycles such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; etc.

[0150] Examples of the heterocyclic ring containing an oxygen atom include oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dihydropyran, Alkane and 1,4-diol 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, 1,4-dioxaspiro[4.4]nonane and other saturated heterocyclic rings; α-acetone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone and other lactone heterocyclic rings; 5-membered unsaturated heterocyclic rings such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran and other furans; 6-membered unsaturated heterocyclic rings such as 2H-pyran and 4H-pyran; 1-benzofuran and other benzofurans, benzopyrans, 4-methylbenzopyran and other benzopyrans, methylenedioxybenzene, 1,3-methylenedioxybenzene, benzodioxybenzene Condensed bicyclic heterocycles such as alkanes, chromans and isochromans; Condensed tricyclic heterocycles such as xanthenes and dibenzofurans; etc.

[0151] Examples of the heterocycle containing a sulfur atom include a 5-membered saturated heterocycle such as dithiolane; a 6-membered saturated heterocycle such as thiazane, 1,3-dithiane, and 2-methyl-1,3-dithiane; a 5-membered unsaturated heterocycle and a 6-membered unsaturated heterocycle such as thiophene, 3-methylthiophene, and 2-carboxythiophene; a thiopyran such as 2H-thiopyran, 4H-thiopyran, and a benzothiopyran such as benzotetrahydrothiopyran; a condensed bicyclic heterocycle such as benzothiopyran, benzotetrahydrothiopyran, and benzothiophene; and a condensed tricyclic heterocycle such as thianthrene and dibenzothiophene.

[0152] Examples of the heterocyclic ring containing nitrogen atoms and oxygen atoms include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone and 2-methyl-2-piperidone; Azole, 4-methyl Azoles, etc. 2-Methylisothiazolyl azole, 3-methylisothiazolyl 4-Methylisothiazolyl azole, 5-methylisothiazolyl Isopropylamine Monocyclic unsaturated heterocyclic rings such as azoles; benzo azole, benzyl isocyanate Azoles, benzo Azine, benzodioxadiazine Alkane, benzimidazolinium and other fused bicyclic heterocyclic rings; phenanthracene Oxazine and other fused tricyclic heterocyclic rings; etc.

[0153] Examples of the heterocycle containing a nitrogen atom and a sulfur atom include monocyclic heterocycles such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole, 2,4-dimethylthiazole, etc.; condensed bicyclic heterocycles such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine, etc.; and the like.

[0154] In addition, the bonding position of the above-mentioned heterocyclic group is a portion after any hydrogen atom contained in each heterocyclic ring is removed.

[0155] The heterocyclic group may be a group obtained by combining the above-mentioned heterocyclic ring and the above-mentioned hydrocarbon group, and examples thereof include tetrahydrofuranyl group and the like.

[0156] Furthermore, the above heterocyclic group may be a group represented by the following formula: ※ indicates a bonding site.

[0157]

[0158] -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-,

[0159] -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-,

[0160] -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=,

[0161] -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-.

[0162] The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with halogen atoms, cyano groups, nitro groups, -SO3M, -CO2M or MM. The group substituting the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is preferably a halogen atom, cyano groups, nitro groups, -SO3H or -CO2H. Examples of such groups include the following groups.

[0163] For example, trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-dibromoethyl, 2,2,3,3-tetrafluoropropyl, 2-ethoxyethyl, 2-butoxyethyl, 2-nitropropyl, diethylaminoethyl, (4-methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (4-nitrophenyl)methyl, (2,4-dichlorophenyl)methyl, (4-fluorophenyl)methyl, (3,5-difluorophenyl)methyl, 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl, (phenoxy)(phenyl)methyl, (benzyloxy)(phenyl)methyl, pyrrolylmethyl, pyrrolylethyl, (4-aminophenyl)methyl , (4-cyanophenyl)methyl, 2-hydroxy-1-methyl-1-phenylethyl, 2-chloro-1-methyl-1-phenylethyl; -CH2CH2OCH2CH3, -CH2CH2O(CH2)3CH3, -(CH2CH2O)2CH2CH3, -(CH2CH2O)3CH2CH3, -(CH2CH2O)4CH2CH3, -(CH2CH2O)5CH2CH3, -(CH2CH2O)6CH2CH3, -(CH2CH2O)7CH2CH3, -(CH2CH2O)8CH2CH3, -(CH2CH2O)9CH2CH3, -(CH2CH2O) 10 CH2CH3, -(CH2CH2O) 11 CH2CH3, -(CH2CH2O) 12 CH2CH3, -(CH2CH2O) 13 CH3, -CH2CH2OH, -(CH2CH2O)2H, -(CH2CH2O)3H, -(CH2CH2O)4H, -(CH2CH2O)5H, -(CH2CH2O)6H, -(CH2CH2O)7H, -(CH2CH2O)8H, -(CH2CH2O)9H, -(CH2CH2O) 10 H, -(CH2CH2O) 11 H, -(CH2CH2O) 12 H, -(CH2CH2O) 13 H, -CH2CH2OCH3, -(CH2CH2O)2CH3, -(CH2CH2O)3CH3, -(CH2CH2O)4CH3, -(CH2CH2O)5CH3, -(CH2CH2O)6CH3, -(CH2CH2O)7CH3, -(CH2CH2O)8CH3, -(CH2CH2O)9CH3, -(CH2CH2O) 10 CH3, -(CH2CH2O) 11 CH3, -(CH2CH2O) 12CH3, -(CH2CH2O) 13 A group in which -CH2- of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group such as CH3 is substituted with -O-; and an alkyl group having a substituent (hereinafter, these may be referred to as a group of group A).

[0164] For example, aryl groups having a substituent such as 4-bromophenyl, 4-nitrophenyl, 4-methoxyphenyl, 2,4-dichlorophenyl, pentafluorophenyl, 2-aminophenyl, 2-methyl-4-chlorophenyl, 4-hydroxy-1-naphthyl, 4,5,8-trichloro-2-naphthyl, anthraquinone and 2-aminoanthraquinone (hereinafter, these may be referred to as groups of group B) can be mentioned.

[0165] For example, formyl; acetyl, propionyl, butyryl, 2,2-dimethylpropionyl, pentanoyl, hexanoyl, 2-ethylhexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, heneicosanoyl, benzoyl,

[0166]

[0167] and a carbonyl group to which the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

[0168] Preferably, a carbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Group A or Group B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

[0169] More preferably, a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Group A or Group B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded is

[0170] More preferably, a carbonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned Group A or Group B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded is

[0171] Particularly preferred are carbonyl groups to which a hydrocarbon group having 1 to 12 carbon atoms, the groups of Group A and Group B described above, or the monovalent hydrocarbon group or monovalent heterocyclic group described above are bonded.

[0172] ※Indicates bonding site.

[0173] For example, there can be mentioned methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethylhexyl)oxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenoxycarbonyl, eicosyloxycarbonyl,

[0174]

[0175] and an oxycarbonyl group or the like bonded to the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group,

[0176] An oxycarbonyl group bonded to a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is preferred, an oxycarbonyl group bonded to a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is more preferred, an oxycarbonyl group bonded to a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is further preferred, and an oxycarbonyl group bonded to a hydrocarbon group having 1 to 12 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is particularly preferred. ※ indicates a bonding site.

[0177] For example, there can be mentioned formyloxy, acetyloxy, propionyloxy, butyryloxy, (2,2-dimethylpropionyl)oxy, pentanoyloxy, hexanoyloxy, (2-ethylhexanoyl)oxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy, vinylcarbonyloxy, (2-propenyl)carbonyloxy, (1-methylvinyl)carbonyloxy, and carbonyloxy groups to which the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon groups or monovalent heterocyclic groups are bonded, etc.

[0178] The carbonyloxy group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferred; the carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferred; the carbonyloxy group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is further preferred; and the carbonyloxy group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above-mentioned groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is particularly preferred.

[0179] For example, hydroxyl groups; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, neopentyloxy, 1-ethyl-1,2-dimethylpropoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethylhexyl)oxy, stearyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenoxy, benzyloxy, 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2,3-dicyanophenoxy, 2,4-dicyanophenoxy, 2,5-dicyanophenoxy, 2,6-dicyanophenoxy, 3,4-dicyanophenoxy, 3,5-Dicyanophenoxy, 4-methoxyphenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-ethoxyphenoxy, 2-ethoxyphenoxy, 3-ethoxyphenoxy; trichloromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoro-2-trifluoromethyl-2-methylpropoxy, 2-butoxyethoxy, 2-nitropropoxy, -OCH2CH2OH, -O(CH2CH2O)4H, -OCH2CF2CF2H, -OCH2CH2O(CH2)3CH3, -OCH2CH2OCH2CH3, -O(CH2CH2O)2CH2CH3, -O(CH2CH2O)4CH2CH3, -OCH2CH2O(CH2)3CH3,

[0180]

[0181]

[0182] and an oxy group to which the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

[0183] An oxy group or hydroxy group is preferably bonded to a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, more preferably bonded to a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, further preferably bonded to an oxy group or hydroxy group having 1 to 18 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, and particularly preferably bonded to an oxy group or hydroxy group having 1 to 12 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group. ※ indicates a bonding site.

[0184] For example, mercapto; methylthio, ethylthio, propylthio, butylthio, tert-butylthio, pentylthio, hexylthio, (2-ethylhexyl)thio, heptylthio, octylthio, nonylthio, decylthio, undecylthio, dodecylthio, eicosylthio, phenylthio, o-tolylthio,

[0185]

[0186] and a mercapto group in which a hydrogen atom is substituted with a group of the above-mentioned Group A or Group B or a monovalent hydrocarbon group or a monovalent heterocyclic group,

[0187] It is preferred that a hydrogen atom be substituted with a thiol group or a thiol group of a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of a monovalent hydrocarbon group or a monovalent heterocyclic group, more preferably a hydrogen atom be substituted with a thiol group or a thiol group of a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of a monovalent hydrocarbon group or a monovalent heterocyclic group, further preferably a hydrogen atom be substituted with a thiol group or a thiol group of a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of a monovalent hydrocarbon group or a monovalent heterocyclic group, and particularly preferably a hydrogen atom be substituted with a thiol group or a thiol group of a hydrocarbon group having 1 to 12 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of a monovalent hydrocarbon group or a monovalent heterocyclic group. * indicates a bonding site.

[0188] For example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethylhexyl)sulfonyl, heptylsulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, phenylsulfonyl, p-toluenesulfonyl,

[0189]

[0190] and a sulfonyl group or the like bonded to the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group,

[0191] The sulfonyl group is preferably bonded to a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, more preferably bonded to a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, further preferably bonded to a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, and particularly preferably bonded to a hydrocarbon group having 1 to 12 carbon atoms, a group of the above-mentioned Groups A to B, or a preferred group of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group. * indicates a bonding site.

[0192] For example, sulfamoyl; N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-(sec-butyl)sulfamoyl, N-(tert-butyl)sulfamoyl, N-pentylsulfamoyl, N-(1-ethylpropyl)sulfamoyl, N-hexylsulfamoyl, N-(2-ethylhexyl)sulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl; Sulfonyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-eicosylsulfamoyl group, N-phenylsulfamoyl group, -SO2NH(CH2)2N(CH2CH3)2, -SO2NHCH2CH2CH2Si(OCH2CH3)3, and sulfamoyl group substituted with one of the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group;

[0193] N,N-dimethylsulfamoyl, N-ethyl-N-methylsulfamoyl, N,N-diethylsulfamoyl, N-propyl-N-methylsulfamoyl, N,N-dipropylsulfamoyl, N-isopropyl-N-methylsulfamoyl, N,N-diisopropylsulfamoyl, N,N-diisobutylsulfamoyl, N,N-di(sec-butyl)sulfamoyl, N-(tert-butyl)-N-methylsulfamoyl, N,N-di(tert-butyl)sulfamoyl, N-butyl-N-methylsulfamoyl, N,N-dibutylsulfamoyl, N-butyl-N-octylsulfamoyl, N,N-dipentylsulfamoyl, N,N-bis(1-ethylpropyl)sulfamoyl, N-butyl-N-hexylsulfamoyl, N-hexyl-N N,N-dihexylsulfamoyl, N-(2-ethylhexyl)-N-methylsulfamoyl, N,N-bis(2-ethylhexyl)sulfamoyl, N,N-diheptylsulfamoyl, N-octyl-N-methylsulfamoyl, N,N-dioctylsulfamoyl, N,N-dinonylsulfamoyl, N-decyl-N-methylsulfamoyl, N-undecyl-N-methylsulfamoyl, N-dodecyl-N-methylsulfamoyl, N-eicosyl-N-methylsulfamoyl, N-phenyl-N-methylsulfamoyl, N,N-diphenylsulfamoyl, and a sulfamoyl group substituted with two of the groups selected from Groups A and B above, the monovalent hydrocarbon groups above, and the monovalent heterocyclic groups above, etc.

[0194] Preferably, it is substituted with one or two sulfamoyl groups selected from the group consisting of hydrocarbon groups having 1 to 30 carbon atoms, groups of the above-mentioned groups A to B, groups preferred for the above-mentioned monovalent hydrocarbon groups, and groups preferred for the above-mentioned monovalent heterocyclic groups, -SO2NH(CH2)2N(CH2CH3)2, or sulfamoyl groups; more preferably, it is substituted with one or two sulfamoyl groups selected from the group consisting of hydrocarbon groups having 1 to 20 carbon atoms, groups of the above-mentioned groups A to B, groups preferred for the above-mentioned monovalent hydrocarbon groups, and groups preferred for the above-mentioned monovalent heterocyclic groups, -SO2NH(CH2)2N(CH2CH3)2, or sulfamoyl groups; further The step is preferably substituted with one or two sulfamoyl groups selected from a hydrocarbon group having 1 to 18 carbon atoms, the groups of the above-mentioned groups A to B, the preferred groups of the above-mentioned monovalent hydrocarbon groups and the preferred groups of the above-mentioned monovalent heterocyclic groups, -SO2NH(CH2)2N(CH2CH3)2 or a sulfamoyl group, and is particularly preferably substituted with one or two sulfamoyl groups selected from a hydrocarbon group having 1 to 12 carbon atoms, the groups of the above-mentioned groups A to B, the preferred groups of the above-mentioned monovalent hydrocarbon groups and the preferred groups of the above-mentioned monovalent heterocyclic groups, -SO2NH(CH2)2N(CH2CH3)2 or a sulfamoyl group.

[0195] For example, there can be mentioned carbamoyl groups; N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-(sec-butyl)carbamoyl, N-(tert-butyl)carbamoyl, N-pentylcarbamoyl, N-(1-ethylpropyl)carbamoyl, N-hexylcarbamoyl, N-(2-ethylhexyl)carbamoyl, N-heptylcarbamoyl, N -octylcarbamoyl, N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl, -CONH(CH2)2N(CH2CH3)2, -CONHCH2CH2CH2Si(OCH2CH3)3, and carbamoyl substituted with one of the above-mentioned groups A or B or the above-mentioned monovalent hydrocarbon groups or monovalent heterocyclic groups;

[0196] N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N-propyl-N-methylcarbamoyl, N,N-dipropylcarbamoyl, N-isopropyl-N-methylcarbamoyl, N,N-diisopropylcarbamoyl, N,N-diisobutylcarbamoyl, N,N-di(sec-butyl)carbamoyl, N-(tert-butyl)-N-methylcarbamoyl, N,N-di(tert-butyl)carbamoyl, N-butyl-N-methylcarbamoyl, N,N-dibutylcarbamoyl, N-butyl-N-octylcarbamoyl, N,N-dipentylcarbamoyl, N,N-bis(1-ethylpropyl)carbamoyl, N-butyl-N-hexylcarbamoyl, N-hexyl- N-methylcarbamoyl, N,N-dihexylcarbamoyl, N-(2-ethylhexyl)-N-methylcarbamoyl, N,N-bis(2-ethylhexyl)carbamoyl, N,N-diheptylcarbamoyl, N-octyl-N-methylcarbamoyl, N,N-dioctylcarbamoyl, N,N-dinonylcarbamoyl, N-decyl-N-methylcarbamoyl, N-undecyl-N-methylcarbamoyl, N-dodecyl-N-methylcarbamoyl, N-eicosyl-N-methylcarbamoyl, N-phenyl-N-methylcarbamoyl, N,N-diphenylcarbamoyl, and carbamoyl groups substituted with two of the groups selected from Groups A and B above, the monovalent hydrocarbon groups above, and the monovalent heterocyclic groups above, etc.

[0197] Preferably, it is substituted with one or two carbamoyl groups or carbamoyl groups selected from the group consisting of hydrocarbon groups having 1 to 30 carbon atoms, groups of the above-mentioned groups A to B, groups preferred for the above-mentioned monovalent hydrocarbon groups, and groups preferred for the above-mentioned monovalent heterocyclic groups, and more preferably, it is substituted with one or two carbamoyl groups or carbamoyl groups selected from the group consisting of hydrocarbon groups having 1 to 20 carbon atoms, groups of the above-mentioned groups A to B, groups preferred for the above-mentioned monovalent hydrocarbon groups, and groups preferred for the above-mentioned monovalent heterocyclic groups, and further The step is preferably substituted with one or two carbamoyl groups or carbamoyl groups selected from a hydrocarbon group having 1 to 18 carbon atoms, the groups of the above-mentioned groups A to B, the preferred groups of the above-mentioned monovalent hydrocarbon groups and the preferred groups of the above-mentioned monovalent heterocyclic groups, and is particularly preferably substituted with one or two carbamoyl groups or carbamoyl groups selected from a hydrocarbon group having 1 to 12 carbon atoms, the groups of the above-mentioned groups A to B, the preferred groups of the above-mentioned monovalent hydrocarbon groups and the preferred groups of the above-mentioned monovalent heterocyclic groups.

[0198] For example, amino; N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-(sec-butyl)amino, N-(tert-butyl)amino, N-pentylamino, N-(1-ethylpropyl)amino, N-hexylamino, N-(2-ethylhexyl)amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-phenylamino, and amino substituted with one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon groups or monovalent heterocyclic groups;

[0199] N,N-dimethylamino, N-ethyl-N-methylamino, N,N-diethylamino, N-propyl-N-methylamino, N,N-dipropylamino, N-isopropyl-N-methylamino, N,N-diisopropylamino, N,N-diisobutylamino, N,N-di(sec-butyl)amino, N-(tert-butyl)-N-methylamino, N,N-di(tert-butyl)amino, N-butyl-N-methylamino, N,N-dibutylamino, N-butyl-N-octylamino, N,N-dipentylamino, N,N-bis(1-ethylpropyl)amino, N-butyl-N-hexylamino, N-hexyl-N-methyl N,N-dihexylamino, N-(2-ethylhexyl)-N-methylamino, N,N-bis(2-ethylhexyl)amino, N,N-diheptylamino, N-octyl-N-methylamino, N,N-dioctylamino, N,N-dinonylamino, N-decyl-N-methylamino, N-undecyl-N-methylamino, N-dodecyl-N-methylamino, N-eicosyl-N-methylamino, N-phenyl-N-methylamino, N,N-diphenylamino, and an amino group substituted with two of the groups selected from Groups A and B above, the monovalent hydrocarbon groups above, and the monovalent heterocyclic groups above, etc.

[0200] It is preferably substituted with one or two amino groups or amino groups selected from a hydrocarbon group having 1 to 30 carbon atoms, the groups of the above-mentioned groups A to B, the groups preferred for the above-mentioned monovalent hydrocarbon groups, and the groups preferred for the above-mentioned monovalent heterocyclic groups. It is more preferably substituted with one or two amino groups or amino groups selected from a hydrocarbon group having 1 to 20 carbon atoms, the groups of the above-mentioned groups A to B, the groups preferred for the above-mentioned monovalent hydrocarbon groups, and the groups preferred for the above-mentioned monovalent heterocyclic groups. It is further preferably substituted with one or two amino groups or amino groups selected from a hydrocarbon group having 1 to 18 carbon atoms, the groups of the above-mentioned groups A to B, the groups preferred for the above-mentioned monovalent hydrocarbon groups, and the groups preferred for the above-mentioned monovalent heterocyclic groups. It is particularly preferably substituted with one or two amino groups or amino groups selected from a hydrocarbon group having 1 to 12 carbon atoms, the groups of the above-mentioned groups A to B, the groups preferred for the above-mentioned monovalent hydrocarbon groups, and the groups preferred for the above-mentioned monovalent heterocyclic groups.

[0201] For example, formylamino; acetylamino, propionylamino, butyrylamino, (2,2-dimethylpropionyl)amino, pentanoylamino, hexanoylamino, (2-ethylhexanoyl)amino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino,

[0202]

[0203] and a carbonylamino group to which the above-mentioned groups A and B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

[0204] The carbonylamino group is preferably bonded to a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Groups A to B, or a group preferably selected from the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, more preferably bonded to a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Groups A to B, or a group preferably selected from the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, further preferably bonded to a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned Groups A to B, or a group preferably selected from the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, and particularly preferably bonded to a hydrocarbon group having 1 to 12 carbon atoms, a group of the above-mentioned Groups A to B, or a group preferably selected from the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group. ※ indicates a bonding site.

[0205] For example, -SiH3; -Si(CH3)3, -Si(CH2CH3)3, -Si((CH2)2CH3)3, -Si(CH(CH3)2)3, -Si((CH2)3CH3)3, -Si((CH2)4CH3)3, -Si((CH2)5CH3)3, -Si((CH2)6CH3)3, -Si((CH2)7CH3)3, -Si((CH2)8CH3)3, -Si((CH2)9CH3)3, -Si((CH2) 10 CH3)3, -Si((CH2) 11 CH3)3, -Si((CH2) 12 CH3)3, -Si(C6H5)3, -Si(C 10 H7)3, -Si(CH3)2(CH2CH3), -Si(CH3)2((CH2)2CH3), -Si(CH3)2(CH(CH3)2), -Si(CH3)2((CH2)3C H3), -Si(CH3)2((CH2)5CH3), -Si(CH3)2((CH2)7CH3), -Si(CH3)2((CH2)9CH3), -Si(CH3)2((CH2) 11CH3)、-Si(CH3)2((CH2) 13 CH3)、-Si(CH3)2((CH2) 15 CH3)、-Si(CH3)2((CH2) 17 CH3)、-Si(CH3)2((CH2) 19 CH3)、-Si(CH3)2((CH2) 29 CH3), -Si(CH3)2(C6H5), -Si(CH3)(C6H5)2, -Si(CH3)2(C 10 H7), and -SiH3 substituted with one, two or three of the groups selected from the above-mentioned groups A and B, the above-mentioned monovalent hydrocarbon groups and the above-mentioned monovalent heterocyclic groups;

[0206] -Si(OH)3; -Si(OCH3)3, -Si(OCH2CH3)3, -Si(O(CH2)2CH3)3, -Si(OCH(CH3)2)3, -Si(O(CH2)3CH3)3, -Si(O(CH2)4CH3 )3, -Si(O(CH2)5CH3)3, -Si(O(CH2)6CH3)3, -Si(O(CH2)7CH3)3, -Si(O(CH2)8CH3)3, -Si(O(CH2)9CH3)3, -Si(O(CH2) 10 CH3)3, -Si(O(CH2) 11 CH3)3, -Si(OC6H5)3, -Si(OC 10 H7)3, -Si(OCH3)2(OCH2CH3), -Si(OCH3)2(O(CH2)2CH3), -Si(OCH3)2(OCH(CH3)2), -Si(OCH3)2(O(CH2)3C H3), -Si(OCH3)2(O(CH2)5CH3), -Si(OCH3)2(O(CH2)7CH3), -Si(OCH3)2(O(CH2)9CH3), -Si(OCH3)2(O(CH2) 11 CH3)、-Si(OCH3)2(O(CH2) 13 CH3)、-Si(OCH3)2(O(CH2) 15 CH3)、-Si(OCH3)2(O(CH2) 17 CH3)、-Si(OCH3)2(O(CH2) 19 CH3)、-Si(OCH3)2(O(CH2) 29CH3), -Si(OCH3)2(OC6H5), -Si(OCH3)(OC6H5)2, -Si(OCH3)2(OC 10 H7), and -Si(OH)3 substituted with one, two or three of the groups selected from the above-mentioned groups A and B, the above-mentioned monovalent hydrocarbon groups and the above-mentioned monovalent heterocyclic groups;

[0207] -SiH(OH)2; -Si(CH3)(OCH3)2, -Si((CH2) 11 CH3)(O(CH2) 11 CH3)2, -Si(C6H5)(OC6H5)2, -Si(CH3)(OH)2, -Si((CH2) 36 CH3)(OH)2, -Si(C6H5)(OH)2, and -SiH(OH)2 substituted with one, two or three of the groups selected from Group A and Group B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups;

[0208] -SiH2(OH); -Si(CH3)2(OCH3), -Si((CH2) 11 CH3)2(O(CH2) 11 CH3), -Si(C6H5)2(OC6H5), -Si(CH3)2(OH), -Si((CH2) 17 CH3)2(OH), -Si(C6H5)2(OH), and -SiH2(OH) substituted with one, two or three of the groups selected from the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups and the above-mentioned monovalent heterocyclic groups.

[0209] Preferably, it is substituted with one, two or three -SiH3, -Si(OH)3, -SiH(OH)2 and -SiH2(OH), or -Si(OH)3 selected from a hydrocarbon group having 1 to 30 carbon atoms, a group of the above-mentioned Group A to Group B, a preferred group of the above-mentioned monovalent hydrocarbon group and a preferred group of the above-mentioned monovalent heterocyclic group, more preferably substituted with one, two or three -SiH3, -Si(OH)3, -SiH(OH)2 and -SiH2(OH), or -Si(OH)3 selected from a hydrocarbon group having 1 to 20 carbon atoms, a group of the above-mentioned Group A to Group B, a preferred group of the above-mentioned monovalent hydrocarbon group and a preferred group of the above-mentioned monovalent heterocyclic group, and further The step is preferably substituted with one, two or three -SiH3, -Si(OH)3, -SiH(OH)2 and -SiH2(OH), or -Si(OH)3 selected from a hydrocarbon group having 1 to 18 carbon atoms, a group of the above-mentioned Group A to Group B, a preferred group for the above-mentioned monovalent hydrocarbon group and a preferred group for the above-mentioned monovalent heterocyclic group, and is particularly preferably substituted with one, two or three -SiH3, -Si(OH)3, -SiH(OH)2 and -SiH2(OH), or -Si(OH)3 selected from a hydrocarbon group having 1 to 12 carbon atoms, a group of the above-mentioned Group A to Group B, a preferred group for the above-mentioned monovalent hydrocarbon group and a preferred group for the above-mentioned monovalent heterocyclic group.

[0210] For example, there can be mentioned a phthalimidomethyl group (C6H4(CO)2N—CH2—) which may have a substituent, and as the substituent, there can be mentioned at least one selected from the above-mentioned halogen atom, the above-mentioned group A to group B groups, the above-mentioned monovalent hydrocarbon group and the above-mentioned monovalent heterocyclic group.

[0211] As other groups, -SCOCH3,

[0212] Etc. ※Indicates a bonding site.

[0213] The monovalent hydrocarbon group or the monovalent heterocyclic group may be substituted with -SO3 - N + (C 12 H 25 )(CH3)3, -CO2 - N + (C 12 H 25 )(CH3)3, -SO3 - , -CO2 - wait.

[0214] R 1 and R 2 , R 2 and R 3 , and R3 and R 4 They may be bonded to each other to form a ring.

[0215] Examples of the alkali metal atom represented by M and MM include alkali metal atoms such as a lithium atom, a sodium atom and a potassium atom.

[0216] Examples of the metal atom that may have a ligand represented by M and MM include metal atoms belonging to Groups IIA to VA of the periodic table. More preferred metal atoms that may have a ligand include Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, and Ge, and further preferred are Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, and Cr, and particularly preferred are Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, and Cr.

[0217] As M and MM represent N(Z 1 )(Z 2 )(Z 3 )(Z 4 ), NH4; NH3((CH2)7CH3), NH3((CH2) 11 CH3)、NH3((CH2) 17 CH3) and other NH4 substituted with an alkyl group; N(CH3)3((CH2) 15 CH3)、N(CH3)3((CH2) 11 CH3)、N(CH3)2((CH2) 11 CH3)2、N(CH3)2((CH2) 17 CH3)2, etc. NH4 substituted with 4 alkyl groups; and NH4 substituted with 1, 2, 3 or 4 groups selected from the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups and the above-mentioned monovalent heterocyclic groups.

[0218] M is preferably a hydrogen atom; an alkali metal atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH4; NH3((CH2)7CH3), NH3((CH2) 11 CH3)、NH3((CH2) 17CH3) and other NH4 substituted with an alkyl group; N(CH3)3((CH2) 15 CH3)、N(CH3)3((CH2) 11 CH3)、N(CH3)2((CH2) 11 CH3)2、N(CH3)2((CH2) 17 CH3)2 and other NH4 substituted with 4 alkyl groups,

[0219] More preferably, a hydrogen atom; a sodium atom, a potassium atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH4; NH3((CH2)7CH3), NH3((CH2) 11 CH3)、NH3((CH2) 17 CH3) and other NH4 substituted with an alkyl group; N(CH3)3((CH2) 15 CH3)、N(CH3)3((CH2) 11 CH3)、N(CH3)2((CH2) 11 CH3)2、N(CH3)2((CH2) 17 A group substituted with 4 alkyl groups on NH4 such as CH3)2.

[0220] MM is preferably an alkali metal atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH4; NH3((CH2)7CH3), NH3((CH2) 11 CH3)、NH3((CH2) 17 CH3) and other NH4 substituted with an alkyl group; N(CH3)3((CH2) 15 CH3)、N(CH3)3((CH2) 11 CH3)、N(CH3)2((CH2) 11 CH3)2、N(CH3)2((CH2) 17 CH3)2 and other NH4 substituted with 4 alkyl groups,

[0221] More preferably, a sodium atom or a potassium atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH4; NH3((CH2)7CH3), NH3((CH2) 11 CH3)、NH3((CH2) 17 CH3) etc. NH4 is substituted with an alkyl group; N(CH3)3((CH2) 15 CH3)、N(CH3)3((CH2) 11 CH3)、N(CH3)2((CH2) 11 CH3)2、N(CH3)2((CH2) 17 A group substituted with 4 alkyl groups on NH4 such as CH3)2.

[0222] Q 1 and Q 2 Each may independently represent a divalent hydrocarbon group or a divalent heterocyclic group, the -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, the -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -N(-)-, the -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -N=, the -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by halogen atoms, cyano groups, nitro groups, -SO3M, -CO2M or MM.

[0223] Q 1 and Q 2 Preferred are groups represented by formula (QQ1) to formula (QQ19).

[0224]

[0225]

[0226] [In formula (QQ1) to formula (QQ19), R Q1 ~R Q94Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, wherein -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, wherein -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=, wherein -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O)2- or -CO-, and wherein the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM. R Q1 ~R Q94 can be selected from R Q1 ~R Q94 One or more of them are bonded to form a ring. M and MM have the same meanings as above. ※ indicates a bonding site. ]

[0227] As R Q1 ~R Q94 A monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by R, wherein -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N=, -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM, and examples thereof include groups corresponding to R 1 ~R 5 and Z 1 ~Z 4 The monovalent hydrocarbon group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by the above-mentioned group is a group in which -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N=, -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or the same group as MM.

[0228] As R Q1 ~R Q94Preferred groups include those with R 1 ~R 5 and Z 1 ~Z 4 Preferred groups are the same groups.

[0229] Q 1 and Q 2 Preferred are groups represented by formula (QQ1) to formula (QQ12), more preferred are groups represented by formula (QQ1) to formula (QQ5), further preferred are groups represented by formula (QQ1) to formula (QQ4), particularly preferred are groups represented by formula (QQ1) and formula (QQ2), and further preferred are groups represented by formula (QQ2).

[0230] As formula (QQ1) to formula (QQ19), for example, the following formulas (Qa1) to (Qa50) can be cited; formula (Qb1) to (Qb27); formula (Qc1) to (Qc56); formula (Qd1) to (Qd41); formula (Qe1) to (Qe16); formula (Qf1) to (Qf15); formula (Qg1) to (Qg40); formula (Qh1) to (Qh40); formula (Qj1) to (Qj29); formula (Qk1) to (Qk22); formula (Qm1) ) to (Qm20); (Qn1) to (Qn16); (Qo1) to (Qo15); (Qp1) to (Qp83); (Qq1) to (Qq72); (Qr1) to (Qr17); (Qs1) to (Qs26); (Qt1) to (Qt26); (Qu1) to (Qu17); (Qv1) to (Qv26); (Qx1) to (Qx2); and (Qy1) to (Qy10) and the like. In which, ※ represents a bonding site.

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] Q 1 and Q 2 At least one of them is a group represented by formula (QQ20).

[0261]

[0262] [In the formula (QQ20), p is an integer greater than or equal to 0, q is an integer greater than or equal to 0, and the sum of p and q is an integer greater than or equal to 1.

[0263] L represents a (2p+2q+2)-valent hydrocarbon group or a (2p+2q+2)-valent heterocyclic group, wherein the -C(-)(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted by -Si(-)(-)-, the -CH(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted by -N(-)-, and the -CH(-)- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted by -N(-)-. The -CH= of the (2p+2q+2)-valent heterocyclic group may be substituted by -N=, the -CH2- constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the (2p+2q+2)-valent hydrocarbon group and the (2p+2q+2)-valent heterocyclic group may be substituted by halogen atoms, cyano, nitro, -SO3M, -CO2M or MM.

[0264] Q 3 and Q 4 Each independently represents a divalent hydrocarbon group or a divalent heterocyclic group, the -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, the -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -N(-)-, the -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -N=, the -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by halogen atoms, cyano groups, nitro groups, -SO3M, -CO2M or MM.

[0265] R Q95 ~R Q104 Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms, and the -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, the -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N(-)-, the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N=, the -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM.

[0266] R Q95 ~R Q104 can be selected from R Q95 ~R Q104 One or more of them are bonded to each other to form a ring.

[0267] M and MM have the same meanings as described above.

[0268] ※Indicates bonding site.

[0269] Q 3 , Q 4 , R Q95 ~R Q104 When , M and MM exist in plural numbers, they may be the same as or different from each other. ]

[0270] p in formula (QQ20) is an integer greater than 0, preferably an integer from 0 to 11, more preferably an integer from 0 to 5, further preferably an integer from 0 to 3, particularly preferably an integer from 0 to 2, and further preferably an integer from 0 to 1. q in formula (QQ20) is an integer greater than 0, preferably an integer from 0 to 11, more preferably an integer from 0 to 5, further preferably an integer from 0 to 3, particularly preferably an integer from 0 to 2, and further preferably an integer from 0 to 1. The sum of p and q in formula (QQ20) is preferably an integer from 1 to 11, more preferably an integer from 1 to 5, further preferably an integer from 1 to 3, particularly preferably an integer from 1 to 2, and further preferably an integer of 1.

[0271] Q 3 and Q 4 Each independently represents a divalent hydrocarbon group or a divalent heterocyclic group, the -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, the -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -N(-)-, the -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -N=, the -CH2- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted by halogen atoms, cyano groups, nitro groups, -SO3M, -CO2M or MM.

[0272] Q 3 and Q 4 Preferred are groups represented by formula (QQ1) to formula (QQ19), more preferred are groups represented by formula (QQ1) to formula (QQ12), further preferred are groups represented by formula (QQ1) to formula (QQ5), particularly preferred are groups represented by formula (QQ1) to formula (QQ4), further preferred are groups represented by formula (QQ1) and formula (QQ2), and particularly preferred are groups represented by formula (QQ2).

[0273] Q 3 and Q 4Preferred are groups represented by formula (QQ1) to formula (QQ19), and examples of the formula (QQ1) to formula (QQ19) include formula (Qa1) to formula (Qa50); formula (Qb1) to formula (Qb27); formula (Qc1) to formula (Qc56); formula (Qd1) to formula (Qd41); formula (Qe1) to formula (Qe16); formula (Qf1) to formula (Qf15); formula (Qg1) to formula (Qg40); formula (Qh1) to formula (Qh40); formula (Qj1) to formula (Qj29); formula (Qk1) to formula (Q k22); Formula (Qm1) to Formula (Qm20); Formula (Qn1) to Formula (Qn16); Formula (Qо1) to Formula (Qо15); Formula (Qp1) to Formula (Qp83); Formula (Qq1) to Formula (Qq72); Formula (Qr1) to Formula (Qr17); Formula (Qs1) to Formula (Qs26); Formula (Qt1) to Formula (Qt26); Formula (Qu1) to Formula (Qu17); Formula (Qv1) to Formula (Qv26); Formula (Qx1) to Formula (Qx2); and groups represented by Formula (Qy1) to Formula (Qy10), etc., wherein ※ represents a bonding site.

[0274] As R Q95 ~R Q104 A monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by R, wherein -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N=, -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or MM, and examples thereof include groups corresponding to R 1 ~R 5 and Z 1 ~Z 4 The monovalent hydrocarbon group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by the above-mentioned group is a group in which -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -N=, -CH2- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O)2- or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO3M, -CO2M or the same group as MM.

[0275] As R Q95 ~R Q104 Preferred groups include those with R 1 ~R 5 and Z 1 ~Z 4 Preferred groups are the same groups.

[0276] As the group represented by L, for example, there can be mentioned the following formulas (da1) to (da27); formulas (db1) to (db16); formulas (dc1) to (dc52); formulas (dd1) to (dd68); formulas (de1) to (de86); formulas (df1) to (df3); formulas (dh1) to (dh13); and groups represented by formula (dr21), their tautomers, groups in which hydrogen atoms contained in these groups are substituted with halogen atoms, methyl groups, methoxy groups, trifluoromethyl groups or trifluoromethoxy groups, and groups in which at least one hydrogen atom in -CO2H and -SO3H contained in these groups is substituted with an alkali metal atom such as a lithium atom, a sodium atom or a potassium atom. Wherein, b1 to b6 represent bonding sites.

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295] Examples of compound (I) include compounds represented by formula (Ip) shown in Tables p1 to p22 below or alkali metal salts thereof. The compound represented by formula (Ip) may be combined with Q in the compound represented by formula (I). 2 The compounds are the same when they are groups represented by the formula (QQ20) and p=0 and q=1.

[0296] It should be noted that the “Q d+1 ” column, “Q d11 ” column, “Q d21 ” column and “L 1 The symbols described in the " column correspond to the groups represented by the above formulas, respectively.

[0297] "Q" in Tables p1 to p22 d+1 The column " indicates Q in the compound represented by formula (Ip) d11 The groups and Q d21 The group represented by "Q d+1 The group corresponding to the symbol recorded in the " column.

[0298] ※ and b1 to b4 indicate bonding sites.

[0299] In formula (Ip), C b11 , C b21 , C b31 , C b41 Respectively represent and L 1 The carbon atom forming the bond, in the groups represented by formula (da1) to (da27); formula (db1) to (db16); formula (dc1) to (dc52); formula (dd1) to (dd68); formula (de1) to (de86); and formula (dh1) to (dh13), the bonding site represented by b1 is b11 The bonding site represented by b2 forms a bond with C b21 The bonding site represented by b3 forms a bond with C b31 The bonding site represented by b4 forms a bond with C b41 Form a bond.

[0300] Q d11 and Q d21 Each independently represents a divalent hydrocarbon group or a divalent heterocyclic group, and may be 1 and Q 2The same groups as the divalent hydrocarbon groups or divalent heterocyclic groups represented by .

[0301]

[0302] [Table p1]

[0303]

[0304] [Table p2]

[0305]

[0306] [Table p3]

[0307]

[0308] [Table p4]

[0309]

[0310] [Table P5]

[0311]

[0312] [Table p6]

[0313]

[0314] [Table p7]

[0315]

[0316] [Table P8]

[0317]

[0318] [Table p9]

[0319]

[0320] [Table p10]

[0321]

[0322] [Table p11]

[0323]

[0324] [Table p12]

[0325]

[0326] [Table P13]

[0327]

[0328] [Table P14]

[0329]

[0330] [Table p15]

[0331]

[0332] [Table P16]

[0333]

[0334] [Table p17]

[0335]

[0336] [Table p18]

[0337]

[0338] [Table p19]

[0339]

[0340] [Table p20]

[0341]

[0342] [Table p21]

[0343]

[0344] [Table p22]

[0345]

[0346] In the compound represented by formula (Ip), Q d11 and Q d21 Each is independently preferably a divalent hydrocarbon group, more preferably a group represented by formula (QQ1) to formula (QQ7), further preferably a group represented by formula (QQ1) to formula (QQ4), and further preferably a group represented by formula (QQ1) or a group represented by formula (QQ2).

[0347] L 1 Preferred are groups represented by formulae (da1) to (da27) and groups represented by formulae (de1) to (de86), and more preferred are groups represented by formula (da4), groups represented by formula (da16), groups represented by formula (de1) or groups represented by formula (de86).

[0348] Examples of the compound (I) include compounds represented by the formula (Iq) shown in Table q1 to Table q22 below or alkali metal salts thereof.

[0349] The compound represented by formula (Iq) can be combined with Q in the compound represented by formula (I) 1 The compounds are the same when they are groups represented by the formula (QQ20) and p=0 and q=1.

[0350] It should be noted that the “Q d+2 ” column, “Q d12 ” column, “Q d22 ” column and “L 2 The symbols described in the " column correspond to the groups represented by the above formulas, respectively.

[0351] "Q" in Tables q11 to q22 d+2 The column " represents Q in the compound represented by formula (Iq) d12 The groups and Q d22 The group represented by "Q d+2 The group corresponding to the symbol recorded in the " column.

[0352] ※ and b1 to b4 indicate bonding sites.

[0353] In formula (Iq), C b12 , C b22 , C b32 , C b42 Respectively represent and L 2 The carbon atom forming the bond, in the groups represented by formula (da1) to (da27); formula (db1) to (db16); formula (dc1) to (dc52); formula (dd1) to (dd68); formula (de1) to (de86); and formula (dh1) to (dh13), the bonding site represented by b1 is b12 The bonding site represented by b2 forms a bond with C b22 The bonding site represented by b3 forms a bond with C b32 The bonding site represented by b4 forms a bond with C b42 Form a bond.

[0354] Q d12 and Q d22 Each independently represents a divalent hydrocarbon group or a divalent heterocyclic group, and may be 1 and Q 2 The same groups as the divalent hydrocarbon groups or divalent heterocyclic groups represented by .

[0355]

[0356] [Table q1]

[0357]

[0358] [Table q2]

[0359]

[0360] [Table q3]

[0361]

[0362] [Table q4]

[0363] [Table q5]

[0364]

[0365] [Table q6]

[0366]

[0367] [Table q7]

[0368]

[0369] [Table q8]

[0370]

[0371] [Table q9]

[0372]

[0373] [Table q10]

[0374]

[0375] [Table q11]

[0376]

[0377] [Table q12]

[0378]

[0379] [Table q13]

[0380]

[0381] [Table q14]

[0382]

[0383] [Table q15]

[0384]

[0385] [Table q16]

[0386]

[0387] [Table q17]

[0388]

[0389] [Table q18]

[0390]

[0391] [Table q19]

[0392]

[0393] [Table q20]

[0394]

[0395] [Table q21]

[0396]

[0397] [Table q22]

[0398]

[0399] Examples of the compound (I) include compounds represented by the formula (Ir) shown in Table r1 to Table r23 below, or alkali metal salts thereof.

[0400] The compound represented by formula (Ir) can be combined with Q in the compound represented by formula (I) 1 The compounds are the same when they are groups represented by the formula (QQ20) and p=1 and q=0.

[0401] It should be noted that the "Q d+3 ” column, “Q d13 ” column, “Q d23 ” column and “L 3 The symbols described in the "" column correspond to the groups represented by the above formula and the groups represented by the following formulae (dr1) to (dr22), respectively.

[0402] "Q d+3 The column " represents Q in the compound represented by formula (Ir) d13 The groups and Q d23 The group represented by "Q d+3 The group corresponding to the symbol recorded in the " column.

[0403] ※ and b1 to b4 indicate bonding sites.

[0404] In formula (Ir), C b13 , C b23 , C b33, C b43 Respectively represent and L 3 The carbon atom forming the bond, in the groups represented by formula (da1) to (da27); formula (db1) to (db16); formula (dc1) to (dc52); formula (dd1) to (dd68); formula (de1) to (de86); formula (dh1) to (dh13); and formula (dr1) to (dr22), the bonding site represented by b1 is in contact with C b13 The bonding site represented by b2 forms a bond with C b23 The bonding site represented by b3 forms a bond with C b33 The bonding site represented by b4 forms a bond with C b43 Form a bond.

[0405] Q d13 and Q d23 Each independently represents a divalent hydrocarbon group or a divalent heterocyclic group, and may be 1 and Q 2 The same groups as the divalent hydrocarbon groups or divalent heterocyclic groups represented by .

[0406]

[0407]

[0408] [Table r1]

[0409]

[0410] [Table r2]

[0411]

[0412] [Table r3]

[0413]

[0414] [Table r4]

[0415]

[0416] [Table r5]

[0417]

[0418] [Table r6]

[0419]

[0420] [Table r7]

[0421]

[0422] [Table r8]

[0423]

[0424] [Table r9]

[0425]

[0426] [Table r10]

[0427]

[0428] [Table r11]

[0429]

[0430] [Table r12]

[0431]

[0432] [Table r13]

[0433]

[0434] [Table r14]

[0435]

[0436] [Table r15]

[0437]

[0438] [Table r16]

[0439]

[0440] [Table r17]

[0441]

[0442] [Table r18]

[0443]

[0444] [Table r19]

[0445]

[0446] [Table r20]

[0447]

[0448] [Table r21]

[0449]

[0450] [Table r22]

[0451]

[0452] [Table r23]

[0453]

[0454] Examples of the compound (I) include compounds represented by the formula (Iw) shown in the following Table w1 and alkali metal salts thereof.

[0455] It should be noted that the "tu" column and "Q 1 "Bar and "Q 2 The symbols recorded in the " column correspond to the groups represented by the above chemical formula and the groups represented by the following formulas (tu1) to (tu100), respectively.

[0456] In the groups represented by the following formulae (tu1) to (tu100), # represents 1 The bonding site of Q 2 bonding site.

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478] [Table w1]

[0479]

[0480] Examples of compound (I) include compounds represented by formula (Ip1) to (Ip5932), (Ip6000), compounds represented by formula (Iq1) to (Iq5932), compounds represented by formula (Ir1) to (Ir6242), and compounds represented by formula (1w1) to (1w200) in which a substituted group selected from -SO3H, -CO2H, -SO3NH4, -CO2NH4, -SO2NH2, -CONH2, phthalimidomethyl (C6H4(CO)2N-CH2-), -SO2NH(CH2)2N(CH2CH3)2, -N(CH3)((CH2) 11 CH3), a compound containing one or more of a fluorine atom, a chlorine atom and a bromine atom.

[0481] Examples of compound (I) include compounds represented by formula (Ip1) to (Ip5932), (Ip6000), compounds represented by formula (Iq1) to (Iq5932), compounds represented by formula (Ir1) to (Ir6242), and compounds represented by formula (Iw1) to (Iw200) substituted with 1 to 6 groups selected from -SO3H, -CO2H, -SO3NH4, -CO2NH4, -SO2NH2, -CONH2, phthalimidomethyl (C6H4(CO)2N-CH2-), -SO2NH(CH2)2N(CH2CH3)2, -N(CH3)((CH2) 11 CH3), a compound containing one or more of a fluorine atom, a chlorine atom and a bromine atom.

[0482] Examples of compound (I) include compounds represented by formula (Ip1) to (Ip5932), (Ip6000), compounds represented by formula (Iq1) to (Iq5932), compounds represented by formula (Ir1) to (Ir6242), and compounds represented by formula (Iw1) to (Iw200) substituted with a -SO3 - and -CO2 - Anions selected from Mg 2 + , Ca 2+ , Sr 2+ , Ba 2+ 、Ni 2+ 、Zn 2+ , Fe 2+ 、Co 2+ Sn 2+ , Mn 2+ 、Al 3+ , Fe 3+ Cr 3+ Sn 4+ , Mn 4+ , Cu 2+ , Li + 、Na + and K + A metal salt composed of one or more cations.

[0483] As compound (I), compounds represented by formula (Ip1) to formula (Ip3198); compounds represented by formula (Ip3997) to formula (Ip5253), and formula (Ip6000); compounds represented by formula (Iq1) to formula (Iq3198); compounds represented by formula (Iq3997) to formula (Iq5253); compounds represented by formula (Ir1) to formula (Ir3486); compounds represented by formula (Ir4305) to formula (Ir5563); compounds represented by formula (Iw1) to formula (Iw200); compounds represented by formula (Ip1) to formula (Ip3198); compounds represented by formula (Ip3997) to formula (Ip5253), and formula (Ip6000); 00), compounds represented by formula (Iq1) to (Iq3198), compounds represented by formula (Iq3997) to (Iq5253), compounds represented by formula (Ir1) to (Ir3486), compounds represented by formula (Ir4305) to (Ir5563), and compounds represented by formula (Iw1) to (Iw200) are substituted with -SO3H, -CO2H, -SO3NH4, -CO2NH4, -SO2NH2, -CONH2, phthalimidomethyl (C6H4(CO)2N-CH2-), -SO2NH(CH2)2N(CH2CH3)2, -N(CH3)((CH2) 11 CH3), a compound having one or more of a fluorine atom, a chlorine atom and a bromine atom; and a compound represented by formula (Ip1) to formula (Ip3198), a compound represented by formula (Ip3997) to formula (Ip5253), a compound represented by formula (Ip6000), a compound represented by formula (Iq1) to formula (Iq3198), a compound represented by formula (Iq3997) to formula (Iq5253), a compound represented by formula (Ir1) to formula (Ir3486), a compound represented by formula (Ir4305) to formula (Ir5563) and a compound represented by formula (Iw1) to formula (Iw200) substituted with -SO3 - and -CO2 - Anions selected from Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ 、Ni 2+ 、Zn 2+ , Fe 2+ 、Co 2+ Sn 2+ , Mn 2+ 、Al 3+ , Fe 3+ Cr 3 + Sn 4+ , Mn4+ , Cu 2+ , Li + 、Na + and K + A metal salt composed of one or more cations.

[0484] More preferably, the compounds represented by formula (Ip1) to (Ip3198); the compounds represented by formula (Ip3997) to (Ip5253), and (Ip6000); the compounds represented by formula (Iq1) to (Iq3198); the compounds represented by formula (Iq3997) to (Iq5253); the compounds represented by formula (Ir1) to (Ir3486); the compounds represented by formula (Ir4305) to (Ir5563); the compounds represented by formula (Iw1) to (Iw200); the compounds represented by formula (Ip1) to (Ip3198), and the compounds represented by formula ( Compounds represented by formula (Ip3997) to formula (Ip5253), compounds represented by formula (Ip6000), compounds represented by formula (Iq1) to formula (Iq3198), compounds represented by formula (Iq3997) to formula (Iq5253), compounds represented by formula (Ir1) to formula (Ir3486), compounds represented by formula (Ir4305) to formula (Ir5563) and compounds represented by formula (Iw1) to formula (Iw200) are substituted with one or more atoms selected from -SO3H, -CO2H, -SO3NH4, -CO2NH4, fluorine atoms, chlorine atoms and bromine atoms.

[0485] More preferred are compounds represented by formula (Ip1) to (Ip3198); compounds represented by formula (Ip3997) to (Ip5253) and formula (Ip6000); compounds represented by formula (Iq1) to (Iq3198); compounds represented by formula (Iq3997) to (Iq5253); compounds represented by formula (Ir1) to (Ir3486); compounds represented by formula (Ir4305) to (Ir5563); compounds represented by formula (Iw1) to (Iw200); compounds represented by formula (Ip1) to (Ip3198) , compounds represented by formula (Ip3997) to (Ip5253), compounds represented by formula (Ip6000), compounds represented by formula (Iq1) to (Iq3198), compounds represented by formula (Iq3997) to (Iq5253), compounds represented by formula (Ir1) to (Ir3486), compounds represented by formula (Ir4305) to (Ir5563) and compounds represented by formula (Iw1) to (Iw200), which are substituted with one or more atoms selected from -SO3H, -CO2H, -SO3NH4, -CO2NH4, chlorine atoms and bromine atoms.

[0486] Particularly preferred are compounds represented by formula (Ip1) to (Ip3198); compounds represented by formula (Ip3997) to (Ip5253) and (Ip6000); compounds represented by formula (Iq1) to (Iq3198); compounds represented by formula (Iq3997) to (Iq5253); compounds represented by formula (Ir1) to (Ir3486); and compounds represented by formula (Ir4305) to (Ir5563); and compounds represented by formula (Iw1) to (Iw200).

[0487] Compound (I) may be a compound represented by formula (Ip), a compound represented by formula (Iq), a compound represented by formula (Ir), or a compound represented by formula (Iw). Compounds represented by formula (Ip1) to (Ip3198) and compounds represented by formula (Ip3997) to (Ip5253) and (Ip6000) are particularly preferred.

[0488] The most preferred are the compound represented by formula (Ip4), the compound represented by formula (Ip16), the compound represented by formula (Ip164), the compound represented by formula (Ip412), the compound represented by formula (Ip1156), and the compound represented by formula (Ip6000).

[0489] The compound of the present invention can be synthesized, for example, using a compound represented by formula (IM1), a compound represented by formula (IM2), a compound represented by formula (IM3), a compound represented by formula (IM4), or a compound represented by formula (pt-L) as described below.

[0490] The compound represented by formula (IM1) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt2) to produce a compound represented by formula (I') (hereinafter sometimes referred to as compound (I')), and then the compound represented by formula (I') is hydrolyzed in the presence of a base to produce a compound represented by formula (IM1) (hereinafter sometimes referred to as compound (IM1)).

[0491]

[0492]

[0493] In formula (pt1), formula (pt2), formula (I') and formula (IM1), R 1 ~R 5 , Q 1 Means the same as above.

[0494] The amount of the compound represented by formula (pt2) used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is generally 0.1 to 60 mol, preferably 1 to 40 mol, more preferably 1 to 32 mol, and further preferably 2 to 20 mol, relative to 1 mol of the compound represented by formula (pt1).

[0495] The reaction temperature of the compound represented by formula (pt1) and the compound represented by formula (pt2) is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, further preferably 100 to 230°C, particularly preferably 150 to 200°C.

[0496] The reaction time of the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 0.5 to 500 hours.

[0497] The reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually carried out in the presence of a solvent.

[0498] Examples of the solvent in the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; Aliphatic hydrocarbon solvents such as alkane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.

[0499] Preferred examples include diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0500] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, and N-methylpyrrolidone are mentioned.

[0501] More preferably, methyl benzoate is used.

[0502] The amount of the solvent used in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 1 to 1000 parts by mass based on 1 part by mass of the compound represented by the formula (pt1).

[0503] In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), it is preferred that at least one selected from the group consisting of an acid and a metal salt coexists.

[0504] As the acid in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), there can be mentioned inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid, etc.; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid, and further preferably benzoic acid.

[0505] The amount of the acid used in the reaction of the compound represented by formula (pt1) and the compound represented by formula (pt2) is usually 1 to 90 mol, preferably 1 to 70 mol, more preferably 1 to 50 mol, and further preferably 1 to 30 mol, relative to 1 mol of the compound represented by formula (pt1).

[0506] Examples of the metal salt used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) include zinc chloride and aluminum chloride.

[0507] The amount of the metal salt used in the reaction of the compound represented by formula (pt1) and the compound represented by formula (pt2) is generally 0.01 to 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, and further preferably 0.01 to 3 mol, relative to 1 mol of the compound represented by formula (pt1).

[0508] The method for extracting the compound represented by formula (I') from the reaction mixture in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is not particularly limited, and the compound can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is added to a solvent such as methanol in which compound (I') in the reaction mixture is not easily soluble but compounds other than compound (I') are easily soluble, and after sufficient mixing, the compound (I') is filtered, thereby extracting the compound (I'). In addition, the compound (I') can be extracted by washing the obtained residue with an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and / or an acidic aqueous solution such as hydrochloric acid, and then washing with water, methanol, a low-boiling alcohol, or a mixed solvent thereof using an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, or a mixed solvent thereof. The compound (I') can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and / or recrystallization, or after the reaction is completed, the reaction mixture can be purified by column chromatography and / or recrystallization. After the reaction is completed, the reaction mixture is added to a solvent such as methanol in which the compound (I') in the reaction mixture is not easily soluble and the compounds other than the compound (I') are easily soluble, and after sufficient mixing, the reaction mixture is filtered, thereby extracting the compound (I'). It can be further purified by column chromatography and / or recrystallization.

[0509] Examples of the base in the hydrolysis reaction of the compound represented by the formula (I') in the presence of a base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,5-diazabicyclo[4.3.0]non-5-ene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium; and inorganic bases such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide. Inorganic bases are preferred, lithium hydroxide, sodium hydroxide and potassium hydroxide are more preferred, sodium hydroxide and potassium hydroxide are further preferred, and potassium hydroxide is particularly preferred.

[0510] The amount of the base used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0.1 to 100 mol, preferably 1 to 70 mol, more preferably 2 to 40 mol per 1 mol of the compound represented by formula (I').

[0511] The amount of water used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and further preferably 1 to 50 parts by mass, based on 1 part by mass of the compound represented by formula (I').

[0512] The reaction temperature in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0 to 100°C, preferably 5 to 100°C, more preferably 20 to 100°C, further preferably 40 to 100°C, particularly preferably 60 to 100°C.

[0513] The reaction time in the hydrolysis reaction of the compound represented by the formula (I') in the presence of a base is usually 0.5 to 120 hours, preferably 1 to 72 hours, and more preferably 1 to 24 hours.

[0514] The method for extracting the compound represented by formula (IM1) from the reaction mixture of the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is not particularly limited, and the extraction can be performed by various known methods. For example, after the reaction is completed, the compound (IM1) can be extracted by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture for neutralization and filtering. In addition, the compound (IM1) can be extracted by washing the obtained residue with an alkaline aqueous solution such as sodium hydroxide aqueous solution, and / or an acidic aqueous solution such as hydrochloric acid, using an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or a mixed solvent thereof with an alkaline aqueous solution such as sodium hydroxide aqueous solution, and / or with an acidic aqueous solution such as hydrochloric acid. It can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and / or recrystallization, or after the reaction is completed, the reaction mixture can be purified by column chromatography and / or recrystallization. After the reaction is completed, the compound (IM1) can be extracted by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture for neutralization and then filtering. The compound (IM1) can be further purified by column chromatography and / or recrystallization.

[0515] The compound represented by formula (IM2) can be produced by reacting the compound represented by formula (pt1) with the compound represented by formula (pt3) to form a compound represented by formula (IM2) (hereinafter, sometimes referred to as compound (IM2)).

[0516]

[0517] In formula (pt1), formula (pt3), and formula (IM2), R 1 ~R 5 , Q 2 Means the same as above.

[0518] The amount of the compound represented by formula (pt3) used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is generally 0.1 to 10 mol, preferably 0.1 to 5 mol, more preferably 0.5 to 2 mol, and further preferably 0.8 to 1.5 mol, relative to 1 mol of the compound represented by formula (pt1).

[0519] The reaction temperature of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, further preferably 100 to 230°C, particularly preferably 120 to 200°C.

[0520] The reaction time of the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 0.5 to 500 hours.

[0521] The reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

[0522] Examples of the solvent in the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt3) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; Aliphatic hydrocarbon solvents such as alkane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.

[0523] Preferred examples include phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0524] More preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, and N-methylpyrrolidone are mentioned.

[0525] More preferably, phenol and methyl benzoate are mentioned.

[0526] Particularly preferably, phenol is used.

[0527] The amount of the solvent used in the reaction of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and further preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (pt1).

[0528] The method for extracting compound (IM2) from the reaction mixture of the compound represented by formula (pt1) and the compound represented by formula (pt3) is not particularly limited, and the extraction can be carried out by various known methods. For example, after the reaction is completed, a solvent such as methanol in which compound (IM2) in the reaction mixture is not easily soluble but compounds other than compound (IM2) are easily soluble is added to the reaction mixture, and after sufficient mixing, the compound (IM2) is extracted by filtering. In addition, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, water or a mixed solvent thereof can be used, and the obtained residue can be washed with an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and / or an acidic aqueous solution such as hydrochloric acid, thereby extracting compound (IM2). It can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture may be distilled off and the obtained residue may be purified by column chromatography and / or recrystallization, etc., or after the reaction is completed, the reaction mixture may be purified by column chromatography and / or recrystallization, etc. After the reaction is completed, the reaction mixture may be added to a solvent such as methanol in which the compound (IM2) in the reaction mixture is not easily soluble but compounds other than the compound (IM2) are easily soluble, mixed well, and then filtered to extract the compound (IM2). It may be further purified by column chromatography and / or recrystallization, etc.

[0529] In the compound represented by formula (I), Q 2 The compound represented by formula (IQQ20-1) which is a group represented by formula (QQ20) can be produced by reacting a compound represented by formula (IM1), a compound represented by formula (pt-L), a compound represented by formula (IM3), and a compound represented by formula (IM4).

[0530]

[0531] In formula (pt-L), formula (IM1), formula (IM3), formula (IM4) and formula (IQQ20-1), L, Q 1 , Q 3 , Q 4 , R 1 ~R 5 , R Q95 ~R Q104 , p and q have the same meanings as above. 3 , Q 4 , R Q95 ~R Q104 When there are plural numbers of , M and MM respectively, they may be the same as or different from each other.

[0532] Specific examples of the compound that can become L (for example, a compound represented by the formula (pt-L)) include the following compounds.

[0533]

[0534] L corresponds to the structure other than -C(=O)-O-C(=O)- from the above compounds.

[0535] The compound represented by formula (IM3) can be produced in the same manner as the compound represented by formula (IM1) described above.

[0536] The compound represented by formula (IM4) can be produced in the same manner as the compound represented by formula (IM2) described above.

[0537] The amount of the compound represented by formula (pt-L) used is usually 0.001 to 10 mol, preferably 0.005 to 5 mol, more preferably 0.01 to 2 mol, further preferably 0.1 to 1.5 mol, based on 1 mol of the compound represented by formula (IM1).

[0538] When p is not 0, the amount of the compound represented by the formula (IM3) used is usually 0.01 to 100 mol, preferably 0.05 to 20 mol, more preferably 0.1 to 10 mol, based on 1 mol of the compound represented by the formula (IM1).

[0539] When q is not 0, the amount of the compound represented by the formula (IM4) used is usually 0.01 to 100 mol, preferably 0.05 to 20 mol, more preferably 0.1 to 10 mol, based on 1 mol of the compound represented by the formula (IM1).

[0540] The amount of the compound represented by formula (IM3) and the amount of the compound represented by formula (IM4) used is preferably p moles of the compound represented by formula (IM3) and q moles of the compound represented by formula (IM4) relative to 1 mole of the compound represented by formula (IM1).

[0541] The reaction temperature is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, further preferably 100 to 230°C, particularly preferably 150 to 200°C.

[0542] The reaction time is usually 0.5 to 500 hours.

[0543] The reaction of the compound represented by formula (IM1), the compound represented by formula (pt-L), the compound represented by formula (IM3), and the compound represented by formula (IM4) is usually carried out in the presence of a solvent.

[0544] Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylolbenzene, and the like. Aromatic hydrocarbon solvents such as trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.; etc.

[0545] Preferred examples include diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0546] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

[0547] More preferably, methyl benzoate is used.

[0548] The amount of the solvent used is usually 1 to 1000 parts by mass based on the total parts by mass of the compound represented by formula (IM1), the compound represented by formula (IM3), and the compound represented by formula (IM4).

[0549] In the reaction of the compound represented by formula (IM1), the compound represented by formula (pt-L), the compound represented by formula (IM3), and the compound represented by formula (IM4), at least one selected from acids and metal salts is preferably present.

[0550] Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid, and tartaric acid; etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, more preferably carboxylic acid, and further preferably benzoic acid.

[0551] The amount of the acid used is generally 1 to 90 times the total mole of the compound represented by formula (IM1), the compound represented by formula (IM3) and the compound represented by formula (IM4), preferably 1 to 70 times the total mole, more preferably 1 to 50 times the total mole, and still more preferably 1 to 30 times the total mole.

[0552] Examples of the metal salt include zinc chloride and aluminum chloride.

[0553] The amount of the metal salt used is generally 0.01 to 30 times the total mole of the compound represented by formula (IM1), the compound represented by formula (IM3) and the compound represented by formula (IM4), preferably 0.01 to 20 times the total mole, more preferably 0.01 to 10 times the total mole, and further preferably 0.01 to 3 times the total mole.

[0554] The method for extracting the compound represented by formula (IQQ20-1) from the reaction mixture is not particularly limited, and the compound can be extracted by various known methods. For example, after the reaction is completed, the compound (IQQ20-1) in the reaction mixture is sometimes difficult to dissolve, but compounds other than the compound (IQQ20-1) are easily soluble. The solvent such as methanol can be mixed with the reaction mixture and filtered to extract the compound (IQQ20-1). In addition, the compound (IQQ20-1) can be extracted by washing the obtained residue with an alkaline aqueous solution such as sodium hydroxide aqueous solution, and / or an acidic aqueous solution such as hydrochloric acid, and then washing with water, methanol, a low-boiling alcohol, or a mixed solvent thereof. It can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture may be distilled off and the obtained residue may be purified by column chromatography and / or recrystallization, or the reaction mixture may be purified by column chromatography and / or recrystallization, etc. After the reaction is completed, the compound (IQQ20-1) in the reaction mixture may not be easily soluble, but compounds other than the compound (IQQ20-1) may be easily soluble, and the reaction mixture may be fully mixed with the solvent such as methanol and then filtered to extract the compound (IQQ20-1). The compound (IQQ20-1) may be further purified by column chromatography and / or recrystallization, etc.

[0555] In the compound represented by formula (I), Q 1 The compound represented by formula (IQQ20-2) which is a group represented by formula (QQ20) can be produced by reacting a compound represented by formula (IM2), a compound represented by formula (pt-L), a compound represented by formula (IM3), and a compound represented by formula (IM4).

[0556]

[0557] In formula (pt-L), formula (IM2), formula (IM3), formula (IM4), and formula (IQQ20-2), L, Q 2 , Q 3 , Q 4 , R 1 ~R 5 , R Q95 ~R Q104 , p and q have the same meanings as above. 3 , Q 4 , R Q95 ~R Q104 When there are plural numbers of , M and MM respectively, they may be the same as or different from each other.

[0558] The amount of the compound represented by formula (pt-L) used is usually 0.001 to 10 mol, preferably 0.005 to 5 mol, more preferably 0.01 to 2 mol, further preferably 0.1 to 1.5 mol, based on 1 mol of the compound represented by formula (IM2).

[0559] When p is not 0, the amount of the compound represented by formula (IM3) used is usually 0.01 to 100 mol, preferably 0.05 to 20 mol, more preferably 0.1 to 10 mol, based on 1 mol of the compound represented by formula (IM2).

[0560] When q is not 0, the amount of the compound represented by formula (IM4) used is usually 0.01 to 100 mol, preferably 0.05 to 20 mol, more preferably 0.1 to 10 mol, based on 1 mol of the compound represented by formula (IM2).

[0561] The amount of the compound represented by formula (IM3) and the amount of the compound represented by formula (IM4) used is preferably p moles of the compound represented by formula (IM3) and q moles of the compound represented by formula (IM4) relative to 1 mole of the compound represented by formula (IM2).

[0562] The reaction temperature is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, further preferably 100 to 230°C, particularly preferably 150 to 200°C.

[0563] The reaction time is usually 0.5 to 500 hours.

[0564] The reaction of the compound represented by formula (IM2), the compound represented by formula (pt-L), the compound represented by formula (IM3), and the compound represented by formula (IM4) is usually carried out in the presence of a solvent.

[0565] Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylolbenzene, and the like. Aromatic hydrocarbon solvents such as trichloromethane (for example, 1,3,5-trimethylbenzene), decalin, tetralin, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.; etc.

[0566] Preferred examples include diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0567] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, and N-methylpyrrolidone are mentioned.

[0568] More preferably, methyl benzoate is used.

[0569] The amount of the solvent used is usually 1 to 1000 parts by mass based on the total parts by mass of the compound represented by formula (IM2), the compound represented by formula (IM3), and the compound represented by formula (IM4).

[0570] In the reaction of the compound represented by formula (IM2), the compound represented by formula (pt-L), the compound represented by formula (IM3), and the compound represented by formula (IM4), at least one selected from acids and metal salts is preferably present.

[0571] Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid, and tartaric acid; etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, more preferably carboxylic acid, and further preferably benzoic acid.

[0572] The amount of the acid used is generally 1 to 90 times the total mole of the compound represented by formula (IM2), the compound represented by formula (IM3) and the compound represented by formula (IM4), preferably 1 to 70 times the total mole, more preferably 1 to 50 times the total mole, and still more preferably 1 to 30 times the total mole.

[0573] Examples of the metal salt include zinc chloride and aluminum chloride.

[0574] The amount of the metal salt used is generally 0.01 to 30 times the total mole of the compound represented by formula (IM2), the compound represented by formula (IM3) and the compound represented by formula (IM4), preferably 0.01 to 20 times the total mole, more preferably 0.01 to 10 times the total mole, and further preferably 0.01 to 3 times the total mole.

[0575] The method for extracting the compound represented by formula (IQQ20-2) from the reaction mixture is not particularly limited, and the compound can be extracted by various known methods. For example, after the reaction is completed, the compound (IQQ20-2) in the reaction mixture is sometimes difficult to dissolve, but compounds other than the compound (IQQ20-2) are easily soluble. The solvent such as methanol can be mixed with the reaction mixture and filtered to extract the compound (IQQ20-2). In addition, the compound (IQQ20-2) can be extracted by washing the residue with an alkaline aqueous solution such as sodium hydroxide aqueous solution and / or an acidic aqueous solution such as hydrochloric acid, and then washing with water, methanol, a low-boiling alcohol, or a mixed solvent thereof using an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water, or a mixed solvent thereof. The compound (IQQ20-2) can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture may be distilled off and the obtained residue may be purified by column chromatography and / or recrystallization, or the reaction mixture may be purified by column chromatography and / or recrystallization, etc. After the reaction is completed, the compound (IQQ20-2) in the reaction mixture may not be easily soluble, but compounds other than the compound (IQQ20-2) may be easily soluble, and the reaction mixture may be fully mixed with the solvent such as methanol and then filtered to extract the compound (IQQ20-2). The compound (IQQ20-2) may be further purified by column chromatography and / or recrystallization, etc.

[0576] In the compound represented by formula (I), Q 1 and Q 2 The compound represented by formula (IQQ20-3) which is a group represented by formula (QQ20) can be produced by reacting a compound represented by formula (pt1), a compound represented by formula (pt-L), a compound represented by formula (IM3), and a compound represented by formula (IM4).

[0577]

[0578]

[0579] In formula (pt-L), formula (pt1), formula (IM3), and formula (IM4), L, Q 3 , Q 4 , R 1 ~R 5 , R Q95 ~R Q104 , p and q have the same meanings as above.

[0580] [In formula (IQQ20-3), L, Q 3 , Q 4, R 1 ~R 5 , R Q95 ~R Q104 , p and q have the same meanings as above. p' is an integer greater than 0, q' is an integer greater than 0, and the sum of p' and q' is an integer greater than 1. L, Q 3 , Q 4 , R Q95 ~R Q104 When , M and MM exist in plural numbers, they may be the same as or different from each other. ]

[0581] p' in the formula (IQQ20-3) is an integer greater than 0, preferably an integer from 0 to 11, more preferably an integer from 0 to 5, further preferably an integer from 0 to 3, particularly preferably an integer from 0 to 2, and further preferably an integer from 0 to 1. q' in the formula (IQQ20-3) is an integer greater than 0, preferably an integer from 0 to 11, more preferably an integer from 0 to 5, further preferably an integer from 0 to 3, particularly preferably an integer from 0 to 2, and further preferably an integer from 0 to 1. The sum of p' and q' in the formula (IQQ20-3) is preferably an integer from 1 to 11, more preferably an integer from 1 to 5, further preferably an integer from 1 to 3, particularly preferably an integer from 1 to 2, and further preferably an integer of 1.

[0582] The amount of the compound represented by formula (pt-L) used is usually 0.001 to 20 mol, preferably 0.005 to 10 mol, more preferably 0.01 to 4 mol, further preferably 0.1 to 3 mol, based on 1 mol of the compound represented by formula (pt1).

[0583] When p or p' is not 0, the amount of the compound represented by formula (IM3) used is usually 0.01 to 200 mol, preferably 0.05 to 40 mol, more preferably 0.1 to 20 mol, based on 1 mol of the compound represented by formula (pt1).

[0584] When q or q' is not 0, the amount of the compound represented by formula (IM4) used is usually 0.01 to 200 mol, preferably 0.05 to 40 mol, more preferably 0.1 to 20 mol, based on 1 mol of the compound represented by formula (pt1).

[0585] The amount of the compound represented by formula (IM3) and the amount of the compound represented by formula (IM4) used is preferably (p+p') moles of the compound represented by formula (IM3) and (q+q') moles of the compound represented by formula (IM4) relative to 1 mole of the compound represented by formula (pt1).

[0586] The reaction temperature is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, further preferably 100 to 230°C, particularly preferably 150 to 200°C.

[0587] The reaction time is usually 0.5 to 500 hours.

[0588] The reaction of the compound represented by formula (pt1), the compound represented by formula (pt-L), the compound represented by formula (IM3), and the compound represented by formula (IM4) is usually carried out in the presence of a solvent.

[0589] Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylolbenzene, and the like. Aromatic hydrocarbon solvents such as trichloromethane (for example, 1,3,5-trimethylbenzene), decalin, tetralin, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.; etc.

[0590] Preferred examples include diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0591] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, and N-methylpyrrolidone are mentioned.

[0592] More preferably, methyl benzoate is used.

[0593] The amount of the solvent used is usually 1 to 1000 parts by mass based on the total parts by mass of the compound represented by formula (pt1), the compound represented by formula (IM3), and the compound represented by formula (IM4).

[0594] In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt-L), the compound represented by formula (IM3), and the compound represented by formula (IM4), at least one selected from acids and metal salts is preferably coexistent.

[0595] Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid, and tartaric acid; etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, more preferably carboxylic acid, and further preferably benzoic acid.

[0596] The amount of the acid used is generally 1 to 90 times the total mole of the compound represented by formula (pt1), the compound represented by formula (IM3) and the compound represented by formula (IM4), preferably 1 to 70 times the total mole, more preferably 1 to 50 times the total mole, and further preferably 1 to 30 times the total mole.

[0597] Examples of the metal salt include zinc chloride and aluminum chloride.

[0598] The amount of the metal salt used is generally 0.01 to 30 times the total mole of the compound represented by formula (pt1), the compound represented by formula (IM3) and the compound represented by formula (IM4), preferably 0.01 to 20 times the total mole, more preferably 0.01 to 10 times the total mole, and further preferably 0.01 to 3 times the total mole.

[0599] The method for extracting the compound represented by formula (IQQ20-3) from the reaction mixture is not particularly limited, and the compound can be extracted by various known methods. For example, after the reaction is completed, the compound (IQQ20-3) in the reaction mixture is sometimes difficult to dissolve, but compounds other than the compound (IQQ20-3) are easily soluble. The reaction mixture is mixed with a solvent such as methanol, and then filtered to extract the compound (IQQ20-3). In addition, the compound (IQQ20-3) can be extracted by washing the obtained residue with an alkaline aqueous solution such as sodium hydroxide aqueous solution, and / or an acidic aqueous solution such as hydrochloric acid, and then washing with water, a low-boiling alcohol such as methanol, or a mixed solvent thereof. It can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture may be distilled off and the obtained residue may be purified by column chromatography and / or recrystallization, or the reaction mixture may be purified by column chromatography and / or recrystallization, etc. After the reaction is completed, the compound (IQQ20-3) in the reaction mixture may not be easily soluble, but compounds other than the compound (IQQ20-3) may be easily soluble, and the reaction mixture may be fully mixed with the solvent such as methanol and then filtered to extract the compound (IQQ20-3). The compound (IQQ20-3) may be further purified by column chromatography and / or recrystallization, etc.

[0600] By selecting R 1 ~R 5 and R Q1 ~R Q104 At least one of the oligomers or polymers is bonded to each other; through a plurality of compounds (I) respectively selected from R 1 ~R 5 and R Q1 ~R Q104 At least one of the substitutions is a bonding site and the bonding sites are bonded to each other by a single bond to form an oligomer or polymer; and a plurality of compounds (I) are selected from R 1 ~R 5 and R Q1 ~R Q104 At least one of each of the groups is substituted as a bonding site or is not substituted as a bonding site, and the bonding site and the group not substituted as the bonding site are bonded to each other to form an oligomer or polymer, which can be produced by the same reaction as above.

[0601] For example, formula (I 11 ) (hereinafter, sometimes referred to as compound (I 11)) can be produced by reacting a compound represented by formula (pt11) with a compound represented by formula (pt2) and a compound represented by formula (pt3).

[0602] It should be noted that the compound (I) of the present invention also contains the formula (I 11 ) represented by a compound.

[0603]

[0604] Formula (pt11) and Formula (I 11 ), R 1 ~R 5 , Q 1 and Q 2 The formula (pt11) and the formula (I 11 ), []-TU-[] means that the inside [] is selected from R 1 ~R 5 At least one of them is bonded to each other; the ones in [] are selected from R 1 ~R 5 At least one of them is substituted as a bonding site, and the bonding sites are bonded to each other by a single bond; or the group [] is selected from R 1 ~R 5 At least one of each of the groups is substituted as a bonding site or is not substituted as a bonding site, and the bonding site and the group not substituted as the bonding site are bonded to each other.

[0605] The amount of the compound represented by formula (pt2) used in the reaction of the compound represented by formula (pt11) with the compound represented by formula (pt2) and the compound represented by formula (pt3) is generally 0.1 to 60 mol, preferably 1 to 40 mol, more preferably 1 to 32 mol, and further preferably 2 to 20 mol, relative to 1 mol of the compound represented by formula (pt11).

[0606] The amount of the compound represented by formula (pt3) used in the reaction of the compound represented by formula (pt11) with the compound represented by formula (pt2) and the compound represented by formula (pt3) is generally 0.1 to 60 mol, preferably 1 to 40 mol, more preferably 1 to 32 mol, and further preferably 2 to 20 mol, relative to 1 mol of the compound represented by formula (pt11).

[0607] The reaction temperature is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, further preferably 100 to 230°C, particularly preferably 150 to 200°C.

[0608] The reaction time is usually 0.5 to 500 hours.

[0609] The reaction of the compound represented by formula (pt11), the compound represented by formula (pt2), and the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

[0610] Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitro hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide.

[0611] Preferred examples include diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0612] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, and N-methylpyrrolidone are mentioned.

[0613] More preferably, methyl benzoate is used.

[0614] The amount of the solvent used is usually 1 to 2000 parts by mass based on 1 part by mass of the compound represented by formula (pt11) in the reaction of the compound represented by formula (pt2) and the compound represented by formula (pt3).

[0615] In the reaction of the compound represented by formula (pt11), the compound represented by formula (pt2), and the compound represented by formula (pt3), it is preferred that at least one selected from the group consisting of an acid and a metal salt coexists.

[0616] Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid, and tartaric acid; etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, more preferably carboxylic acid, and further preferably benzoic acid.

[0617] The amount of the acid used in the reaction of the compound represented by formula (pt11) with the compound represented by formula (pt2) and the compound represented by formula (pt3) is generally 1 to 180 mol, preferably 1 to 140 mol, more preferably 1 to 100 mol, and further preferably 1 to 60 mol, relative to 1 mol of the compound represented by formula (pt11).

[0618] Examples of the metal salt include zinc chloride and aluminum chloride.

[0619] The amount of the metal salt used in the reaction of the compound represented by formula (pt11) with the compound represented by formula (pt2) and the compound represented by formula (pt3) is generally 0.01 to 60 mol, preferably 0.01 to 40 mol, more preferably 0.01 to 20 mol, and further preferably 0.01 to 6 mol, relative to 1 mol of the compound represented by formula (pt11).

[0620] Extract the formula (I 11 ) is not particularly limited, and can be extracted by various known methods. For example, after the reaction is completed, the compound represented by formula (I 11 ) is sometimes difficult to dissolve and the compound represented by formula (I 11 ) is easily dissolved in a solvent such as methanol, and the reaction mixture is fully mixed and filtered to extract the compound represented by formula (I 11 ). Alternatively, the residue obtained may be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or a mixed solvent thereof, and then washed with an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and / or an acidic aqueous solution such as hydrochloric acid, and then washed with a low-boiling alcohol such as methanol or a mixed solvent thereof to extract the compound represented by formula (I 11) can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off and the obtained residue can be purified by column chromatography and / or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and / or recrystallization. 11 ) is sometimes difficult to dissolve and the compound represented by formula (I 11 ) is easily dissolved in a solvent such as methanol, and the reaction mixture is fully mixed and filtered to extract the compound represented by formula (I 11 ) can be further purified by column chromatography and / or recrystallization.

[0621] A sulfo group or -SO3M can be introduced into compound (I) by reacting compound (I) with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid. Compounds into which a sulfo group or -SO3M is introduced are included in the compounds of the present invention.

[0622] The amount of SO 3 in fuming sulfuric acid used is usually 1 to 200 mol, preferably 2 to 150 mol, more preferably 3 to 100 mol, further preferably 5 to 80 mol, based on 1 mol of compound (I).

[0623] The content of SO 3 in fuming sulfuric acid is usually 1 to 90 parts by mass, preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and further preferably 15 to 50 parts by mass, based on 100 parts by mass of fuming sulfuric acid.

[0624] The amount of chlorosulfonic acid used is usually 1 to 500 mol, preferably 1 to 300 mol, more preferably 1 to 200 mol, further preferably 1 to 150 mol, based on 1 mol of compound (I).

[0625] When chlorosulfonic acid is used to introduce a sulfonic group or -SO3M into compound (I), it can be carried out in the presence of a solvent. Examples of the solvent include halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene.

[0626] The amount of the solvent used is usually 1 to 1000 parts by mass based on 1 part by mass of Compound (I).

[0627] The reaction temperature of sulfonation is usually -20 to 200° C., preferably -10 to 150° C., and more preferably 0 to 100° C. The reaction time is usually 0.5 to 300 hours.

[0628] The method for extracting the compound into which a sulfonic group or -SO3M is introduced into compound (I) from the reaction mixture is not particularly limited, and various known methods can be used for extraction. For example, after the reaction is completed, the reaction mixture can be added dropwise to ice, and the obtained mixture can be filtered to extract the compound into which a sulfonic group or -SO3M is introduced into compound (I). It can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the reaction mixture can be added dropwise to ice, and the obtained mixture can be mixed with a hydrophilic organic solvent such as an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, and a mixed solvent thereof, in which the compound into which a sulfonic group or -SO3M is introduced is sometimes difficult to dissolve, and compounds other than the compound into which a sulfonic group or -SO3M is introduced into compound (I) are easily soluble, and filtration can be performed to extract the compound into which a sulfonic group or -SO3M is introduced into compound (I). It can be further purified by column chromatography and / or recrystallization. Alternatively, after the reaction is completed, the reaction mixture can be added dropwise to ice, the obtained mixture can be neutralized with an aqueous solution such as ammonia, a water-soluble amine or a mixture thereof, the mixture can be mixed with a hydrophilic organic solvent such as an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile or a mixed solvent thereof, filtered, and the solvent of the obtained filtrate can be distilled off, thereby extracting the compound (I) into which the sulfonic group or -SO3M is introduced. It can be further purified by column chromatography and / or recrystallization.

[0629] The compound (I) having -SO3(MM) and / or -CO2(MM) can be produced by reacting the compound (I) having -SO3H and / or -CO2H with a salt having MM.

[0630] The amount of the salt having MM to be used is usually 0.01 to 100 mol, preferably 0.02 to 50 mol, more preferably 0.1 to 30 mol, based on 1 mol of the compound (I) having -SO3H and / or -CO2H.

[0631] The reaction temperature is usually 0 to 100°C, preferably 0 to 80°C, more preferably 0 to 60°C, further preferably 0 to 40°C.

[0632] The reaction time is usually 0.5 to 500 hours.

[0633] The reaction of the compound (I) having -SO3H and / or -CO2H and the salt having MM is usually carried out in the presence of a solvent. Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylbenzene Aromatic hydrocarbon solvents such as trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, tetralin, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.; etc.

[0634] Preferred are water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and mixed solvents thereof, and water is more preferred.

[0635] The amount of the solvent used is usually 1 to 1000 parts by mass, preferably 10 to 500 parts by mass, and more preferably 20 to 300 parts by mass, relative to 1 part by mass of the compound (I) having -SO3H and / or -CO2H.

[0636] The reaction of the compound (I) having -SO3H and / or -CO2H and the salt having MM can be carried out in the presence of a base.

[0637] Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,5-diazabicyclo[4.3.0]non-5-ene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium; and inorganic bases such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide. Inorganic bases are preferred, lithium hydroxide, sodium hydroxide and potassium hydroxide are more preferred, sodium hydroxide and potassium hydroxide are further preferred, and sodium hydroxide is particularly preferred.

[0638] The amount of the base used is usually 1 to 100 mol, preferably 1 to 50 mol, more preferably 1 to 20 mol, and further preferably 1 to 10 mol, based on 1 mol of the compound (I) having -SO3H and / or -CO2H.

[0639] The method for extracting the compound (I) having -SO3(MM) and / or -CO2(MM) from the reaction mixture is not particularly limited, and the extraction can be performed by various known methods. For example, the compound (I) having -SO3(MM) and / or -CO2(MM) can be extracted by filtering the reaction mixture after the reaction is completed. In addition, the residue can be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or a mixed solvent thereof, and then washed with water, a low-boiling alcohol such as methanol or a mixed solvent thereof for purification.

[0640] [Coloring composition]

[0641] The coloring composition of the present invention comprises compound (I) and resin (B). According to the coloring composition of the present invention, a darker color filter can be formed compared to a coloring composition containing CI Pigment Yellow 138. The color filter formed by the coloring composition of the present invention can be preferably used in display devices such as liquid crystal display devices. The coloring composition of the present invention is preferably a yellow composition, an orange composition, a red composition and a green composition.

[0642] The content of the solid content in the coloring composition is less than 100 mass % relative to the total amount of the coloring composition, preferably 0.01 mass % or more and less than 100 mass %, more preferably 0.1 mass % to 99.9 mass %, further preferably 0.1 mass % to 99 mass %, particularly preferably 1 mass % to 90 mass %, further preferably 1 mass % to 80 mass %, particularly preferably 1 mass % to 70 mass %, extremely preferably 1 mass % to 60 mass %, and most preferably 1 mass % to 50 mass %.

[0643] In this specification, the "total amount of solid content" refers to the total amount of components other than the solvent (E) in the coloring composition of the present invention. The total amount of solid content and the content of each component relative to the total amount of solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0644] The content of compound (I) in the coloring composition is less than 100% by mass in the total amount of the solid content, preferably 0.0001% by mass to 99.9999% by mass, more preferably 0.0001% by mass to 99% by mass, further preferably 0.0001% by mass to 90% by mass, particularly preferably 0.0001% by mass to 80% by mass, further preferably 0.0001% by mass to 70% by mass, particularly preferably 0.0001% by mass to 60% by mass, extremely preferably 0.0001% by mass to 55% by mass, and most preferably 0.1% by mass to 55% by mass.

[0645] [Solvent (E)]

[0646] The solvent (E) is not particularly limited, and a solvent commonly used in this field can be used. Examples of the solvent (E) include ester solvents (solvents containing -CO-O- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -CO-O- in the molecule), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -CO-O- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO- and -CO-O- in the molecule), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0647] 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.

[0648] 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-dihydrofu ... Alkane, 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, etc.

[0649] 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, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0650] 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.

[0651] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0652] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0653] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0654] These solvents may be used in combination of two or more.

[0655] Among the above-mentioned solvents, organic solvents having a boiling point of 120° C. to 180° C. at 1 atm are preferred from the viewpoint of coating properties and drying properties. Preferred examples of the solvent include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide. More preferred examples include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

[0656] The content of the solvent (E) is less than 100% by mass, preferably 99.99% by mass or less, more preferably 0.1% by mass to 99.9% by mass, further preferably 1% by mass to 99.9% by mass, particularly preferably 10% by mass to 99% by mass, further preferably 20% by mass to 99% by mass, particularly preferably 30% by mass to 99% by mass, extremely preferably 40% by mass to 99% by mass, and most preferably 50% by mass to 99% by mass, relative to the total amount of the colored composition.

[0657] [Resin (B)]

[0658] The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least one monomer selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "monomer (a)").

[0659] The resin (B) is preferably a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b)") and other structural units.

[0660] Examples of other structural units include structural units derived from a monomer copolymerizable with the monomer (a) (which is different from the monomer (a) and the monomer (b); hereinafter sometimes referred to as "monomer (c)"), and structural units having an ethylenically unsaturated bond.

[0661] In the present specification, "(meth)acrylic acid" means at least one selected from acrylic acid and methacrylic acid. "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0662] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acids; 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, and 1,4- Unsaturated dicarboxylic acids such as cyclohexenedicarboxylic acid; 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, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds containing a carboxyl group; 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; unsaturated mono[(meth)acryloxyalkyl] esters of polycarboxylic acids having a valence of 2 or more such as mono[2-(meth)acryloxyethyl] succinate and mono[2-(meth)acryloxyethyl] phthalate; unsaturated acrylic esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid; etc.

[0663] Among them, acrylic acid, methacrylic acid, o-, m-, and p-vinylbenzoic acid, maleic anhydride, and the like are preferred from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an alkaline aqueous solution.

[0664] Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0665] As monomer (b), for example, there can be mentioned a monomer having an oxetane group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), a monomer having an oxetane group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), and a monomer having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)").

[0666] Examples of the monomer (b1) include a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1-1)") and a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1-2)").

[0667] As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred. Examples of the monomer (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) ether, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tri(glycidyloxymethyl)styrene, 2,3,5-tri(glycidyloxymethyl)styrene, 2,3,6-tri(glycidyloxymethyl)styrene, 3,4,5-tri(glycidyloxymethyl)styrene and 2,4,6-tri(glycidyloxymethyl)styrene, etc.

[0668] Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel Co., Ltd.), compounds represented by formula (BI) and compounds represented by formula (BII).

[0669]

[0670] [In formula (BI) and formula (BII), R a and R b Each of X independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group. a and X b Independently represent single bonds, *-R c -, * - R c -O-, *-R c -S- or *-Rc -NH-. c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bonding site with O. ]

[0671] 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.

[0672] 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.

[0673] As R a and R b , 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.

[0674] 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.

[0675] As X a and X b , preferably, a single bond, a methylene group, an ethylene group, *-CH2-O- and *-CH2CH2-O- are mentioned, and more preferably, a single bond and *-CH2CH2-O- (* represents a bonding site with O) are mentioned.

[0676] Examples of the compound represented by formula (BI) include compounds represented by any one of formula (BI-1) to formula (BI-15). Among them, compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), and formula (BI-11) to formula (BI-15) are preferred, and compounds represented by formula (BI-1), formula (BI-7), formula (BI-9), and formula (BI-15) are more preferred.

[0677]

[0678]

[0679] Examples of the compound represented by formula (BII) include compounds represented by any one of formula (BII-1) to formula (BII-15), among which preferred examples include compounds represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15), and more preferred examples include compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

[0680]

[0681]

[0682] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more thereof. The compound represented by formula (BI) and the compound represented by formula (BII) may also be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, their content ratio [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and further preferably 20:80 to 80:20 on a molar basis.

[0683] As monomer (b2), a monomer having an oxetane group and a (meth)acryloyloxy group is more preferred. As monomer (b2), for example, 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, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. can be mentioned.

[0684] As the monomer (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0685] As the monomer (b), the monomer (b1) is preferred because the reliability of the obtained color filter, such as heat resistance and chemical resistance, can be improved. Furthermore, the monomer (b1-2) is more preferred because the storage stability of the colored composition is excellent.

[0686] Examples of the monomer (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 ]Decan-8-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]Decan-9-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]Decen-8-yl ester, (meth)acrylic acid tricyclic [5.2.1.0 2,6] (Meth)acrylates such as decen-9-yl (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; (meth)acrylates containing a hydroxyl group such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; 2,2,3,3,4-dimethoxy-2-(meth)acrylate. , 4,5,5-octafluoropentyl ester and other halogen-containing (meth)acrylates; diethyl maleate, diethyl fumarate and diethyl itaconate and other dicarboxylic acid diesters; 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 5,6-dimethoxybicyclo[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-dimethoxybicyclo[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] bicyclic unsaturated compounds such as hept-2-ene; 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 Biological substances; aromatic compounds containing vinyl groups such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; nitriles containing vinyl groups such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; amides containing vinyl groups such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; etc. .

[0687] Among them, styrene, vinyltoluene, tricyclo[5.2.1.0 2,6 ]Decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, phenyl (meth)acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate, 9-vinylcarbazole, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate and 2-ethylhexyl (meth)acrylate, etc.

[0688] 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, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl ester / benzyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / 9-vinyl carbazole / (meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / phenyl (meth)acrylate / o-vinylbenzoic acid copolymer, (meth)acrylate 3,4-epoxytricyclo[5.2.1.0 2,6] decyl ester / phenyl (meth)acrylate / m-vinyl benzoic acid copolymer, (meth)acrylate 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / phenyl (meth)acrylate / p-vinyl benzoic acid copolymer, (meth)acrylate 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / phenyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth)acrylate 2,2,3,3,4,4,5,5-octafluoropentyl ester / (meth)acrylate copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylate copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, (meth) acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid / N-cyclohexyl maleimide / (meth) acrylic acid 2-hydroxyethyl ester copolymer, (meth) acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid / vinyl toluene copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid / 2-ethylhexyl (meth) acrylic acid ester copolymer, (meth) acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decyl ester / (meth)acrylate tricyclic [5.2.1.0 2,6 ]Decenyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and resins described in Japanese Patent Application Publication No. 9-106071, Japanese Patent Application Publication No. 2004-29518, and Japanese Patent Application Publication No. 2004-361455, etc.

[0689] Among them, as resin (B), a copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b) is preferred. Two or more resins (B) may be used in combination. In this case, resin (B) preferably contains at least one copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b), more preferably contains at least one copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b1), further preferably contains at least one copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b1-2), and particularly preferably contains a (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl ester / benzyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid / N-cyclohexyl maleimide / (meth) acrylic acid 2-hydroxyethyl ester copolymer, (meth) acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid / vinyl toluene copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ] One or more of decyl ester / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymers.

[0690] The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 to 100,000, more preferably 1,000 to 50,000, further preferably 1,000 to 30,000, particularly preferably 3,000 to 30,000, and particularly preferably 5,000 to 30,000.

[0691] The dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1-6, more preferably 1-5, and even more preferably 1-4.

[0692] The acid value (solid content conversion value) of the resin (B) is preferably 10 to 500 mg-KOH / g, more preferably 20 to 450 mg-KOH / g, further preferably 20 to 400 mg-KOH / g, further preferably 20 to 370 mg-KOH / g, further preferably 30 to 370 mg-KOH / g, further preferably 30 to 350 mg-KOH / g, particularly preferably 30 to 340 mg-KOH / g, and most preferably 30 to 335 mg-KOH / g. 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 obtained, for example, by titration using a potassium hydroxide aqueous solution.

[0693] In the coloring composition, the content of the resin (B) is less than 100% by mass, preferably 0.00001% by mass to 99.99999% by mass, more preferably 1% by mass to 99% by mass, further preferably 1% by mass to 97% by mass, particularly preferably 1% by mass to 95% by mass, further preferably 3% by mass to 95% by mass, particularly preferably 5% by mass to 95% by mass, and extremely preferably 10% by mass to 95% by mass, relative to the total amount of the solid content.

[0694] [Preparation of a solution containing compound (I)]

[0695] The coloring composition of the present invention can be prepared by preparing a solution containing compound (I) containing compound (I) and solvent (E) in advance, and then using the solution containing compound (I) to prepare the coloring composition. When compound (I) is not dissolved in solvent (E), the solution containing compound (I) can be prepared by dispersing and mixing compound (I) in solvent (E). The solution containing compound (I) may contain a part or all of the solvent (E) contained in the coloring composition.

[0696] The content of the solid component of the solution containing compound (I) is less than 100 mass % relative to the total amount of the solution containing compound (I), preferably 0.01 mass % to 99.99 mass %, more preferably 0.1 mass % to 99.9 mass %, further preferably 0.1 mass % to 99 mass %, particularly preferably 1 mass % to 90 mass %, further preferably 1 mass % to 80 mass %, particularly preferably 1 mass % to 70 mass %, extremely preferably 1 mass % to 60 mass %, and most preferably 1 mass % to 50 mass %.

[0697] The content of compound (I) in the solution containing compound (I) is less than 100 mass % in the total amount of solid components in the solution containing compound (I), preferably 0.0001 mass % to 99.9999 mass %, more preferably 0.0001 mass % to 99 mass %, further preferably 1 mass % to 99 mass %, particularly preferably 3 mass % to 99 mass %, and further preferably 5 mass % to 99 mass %.

[0698] Compound (I) may be subjected to rosin treatment, surface treatment using a derivative into which an acidic group or a basic group is introduced, grafting treatment on the surface of compound (I) using a polymer compound, micronization treatment by a sulfuric acid micronization method, a salt milling method, etc., washing treatment with an organic solvent, water, etc. for removing impurities, removal treatment of ionic impurities by an ion exchange method, etc., etc., as required.

[0699] In addition, compound (I) may also be subjected to the following treatment as required:

[0700] Crystal structure conversion, particle shaping and / or rough homogenization of particle size;

[0701] The compound (I) is mixed with water and / or an organic solvent, and stirred and / or stirred while heating to obtain a suspension, and then the suspension is filtered to obtain the compound (I) with a changed crystal structure;

[0702] a treatment to change the crystal structure of compound (I) by recrystallization;

[0703] The compound (I) is mixed with water, sulfuric acid or an organic solvent, and stirred and / or stirred while heating to obtain a solution or a suspension, and then the solution or the suspension is mixed with a poor solvent for the compound (I) to obtain a suspension, and then the suspension is filtered to obtain the compound (I) with a changed crystal structure;

[0704] A treatment of mixing compound (I) and a derivative with water and / or an organic solvent, stirring and / or stirring while heating to obtain a suspension, and then filtering the suspension to obtain a mixture containing compound (I) with a changed crystal structure and / or a treatment of mixing compound (I) with a derivative;

[0705] a treatment of obtaining a mixture containing compound (I) having a changed crystal structure by recrystallizing the mixture of compound (I) and a derivative and / or a treatment of mixing compound (I) and a derivative;

[0706] Compound (I) and a derivative are mixed with water, sulfuric acid or an organic solvent, and stirred and / or stirred while heating to obtain a solution or a suspension, and then the solution or the suspension is mixed with a poor solvent for compound (I) to obtain a suspension, and then the suspension is filtered to obtain a mixture containing compound (I) with a changed crystal structure and / or a treatment of mixing compound (I) with a derivative; etc.

[0707] When a plurality of compounds (I) or derivatives are used, these treatments may be carried out individually or in combination of a plurality of compounds (I) or derivatives.

[0708] The particle size of compound (I) is preferably substantially uniform.

[0709] Examples of the organic solvent used for the above-mentioned crystal structure conversion include nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene , trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin and other aromatic hydrocarbon solvents; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents; etc.

[0710] Examples of the poor solvent include nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; and the like.

[0711] Examples of the derivatives include compounds represented by formula (z) and compounds represented by formula (z1).

[0712]

[0713] When the solution containing compound (I) contains a derivative, the content of the derivative is 0.01 to 100 parts by mass, preferably 0.01 to 70 parts by mass, more preferably 0.1 to 50 parts by mass, further preferably 0.1 to 30 parts by mass, and particularly preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of compound (I).

[0714] Compound (I) can be dispersed in a solution containing a dispersant to obtain a uniform dispersion of Compound (I). When multiple types of Compound (I) are used, they may be dispersed individually or as a mixture.

[0715] As dispersant, surfactant etc. can be enumerated, and can be any surfactant in cationic, anionic, nonionic and amphoteric. Specifically, surfactants such as polyester, polyamine and acrylic acid can be enumerated. These dispersants can be used alone or in combination of 2 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 system), AJISPER (registered trademark) (Ajinomoto Fine Chemicals (Strain) system), DISPERBYK (registered trademark) (BYK-Chemie (Strain) system) and BYK (registered trademark) (BYK-Chemie (Strain) system) etc. can be enumerated.

[0716] When the solution containing compound (I) contains a dispersant, the amount of the dispersant (solid content) used is, for example, 0.01 to 10,000 parts by mass, preferably 0.01 to 5,000 parts by mass, more preferably 0.01 to 1,000 parts by mass, further preferably 0.1 to 500 parts by mass, particularly preferably 0.1 to 300 parts by mass, further preferably 1 to 300 parts by mass, and particularly preferably 5 to 260 parts by mass, relative to 100 parts by mass of compound (I). When the amount of the dispersant used is within the above range, there is a tendency to obtain a solution containing compound (I) in a more uniform dispersed state.

[0717] The coloring composition of the present invention contains a resin (B), and after a solution containing a compound (I) containing a compound (I) and a solvent (E) is prepared in advance, when the coloring composition of the present invention is prepared using the solution containing the compound (I), the solution containing the compound (I) may contain a part or all, preferably a part, of the resin (B) contained in the coloring composition in advance. By containing the resin (B) in advance, the dispersion stability of the solution containing the compound (I) can be further improved.

[0718] When the solution containing compound (I) contains resin (B), the content of resin (B) is, for example, 0.01 to 10,000 parts by mass, preferably 0.01 to 5,000 parts by mass, more preferably 0.01 to 1,000 parts by mass, further preferably 0.1 to 500 parts by mass, particularly preferably 0.1 to 300 parts by mass, based on 100 parts by mass of compound (I).

[0719] [Polymerizable compound (C)]

[0720] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferably a (meth)acrylate compound.

[0721] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, and the above-mentioned monomer (a), monomer (b), and monomer (c).

[0722] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0723] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. As such a polymerizable compound, for example, 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, tri(2-(meth)acryloyl)propene, The invention also includes 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, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0724] The weight average molecular weight of the polymerizable compound (C) is preferably 50 to 4,000, more preferably 50 to 3,500, further preferably 50 to 3,000, particularly preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0725] The content of the polymerizable compound (C) is less than 100% by mass, preferably 0.00001% by mass to 99.99999% by mass, more preferably 1% by mass to 99% by mass, further preferably 1% by mass to 97% by mass, particularly preferably 1% by mass to 95% by mass, further preferably 1% by mass to 90% by mass, particularly preferably 2% by mass to 80% by mass, and extremely preferably 3% by mass to 70% by mass, relative to the total amount of the solid content in the colored composition.

[0726] [Polymerization initiator (D)]

[0727] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc. under the action of light or heat and initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator (D) include oxime compounds such as O-acyl oxime compounds, alkyl phenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0728] Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-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-dioxolanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, etc. As the O-acyl oxime compound, commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) can be used. Among them, as the O-acyl oxime compound, at least one selected from N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine is preferred, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine is more preferred.

[0729] Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)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 be used as the alkylphenone compound.

[0730] Examples of the alkylphenone compound 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.

[0731] 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'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, )-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, see JP-B-48-38403, JP-A-62-174204, etc.), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (for example, see JP-A-7-10913, etc.).

[0732] 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-[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 and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0733] 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.

[0734] 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 described later (hereinafter, sometimes referred to as the polymerization initiator aid (D1)), especially amines.

[0735] The polymerization initiator (D) preferably contains at least one selected from alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, oxime compounds and biimidazole compounds, more preferably contains an oxime compound, and even more preferably contains an O-acyloxime compound.

[0736] The content of the polymerization initiator (D) is preferably 0.001% by mass to 60% by mass, more preferably 0.01% by mass to 50% by mass, based on the total amount of the resin (B) and the polymerizable compound (C).

[0737] [Polymerization initiator aid (D1)]

[0738] The coloring composition of the present invention may contain a polymerization initiator aid (D1). The polymerization initiator aid (D1) is a compound or sensitizer for promoting the polymerization of the polymerizable compound (C) initiated by the polymerization initiator (D). When the polymerization initiator aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0739] 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. Preferably, 4,4'-bis(diethylamino)benzophenone is used. In addition, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used as the amine compound.

[0740] 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.

[0741] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0742] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylsulfanylacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0743] When the polymerization initiator aid (D1) is used, the content thereof is preferably 0.00001% by mass to 60% by mass, more preferably 0.0001% by mass to 50% by mass, based on the total amount of the resin (B) and the polymerizable compound (C).

[0744] [Colorant (A1)]

[0745] The coloring composition of the present invention may contain a colorant other than compound (I) (hereinafter, sometimes referred to as colorant (A1)). The colorant (A1) may contain one or more colorants. The colorant (A1) preferably contains one or more selected from yellow colorants, orange colorants, red colorants, and green colorants, and more preferably contains one or more selected from yellow colorants and green colorants.

[0746] Coloring agent (A1) can be dye, also can be pigment.As dye, known dye can be used, for example, can enumerate the known dye of recording in color index (The Society of Dyers and Colourists publishes) and dyeing guide (color dyeing company).In addition, according to chemical structure, can enumerate azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes etc.These dyes can be used alone or in combination of 2 or more use.

[0747] Specifically, dyes with the following color index (CI) numbers are mentioned.

[0748] CI Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;

[0749] CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0750] CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

[0751] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0752] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 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;

[0753] CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0754] 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;

[0755] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182 , 183, 195, 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;

[0756] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

[0757] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0758] 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, 1 26, 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, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;

[0759] 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,

[0760] CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

[0761] 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;

[0762] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0763] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0764] 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, 86, 87, 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, 1 67, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 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;

[0765] CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and other CI direct dyes,

[0766] CI Disperse Yellow 51, 54, 76;

[0767] CI Disperse Violet 26, 27;

[0768] CI disperse blue 1, 14, 56, 60 and other CI disperse dyes,

[0769] CI Basic Red 1, 10;

[0770] 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;

[0771] CI Basic Violet 2;

[0772] CI Basic Red 9;

[0773] CI Basic Green 1; etc. CI basic dyes,

[0774] CI Reactive Yellow 2, 76, 116;

[0775] CI Reactive Orange 16;

[0776] CI Reactive Red 36; etc. CI reactive dyes,

[0777] CI Acid Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0778] CI Acid Mordant 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;

[0779] CI Acid Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0780] CI Acid 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;

[0781] CI Acid Mordant 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, 77, 83, 84;

[0782] CI Acid Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other CI Acid Mordant Dyes,

[0783] CI vat dyes such as CI vat green 1, etc.

[0784] In addition, Lumogen (registered trademark) which is a product of BASF can be mentioned, and examples thereof include Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), Lumogen (registered trademark) F Range 240 (manufactured by BASF), and Lumogen (registered trademark) F Red 305 (manufactured by BASF).

[0785] In addition, there can be mentioned compounds represented by formula (z) and compounds represented by formula (z1).

[0786]

[0787] As the pigment, a known pigment can be used, and for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be mentioned. These can be used alone or in combination of two or more.

[0788] Specifically, yellow pigments such as 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, and 231 can be mentioned;

[0789] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;

[0790] CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273 and other red pigments;

[0791] CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;

[0792] CI Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments;

[0793] CI Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments;

[0794] CI Pigment Brown 23, 25 and other brown pigments;

[0795] CI Pigment Black 1, 7, 31, 32 and other black pigments.

[0796] As the colorant (A1), yellow dyes and yellow pigments (hereinafter, they may be collectively referred to as "yellow colorants"), orange dyes and orange pigments (hereinafter, they may be collectively referred to as "orange colorants"), red dyes and red pigments (hereinafter, they may be collectively referred to as "red colorants"), and green dyes and green pigments (hereinafter, they may be collectively referred to as "green colorants") are preferred, yellow colorants and green colorants are more preferred, yellow pigments and green pigments are further preferred, and green pigments are particularly preferred.

[0797] As yellow dyes, dyes classified as yellow in the above dyes can be cited, and as yellow pigments, pigments classified as yellow in the above pigments can be cited. As yellow colorants, yellow dyes and yellow pigments are preferred, yellow pigments are more preferred, quinophthalone pigments, metal-containing pigments, isoindoline pigments are further preferred, CI Pigment Yellow 129, 138, 139, 150, 185, 231 are particularly preferred, and CI Pigment Yellow 138, 139, 150, 185, 231 are further preferred.

[0798] As orange dye, dyes classified as orange in the above dyes can be cited, and as orange pigments, pigments classified as orange in the above pigments can be cited. As orange colorants, orange dyes and orange pigments are preferred, orange pigments are more preferred, and CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 are further preferred.

[0799] As red dyes, dyes whose hue is classified as red among the above dyes can be cited, and as red pigments, pigments whose hue is classified as red among the above pigments can be cited. As red colorants, red dyes and red pigments are preferred, and azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane dyes, xanthene pigments and perylene pigments are more preferred, and CI Acid Red 52, CI Pigment Red 144, 177, 179, 242, 254 and 269 are further preferred.

[0800] In addition, as the yellow colorant, the orange colorant, or the red colorant, the xanthene compounds described in JP-A-2013-235257 and the like can be used.

[0801] As green dyes, dyes whose hue is classified as green among the above dyes can be cited, and as green pigments, pigments whose hue is classified as green among the above pigments can be cited. As green colorants, green dyes and green pigments are preferred, green pigments are more preferred, phthalocyanine pigments are further preferred, halogenated copper phthalocyanine pigments, halogenated zinc phthalocyanine pigments and halogenated aluminum zinc phthalocyanine pigments are particularly preferred, and CI Pigment Green 7, 36, 58, 59, 62 and 63 are further preferred.

[0802] [Preparation of a solution containing a colorant (A1)]

[0803] When the coloring composition of the present invention contains a colorant (A1), a solution containing a colorant (A1) and a solvent (E) may be prepared in advance, and then the coloring composition may be prepared using the solution containing the colorant (A1). When the colorant (A1) is not dissolved in the solvent (E), the solution containing the colorant (A1) may be prepared by dispersing and mixing the colorant (A1) in the solvent (E). The solution containing the colorant (A1) may contain a part or all of the solvent (E) contained in the coloring composition.

[0804] The content of the solid content in the solution containing the colorant (A1) is less than 100 mass % relative to the total amount of the solution containing the colorant (A1), preferably 0.01 mass % to 99.99 mass %, more preferably 0.1 mass % to 99.9 mass %, further preferably 0.1 mass % to 99 mass %, particularly preferably 1 mass % to 90 mass %, further preferably 1 mass % to 80 mass %, particularly preferably 1 mass % to 70 mass %, extremely preferably 1 mass % to 60 mass %, and most preferably 1 mass % to 50 mass %.

[0805] The content of the colorant (A1) in the solution containing the colorant (A1) is 100% by mass or less, preferably 0.0001% by mass to 99.9999% by mass, more preferably 0.0001% by mass to 99% by mass, further preferably 1% by mass to 99% by mass, particularly preferably 3% by mass to 99% by mass, and further preferably 5% by mass to 99% by mass, based on the total amount of solid content in the solution containing the colorant (A1).

[0806] The colorant (A1) may be subjected to rosin treatment, surface treatment using a derivative introduced with an acidic group or a basic group, grafting treatment on the surface of the colorant (A1) using a polymer compound, etc., micronization treatment using a sulfuric acid micronization method, a salt milling method, etc., washing treatment using an organic solvent, water, etc. for removing impurities, crystal structure conversion similar to compound (I), particle shaping and / or particle size roughly uniformization treatment, ionic impurity removal treatment using an ion exchange method, etc. The particle size of the colorant (A1) is preferably roughly uniform.

[0807] The colorant (A1) can be dispersed in a solution containing a dispersant so that the colorant (A1) is uniformly dispersed. The colorant (A1) can be dispersed alone or in a mixture of two or more.

[0808] As dispersant, surfactant etc. can be enumerated, and can be any surfactant in cationic, anionic, nonionic and amphoteric. Specifically, surfactants such as polyester, polyamine and acrylic acid can be enumerated. These dispersants can be used alone or mixed with 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 system), AJISPER (registered trademark) (Ajinomoto Fine Chemicals (Strain) system), DISPERBYK (registered trademark) (BYK-Chemie (Strain) system) and BYK (registered trademark) (BYK-Chemie (Strain) system) etc. can be enumerated.

[0809] When the solution containing the colorant (A1) contains a dispersant, the amount of the dispersant (solid content) used is, for example, 0.01 to 10,000 parts by mass, preferably 0.01 to 5,000 parts by mass, more preferably 0.01 to 1,000 parts by mass, further preferably 0.1 to 500 parts by mass, particularly preferably 0.1 to 300 parts by mass, further preferably 1 to 300 parts by mass, and particularly preferably 5 to 260 parts by mass, relative to 100 parts by mass of the colorant (A1). When the amount of the dispersant used is within the above range, there is a tendency to obtain a solution containing the colorant (A1) in a more uniform dispersed state.

[0810] The colored composition of the present invention contains a resin (B), and a solution containing a colorant (A1) containing a colorant (A1) and a solvent (E) is prepared in advance. When the colored composition of the present invention is prepared using the solution containing the colorant (A1), the solution containing the colorant (A1) may contain a part or all, preferably a part, of the resin (B) contained in the colored composition in advance. By containing the resin (B) in advance, the dispersion stability of the solution containing the colorant (A1) can be further improved.

[0811] When the solution containing the colorant (A1) contains the resin (B), the content of the resin (B) is, for example, 0.01 to 10,000 parts by mass, preferably 0.01 to 5,000 parts by mass, more preferably 0.01 to 1,000 parts by mass, further preferably 0.1 to 500 parts by mass, particularly preferably 0.1 to 300 parts by mass, based on 100 parts by mass of the colorant (A1).

[0812] When the colored composition of the present invention contains a colorant (A1), the content of the colorant (A) in total of the compound (I) and the colorant (A1) in the colored composition is less than 100% by mass, preferably 0.0001% by mass to 99.9999% by mass, more preferably 0.0001% by mass to 99% by mass, further preferably 0.0001% by mass to 90% by mass, particularly preferably 0.0001% by mass to 80% by mass, further preferably 0.0001% by mass to 70% by mass, particularly preferably 0.0001% by mass to 60% by mass, extremely preferably 0.0001% by mass to 55% by mass, and most preferably 0.1% by mass to 55% by mass.

[0813] When the colored composition of the present invention contains a colorant (A1), the content of the compound (I) is usually 0.0001% by mass or more, preferably 0.0003% by mass or more, more preferably 0.0005% by mass or more, and even more preferably 0.001% by mass or more in the total amount of the colorant (A), and the upper limit is less than 100% by mass, preferably 99.9999% by mass or less, more preferably 99% by mass or less, further preferably 98% by mass or less, and particularly preferably 97% by mass or less.

[0814] [Leveling agent (F)]

[0815] 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.

[0816] 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.).

[0817] 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.), MEGAFACE (registered trademark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE 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.

[0818] Examples of the organosilicon-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, and more specifically, MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Corporation).

[0819] When a leveling agent (F) is contained, its content is usually 0.00001% to 5% by mass, preferably 0.00001% to 3% by mass, more preferably 0.0001% to 2% by mass, and further preferably 0.0001% to 1% by mass, relative to the total amount of the colored composition. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0820] [Antioxidant (G)]

[0821] From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferred that an antioxidant is used alone or in combination of two or more. As the antioxidant, there is no particular limitation as long as it is an antioxidant generally used in industry, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, etc. can be used.

[0822] Examples of the phenolic antioxidant include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF), Irganox 1330 (Irganox 1330: 3,3',3",5,5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-triyl)tri-p-cresol, manufactured by BASF), and Irganox 3114 (Irganox 3115: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF). 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF), Irganox 3790 (Irganox 3790: 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF), Irganox 1035 (Irganox 1035: thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF), Irganox 1135 (Irganox 1135: phenylpropane acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF), Irganox 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF), Irganox 3125 (Irganox 3125, manufactured by BASF), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy 3',5'-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF), ADK STABAO-80 (ADK STAB AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, manufactured by ADEKA Corporation), Sumilizer BHT (Sumilizer BHT, manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (Cyanox 1790, manufactured by Sitech Corporation), and vitamin E (manufactured by Eisai Corporation).

[0823] Examples of the phosphorus-based antioxidant include Irgafos 168 (Irgafos 168: tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF), Irgafos 12 (Irgafos 12: tris[2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphin-6-yl]oxy]ethyl]amine, manufactured by BASF), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl phosphite, manufactured by BASF), ADK STAB 329K (manufactured by ADEKA Corporation), ADK STAB PEP36 (manufactured by ADEKA Corporation), ADK STAB PEP-8 (manufactured by ADEKA Corporation), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (Weston618, manufactured by GE), Weston 619G (Weston 619G, manufactured by GE), Ultranox 626 (Ultranox 626, manufactured by GE), and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1.3.2]dioxaphosphapin) (manufactured by Sumitomo Chemical Co., Ltd.), etc.

[0824] Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and β-alkylmercaptopropionate compounds of polyhydric alcohols such as tetrakis[methylene(3-dodecylthio)propionate]methane.

[0825] [Other ingredients]

[0826] The colored composition of the present invention may contain fillers, and additives known in the technical field such as other polymer compounds, adhesion promoters, light stabilizers, and chain transfer agents, as necessary.

[0827] Examples of the adhesion promoter include vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tri(2-methoxyethoxy)silane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 3-glycidoxypropyl methyl diethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-chloropropyl trimethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, and 3-sulfanylpropyl trimethoxysilane. trimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane.

[0828] [Method for producing coloring composition]

[0829] The coloring composition of the present invention can be prepared by mixing, for example, the compound (I), the solvent (E), and, if necessary, the resin (B), the polymerizable compound (C), the polymerization initiator (D), the polymerization initiation aid (D1), the colorant (A1), the leveling agent (F), the antioxidant (G) and / or other components. The mixing can be performed using a known or customary apparatus and conditions.

[0830] The compound (I) is preferably used in the form of a solution containing the compound (I) which is mixed with a part or all of the solvent (E) and dispersed by a bead mill etc. until the average particle size of the compound (I) is about 0.2 μm or less. In this case, a part or all of the above-mentioned dispersant and resin (B) may be added as needed.

[0831] The colorant (A1) is preferably used in a state of a solution containing the colorant (A1) which is pre-mixed with a part or all of the solvent (E) and dispersed by a bead mill until the average particle size of the colorant (A1) is about 0.2 μm or less. In this case, a part or all of the above-mentioned dispersant and resin (B) may be added as needed.

[0832] Compound (I) is preferably used in the form of a solution preliminarily dissolved in part or all of the solvent (E) (the solution is included in the solution containing compound (I)). The solution containing compound (I) is preferably further filtered through a filter having a pore size of about 0.01 μm to 1 μm.

[0833] The colorant (A1) is preferably used in the form of a solution preliminarily dissolved in part or all of the solvent (E) (the solution is included in the solution containing the colorant (A1)). The solution containing the colorant (A1) is preferably further filtered through a filter having a pore size of about 0.01 μm to 1 μm.

[0834] The mixed colored composition is preferably filtered through a filter having a pore size of about 0.01 μm to 10 μm.

[0835] [Color Filter]

[0836] A color filter can be formed from the coloring composition of the present invention.

[0837] The coloring composition is applied to a substrate, and volatile components such as a solvent are removed and dried to form a color coating film. The color coating film formed in this way is included in the color filter of the present invention.

[0838] As a method for forming a colored pattern, photolithography, inkjet method, printing method, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method in which the above-mentioned colored composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film as a cured product of the above-mentioned colored composition layer can be formed without using a photomask and / or developing during exposure. The colored pattern and colored coating film formed in this way are the color filter of the present invention.

[0839] The film thickness of the produced color filter is not particularly limited and can be appropriately adjusted depending on the purpose and application, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0840] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass with silicon dioxide coated on the surface, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or a substrate having aluminum, silver, or a silver / copper / palladium alloy thin film formed thereon can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates.

[0841] The formation of each color pixel by photolithography can be performed using a known or customary device and conditions. For example, the formation can be performed as follows.

[0842] First, a coloring composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure, thereby obtaining a smooth coloring composition layer.

[0843] Examples of the coating method include spin coating, slit coating, and slit-spin coating.

[0844] The temperature for heat drying is preferably 30 to 120° C., more preferably 50 to 110° C. In addition, the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When the reduced pressure drying is performed, it is preferably performed at a pressure of 50 to 150 Pa and a temperature range of 20 to 25° C. The film thickness of the coloring composition layer is not particularly limited, and can be appropriately selected according to the film thickness of the target color filter.

[0845] Next, the colored composition layer is exposed through a photomask for forming a target colored pattern.

[0846] 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 generates light with a wavelength of 250 to 450 nm is preferred. For example, light less than 350 nm can be cut off using a filter that cuts off this 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. Specific examples of light sources include mercury lamps, light emitting diodes, metal halide lamps, and halogen lamps.

[0847] In order to uniformly irradiate the entire exposure surface with parallel light and accurately align the photomask and the substrate on which the colored composition layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

[0848] The colored composition layer after exposure is brought into contact with a developer and developed, thereby forming a colored pattern on the substrate. The unexposed portion of the colored composition layer is dissolved in the developer and removed by the development.

[0849] As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable.

[0850] The concentration of the basic compound is preferably 0.01 to 10% by mass, more preferably 0.02 to 5% by mass. The developer may contain a surfactant.

[0851] The developing method may be any of a paddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be tilted at an arbitrary angle during the developing process.

[0852] The substrate after development is preferably washed with water.

[0853] It is further preferred to post-bake the obtained colored pattern.

[0854] The post-baking temperature is preferably 150 to 250° C., more preferably 160 to 235° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes. The color filter as the color pattern or color coating film thus obtained may be further subjected to a surface coating treatment in order to impart various properties.

[0855] 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, electronic paper, etc.) and a solid-state imaging element, particularly a color filter used in a liquid crystal display device.

[0856] Example

[0857] Hereinafter, the present invention will be described in more detail by giving examples, and 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, and these are all included in the technical scope of the present invention. It should be noted that, below, "part" means "part by mass", and "%" means "% by mass", unless otherwise specified.

[0858] In the following synthesis examples, the structures of the compounds were confirmed by mass spectrometry (LC; Model 1200 manufactured by Agilent, MASS; Model LC / MSD6130 manufactured by Agilent).

[0859] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.

[0860] Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)

[0861] Column: TSK-GELG2000HXL

[0862] Column temperature: 40°C

[0863] Solvent: Tetrahydrofuran

[0864] Flow rate: 1.0mL / min

[0865] Solid content concentration of the analysis sample: 0.001 to 0.01 mass%

[0866] Injection volume: 50 μL

[0867] Detector: RI

[0868] Calibration standard substances: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0869] The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight (Mw) and the number average molecular weight (Mn) obtained above was defined as the degree of dispersion.

[0870] Synthesis Example A

[0871] 3.67 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.59 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.4 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 84.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed.

[0872] The mixture was maintained at 170°C and stirred for 10 hours.

[0873] To this mixture were added 7.92 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 15.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 45 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0874] The mixture was maintained at 170°C and stirred for 9 hours.

[0875] To this mixture was added 9 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0876] The mixture was maintained at 170°C and stirred for 18 hours.

[0877] To this mixture were added 7.77 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 11.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0878] The mixture was kept at 170°C and stirred for 27 hours.

[0879] To this mixture were added 3.88 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.33 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 12.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0880] The mixture was maintained at 170°C and stirred for 8 hours.

[0881] The mixture was cooled to room temperature, and 2800 parts of methanol was added to the mixture.

[0882] The obtained mixture was stirred at room temperature and then filtered.

[0883] The obtained residue was washed twice with 400 parts of methanol and once with 800 parts of methanol.

[0884] The obtained residue was dried under reduced pressure at 60°C to obtain 7.67 parts of the compound represented by formula (Ia1).

[0885]

[0886] <Identification of the compound represented by formula (Ia1)>

[0887] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 419

[0888] (Mass analysis) Ionization mode = ESI-: m / z = [M-H] - 417

[0889] Exact molecular weight: 418

[0890] Synthesis Example B

[0891] A mixture of 1 mol of the compound represented by the formula (Ia1), 20 mol of potassium hydroxide and water in an amount 10 times the weight of 1 mol of the compound represented by the formula (Ia1) is mixed.

[0892] The mixture was maintained at 90°C and stirred until the compound represented by formula (Ia1) disappeared.

[0893] The mixture was mixed with 36% hydrochloric acid to neutralize it.

[0894] The mixture was filtered.

[0895] The obtained residue was washed with water.

[0896] The residue was purified by column chromatography to obtain a compound represented by formula (IM1-6).

[0897]

[0898] <Identification of the compound represented by formula (IM1-6)>

[0899] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 289

[0900] (Mass analysis) Ionization mode = ESI-: m / z = [M-H] － 287

[0901] Exact molecular weight: 288

[0902] Example D-1

[0903] Mix 1 mol of the compound represented by formula (IM1-6), 0.5 mol of 4,4'-oxydiphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 73 times the weight of 1 mol of the compound represented by formula (IM1-6) by weight of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). Keep the mixture at 170°C and stir for 120 hours. Cool the mixture to room temperature, and add methanol 13 times the weight of the mixture to the mixture. After stirring the obtained mixture at room temperature, filter it, and wash the obtained residue with methanol.

[0904] The obtained residue was purified by column chromatography to obtain the compound represented by formula (Ip16).

[0905]

[0906] <Identification of the compound represented by formula (Ip16)>

[0907] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 851

[0908] (Mass analysis) Ionization mode = ESI-: m / z = [M-H] － 849

[0909] Exact molecular weight: 850

[0910] Example D-2

[0911] A compound represented by formula (Ip4) was obtained in the same manner as in Example D-1 except that 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4,4'-oxydiphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0912]

[0913] <Identification of the compound represented by formula (Ip4)>

[0914] (Mass analysis) Ionization mode = ESI+: m / z = [M+H] + 985

[0915] (Mass analysis) Ionization mode = ESI-: m / z = [M-H] － 983

[0916] Exact molecular weight: 984

[0917] [Identification of Compounds]

[0918] The structure of the compound was identified by mass spectrometry (LCMS, LC; Agilent 1200 model, MASS; Agilent LC / MSD model) and mass spectrometry (MALDI-TOFMS; JMS-S3000 manufactured by JEOL Ltd.).

[0919] Synthesis Example C

[0920] 2.27 parts of the compound represented by formula (Ia1), 35.00 parts of isobutyl alcohol, and 1.28 parts of hydrazine monohydrate were added, heated to 100°C and stirred for 3 hours. After the reaction, the mixture was cooled to room temperature, poured into 75 parts of methanol, and the obtained crystals were filtered out. Vacuum drying was performed to obtain 2.0 parts of a light orange powder. The obtained powder was mass analyzed by LCMS and confirmed to be the compound represented by formula (IM1-6).

[0921] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 289

[0922] Exact molecular weight: 288

[0923]

[0924] Example D-3

[0925] 1.00 parts of the powder obtained in Synthesis Example C, 0.55 parts of 4,4'-oxydiphthalic anhydride, and 3.65 parts of benzoic acid were placed in a nitrogen-substituted flask, heated to 220°C, and stirred for 4 hours. After the reaction, it was cooled to room temperature, poured into 80 parts of methanol / 50 parts of ion exchange water, and the obtained crystals were filtered out. The obtained crystals were added to 50 parts of methanol / 40 parts of ion exchange water and vacuum dried to obtain 1.06 parts of yellow powder. The obtained yellow powder was mass analyzed by MALDI-TOFMS, and it was confirmed that it contained the compound represented by formula (Ip16).

[0926] (Mass Spectrometry)

[0927] Ionization mode = MALDI (Positive): m / z = [M+H] + 851

[0928] Exact molecular weight: 850

[0929]

[0930] Example D-4

[0931] 0.98 parts of the powder obtained in Synthesis Example C, 0.77 parts of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, and 3.58 parts of benzoic acid were placed in a nitrogen-substituted flask, heated to 220°C, and stirred for 5 hours. After the reaction, it was cooled to room temperature, poured into 80 parts of methanol / 50 parts of ion exchange water, and the obtained crystals were filtered out. Vacuum drying was performed to obtain 1.32 parts of yellow powder. The obtained crystals were repeatedly re-pulped and washed with methanol, and vacuum dried to obtain 0.77 parts of bright yellow powder. The obtained bright yellow powder was mass analyzed by MALDI-TOFMS, and it was confirmed that it contained the compound represented by formula (Ip4).

[0932] (Mass Spectrometry)

[0933] Ionization mode = MALDI (Positive): m / z = [M+H] + 985

[0934] Exact molecular weight: 984

[0935]

[0936] Example D-5

[0937] 1.00 parts of the powder obtained in Synthesis Example C, 0.25 parts of pyromellitic anhydride, 1.10 parts of benzoic acid, and 2.20 parts of methyl benzoate were placed in a nitrogen-substituted flask, heated to 180°C, and stirred for 4 hours. After the reaction, the mixture was cooled to room temperature, and 17 parts of methanol were added and stirred. The mixture was added dropwise to 67 parts of methanol while stirring. The precipitate obtained by filtering it was washed with tetrahydrofuran, N,N-dimethylformamide, and methanol, and then vacuum dried to obtain 0.72 parts of yellow powder. The obtained yellow powder was subjected to mass spectrometry analysis using MALDI-TOFMS, and it was confirmed that it contained the compound represented by formula (Ip164).

[0938] (Mass Spectrometry)

[0939] Ionization mode = MALDI (Positive): m / z = [M+H] + 759

[0940] Exact molecular weight: 758

[0941]

[0942] Example D-6

[0943] 1.00 parts of the powder obtained in Synthesis Example C, 0.29 parts of 1,2,4,5-cyclohexanetetracarboxylic anhydride, 2.72 parts of benzoic acid, and 4.80 parts of methyl benzoate were placed in a nitrogen-substituted flask, heated to 180°C, and stirred for 17 hours. After the reaction, the mixture was cooled to room temperature, and 11 parts of methanol were added and stirred. The precipitate obtained by filtering the mixture was washed with methanol and vacuum dried to obtain 0.79 parts of yellow powder. The obtained yellow powder was subjected to mass spectrometry analysis using a liquid chromatograph / mass spectrometer, and it was confirmed that it contained a compound represented by formula (Ip6000).

[0944] (Mass Spectrometry)

[0945] Ionization mode = ESI (Positive): m / z = [M+H] + 765

[0946] Exact molecular weight: 764

[0947]

[0948] Synthesis Example A-2

[0949] The compound represented by formula (Ia2) was synthesized by the method described in JP-A-2020-132878.

[0950]

[0951] Synthesis Example B-2

[0952] A compound represented by formula (IM1-7) was synthesized by the same method as in Synthesis Example B except that the compound represented by formula (Ia2) was used instead of the compound represented by formula (Ia1).

[0953]

[0954] Example D-7

[0955] 1.00 parts of the powder obtained in Synthesis Example B-2, 0.24 parts of pyromellitic anhydride, 1.05 parts of benzoic acid, and 2.14 parts of methyl benzoate were placed in a nitrogen-substituted flask, heated to 180°C, and stirred for 5 hours. After the reaction, the mixture was cooled to room temperature, and 16 parts of methanol were added and stirred. The mixture was added dropwise to 29 parts of methanol while stirring. The precipitate obtained by filtering it was washed with tetrahydrofuran, N,N-dimethylformamide, and toluene, and then vacuum dried to obtain 0.76 parts of yellow powder. The obtained yellow powder was subjected to mass spectrometry analysis using MALDI-TOFMS, and it was confirmed that it contained the compound represented by formula (Ip1156).

[0956] (Mass Spectrometry)

[0957] Ionization mode = MALDI (Positive): m / z = [M+H] + 787

[0958] Exact molecular weight: 786

[0959]

[0960] Synthesis Example A-3

[0961] The compound represented by formula (Ia3) was synthesized by the method described in JP-A-2020-132878.

[0962]

[0963] Synthesis Example B-3

[0964] A compound represented by formula (IM1-8) was synthesized by the same method as in Synthesis Example B except that the compound represented by formula (Ia3) was used instead of the compound represented by formula (Ia1).

[0965]

[0966] Example D-8

[0967] 1.00 parts of the powder obtained in Synthesis Example B-3, 0.34 parts of pyromellitic anhydride, 1.49 parts of benzoic acid, and 1.50 parts of methyl benzoate were placed in a nitrogen-substituted flask, heated to 180°C, and stirred for 5 hours. After the reaction, the mixture was cooled to room temperature, and 14 parts of methanol were added and stirred. The precipitate obtained by filtering the mixture was washed with tetrahydrofuran and vacuum dried to obtain 1.10 parts of yellow powder. The obtained yellow powder was subjected to mass spectrometry analysis using MALDI-TOFMS, and it was confirmed that it contained the compound represented by formula (Ip412).

[0968] (Mass Spectrometry)

[0969] Ionization mode = MALDI (Positive): m / z = [M+H] + 859

[0970] Exact molecular weight: 858

[0971]

[0972] Synthesis example 1

[0973] An appropriate 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, and 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixed solution of 289 parts of a mixture of decane-9-yl acrylate (containing a ratio of 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B1) with a solid content of 35.0%. The weight average molecular weight of the obtained resin B1 was 8800, the degree of dispersion was 2.1, and the acid value converted to solid content was 80 mg-KOH / g.

[0974] Synthesis example 2

[0975] An appropriate 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, and 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, 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixed solution of 54 parts of a mixture of decane-9-yl acrylate (containing a ratio of 1:1 by molar ratio), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution of 40 parts of 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 was completed, the mixture was kept at 80°C for 3 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B2) with a solid content of 36.8%. The weight average molecular weight of the obtained copolymer was 9400, the degree of dispersion was 1.89, and the acid value converted to solid content was 114 mg-KOH / g.

[0976] Example E-1

[0977] The components were mixed at the following ratios, and the colorant was dispersed using a bead mill to obtain a coloring composition ME-1.

[0978]

[0979]

[0980] Next, each component was mixed at the following ratio to obtain a colored composition E-1.

[0981]

[0982] The coloring composition E-1 was applied on a 2-inch square glass substrate (EAGLE XG; manufactured by CORNING) by a spin coating method, and then prebaked at 100° C. for 3 minutes to form a prebaked color coating film.

[0983] The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured in the range of 380 nm to 780 nm at a scale of 1 nm using a colorimeter LVmicroZ (manufactured by Lambda Vision Corporation).

[0984] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[0985] The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

[0986] Example E-2

[0987] A coloring composition E-2 was obtained in the same manner as in Example E-1 except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip4) obtained in Example D-2, and a prebaked color coating film and a postbaked color coating film were obtained.

[0988] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[0989] Example E-3

[0990] A coloring composition E-3 was obtained in the same manner as in Example E-1 except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip164) obtained in Example D-5, and a prebaked color coating film and a postbaked color coating film were obtained.

[0991] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[0992] Example E-4

[0993] A coloring composition E-4 was obtained in the same manner as in Example E-1 except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip6000) obtained in Example D-6, and a prebaked color coating film and a postbaked color coating film were obtained.

[0994] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[0995] Example E-5

[0996] A coloring composition E-5 was obtained in the same manner as in Example E-1 except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip1156) obtained in Example D-7, and a prebaked color coating film and a postbaked color coating film were obtained.

[0997] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[0998] Example E-6

[0999] A coloring composition E-6 was obtained in the same manner as in Example E-1 except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip412) obtained in Example D-8, and a prebaked color coating film and a postbaked color coating film were obtained.

[1000] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[1001] Comparative Example 1

[1002] A coloring composition E-7 was obtained in the same manner as in Example E-1 except that the compound represented by formula (Ip16) was replaced with CI Pigment Yellow 138 (Paliotol Gelb L0962HD manufactured by BASF), and a prebaked color coating film and a postbaked color coating film were obtained.

[1003] Table AD5 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

[1004] [Table AD5]

[1005]

[1006] From the above results, it can be seen that the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing the compound of the present invention or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum is longer than the maximum absorption wavelength (458 nm) on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing CI Pigment Yellow 138.

[1007] [Preparation Examples 1 to 7]

[1008] [Preparation of Coloring Composition]

[1009] The colored composition can be obtained by mixing the components so as to have the composition shown in Table AD6. The unit of the numerical value is part by mass.

[1010] [Table AD6]

[1011]

[1012] In Table AD6, the components are as follows.

[1013] Coloring composition E-1: Coloring composition E-1 described in Example E-1

[1014] Coloring composition E-2: Coloring composition E-2 described in Example E-2

[1015] Coloring composition E-3: Coloring composition E-3 described in Example E-3

[1016] Coloring composition E-4: Coloring composition E-4 described in Example E-4

[1017] Coloring composition E-5: Coloring composition E-5 described in Example E-5

[1018] Coloring composition E-6: Coloring composition E-6 described in Example E-6

[1019] Coloring composition E-7: Coloring composition E-7 described in Comparative Example 1

[1020] Resin (B): Resin B1 (solid content)

[1021] Polymerizable compound (C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[1022] Polymerization initiator (D-1): N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine (PBG-327; oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.)

[1023] Solvent (E): Propylene glycol monomethyl ether acetate

[1024] Leveling agent (F): polyether-modified silicone oil ("Toray Silicone SH8400" manufactured by Dow Corning Toray Co., Ltd.) (solid content)

[1025] <Production of color filters (colored coatings)>

[1026] The coloring composition was applied on a 5 cm square glass substrate (EAGLE 2000; manufactured by CORNING) by spin coating, and then pre-baked at 100°C for 3 minutes to form a coloring composition layer. After cooling, the coloring composition layer formed on the substrate was exposed to light at 100 mJ / cm in an air atmosphere using an exposure machine (TME-150RSK; manufactured by TOPCON Corporation). 2 After the light irradiation, the film was post-baked in an oven at 230° C. for 30 minutes to obtain a colored coating film.

[1027] Industrial Applicability

[1028] The colored composition and compound of the present invention can be used to form a color filter with a darker color than a colored composition containing CI Pigment Yellow 138, and therefore are preferably used in a color filter or a display device such as a liquid crystal display device.

Claims

1. A compound represented by the following formula (Ip), In formula (Ip), C b11 , C b21 , C b31 , C b41 Respectively represent and L 1 The carbon atoms that form the bond, In any L represented by formula (da1) to formula (da27), formula (db1) to formula (db16), formula (dc1) to formula (dc52), formula (dd1) to formula (dd68), formula (de1) to formula (de31), formula (de33) to formula (de45), formula (de47) to formula (de77), formula (de84) to formula (de86), and formula (dh1) to formula (dh13), 1 In the group, the bonding site represented by b1 is b11 The bonding site represented by b2 forms a bond with C b21 The bonding site represented by b3 forms a bond with C b31 The bonding site represented by b4 forms a bond with C b41 Forming a bond, Q d11 and Q d21 each independently represents benzene, benzene having a methyl group, or naphthalene, 2. A coloring composition comprising the compound according to claim 1 and a resin.

3. The coloring composition according to claim 2, wherein Contains a polymerizable compound and a polymerization initiator. 4 . A color filter formed from the coloring composition according to claim 2 .

5. A display device comprising the color filter according to claim 4.

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