TWI881035B - Coloring composition, compound, color filter and display device - Google Patents

Abstract

The object of the present invention is to provide a compound having a maximum absorption wavelength on the longest wavelength side of an absorption spectrum at a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the previously 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 at least one of ^Q1 and ^Q2 is a group represented by formula (QQ20)).

Description

Coloring composition, compound, color filter and display device

The present invention relates to a coloring composition, a compound, a color filter and a display device.

The coloring composition can be used to manufacture color filters used in display devices such as liquid crystal display devices and electroluminescent display devices. As a coloring agent contained in the coloring composition, C.I. Pigment Yellow 138 is known (Patent Document 1).

[Prior art literature] [Patent Literature]

[Patent document 1] Japanese Patent Publication No. 2013-82906

In recent years, the development of displays for expanding the color reproduction area that can be displayed has been advancing, and as part of this, color filters are also required to have richer colors. In order to meet this requirement, a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum at a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the previously known C.I. 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.

The wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum refers to: for a compound, when there is no 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 C.I. Pigment Yellow 138, and when there are 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, the wavelength is 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.

The present invention provides the following [1]~[5].

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

[In formula (I), R ¹ to R ⁵ independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring; 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 ); MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ to Z ⁴ independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² may also independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH ₂ - may also be substituted with -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; when there are plural Z ¹ to Z ⁴ , M and MM, they may be the same or different; at least one of Q ¹ and Q ² is a group represented by formula (QQ20);

[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; L represents a (2p+2q+2)-valent alkyl group or a (2p+2q+2)-valent heterocyclic group, -C(-)(-)- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -N(-)-, and -CH= constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -N=, _-CH2- constituting the (2p+2q+2)-valent hydroxyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -O-, -S-, -S(O) _2- or -CO-, and the hydrogen atom constituting the (2p+2q+2)-valent hydroxyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M or MM; ^Q3 and Q ⁴ independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q95 to R ^Q104 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-; The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q95 to R ^Q104 may each bond to one or more selected from R ^Q95 to R ^Q104 to form a ring; M and MM have the same meanings as described above; ※ represents a bond; when Q ³ , Q ⁴ , R ^Q95 to R ^Q104 , M and MM exist in plural numbers, they may be the same or different from each other]].

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

[3] The coloring composition described in [2] comprises a polymerizable compound and a polymerization initiator.

[4] A color filter, which is formed by the coloring composition as described in [2] or [3].

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

According to the present invention, a coloring composition and a compound are provided that can be used in the formation of a color filter having a darker color than a coloring composition containing C.I. Pigment Yellow 138.

[Coloring composition]

The coloring composition of the present invention comprises: a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a resin (hereinafter, sometimes referred to as resin (B)).

[In formula (I), R ¹ to R ⁵ independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring; 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 ); MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ to Z ⁴ independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² may independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-; the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; when there are plural Z ¹ to Z ⁴ , M and MM, they may be the same or different; at least one of Q ¹ and Q ² is a group represented by formula (QQ20);

[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; L represents a (2p+2q+2)-valent alkyl group or a (2p+2q+2)-valent heterocyclic group, -C(-)(-)- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -Si(-)(-)-, and -CH(-)- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -N(-)-, -CH= constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -N=, -CH2- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by -O-, -S-, -S(O) _2- or -CO-, _and the hydrogen atom constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M or MM; ^Q3 and Q ⁴ independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q95 to R ^Q104 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q95 ~R ^Q104 may be bonded to one or more selected from R ^Q95 ~R ^Q104 to form a ring; M and MM have the same meanings as described above; ※ represents a bond; when Q ³ , Q ⁴ , R ^Q95 ~R ^Q104 , M and MM exist in plural numbers, they may be the same or different from each other]]

Compound (I) also includes its tautomers or their salts.

Compound (I) can be used as a coloring agent.

The coloring composition of the present invention may contain one or more compounds (I).

The coloring composition of the present invention may also contain a solvent (hereinafter referred to as solvent (E)).

The coloring composition of the present invention may also contain a polymerizable compound (hereinafter referred to as a polymerizable compound (C)).

The coloring composition of the present invention may also contain a polymerization initiator (hereinafter referred to as a polymerization initiator (D)).

The coloring composition of the present invention may also contain a polymerization initiator (hereinafter referred to as a polymerization initiator (D1)).

The coloring composition of the present invention may also contain a coloring agent other than compound (I) (hereinafter, it may be referred to as coloring agent (A1); and, hereinafter, compound (I) and coloring agent (A1) may be collectively referred to as "coloring agent (A)").

The coloring agent (A1) may contain one or more coloring agents.

The colorant (A1) preferably includes one or more selected from yellow colorants, orange colorants, red colorants, and green colorants.

The coloring composition of the present invention may also contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

The coloring composition of the present invention may also contain an antioxidant (hereinafter referred to as antioxidant (G)).

[Compound (I)]

The following lists partial structures of compound (I) to more specifically illustrate the present invention. In each partial structure, even if the substituent bonded to the ring structure is only exemplified as being bonded to any part of the ring structure, the following examples also include the state where the substituent is bonded to all parts of the ring structure. One or more substituents may be bonded to the ring structure. When two or more substituents are bonded to the ring structure, the substituents may be the same or different.

As the halogen atom, there can be listed: fluorine atom, chlorine atom, bromine atom and iodine atom, etc., preferably fluorine atom, chlorine atom and bromine atom.

The carbon number of the alkyl group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ is 1 to 40, preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 18, and particularly preferably 1 to 12.

The monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ 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).

Examples of the saturated or unsaturated chain hydrocarbon groups represented by ^R1 to ^R5 and ^Z1 to ^Z4 include 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, tricosyl, linear alkyl groups such as dodecyl, trihecondecyl, dotriacontyl, tritriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, heptatriacontyl, octatriacontyl, nonatriacontyl 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-propyl branched chain alkyl groups such as 1-butylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butylhexyl; ethenyl (vinyl), propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1-(2- 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-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 Alkenyl groups such as alkenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 1,1-dimethyl-2-propenyl, 1-ethyl-2-propenyl and 1-methyl-1-butenyl; alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), octynyl (e.g., 1-octynyl, 7-octynyl), butynyl, pentynyl, hexynyl, heptynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecenyl, octadecynyl, nonadecenyl and eicosynyl; and the like. The carbon number of the saturated or unsaturated chain alkyl 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 chain alkyl group having 1 to 12 carbon atoms is particularly preferred.

Examples of the saturated or unsaturated alicyclic alkyl groups represented by ^R1 to ^R5 and ^Z1 to ^Z4 include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3, cycloalkyl groups such as 3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl; saturated or unsaturated polycyclic alkyl groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl, and the like. The carbon number of the saturated or unsaturated alicyclic alkyl group is preferably 3 to 30, 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.

基及芘基等芳香族烴基等。芳香族烴基的碳數較佳為6~30，更佳為6~20，進而佳為6~18，尤佳為6~12。 Examples of the aromatic hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-t-butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 3,5-di(t-butyl)phenyl, 3,5-di(t-butyl)- 4-methylphenyl, 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, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl,

The number of carbon atoms in the aromatic alkyl group is preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 18, and particularly preferably 6 to 12.

The alkyl group represented by ^R1 to ^R5 and ^Z1 to ^Z4 may be a group formed by combining the alkyl groups listed above (for example, an aromatic alkyl group, and at least one of a chain alkyl group and an alicyclic alkyl 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, 1-phenylethyl, 1,1-diphenylethyl, phenethyl, 1-methyl-1-phenylethyl, (1-naphthyl)methyl, and (2-naphthyl)methyl; aralkyl groups such as 1-phenylethenyl, 2-phenylethenyl (phenylethenyl), ... arylalkenyl groups such as phenylethynyl, 2,2-diphenylethenyl, and 2-phenyl-2-(1-naphthyl)ethenyl; 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.

The carbon number of 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.

The groups represented by ^R1 to ^R5 and ^Z1 to ^Z4 may be groups formed by combining the above-mentioned alkyl groups (e.g., chain alkyl groups and alicyclic alkyl groups), for example, alkyl groups bonded to one or more alicyclic alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl and adamantylmethyl.

The carbon number of these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12.

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

The carbon number of the heterocyclic group is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 18, and particularly preferably 3 to 12.

Examples of the heterocyclic ring containing a nitrogen atom include: aziridine, azetidine, pyrrolidine, piperidine, and piperazine; pyrroles such as pyrrole, 1-methylpyrrole, and 2,5-dimethylpyrrole; pyrazoles such as pyrazole, 1-methylpyrrole, 2-methylpyrrole, 3-methylpyrazole, 4-methylpyrazole, and 5-methylpyrazole; imidazole, 1,2,3-triazole, and 1,2,4-triazole; and pyridine, pyrazine, Pyrimidine, 6-methylpyrimidine and other pyrimidines, pyrazine and 1,3,5-triazine and other six-membered unsaturated heterocyclic rings; indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline and other quinoxalines, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine and other condensed tricyclic heterocyclic rings such as carbazole, acridine and phenanthrazine, etc.

Examples of heterocyclic rings containing oxygen atoms include: monocyclic saturated heterocyclic rings such as cyclohexane, cyclohexane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxacyclopentane, 2-cyclopentyldioxacyclopentane; bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, 1,4-dioxaspiro[4.4]nonane; α-acetone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; -valerolactone and other lactone-based heterocyclic rings; furan, 2,3-dimethylfuran, 2,5-dimethylfuran and other five-membered unsaturated heterocyclic rings; 2H-pyran, 4H-pyran and other six-membered unsaturated heterocyclic rings; 1-benzofuran and other benzofurans, benzopyran, 4-methylbenzopyran and other benzopyrans, benzodioxole, 1,3-benzodioxole, benzodioxane, chromane and isochromane and other condensed bicyclic heterocyclic rings; oxanthracene, dibenzofuran and other condensed tricyclic heterocyclic rings, etc.

Examples of the heterocyclic ring containing a sulfur atom include: five-membered saturated heterocyclic rings such as dithiolane; six-membered saturated heterocyclic rings such as thioane, 1,3-dithiane, and 2-methyl-1,3-dithiane; five-membered unsaturated heterocyclic rings such as thiophene, 3-methylthiophene, and 2-carboxythiophene; thiopyrans such as 2H-thiopyran, 4H-thiopyran, and benzothiopyran; condensed bicyclic heterocyclic rings such as benzothiopyran, benzothiopyran, and benzothiophene; and condensed tricyclic heterocyclic rings such as thianthrene and dibenzothiophene.

Examples of heterocyclic rings 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; monocyclic unsaturated heterocyclic rings such as oxazole, 4-methyloxazole, and isoxazoles such as 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, and 5-methylisoxazole; condensed bicyclic heterocyclic rings such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazolinone; condensed tricyclic heterocyclic rings such as phenoxazine, and the like.

Examples of heterocyclic rings containing nitrogen atoms and sulfur atoms include monocyclic heterocyclic rings such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole, 2,4-dimethylthiazole, etc.; condensed bicyclic heterocyclic rings such as benzothiazole, etc.; condensed tricyclic heterocyclic rings such as phenothiazine, etc., etc.

Furthermore, the bonding position of the heterocyclic group is the part from which any hydrogen atom contained in each heterocyclic ring is detached.

The heterocyclic group may also be a group formed by combining the above-mentioned heterocyclic group and the above-mentioned alkyl group, for example, tetrahydrofuranylmethyl group may be listed.

Furthermore, the heterocyclic group may also be represented by the following formula.

※Indicates key binding.

-C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM. The group substituting the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is preferably a halogen atom, a cyano group, a nitro group, -SO ₃ H, or -CO ₂ H. Examples of such a group include the following groups.

For example, there can be mentioned 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; -CH ₂ CH ₂ OCH ₂ CH ₃ , -CH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ , -(CH ₂ CH ₂ O) ₂ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₃ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₄ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₅ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₆ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₇ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₈ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₉ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₀ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₁ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₃ CH ₃ , -CH ₂ CH ₂ OH, -(CH ₂ CH ₂ O) ₂ H, -(CH ₂ CH ₂ O) ₃ H, -(CH ₂ CH ₂ O) ₄ H, -(CH ₂ CH ₂ O) ₅ H, -(CH ₂ CH ₂ O) ₆ H, -(CH ₂ CH ₂ O) ₇ H, -(CH ₂ CH ₂ O) ₈ H, -(CH ₂ CH ₂ O) ₉ H, -(CH ₂ CH ₂ O) ₁₀ H, -(CH ₂ CH ₂ O) ₁₁ H, -(CH ₂ CH ₂ O) ₁₂ H, -(CH ₂ CH ₂ O) ₁₃ H, -CH ₂ CH ₂ OCH ₃ , -(CH ₂ CH ₂ O) ₂ CH ₃ , -(CH ₂ CH ₂ O) ₃ CH ₃ , -(CH ₂ CH ₂ O) ₄ CH ₃ , -(CH ₂ CH ₂ O) ₅ CH ₃ , -(CH ₂ CH ₂ O) ₆ CH ₃ , -(CH ₂ CH ₂ O) ₇ CH ₃ , -(CH ₂ CH ₂ O) ₈ CH ₃ , -(CH ₂ CH ₂ O) ₉ CH ₃ , -(CH ₂ CH ₂ O) ₁₀ CH ₃ , -(CH ₂ CH ₂ O) ₁₁ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₃ CH ₃ , and an alkyl group having a substituent such as a group in which -CH ₂ - of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is replaced by -O- (hereinafter, these may be referred to as groups of group A).

For example, there can be listed: 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, 2-aminoanthraquinone and other aromatic groups having substituents (hereinafter, these may be referred to as groups of group B).

For example, there can be mentioned: formyl, acetyl, propionyl, butyryl, 2,2-dimethylpropionyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heneicosyl, benzoyl,

and a carbonyl group bonded to the group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, preferably a carbonyl group bonded to a alkyl group having 1 to 30 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, and more preferably a carbonyl group bonded to a alkyl group having 1 to 20 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group. Preferably, it is a carbonyl group of a preferred 1-valent alkyl group or a monovalent heterocyclic group, and more preferably, it is a carbonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred 1-valent alkyl group or a monovalent heterocyclic group, and more preferably, it is a carbonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred 1-valent alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, t-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethylhexyl)oxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl,

and an oxycarbonyl group bonded to the group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, preferably an oxycarbonyl group bonded to a alkyl group having 1 to 30 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, and more preferably an oxycarbonyl group bonded to a alkyl group having 1 to 20 carbon atoms, a group A to group B or the monovalent An oxycarbonyl group of a preferred alkyl group or a monovalent heterocyclic group, further preferably an oxycarbonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred alkyl group or a monovalent heterocyclic group, and particularly preferably an oxycarbonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, the following can be cited: formyloxy, acetyloxy, propionyloxy, butyryloxy, (2,2-dimethylpropionyl)oxy, pentyloxy, hexyloxy, (2-ethylhexyl)oxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, heneicosyloxy, benzyloxy, vinylcarbonyloxy, (2-propenyl)carbonyloxy, (1-methylvinyl)carbonyloxy, and carbonyloxy groups bonded to the above-mentioned groups A to B or the above-mentioned monovalent alkyl groups or monovalent heterocyclic groups, etc., preferably bonded to A carbonyloxy group having a carbon number of 1 to 30, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, more preferably a carbonyloxy group bonded to a carbon number of 1 to 20, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, further preferably a carbonyloxy group bonded to a carbon number of 1 to 18, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, and particularly preferably a carbonyloxy group bonded to a carbon number of 1 to 12, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group.

For example, there can be mentioned: hydroxyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-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, phenyloxy, benzyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2,6-dimethylphenyloxy, 3,4-dimethylphenyloxy, 3,5-dimethylphenyloxy, 2,3-dicyanophenyloxy, 2,4-dicyanophenyloxy, 2,5-dicyanophenyloxy, 2,6-dicyanophenyloxy, 3,4-dicyanophenyloxy, 3,5-dicyanophenyloxy, 4-methoxyphenyloxy, 2-methoxyphenyloxy, 3-methoxyphenyloxy, 4-ethoxyphenyloxy, 2-ethoxyphenyloxy, 3-ethoxyphenyloxy; trichloromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoro-2-trifluoromethyl-2-methylpropoxy, 2-butoxyethoxy, 2-nitropropoxy, -OCH ₂ CH ₂ OH, -O(CH ₂ CH ₂ O) ₄ H, -OCH _{2 CF 2} CF 2 H, -OCH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ , -OCH ₂ CH ₂ OCH ₂ CH _{3 ,} -O(CH ₂ CH ₂ O) ₂ CH _{2 CH 3} , -O(CH ₂ CH ₂ O) ₄ CH ₂ CH ₃ , -OCH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ ,

and an oxy group bonded to a group of said group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group, etc., preferably an oxy group or a hydroxy group bonded to a alkyl group having 1 to 30 carbon atoms, a group of said group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group, and more preferably a alkyl group having 1 to 20 carbon atoms, a group of said group A to group B or a monovalent hydrocarbon group or a The preferred oxy or hydroxyl group of the monovalent heterocyclic group is further preferably an oxy or hydroxyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred oxy or hydroxyl group of the monovalent alkyl group or monovalent heterocyclic group, and the preferred oxy or hydroxyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred oxy or hydroxyl group of the monovalent alkyl group or monovalent heterocyclic group is particularly preferred.

※Indicates key binding.

For example, there can be mentioned: thio; methylthio, ethylthio, propylthio, butylthio, t-butylthio, pentylthio, hexylthio, (2-ethylhexyl)thio, heptylthio, octylthio, nonylthio, decylthio, undecylthio, dodecylthio, eicosylthio, phenylthio, o-tolylthio,

and a alkyl radical formed by replacing a hydrogen atom with a group of said group A to group B or said monovalent hydrocarbon group or a monovalent heterocyclic group, etc., preferably a alkyl radical formed by replacing a hydrogen atom with a carbon number of 1 to 30, a group of said group A to group B or said monovalent hydrocarbon group or a monovalent heterocyclic group, or a alkyl radical, and more preferably a alkyl radical formed by replacing a hydrogen atom with a carbon number of 1 to 20, a group of said group A to group B or said monovalent hydrocarbon group or a preferred monovalent heterocyclic group, or a alkyl group, further preferably a alkyl group or a alkyl group formed by replacing a hydrogen atom with a carbon number of 1 to 18 alkyl group, a group of the above group A to group B, or a preferred monovalent alkyl group or a monovalent heterocyclic group, or a alkyl group, particularly preferably a alkyl group or a alkyl group formed by replacing a hydrogen atom with a carbon number of 1 to 12 alkyl group, a group of the above group A to group B, or a preferred monovalent alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethylhexyl)sulfonyl, heptylsulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, phenylsulfonyl, p-tolylsulfonyl,

and a sulfonyl group bonded to the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, preferably a sulfonyl group bonded to a alkyl group having 1 to 30 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, and more preferably a sulfonyl group bonded to a alkyl group having 1 to 20 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group. A sulfonyl group of a preferred alkyl group or a monovalent heterocyclic group, further preferably a sulfonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred sulfonyl group of the above monovalent alkyl group or a preferred monovalent heterocyclic group, and particularly preferably a sulfonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred sulfonyl group of the above monovalent alkyl group or a preferred monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned: sulfonylamine; N-methylsulfonylamine, N-ethylsulfonylamine, N-propylsulfonylamine, N-isopropylsulfonylamine, N-butylsulfonylamine, N-isobutylsulfonylamine, N-(sec-butyl)sulfonylamine, N-(tert-butyl)sulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropylsulfonylamine, N-isopropylsulfonylamine, N-butylsulfonylamine, N-isobutylsulfonylamine, N-(sec-butyl)sulfonylamine, N-(tert-butyl)sulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropylsulfonylamine, N-isopropylsulfonylamine, N-(1-butylpropylsulfonylamine, N-isobutylsulfonylamine, N-(tert-butyl)sulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropylsulfonylamine, N-isopropylsulfonylamine, N-(1-butylpropylsulfonylamine, N-isobutylsulfonylamine, N-(tert-butyl)sulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropylsulfonylamine, N-isopropylsulfonylamine, N-isobutylsulfonylamine, N-(tert-butyl) ... 2 NH(CH 2 ) 2 N(CH 2 CH 3 ) 2 、-SO 2 _{NHCH 2 CH} 2 _{CH 2 Si ( OCH 2 CH 3 ) 3} , and an amine sulfonyl group substituted with a group of the group A to group B or one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylamine sulfonyl, N-ethyl-N-methylamine sulfonyl, N,N-diethylamine sulfonyl, N-propyl-N-methylamine sulfonyl, N,N-dipropylamine sulfonyl, N-isopropyl-N-methylamine sulfonyl, N,N-diisopropylamine sulfonyl N,N-diisobutylamine sulfonyl, N,N-di(sec-butyl)amine sulfonyl, N-(tert-butyl)-N-methylamine sulfonyl, N,N-di(tert-butyl)amine sulfonyl, N-butyl-N-methylamine sulfonyl, N,N-dibutylamine sulfonyl, N-butyl-N-octylamine sulfonyl, N,N-dipentylamine sulfonyl, N,N-bis(1-ethylpropyl)amine sulfonyl N-butyl-N-hexylamine sulfonyl, N-hexyl-N-methylamine sulfonyl, N,N-dihexylamine sulfonyl, N-(2-ethylhexyl)-N-methylamine sulfonyl, N,N-bis(2-ethylhexyl)amine sulfonyl, N,N-diheptylamine sulfonyl, N-octyl-N-methylamine sulfonyl, N,N-dioctylamine sulfonyl, N,N-dinonylamine sulfonyl, N -decyl-N-methylsulfonylamine, N-undecyl-N-methylsulfonylamine, N-dodecyl-N-methylsulfonylamine, N-eicosyl-N-methylsulfonylamine, N-phenyl-N-methylsulfonylamine, N,N-diphenylsulfonylamine, and a group selected from Group A to Group B, and an sulfonylamine group in which two of the monovalent hydrocarbon group and the monovalent heterocyclic group are substituted, etc. Preferred are sulfonamide groups substituted with one or two selected from the group consisting of a alkyl group having 1 to 30 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or sulfonamide groups, and more preferred are sulfonamide groups substituted with one or two selected from the group consisting of a alkyl group having 1 to 20 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) 2 ₂ or sulfonamide group, further preferably an sulfonamide group substituted with one or two selected from the group consisting of a alkyl group having 1 to 18 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfonamide group, particularly preferably an sulfonamide group substituted with one or two selected from the group consisting of a alkyl group having 1 to 12 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfonamide group.

For example, there can be enumerated: aminoformyl; N-methylaminoformyl, N-ethylaminoformyl, N-propylaminoformyl, N-isopropylaminoformyl, N-butylaminoformyl, N-isobutylaminoformyl, N-(sec-butyl)aminoformyl, N-(tert-butyl)aminoformyl, N-pentylaminoformyl, N-(1-ethylpropyl)aminoformyl, N-hexylaminoformyl, N-(2-ethylhexyl)aminoformyl, N-heptylaminoformyl, N-octylaminoformyl, N-nonylaminoformyl, N-decylaminoformyl, N-undecylaminoformyl, N-dodecylaminoformyl, N-eicosylaminoformyl, N-phenylaminoformyl, -CONH( _{CH 2} ) ₂ N(CH 2 CH 3 ) ₂ , -CONHCH ₂ CH ₂ CH ₂ Si _{(OCH 2 CH 3} ) ₃ , and aminoformyl groups substituted with the groups A to B or with one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylaminoformyl, N-ethyl-N-methylaminoformyl, N,N-diethylaminoformyl, N-propyl-N-methylaminoformyl, N,N-dipropylaminoformyl, N-isopropyl-N-methylaminoformyl, N,N-diisopropylaminoformyl, N,N-diisobutylaminoformyl, N,N-di(sec-butyl)aminoformyl, N-(t-butyl)-N-methylaminoformyl, N,N-di(t-butyl)aminoformyl, N-butyl-N-methylaminoformyl, aminoformyl, N,N-dibutylaminoformyl, N-butyl-N-octylaminoformyl, N,N-dipentylaminoformyl, N,N-bis(1-ethylpropyl)aminoformyl, N-butyl-N-hexylaminoformyl, N-hexyl-N-methylaminoformyl, N,N-dihexylaminoformyl, N-(2-ethylhexyl)-N-methylaminoformyl, N,N-bis(2-ethylhexyl)aminoformyl, N,N-diheptylaminoformyl, N-octyl-N-methylaminoformyl, N,N-dioctylaminoformyl, N,N-dinonylaminoformyl, N-decyl-N-methylaminoformyl, N-undecyl The present invention is preferably an alkyl-N-methylaminoformyl group, an N-dodecyl-N-methylaminoformyl group, an N-eicosyl-N-methylaminoformyl group, an N-phenyl-N-methylaminoformyl group, an N,N-diphenylaminoformyl group, and an aminoformyl group substituted with two of the groups selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group, and the like, preferably an aminoformyl group substituted with one or two of the groups selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group, or an aminoformyl group, and more preferably an alkyl group selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group. Preferably, the aminoformyl group is substituted with one or two of the groups A to B, the preferred monovalent alkyl group and the preferred monovalent heterocyclic group, or an aminoformyl group; more preferably, the aminoformyl group is substituted with one or two of the groups A to B, the preferred monovalent alkyl group and the preferred monovalent heterocyclic group, or an aminoformyl group; more preferably, the aminoformyl group is substituted with one or two of the groups A to B, the preferred monovalent alkyl group and the preferred monovalent heterocyclic group, or an aminoformyl group; and more preferably, the aminoformyl group is substituted with one or two of the groups A to B, the preferred monovalent alkyl group and the preferred monovalent heterocyclic group, or an aminoformyl group.

For example, the amino groups include: 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 groups substituted with the groups A to B or with one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylamino, N- Ethyl-N-methylamine, N,N-diethylamine, N-propyl-N-methylamine, N,N-dipropylamine, N-isopropyl-N-methylamine, N,N-diisopropylamine, N,N-diisobutylamine, N,N-di(sec-butyl) amine, N-(tert-butyl)-N-methylamine, N,N-di(tert-butyl)amine, N-butyl-N-methylamine, N,N-dibutylamine, N-butyl-N-octylamine, N,N-dipentylamine, N,N-bis(1-ethylpropyl)amine, N-butyl-N-hexylamine, N-hexyl-N-methylamine, N,N-dihexylamine, N-(2-ethylhexyl)-N-methyl amine, N,N-bis(2-ethylhexyl)amine, N,N-diheptylamine, N-octyl-N-methylamine, N,N-dioctylamine, N,N-dinonylamine, N-decyl-N-methylamine, N-undecyl-N-methylamine, N-dodecyl-N-methylamine, N-eicosyl-N-methylamine, N-phenyl-N-methylamine, N,N-diphenylamine, and an amine group substituted with two of the groups A to B, the monovalent alkyl group and the monovalent heterocyclic group, etc., preferably a alkyl group having 1 to 30 carbon atoms, a group of the groups A to B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group. an amine group or an amine group substituted with one or two of the above-mentioned alkyl groups having 1 to 20 carbon atoms, a group of the above-mentioned group A to group B, an amine group or an amine group substituted with one or two of the above-mentioned preferred monovalent alkyl groups and a preferred monovalent heterocyclic group, and further preferably an alkyl group having 1 to 18 carbon atoms, a group of the above-mentioned group A to group B, The amine group or amine group is substituted by one or two of the preferred monovalent hydrocarbon groups and the preferred monovalent heterocyclic groups, and is particularly preferably an amine group or amine group substituted by one or two of the preferred monovalent hydrocarbon groups and the preferred monovalent heterocyclic groups.

For example, there can be enumerated: formylamino, acetylamino, propionylamino, butyrylamino, (2,2-dimethylpropionyl)amino, pentylamino, hexylamino, (2-ethylhexyl)amino, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, heneicosylamino, benzylamino,

and a carbonylamino group bonded to the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, preferably a carbonylamino group bonded to a alkyl group having 1 to 30 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, and more preferably a carbonylamino group bonded to a alkyl group having 1 to 20 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group. Preferably, it is a carbonylamino group that is a preferred carbonyl group or a monovalent heterocyclic group, and more preferably, it is a carbonylamino group that is bonded to a carbonyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred carbonyl group or a monovalent heterocyclic group, and more preferably, it is a carbonylamino group that is bonded to a carbonyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred carbonyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, -SiH ₃ ; -Si(CH ₃ ) ₃ , -Si(CH ₂ CH ₃ ) ₃ , -Si((CH ₂ ) ₂ CH ₃ ) ₃ , -Si(CH(CH ₃ ) ₂ ) ₃ , -Si((CH ₂ ) ₃ CH ₃ ) ₃ , -Si((CH ₂ ) ₄ CH ₃ ) ₃ , -Si((CH ₂ ) ₅ CH ₃ ) ₃ , -Si((CH ₂ ) ₆ CH ₃ ) ₃ , -Si((CH ₂ ) ₇ CH ₃ ) ₃ , -Si((CH ₂ ) ₈ CH ₃ ) ₃ , -Si((CH ₂ ) ₉ CH ₃ ) ₃ , -Si((CH ₂ ) ₁₀ CH ₃ ) ₃ , -Si((CH ₂ ) ₁₁ CH ₃ ) ₃ , -Si((CH ₂ ) ₁₂ CH ₃ ) ₃ , -Si(C ₆ H ₅ ) ₃ , -Si(C ₁₀ H ₇ ) ₃ , -Si(CH ₃ ) ₂ (CH ₂ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₂ CH ₃ ), -Si(CH ₃ ) ₂ (CH(CH ₃ ) ₂ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₃ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₅ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₇ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₉ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₃ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₅ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₉ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₂₉ CH ₃ ), -Si(CH ₃ ) ₂ (C ₆ H ₅ ), -Si(CH ₃ )(C ₆ H ₅ ) ₂ , -Si(CH ₃ ) ₂ (C ₁₀ H ₇ ), and -SiH 3 substituted with one, two or three of the groups selected from Group A to Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group. ₃ , etc.; -Si(OH) ₃ ; -Si(OCH ₃ ) ₃ , -Si(OCH ₂ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₂ CH ₃ ) ₃ , -Si(OCH(CH ₃ ) ₂ ) ₃ , -Si(O(CH ₂ ) ₃ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₄ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₅ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₆ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₇ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₈ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₉ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₁₀ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₁₁ CH ₃ ) ₃ , -Si(OC ₆ H ₅ ) ₃ , -Si(OC ₁₀ H ₇ ) ₃ , -Si(OCH ₃ ) ₂ (OCH ₂ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₂ CH ₃ ), -Si(OCH ₃ ) ₂ (OCH(CH ₃ ) ₂ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₃ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₅ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₇ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₉ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₁ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₃ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₅ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₇ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₉ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₂₉ CH ₃ ), -Si(OCH ₃ ) ₂ (OC ₆ H ₅ ), -Si(OCH ₃ )(OC ₆ H ₅ ) ₂ , -Si(OCH ₃ ) ₂ (OC ₁₀ H ₇ ), and -Si(OH) 3 substituted with one, two or three of the groups selected from the groups A to B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups; -SiH(OH) ₂ ; -Si(CH ₃ )( _{OCH 3} ) ₂ , -Si((CH ₂ ) ₁₁ CH ₃ )(O(CH ₂ ) ₁₁ CH ₃ ) ₂ , -Si(C ₆ H ₅ )(OC ₆ H ₅ ) ₂ , -Si(CH ₃ )(OH) ₂ , -Si((CH ₂ ) ₃₆ CH ₃ )(OH) ₂ , -Si(C ₆ H ₅ )(OH) ₂ , and -SiH(OH) ₂ substituted with one, two or three of the groups selected from Group A to Group B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups; -SiH ₂ (OH); -Si(CH ₃ ) ₂ (OCH ₃ ), -Si((CH ₂ ) ₁₁ CH ₃ ) ₂ (O(CH ₂ ) ₁₁ CH ₃ ), -Si(C ₆ H ₅ ) ₂ (OC ₆ H ₅ ), -Si(CH ₃ ) ₂ (OH), -Si((CH ₂ ) ₁₇ CH ₃ ) ₂ (OH), -Si(C ₆ H ₅ ) ₂ (OH), and -SiH ₂ substituted with one, two or three of the groups selected from Group A to Group B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups; (OH), etc., preferably -SiH 3 , -Si(OH) 3 , -SiH(OH) 2 , -SiH 2 (OH), or -Si(OH) ₃ substituted with one, two or three selected from the group consisting of a alkyl group having 1 to 30 carbon atoms, a group of the above-mentioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, and more preferably -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ , -SiH 2 (OH), or -Si(OH) ₃ substituted with one, two or three selected from the group consisting of a alkyl group having 1 to 20 carbon atoms, a group of the above-mentioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, and more preferably -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ , -SiH ₂ (OH), or -Si(OH) ₃ , further preferably -SiH 3 , -Si(OH) 3 , -SiH(OH) 2 , -SiH 2 (OH), or -Si(OH) _{3 substituted with one, two or three selected from the group consisting of a alkyl group having 1 to 18 carbon atoms, a group of the Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group; particularly preferably -SiH 3 ,} -Si(OH) ₃ , -SiH(OH) ₂ , -SiH ₂ (OH ₎ , or -Si(OH) ₃ substituted with one, two or three selected from the group consisting of a alkyl group having 1 to 12 carbon atoms, a group of the Group A to Group B, a preferred monovalent alkyl group, _and a _preferred monovalent _heterocyclic group.

For example, the o-xylylimidomethyl group (C ₆ H ₄ (CO) ₂ N—CH ₂ —) which may have a substituent can be exemplified, and as the substituent, at least one selected from the group consisting of the halogen atom, the group of Group A to Group B, the monovalent hydrocarbon group, and the monovalent heterocyclic group can be exemplified.

As other bases, we can cite: -SCOCH ₃ ,

wait.

※Indicates key binding.

The monovalent alkyl group or the monovalent heterocyclic group may be substituted by -SO ₃ ^- N ⁺ (C ₁₂ H ₂₅ )(CH ₃ ) ₃ , -CO ₂ ^- N ⁺ (C ₁₂ H ₂₅ )(CH ₃ ) ₃ , -SO ₃ ^- , -CO ₂ ^- or the like.

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

Examples of alkali metal atoms represented by M and MM include alkali metal atoms such as lithium atoms, sodium atoms, and potassium atoms.

As the metal atom which may have a ligand represented by M and MM, metal atoms belonging to Group 2 to Group 15 of the periodic table of elements may be listed. As the metal atom which may have a ligand, Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, Ge are more preferred, and Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr are further preferred, and Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, Cr are particularly preferred.

Examples of N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM include NH ₄ ; a group formed by replacing NH 4 with an alkyl group, such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ ); a group formed by replacing NH ₄ with four alkyl groups, such as N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH _{3 ) 3} ((CH ₂ ) ₁₁ CH _{3 )} , N(CH ₃ ) ₂ ((CH 2 ) ₁₁ CH ₃ ) 2 , and N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 4} substituted; and NH ₄ substituted by one, two, three or four of the groups selected from Group A to Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group.

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 ; a _group in which _NH4 is substituted with an alkyl _group such _{as NH3((CH2)7CH3), NH3((CH2)11CH3 ) , NH3 ( ( CH2 ) 17CH3 )} ; N _{( CH3} ) ₃ ( _{( CH2} ) _15CH3 ), N( _CH3 ) ₃ (( _CH2 ) _11CH3 ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ , etc., which are substituted with NH ₄ by four alkyl groups, and 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; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ) or a group formed by replacing NH ₄ with one alkyl group such as N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , or N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH _{3 ) 2} .

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 ; a group in which _NH4 is substituted with an alkyl _group such _{as NH3} (( _{CH2 ) 7CH3 )} , _NH3 (( _CH2 ) _11CH3 ), NH3((CH2) _17CH3 ); N( _CH3 ) ₃ ( _{( CH2} ) _15CH3 ) _, N( _CH3 ) ₃ (( _CH2 ) _11CH3 ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ , etc., which are preferably: 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; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ) or a group formed by replacing NH ₄ with one alkyl group such as N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , or N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH _{3 ) 2} .

^Q1 and ^Q2 may also independently represent a divalent alkyl group or a divalent heterocyclic group, and -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, _-CH2- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) _2- or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2 M or MM.

^Q1 and ^Q2 are preferably groups represented by formula (QQ1) to formula (QQ19).

[In formula (QQ1) to formula (QQ19), R ^Q1 to R ^Q94 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q1 to R ^Q94 may be bonded to one or more selected from R ^Q1 to R ^Q94 to form a ring; M and MM have the same meanings as described above; ※ indicates a bond]

Regarding the monovalent alkyl group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ^Q1 to R ^Q94 , -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, and -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may also be substituted with a halogen atom, a cyano group, a nitro group, a group of -SO ₃ M, -CO ₂ M or MM, which may be exemplified by R ¹ to R ⁵ and Z ¹ to Z ⁴ , wherein -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group having 1 to 40 carbon atoms may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=, -CH 2 - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) _{2 -} or -CO-, and the hydrogen atom constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, or -SO ₃ M, -CO ₂ M or MM are the same.

Preferred examples of R ^Q1 to R ^Q94 include the same examples as preferred examples of R ¹ to R ⁵ and Z ¹ to Z ⁴ .

^Q1 and ^Q2 are preferably groups represented by formula (QQ1) to (QQ12), more preferably groups represented by formula (QQ1) to (QQ5), further preferably groups represented by formula (QQ1) to (QQ4), particularly preferably groups represented by formula (QQ1) and (QQ2), and further preferably groups represented by formula (QQ2).

As formula (QQ1) to formula (QQ19), for example, the following formulas (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 (Qk22); Formula (Qm1 )~(Qm20);(Qn1)~(Qn16);(Qo1)~(Qo15);(Qp1)~(Qp83);(Qq1)~(Qq72);(Qr1)~(Qr17);(Qs1)~(Qs26);(Qt1)~(Qt26);(Qu1)~(Qu17);(Qv1)~(Qv26);(Qx1)~(Qx2);and(Qy1)~(Qy10) etc. Among them, ※ indicates a bond.

At least one of ^Q1 and ^Q2 is a group represented by formula (QQ20).

[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; L represents a (2p+2q+2)-valent alkyl group or a (2p+2q+2)-valent heterocyclic group, and -C(-)(-)- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted with -Si(-)(-)- to constitute -CH(-)- constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted with -N(-)-, -CH= constituting the (2p+2q+2)-valent alkyl group and the (2p+2q+2)-valent heterocyclic group may be substituted with -N=, and -CH _Q2- may be substituted with -O-, -S-, -S(O) _2- or -CO-, and the hydrogen atom constituting the (2p+2q+2)-valent hydroxyl 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; ^Q3 and Q ⁴ independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q95 to R ^Q104 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q95 ~R ^Q104 may be bonded to one or more selected from R ^Q95 ~R ^Q104 to form a ring; M and MM have the same meanings as described above; ※ represents a bond; when Q ³ , Q ⁴ , R ^Q95 ~R ^Q104 , M and MM exist in plural numbers, they may be the same or different from each other]

In formula (QQ20), p is an integer greater than or equal to 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, further preferably an integer from 0 to 1, q in formula (QQ20) is an integer greater than or equal to 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, further preferably an integer from 0 to 1, and 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, further preferably an integer from 1.

^Q3 and ^Q4 independently represent a divalent alkyl group or a divalent heterocyclic group, and -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, _-CH2- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) _2- or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2 M or MM.

^Q3 and ^Q4 are preferably groups represented by formula (QQ1) to formula (QQ19), more preferably groups represented by formula (QQ1) to formula (QQ12), further preferably groups represented by formula (QQ1) to formula (QQ5), particularly preferably groups represented by formula (QQ1) to formula (QQ4), further preferably groups represented by formula (QQ1) and formula (QQ2), and particularly preferably groups represented by formula (QQ2).

^Q3 and ^Q4 are preferably 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) ~(Qj29);(Qk1)~(Qk22);(Qm1)~(Qm20);(Qn1)~(Qn16);(Qo1)~(Qo15);(Qp1)~(Qp83);(Qq1)~(Qq72);(Qr1)~(Qr17);(Qs1)~(Qs26);(Qt1)~(Qt26);(Qu1)~(Qu17);(Qv1)~(Qv26);(Qx1)~(Qx2);and(Qy1)~(Qy10) etc. wherein ※ denotes a bond.

Regarding the monovalent alkyl group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ^Q95 to R ^Q104 , -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, and -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may also be substituted with a halogen atom, a cyano group, a nitro group, a group of -SO ₃ M, -CO ₂ M or MM, which may be exemplified by R ¹ to R ⁵ and Z ¹ to Z ⁴ , wherein -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group having 1 to 40 carbon atoms may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=, -CH 2 - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) _{2 -} or -CO-, and the hydrogen atom constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, or -SO ₃ M, -CO ₂ M or MM are the same.

Preferred examples of R ^Q95 to R ^Q104 include the same examples as those listed for preferred examples of R ¹ to R ⁵ and Z ¹ to Z ⁴ .

Examples of the group represented by L include groups represented by the following formulae (da1) to (da27); (db1) to (db16); (dc1) to (dc52); (dd1) to (dd68); (de1) to (de86); (df1) to (df3); (dh1) to (dh13); and (dr21), tautomers thereof, 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 of _-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.

Among them, b1~b6 represent key bindings.

As compound (I), for example, compounds represented by formula (Ip) shown in Tables p1 to p22 below or their alkali metal salts can be listed. The compound represented by formula (Ip) may be the same as the compound represented by formula (I), wherein ^Q2 is a group represented by formula (QQ20), and p=0, q=1.

In addition, the symbols recorded in the "Q ^d+1 " column, "Q ^d11 " column, "Q ^d21 " column, and "L ¹ " column in Tables p1 to p22 respectively correspond to the bases represented by the above formulas.

The "Q ^d+1 " column in Tables p1 to p22 indicates that the group represented by Q ^d11 and the group represented by Q ^d21 in the compound represented by formula (Ip) are groups corresponding to the symbols described in the "Q ^d+1 " column.

※ and b1~b4 represent key bindings.

In formula (Ip), C ^b11 , C ^b21 , C ^b31 , and C ^b41 respectively represent carbon atoms that form bonds with L ^1. In the groups represented by formulas (da1) to (da27); (db1) to (db16); (dc1) to (dc52); (dd1) to (dd68); (de1) to (de86); and (dh1) to (dh13), C ^b11 forms a bond with the bond represented by b1, C ^b21 forms a bond with the bond represented by b2, C ^b31 forms a bond with the bond represented by b3, and C ^b41 forms a bond with the bond represented by b4.

^Qd11 and ^Qd21 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group, and may be the same as the divalent hydrocarbon group or divalent heterocyclic group represented by ^Q1 and ^Q2 .

[Table p6]

[Table p7]

[Table p8]

[Table p9]

[Table p10]

[Table p11]

[Table p12]

[Table p13]

[Table p14]

[Table p15]

[Table p16]

[Table p17]

[Table p18]

[Table p19]

[Table p20]

[Table p21]

[Table p22]

In the compound represented by formula (Ip), ^Qd11 and ^Qd21 are each independently preferably a divalent carbon group, more preferably a group represented by formula (QQ1) to formula (QQ7), further preferably a group represented by formula (QQ1) to formula (QQ4), further preferably a group represented by formula (QQ1) or a group represented by formula (QQ2).

^L1 is preferably a group represented by formula (da1) to formula (da27), a group represented by formula (de1) to formula (de86), and more preferably a group represented by formula (da4), a group represented by formula (da16), a group represented by formula (de1), or a group represented by formula (de86).

As compound (I), for example, compounds represented by formula (Iq) shown in the following Table q1 to Table q22 or their alkali metal salts can be listed.

The compound represented by formula (Iq) may be the same as the compound represented by formula (I), wherein ^Q1 is a group represented by formula (QQ20), and p=0 and q=1.

In addition, the symbols recorded in the "Q ^d+2 " column, "Q ^d12 " column, "Q ^d22 " column, and "L ² " column in Tables q1 to q22 respectively correspond to the bases represented by the above formulas.

The "Q ^d+2 " column in Tables q11 to q22 indicates that the group represented by Q ^d12 and the group represented by Q ^d22 in the compound represented by formula (Iq) are groups corresponding to the symbols described in the "Q ^d+2 " column.

※ and b1~b4 represent key bindings.

In formula (Iq), C ^b12 , C ^b22 , C ^b32 , and C ^b42 respectively represent carbon atoms that form bonds with L ^2. In the groups represented by formulas (da1) to (da27); (db1) to (db16); (dc1) to (dc52); (dd1) to (dd68); (de1) to (de86); and (dh1) to (dh13), C ^b12 forms a bond with the bond represented by b1, C ^b22 forms a bond with the bond represented by b2, C ^b32 forms a bond with the bond represented by b3, and C ^b42 forms a bond with the bond represented by b4.

^Qd12 and ^Qd22 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group, and may be the same as the divalent hydrocarbon group or divalent heterocyclic group represented by ^Q1 and ^Q2 .

[Table q1]

[Table q2]

[Table q3]

[Table q4]

[Table q5]

[Table q6]

[Table q7]

[Table q8]

[Table q9]

[Table q10]

[Table q11]

[Table q12]

[Table q13]

[Table q14]

[Table q15]

[Table q16]

[Table q17]

[Table q18]

[Table q19]

[Table q20]

[Table q21]

[Table q22]

As compound (I), for example, compounds represented by formula (Ir) or their alkali metal salts shown in the following Tables r1 to r23 can be cited.

The compound represented by formula (Ir) may be the same as the compound represented by formula (I), wherein ^Q1 is a group represented by formula (QQ20), and p=1 and q=0.

In addition, the symbols recorded in the "Q ^d+3 " column, "Q ^d13 " column, "Q ^d23 " column and "L ³ " column in Table r1 to Table r23 respectively correspond to the groups represented by the above formula and the groups represented by the following formulas (dr1) to (dr22).

The "Q ^d+3 " column in Tables r1 to r23 indicates that the group represented by Q ^d13 and the group represented by Q ^d23 in the compound represented by formula (Ir) are groups corresponding to the symbols described in the "Q ^d+3 " column.

※ and b1~b4 represent key bindings.

In formula (Ir), C ^b13 , C ^b23 , C ^b33 , and C ^b43 respectively represent carbon atoms that form bonds with L ^3. In the groups represented by formulas (da1) to (da27); (db1) to (db16); (dc1) to (dc52); (dd1) to (dd68); (de1) to (de86); (dh1) to (dh13); and (dr1) to (dr22), C ^b13 forms a bond with the bond represented by b1, C ^b23 forms a bond with the bond represented by b2, C ^b33 forms a bond with the bond represented by b3, and C ^b43 forms a bond with the bond represented by b4.

^Qd13 and ^Qd23 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group, and may be the same as the divalent hydrocarbon group or divalent heterocyclic group represented by ^Q1 and ^Q2 .

[Table r1]

[Table r2]

[Table r3]

[Table r4]

[Table r5]

[Table r6]

[Table r7]

[Table r8]

[Table r9]

[Table r10]

[Table r11]

[Table r12]

[Table r13]

[Table r14]

[Table r15]

[Table r16]

[Table r17]

[Table r18]

[Table r19]

[Table r20]

[Table r21]

[Table r22]

[Table r23]

As compound (I), for example, compounds represented by formula (Iw) shown in the following Table w1 and their alkali metal salts can be listed.

Furthermore, the symbols recorded in the "tu" column, the "Q ¹ " column, and the "Q ² " column in Table w1 correspond to the bases represented by the above formula and the bases represented by the following formulas (tu1) to (tu100), respectively.

In the groups represented by the following formulae (tu1) to (tu100), # represents a bond with ^Q1 , and & represents a bond with ^Q2 .

[Table w1]

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) wherein a substituent selected from -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidomethyl (C ₆ H ₄ (CO) ₂ N-CH ₂ -), -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), a compound containing one or more of fluorine atoms, chlorine atoms and bromine atoms.

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) wherein 1 to 6 groups selected from _{-SO 3} H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH 4 , -SO ₂ NH ₂ , -CONH ₂ , phthalimidomethyl (C ₆ H ₄ (CO) ₂ N-CH ₂ -), -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -N(CH 3 )((CH _{2 ) 11} CH 2 ) are substituted. ₃ ) Compounds containing one or more of fluorine atoms, chlorine atoms and bromine atoms.

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 one or more anions selected from -SO ₃ ^- and -CO ₂ ^- , and a radical 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 ²⁺ , and the like. ⁺ and K ⁺ metal salts with more than one cation.

As compound (I), 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) are substituted with -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidomethyl (C ₆ H ₄ (CO) ₂ N-CH ₂ -), -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), a compound containing at least one 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 at least one anion selected from -SO ₃ ^- and -CO ₂ ^- , and a 2+ ion selected from Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn The metal salt of one or more cations selected from the group consisting of Fe 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 ⁺ is more preferably: a compound represented by formula (Ip1) to formula (Ip3198); a compound represented by formula (Ip3997) to formula (Ip5253) and 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 (Ir348 6); 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), The compounds represented by formula (Iq3997) to formula (Iq5253), the compounds represented by formula (Ir1) to formula (Ir3486), the compounds represented by formula (Ir4305) to formula (Ir5563), and the compounds represented by formula (Iw1) to formula (Iw200) are substituted with -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , fluorine atom, chlorine atom and bromine atom, and further preferably: a compound represented by formula (Ip1) to formula (Ip3198); a compound represented by formula (Ip3997) to formula (Ip5253) and 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); a compound represented by formula (Iw1) to formula (Iw200 )； In the compounds represented by formula (Ip1) to (Ip3198), the compounds represented by formula (Ip3997) to (Ip5253), the compounds represented by formula (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), and the compounds represented by formula (Iw1) to (Iw200), a substituted The compound containing one or more of ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a chlorine atom and a bromine atom is particularly preferably: a compound represented by formula (Ip1) to (Ip3198); a compound represented by formula (Ip3997) to (Ip5253) and (Ip6000); a compound represented by formula (Iq1) to (Iq3198); a compound represented by formula (Iq3997) to (Iq5253); a compound represented by formula (Ir1) to (Ir3486); a compound represented by formula (Ir4305) to (Ir5563); and a compound represented by formula (Iw1) to (Iw200).

Compound (I) may be a compound represented by formula (Ip), a compound represented by formula (Iq), a compound represented by formula (Ir), a compound represented by formula (Iw), a compound represented by formula (Ip), and more preferably a compound represented by formula (Ip1) to formula (Ip3198); and a compound represented by formula (Ip3997) to formula (Ip5253), and formula (Ip6000), and the best is a compound represented by formula (Ip4), a compound represented by formula (Ip16), a compound represented by formula (Ip164), a compound represented by formula (Ip412), a compound represented by formula (Ip1156), and a compound represented by formula (Ip6000).

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.

Regarding the compound represented by formula (IM1), a compound represented by formula (pt1) is reacted 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)).

In formula (pt1), formula (pt2), formula (I') and formula (IM1), R ¹ to R ⁵ and Q ¹ have the same meanings as described above.

In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is generally 0.1 mol to 60 mol, preferably 1 mol to 40 mol, more preferably 1 mol to 32 mol, and even more preferably 2 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt1).

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

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

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

Examples of the solvent in the reaction between the compound represented by formula (pt1) and 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; acetone, methyl Ketone solvents such as 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), decahydronaphthalene, and tetrahydronaphthalene; 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; N,N- Amine solvents such as dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl sulfoxide ... amide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

The amount of the solvent used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt1).

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

As the acid in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), there can be listed: inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

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

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

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

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 that is difficult to dissolve compound (I') in the reaction mixture but is easy to dissolve compounds other than compound (I'), and after sufficient mixing, the mixture is filtered to remove compound (I'). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I'). Furthermore, column chromatography and/or recrystallization can also be used for purification.

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.

After the reaction is completed, the reaction mixture is added to a solvent such as methanol that is difficult to dissolve the compound (I') in the reaction mixture but is easy to dissolve compounds other than the compound (I'), and after sufficient mixing, the compound (I') is filtered to remove it. Furthermore, column chromatography and/or recrystallization can also be used for purification.

Examples of the base used 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, sodium methoxide, sodium ethoxide, sodium tert-butoxide, Metal alkoxides such as potassium tert-butylate, organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium, inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide, etc., preferably inorganic bases, more preferably lithium hydroxide, sodium hydroxide and potassium hydroxide, further preferably sodium hydroxide and potassium hydroxide, and particularly preferably potassium hydroxide.

The amount of alkali used in the hydrolysis reaction of the compound represented by formula (I') in the presence of alkali is generally 0.1 mol to 100 mol, preferably 1 mol to 70 mol, and more preferably 2 mol to 40 mol, relative to 1 mol of the compound represented by formula (I').

The amount of water used in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and even more preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (I').

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

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

The method for extracting the compound represented by formula (IM1) from the reaction mixture in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is not particularly limited, and the compound can be extracted by various known methods.

For example, after the reaction is completed, an acidic aqueous solution such as hydrochloric acid is added to the reaction mixture to neutralize it, and then filtered to remove the compound (IM1). Furthermore, the obtained 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, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid to remove the compound (IM1). Furthermore, column chromatography and/or recrystallization can also be used for purification.

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.

After the reaction is completed, an acidic aqueous solution such as hydrochloric acid is added to the reaction mixture for neutralization, and then filtered to remove the compound (IM1). Further, the compound is purified by column chromatography and/or recrystallization.

Regarding the compound represented by formula (IM2), the compound represented by formula (pt1) and the compound represented by formula (pt3) can be reacted to produce the compound represented by formula (IM2) (hereinafter, sometimes referred to as compound (IM2)).

In formula (pt1), formula (pt3) and formula (IM2), R ¹ to R ⁵ and Q ² have the same meanings as described above.

In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 mol to 10 mol, preferably 0.1 mol to 5 mol, more preferably 0.5 mol to 2 mol, and even more preferably 0.8 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (pt1).

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

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

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

As the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3), 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; acetone, methyl isobutyl ketone, etc. Ketone solvents such as ethyl acetate and methyl benzoate; ester solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; 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; N,N-dimethylformamide, N, Amine solvents such as N-dimethylacetamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfoxide, more preferably phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, more preferably phenol, methyl benzoate, and particularly preferably phenol.

The amount of the solvent used in the reaction between 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 even more preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (pt1).

The method for extracting the compound (IM2) from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and the compound (IM2) can be extracted by various known methods.

For example, after the reaction is completed, a solvent such as methanol that is difficult to dissolve the compound (IM2) in the reaction mixture but is easy to dissolve compounds other than the compound (IM2) is added to the reaction mixture, and after sufficient mixing, the mixture is filtered to remove the compound (IM2).

Furthermore, the obtained residue is 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, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid, to remove the compound (IM2).

Furthermore, it can also be 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.

After the reaction is completed, the reaction mixture is added to a solvent such as methanol that is difficult to dissolve the compound (IM2) in the reaction mixture but is easy to dissolve compounds other than the compound (IM2), and after sufficient mixing, the compound (IM2) is filtered to remove the compound (IM2). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Among the compounds represented by formula (I), where ^Q2 is a group represented by formula (QQ20), the compound represented by formula (IQQ20-1) 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).

In formula (pt-L), formula (IMI), formula (IM3), formula (IM4) and formula (IQQ20-1), L, Q ¹ , Q ³ , Q ⁴ , R ¹ to R ⁵ , R ^Q95 to R ^Q104 , p and q have the same meanings as described above.

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

As compounds that can become L (for example, compounds represented by formula (pt-L)), the following compounds can be specifically listed.

L is equivalent to the structure after removing -C(=O)-O-C(=O)- from each of the above compounds.

The compound represented by formula (IM3) can be prepared in the same manner as the compound represented by formula (IM1).

The compound represented by formula (IM4) can be prepared in the same manner as the compound represented by formula (IM2).

The usage amount of the compound represented by formula (pt-L) is generally 0.001 mol to 10 mol, preferably 0.005 mol to 5 mol, more preferably 0.01 mol to 2 mol, and even more preferably 0.1 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (IM1).

When p is not 0, the amount of the compound represented by formula (IM3) used is generally 0.01 mol to 100 mol, preferably 0.05 mol to 20 mol, and more preferably 0.1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM1).

When q is not 0, the amount of the compound represented by formula (IM4) used is generally 0.01 mol to 100 mol, preferably 0.05 mol to 20 mol, and more preferably 0.1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM1).

Regarding the usage amount of the compound represented by formula (IM3) and the usage amount of the compound represented by formula (IM4), it is preferred that the compound represented by formula (IM3) is p moles and the compound represented by formula (IM4) is q moles relative to 1 mole of the compound represented by formula (IM1).

The reaction temperature is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

The reaction time is usually 0.5 hours to 500 hours.

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.

As the solvent, there can be mentioned: 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as oxane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N-dimethylacetyl amine, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, etc., preferably include: diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N- Dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

The amount of the solvent used is usually 1 to 1000 times the total mass of the compound represented by formula (IM1), the compound represented by formula (IM3) and the compound represented by formula (IM4).

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), it is preferred that at least one selected from an acid and a metal salt coexists.

As the acid, there can be listed: 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, etc.; 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acids, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

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 even more preferably 1 to 30 times the total mole.

Examples of metal salts include zinc chloride and aluminum chloride.

The amount of the metal salt used is generally 0.01 to 30 times the total molar amount 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 molar amount, more preferably 0.01 to 10 times the total molar amount, and even more preferably 0.01 to 3 times the total molar amount.

The method for removing the compound represented by formula (IQQ20-1) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

For example, after the reaction is completed, a solvent such as methanol, which is difficult to dissolve in the reaction mixture but is easy to dissolve compounds other than compound (IQQ20-1), is mixed thoroughly with the reaction mixture and filtered to remove compound (IQQ20-1). Furthermore, the obtained 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, 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 water, a low-boiling alcohol such as methanol, or a mixed solvent thereof to remove compound (IQQ20-1). Furthermore, it can also be 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. After the reaction is completed, the reaction mixture may be purified by column chromatography and/or recrystallization.

After the reaction is completed, a solvent such as methanol that is difficult to dissolve in the reaction mixture but is easy to dissolve compounds other than compound (IQQ20-1) is mixed with the reaction mixture and filtered to remove compound (IQQ20-1). Furthermore, column chromatography and/or recrystallization can be used for purification.

Among the compounds represented by formula (I), in which ^Q1 is a group represented by formula (QQ20), a compound represented by formula (IQQ20-2) 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).

In formula (pt-L), formula (IM2), formula (IM3), formula (IM4) and formula (IQQ20-2), L, Q ² , Q ³ , Q ⁴ , R ¹ to R ⁵ , R ^Q95 to R ^Q104 , p and q have the same meanings as described above.

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

The amount of the compound represented by formula (pt-L) used is generally 0.001 mol to 10 mol, preferably 0.005 mol to 5 mol, more preferably 0.01 mol to 2 mol, and even more preferably 0.1 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (IM2).

When p is not 0, the amount of the compound represented by formula (IM3) used is generally 0.01 mol to 100 mol, preferably 0.05 mol to 20 mol, and more preferably 0.1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM2).

When q is not 0, the amount of the compound represented by formula (IM4) used is generally 0.01 mol to 100 mol, preferably 0.05 mol to 20 mol, and more preferably 0.1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM2).

Regarding the usage amount of the compound represented by formula (IM3) and the usage amount of the compound represented by formula (IM4), it is preferred that the compound represented by formula (IM3) is p moles and the compound represented by formula (IM4) is q moles relative to 1 mole of the compound represented by formula (IM2).

The reaction temperature is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

The reaction time is usually 0.5 hours to 500 hours.

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.

As the solvent, there can be mentioned: 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as oxane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N-dimethylacetamide , N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, etc., preferably include: diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-di Methylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

The amount of the solvent used is usually 1 to 1000 times the total mass of the compound represented by formula (IM2), the compound represented by formula (IM3) and the compound represented by formula (IM4).

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), it is preferred that at least one selected from an acid and a metal salt coexists.

As the acid, there can be listed: 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, etc.; 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acids, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

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 even more preferably 1 to 30 times the total mole.

Examples of metal salts include zinc chloride and aluminum chloride.

The amount of the metal salt used is generally 0.01 to 30 times the total molar amount 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 molar amount, more preferably 0.01 to 10 times the total molar amount, and even more preferably 0.01 to 3 times the total molar amount.

The method for removing the compound represented by formula (IQQ20-2) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

For example, after the reaction is completed, a solvent such as methanol, which is difficult to dissolve in the reaction mixture but is easy to dissolve compounds other than compound (IQQ20-2), is mixed with the reaction mixture and filtered to remove compound (IQQ20-2). Furthermore, the obtained 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, 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 water, a low-boiling alcohol such as methanol, or a mixed solvent thereof to remove compound (IQQ20-2). Furthermore, it can also be 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.

After the reaction is completed, a solvent such as methanol that is difficult to dissolve in the reaction mixture but is easy to dissolve compounds other than compound (IQQ20-2) is mixed with the reaction mixture and filtered to remove compound (IQQ20-2). Furthermore, column chromatography and/or recrystallization can be used for purification.

Among the compounds represented by formula (I), where ^Q1 and ^Q2 are groups represented by formula (QQ20), the compound represented by formula (IQQ20-3) 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).

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

[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 described 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; when L, Q ³ , Q ⁴ , R ^Q95 ~R ^Q104 , M and MM exist in plural numbers, they may be the same or different from each other]

p' in formula (IQQ20-3) is an integer greater than or equal to 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, further preferably an integer from 0 to 1, q' in formula (IQQ20-3) is an integer greater than or equal to 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, further preferably an integer from 0 to 1, the sum of p' and q' in 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, further preferably an integer from 1.

The usage amount of the compound represented by formula (pt-L) is generally 0.001 mol to 20 mol, preferably 0.005 mol to 10 mol, more preferably 0.01 mol to 4 mol, and even more preferably 0.1 mol to 3 mol, relative to 1 mol of the compound represented by formula (pt1).

When p or p' is not 0, the amount of the compound represented by formula (IM3) used is generally 0.01 mol to 200 mol, preferably 0.05 mol to 40 mol, and more preferably 0.1 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt1).

When q or q' is not 0, the amount of the compound represented by formula (IM4) used is generally 0.01 mol to 200 mol, preferably 0.05 mol to 40 mol, and more preferably 0.1 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt1).

Regarding the usage amount of the compound represented by formula (IM3) and the usage amount of the compound represented by formula (IM4), it is preferred that the compound represented by formula (IM3) is (p+p') moles and the compound represented by formula (IM4) is (q+q') moles per 1 mole of the compound represented by formula (pt1).

The reaction temperature is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

The reaction time is usually 0.5 hours to 500 hours.

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.

As the solvent, there can be mentioned: 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as oxane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N-dimethylacetamide , N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, etc., preferably: diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N- Dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

The amount of solvent used is usually 1 to 1000 times the total mass of the compound represented by formula (pt1), the compound represented by formula (IM3) and the compound represented by formula (IM4).

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), it is preferred that at least one selected from an acid and a metal salt coexists.

As the acid, there can be listed: 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, etc.; 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acids, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

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 even more preferably 1 to 30 times the total mole.

Examples of metal salts include zinc chloride and aluminum chloride.

The amount of the metal salt used is generally 0.01 to 30 times the total molar amount 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 molar amount, more preferably 0.01 to 10 times the total molar amount, and even more preferably 0.01 to 3 times the total molar amount.

The method for removing the compound represented by formula (IQQ20-3) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

For example, after the reaction is completed, a solvent such as methanol, which is difficult to dissolve in the reaction mixture but is easy to dissolve compounds other than compound (IQQ20-3), is mixed with the reaction mixture and filtered to remove compound (IQQ20-3). Furthermore, the obtained residue can be washed with water, low-boiling alcohol such as methanol, or a mixed solvent thereof, and then washed with water, low-boiling alcohol such as methanol, or a mixed solvent thereof to remove compound (IQQ20-3). Furthermore, it can also be 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.

After the reaction is completed, a solvent such as methanol that is difficult to dissolve in the reaction mixture but easily dissolves compounds other than compound (IQQ20-3) is mixed with the reaction mixture and filtered to remove compound (IQQ20-3). Furthermore, column chromatography and/or recrystallization can be used for purification.

An oligomer or polymer formed by at least one selected from R ¹ to R ⁵ and R ^Q1 to R ^Q104 in each of a plurality of compounds (I) being bonded to each other; an oligomer or polymer formed by at least one selected from R ¹ to R ⁵ and R ^Q1 to R ^Q104 in each of a plurality of compounds (I) being substituted with a bonding bond, and the bonding bonds being bonded to each other via a single bond; and an oligomer or polymer formed by at least one selected from R ¹ to R ⁵ and R ^Q1 to R ^Q104 in each of a plurality of compounds (I) being substituted with a bonding bond, or not being substituted with a bonding bond, and the bonding bond and a group not substituted with the bonding bond being bonded to each other can be prepared by the same reaction as described above.

For example, a compound represented by 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).

Furthermore, the compound (I) of the present invention also includes a compound represented by formula (I ¹¹ ).

In formula (pt11) and formula (I ¹¹ ), R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as described above.

In formula (pt11) and formula (I ¹¹ ), []-TU-[] represents: at least one selected from R ¹ to R ⁵ in [] is bonded to each other; at least one selected from R ¹ to R ⁵ in [] is substituted with a bonding bond, and the bonding bonds are bonded to each other via a single bond; or at least one selected from R ¹ to R ⁵ in [] is substituted with a bonding bond, or is not substituted with a bonding bond, and the bonding bond and a group not substituted with the bonding bond are bonded to each other.

In the reaction of the compound represented by formula (pt11), the compound represented by formula (pt2) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 60 mol, preferably 1 mol to 40 mol, more preferably 1 mol to 32 mol, and even more preferably 2 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt11).

In the reaction of the compound represented by formula (pt11), the compound represented by formula (pt2) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 mol to 60 mol, preferably 1 mol to 40 mol, more preferably 1 mol to 32 mol, and even more preferably 2 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt11).

The reaction temperature is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

The reaction time is usually 0.5 hours to 500 hours.

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.

As the solvent, there can be mentioned: 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as oxane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, Amine solvents such as N-methylpyrrolidone; sulfone solvents such as dimethyl sulfone, preferably: diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-di Methylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably, methyl benzoate.

The amount of the solvent used is usually 1 to 2000 times by mass relative to 1 part by mass of the compound represented by formula (pt11) in the reaction between the compound represented by formula (pt2) and the compound represented by formula (pt3).

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 an acid and a metal salt coexists.

As the acid, there can be listed: 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, etc.; 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acids, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

The amount of the acid used in the reaction of the compound represented by formula (pt11), the compound represented by formula (pt2) and the compound represented by formula (pt3) is usually 1 mol to 180 mol, preferably 1 mol to 140 mol, more preferably 1 mol to 100 mol, and even more preferably 1 mol to 60 mol, relative to 1 mol of the compound represented by formula (pt11).

Examples of metal salts include zinc chloride and aluminum chloride.

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

The method for taking out the compound represented by formula (I ¹¹ ) from the reaction mixture is not particularly limited, and the compound can be taken out by various known methods.

For example, after the reaction is completed, a solvent such as methanol which is difficult to dissolve the compound represented by formula (I ¹¹ ) in the reaction mixture but easily dissolves compounds other than the compound represented by formula (I ¹¹ ) is thoroughly mixed with the reaction mixture and then filtered to remove the compound represented by formula (I ¹¹ ). Furthermore, the obtained 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, 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 water, a low-boiling alcohol such as methanol, or a mixed solvent thereof to remove the compound represented by formula (I ¹¹ ). Furthermore, column chromatography and/or recrystallization can also be used for purification.

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. After the reaction is completed, the reaction mixture may be purified by column chromatography and/or recrystallization.

After the reaction is completed, a solvent such as methanol which is difficult to dissolve the compound represented by formula (I ¹¹ ) in the reaction mixture but is easy to dissolve compounds other than the compound represented by formula (I ¹¹ ) is mixed thoroughly with the reaction mixture and then filtered to remove the compound represented by formula (I ¹¹ ). Furthermore, purification can also be performed by column chromatography and/or recrystallization.

By reacting Compound (I) with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid, a sulfonic group or -SO ₃ M can be introduced into Compound (I).

Compounds obtained by introducing a sulfo group or -SO ₃ M into compound (I) are included in the compounds of the present invention.

The amount of SO ₃ used in the fuming sulfuric acid is generally 1 mol to 200 mol, preferably 2 mol to 150 mol, more preferably 3 mol to 100 mol, and even more preferably 5 mol to 80 mol, relative to 1 mol of compound (I).

The amount of SO ₃ in fuming sulfuric acid is generally 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.

The amount of chlorosulfonic acid used is generally 1 mol to 500 mol, preferably 1 mol to 300 mol, more preferably 1 mol to 200 mol, and even more preferably 1 mol to 150 mol, relative to 1 mol of compound (I).

When chlorosulfonic acid is used to introduce a sulfonic group or -SO ₃ M 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.

The amount of the solvent used is usually 1 to 1000 parts by mass relative to 1 part by mass of compound (I).

The reaction temperature of sulfonation is usually -20℃~200℃, preferably -10℃~150℃, and more preferably 0℃~100℃. The reaction time is usually 0.5 hours~300 hours.

The method for taking out the compound obtained by introducing a sulfonic group or -SO ₃ M into compound (I) from the reaction mixture is not particularly limited, and the compound can be taken out by various known methods.

For example, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is filtered to remove the compound (I) in which the sulfonic group or -SO ₃ M is introduced.

Furthermore, it can also be purified by column chromatography and/or recrystallization.

Alternatively, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is mixed with a hydrophilic organic solvent such as methanol or other alcohol solvents, acetonitrile or other nitrile solvents, or mixed solvents thereof, which are capable of dissolving compounds other than the compound (I) having a sulfonic group or -SO ₃ M introduced therein, although the compound (I) having a sulfonic group or -SO ₃ M introduced therein may be difficult to dissolve, and the mixture is filtered to remove the compound (I) having a sulfonic group or -SO ₃ M introduced therein. Furthermore, purification can be performed by column chromatography and/or recrystallization or the like.

Alternatively, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is neutralized with an aqueous solution of ammonia, a water-soluble amine or a mixture thereof, and then the mixture is 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, and filtered. The solvent of the obtained filtrate is distilled off to remove the compound (I) having a sulfonic group or -SO ₃ M introduced therein. Furthermore, purification can be performed by column chromatography and/or recrystallization.

The compound (I) having -SO ₃ H and/or -CO ₂ H can be reacted with a salt having MM to produce the compound (I) having -SO ₃ (MM) and/or -CO ₂ (MM).

The amount of the salt having MM used is generally 0.01 mol to 100 mol, preferably 0.02 mol to 50 mol, and more preferably 0.1 mol to 30 mol, based on ₁ mol of the compound (I) having -SO ₃ H and/or -CO 2 H.

The reaction temperature is usually 0℃~100℃, preferably 0℃~80℃, more preferably 0℃~60℃, and even more preferably 0℃~40℃.

The reaction time is usually 0.5 hours to 500 hours.

The reaction of the compound (I) having -SO ₃ H and/or -CO ₂ H with 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; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trimethylbenzene), and decahydronaphthalene; For example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrified hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, etc., preferably: water; acetonitrile and other nitrile solvents; methanol, ethanol, 1-propanol, 2-propanol and other alcohol solvents; tetrahydrofuran and other ether solvents; acetone and other ketone solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents; and mixed solvents thereof, preferably water.

The amount of the solvent used is generally 1 to 1000 parts by mass, preferably 10 to 500 parts by mass, and more preferably 20 to 300 parts by mass, based on 1 part _by mass of the compound (I) having -SO ₃ H and/or -CO 2 H.

The reaction of the compound (I) having -SO ₃ H and/or -CO ₂ H with the salt having MM can be carried out in the presence of a base.

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, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and methyl methoxide. Organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium, inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide, etc., preferably inorganic bases, more preferably lithium hydroxide, sodium hydroxide and potassium hydroxide, further preferably sodium hydroxide and potassium hydroxide, and particularly preferably sodium hydroxide.

The amount of the base used is generally 1 mol to 100 mol, preferably 1 mol to 50 mol, more preferably 1 mol to 20 mol, and even more preferably 1 mol to 10 mol, based on ₁ mol _of the compound (I) having -SO 3 H and/or -CO 2 H.

The method for removing the compound (I) having -SO ₃ (MM) and/or -CO ₂ (MM) from the reaction mixture is not particularly limited, and the compound can be removed by various known methods.

For example, after the reaction is completed, the reaction mixture is filtered to remove the compound (I) having -SO ₃ (MM) and/or -CO ₂ (MM). Furthermore, the obtained 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 and purified with water, a low-boiling alcohol such as methanol, or a mixed solvent thereof.

[Coloring composition]

The coloring composition of the present invention comprises compound (I) and resin (B). According to the coloring composition of the present invention, a color filter with a darker color can be formed compared to a coloring composition comprising C.I. Pigment Yellow 138. The color filter formed by the coloring composition of the present invention can be suitably 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.

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

In this specification, the so-called "total amount of solid components" refers to the total amount of components after removing the solvent (E) from the coloring composition of the present invention. The total amount of solid components and the content of each component relative to it can be measured using known analytical methods such as liquid chromatography or gas chromatography.

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

[Solvent (E)]

The solvent (E) is not particularly limited, and any solvent commonly used in this field can be used.

Examples of solvents (E) include: ester solvents (solvents containing -CO-O- and no -O- in the molecule), ether solvents (solvents containing -O- and no -CO-O- in the molecule), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- and no -CO-O- in the molecule), alcohol solvents (solvents containing OH and no -O-, -CO- and -CO-O- in the molecule), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide, etc.

As ester solvents, there can be listed: 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 acetylacetate, ethyl acetylacetate, cyclohexanol acetate and γ-butyrolactone, etc.

As ether solvents, there can be listed: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole, etc.

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.

Ketone solvents include: 4-hydroxy-4-methyl-2-pentanone, acetone, 2- butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone, etc.

As alcohol solvents, there are: methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerol, etc.

As aromatic hydrocarbon solvents, we can cite: benzene, toluene, xylene and mesitylene, etc.

As amide solvents, there are: N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, etc.

Two or more of these solvents may be used in combination.

Among the solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred in terms of coating properties and drying properties. Preferred solvents 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 solvents include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

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

[Resin (B)]

The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from the following monomer (hereinafter referred to as "monomer (a)"), wherein the monomer is at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides.

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

As other structural units, there can be listed structural units derived from monomers copolymerizable with monomer (a) (wherein, different from monomer (a) and monomer (b); hereinafter, there is a case where it is referred to as "monomer (c)"), structural units having ethylenic unsaturated bonds, etc.

In this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. "(meth)acryl" and "(meth)acrylate" also have the same meaning.

Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; maleic acid, fumaric acid, citric 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; Phthalic acid and 1,4-cyclohexene dicarboxylic acid, etc. Unsaturated dicarboxylic acids; 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-methyl unsaturated bicyclic compounds containing a carboxyl group, such as 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; maleic anhydride, conic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5- , unsaturated dicarboxylic anhydrides such as 6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; unsaturated mono[(meth)acryloxyalkyl] esters of polycarboxylic acids having a valence of more than two or more such as mono[2-(meth)acryloxyethyl] succinate and mono[2-(meth)acryloxyethyl] phthalate; unsaturated acrylic esters containing hydroxyl and carboxyl groups in the same molecule such as α-(hydroxymethyl)acrylic acid, etc.

Among these, acrylic acid, methacrylic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, and maleic anhydride are preferred in terms of copolymerization reactivity or solubility of the obtained resin in alkaline aqueous solution.

The 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 the group consisting of an oxycyclopropane ring, an oxycyclobutane ring, and a tetrahydrofuran ring) and an ethylenic unsaturated bond.

The monomer (b) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

Examples of monomer (b) include monomers having an oxocyclopropyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b1)"), monomers having an oxocyclobutyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b2)"), and monomers having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b3)").

As monomer (b1), for example, there can be listed: monomers having a structure formed by epoxidation of aliphatic unsaturated hydrocarbons in a straight chain or branched chain (hereinafter, sometimes referred to as "monomer (b1-1)") and monomers having a structure formed by epoxidation of alicyclic unsaturated hydrocarbons (hereinafter, sometimes referred to as "monomer (b1-2)").

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenic 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-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl) 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.

As monomers (b1-2), for example, vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000; manufactured by Daicel (Co., Ltd.)), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel (Co., Ltd.)), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel (Co., Ltd.)), compounds represented by formula (BI) and compounds represented by formula (BII), etc. can be cited.

[In formula (BI) and formula (BII), ^Ra and ^Rb independently represent 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; ^Xa and ^Xb independently represent a single bond, * ^-Rc- , * ^-Rc- O-, * ^-Rc -S- or *-Rc ^- NH-; ^Rc represents an alkanediyl group having 1 to 6 carbon atoms; * represents a bond with O]

As the alkyl group having 1 to 4 carbon atoms, for example, there can be listed: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.

Examples of alkyl groups formed by replacing a hydrogen atom with a hydroxyl 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, 4-hydroxybutyl, etc.

As ^Ra and ^Rb , preferably, there can be mentioned a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably, there can be mentioned a hydrogen atom and a methyl group.

Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc.

Preferred examples of ^Xa and ^Xb include a single bond, methylene, ethylidene, * _-CH2- O- and * _{-CH2CH2 -} O-. More preferred examples include a single bond and * _{-CH2CH2 -} O- (* represents a bond with O).

As the compound represented by formula (BI), there can be listed compounds represented by any one of formula (BI-1) to formula (BI-15). Among them, preferred are 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), and more preferred are compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).

As the compound represented by formula (BII), there can be listed compounds represented by any one of formula (BII-1) to formula (BII-15), among which preferred are 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 are compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. 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, the 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 even more preferably 20:80 to 80:20 on a molar basis.

As the monomer (b2), a monomer having an oxacyclobutyl group and a (meth)acryloyloxy group is more preferred.

As monomer (b2), for example, 3-methyl-3-methacryloyloxymethyloxycyclobutane, 3-methyl-3-acryloyloxymethyloxycyclobutane, 3-ethyl-3-methacryloyloxymethyloxycyclobutane, 3-ethyl-3-acryloyloxymethyloxycyclobutane, 3-methyl-3-methacryloyloxyethyloxycyclobutane, 3-methyl-3-acryloyloxyethyloxycyclobutane, 3-ethyl-3-methacryloyloxyethyloxycyclobutane, 3-ethyl-3-acryloyloxyethyloxycyclobutane, etc. can be cited.

As the monomer (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred.

Examples of monomers (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

As the monomer (b), the monomer (b1) is preferred in terms of further improving the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, the monomer (b1-2) is more preferred in terms of excellent storage stability of the coloring composition.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-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 ^2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, tricyclo[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 ; (meth)acrylates containing halogen atoms such as 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate; 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] 2-heptene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(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-di(1- Bicyclic unsaturated compounds such as bis(tributoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate and N dicarbonyl imide derivatives such as -(9-acridinyl)maleimide; 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; halides 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.

Among them, preferred are styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-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 ester, 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.

Specific examples of the resin (B) include 3,4-epoxyhexylmethyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/9-vinylcarbazole/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl (meth)acrylate/phenyl (meth)acrylate/o-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/m-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/p-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl (meth)acrylate/2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl ester/(meth)acrylic acid/vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/tricyclo[5.2.1.0 ^2,6 ] decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxycyclobutane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer and resins described in Japanese Patent Laid-Open No. 9-106071, Japanese Patent Laid-Open No. 2004-29518 and Japanese Patent Laid-Open No. 2004-361455, etc.

Among them, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).

The resin (B) may be a combination of two or more types. In this case, the resin (B) is preferably at least a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), more preferably a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1), further preferably a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2), and particularly preferably a copolymer containing a structural unit selected from the group consisting of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

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 3000 to 30000, and particularly preferably 5,000 to 30,000.

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

The acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH/g to 500 mg-KOH/g, more preferably 20 mg-KOH/g to 450 mg-KOH/g, further preferably 20 mg-KOH/g to 400 mg-KOH/g, further more preferably 20 mg-KOH/g to 370 mg-KOH/g, further more preferably 30 mg-KOH/g to 370 mg-KOH/g, further more preferably 30 mg-KOH/g to 350 mg-KOH/g, particularly preferably 30 mg-KOH/g to 340 mg-KOH/g, and most preferably 30 mg-KOH/g to 335 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1g of the resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

In the coloring composition, the content of the resin (B) is less than 100 mass%, preferably 0.00001 mass% or more and 99.99999 mass% or less, more preferably 1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, furthermore, 3 mass% or more and 95 mass% or less, particularly preferably 5 mass% or more and 95 mass% or less, and extremely preferably 10 mass% or more and 95 mass% or less.

[Preparation of liquid containing compound (I)]

The coloring composition of the present invention can be prepared by using a liquid containing compound (I) after pre-preparing a liquid containing compound (I) and a solvent (E). In the case where compound (I) is not dissolved in solvent (E), the liquid containing compound (I) can also be prepared by dispersing compound (I) in solvent (E) and mixing. The liquid containing compound (I) may contain a part or all of the solvent (E) contained in the coloring composition.

The content of the solid component of the liquid containing compound (I) is less than 100 mass%, preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

The content of compound (I) in the liquid containing compound (I) is 100% by mass or less in the total amount of solid components in the liquid containing compound (I), preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 1% by mass or more and 99% by mass or less, particularly preferably 3% by mass or more and 99% by mass or less, further particularly preferably 5% by mass or more and 99% by mass or less.

If necessary, compound (I) may be subjected to rosin treatment, surface treatment using derivatives that introduce acidic or alkaline groups, grafting treatment on the surface of compound (I) using polymer compounds, micronization treatment using sulfuric acid micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, and removal treatment of ionic impurities using ion exchange method, etc.

In addition, compound (I) may be subjected to the following treatments as necessary: crystal structure conversion, particle shaping and/or particle size roughly uniform treatment; mixing compound (I) with water and/or an organic solvent, stirring and/or stirring while heating to obtain a suspension, and filtering the suspension to obtain a compound (I) with a changed crystal structure; changing the crystal structure of compound (I) by recrystallization; ; mixing compound (I) with water, sulfuric acid or an organic solvent, stirring and/or heating while stirring to obtain a solution or suspension, mixing the solution or suspension with a poor solvent for compound (I) to obtain a suspension, filtering the suspension to obtain a compound (I) with a changed crystal structure; mixing compound (I) with a derivative, and water and/or an organic solvent, stirring and/or stirring while heating to obtain a suspension, filtering the suspension to obtain a mixture containing compound (I) with a changed crystal structure and/or mixing compound (I) with a derivative; and recrystallizing the mixture of compound (I) and a derivative to obtain a mixture containing compound (I) with a changed crystal structure and/or mixing compound (I) with a derivative. ; Compound (I), a derivative, and water, sulfuric acid or an organic solvent are mixed, stirred and/or stirred while heating to obtain a solution or suspension, the solution or suspension is mixed with a poor solvent for compound (I), and after obtaining a suspension, 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.

When multiple compounds (I) or derivatives are used, these treatments may be performed individually or in combination.

The particle size of compound (I) is preferably roughly uniform.

As the organic solvent used in the crystal structure transformation, there can be listed: 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as hexane, etc. solvents; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 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.

As the bad solvents, there can be listed: 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, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 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., etc.

As derivatives, there can be listed compounds represented by formula (z) and compounds represented by formula (z1).

When the liquid containing compound (I) contains a derivative, the content of the derivative is 0.01 mass parts or more and 100 mass parts or less, preferably 0.01 mass parts or more and 70 mass parts or less, more preferably 0.1 mass parts or more and 50 mass parts or less, further preferably 0.1 mass parts or more and 30 mass parts or less, and particularly preferably 0.1 mass parts or more and 20 mass parts or less, relative to 100 mass parts of compound (I).

By containing a dispersant and performing a dispersion treatment, compound (I) can be made into a state where compound (I) is uniformly dispersed in a liquid containing compound (I). When using multiple types of compound (I), each can be dispersed individually or multiple types can be mixed and dispersed.

As the dispersant, there can be cited surfactants, which can be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there can be cited polyester-based, polyamine-based and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. Dispersants that are indicated by trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), DISPERBYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.).

When the liquid containing compound (I) contains a dispersant, the amount of the dispersant (solid component) used is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, particularly preferably 0.1 mass parts or more and 300 mass parts or less, further particularly preferably 1 mass parts or more and 300 mass parts or less, and particularly preferably 5 mass parts or more and 260 mass parts or less, relative to 100 mass parts of compound (I).

If the amount of the dispersant used is within the above range, a liquid containing compound (I) in a more uniformly dispersed state tends to be obtained.

When the coloring composition of the present invention includes a resin (B), and a liquid containing compound (I) containing compound (I) and a solvent (E) is prepared in advance and then used to prepare the coloring composition of the present invention, the liquid containing compound (I) may pre-include a part or all of the resin (B) contained in the coloring composition, preferably a part. By pre-including the resin (B), the dispersion stability of the liquid containing compound (I) can be further improved.

When the liquid containing compound (I) contains resin (B), the content of resin (B) is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, and particularly preferably 0.1 mass parts or more and 300 mass parts or less, relative to 100 mass parts of compound (I).

[Polymerizable compound (C)]

The polymerizable compound (C) is a compound that can be polymerized by active free radicals and/or acids generated from the polymerization initiator (D), such as a polymerizable compound having ethylenic unsaturated bonds, etc., preferably a (meth)acrylate compound.

Examples of polymerizable compounds 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 monomer (a), monomer (b), and monomer (c).

Examples of polymerizable compounds having two ethylenic 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.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. Examples of such polymerizable compounds include trihydroxymethylpropane 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)acryl)propene oxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate and caprolactone modified dipentaerythritol hexa(meth)acrylate, etc., preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4000 or less, more preferably 50 or more and 3500 or less, further preferably 50 or more and 3000 or less, particularly preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

In the coloring composition, the content of the polymerizable compound (C) is less than 100 mass%, preferably 0.00001 mass% or more and 99.99999 mass% or less, more preferably 1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, further preferably 1 mass% or more and 90 mass% or less, particularly preferably 2 mass% or more and 80 mass% or less, and extremely preferably 3 mass% or more and 70 mass% or less.

[Polymerization initiator (D)]

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

As polymerization initiators (D), there can be listed: oxime compounds, such as O-acyl oxime compounds, phenyl alkyl ketone compounds, biimidazole compounds, triazine compounds and acyl phosphine oxide compounds, etc.

Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2 -methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, etc. In addition, as the O-acyl oxime compound, commercially available products such as Irgacure OXE01 and OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) can also be used. Among them, as the O-acyl oxime compound, it is preferred to be at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine.

As the alkyl phenone compound, there can be listed: 2-methyl-2-morpholinyl-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinylphenyl)-2-benzylbutane-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1-one. As the alkyl phenone compound, commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

As alkyl phenone compounds, there can also be listed: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-〔4-(2-hydroxyethoxy)phenyl〕propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone and benzyl dimethyl ketal, etc.

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 Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)- 4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with alkoxycarbonyl (carboalkoxy) (for example, see Japanese Patent Publication No. 7-10913, etc.).

As triazine compounds, there can be mentioned: 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, 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.

As the acylphosphine oxide compound, 2,4,6-trimethylbenzyldiphenylphosphine oxide and the like can be cited. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

Furthermore, as the polymerization initiator (D), there can be listed: 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, benzoyl, methyl phenylglyoxylate, and titaniumocene compounds, etc.

These are preferably used in combination with the polymerization initiator described later (hereinafter, sometimes referred to as polymerization initiator (D1)), especially amines.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of phenylalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, oxime compounds and biimidazole compounds, more preferably a polymerization initiator comprising an oxime compound, and further preferably a polymerization initiator comprising an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.001 mass % or more and 60 mass % or less, and more preferably 0.01 mass % or more and 50 mass % or less, relative to the total amount of the resin (B) and the polymerizable compound (C).

[Polymerization initiation aid (D1)]

The coloring composition of the present invention may also contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of the polymerizable compound (C) that starts polymerization by the polymerization initiator (D). When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

Examples of polymerization initiation aids (D1) include amine compounds, alkoxyanthracene compounds, thioanthrone compounds, and carboxylic acid compounds.

As the amine compound, there can be listed: 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, etc., preferably 4,4'-bis(diethylamino)benzophenone. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

As alkoxyanthracene compounds, there are: 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, etc.

As thioxanthrone compounds, there can be listed: 2-isopropylthioxanthrone, 4-isopropylthioxanthrone, 2,4-diethylthioxanthrone, 2,4-dichlorothioxanthrone and 1-chloro-4-propoxythioxanthrone, etc.

As carboxylic acid compounds, there can be listed: phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid, etc.

When these polymerization initiation aids (D1) are used, their content is preferably 0.00001 mass % or more and 60 mass % or less, and more preferably 0.0001 mass % or more and 50 mass % or less relative to the total amount of the resin (B) and the polymerizable compound (C).

[Colorant (A1)]

The coloring composition of the present invention may also contain a coloring agent other than compound (I) (hereinafter, referred to as coloring agent (A1)). The coloring agent (A1) may contain one or more coloring agents. The coloring agent (A1) preferably contains one or more selected from yellow coloring agents, orange coloring agents, red coloring agents and green coloring agents, and more preferably contains one or more selected from yellow coloring agents and green coloring agents.

The coloring agent (A1) may be a dye or a pigment. As the dye, a known dye may be used, for example, the known dyes described in the Color Index (published by The Society of Dyers and Colourists) and the Dyeing Notes (Shikisensha) may be listed. In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, oxyanthracene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azoformine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. may be listed. These dyes may be used alone or in combination of two or more.

Specifically, the dyes with the following color index (C.I.) numbers can be listed.

C.I. solvent yellow (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; C.I. solvent red (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; C.I. solvent orange (solvent yellow): 2 orange)2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. solvent violet (solvent violet)11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. solvent blue (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; C.I. solvent green (solvent C.I. solvent dyes such as green)1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc., C.I. acid yellow (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, 157, 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；C.I. Acid Red (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, 9 4, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 19 5, 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; C.I. acid orange (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; C.I. acid violet (acid violet) 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; C.I. acid blue (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, 8 7, 88, 90, 90: 1, 91, 92, 93, 93: 1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127 、129、130、131、138、140、142、143、147、150、151、154、158、161、166、167、168、170、171、175、182、183、184、187、192、199、203、204、205、210、213、229、234、236、242、243、249、256、259、267、269、278、280、285、290、296、315、324：1、335、340；C.I. Acid Green (acid C.I. acid dyes such as 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, etc., C.I. direct yellow (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; C.I. direct red (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; C.I. direct orange (direct orange)26,34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107; C.I. direct purple (direct violet)47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. direct blue (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 ,106,107,108,109,113,114,115,117,119,120,137,149,150,153,155,156,158,159,160,161,162,163,164,165,166,167,168, 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；C.I.Direct Green (direct C.I. direct dyes such as blue, ... 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; C.I. basic violet (basic violet) 2; C.I. basic red 9; C.I. basic green (basic green) 1 and other C.I. basic dyes, C.I. reactive yellow (reactive yellow) 2, 76, 116; C.I. reactive orange (reactive orange) 16; C.I. reactive red (reactive red) 36 and other C.I. reactive dyes, C.I. mordant yellow (mordant yellow) yellow)5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. mordant red (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; C.I. mordant orange (mordant 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; C.I. mordant 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; C.I. mordant blue 1, 1: 1, 2, 3, 4, 5 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; C.I. mordant green (mordant green) 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes, C.I. vat green (vat green) 1 and other C.I. vat dyes, etc.

Furthermore, Lumogen (registered trademark) as a product of BASF can be listed, including: Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), Lumogen (registered trademark) F Orange 240 (manufactured by BASF) and Lumogen (registered trademark) F Red 305 (manufactured by BASF).

In addition, compounds represented by formula (z) and compounds represented by formula (z1) can be listed.

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

Specific examples include: C.I. 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, 231 and other yellow pigments; C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C.I. Pigment Red 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; C.I. pigment blue (pigment blue) 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments; C.I. pigment violet (pigment violet) 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. pigment green (pigment Green pigments such as C.I. pigment brown (pigment brown) 23, 25, etc.; C.I. pigment black (pigment black) 1, 7, 31, 32, etc.

As the coloring agent (A1), yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow coloring agents"), orange dyes and orange pigments (hereinafter, these may be collectively referred to as "orange coloring agents"), red dyes and red pigments (hereinafter, these may be collectively referred to as "red coloring agents"), green dyes and green pigments (hereinafter, these may be collectively referred to as "green coloring agents") are preferred, yellow coloring agents and green coloring agents are more preferred, yellow pigments and green pigments are further preferred, and green pigments are particularly preferred.

As yellow dyes, dyes whose hue is classified as yellow can be cited, and as yellow pigments, pigments whose hue is classified as yellow can be cited.

As yellow coloring agents, yellow dyes and yellow pigments are preferred, yellow pigments are more preferred, quinophthalone pigments, metal-containing pigments, isoindoline pigments are further preferred, C.I. Pigment Yellow 129, 138, 139, 150, 185, 231 are particularly preferred, and C.I. Pigment Yellow 138, 139, 150, 185, 231 are further preferred.

As orange dyes, dyes whose hue is classified as orange can be cited, and as orange pigments, pigments whose hue is classified as orange can be cited.

As orange coloring agents, orange dyes and orange pigments are preferred, orange pigments are more preferred, and C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 are further preferred.

As red dyes, dyes whose hue is classified as red can be cited, and as red pigments, pigments whose hue is classified as red can be cited.

As the red coloring agent, red dyes and red pigments are preferred, and azo dyes, anthraquinone dyes, triphenylmethane dyes, oxyanthracene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane dyes, oxyanthracene pigments and perylene pigments are more preferred, and C.I. Acid Red 52, C.I. Pigment Red 144, 177, 179, 242, 254 and 269 are further preferred.

In addition, as a yellow colorant, an orange colorant, or a red colorant, an oxyanthracene compound described in Japanese Patent Publication No. 2013-235257 may also be used.

As green dyes, dyes whose hue is classified as green can be cited, and as green pigments, pigments whose hue is classified as green can be cited.

As green colorants, green dyes and green pigments are preferred, green pigments are more preferred, phthalocyanine pigments are further preferred, copper phthalocyanine halides, zinc phthalocyanine halides and aluminum zinc phthalocyanine halides are particularly preferred, and C.I. Pigment Green 7, 36, 58, 59, 62 and 63 are further preferred.

[Preparation of liquid containing coloring agent (A1)]

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

The content of the solid component in the liquid containing the colorant (A1) is less than 100 mass%, preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

The content of the colorant (A1) in the liquid containing the colorant (A1) is 100% by mass or less in the total amount of solid components in the liquid containing the colorant (A1), preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 1% by mass or more and 99% by mass or less, particularly preferably 3% by mass or more and 99% by mass or less, further particularly preferably 5% by mass or more and 99% by mass or less.

The coloring agent (A1) may be subjected to rosin treatment, surface treatment using derivatives with acidic or alkaline groups, grafting treatment on the surface of the coloring agent (A1) using polymer compounds, micronization treatment using sulfuric acid micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, crystal structure transformation similar to compound (I), particle shaping and/or particle size roughly uniform treatment, ionic impurities removal treatment using ion exchange method, etc. The particle size of the coloring agent (A1) is preferably roughly uniform.

The colorant (A1) can be made uniformly dispersed in a liquid containing the colorant (A1) by containing a dispersant and performing a dispersion treatment. The colorant (A1) can be dispersed individually or by mixing multiple types.

As the dispersant, there can be cited surfactants, which can be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there can be cited polyester-based, polyamine-based and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. Dispersants that are indicated by trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), DISPERBYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.).

When the liquid containing the coloring agent (A1) contains a dispersant, the amount of the dispersant (solid component) used is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, particularly preferably 0.1 mass parts or more and 300 mass parts or less, further preferably 1 mass parts or more and 300 mass parts or less, and particularly preferably 5 mass parts or more and 260 mass parts or less, relative to 100 mass parts of the coloring agent (A1).

If the amount of the dispersant used is within the above range, there is a tendency to obtain a liquid containing the colorant (A1) in a more uniformly dispersed state.

In the case where the coloring composition of the present invention includes a resin (B), and a liquid containing a coloring agent (A1) and a solvent (E) is prepared in advance and then used to prepare the coloring composition of the present invention, the liquid containing the coloring agent (A1) may pre-include a part or all of the resin (B) contained in the coloring composition, preferably a part. By pre-including the resin (B), the dispersion stability of the liquid containing the coloring agent (A1) can be further improved.

When the liquid containing the coloring agent (A1) contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 5,000 parts by mass or less, more preferably 0.01 parts by mass or more and 1,000 parts by mass or less, further preferably 0.1 parts by mass or more and 500 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 300 parts by mass or less, relative to 100 parts by mass of the coloring agent (A1).

When the coloring composition of the present invention contains a coloring agent (A1), the content of the coloring agent (A) including the compound (I) and the coloring agent (A1) in the coloring composition is less than 100 mass%, preferably 0.0001 mass% or more and 99.9999 mass% or less, and more preferably 0.0001 mass% or more and 99 mass% or less, relative to the total amount of the solid components. The preferred range is 0.0001 mass% or more and 90 mass% or less, the particularly preferred range is 0.0001 mass% or more and 80 mass% or less, the further preferred range is 0.0001 mass% or more and 70 mass% or less, the particularly preferred range is 0.0001 mass% or more and 60 mass% or less, the extremely preferred range is 0.0001 mass% or more and 55 mass% or less, and the most preferred range is 0.1 mass% or more and 55 mass% or less.

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

[Leveling agent (F)]

As leveling agents (F), silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms can be listed. These may also have polymerizable groups in the side chains.

Examples of silicone-based surfactants include surfactants having siloxane bonds in the molecule. Specifically, they include: 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: Toray Dow Corning) Corning (manufactured by), 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.), etc.

As fluorine-based surfactants, surfactants having fluorine-carbon chains in the molecule can be cited. Specifically, they include: Fluorad (registered trademark) FC430, Fluorad (Fluorad) FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Corporation), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Corporation) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Ltd.), etc.

As silicone-based surfactants having fluorine atoms, surfactants having siloxane bonds and fluorocarbon chains in the molecule can be cited. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (manufactured by DIC Corporation) can be cited.

When a leveling agent (F) is contained, its content is generally 0.00001 mass % or more and 5 mass % or less, preferably 0.00001 mass % or more and 3 mass % or less, more preferably 0.0001 mass % or more and 2 mass % or less, and even more preferably 0.0001 mass % or more and 1 mass % or less, relative to the total amount of the coloring composition.

If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[Antioxidant (G)]

From the perspective of improving the heat resistance and light resistance of the coloring agent, it is better to use antioxidants alone or in combination of two or more. As antioxidants, there is no particular limitation as long as they are antioxidants commonly used in industry, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, etc. can be used.

As the phenolic antioxidant, for example, there can be cited: 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), Irganox 3114 (Irganox 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: thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF), Irganox 1135 (Irganox 1135: Phenylpropionic 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), Adekastab AO-80 (Adekastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxahyspiro(5,5)undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec Co., Ltd.) and Vitamin E (manufactured by Eisai Co., Ltd.), etc.

As the phosphorus-based antioxidant, for example, there can be cited: 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), Adekastab 329K (manufactured by ADEKA), Adekastab PEP36 (manufactured by ADEKA), Adekastab PEP-8 (manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (manufactured by GE), Weston 619G (manufactured by GE), Ultranox 626 (manufactured by 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]dioxophosphin) (manufactured by Sumitomo Chemical Co., Ltd.), etc.

As the sulfur-based antioxidant, for example, there can be listed: dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate or distearyl thiodipropionate, and β-alkyl propionate compounds of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane, etc.

[Other ingredients]

The coloring composition of the present invention may also contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and other additives known in the technical field as needed.

Examples of the adhesion promoter include vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tri(2-methoxyethoxy)silane, 3-glycidyloxypropyl trimethoxysilane, 3-glycidyloxypropyl methyl dimethoxysilane, 3-glycidyloxypropyl methyl diethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-chloropropyl trimethoxysilane, 3-methacryloyloxypropyl trimethoxysilane, 3-butyl propyl trimethoxysilane, 3-thiophene Aminopropyl trimethoxysilane, 3-isocyanate propyl triethoxy silane, N-2-(aminoethyl)-3-aminopropyl methyl dimethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl diethoxysilane, N-2-(aminoethyl)-3-aminopropyl trimethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl diethoxysilane, 3-aminopropyl trimethoxysilane, 3-aminopropyl triethoxysilane, N-phenyl-3-aminopropyl trimethoxysilane and N-phenyl-3-aminopropyl triethoxysilane, etc.

[Method for producing coloring composition]

The coloring composition of the present invention can be prepared, for example, by mixing compound (I), solvent (E), and optionally resin (B), polymerizable compound (C), polymerization initiator (D), polymerization initiator aid (D1), coloring agent (A1), leveling agent (F), antioxidant (G) and/or other components. The mixing can be performed by known or conventional devices or conditions.

Compound (I) is preferably used in the form of a liquid containing compound (I), wherein the liquid containing compound (I) is prepared by mixing compound (I) with a part or all of solvent (E) in advance and dispersing compound (I) using a bead mill or the like until the average particle size of compound (I) is about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) may be prepared as needed.

The colorant (A1) is preferably used in the form of a liquid containing the colorant (A1), wherein the liquid containing the colorant (A1) is prepared by pre-mixing the colorant (A1) with a part or all of the solvent (E), and dispersing the colorant (A1) using a bead mill or the like until the average particle size of the colorant (A1) is about 0.2 μm or less. At this time, a part or all of the dispersant and the resin (B) may be prepared as needed.

The compound (I) is preferably used in the form of a solution (the solution is contained in a liquid containing the compound (I)) which is pre-dissolved in a part or all of the solvent (E). Furthermore, it is preferred to filter the liquid containing the compound (I) using a filter having a pore size of about 0.01 μm or more and about 1 μm or less.

The coloring agent (A1) is preferably used in the form of a solution pre-dissolved in a part or all of the solvent (E) (the solution is contained in the liquid containing the coloring agent (A1)). Furthermore, it is preferred to filter the liquid containing the coloring agent (A1) using a filter with a pore size of about 0.01 μm or more and about 1 μm or less.

It is preferred to filter the mixed coloring composition using a filter with a pore size of about 0.01 μm or more and about 10 μm or less.

[Color filter]

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

The coloring composition is applied on a substrate, volatile components such as solvents are removed and dried to form a coloring film. The coloring film thus formed is included in the color filter of the present invention.

As methods for forming a coloring pattern, photolithography, inkjet, printing, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method of coating the coloring composition on a substrate, drying it to form a coloring composition layer, and exposing and developing the coloring composition layer through a photomask. In photolithography, by not using a photomask during exposure and/or not developing, a coloring coating film that is a cured product of the coloring composition layer can be formed. The coloring pattern or coloring coating film formed in this way is the color filter of the present invention.

The film thickness of the color filter is not particularly limited and can be appropriately adjusted according to the purpose or use, for example, 0.1μm~30μm, preferably 0.1μm~20μm, and more preferably 0.5μm~6μm.

As a substrate, quartz glass, borosilicate glass, alumina silicate glass, sodium calcium glass with silicon dioxide coated on the surface, or resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, and aluminum, silver, silver/copper/palladium alloy thin films formed on the substrate can be used. Other color filter layers, resin layers, transistors, circuits, etc. can also be formed on these substrates.

The formation of pixels of various colors by photolithography can be performed by known or conventional devices or conditions. For example, it can be produced in the following manner.

First, the coloring composition is applied to the substrate, and then volatile components such as solvents are removed and dried by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth coloring composition layer.

As coating methods, there are rotary coating, slit coating, and slit and rotary coating.

The temperature for heating and drying is preferably 30℃~120℃, more preferably 50℃~110℃. In addition, the heating time is preferably 10 seconds~60 minutes, more preferably 30 seconds~30 minutes. When performing reduced pressure drying, it is preferably carried out at a pressure of 50Pa~150Pa and a temperature range of 20℃~25℃. The film thickness of the coloring composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.

Secondly, the coloring composition layer is separated by a photomask for forming a target coloring pattern.

The pattern on the mask is not particularly limited, and a pattern corresponding to the target application can be used. As the light source used in the exposure, it is preferred to be a light source that generates light with a wavelength of 250nm to 450nm. For example, for light less than 350nm, a filter that cuts off the wavelength region can be used to cut off, or for light near 436nm, near 408nm, and near 365nm, a bandpass filter that takes out these wavelength regions can be used to selectively take out. As specific examples of light sources, mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps can be listed.

In order to evenly irradiate the entire exposure surface with parallel light or to accurately align the photomask with the substrate on which the colored component layer is formed, it is better to use an exposure device such as a mask aligner and a stepper.

The exposed coloring composition layer is brought into contact with a developer to form a coloring pattern on the substrate. By developing, the unexposed portion of the coloring composition layer is dissolved in the developer and removed.

As a developer, preferably, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is used.

The concentration of the alkaline compound is preferably 0.01 mass% to 10 mass%, and more preferably 0.02 mass% to 5 mass%. The developer may contain a surfactant.

The developing method can be any of the liquid coating method, immersion method and spray method. Furthermore, during the development, the substrate can be tilted at any angle.

The substrate is preferably washed with water after development.

Furthermore, it is preferred to post-bake the obtained colored pattern.

The post-baking temperature is preferably 150℃~250℃, more preferably 160℃~235℃. The post-baking time is preferably 1 minute~120 minutes, more preferably 10 minutes~60 minutes. The colored pattern or colored coating film obtained in this way, i.e., the color filter, can also be used in surface coating treatment in order to impart various characteristics.

The color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic electroluminescence (EL) devices, electronic paper, etc.) and solid-state imaging elements, and is particularly useful as a color filter used in liquid crystal display devices.

[Implementation example]

The following examples are given to more specifically illustrate the present invention, but the present invention is not limited to the following examples at all, and can of course be implemented with appropriate changes within the scope of the above and the following subject matter, all of which are included in the technical scope of the present invention. Furthermore, below, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

In the following synthesis examples, the structures of the compounds were confirmed by mass analysis (LC (Liquid Chromatography): Model 1200 manufactured by Agilent, MASS: Model LC/MSD6130 manufactured by Agilent).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were determined by gel permeation chromatography (GPC) under the following conditions.

Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40℃

Solvent: Tetrahydrofuran

Flow rate: 1.0mL/min

Solid content concentration of the analytical sample: 0.001 mass%~0.01 mass%

Injection volume: 50μL

Detector: RI

Standard materials for calibration: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

The ratio (Mw/Mn) of the obtained polystyrene-converted weight average molecular weight (Mw) and number average molecular weight (Mn) is defined as the dispersion degree.

Synthesis Example A

Mix 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.).

The mixture was stirred for 10 hours while being maintained at 170°C.

Add 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.) to the mixture.

The mixture was stirred for 9 hours while being maintained at 170°C.

Add 9 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) to the mixture.

The mixture was stirred for 18 hours while being maintained at 170°C.

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.) were added to the mixture.

The mixture was stirred for 27 hours while being maintained at 170°C.

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.) were added to the mixture.

The mixture was stirred for 8 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 2800 parts of methanol were added to the mixture.

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

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

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

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

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

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 417 Exact Mass: 418

Synthesis Example B

Mix 1 mol of the compound represented by formula (Ia1), 20 mol of potassium hydroxide, and a mixture of water 10 times the weight of 1 mol of the compound represented by formula (Ia1).

The mixture was stirred while being maintained at 90°C until the compound represented by formula (Ia1) disappeared.

Neutralize the mixture by mixing it with 36% hydrochloric acid.

The mixture was filtered.

The obtained residue is washed with water.

The residue was purified by column chromatography to obtain the compound represented by formula (IM1-6).

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

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

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 287 Exact Mass: 288

Example D-1

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 methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) in an amount 73 times the weight of 1 mol of the compound represented by formula (IM1-6).

The mixture was stirred for 120 hours while being kept at 170°C. The mixture was cooled to room temperature, and methanol in an amount 13 times the weight of the mixture was added to the mixture. The obtained mixture was stirred at room temperature, filtered, and the obtained residue was washed with methanol.

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

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

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

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 849 Exact Mass: 850

Example D-2

The same method as Example D-1 was followed except that 4,4'-oxydiphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ip4).

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

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

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 983

[Identification of compounds]

The structure of the compound was identified by mass analysis (LCMS (Liquid Chromatography/Mass Spectrometry), LC: 1200 model manufactured by Agilent, MASS: LC/MSD model manufactured by Agilent) and mass analysis (MALDI-TOFMS (Matrix Assisted Laser Desorption Ionization-Time of Flight Mass Spectrometry): JMS-S3000 manufactured by JEOL) .

Synthesis Example C

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, it was cooled to room temperature and poured into 75 parts of methanol. The obtained crystals were filtered and separated. Vacuum drying was performed to obtain 2.0 parts of light orange powder. The obtained powder was mass analyzed by LCMS and confirmed to be the compound represented by formula (IM1-6).

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 289 Exact Mass: 288

Example D-3

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 flask substituted with nitrogen, heated to 220°C, and stirred for 4 hours. After the reaction, it was cooled to room temperature and poured into 80 parts of methanol/50 parts of ion-exchanged water, and the obtained crystals were filtered and separated. The obtained crystals were poured into 50 parts of methanol/40 parts of ion-exchanged 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).

(Quality Analysis)

Ionization mode = MALDI (Positive): m/z = [M+H] ⁺ 851 Exact Mass: 850

Example D-4

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 flask substituted with nitrogen, heated to 220°C, and stirred for 5 hours. After the reaction, it was cooled to room temperature and poured into 80 parts of methanol/50 parts of ion-exchanged water, and the obtained crystals were filtered and separated. Vacuum drying was performed to obtain 1.32 parts of yellow powder. The obtained crystals were repeatedly re-slurried and washed with methanol, and vacuum dried to obtain 0.77 parts of golden powder. The obtained golden yellow powder was mass analyzed by MALDI-TOFMS and confirmed to contain the compound represented by formula (Ip4).

(Quality Analysis)

Ionization mode = MALDI (Positive): m/z = [M+H] ⁺ 985 Exact Mass: 984

Example D-5

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 flask purged with nitrogen, 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 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 mass analyzed by MALDI-TOFMS and confirmed to contain the compound represented by formula (Ip164).

(Quality Analysis)

Ionization mode = MALDI (Positive): m/z = [M+H] ⁺ 759 Exact Mass: 758

Example D-6

1.00 parts of the powder obtained in Synthesis Example C, 0.29 parts of 1,2,4,5-cyclohexanetetracarboxylic acid anhydride, 2.72 parts of benzoic acid, and 4.80 parts of methyl benzoate were placed in a flask substituted with nitrogen, 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 then vacuum dried to obtain 0.79 parts of yellow powder. The obtained yellow powder was mass analyzed using a liquid chromatograph/mass spectrometer, and it was confirmed that it contained the compound represented by formula (Ip6000).

(Quality Analysis)

Ionization mode = ESI (Positive): m/z = [M+H] ⁺ 765 Exact Mass: 764

Synthesis Example A-2

The compound represented by formula (Ia2) was synthesized using the method described in Japanese Patent Publication No. 2020-132878.

Synthesis Example B-2

The compound represented by formula (IM1-7) was synthesized by the same method as in Synthesis Example B except that the compound represented by formula (Ia1) was replaced by the compound represented by formula (Ia2).

Example D-7

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 flask substituted with nitrogen, 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 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 mass analyzed by MALDI-TOFMS and confirmed to contain the compound represented by formula (Ip1156).

(Quality Analysis)

Ionization mode = MALDI (Positive): m/z = [M+H] ⁺ 787 Exact Mass: 786

Synthesis Example A-3

The compound represented by formula (Ia3) was synthesized using the method described in Japanese Patent Publication No. 2020-132878.

Synthesis Example B-3

The compound represented by formula (IM1-8) was synthesized by the same method as in Synthesis Example B except that the compound represented by formula (Ia1) was replaced by the compound represented by formula (Ia3).

Example D-8

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 mass analyzed by MALDI-TOFMS, and it was confirmed that it contained the compound represented by formula (Ip412).

(Quality Analysis)

Ionization mode = MALDI (Positive): m/z = [M+H] ⁺ 859 Exact Mass: 858

Synthesis Example 1

A suitable amount of nitrogen was passed through a flask including a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, and 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) 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) having 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 calculated as solid content was 80 mg-KOH/g.

Synthesis Example 2

A suitable amount of nitrogen was passed through a flask including a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, a mixed solution of 57 parts of acrylic acid, 54 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in molar ratio), 239 parts of benzyl methacrylate and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) 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) having 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 calculated as solid content was 114 mg-KOH/g.

Example E-1

Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition ME-1.

Next, the components are mixed in the following proportions to obtain a coloring composition E-1.

The coloring composition E-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked pigmented coating film was measured in units of 1 nm within the range of 380 nm to 780 nm using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

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

Example E-2

The compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip4) obtained in Example D-2. The same process as Example E-1 was performed to obtain a coloring composition E-2, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

Example E-3

The same process as in Example E-1 was performed except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip164) obtained in Example D-5 to obtain a coloring composition E-3, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

Example E-4

The same process as Example E-1 was performed except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip6000) obtained in Example D-6 to obtain a coloring composition E-4, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

Example E-5

The same process as in Example E-1 was performed except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip1156) obtained in Example D-7 to obtain a coloring composition E-5, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

Example E-6

The same process as in Example E-1 was performed except that the compound represented by formula (Ip16) was replaced by the compound represented by formula (Ip412) obtained in Example D-8 to obtain a coloring composition E-6, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

Comparison Example 1

The compound represented by formula (Ip16) was replaced with C.I. Pigment Yellow 138 (Paliotol Gelb L0962HD manufactured by BASF), and the same method as Example E-1 was followed to obtain a coloring composition E-7, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

According to the results, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating formed by 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 (458nm) on the longest wavelength side of the absorption spectrum of the colored coating formed by the coloring composition containing C.I. Pigment Yellow 138.

[Preparation Example 1~Preparation Example 7]

[Preparation of coloring composition]

By mixing the components in such a way as to form the composition shown in Table AD6, a colored composition can be obtained. The unit of the value is mass part.

In Table AD6, the components are as follows.

Coloring composition E-1: Coloring composition E-1 described in Example E-1

Coloring composition E-2: Coloring composition E-2 described in Example E-2

Coloring composition E-3: Coloring composition E-3 described in Example E-3

Coloring composition E-4: Coloring composition E-4 described in Example E-4

Coloring composition E-5: Coloring composition E-5 described in Example E-5

Coloring composition E-6: Coloring composition E-6 described in Example E-6

Coloring composition E-7: Coloring composition E-7 described in Comparative Example 1

Resin (B): Resin B1 (solid content)

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

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

Solvent (E): Propylene glycol monomethyl ether acetate

Leveling agent (F): Polyether modified silicone oil ("Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.) (solid content)

<Production of color filters (color coatings)>

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 irradiated with light at an exposure dose of 100 mJ/ ^cm2 (365nm reference) in an atmospheric environment using an exposure machine (TME-150RSK; manufactured by Topcon). After light irradiation, it was post-baked at 230°C for 30 minutes in an oven to obtain a coloring film.

[Industrial availability]

The coloring composition and compound of the present invention can be used in the formation of a color filter with a darker color than a coloring composition containing C.I. Pigment Yellow 138, and therefore can be suitably used in a color filter or a display device such as a liquid crystal display device.

Claims (5)

A compound represented by the following formula (Ip):

In formula (Ip), C ^b11 , C ^b21 , C ^b31 , and C ^b41 each represent a carbon atom that forms a bond with L ^1. In the groups represented by formulas (da1) to (da27), (db1) to (db16), (dc1) to (dc52), (dd1) to (dd68), (de1) to (de31), (de33) to (de45), (de47) to (de77), (de84) to (de86), and (dh1) to (dh13), C ^b11 forms a bond with the bond represented by b1, C ^b21 forms a bond with the bond represented by b2, C ^b31 forms a bond with the bond represented by b3, and C ^b41 forms a bond with the bond represented by b4, ^Qd11 and ^Qd21 each independently represent benzene, benzene having a substituent, naphthalene, or naphthalene having a substituent,

A coloring composition comprising the compound as described in claim 1 and a resin. The coloring composition as described in claim 2 comprises a polymerizable compound and a polymerization initiator. A color filter, which is formed by the coloring composition as described in claim 2 or claim 3. A display device comprising a color filter as described in claim 4.