KR20210144834A - Coloring compositions, compounds, color filters and display devices - Google Patents

Abstract

The present invention is a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum on the longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of conventionally known CI Pigment Yellow 138, and/or the longest wavelength of the absorption spectrum It aims at providing the coloring composition containing the compound which has the wavelength of the shoulder peak of the side. This invention relates to the coloring composition containing the compound and solvent represented by Formula (I).

Description

Coloring compositions, compounds, color filters and display devices

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

[0002] The coloring composition is used for production of a color filter used in a display device such as a liquid crystal display device and an electroluminescent display device. As a coloring agent contained in the coloring composition, C.I. Pigment Yellow 138 is known (Patent Document 1).

(C.I. Pigment Yellow 138)

[0003] 1. Japanese Patent Laid-Open No. 2013-82906

[0004] In recent years, development of a display display to widen a displayable color reproduction region is progressing, and as a part of that, a color filter is also required to have a darker color. In order to satisfy the requirement, the conventionally known C.I. A compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum on the longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of Pigment Yellow 138, and/or a shoulder peak on the longest wavelength side of the absorption spectrum The coloring composition containing the compound which has the wavelength of (shoulder peak) is needed.

With the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum mentioned above,

compound,

· C.I. It is a case where it does not have the maximum absorption wavelength of the longest wavelength side of an absorption spectrum on the long wavelength side rather than the maximum absorption wavelength of the longest wavelength side of the absorption spectrum of Pigment Yellow 138,

In addition,

When there are two or more inflection points of the absorption spectrum on the longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum,

It means the wavelength of the average value of the wavelength of the inflection point of the side of the longest wavelength side of an absorption spectrum, and the wavelength of the inflection point of the side of the 2nd longest wavelength side of an absorption spectrum.

[0005] The present invention provides the following [1] to [6].

[1] A coloring composition comprising a compound represented by the following formula (I) and a solvent.

[In formula (I),

R ¹ to ^{R 5} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or Represents a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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 ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ may be respectively 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} each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,

-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

Even if the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.

However, ^{at least one of Q 1} and Q ² has a group represented by the formula (y).

Y ¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

※ indicates a bonding hand (結合手).

When two or more Z ^{1 to Z 4} , the group represented by the formula (y), Y ¹ , M and MM each exist, they may be the same as or different from each other.]

[2] The coloring composition according to [1], comprising a resin.

[3] The coloring composition according to [1] or [2], comprising a polymerizable compound and a polymerization initiator.

[4] A color filter formed of the coloring composition according to any one of [1] to [3].

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

[6] A compound represented by formula (I).

[In formula (I),

R ¹ to ^{R 5} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent hydrocarbon group having 1 to 40 carbon atoms represents a monovalent heterocyclic group,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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 ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ may be respectively 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} each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,

-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

Even if the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.

However, ^{at least one of Q 1} and Q ² has a group represented by the formula (y).

Y ¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

※ indicates a bonding hand.

When two or more Z ^{1 to Z 4} , the group represented by the formula (y), Y ¹ , M and MM each exist, they may be the same as or different from each other.]

[0006] According to the present invention, C.I. Compared with the coloring composition containing Pigment Yellow 138, the coloring composition and compound which can be used for formation of a color filter of a darker color are provided.

[0007] [Coloring composition]

The coloring composition of this invention contains the compound (Hereinafter, it may be called compound (I).) represented by Formula (I), and a solvent (Hereinafter, it may be called solvent (E).).).

[In formula (I),

R ¹ to ^{R 5} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent hydrocarbon group having 1 to 40 carbon atoms represents a monovalent heterocyclic group,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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 ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ may be respectively 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} each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,

-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

Even if the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.

However, ^{at least one of Q 1} and Q ² has a group represented by the formula (y).

Y ¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

※ indicates a bonding hand.

When two or more Z ^{1 to Z 4} , the group represented by the formula (y), Y ¹ , M and MM each exist, they may be the same as or different from each other.]

[0008] Compound (I) also includes tautomers thereof and salts thereof.

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

The coloring composition of this invention may contain the 1 type, or 2 or more types of compound (I).

The coloring composition of this invention may contain resin (Hereinafter, it may call resin (B).).

The coloring composition of this invention may contain the polymeric compound (Hereinafter, it may call a polymeric compound (C).).

The coloring composition of this invention may contain the polymerization initiator (Hereinafter, it may call a polymerization initiator (D).).

The coloring composition of this invention may contain the polymerization initiation adjuvant (Hereinafter, it may be called polymerization initiation adjuvant (D1).).

The coloring composition of the present invention is a coloring agent other than the compound (I) (hereinafter, sometimes referred to as a coloring agent (A1). In the following, the compound (I) and the coloring agent (A1) are collectively referred to as a “colorant (A)”. In some cases.) may be included.

The coloring agent (A1) may contain 1 type, or 2 or more types of coloring agents.

It is preferable that a coloring agent (A1) contains 1 or more types chosen from a yellow coloring agent, an orange coloring agent, a red coloring agent, and a green coloring agent.

The coloring composition of this invention may also contain the leveling agent (Hereinafter, it may call a leveling agent (F).).

The coloring composition of this invention may also contain antioxidant (Hereinafter, it may be called antioxidant (G).).

[0009] [Compound (I)]

Hereinafter, the present invention will be described in more detail by taking the partial structure of compound (I) as an example. Even if not, the following examples include an embodiment in which the substituents are bonded to all sites in the ring structure, respectively. One or two or more substituents may be bonded to the ring structure, and when two or more substituents are bonded to the ring structure, the substituents may be the same or different, respectively.

[0010] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom, a chlorine atom and a bromine atom are preferable.

[0011] ^{The number of carbon atoms in the hydrocarbon group represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably Preferably it is 1-18, More preferably, it is 1-12.

The ^{monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ^{1 may} be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and a chain ( chain hydrocarbon group) or cyclic (alicyclic hydrocarbon group).

[0012] Examples of ^{the saturated or unsaturated chain hydrocarbon group represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. , nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group , tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl group, tritriacontyl group, tetratriacone group straight-chain alkyl groups such as a tyl group, a pentatriacontyl group, a hexatriacontyl group, a heptatriacontyl group, an octatriacontyl group, a nonatriacontyl group, and a tetracontyl group;

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

Ethenyl group (vinyl group), propenyl group (eg 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (eg 1-butenyl group, 2-butene) diyl, 3-butenyl group), 3-methyl-1-butenyl group, 1,3-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,2 -Dimethyl-1-propenyl group, pentenyl group (eg, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group), 1-(1,1-dimethylethyl)ethenyl group, 1, 3-dimethyl-1-butenyl group, hexenyl group (eg 1-hexenyl group, 5-hexenyl group), heptenyl group (eg 1-heptenyl group, 6-heptenyl group), octenyl group (eg 1-octenyl group) , 7-octenyl group), nonenyl group (eg, 1-nonenyl group, 8-nonenyl group), decenyl group (eg, 1-decenyl group, 9-decenyl group), undecenyl group, dodecenyl group, tridecenyl group , tetradesenyl group, pentadesenyl group, hexadesenyl group, heptadesenyl group, octadesenyl group, nonadesenyl group, icosenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group and alkenyl groups such as 1-methyl-1-butenyl group;

ethynyl group, propynyl group (eg 1-propynyl group, 2-propynyl group), octynyl group (eg 1-octynyl group, 7-octynyl group), butynyl group, pentynyl group, hexynyl group, heptynyl group, noninyl group, alkynyl groups such as a decinyl group, an undecinyl group, a dodecinyl group, a tridecinyl group, a tetradecinyl group, a pentadecinyl group, a hexadecinyl group, a heptadecinyl group, an octadecinyl group, a nonadecinyl group and an icosinyl group; and the like.

The saturated chain hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, still more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms.

The carbon number of the unsaturated chain hydrocarbon group is preferably 2 to 30, more preferably 2 to 20, still more preferably 2 to 18, still more preferably 2 to 12.

Especially, it is especially preferable that it is a C1-C12 linear or branched alkyl group.

[0013] Examples of ^{the saturated or unsaturated alicyclic hydrocarbon group represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ include a cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group. Sil group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group Sil group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4 -Dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4, 6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group and 4 - cycloalkyl groups, such as a cyclohexyl cyclohexyl group; Cyclohexenyl group (for example, cyclohexa-1-en-1-yl group, cyclohexa-2-en-1-yl group, cyclohexa-3-en-1-yl group), cycloheptenyl group and cyclooctenyl group alkenyl group; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl; and the like.

The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, and still more preferably 3 to 12 carbon atoms. Among them, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and an adamantyl group are particularly preferable.

[0014] Examples of ^{the aromatic hydrocarbon group represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ include a phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, and 3-ethyl Phenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4 -vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert) -Butyl)phenyl group, 3,5-di(tert-butyl)-4-methylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis(1-methylethyl)phenyl group, 2,4,6- Tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(1,1,3,3-tetramethylbutyl)phenyl group, 1-naphthyl group , 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group aromatic hydrocarbon groups such as , phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, peryleneyl group, chrysenyl group and pyrenyl group; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-18, More preferably, it is 6-12.

The ^{hydrocarbon group represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ is a combination of the hydrocarbon groups exemplified above (eg, at least one of an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group). A benzyl group, (2-methylphenyl)methyl group, (3-methylphenyl)methyl group, (4-methylphenyl)methyl group, (2-ethylphenyl)methyl group, (3-ethylphenyl)methyl group, (4-ethylphenyl) Methyl group, (2-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (4-(tert-butyl)phenyl)methyl group, (3,5-dimethylphenyl)methyl group, 1- aralkyl groups such as phenylethyl group, 1,1-diphenylethyl group, phenethyl group, 1-methyl-1-phenylethyl group, (1-naphthyl)methyl group and (2-naphthyl)methyl group;

arylalkenyl groups such as 1-phenylethenyl group, 2-phenylethenyl group (phenylvinyl group), 2,2-diphenylethenyl group, and 2-phenyl-2-(1-naphthyl)ethenyl group;

phenylethynyl group

[0016]

Aryl alkynyl groups, such as;

a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded;

Cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group

[0017]

and the like.

※ indicates a bonding hand.

The ^{group represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ is a combination of the above-mentioned hydrocarbon groups (eg, a chain hydrocarbon group and an alicyclic hydrocarbon group), for example, a cyclopropylmethyl group, a cyclopropylethyl group , cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, (2-methylcyclohexyl)methyl group, cyclohexylethyl group, may be an alkyl group bonded to one or more alicyclic hydrocarbon groups such as adamantylmethyl group. .

These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 4-20, More preferably, it is 4-18, More preferably, it is 4-12.

[0018] The ^{monovalent heterocyclic group having 1 to 40 carbon atoms represented by R 1} to ^{R 5} , Z ^{1 to Z 4} and Y ¹ represents a group containing a hetero atom as a component of the ring. The monovalent heterocyclic group having 1 to 40 carbon atoms may be monocyclic or polycyclic. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned.

The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, and still more preferably 3 to 12 carbon atoms.

As a heterocyclic ring containing a nitrogen atom,

monocyclic saturated heterocyclic rings such as aziridine, azetidine, pyrrolidine, piperidine and piperazine;

Pyrrole such as pyrrole, 1-methylpyrrole, 2,5-dimethylpyrrole, pyrazole, 1-methylpyrazole, 2-methylpyrazole, 3-methylpyrazole, 4-methylpyrazole, 5-methylpyrazole, etc. 5-membered ring-based unsaturated heterocycles such as pyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole;

pyrimidines such as pyridine, pyridazine, pyrimidine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine;

Quinox such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline condensed bicyclic heterocyclic rings such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperidine;

condensed tricyclic heterocyclic rings such as carbazole, acridine and phenazine; and the like.

As a heterocyclic ring containing an oxygen atom,

monocyclic saturated heterocyclic rings such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxolane, and 2-cyclopentyldioxolane;

bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, and 1,4-dioxaspiro[4.4]nonane;

lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone;

5-membered ring-system unsaturated heterocycles, such as furan, such as furan, 2, 3- dimethyl furan, and 2, 5- dimethyl furan;

6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran;

Benzofuran such as 1-benzofuran; hetero ring;

condensed tricyclic heterocycles such as xanthene and dibenzofuran;

acid anhydride-based heterocycles such as phthalic anhydride; and the like.

As a heterocyclic ring containing a sulfur atom,

5-membered ring-based saturated heterocycles such as dithiolane;

6-membered saturated heterocyclic rings such as thiane, 1,3-dithiane, and 2-methyl-1,3-dithiane;

thiophene such as thiophene, 3-methylthiophene and 2-carboxythiophene, thiopyran such as 2H-thiopyran and 4H-thiopyran, and 5-membered ring system unsaturated such as benzothiopyran such as benzotetrahydrothiopyran heterocyclic and 6-membered unsaturated heterocyclic rings;

Condensed bicyclic heterocyclic rings, such as benzothiopyran, such as benzothiopyran and benzotetrahydrothiopyran, and benzothiophene;

condensed tricyclic heterocycles such as thiantrene and dibenzothiophene; and the like.

[0022] As a heterocyclic ring containing a nitrogen atom and an oxygen atom,

Morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone and 2-methyl-2-pyr monocyclic saturated heterocyclic rings such as peridone;

Monocyclic unsaturated heterocycles, such as isoxazole, such as oxazole, such as oxazole and 4-methyloxazole, 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, 5-methylisoxazole;

Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisooxazole, benzoxazine, benzodioxane, and benzoimidazoline;

condensed tricyclic heterocycles such as phenoxazine; and the like.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom,

monocyclic heterocycles such as thiazoles such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole and 2,4-dimethylthiazole;

Condensed bicyclic heterocyclic rings, such as benzothiazole;

condensed tricyclic heterocycles such as phenothiazine; and the like.

[0024] In addition, the bonding position of the heterocyclic group is a portion from which any hydrogen atoms included in each heterocycle are separated.

[0025] The heterocyclic group may be a combination of the heterocyclic ring exemplified above and the hydrocarbon group exemplified above (preferably one or both of an aliphatic hydrocarbon group and an aromatic hydrocarbon group), for example, a tetrahydrofurylmethyl group ;

[0026]

phthalic anhydride derivatives such as;

and the like.

※ indicates a bonding hand.

[0027] In addition, the heterocyclic group may be represented by the following formula.

※ indicates a bonding hand.

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.} Examples of such groups include the following groups.

[0029] For example, trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2- Ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, diethylaminoethyl group, (4-methoxyphenyl)methyl group, (2-methoxyphenyl)methyl group, (3-methoxyphenyl)methyl group, (4 -Nitrophenyl)methyl group, (2,4-dichlorophenyl)methyl group, (4-fluorophenyl)methyl group, (3,5-difluorophenyl)methyl group, 2,2,2-trifluoro-1-tri Fluoromethyl-1-phenylethyl group, (phenoxy)(phenyl)methyl group, (benzyloxy)(phenyl)methyl group, pyrrolylmethyl group, pyrrolylethyl group, (4-aminophenyl)methyl group, (4-cyanophenyl) methyl group, 2-hydroxy-1-methyl-1-phenylethyl group, 2-chloro-1-methyl-1-phenylethyl group;

-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 of the above monovalent hydrocarbon group or monovalent heterocyclic group -CH ₂ - is a group substituted with -O-;

and alkyl groups having a substituent such as these (hereinafter, these may be referred to as group A groups).

[0030] For example, 4-bromophenyl group, 4-nitrophenyl group, 4-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4- An aryl group having a substituent such as a hydroxy-1-naphthyl group, a 4,5,8-trichloro-2-naphthyl group, an anthraquinonyl group, or a 2-aminoanthraquinonyl group (hereinafter referred to as a group of group B) There is) can be mentioned.

[0031] For example, a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, 2-ethylhexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, dode Canoyl group, henicosanoyl group, benzoyl group,

and a carbonyl group to which the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group are bonded;

A hydrocarbon group having 1 to 30 carbon atoms, groups A to B, or a carbonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable,

A hydrocarbon group having 1 to 20 carbon atoms, groups A to B, or a carbonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 18 carbon atoms, groups A to B, or a carbonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 12 carbon atoms, groups A to B, or a carbonyl group to which a preferable one of the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded is still more preferable.

※ indicates a bonding hand.

[0033] For example, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethylhexyl)oxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group , nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group,

and an oxycarbonyl group to which the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group are bonded;

[0034] A hydrocarbon group having 1 to 30 carbon atoms, a group A to B, or an oxycarbonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable,

More preferable is an oxycarbonyl group to which a preferable one of the hydrocarbon group having 1 to 20 carbon atoms, the groups A to B, or the monovalent hydrocarbon group or the monovalent heterocyclic group is bonded;

More preferably, a hydrocarbon group having 1 to 18 carbon atoms, a group of groups A to B, or an oxycarbonyl group to which a preferable one of the monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 12 carbon atoms, groups A to B, or an oxycarbonyl group to which a preferable one of the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded is still more preferable.

※ indicates a bonding hand.

[0035] For example, a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, (2,2-dimethylpropanoyl)oxy group, pentanoyloxy group, hexanoyloxy group, (2-ethylhexanoyl)oxy group, heptanoyloxy group, octanoyl group Noyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, (2-propenyl)carbonyloxy group , (1-methylethenyl) carbonyloxy group, and a carbonyloxy group to which a group A to B described above or a monovalent hydrocarbon group or a monovalent heterocyclic group is bonded;

A hydrocarbon group having 1 to 30 carbon atoms, a group A to B, or a carbonyloxy group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable,

More preferably, a carbonyloxy group to which a preferable one of the hydrocarbon group having 1 to 20 carbon atoms, the groups A to B, or the monovalent hydrocarbon group or the monovalent heterocyclic group is bonded is more preferable,

More preferably, a carbonyloxy group to which a preferable one of the hydrocarbon group having 1 to 18 carbon atoms, the groups A to B, or the monovalent hydrocarbon group or the monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 12 carbon atoms, groups A to B, or a carbonyloxy group to which a preferable one of the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded is still more preferable.

[0037] For example, a hydroxyl group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, neopentyloxy group, 1-ethyl-1,2-dimethyl propoxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethylhexyl)oxy group, stearyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, benzyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyl group oxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2- methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group;

Trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 3,3,3-trifluoro-2 -Trifluoromethyl-2-methylpropoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, -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 to which the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group are bonded;

A hydrocarbon group having 1 to 30 carbon atoms, an oxy group or a hydroxyl group to which a preferable one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable,

A hydrocarbon group having 1 to 20 carbon atoms, groups A to B, or an oxy group or a hydroxy group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 18 carbon atoms, an oxy group or a hydroxy group to which a preferable one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 12 carbon atoms, an oxy group to which a preferable one of the above-mentioned groups A to B, a monovalent hydrocarbon group or a monovalent heterocyclic group is bonded, or a hydroxy group is even more preferable.

※ indicates a bonding hand.

[0039] For example, a mercapto group; Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethylhexyl)thio group, heptylthio group, octylthio group, nonylthio group , decylthio group, undecylthio group, dodecylthio group, icosylthio group, phenylthio group, o-tolylthio group,

and a mercapto group in which a hydrogen atom is substituted with a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group;

A hydrocarbon group having 1 to 30 hydrogen atoms, a mercapto group or a mercapto group substituted with a preferable one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is preferable ,

A hydrocarbon group having 1 to 20 hydrogen atoms, a mercapto group or a mercapto group substituted with a preferable one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, or a mercapto group is more preferable,

A hydrocarbon group having 1 to 18 hydrogen atoms, a mercapto group or a mercapto group substituted with a preferable one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group, or a mercapto group is more preferable,

A hydrocarbon group having 1 to 12 hydrogen atoms, a mercapto group or a mercapto group substituted with a preferable one of the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is even more preferable.

※ indicates a bonding hand.

[0041] For example, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethylhexyl)sulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decyl group Sulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group,

and a sulfonyl group to which the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group are bonded;

[0042] A hydrocarbon group having 1 to 30 carbon atoms, a group A to B, or a sulfonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable,

A hydrocarbon group having 1 to 20 carbon atoms, groups A to B, or a sulfonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferable,

More preferably, a hydrocarbon group having 1 to 18 carbon atoms, groups A to B, or a sulfonyl group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 12 carbon atoms, groups A to B, or a sulfonyl group to which a preferable one of the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded is still more preferable.

※ indicates a bonding hand.

[0043] For example,

sulfamoyl group;

N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-(sec-butyl ) sulfamoyl group, N-(tert-butyl)sulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethylhexyl) Sulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N- icosylsulfamoyl group, N-phenylsulfamoyl group, -SO 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 , a sulfamoyl group in which one of the above groups A to B or the above monovalent hydrocarbon group or monovalent heterocyclic group is substituted;

[0044] N,N-dimethylsulfamoyl group, N-ethyl-N-methylsulfamoyl group, N,N-diethylsulfamoyl group, N-propyl-N-methylsulfamoyl group, N,N-dipropyl group Sulfamoyl group, N-isopropyl-N-methylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-di(sec-butyl)sulfamo Diyl, N-(tert-butyl)-N-methylsulfamoyl group, N,N-di(tert-butyl)sulfamoyl group, N-butyl-N-methylsulfamoyl group, N,N-dibutylsulfamo group Diyl, N-butyl-N-octylsulfamoyl group, N,N-dipentylsulfamoyl group, N,N-bis(1-ethylpropyl)sulfamoyl group, N-butyl-N-hexylsulfamoyl group, N -Hexyl-N-methylsulfamoyl group, N,N-dihexylsulfamoyl group, N-(2-ethylhexyl)-N-methylsulfamoyl group, N,N-bis(2-ethylhexyl)sulfamoyl group , N,N-diheptylsulfamoyl group, N-octyl-N-methylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N-decyl-N-methylsulfa Moyl group, N-undecyl-N-methylsulfamoyl group, N-dodecyl-N-methylsulfamoyl group, N-icosyl-N-methylsulfamoyl group, N-phenyl-N-methylsulfamoyl group, an N,N-diphenylsulfamoyl group, and a sulfamoyl group substituted with two selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group; ,

[0045] One or two selected from the hydrocarbon group having 1 to 30 carbon atoms, the groups A to B, preferred ones of the above monovalent hydrocarbon groups, and preferred ones of the above monovalent heterocyclic groups are substituted A sulfamoyl group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is preferred,

A sulfamoyl group substituted with one or two selected from a hydrocarbon group having 1 to 20 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups, and preferred among monovalent heterocyclic groups , -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is more preferred,

A sulfamoyl group substituted with one or two selected from a hydrocarbon group having 1 to 18 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups, and preferred among monovalent heterocyclic groups , -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is more preferred,

A sulfamoyl group substituted with one or two selected from a hydrocarbon group having 1 to 12 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups, and preferred among monovalent heterocyclic groups , —SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is even more preferred.

[0046] For example,

carbamoyl group;

N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-(sec-butyl ) Carbamoyl group, N-(tert-butyl)carbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethylhexyl) Carbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N- icosylcarbamoyl group, N-phenylcarbamoyl group, -CONH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -CONHCH ₂ CH ₂ CH ₂ Si(OCH ₂ CH ₃ ) ₃ , and the above groups a carbamoyl group in which one of the groups A to B or the above monovalent hydrocarbon group or monovalent heterocyclic group is substituted;

[0047] N,N-dimethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group, N,N-diethylcarbamoyl group, N-propyl-N-methylcarbamoyl group, N,N-dipropyl group Carbamoyl group, N-isopropyl-N-methylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-di(sec-butyl)carbamo Diyl, N-(tert-butyl)-N-methylcarbamoyl group, N,N-di(tert-butyl)carbamoyl group, N-butyl-N-methylcarbamoyl group, N,N-dibutylcarbamo Diyl, N-butyl-N-octylcarbamoyl group, N,N-dipentylcarbamoyl group, N,N-bis(1-ethylpropyl)carbamoyl group, N-butyl-N-hexylcarbamoyl group, N -Hexyl-N-methylcarbamoyl group, N,N-dihexylcarbamoyl group, N-(2-ethylhexyl)-N-methylcarbamoyl group, N,N-bis(2-ethylhexyl)carbamoyl group , N,N-diheptylcarbamoyl group, N-octyl-N-methylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N-decyl-N-methylcarbamoyl group Bamoyl group, N-undecyl-N-methylcarbamoyl group, N-dodecyl-N-methylcarbamoyl group, N-icosyl-N-methylcarbamoyl group, N-phenyl-N-methylcarbamoyl group, an N,N-diphenylcarbamoyl group, and a carbamoyl group substituted with two selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group; ,

[0048] One or two selected from the hydrocarbon group having 1 to 30 carbon atoms, the groups A to B, preferred ones of the above monovalent hydrocarbon groups, and preferred ones of the above monovalent heterocyclic groups are substituted A carbamoyl group or a carbamoyl group is preferred,

A carbamoyl group substituted with one or two selected from a hydrocarbon group having 1 to 20 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups, and preferred among monovalent heterocyclic groups , or a carbamoyl group is more preferable,

A carbamoyl group substituted with one or two selected from a hydrocarbon group having 1 to 18 carbon atoms, groups A to B, preferred ones of the above monovalent hydrocarbon groups, and preferred ones of the above monovalent heterocyclic groups , or a carbamoyl group is more preferred,

A carbamoyl group substituted with one or two selected from a hydrocarbon group having 1 to 12 carbon atoms, a group of Groups A to B, a preferable one of the aforementioned monovalent hydrocarbon group, and a preferable one of the aforementioned monovalent heterocyclic group , or a carbamoyl group is even more preferred.

[0049] For example,

amino group;

N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-(sec-butyl)amino group, N-(tert-butyl)amino group, N-pentylamino group, N-(1-ethylpropyl)amino group, N-hexylamino group, N-(2-ethylhexyl)amino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N-icosylamino group, N-phenylamino group, and one of the above groups A to B, the above monovalent hydrocarbon group or monovalent heterocyclic group is substituted amino group and the like;

[0050] N,N-dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-propyl-N-methylamino group, N,N-dipropylamino group, N-isopropyl-N -Methylamino group, N,N-diisopropylamino group, N,N-diisobutylamino group, N,N-di(sec-butyl)amino group, N-(tert-butyl)-N-methylamino group, N,N -di(tert-butyl)amino group, N-butyl-N-methylamino group, N,N-dibutylamino group, N-butyl-N-octylamino group, N,N-dipentylamino group, N,N-bis(1 -Ethylpropyl) amino group, N-butyl-N-hexylamino group, N-hexyl-N-methylamino group, N,N-dihexylamino group, N-(2-ethylhexyl)-N-methylamino group, N,N- Bis(2-ethylhexyl)amino group, N,N-diheptylamino group, N-octyl-N-methylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N-decyl-N-methylamino group , N-undecyl-N-methylamino group, N-dodecyl-N-methylamino group, N-icosyl-N-methylamino group, N-phenyl-N-methylamino group, N,N-diphenylamino group, and and an amino group substituted with two selected from the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon group and the above-mentioned monovalent heterocyclic group;

[0051] One or two selected from a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, a preferred one of the above monovalent hydrocarbon group and a preferred one of the above monovalent heterocyclic group is substituted An amino group or an amino group is preferred,

an amino group substituted with one or two selected from a hydrocarbon group having 1 to 20 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups, and preferred among monovalent heterocyclic groups, or an amino group is more preferable,

an amino group substituted with one or two selected from a hydrocarbon group having 1 to 18 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups, and preferred among monovalent heterocyclic groups, or an amino group is more preferred,

an amino group substituted with one or two selected from a hydrocarbon group having 1 to 12 carbon atoms, groups A to B, preferred among monovalent hydrocarbon groups and preferred monovalent heterocyclic groups, or An amino group is even more preferred.

[0052] For example, a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, (2,2-dimethylpropanoyl)amino group, pentanoylamino group, hexanoylamino group, (2-ethylhexanoyl)amino group, heptanoylamino group, octanoylamino group, no Nanoylamino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group,

and a carbonylamino group to which the above-mentioned groups A to B or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group are bonded;

A hydrocarbon group having 1 to 30 carbon atoms, a group A to B, or a carbonylamino group to which a preferable one of the monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable,

More preferably, a carbonylamino group to which a preferable one of the hydrocarbon group having 1 to 20 carbon atoms, the groups A to B, or the monovalent hydrocarbon group or the monovalent heterocyclic group is bonded is more preferable,

More preferably, a carbonylamino group to which a preferable one of the hydrocarbon group having 1 to 18 carbon atoms, the groups A to B, or the monovalent hydrocarbon group or the monovalent heterocyclic group is bonded is more preferable,

A hydrocarbon group having 1 to 12 carbon atoms, groups A to B, or a carbonylamino group to which a preferable one of the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded is still more preferable.

※ indicates a bonding hand.

[0054] 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 selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group;

-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 substituted with 1, 2 or 3 selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group (OH) ₃ and the like;

-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 of groups A to B above group, one, two or three selected from the above monovalent hydrocarbon group and the above monovalent heterocyclic group -SiH(OH) ₂ and the like;

-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 groups A to B above group, one, two or three selected from the monovalent hydrocarbon group and the monovalent heterocyclic group is substituted -SiH ₂ (OH), etc.; and

1, 2, or 3 selected from the hydrocarbon group having 1 to 30 carbon atoms, the groups A to B, preferred ones of the above monovalent hydrocarbon groups, and preferred ones of the above monovalent heterocyclic groups Preference is given to substituted -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ ,

One, two or three selected from preferred among the above-mentioned monovalent hydrocarbon group and above-mentioned monovalent heterocyclic group is substituted with a hydrocarbon group having 1 to 20 carbon atoms, groups A to B above, -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ are more preferable,

One, two, or three selected from preferred among the hydrocarbon group having 1 to 18 carbon atoms, the groups A to B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups are substituted -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ are more preferred,

1, 2 or 3 selected from preferred among the hydrocarbon group having 1 to 12 carbon atoms, the groups A to B, the monovalent hydrocarbon group and the monovalent heterocyclic group are substituted Even more preferred are -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ .

[0059] For example, a phthalimidemethyl group which may have a substituent (C ₆ H ₄ (CO) ₂ N-CH ₂ -) is mentioned, and as the substituent, the above-mentioned halogen atom and the above-mentioned groups A to B and at least one selected from the group consisting of the above monovalent hydrocarbon group and the above monovalent heterocyclic group.

[0060] As other groups, -SCOCH ₃ ,

and the like.

※ indicates a bonding hand.

[0061] the groups monovalent hydrocarbon group or the monovalent heterocyclic group _{^{is, -SO 3 - N + (C}} 12 H 25) (CH 3) 3, -CO 2 - N + (C 12 H 25) (CH 3 ) ₃ , -SO ₃ ^- , -CO ₂ ^-, etc. may be substituted.

[0062] R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ may be bonded to each other to form a ring.

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

[0064] Examples of the metal atom of the metal atom which may have a ligand represented by M and MM include metal atoms belonging to Groups 2 to 15 of the Periodic Table of the Elements. As a metal atom of the metal atom which may have a ligand, More preferably, Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh , Ir, Pd, Ti, Zr, Hf, Si, Ge, more preferably, Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr, even more preferably For example, Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, Cr.

The ligand of the metal atom which may have a ligand is not particularly limited, and for example, a halogen atom, NO, NO ₃ , SO ₄ , CH ₃ CO ₂ , OH, etc. may be used;

The ligand coordinated to the metal atom and the carbon atom, nitrogen atom, oxygen atom, or sulfur atom contained in the same ligand may be coordinated to the same metal atom,

A plurality of different ligands may be coordinated with the same metal atom to the metal atom, and may form an oligomer or a polymer.

In the ligand, when compound (I) contains the metal atom which may have a ligand, compound (I) except the metal atom which may have a ligand is also contained.

Compound (I) of the present invention also contains such an oligomer or polymer.

However, the charge of compound (I) is 0.

[0066] Examples of the compound (I) include metal salts represented by the following formulas (EN1) to (EN5).

However, in formulas (EN1) to (EN5), structures shown in parentheses indicate that they are repeatedly bonded like oligomers and polymers.

For example, the metal salt represented by Formula (EN1) shows that the same ligand is coordinated to the same metal atom.

For example, the metal salts represented by formulas (EN2) to (EN3) indicate that a plurality of different ligands are coordinated to the same metal atom.

For example, the metal salts represented by the formulas (EN4) to (EN5) indicate that a plurality of different ligands are coordinated to the same metal atom to form an oligomer or a polymer.

[0067]

[0068]

[0069]

[0070]

[0071]

^{As N(Z 1} )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM,

NH ₄ ; a group in which one alkyl group is substituted for _{NH 4 such as NH 3} ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), and the like;

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 , N a group in which 4 alkyl groups are substituted for _{NH 4} such as (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 ;}

_{And, NH 4} substituted with 1, 2, 3 or 4 selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group

and the like.

[0073] M is,

hydrogen atom;

alkali metal atoms;

Mg which may have ligand, Ca which may have ligand, Sr which may have ligand, Ba which may have ligand, Ni which may have ligand, Zn which may have ligand, Cu which may have ligand, ligand Fe which may have, 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;

NH ₄ ;

a group in which one alkyl group is substituted for _{NH 4 such as NH 3} ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), and the like;

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 , N (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 A} group in which 4 alkyl groups are substituted for NH _{4 such as}

is preferably

[0074] hydrogen atom;

sodium atom, potassium atom;

Mg which may have ligand, Ca which may have ligand, Sr which may have ligand, Ba which may have ligand, Ni which may have ligand, Zn which may have ligand, Cu which may have ligand, ligand Fe which may have, 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 ;

a group in which one alkyl group is substituted for _{NH 4 such as NH 3} ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), and the like;

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 , N (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 A} group in which 4 alkyl groups are substituted for NH _{4 such as}

is more preferable.

[0075] MM is,

alkali metal atoms;

Mg which may have ligand, Ca which may have ligand, Sr which may have ligand, Ba which may have ligand, Ni which may have ligand, Zn which may have ligand, Cu which may have ligand, ligand Fe which may have, 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;

NH ₄ ;

a group in which one alkyl group is substituted for _{NH 4 such as NH 3} ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), and the like;

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 , N (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 A} group in which 4 alkyl groups are substituted for NH _{4 such as}

is preferably

[0076] a sodium atom, a potassium atom;

Mg which may have ligand, Ca which may have ligand, Sr which may have ligand, Ba which may have ligand, Ni which may have ligand, Zn which may have ligand, Cu which may have ligand, ligand Fe which may have, 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 ;

a group in which one alkyl group is substituted for _{NH 4 such as NH 3} ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), and the like;

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 , N (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 A} group in which 4 alkyl groups are substituted for NH _{4 such as}

is more preferable.

[0077] Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,

-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

Even if the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.

However, ^{at least one of Q 1} and Q ² has a group represented by the formula (y).

Y ¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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.}

※ indicates a bonding hand.

The group substituting a hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group may be a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or a contribution represented by the formula (y), The contribution represented by a halogen atom, a cyano group, a nitro group, -SO ₃ H, -CO ₂ H, or a formula (y) may also be sufficient.

[0078] Q ^{1 preferably} has a group represented by formula (y), and Q ² preferably has a group represented by formula (y).

Q ¹ and Q ² may be the same or different, and preferably the same.

It is preferable that Q<^1> and Q<^2> are groups represented by a formula (QQ1) - a formula (QQ19).

[0079]

[0080]

[0081] In [Formula (QQ1) to Formula (QQ19),

R ^Q1 to ^{R Q94} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a group represented by the formula (y), 1 having 1 to 40 carbon atoms Represents a valent hydrocarbon group or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

Even if the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.

R ^Q1 ~R ^Q94 are bonded to each other with at least one selected from a, R ~R ^{Q1 Q94} respectively form a ring.

M, MM, Z ^{1 to Z 4} , the group represented by the formula (y), and Y ¹ have the same meanings as described above.

※ indicates a bonding hand.]

a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by ^{R Q1} to ^{R Q94;}

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

Roth,

R ¹ ~R ^5, Z ¹ ~Z and ^4, and where Y group having a carbon number of 1 to 40 carbon atoms or a monovalent hydrocarbon group of 1 to 40 of the monovalent heterocyclic group represented by ^1,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

can be the same as

a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by ^{R Q1} to ^{R Q94;}

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

Among the preferred ones,

R ¹ ~R ^5, Z ¹ ~Z and ^4, and where Y group having a carbon number of 1 to 40 carbon atoms or a monovalent hydrocarbon group of 1 to 40 of the monovalent heterocyclic group represented by ^1,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

Hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group are the same as preferred among groups optionally substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO _{2 M or MM.} can

[0084] Preferred ^{examples of R Q1} to ^{R Q94 include the same ones as preferred among R 1} to ^{R 5} and Y ¹ and a group represented by the formula (y).

Each of the formulas (QQ1) to (QQ19) preferably contains at least one ethynylene group, and more preferably has a group represented by the formula (y).

[0085] Q ¹ and Q ² are,

It is preferable that it is a group represented by a formula (QQ1) - a formula (QQ12),

It is more preferable that it is a group represented by a formula (QQ1) - a formula (QQ5),

It is more preferably a group represented by the formulas (QQ1) to (QQ4),

It is still more preferably a group represented by the formulas (QQ1) and (QQ2),

It is still more preferable that it is group represented by a formula (QQ1).

[0086] The formulas (QQ1) to (QQ19) include, for example, the following formulas (Qa1) to (Qa50); Formulas (Qb1) to (Qb27); Formulas (Qc1) to (Qc56); Formulas (Qd1) to (Qd41); Formulas (Qe1) to (Qe16); Formulas (Qf1) to (Qf15); Formulas (Qg1) to (Qg40); Formulas (Qh1) to (Qh40); Formulas (Qj1) to (Qj29); Formulas (Qk1) to (Qk22); Formulas (Qm1) to (Qm20); Formulas (Qn1) to (Qn16); Formulas (Qo1) to (Qo15); Formulas (Qp1) to (Qp83); Formulas (Qq1) to (Qq72); Formulas (Qr1) to (Qr17); Formulas (Qs1) to (Qs26); Formulas (Qt1) to (Qt26); Formulas (Qu1) to (Qu17); Formulas (Qv1) to (Qv26); Formulas (Qx1) to (Qx2); Formulas (Qy1) to (Qy74); Formulas (Qz1) to (Qz28); and groups represented by formulas (Qaa1) to (Qaa10). However, ※ indicates a bond.

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] The compound represented by formula (I) is preferably a compound represented by formula (I') (hereinafter sometimes referred to as compound (I')).

[In formula (I'),

R ¹ to ^{R 5} each have the same meaning as described above.

R ⁶ to ^{R 13} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a group represented by the formula (y), 1 having 1 to 40 carbon atoms Represents a valent hydrocarbon group or a monovalent heterocyclic group having 1 to 40 carbon atoms,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon 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 ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁸ and R ⁹ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , and R ¹² and R ¹³ may be bonded to each other to form a ring, respectively.

provided ^{that at least one of R 6} to ^{R 13} is a group represented by the formula (y).]

[0137] A monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by ^{R 6} to ^{R 13 ,}

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

Roth,

R ¹ ~R ^5, Z ¹ ~Z and ^4, and where Y group having a carbon number of 1 to 40 carbon atoms or a monovalent hydrocarbon group of 1 to 40 of the monovalent heterocyclic group represented by ^1,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

can be the same as

[0138] A monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by ^{R 6} to ^{R 13 ,}

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

Among the preferred ones,

R ¹ ~R ^5, Z ¹ ~Z and ^4, and where Y group having a carbon number of 1 to 40 carbon atoms or a monovalent hydrocarbon group of 1 to 40 of the monovalent heterocyclic group represented by ^1,

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;

-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;

-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;

_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}

The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be substituted with a _{halogen atom, a cyano group, a nitro group, -SO 3} M, -CO _{2 M or MM.}

Among them, the same as preferred ones can be mentioned.

[0139] Preferred ^{examples of R 6} to ^{R 13 include the same ones as preferred among R 1} to ^{R 5} and Y ¹ and a group represented by the formula (y).

At least one of R ⁶ to ^{R 9} is preferably a group represented by the formula (y), and ^{at least one of R 10} to ^{R 13} is preferably a group represented by the formula (y), and among ^{R 6} to ^{R 9} It is more preferable that at least one is a group represented by the formula (y), and ^{at least one of R 10} to ^{R 13} is a group represented by the formula (y).

[0140] The compound (I) includes, for example, a compound represented by the formula (Ia) shown in Tables 1 to 7 below, or an alkali metal salt thereof.

Further, "Q ^1" in Tables 1 to 7 and symbols is described in the "Q ^2" column, there are corresponding groups represented by the above formula.

※ indicates a bonding hand.

[0141]

[0142] [Table 1]

[0143] [Table 2]

[0144] [Table 3]

[0145] [Table 4]

[0146] [Table 5]

[0147] [Table 6]

[0148] [Table 7]

[0149] The compound (I) includes, for example, a compound represented by the formula (Ib) shown in Tables 8 to 27 below, or an alkali metal salt thereof.

[0150]

[0151] In formula (Ib), ^{any one of R Ib1} to ^{R Ib5} is an RR group, and the other four are hydrogen atoms.

^{The symbols described in the “Q 1} ” column and the “Q ² ” column in Tables 8 to 27 correspond to groups represented by the above formulas, respectively.

The symbols described in the "RR" column in Tables 8 to 27 represent the RR groups, and each of the following

Formulas (a1) to (a69);

Formulas (b1) to (b4);

Formulas (c1) to (c4);

Formulas (d1) to (d5);

Formulas (e1) to (e20);

Formulas (f1) to (f5);

Formulas (g1) to (g9);

Formulas (h1) to (h9);

Formulas (j1) to (j9);

Formulas (k1) to (k4);

Formulas (m1) to (m9);

Formulas (n1) to (n3);

Formulas (o1) to (o5);

Formulas (p1) to (p23);

Formulas (q1) to (q26);

Formulas (r1) to (r26);

Formulas (s1) to (s26);

formula (t1);

It corresponds to the group represented by

Numerical values described in the "No" column in Tables 8 to 27 indicate positions at which RR groups are substituted, respectively,

"1" indicates that the RR group is substituted with ^{R Ib1,}

"2" indicates that the RR group is substituted with ^{R Ib2,}

"3" indicates that the RR group is substituted with ^{R Ib3,}

"4" indicates that the RR group is substituted with ^{R Ib4,}

"5" indicates that the RR group is substituted with ^{R Ib5.}

※ indicates a bonding hand.

[0152] [Table 8]

[0153] [Table 9]

[0154] [Table 10]

[0155] [Table 11]

[0156] [Table 12]

[0157] [Table 13]

[0158] [Table 14]

[0159] [Table 15]

[0160] [Table 16]

[0161] [Table 17]

[0162] [Table 18]

[0163] [Table 19]

[0164] [Table 20]

[0165] [Table 21]

[0166] [Table 22]

[0167] [Table 23]

[0168] [Table 24]

[0169] [Table 25]

[0170] [Table 26]

[0171] [Table 27]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] The compound (I) includes, for example, a compound represented by the formula (If) shown in Tables f1 to f6 below, or an alkali metal salt thereof.

In addition, Table f1~ table "Q ^1" is the symbol described in "Q ^2", and is in the f6, and corresponding groups represented by the above formula.

※ indicates a bonding hand.

[0183]

[0184] [Table f1]

[0185] [Table f2]

[0186] [Table f3]

[0187] [Table f4]

[0188] [Table f5]

[0189] [Table f6]

_{[0190] As compound (I), for example, -SO 3} H to a compound represented by formulas (Ia1) to (Ia1050), (Ib1) to (Ib1532), and (If1) to (If1367), , -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidemethyl group (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 in which at least one selected from a fluorine atom, a chlorine atom and a bromine atom is substituted can be heard

[0191] For example, the compound in which -SO ₃ H is substituted for the compound represented by the formula (Ia3) in Table 1 has the following structure. However, in the formula, -(SO ₃ H) shall mean that all or one or more hydrogen atoms of the compound represented by the formula (Ia3) are substituted with _{-SO 3 H.}

[0192]

[0193] Examples of such a compound include compounds represented by formulas (Ic1) to (Ic3) in which all of the hydrogen atoms of the aromatic ring are substituted with one or more selected from fluorine atoms, chlorine atoms and bromine atoms. can

[0194]

_{[0195] As compound (I), for example, -SO 3} H to the compound represented by formulas (Ia1) to (Ia1050), (Ib1) to (Ib1532), and (If1) to (If1367), , -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidemethyl group (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 ), at least one selected from a fluorine atom, a chlorine atom and a bromine atom, 1 to 6 Dog substituted compounds are also mentioned.

[0196] For example, a compound in which 1 to 6 -SO ₃ H is substituted in the compound represented by the formula (Ia3) in Table 1 has the following structure. However, in the formula, -(SO ₃ H) ₁ to 6 means that any of 1 to 6 hydrogen atoms in the compound represented by the formula (Ia3) are substituted with _{—SO 3 H.}

[0197]

[0198] As compound (I), for example, to compounds represented by formulas (Ia1) to (Ia1050), (Ib1) to (Ib1532), and (If1) to (If1367),

one or more substituted anions selected from -SO ₃ ^- and -CO ₂ ^-;

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 ⁺ , a metal salt comprising at least one cation selected from ^{Na +} and K ^{+ .}

[0199] As compound (I), for example, an anion represented by formula (Id) shown in Table 28 below and an anion represented by formula (Ih) shown in Table h1;

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 ⁺ , a metal salt comprising at least one cation selected from ^{Na +} and K ^{+ .}

[0200] The ^{symbols described in the “Q 1} ” column and “Q ² ” column in Tables 28 and h1 are the groups represented by the above formulas and the following formulas (Qw1) to (Qw11), respectively. is responding to the

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] [Table 28]

[0207] [Table h1]

[0208] Examples of such metal salts include metal salts represented by formulas (Ie) shown in Tables 29 to 30 below.

As symbols described in Table 30 Table 29~ "Met" field of the Mg2 + is represents Mg ^2+,

Ca2 + is represents a Ca ^2+,

Sr2 + is represents Sr ^2+,

Ba2 + is represents a Ba ^2+,

Ni2 + is represents a Ni ^2+,

Zn2 + is represents a Zn ^2+,

Fe2 + is represents a Fe ^2+,

Co2 + is represents a Co ^2+,

Sn2 + is represents a Sn ^2+,

Mn2 + is represents Mn ^2+,

Al3 + is represents the Al ^3+,

Fe3+ represents ^{Fe 3+,}

Cr3+ represents ^{Cr 3+,}

Sn4 + is represents a Sn ^4+,

Mn4 + is represents the Mn ^4+,

Cu2+ represents ^{Cu 2+,}

Li+ represents ^Li+,

Na+ represents ^Na+,

K+ represents ^K+.

[0209] The ^{symbols described in the “Q 1} ” column and “Q ² ” column in Tables 29 to 30 correspond to groups represented by the above formulas, respectively.

m in Formula (Ie) is an integer of 1 or more, Preferably it is an integer of 1-20, More preferably, it is an integer of 1-10.

n in formula (Ie) is an integer of 1 or more, Preferably it is an integer of 1-20, More preferably, it is an integer of 1-10.

However, when the compound (I) of the present invention is the above oligomer or polymer, m and n are the minimum integers representing the ratio of the number of ligands and the number of metal atoms for which the charge of compound (I) becomes zero. It indicates that compound (I) is the above oligomer or polymer.

[0210]

[0211] [Table 29]

[0212] [Table 30]

[0213] As compound (I),

compounds represented by formulas (Ia1) to (Ia903);

a compound represented by the formula (Ia972);

compounds represented by formulas (If1) to (If1355);

To the compound represented by the formulas (Ia1) to (Ia903), (Ia972) and (If1) to (If1355),

-SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidemethyl group (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 ), at least one selected from a fluorine atom, a chlorine atom and a bromine atom substituted compounds; and

an anion substituted with at least one selected from _{-SO 3} ^- and -CO ₂ ^- in the compound represented by the formulas (Ia1) to (Ia903), (Ia972) and (If1) to (If1355);

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 ⁺ , a metal salt consisting of one or more cations selected from ^{Na +} and K ⁺

This is preferable,

[0214] compounds represented by formulas (Ia1) to (Ia903);

a compound represented by the formula (Ia972);

compounds represented by formulas (If1) to (If1355);

To the compound represented by the formulas (Ia1) to (Ia903), (Ia972) and (If1) to (If1355),

one or more substituted compounds selected from -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a fluorine atom, a chlorine atom and a bromine atom; and

an anion represented by the formulas (Id1) to (Id152) and (Ih1) to (Ih170);

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 ⁺ , a metal salt consisting of one or more cations selected from ^{Na +} and K ⁺

This is more preferable,

[0215] The compounds represented by the formulas (Ia1) to (Ia903), (Ia972) and (If1) to (If1355) are more preferable,

Further preferred are compounds represented by formulas (Ia1) to (Ia903),

The compounds represented by formulas (Ia1) to (Ia119) are still more preferable,

Compounds represented by formulas (Ia1) to (Ia5), (Ia26) and (Ia87) to (Ia89) are particularly preferred,

Compounds represented by formulas (Ia2) to (Ia3) are extremely preferred,

The compound represented by the formula (Ia3) is most preferred.

[0216] The compound represented by the formula (I) can be produced by a reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3).

[0217] In formulas (pt1) to (pt3), R ¹ to ^{R 5} , Q ¹ and Q ² have the same meanings as above.

[0218] In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) and the compound represented by the formula (pt3), the amount of the compound represented by the formula (pt2) to be used is, It is usually 0.1-30 mol with respect to 1 mol of the compound represented by pt1), Preferably it is 1-20 mol, More preferably, it is 1-16 mol, More preferably, it is 1-10 mol.

[0219] In the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3), the amount of the compound represented by the formula (pt3) to be used is, It is usually 0.1-30 mol with respect to 1 mol of the compound represented by pt1), Preferably it is 1-20 mol, More preferably, it is 1-16 mol, More preferably, it is 1-10 mol.

The reaction temperature is usually -100 to 300 ° C, preferably 0 to 280 ° C, more preferably 50 to 250 ° C, still more preferably 100 to 230 ° C, still more preferably 150 to It is 200 °C.

[0221] The reaction time is usually 0.5 hours to 500 hours.

[0222] The reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

[0223] As the solvent, 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 (eg, 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; Sulfoxide solvents, such as dimethyl sulfoxide, are mentioned,

[0224] Preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1, 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethylsulfoxide. can,

[0225] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1 , 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

[0226] More preferably, methyl benzoate is mentioned.

[0227] The amount of the solvent used is, in the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3), the compound 1 represented by the formula (pt1) It is 1-1000 mass parts normally with respect to mass part.

[0228] In the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3), it is preferable that at least one selected from an acid and a metal salt coexist.

[0229] Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid; and the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid. and more preferably benzoic acid.

[0230] The amount of acid used in the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3) is 1 mole of the compound represented by the formula (pt1) It is usually 1 to 90 moles, preferably 1 to 70 moles, more preferably 1 to 50 moles, and still more preferably 1 to 30 moles.

[0231] Examples of the metal salt include zinc chloride and aluminum chloride.

[0232] The amount of the metal salt used in the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is 1 mole of the compound represented by the formula (pt1) It is usually 0.01 to 30 moles, preferably 0.01 to 20 moles, more preferably 0.01 to 10 moles, and still more preferably 0.01 to 3 moles.

[0233] A method for extracting compound (I) from the reaction mixture is not particularly limited, and extraction may be performed by various known methods.

For example, after completion of the reaction, compound (I) in the reaction mixture is difficult to dissolve, but compounds other than compound (I) are easily dissolved in a solvent such as methanol, the reaction mixture is added, mixed well, and filtered, It is possible to extract compound (I). In addition, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide or a mixed solvent thereof, or an alkaline solution such as an aqueous sodium hydroxide solution After washing the obtained residue with an aqueous solution and/or an acidic aqueous solution such as hydrochloric acid, it is washed with a low boiling point alcohol such as water or methanol or a mixed solvent thereof to obtain compound (I) may be extracted. Moreover, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization, etc.;

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

After completion of the reaction, compound (I) in the reaction mixture is difficult to dissolve, but compounds other than compound (I) are easily dissolved, the reaction mixture is well mixed with a solvent such as methanol, and then filtered to obtain Compound (I) It is possible to extract Moreover, you may refine|purify by column chromatography and/or recrystallization etc.

[0234] The compound represented by formula (I) is,

A compound represented by the formula (I") (hereinafter sometimes referred to as compound (I")) is prepared by the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), , next,

By hydrolyzing the compound represented by the formula (I") in the presence of a base, the compound represented by the formula (IM1) (hereinafter sometimes referred to as compound (IM1)) is prepared, and further,

It can manufacture by reaction between the compound represented by Formula (IM1), and the compound represented by Formula (pt3).

[0235] In formulas (pt1), (pt2), (pt3), (I"), and (IM1), R ¹ to ^{R 5} and Q ¹ have the same meanings as above.

[0236] In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), the amount of the compound represented by the formula (pt2) to be used is in 1 mole of the compound represented by the formula (pt1) To that, it is usually 0.1 to 60 moles, preferably 1 to 40 moles, more preferably 1 to 32 moles, still more preferably 2 to 20 moles.

[0237] In the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3), the amount of the compound represented by the formula (pt3) to be used is in 1 mole of the compound represented by the formula (IM1) To that, it is usually 0.1 to 30 moles, preferably 1 to 20 moles, more preferably 1 to 16 moles, still more preferably 1 to 10 moles.

[0238] The reaction temperature in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) The reaction temperature in It is 200 °C.

[0239] Reaction time in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) The reaction time is usually 0.5 hours to 500 hours.

[0240] The reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually a solvent carried out in the presence of

[0241] As a solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or between the compound represented by the formula (IM1) and the compound represented by the 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, 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 (eg, 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and the like,

[0242] Preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1, 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethylsulfoxide. can,

[0243] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1 , 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

[0244] More preferably, methyl benzoate is mentioned.

[0245] The amount of the solvent used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by the formula (pt1) is wealth

[0246] The amount of the solvent used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 1-1000 mass parts per 1 part by mass of the compound represented by the formula (IM1) is wealth

[0247] In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or between the compound represented by the formula (IM1) and the compound represented by the formula (pt3), an acid and a metal salt It is preferable that at least one selected from the group coexist.

[0248] As an acid in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) , inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid; and the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid. and more preferably benzoic acid.

[0249] The amount of the acid used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 1 to 90 moles with respect to 1 mole of the compound represented by the formula (pt1). , Preferably it is 1-70 mol, More preferably, it is 1-50 mol, More preferably, it is 1-30 mol.

[0250] The amount of acid used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 1 to 90 moles with respect to 1 mole of the compound represented by the formula (IM1). , Preferably it is 1-70 mol, More preferably, it is 1-50 mol, More preferably, it is 1-30 mol.

[0251] As a metal salt in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) , zinc chloride, aluminum chloride, and the like.

[0252] The amount of the metal salt used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 0.01 to 30 moles with respect to 1 mole of the compound represented by the formula (pt1). , Preferably it is 0.01-20 mol, More preferably, it is 0.01-10 mol, More preferably, it is 0.01-3 mol.

[0253] The amount of the metal salt used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 0.01 to 30 moles with respect to 1 mole of the compound represented by the formula (IM1). , Preferably it is 0.01-20 mol, More preferably, it is 0.01-10 mol, More preferably, it is 0.01-3 mol.

[0254] The method for extracting the compound represented by the formula (I") from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is not particularly limited, and known It can be extracted in a variety of ways.

For example, after completion of the reaction, compound (I") in the reaction mixture is difficult to dissolve, but compounds other than compound (I") are easily dissolved, such as methanol, and a solvent such as methanol, well mixed with the reaction mixture, and then filtered, It is possible to extract compound (I"). Further, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or a sulfoxide solvent such as dimethylsulfoxide, or After washing the obtained residue with a mixed solvent thereof, an alkaline aqueous solution such as aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid, low-boiling alcohol such as water or methanol, or a mixed solvent thereof, You may extract compound (I"). Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization, etc.;

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

After completion of the reaction, the compound (I") in the reaction mixture is difficult to dissolve, but the reaction mixture is well mixed with a solvent such as methanol, in which compounds other than compound (I") are easily dissolved, and then filtered to obtain the compound ( I") can be extracted. Further, it may be purified by column chromatography and/or recrystallization or the like.

[0255] A method for extracting the compound represented by the formula (I) from the reaction mixture in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is not particularly limited, and a known method It is possible to extract in various ways.

For example, after completion of the reaction, compound (I) in the reaction mixture is difficult to dissolve, but compounds (I) other than compound (I) are easily dissolved, the reaction mixture is well mixed with a solvent such as methanol, and then filtered to obtain the compound ( It is possible to extract I). In addition, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide or a mixed solvent thereof, or an alkaline solution such as an aqueous sodium hydroxide solution After washing the obtained residue with an aqueous solution and/or an acidic aqueous solution such as hydrochloric acid, compound (I) may be extracted by washing with water or a low-boiling alcohol such as methanol or a mixed solvent thereof. Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization, etc.;

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

After completion of the reaction, compound (I) in the reaction mixture is difficult to dissolve, but compounds other than compound (I) are easily dissolved, the reaction mixture is well mixed with a solvent such as methanol, and then filtered to obtain Compound (I) It is possible to extract Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

[0256] Examples of the base in the hydrolysis reaction of the compound represented by formula (I") in the presence of a base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1, Organic bases such as 8-diazabicyclo[5.4.0]undeca-7-ene and 1,5-diazabicyclo[4.3.0]nona-5-ene, sodium methoxide, sodium ethoxide, sodium tert -metal alkoxides such as butoxide and potassium tert-butoxide, organometallic compounds such as methyllithium, butyllithium, tert-butyllithium and phenyllithium, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, Inorganic bases, such as sodium hydroxide and potassium hydroxide, etc. are mentioned,

Inorganic bases are preferred,

Lithium hydroxide, sodium hydroxide, and potassium hydroxide are more preferable,

Sodium hydroxide and potassium hydroxide are more preferred,

Potassium hydroxide is even more preferred.

[0257] The amount of the base used in the hydrolysis reaction of the compound represented by formula (I") in the presence of a base is usually 0.1 to 100 moles with respect to 1 mole of the compound represented by formula (I"), Preferably it is 1-70 mol, More preferably, it is 2-40 mol.

[0258] The amount of water used in the hydrolysis reaction of the compound represented by the formula (I") in the presence of a base is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (I"), Preferably, it is 1-200 mass parts, More preferably, it is 1-100 mass parts, More preferably, it is 1-50 mass parts.

[0259] The reaction temperature in the hydrolysis reaction of the compound represented by formula (I") in the presence of a base is usually 0 to 100 ° C, preferably 5 to 100 ° C, more preferably, It is 20-100 degreeC, More preferably, it is 40-100 degreeC, More preferably, it is 60-100 degreeC.

[0260] The reaction time in the hydrolysis reaction of the compound represented by formula (I") in the presence of a base is usually 0.5 to 120 hours, preferably 1 to 72 hours, more preferably, 1 to 24 hours.

[0261] 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 a base is not particularly limited, and various known methods are used. It is possible to extract

For example, after completion of the reaction, compound (IM1) can be extracted by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture for neutralization, followed by filtration. Further, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, Compound (IM1) may be extracted by washing the resulting residue with 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 . Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization, etc.;

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

After completion of the reaction, it is possible to extract compound (IM1) by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture for neutralization, followed by filtration. Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

[0262] The compound represented by formula (I) is,

A compound represented by the formula (IM2) (hereinafter sometimes referred to as compound (IM2)) is prepared by reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3), and then ,

It can manufacture by reaction between the compound represented by Formula (IM2), and the compound represented by Formula (pt2).

[0263]

[0264] In formulas (pt1), (pt2), (pt3), and (IM2), R ¹ to ^{R 5} , Q ¹ , and Q ² have the same meanings as above.

[0265] In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3), the amount of the compound represented by the formula (pt3) to be used is in 1 mole of the compound represented by the formula (pt1) To that, it is usually 0.1 to 10 moles, preferably 0.1 to 5 moles, more preferably 0.5 to 2 moles, still more preferably 0.8 to 1.5 moles.

[0266] The reaction temperature in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually -100 to 300°C, preferably 0 to 280°C, more preferably is 50 to 250 °C, more preferably 100 to 230 °C, still more preferably 120 to 200 °C.

[0267] The reaction time in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 0.5 to 500 hours.

[0268] The reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

[0269] Examples of the solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) include water; nitrile solvents such as acetonitrile; Alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol ; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and the like,

[0270] Preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide can be heard,

[0271] More preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, , 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, and N-methylpyrrolidone,

[0272] More preferably, phenol and methyl benzoate may be mentioned,

[0273] Even more preferably, phenol is mentioned.

[0274] The amount of the solvent used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by the formula (pt1) part, Preferably it is 1-200 mass parts, More preferably, it is 1-100 mass parts, More preferably, it is 1-50 mass parts.

[0275] The method for extracting 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 extraction is performed by various known methods. it is possible to do

For example, after completion of the reaction, the compound (IM2) in the reaction mixture is difficult to dissolve, but the reaction mixture is well mixed with a solvent such as methanol, in which compounds other than compound (IM2) are easily dissolved, and then filtered to obtain the compound ( It is possible to extract IM2).

Further, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, Washing the obtained residue with 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 extract compound (IM2) possible.

Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization, etc.;

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

After completion of the reaction, the compound (IM2) in the reaction mixture is difficult to dissolve, but the reaction mixture is well mixed with a solvent such as methanol, in which a compound other than compound (IM2) is easily dissolved, and then filtered to obtain Compound (IM2) It is possible to extract Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

[0276] In the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2), the amount of the compound represented by the formula (pt2) to be used is in 1 mole of the compound represented by the formula (IM2) To that, it is usually 0.1 to 30 moles, preferably 1 to 20 moles, more preferably 1 to 16 moles, still more preferably 1 to 10 moles.

[0277] The reaction temperature in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually -100 to 300°C, preferably 0 to 280°C, more preferably is 50 to 250 °C, more preferably 100 to 230 °C, still more preferably 150 to 200 °C.

[0278] The reaction time in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.5 hours to 500 hours.

[0279] The reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually carried out in the presence of a solvent.

[0280] Examples of the solvent in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include water; nitrile solvents such as acetonitrile; Alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol ; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and the like,

[0281] Preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1, 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethylsulfoxide. can,

[0282] More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1 , 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

[0283] More preferably, methyl benzoate is mentioned.

[0284] The amount of the solvent used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 1-1000 mass parts per 1 part by mass of the compound represented by the formula (IM2) is wealth

[0285] In the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2), it is preferable that at least one selected from an acid and a metal salt coexist.

[0286] Examples of the acid in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid. ; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid; and the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid. and more preferably benzoic acid.

[0287] The amount of the acid used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 1 to 90 moles with respect to 1 mole of the compound represented by the formula (IM2). , Preferably it is 1-70 mol, More preferably, it is 1-50 mol, More preferably, it is 1-30 mol.

[0288] Examples of the metal salt in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include zinc chloride and aluminum chloride.

[0289] The amount of the metal salt used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.01 to 30 moles with respect to 1 mole of the compound represented by the formula (IM2). , Preferably it is 0.01-20 mol, More preferably, it is 0.01-10 mol, More preferably, it is 0.01-3 mol.

[0290] The method for extracting the compound represented by the formula (I) from the reaction mixture in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is not particularly limited, and a known method It is possible to extract in various ways.

For example, after completion of the reaction, compound (I) in the reaction mixture is difficult to dissolve, but compounds (I) other than compound (I) are easily dissolved, the reaction mixture is well mixed with a solvent such as methanol, and then filtered to obtain the compound ( It is possible to extract I). In addition, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide or a mixed solvent thereof, or an alkaline solution such as an aqueous sodium hydroxide solution After washing the obtained residue with an aqueous solution and/or an acidic aqueous solution such as hydrochloric acid, compound (I) may be extracted by washing with water or a low-boiling alcohol such as methanol or a mixed solvent thereof. Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization, etc.;

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

After completion of the reaction, compound (I) in the reaction mixture is difficult to dissolve, but compounds other than compound (I) are easily dissolved, the reaction mixture is well mixed with a solvent such as methanol, and then filtered to obtain Compound (I) It is possible to extract Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

_{[0291] A sulfo group or -SO 3} M can be introduced into compound (I) by reacting compound (I) with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid.

Compounds in which a sulfo group or -SO ₃ M is introduced into compound (I) are included in the compounds of the present invention.

_{[0292] The amount of SO 3} used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 2 to 150 moles, more preferably 3 to 100 moles, still more preferably based on 1 mole of compound (I). is 5 to 80 moles.

[0293] SO ₃ in fuming sulfuric acid is usually from 1 to 90 parts by mass, preferably from 5 to 70 parts by mass, more preferably from 10 to 60 parts by mass, still more preferably from 100 parts by mass of fuming sulfuric acid. It is 15-50 mass parts.

[0294] The amount of chlorosulfonic acid to be used is usually 1 to 500 moles, preferably 1 to 300 moles, more preferably 1 to 200 moles, and still more preferably 1 mole to 1 mole of compound (I). -150 moles.

_{[0295] When introducing a sulfo group or -SO 3} M into compound (I) using chlorosulfonic acid, it may be carried out in the presence of a solvent.

Examples of the solvent include halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene. have.

[0296] The amount of the solvent used is usually 1 to 1000 parts by mass based on 1 part by mass of compound (I).

[0297] The reaction temperature for sulfation is usually -20 to 200 °C, preferably -10 to 150 °C, and more preferably 0 to 100 °C. Reaction time is 0.5 to 300 hours normally.

_{[0298] A method for extracting the compound in which a sulfo group or -SO 3} M is introduced into compound (I) from the reaction mixture is not particularly limited, and extraction can be carried out by various known methods.

For example, it is possible to extract a compound in which a _{sulfo group or -SO 3} M is introduced into compound (I) by dropping the reaction mixture on ice after completion of the reaction and filtering the obtained mixture. Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Or, after completion of the reaction, the reaction mixture was added dropwise to the ice and giving the resulting mixture, the introduction of a sulfo compound, or -SO ₃ M in compound (I) is set to the difficult to dissolve, the compound (I) or -SO ₃ A sulfo group in compound (I) by mixing with a hydrophilic organic solvent such as an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, and a mixed solvent thereof, in which a compound other than the compound into which M is introduced is easily dissolved, and filtration It is possible to extract the compound into which -SO _{3 M is introduced.} Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

Alternatively, after completion of the reaction, the reaction mixture is added dropwise to ice, the obtained mixture is neutralized with an aqueous solution such as ammonia, a water-soluble amine, or a mixture thereof, and the mixture is then treated with an alcohol solvent such as methanol or a nitrile solvent such as acetonitrile. and a hydrophilic organic solvent such as a mixed solvent thereof, followed by filtration, and distilling off the solvent of the obtained filtrate to extract a compound in which a _{sulfo group or -SO 3 M is introduced into compound (I).} Furthermore, you may refine|purify by column chromatography and/or recrystallization etc.

[0299] _{Compound (I) having -SO 3} H and/or -CO ₂ H is reacted with a salt having MM, thereby compound (I) having -SO ₃ (MM) and/or -CO ₂ (MM) ) can be prepared.

[0300] The amount of the salt having MM used is usually 0.01 to 100 moles, preferably 0.02 to 50 moles, and more preferably based on 1 mole of compound (I) having _{-SO 3} H and/or -CO _{2 H} Usually 0.1 to 30 moles.

The reaction temperature is usually 0 to 100 °C, preferably 0 to 80 °C, more preferably 0 to 60 °C, still more preferably 0 to 40 °C.

The reaction time is usually 0.5 hours to 500 hours.

[0303] The _{reaction between the compound (I) having -SO 3} H and/or -CO ₂ H and the salt having MM is usually carried out in the presence of a solvent.

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

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

Water is more preferable.

[0304] The amount of the solvent used is usually 1 to 1000 parts by mass, preferably 10 to 500 parts by mass, based on 1 part by mass of compound (I) having _{-SO 3} H and/or -CO _{2 H;} More preferably, it is 20-300 mass parts.

[0305] The _{reaction between the compound (I) having -SO 3} H and/or -CO ₂ H and the salt having MM may be carried out in the presence of a base.

[0306] Examples of the base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undeca-7-ene, 1, Organic bases such as 5-diazabicyclo[4.3.0]nona-5-ene, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide, methyl lithium, butyl organometallic compounds such as lithium, tert-butyllithium and phenyllithium; and inorganic bases such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide;

Inorganic bases are preferred,

Lithium hydroxide, sodium hydroxide, and potassium hydroxide are more preferable,

Sodium hydroxide and potassium hydroxide are more preferred,

Sodium hydroxide is even more preferred.

[0307] The amount of the base used is usually from 1 to 100 moles, preferably from 1 to 50 moles, more preferably from 1 mole to 1 mole of compound (I) having _{-SO 3} H and/or -CO _{2 H} is 1 to 20 moles, more preferably 1 to 10 moles.

_{[0308] A method of extracting Compound (I) having -SO 3} (MM) and/or -CO ₂ (MM) from the reaction mixture is not particularly limited, and extraction may be performed by various known methods.

For example, after completion of the reaction, by filtering the reaction mixture, it is possible to extract compound (I) having _{-SO 3} (MM) and/or -CO _{2 (MM).} Further, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, You may wash and refine|purify the obtained residue with nitrile solvents, such as acetonitrile, water, or these mixed solvents.

[0309] [Coloring composition]

The coloring composition of this invention contains a compound (I) and a solvent (E). According to the coloring composition of the present invention, C.I. Compared with the coloring composition containing Pigment Yellow 138, a darker color filter can be formed. The color filter formed from the coloring composition of this invention is used suitably for display apparatuses, such as a liquid crystal display device. The coloring composition of this invention becomes like this. Preferably they are a yellow composition, an orange composition, a red composition, and a green composition.

[0310] The content rate of solid content in the coloring composition is less than 100 mass%, preferably 0.01 mass% or more and less than 100 mass%, with respect to the total amount of the coloring composition, more preferably 0.1 mass% or more and 99.9% It is mass % or less, More preferably, it is 0.1 mass % or more and 99 mass % or less, More preferably, they are 1 mass % or more and 90 mass % or less, More preferably, they are 1 mass % or more and 80 mass % or less, Especially preferred Preferably, they are 1 mass % or more and 70 mass % or less, Very preferably, they are 1 mass % or more and 60 mass % or less, Most preferably, they are 1 mass % or more and 50 mass % or less.

In this specification, "the total amount of solid content" means the total amount of the component except the solvent (E) from the coloring composition of this invention. The total amount of solid content and content of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography.

[0311] The content of compound (I) in the coloring composition is 100 mass% or less, preferably 0.0001 mass% or more and 99.9999 mass% or less, in the total amount of solid content, more preferably 0.0001 mass% or more and 99 mass% or less more preferably 0.0001 mass% or more and 90 mass% or less, still more preferably 0.0001 mass% or more and 80 mass% or less, still more preferably 0.0001 mass% or more and 70 mass% or less, particularly preferably 0.0001 They are mass % or more and 60 mass % or less, Very preferably, they are 0.0001 mass % or more and 55 mass % or less, Most preferably, they are 0.1 mass % or more and 55 mass % or less.

[0312] [Solvent (E)]

The solvent (E) is not particularly limited, and a solvent commonly used in the field may be used.

The solvent (E) is, for example, an ester solvent (a solvent containing -CO-O- in the molecule and not containing -O-), an ether solvent (containing -O- in the molecule and -CO-O- Solvent not containing), ether ester solvent (solvent containing -CO-O- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -CO-O-) , an alcohol solvent (a solvent containing OH in the molecule and not containing -O-, -CO- and -CO-O-), an aromatic hydrocarbon solvent, an amide solvent, and dimethyl sulfoxide.

[0313] As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone, and the like.

[0314] As the ether solvent, 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, tetra Hydropyran, 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, phenetol and Methylanisole etc. are mentioned.

[0315] As the ether ester solvent, methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-e Methyl oxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-methoxy -2-methylpropionate, 2-ethoxy-2-methylpropionate ethyl, 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, dipropylene glycol methyl ether acetate, etc. are mentioned.

[0316] As the ketone solvent, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentane on, cyclopentanone, cyclohexanone, isophorone, and the like.

[0317] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.

[0318] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene and mesitylene.

[0319] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.

[0320] These solvents may be used in combination of two or more.

[0321] Among the above solvents, organic solvents having a boiling point of 120°C or more and 180°C or less at 1 atm are preferable from the viewpoint of coating properties and drying properties. As a solvent, Preferably, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxy propionate ethyl, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4 -hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, 3-ethoxy Ethyl propionate, 4-hydroxy-4-methyl-2-pentanone, etc. are mentioned.

[0322] The content of the solvent (E) is less than 100% by mass, preferably 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, further preferably, with respect to the total amount of the coloring composition. 1 mass % or more and 99.9 mass % or less, More preferably, they are 10 mass % or more and 99 mass % or less, More preferably, they are 20 mass % or more and 99 mass % or less, Especially preferably, they are 30 mass % or more and 99 mass % or less. and extremely preferably 40 mass % or more and 99 mass % or less, and most preferably 50 mass % or more and 99 mass % or less.

[0323] [Resin (B)]

The resin (B) is preferably an alkali-soluble resin, and at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as “monomer (a)”) It is more preferable that it is a polymer which has a structural unit derived from .).

The resin (B) is a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b)”), and other structural units. It is preferable that it is a copolymer having

As the other structural unit, a structural unit derived from a monomer copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b). Hereinafter, it may be referred to as "monomer (c).") and structural units having an ethylenically unsaturated bond.

[0324] In the present specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations, such as "(meth)acryloyl" and "(meth)acrylate", also have the same meaning.

[0325] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and o-, m-, p-vinylbenzoic acid;

Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid;

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

Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride , unsaturated dicarboxylic acid anhydrides such as dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

Unsaturated mono[(meth)acryl] of polyvalent carboxylic acid having a divalent or higher value, such as monosuccinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl] royloxyalkyl]ester;

unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid;

and the like.

Among these, from the viewpoint of copolymerization reactivity or the solubility of the resin obtained in aqueous alkali solution, acrylic acid, methacrylic acid, o-, m-, p-vinyl benzoic acid, maleic anhydride, and the like are preferable.

[0327] The monomer (b) has a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond polymerizable compound.

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

[0328] As the monomer (b), for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond ( Hereinafter, it may be referred to as a "monomer (b2).") and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as a "monomer (b3)"), etc. are mentioned.

[0329] As the monomer (b1), for example, a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “monomer (b1-1)”) and alicyclic and a monomer (hereinafter, sometimes referred to as “monomer (b1-2)”) having a structure in which an unsaturated hydrocarbon is epoxidized.

[0330] The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond.

As the monomer (b1-1), for example,

Glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m- Vinyl benzyl 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)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6 -Bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris (glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6- tris(glycidyloxymethyl)styrene, etc. are mentioned.

[0331] As the monomer (b1-2), for example, vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Seroxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4- Epoxycyclohexylmethyl (meth)acrylate (eg, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cyclomer (registered trademark) M100; Daicel) Corporation), the compound represented by the formula (BI), the compound represented by the formula (BII), etc. are mentioned.

[0332]

[0333] [In formulas (BI) and (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group It may be substituted.

X ^a and X ^b each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.

R ^c represents an alkanediyl group having 1 to 6 carbon atoms.

* indicates a bond with O.]

[0334] Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, and the like.

[0335] As the alkyl group in which a hydrogen atom is substituted with hydroxy, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, etc. can be heard

[0336] R ^a and R ^b include preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group. .

[0337] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1,5-diyl group. diyl, a hexane-1,6-diyl group, etc. are mentioned.

[0338] X ^a and X ^b include preferably a single bond, a methylene group, an ethylene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, and more preferably a single bond. , *-CH ₂ CH ₂ -O- (* represents a bond with O).

Examples of the compound represented by the formula (BI) include a compound represented by any one of formulas (BI-1) to (BI-15). Among them, formulas (BI-1), formulas (BI-3), formulas (BI-5), formulas (BI-7), formulas (BI-9) and formulas (BI-11) to formulas (BI-15) ) is preferable, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferable.

[0340]

[0341]

[0342] Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), and among them, preferably formula (BII-1) , compounds represented by formulas (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formulas (BII-11) to formula (BII-15); , and more preferably compounds represented by formulas (BII-1), (BII-7), (BII-9) and (BII-15).

[0343]

[0344]

[0345] The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination of two or more. The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. When the compound represented by the formula (BI) and the compound represented by the formula (BII) are used together, their content ratio [the compound represented by the formula (BI): the compound represented by the formula (BII)] is based on a molar basis, Preferably it is 5:95-95:5, More preferably, it is 10:90-90:10, More preferably, it is 20:80-80:20.

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

As the monomer (b2), for example, 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethylox Cetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3 -methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. are mentioned.

[0347] As the monomer (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable.

As a monomer (b3), tetrahydrofurfuryl acrylate (For example, Viscot V#150, the OSAKA ORGANIC CHEMICAL INDUSTRY LTD make), tetrahydrofurfuryl methacrylate, etc. are mentioned, for example.

[0348] The monomer (b) is preferably the monomer (b1) from the viewpoint of further enhancing the reliability of the obtained color filter, such as heat resistance and chemical resistance. Furthermore, a monomer (b1-2) is more preferable at the point which is excellent in the storage stability of a coloring composition.

[0349] As the monomer (c), for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylic Rate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylic Late, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-9-yl ( meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-9-yl (meth) acrylate, dicyclopentanyl Oxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl ( (meth)acrylic acid esters, such as meth)acrylate and benzyl (meth)acrylate;

hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

halogen atom-containing (meth)acrylic acid esters such as 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate;

dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;

Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybi Cyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2 -ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept -2-ene, 5,6-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-methyl Bicyclo[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-phenoxy Cycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexylox) bicyclo unsaturated compounds such as cycarbonyl)bicyclo[2.2.1]hept-2-ene;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl- dicarbonylimide derivatives such as 6-maleimide caproate, N-succinimidyl-3-maleimide propionate and N-(9-acridinyl)maleimide;

vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; and the like.

[0350] Among them, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^{2, 6} ] decan-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-9-yl ( meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, phenyl (meth)acrylate, 2,2,3, 3,4,4,5,5-octafluoropentyl (meth) acrylate, 9-vinylcarbazole, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate and 2-ethylhexyl (meth) ) acrylates and the like.

[0351] As the resin (B), specifically, 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 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/9-vinylcarbazole/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ( meth) acrylate / phenyl (meth) acrylate / o-vinyl benzoic 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 (meth)acrylate/(meth)acrylic acid/vinyltoluene 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) arc Relate / tricyclo [5.2.1.0 ^2,6 ] decenyl (meth) acrylate / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyl oxide Cetane/(meth)acrylic acid/styrene copolymer, benzyl(meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, and Japanese Patent Laid-Open No. H09-106071, Japanese Patent Laid-Open No. 2004- 29518 and the resin of each publication of Unexamined-Japanese-Patent No. 2004-361455, etc. are mentioned.

Especially, as resin (B), the copolymer containing the structural unit derived from the monomer (a) and the structural unit derived from the monomer (b) is preferable.

Resin (B) may combine 2 or more types, In this case, resin (B) is at least,

It is preferable to include at least one copolymer including a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b),

It is more preferable to include at least one copolymer including a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1),

It is more preferable to include at least one copolymer including a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2),

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, 3,4-epoxytri It is still more preferable to include at least one selected from cyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/2-ethylhexyl(meth)acrylate copolymer.

[0352] The weight average molecular weight (Mw) in terms of polystyrene of the resin (B) is preferably 1,000 to 100,000, more preferably 1,000 to 50,000, still more preferably 1,000 to 30,000, still more preferably 3,000 to 30,000, particularly preferably 5,000 to 30,000.

[0353] The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 to 6, more preferably 1 to 5, still more preferably is 1 to 4.

[0354] The acid value (in terms of solid content) of the resin (B) is preferably 10 to 500 mg-KOH/g, more preferably 20 to 450 mg-KOH/g, still more preferably 20 to 400 mg -KOH/g, More preferably, it is 20-370 mg-KOH/g, More preferably, it is 30-370 mg-KOH/g, Even more preferably, it is 30-350 mg-KOH/g, Especially preferably, it is 30 -340 mg-KOH/g, most preferably 30-335 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.

[0355] 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, with respect to the total amount of solid content, more preferably 1 mass% or more and 99 mass% % or less, more preferably 1 mass % or more and 97 mass % or less, still more preferably 1 mass % or more and 95 mass % or less, still more preferably 3 mass % or more and 95 mass % or less, particularly preferably is 5 mass % or more and 95 mass % or less, Very preferably, they are 10 mass % or more and 95 mass % or less.

[0356] [Preparation of compound (I) containing liquid]

After preparing the compound (I) containing liquid containing the compound (I) and the solvent (E) beforehand, the coloring composition of this invention may prepare a coloring composition using this compound (I) containing liquid. When the compound (I) does not dissolve in the solvent (E), the compound (I)-containing liquid may be prepared by dispersing the compound (I) in the solvent (E) and mixing them. The compound (I) containing liquid may contain a part or all of the solvent (E) contained in a coloring composition.

In addition, the said compound (I) containing liquid is contained in the coloring composition of this invention.

[0357] The content of solid content in the compound (I)-containing liquid is less than 100 mass%, preferably 0.01 mass% or more and 99.99 mass% or less, with respect to the total amount of the compound (I)-containing liquid, more preferably 0.1 Mass % or more and 99.9 mass % or less, more preferably 0.1 mass % or more and 99 mass % or less, still more preferably 1 mass % or more and 90 mass % or less, still more preferably 1 mass % or more and 80 mass % or less, Especially preferably, they are 1 mass % or more and 70 mass % or less, Very preferably, they are 1 mass % or more and 60 mass % or less, Most preferably, they are 1 mass % or more and 50 mass % or less.

[0358] The content of compound (I) in the compound (I)-containing liquid is 100 mass% or less, preferably 0.0001 mass% or more and 99.9999 mass% or less, in the total amount of solid content in the compound (I)-containing liquid, more Preferably they are 0.0001 mass % or more and 99 mass % or less, More preferably, they are 1 mass % or more and 99 mass % or less, More preferably, they are 3 mass % or more and 99 mass % or less, More preferably, they are 5 mass % or more. It is 99 mass % or less.

[0359] Compound (I) can be treated with rosin, surface treatment using a derivative into which an acidic group or basic group is introduced, graft treatment to the surface of compound (I) with a polymer compound, etc., if necessary, sulfuric acid atomization method The atomization treatment by the (微粒化 method) etc., the washing process with organic solvent, water, etc. for removing an impurity, the removal process by the ion exchange method of an ionic impurity, etc. may be implemented.

In addition, compound (I), if necessary,

atomization by a salt milling method or the like, crystal structure transformation, and rough uniformity of particle shape and/or particle size;

Compound (I) and water and/or an organic solvent are mixed, stirred with stirring and/or heating to obtain a suspension, and then the suspension is filtered to obtain compound (I) with a changed crystal structure, atomization treatment , particle shaping treatment and/or particle diameter roughening treatment;

By recrystallizing, a treatment for changing the crystal structure of the compound (I), a treatment for atomization, a treatment for shaping the particles, and/or a treatment for approximately uniformizing the particle size;

Compound (I) and water, sulfuric acid or an organic solvent are mixed and stirred while stirring and/or heating to obtain a solution or suspension, and then the solution or suspension is mixed with a poor solvent of compound (I). bad solvent) to obtain a suspension, followed by filtration of the suspension to obtain compound (I) having a changed crystal structure, atomization treatment, particle shaping treatment and/or particle size uniformization treatment;

Compound (I), a derivative, and water and/or an organic solvent are mixed, stirred with stirring and/or heating to obtain a suspension, and then the suspension is filtered to obtain a compound (I) with a changed crystal structure. a treatment for obtaining a mixture, a treatment for mixing compound (I) and a derivative, a treatment for atomization, a treatment for shaping the particles and/or a treatment for roughly equalizing the particle size;

Recrystallization of a mixture of compound (I) and a derivative to obtain a mixture containing compound (I) whose crystal structure has changed, a treatment for mixing compound (I) and a derivative, atomization treatment, particle shaping treatment and/or Roughly equalizing the particle size;

Compound (I), a derivative, and water, sulfuric acid or an organic solvent are mixed and stirred while stirring and/or heating to obtain a solution or suspension, and then the solution or suspension is mixed with the poor solvent of compound (I) After mixing to obtain a suspension, the suspension is filtered to obtain a mixture containing compound (I) whose crystal structure has changed, a treatment for mixing compound (I) and a derivative, atomization treatment, particle shaping treatment and/or or roughly equalizing the particle size;

etc. may be implemented.

When using multiple types of compound (I) or a derivative(s), you may carry out these treatments individually, respectively, and these treatments may be mixed and these treatments may be carried out by multiple types.

It is preferable that the particle diameter of compound (I) is substantially uniform.

[0360] As the organic solvent used for the atomization, mixing, crystal structure transformation, particle shaping and/or roughly uniform particle size treatment,

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 (eg, 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and the like.

[0361] As the poor solvent,

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 (eg, 1,3,5-trimethylbenzene), decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; and the like.

Examples of the derivative include a compound represented by the formula (z), a compound represented by the formula (z1), and the like.

[0363]

[0364]

[0365] When the compound (I)-containing liquid contains a derivative, the content of the derivative is 0.01 parts by mass or more and 100 parts by mass or less, and 0.01 parts by mass or more and 70 parts by mass or less with respect to 100 parts by mass of compound (I). is preferably 0.1 parts by mass or more and 50 parts by mass or less, more preferably 0.1 parts by mass or more and 30 parts by mass or less, still more preferably 0.1 parts by mass or more and 20 parts by mass or less.

[0366] Compound (I) can be uniformly dispersed in the compound (I)-containing liquid by subjecting the compound (I) to a dispersion treatment containing a dispersing agent. When using multiple types of compound (I), you may carry out a dispersion process independently, respectively, and may mix and disperse|distribute multiple types.

[0367] Examples of the dispersant include surfactants, and any surfactants of cationic, anionic, nonionic and amphoteric surfactants may be used. Specifically, surfactants, such as a polyester type, a polyamine type, and an acryl type, etc. are mentioned. These dispersing agents may be used individually or may be used in combination of 2 or more type. As the dispersing agent, if indicated by a brand name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by KYOEISHA CHEMICAL Co., LTD.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajispa (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), DISPERBYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) ( BYK-Chemie Co., Ltd. product) etc. are mentioned.

[0368] When the compound (I)-containing liquid contains a dispersing agent, the amount of the dispersant (solid content) to be used is, for example, 0.01 parts by mass or more and 10000 parts by mass or less, preferably 0.01 parts by mass, based on 100 parts by mass of the compound (I). They are at least 5000 parts by mass, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, still more preferably 0.1 parts by mass or more and 300 parts by mass or less. , More preferably, they are 1 mass part or more and 300 mass parts or less, Especially preferably, they are 5 mass parts or more and 260 mass parts or less.

When the usage-amount of this dispersing agent exists in the said range, there exists a tendency for the compound (I) containing liquid in a more uniformly dispersed state to be obtained.

[0369] After the coloring composition of the present invention contains the resin (B), and a compound (I)-containing liquid containing the compound (I) and the solvent (E) is prepared in advance, the compound (I)-containing liquid is used to When preparing the coloring composition of this invention, the compound (I) containing liquid may contain previously a part or all, Preferably a part of resin (B) contained in a coloring composition. By incorporating the resin (B) in advance, the dispersion stability of the compound (I)-containing liquid can be further improved.

[0370] When the compound (I)-containing liquid contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10000 parts by mass or less, with respect to 100 parts by mass of the compound (I), preferably is 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, still more preferably 0.1 parts by mass or more and 300 parts by mass. is below.

[0371] [Polymerizable compound (C)]

The polymerizable compound (C) is a compound that can be polymerized with an active radical and/or acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, preferably (meth)acrylic acid It is an ester compound.

[0372] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, and 2-hydroxy oxyethyl acrylate, N-vinylpyrrolidone, etc., and the above-mentioned monomer (a), monomer (b), and monomer (c) are mentioned.

[0373] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and 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 ethylenically unsaturated bonds. Examples of the polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and di Pentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) ) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa (meth) acrylate, propylene Glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) An acrylate etc. are mentioned, Preferably dipentaerythritol penta (meth)acrylate and dipentaerythritol hexa (meth)acrylate are mentioned.

[0375] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 50 or more and 3,500 or less, still more preferably 50 or more and 3,000 or less, and still more preferably 150 or more. It is 2,900 or less, Especially preferably, it is 250 or more and 1,500 or less.

[0376] The content of the polymerizable compound (C) is less than 100% by mass, preferably 0.00001% by mass or more and 99.99999% by mass or less, more preferably 1% by mass or more, based on the total amount of solid content in the coloring composition. 99 mass % or less, More preferably, it is 1 mass % or more and 97 mass % or less, More preferably, it is 1 mass % or more and 95 mass % or less, More preferably, it is 1 mass % or more and 90 mass % or less, Especially Preferably they are 2 mass % or more and 80 mass % or less, Very preferably, they are 3 mass % or more and 70 mass % or less.

[0377] [Polymerization Initiator (D)]

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

Examples of the polymerization initiator (D) include oxime compounds such as O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0378] As the O-acyloxime compound, for example, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanyl) Phenyl) octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-( 4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2- imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl- 6-｛2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoylb-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy- 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine and N-benzoyloxy-1-[9-ethyl-6- (2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine; and the like. In addition, as an O-acyl oxime compound, you may use commercial items, such as Irgacure OXE01, OXE02 (above, BASF make), and N-1919 (made by ADEKA CORPORATION). Among them, examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl). At least one selected from the group consisting of octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferable. , N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferable.

[0379] Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)- 2-benzylbutan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one; have. As an alkylphenone compound, you may use commercial items, such as Irgacure 369, 907, 379 (above, BASF make).

Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1 -one, 1-hydroxycyclohexylphenylketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyldimethyl Ketals are also included.

[0380] As the biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3) -dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open Nos. H06-75372, H06-75373, etc.), 2,2'-bis (2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra (dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (eg, Japanese Patent Publication S48- 38403, Japanese Patent Laid-Open No. S62-174204, etc.) and a biimidazole compound in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (for example, Japanese Patent Application Laid-Open No. H07) -10913, etc.) etc. are mentioned.

[0381] As the triazine compound, 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-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2- yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl )-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine etc. are mentioned.

[0382] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. You may use commercial items, such as Irgacure (trademark) 819 (made by BASF).

[0383] Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Benzophenone, o-benzoylmethylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone and benzophenone compounds such as 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compound, etc. are mentioned.

These are preferably used in combination with a polymerization initiation assistant (hereinafter, sometimes referred to as polymerization initiation assistant (D1)) described later, particularly amines.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an oxime compound, and a biimidazole compound, More preferably, it is a polymerization initiator containing an oxime compound, More preferably, it is a polymerization initiator containing an O- acyl oxime compound.

[0385] The content of the polymerization initiator (D) is preferably 0.001% by mass or more and 60% by mass or less, and more preferably 0.01% by mass or more and 50% by mass relative to the total amount of the resin (B) and the polymerizable compound (C). mass% or less.

[0386] [Polymerization initiation aid (D1)]

The coloring composition of this invention may contain a polymerization initiation adjuvant (D1). A polymerization initiation adjuvant (D1) is a compound used in order to accelerate|stimulate superposition|polymerization of the polymeric compound (C) which superposition|polymerization was started by a polymerization initiator (D), or a sensitizer. When a polymerization initiation adjuvant (D1) is included, it is used in combination with a polymerization initiator (D) normally.

Examples of the polymerization initiation auxiliary (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carboxylic acid compound.

[0387] As the amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylamino methyl benzoate, 4-dimethylamino ethyl benzoate, 4-dimethylamino benzoate isoamyl, benzoate 2-dimethylaminoethyl, 4 -Dimethylaminobenzoate 2-ethylhexyl, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis(ethylmethylamino)benzophenone etc. are mentioned, Preferably 4,4'-bis(diethylamino)benzophenone is mentioned. Moreover, you may use commercial items, such as EAB-F (made by HODOGAYA CHEMICAL CO., LTD.), as an amine compound.

[0388] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9, 10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc. are mentioned.

[0389] As the thioxanthone compound, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4- Propoxythioxanthone etc. are mentioned.

[0390] As the carboxylic acid compound, phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanyl and acetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0391] When using these polymerization initiation aids (D1), their content is preferably 0.00001 mass% or more and 60 mass% or less, with respect to the total amount of the resin (B) and the polymerizable compound (C), more preferably is 0.0001 mass % or more and 50 mass % or less.

[0392] [Colorant (A1)]

The coloring composition of this invention may contain the coloring agent (Hereinafter, it may be called coloring agent (A1).) other than compound (I).). The coloring agent (A1) may contain 1 type, or 2 or more types of coloring agents. The colorant (A1) preferably contains at least one selected from a yellow colorant, an orange colorant, a red colorant and a green colorant, and more preferably contains at least one selected from a yellow colorant and a green colorant.

[0393] The colorant (A1) may be a dye or a pigment. As the dye, known dyes can be used, for example, known dyes described in Color Index (published by The Society of Dyers and Colorists) and Dyeing note (SHIKISENSHA CO., LTD. dyes. Further, according to the chemical structure, azo dye, cyanine dye, triphenylmethane dye, xanthene dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine Dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. are mentioned. These dyes may be used independently or may be used in combination of 2 or more type.

[0394] Specifically, dyes having the following color index (C.I.) numbers are exemplified.

C.I. 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 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 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. 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 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. C.I. solvent dyes,

C.I. 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 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;

C.I. 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 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

C.I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, CIs of 104, 105, 106, 109, etc. acid dye,

C.I. 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 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 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. 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 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 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82, etc. C.I. direct dye,

C.I. Disperse Yellow 51, 54, 76;

C.I. Disperse Violet 26, 27;

C.I. Disperse Blue 1, 14, 56, 60, etc. C.I. dispers dye,

C.I. Basic Red 1, 10;

C.I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;

C.I. Basic Violet 2;

C.I. Basic Red 9;

C.I. Basic Green 1; et al. C.I. basic dye,

C.I. Reactive Yellow 2, 76, 116;

C.I. Reactive Orange 16;

C.I. Reactive Red 36; et al. C.I. reactive dyes,

C.I. mordant yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

C.I. Modern 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 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

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. Modern 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 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. C.I. modern dye,

C.I. C.I. of vat green 1 etc. bat dye, etc.

[0395] Furthermore, BASF's product Lumogen (Lumogen, registered trademark), 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 (trademark) F red 305 (made by BASF) is mentioned.

[0396] Further, the compound represented by the formula (z), the compound represented by the formula (z1), and the like can be exemplified.

[0397]

[0398]

[0399] As the pigment, a known pigment can be used, and for example, a pigment classified as a pigment in the Color Index (published by The Society of Dyers and Colorists) is exemplified. These may be used independently and may be used in combination of 2 or more type.

Specifically, 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 yellow pigments;

C.I. Orange pigments, such as pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264 Red pigments, such as 265, 266, 268, 269, 273;

C.I. Blue pigments, such as pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;

C.I. Violet pigments, such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Green pigments, such as Pigment Green 7, 36, 58, 59, 62, 63;

C.I. Brown pigments, such as Pigment Brown 23 and 25;

C.I. Black pigments such as Pigment Black 1, 7, 31, 32

can be heard

[0400] As the colorant (A1), a yellow dye and a yellow pigment (hereinafter, they may be collectively referred to as a "yellow colorant"), an orange dye and an orange pigment (hereinafter referred to collectively as an "orange colorant") Preferred are red dyes and red pigments (hereinafter, these may be collectively referred to as "red colorants"), green dyes and green pigments (hereinafter, these may be collectively referred to as "green colorants"), A yellow colorant and a green colorant are more preferable, a yellow pigment and a green pigment are still more preferable, and a green pigment is still more preferable.

[0401] Examples of the yellow dye include dyes whose hue is classified as yellow among the aforementioned dyes, and examples of the yellow pigment include pigments whose hue is classified as yellow among the aforementioned pigments.

As a yellow colorant, a yellow dye and a yellow pigment are preferable, a yellow pigment is more preferable, a quinophthalone pigment, a metal containing pigment, and an isoindoline pigment are still more preferable, C.I. Pigment Yellow 129, 138, 139, 150, 185, 231 are still more preferred, and C.I. Pigment yellow 138, 139, 150, 185, and 231 are still more preferable.

[0402] Examples of the orange dye include dyes whose hue is classified as orange among the above dyes, and examples of the orange pigment include pigments whose hue is classified as orange among the aforementioned pigments.

As an orange colorant, an orange dye and an orange pigment are preferable, and an orange pigment is more preferable, and C.I. Pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 is more preferable.

[0403] Examples of the red dye include dyes whose hue is classified as red among the above dyes, and examples of the red pigment include pigments whose hue is classified as red among the aforementioned pigments.

As a red colorant, a red dye and a red pigment are preferable, Azo dye, anthraquinone dye, triphenylmethane dye, xanthene dye, perylene dye, azo pigment, diketopyrrolopyrrole pigment, anthraquinone pigment, triphenylmethane dye , xanthene pigments and perylene pigments are more preferred, CI Acid Red 52, C.I. Pigment Red 144, 177, 179, 242, 254 and 269 are more preferred.

[0404] Moreover, as a yellow colorant, an orange colorant, or a red colorant, you may use the xanthene compound etc. which were described in Unexamined-Japanese-Patent No. 2013-235257.

[0405] Examples of the green dye include dyes classified as green among the aforementioned dyes, and examples of green pigments include pigments whose hue is classified as green among the aforementioned pigments.

As the green colorant, a green dye and a green pigment are preferable, a green pigment is more preferable, a phthalocyanine pigment is still more preferable, a halogenated copper phthalocyanine pigment, a halogenated zinc phthalocyanine pigment and a halogenated aluminum zinc phthalocyanine pigment are still more preferable, and C.I. Pigment green 7, 36, 58, 59, 62 and 63 are still more preferable.

[0406] [Preparation of colorant (A1) containing liquid]

When the coloring composition of this invention contains a coloring agent (A1), after preparing the coloring agent (A1) containing liquid containing a coloring agent (A1) and a solvent (E) beforehand, using the said coloring agent (A1) containing liquid, a coloring composition may be prepared. When a coloring agent (A1) does not melt|dissolve in a solvent (E), a coloring agent (A1) containing liquid can be prepared by dispersing and mixing a coloring agent (A1) in a solvent (E). The coloring agent (A1) containing liquid may contain a part or all of the solvent (E) contained in a coloring composition.

[0407] The content rate of the solid content in the colorant (A1)-containing liquid is less than 100 mass%, preferably 0.01 mass% or more and 99.99 mass% or less, with respect to the total amount of the colorant (A1)-containing liquid, more preferably 0.1 They are mass % or more and 99.9 mass % or less, More preferably, they are 0.1 mass % or more and 99 mass % or less, More preferably, they are 1 mass % or more and 90 mass % or less, More preferably, they are 1 mass % or more and 80 mass % or less. and 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.

[0408] The content of the colorant (A1) in the colorant (A1)-containing liquid is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, in the total amount of solid content in the colorant (A1)-containing liquid, more Preferably they are 0.0001 mass % or more and 99 mass % or less, More preferably, they are 1 mass % or more and 99 mass % or less, More preferably, they are 3 mass % or more and 99 mass % or less, More preferably, they are 5 mass % or more. It is 99 mass % or less.

[0409] The colorant (A1) is, if necessary, rosin treatment, surface treatment using a derivative into which an acidic or basic group is introduced, graft treatment to the surface of the colorant (A1) with a polymer compound, etc., atomization by sulfuric acid atomization method, etc. treatment, cleaning treatment with an organic solvent or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc., atomization, mixing, crystal structure conversion, particle shape and/or particle size approximation similar to compound (I) A uniform equalization process or the like may be performed. The colorant (A1) is mixed with the compound (I) as needed, and the mixture is subjected to the same atomization, mixing, crystal structure conversion, particle shaping and/or particle size uniformization treatment as in the compound (I). may be carried out. It is preferable that the particle diameter of a coloring agent (A1) is substantially uniform. When using a coloring agent (A1), a compound (I), and/or multiple types of derivatives, these treatments may be performed individually, respectively, and these treatments may be mixed and these treatments may be carried out by multiple types.

[0410] The colorant (A1) can be uniformly dispersed in the colorant (A1)-containing liquid by subjecting the colorant (A1) to a dispersion treatment containing a dispersing agent. A coloring agent (A1) may carry out a dispersion process independently, respectively, and may mix and disperse|distribute multiple types.

[0411] Examples of the dispersant include surfactants, and any surfactants selected from cationic, anionic, nonionic and amphoteric surfactants may be used. Specifically, surfactants, such as a polyester type, a polyamine type, and an acryl type, etc. are mentioned. These dispersing agents may be used individually or may be used in combination of 2 or more type. As the dispersing agent, if indicated by a brand name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by KYOEISHA CHEMICAL Co., LTD.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajispa (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), DISPERBYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) ( BYK-Chemie Co., Ltd. product) etc. are mentioned.

[0412] When the colorant (A1)-containing liquid contains a dispersant, the amount of the dispersant (solid content) to be used is, for example, 0.01 parts by mass or more and 10000 parts by mass or less, and preferably 0.01 parts by mass, based on 100 parts by mass of the colorant (A1). They are at least 5000 parts by mass, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, still more preferably 0.1 parts by mass or more and 300 parts by mass or less. , More preferably, they are 1 mass part or more and 300 mass parts or less, Especially preferably, they are 5 mass parts or more and 260 mass parts or less.

When the usage-amount of this dispersing agent exists in said range, there exists a tendency for the coloring agent (A1) containing liquid in a more uniform dispersed state to be obtained.

[0413] After the coloring composition of the present invention contains the resin (B) and the colorant (A1) containing liquid containing the colorant (A1) and the solvent (E) is prepared in advance, the colorant (A1) containing liquid is used , When preparing the coloring composition of this invention, a coloring agent (A1) containing liquid is a part or all of resin (B) contained in a coloring composition, Preferably, it may contain previously a part. By including the resin (B) in advance, the dispersion stability of the colorant (A1)-containing liquid can be further improved.

[0414] When the colorant (A1)-containing liquid contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10000 parts by mass or less, with respect to 100 parts by mass of the colorant (A1), preferably is 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, still more preferably 0.1 parts by mass or more and 300 parts by mass. is below.

[0415] When the coloring composition of the present invention contains the coloring agent (A1), in the coloring composition, the content of the coloring agent (A) in which the compound (I) and the coloring agent (A1) are combined is 100% by mass based on the total amount of solid content. or less, preferably 0.0001 mass% or more and 99.9999 mass% or less, more preferably 0.0001 mass% or more and 99 mass% or less, still more preferably 0.0001 mass% or more and 90 mass% or less, still more preferably 0.0001 mass% or more % or more and 80 mass% or less, more preferably 0.0001 mass% or more and 70 mass% or less, particularly preferably 0.0001 mass% or more and 60 mass% or less, and extremely preferably 0.0001 mass% or more and 55 mass% or less. , Most preferably 0.1 mass % or more and 55 mass % or less.

[0416] When the coloring composition of the present invention contains the coloring agent (A1), the content of the compound (I) is usually 0.0001% by mass or more, preferably 0.0003% by mass or more, in the total amount of the coloring agent (A). , more preferably 0.0005 mass% or more, still more 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, still more preferably Preferably it is 98 mass % or less, More preferably, it is 97 mass % or less.

[0417] [Leveling agent (F)]

As a leveling agent (F), a silicone type surfactant, a fluorine type surfactant, the silicone type surfactant which has a fluorine atom, etc. are mentioned. These may have a polymeric group in a side chain.

[0418] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Dow Corning Toray Co., Ltd.), KP321 , KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) and the like.

[0419] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Limited), Megapac (registered trademark) F142D, Megapac F171, Megapac F172, Megapac F173, Megapac F177, Megapac F183, Megapac F554, Megapac R30, Megapac RS-718-K (manufactured by DIC CORPORATION), eftop (registered trademark) EF301, eftop EF303, eftop EF351, eftop EF352 (Mitsubishi Materials Electronic Chemicals Co., Ltd. manufacture), Suplon (trademark) S381, Sufflon S382, Sufflon SC101, Sufflon SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Genkyusho), and the like.

[0420] Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megapac (registered trademark) R08, Megapac BL20, Megapac F475, Megapac F477, and Megapac F443 (manufactured by DIC CORPORATION).

[0421] When the leveling agent (F) is contained, its content is usually 0.00001 mass% or more and 5 mass% or less, preferably 0.00001 mass% or more and 3 mass% or less, with respect to the total amount of the coloring composition, more preferably Preferably, they are 0.0001 mass % or more and 2 mass % or less, More preferably, they are 0.0001 mass % or more and 1 mass % or less.

When content of a leveling agent (F) exists in said range, the flatness of a color filter can be made favorable.

[0422] [Antioxidant (G)]

From a viewpoint of improving the heat resistance and light resistance of a colorant, it is preferable to use antioxidant individually or in combination of 2 or more types. It will not specifically limit if it is a general antioxidant used industrially as antioxidant, A phenol type antioxidant, phosphorus antioxidant, sulfur type antioxidant, etc. can be used.

[0423] As the phenolic antioxidant, for example, Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], Irganox 1076 (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, BASF Manufactured), 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: benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4 -Hydroxy, C7-C9 branched 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), adecastab AO-80 (adecastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)) Propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro (5,5)undecane, manufactured by ADEKA CORPORATION), Sumilizer BHT (Sumilizer BHT, Sumitomo) Chemical Company, Limited), Sumilizer GA-80 (Sumilizer GA-80, Sumitomo Chemical Company, Limited), Sumilizer GS (Sumilizer GS, Sumitomo Chemical Company, Limited), Cyanox 1790 (Cyanox 1790, CITEC Corporation) manufactured) and vitamin E (Eisai Co., Ltd. manufacture) and the like.

[0424] Examples of the phosphorus-based antioxidant include Irgafos 168 (Irgafos 168: Tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF), Irgafos 12 (Irgafos 12: Tris[2) -[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphin-6-yl]oxy]ethyl]amine, manufactured by BASF), ir Gafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF), ADEKA STAB 329K (made by ADEKA CORPORATION), ADEKA STAB PEP36 ( ADEKA CORPORATION), ADEKA STAB PEP-8 (ADEKA CORPORATION), Sandstab P-EPQ (Clariant), Western 618 (Weston 618, GENERAL ELECTRIC COMPANY), Western 619G (Weston 619G, GENERAL ELECTRIC) COMPANY), Ultranox 626 (Ultranox 626, GENERAL ELECTRIC COMPANY) and Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2 ,4,8,10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphospepine) (manufactured by Sumitomo Chemical Company, Limited);

[0425] Examples of the sulfur-based antioxidant include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and tetrakis[methylene(3-dodecylthio)propionate] and β-alkyl mercaptopropionic acid ester compounds of polyols such as methane.

[0426] [Other ingredients]

The coloring composition of this invention may contain well-known additives in the said technical field, such as a filler, another high molecular compound, an adhesion promoter, an optical stabilizer, and a chain transfer agent, as needed.

As the adhesion promoter, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethyl Toxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3 -Methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2-(aminoethyl)- 3-Aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-( Aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3- Aminopropyltriethoxysilane etc. are mentioned.

[0427] [Method for producing a coloring composition]

The coloring composition of this invention, for example, a compound (I), a solvent (E), and, if necessary, resin (B), a polymeric compound (C), a polymerization initiator (D), a polymerization initiation auxiliary|assistant (D1), It can prepare by mixing a coloring agent (A1), a leveling agent (F), antioxidant (G), and/or another component. Mixing can be performed by a known or customary device or condition.

The compound (I) is mixed with a part or all of the solvent (E) in advance, and the compound (I) is dispersed using a bead mill or the like until the average particle diameter of the compound (I) is about 0.2 µm or less. (I) It is preferable to use it in the state of containing liquid. At this time, you may mix|blend a part or all of the said dispersing agent and resin (B) as needed.

The colorant (A1) is mixed with a part or all of the solvent (E) in advance, and the colorant (A1) is dispersed using a bead mill or the like until the average particle diameter of the colorant (A1) is about 0.2 µm or less. It is preferable to use it in the state of a liquid. At this time, you may mix|blend a part or all of the said dispersing agent and resin (B) as needed.

It is preferable to use compound (I) in the state of the solution (the said solution contained in compound (I) containing liquid) previously dissolved in part or all of a solvent (E). Moreover, it is preferable to filter the said compound (I) containing liquid with the filter whose pore diameter is about 0.01 micrometer or more and 1 micrometer or less.

It is preferable to use the coloring agent (A1) in the state of the solution (the said solution is contained in the coloring agent (A1) containing liquid) previously dissolved in part or all of the solvent (E). Moreover, it is preferable to filter the said coloring agent (A1) containing liquid with the filter whose pore diameters are about 0.01 micrometer or more and 1 micrometer or less.

It is preferable to filter the coloring composition after mixing with the filter whose pore diameters are about 0.01 micrometer or more and 10 micrometers or less.

[0428] [Color filter]

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

A colored coating film can be formed by apply|coating a coloring composition to a board|substrate, removing volatile components, such as a solvent, and drying it. The colored coating film thus formed is included in the color filter of the present invention.

A photolithographic method, an inkjet method, a printing method, etc. are mentioned as a method of forming a coloring pattern. Especially, the photolithographic method is preferable. In the photolithography method, the coloring composition is applied to a substrate, dried to form a coloring composition layer, and then the coloring composition layer is exposed through a photomask to develop. The photolithographic method WHEREIN: The colored coating film which is hardened|cured material of the said coloring composition layer can be formed by not using a photomask at the time of exposure and/or not developing. The colored pattern and colored coating film thus formed are the color filters of the present invention.

The film thickness of the color filter to be produced is not specifically limited, It can adjust suitably according to the objective, a use, etc., For example, it is 0.1-30 micrometers, Preferably it is 0.1-20 micrometers, More preferably, it is 0.5-6 micrometers.

[0429] As the substrate, a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass coated with silica, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicone, the substrate What formed the thin film of aluminum, silver, silver/copper/palladium alloy, etc. on it is used. On these board|substrates, another color filter layer, a resin layer, a transistor, a circuit, etc. may be formed.

[0430] Formation of each color pixel by the photolithography method can be performed in a known or customary apparatus or condition. For example, it can be produced as follows.

First, after apply|coating a coloring composition on a board|substrate, volatile components, such as a solvent, are removed and dried by heat-drying (pre-bake) and/or drying under reduced pressure, and a smooth coloring composition layer is obtained.

Examples of the coating method include a spin coating method, a slit coating method, and a slit-and-spin coating method.

30-120 degreeC is preferable and, as for the temperature in the case of heat-drying, 50-110 degreeC is more preferable. Moreover, as heating time, it is preferable that they are between 10 seconds - 60 minutes, and it is more preferable that they are between 30 seconds - 30 minutes. When drying under reduced pressure, it is preferable to carry out under a pressure of 50 to 150 Pa at a temperature range of 20 to 25°C. The film thickness of a coloring composition layer is not specifically limited, What is necessary is just to select suitably according to the film thickness of the color filter made into the objective.

[0431] Next, the coloring composition layer is exposed through a photomask for forming a desired coloring pattern.

The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. As a light source used for exposure, the light source which generate|occur|produces the light whose wavelength is 250-450 nm is preferable. For example, light of less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, or 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. . Specific examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.

It is preferable to use an exposure apparatus such as a mask aligner and a stepper because it is possible to uniformly irradiate parallel rays to the entire exposure surface and to perform accurate alignment between the photomask and the substrate on which the coloring composition layer is formed. do.

[0432] A colored pattern is formed on the substrate by developing the colored composition layer after exposure in contact with a developer. By image development, the unexposed part of a coloring composition layer melt|dissolves in a developing solution, and is removed.

As a developing solution, aqueous solutions of alkaline compounds, such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, and tetramethylammonium hydroxide, are preferable, for example.

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

Any of a puddle method, a dipping method, a spray method, etc. may be sufficient as the image development method. In addition, you may incline a board|substrate at arbitrary angles at the time of development.

It is preferable that the board|substrate after image development is washed with water.

Moreover, it is preferable to post-bake to the obtained coloring pattern.

150-250 degreeC is preferable and, as for post-baking temperature, 160-235 degreeC is more preferable. 1 to 120 minutes is preferable, and, as for post-baking time, between 10 to 60 minutes is more preferable. Thus, in order to provide various characteristics, the color filter which is the obtained coloring pattern and a colored coating film, you may apply to a surface coating process further.

[0433] The color filter is useful as a color filter used in a display device (eg, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor, and among them, a color filter used in a liquid crystal display device.

[0434] This application claims the benefit of priority based on Japanese Patent Application No. 2019-068656 filed on March 29, 2019. All the content of the specification of Japanese Patent Application No. 2019-068656 for which it applied on March 29, 2019 is taken in here for reference.

[Example]

[0435] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples from the beginning, and changes may be made as appropriate within a range suitable for the purpose of the above and later. It is, of course, also possible to implement in addition, all of these are included in the technical scope of the present invention. In addition, in the following, unless otherwise indicated, "part" means "part by mass" and "%" means "mass %".

[0436] In the following synthesis examples, the structure of the compound was confirmed by mass spectrometry (LC; manufactured by Agilent Technologies, Inc., type 1200, MASS; manufactured by Agilent Technologies, Inc., type LC/MSD 6130).

[0437] The polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC method under the following conditions.

Device: HLC-8120GPC (manufactured by TOSOH CORPORATION)

Column: TSK-GELG2000HXL

Column temperature: 40 degrees Celsius

Solvent: tetrahydrofuran

Flow rate: 1.0 mL/min

Solid content concentration of analysis sample: 0.001 to 0.01 mass %

Injection volume: 50 μL

Detector: RI

Standard materials for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by TOSOH CORPORATION)

The ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight (Mw) and the number average molecular weight (Mn) obtained above was made into dispersion degree.

[0438] Example 1

Benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.72 parts, 8-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.00 parts, 4-phenylethynylphthalic anhydride (Tokyo Chemical Industry Co., Ltd.) , Ltd.) 6.92 parts and methyl benzoate (made by Tokyo Chemical Industry Co., Ltd.) 40.4 parts were mixed.

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

To this mixture, 7.83 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was added.

The mixture was stirred for 7 hours while maintaining at 170°C.

To this mixture, 3.19 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 8.97 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added.

The mixture was stirred for 17 hours while maintaining at 170°C.

To this mixture, 7.76 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.17 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) Preparation) 6.17 parts were added.

The mixture was stirred for 19 hours while maintaining at 170°C.

The mixture was cooled to room temperature, and to this mixture, 420 parts of methanol was added and stirred for 1 hour.

The mixture was filtered, and the obtained residue was washed 6 times with 120 parts of methanol.

The obtained residue was dried under reduced pressure at 60 DEG C to obtain 7.23 parts of the compound represented by the formula (Ia3).

[0439]

[0440] <Identification of the compound represented by the formula (Ia3)>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 619

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-H] ^- 617

Exact Mass: 618

[0441] Synthesis Example 1

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was poured into the flask, replaced with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was placed, and the mixture was heated to 80°C while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylic A mixed solution of 289 parts and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution obtained 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 completion|finish of dripping, after hold|maintaining at 80 degreeC for 4 hours, it cooled to room temperature, and obtained the copolymer (resin B1) solution of 35.0% of solid content. The weight average molecular weight of obtained resin B1 was 80 mg-KOH/g in 8800, dispersion degree, and the acid value in conversion of solid content of 2.1.

[0442] Synthesis Example 2

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was poured into the flask, replaced with a nitrogen atmosphere, 340 parts of propylene glycol monomethyl ether acetate was placed, and the mixture was heated to 80°C while stirring. Subsequently, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylic A mixed solution of 54 parts of a mixture (content ratio of 1:1), 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 obtained 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 completion|finish of dripping, after hold|maintaining at 80 degreeC for 3 hours, it cooled to room temperature, and obtained the copolymer (resin B2) solution of 36.8% of solid content. The weight average molecular weight of the obtained resin B2 was 9400, the dispersion degree was 1.89, and the acid value in conversion of solid content was 114 mg-KOH/g.

[0443] Example 2

Each component was mixed in the following ratios, the coloring agent was disperse|distributed using the bead mill, and the coloring composition M1 was obtained.

Coloring agent (A): 4.50 parts of compound represented by Formula (Ia3);

Coloring agent (A): 0.500 part of compound represented by Formula (z);

Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK JAPAN KK);

Resin (B): 11.4 parts of resin B1 solution;

Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate;

Solvent (E): 20.0 parts of ethyl lactate;

[0444] Next, each component was mixed in the following proportions to obtain a colored composition 1.

57.6 parts of coloring composition M1;

Resin (B): 27.0 parts of resin B2 solution;

Solvent (E): 15.4 parts of propylene glycol monomethyl ether acetate;

Leveling agent (F): 0.00630 parts of Toray silicone SH8400 (made by Dow Corning Toray Co., Ltd.);

[0445]

[0446] On a 2 inch square glass substrate (Eagle XG; manufactured by Corning Incorporated), the coloring composition 1 was applied by spin coating, and then pre-baked at 100° C. for 3 minutes, pre-baked colored coating film was formed.

The film thickness of the obtained prebaked colored coating film was measured using DektakXT (made by BRUKER).

The spectrum of this prebaked colored coating film was measured using the colorimeter:LVmicroZ (made by Lambda Vision Inc.).

Table 31 shows the maximum absorption wavelength on the longest wavelength side of the film thickness of this prebaked colored coating film and the absorption spectrum of this prebaked colored coating film.

With respect to this pre-baked colored coating film, the post-baking colored coating film was obtained by performing post-baking at 230 degreeC for 30 minutes.

[0447] Comparative Example 1

Each component was mixed in the following ratios, the coloring agent was disperse|distributed using the bead mill, and the coloring composition M2 was obtained.

Colorant (A): C.I. Pigment Yellow 138 12.0 parts;

4.21 parts solids of dispersant;

5.05 parts of resin solids;

Solvent (E): 74.8 parts of propylene glycol monomethyl ether acetate;

Solvent (E): 3.94 parts of propylene glycol monomethyl ether;

Then, each component was mixed in the following proportions to obtain a coloring composition 2.

24.0 parts of coloring composition M2;

Resin (B): 35.0 parts of resin B2 solution;

Solvent (E): 41.0 parts of propylene glycol monomethyl ether acetate;

Leveling agent (F): 0.00630 parts of Toray silicone SH8400 (made by Dow Corning Toray Co., Ltd.);

[0449] On a 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated), the coloring composition 2 was applied by spin coating, and then pre-baked at 100° C. for 3 minutes to form a pre-baked colored coating film.

The film thickness of the obtained prebaked colored coating film was measured using DektakXT (made by BRUKER).

The spectrum of this prebaked colored coating film was measured using the colorimeter:LVmicroZ (made by Lambda Vision Inc.).

Table 31 shows the maximum absorption wavelength on the longest wavelength side of the film thickness of this prebaked colored coating film and the absorption spectrum of this prebaked colored coating film.

With respect to this pre-baked colored coating film, the post-baking colored coating film was obtained by performing post-baking at 230 degreeC for 30 minutes.

[0450] Comparative Example 2

Each component was mixed in the following ratios, the coloring agent was disperse|distributed using the bead mill, and the coloring composition M3 was obtained.

Colorant (A): C.I. Pigment Yellow 138 4.50 parts;

Coloring agent (A): 0.500 part of compound represented by Formula (z);

Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK JAPAN KK);

Resin (B): 11.4 parts of resin B1 solution;

Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate;

Solvent (E): 20.0 parts of ethyl lactate;

[0451] Then, each component was mixed in the following proportions to obtain a colored composition 3.

57.6 parts of coloring composition M3;

Resin (B): 27.0 parts of resin B2 solution;

Solvent (E): 15.4 parts of propylene glycol monomethyl ether acetate;

Leveling agent (F): 0.00630 parts of Toray silicone SH8400 (made by Dow Corning Toray Co., Ltd.);

[0452] On a 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated), the coloring composition 3 was applied by spin coating and then pre-baked at 100° C. for 3 minutes to form a pre-baked colored coating film.

The film thickness of the obtained prebaked colored coating film was measured using DektakXT (made by BRUKER).

The spectrum of this prebaked colored coating film was measured using the colorimeter:LVmicroZ (made by Lambda Vision Inc.).

Table 31 shows the maximum absorption wavelength on the longest wavelength side of the film thickness of this prebaked colored coating film and the absorption spectrum of this prebaked colored coating film.

With respect to this pre-baked colored coating film, the post-baking colored coating film was obtained by performing post-baking at 230 degreeC for 30 minutes.

[0453] In Table 31,

The "AAA" column shows the maximum absorption wavelength of the longest wavelength side of an absorption spectrum, and the "BBB" column shows the wavelength of the shoulder peak of the longest wavelength side of an absorption spectrum.

[0454] [Table 31]

[0455] From the above results, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing the compound of the present invention or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum is C.I. It turned out that it is a longer wavelength compared with the maximum absorption wavelength of the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing Pigment Yellow 138.

[Industrial Applicability]

[0456] The coloring composition and compound of the present invention, C.I. Compared with the coloring composition containing Pigment Yellow 138, since it can use for formation of the color filter of a darker color, it is used suitably for display apparatuses, such as a color filter and a liquid crystal display device.

Claims (6)

The coloring composition containing the compound and solvent represented by following formula (I).

[In formula (I),
R ¹ to ^{R 5} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or Represents a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
The hydrogen atom constituting the monovalent hydrocarbon 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 ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ may be respectively 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} each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
The hydrogen atom constituting the monovalent hydrocarbon 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.}
Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
Even if the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.
However, ^{at least one of Q 1} and Q ² has a group represented by the formula (y).

Y ¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
The hydrogen atom constituting the monovalent hydrocarbon 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.}
※ indicates a bonding hand (結合手).
When two or more Z ^{1 to Z 4} , the group represented by the formula (y), Y ¹ , M and MM each exist, they may be the same as or different from each other.] According to claim 1,
A coloring composition comprising a resin. 3. The method of claim 1 or 2,
A coloring composition comprising a polymerizable compound and a polymerization initiator. The color filter formed with the coloring composition in any one of Claims 1-3. A display device comprising the color filter according to claim 4 . A compound represented by formula (I).

[In formula (I),
R ¹ to ^{R 5} are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent hydrocarbon group having 1 to 40 carbon atoms represents a monovalent heterocyclic group,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
The hydrogen atom constituting the monovalent hydrocarbon 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 ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ may be respectively 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} each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
The hydrogen atom constituting the monovalent hydrocarbon 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.}
Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
Even if the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM or a group represented by the formula (y), do.
However, ^{at least one of Q 1} and Q ² has a group represented by the formula (y).

Y ¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-;
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N=;
_{-CH 2} - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) _{2 - or -CO-;}
The hydrogen atom constituting the monovalent hydrocarbon 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.}
※ indicates a bonding hand.
When two or more Z ^{1 to Z 4} , the group represented by the formula (y), Y ¹ , M and MM each exist, they may be the same as or different from each other.]