WO2020203514A1 - 着色組成物、化合物、カラーフィルタ及び表示装置 - Google Patents
着色組成物、化合物、カラーフィルタ及び表示装置 Download PDFInfo
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- WO2020203514A1 WO2020203514A1 PCT/JP2020/013196 JP2020013196W WO2020203514A1 WO 2020203514 A1 WO2020203514 A1 WO 2020203514A1 JP 2020013196 W JP2020013196 W JP 2020013196W WO 2020203514 A1 WO2020203514 A1 WO 2020203514A1
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- 0 *C(N(C(*)=O)c1c2nc(C(C(*3)=O)C3=O)c(*)c(*)c2c(*)c(*)c1*)=O Chemical compound *C(N(C(*)=O)c1c2nc(C(C(*3)=O)C3=O)c(*)c(*)c2c(*)c(*)c1*)=O 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Nc1ccccc1 Chemical compound Nc1ccccc1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- FRMZDRRTPXFMGQ-UHFFFAOYSA-N O=C(C1c(ccc2ccc3)nc2c3N(C(c(cc2)c3cc2C#Cc2ccccc2)=O)C3=O)c(ccc(C#Cc2ccccc2)c2)c2C1=O Chemical compound O=C(C1c(ccc2ccc3)nc2c3N(C(c(cc2)c3cc2C#Cc2ccccc2)=O)C3=O)c(ccc(C#Cc2ccccc2)c2)c2C1=O FRMZDRRTPXFMGQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B25/00—Quinophthalones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Definitions
- the present invention relates to coloring compositions, compounds, color filters and display devices.
- the coloring composition is used in the manufacture of color filters used in display devices such as liquid crystal display devices and electroluminescence display devices.
- Examples of the colorant contained in the coloring composition include C.I. I. Pigment Yellow 138 is known (Patent Document 1). (CI Pigment Yellow 138)
- the conventionally known C.I. I. Pigment Yellow 138 has a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum on the long wavelength side of the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and / or a shoulder peak on the longest wavelength side of the absorption spectrum.
- a coloring composition containing a compound having a wavelength of is required. What is the wavelength of the shoulder peak on the longest wavelength side of the above absorption spectrum? The compound is ⁇ C. I.
- Pigment Yellow 138 has no maximum absorption wavelength on the longest wavelength side of the absorption spectrum on the long wavelength side of the maximum absorption wavelength on the longest wavelength side of the absorption spectrum. And, -When there are two or more inflection points of the absorption spectrum on the long wavelength side of 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 on the longest wavelength side of the absorption spectrum and the wavelength of the inflection point on the second longest wavelength side of the absorption spectrum.
- a coloring composition containing a compound represented by the following formula (I) and a solvent [In formula (I), R 1 to R 5 are independently hydrogen atom, halogen atom, cyano group, nitro group, -SO 3 M, -CO 2 M, MM, monovalent hydrocarbon group or carbon having 1 to 40 carbon atoms. Represents a monovalent heterocyclic group of the numbers 1-40 The -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced 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 coupled to each other to form a ring.
- M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N (Z 1 ) (Z 2 ) (Z 3 ) (Z 4 ).
- MM represents an alkali metal atom, a metal atom which may have a ligand, or N (Z 1 ) (Z 2 ) (Z 3 ) (Z 4 ).
- Z 1 to Z 4 independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- Q 1 and Q 2 independently represent a divalent hydrocarbon group or a divalent heterocyclic group, respectively.
- the -C (-) (-)-constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N (-)-.
- the divalent hydrocarbon group and -CH 2- constituting the divalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the divalent hydrocarbon group and the hydrogen atom constituting the divalent heterocyclic group are represented by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM or the formula (y). It may be replaced with a base. However, at least one of Q 1 and Q 2 has a group represented by the formula (y).
- Y 1 is 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.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. * Indicates a joint hand. When there are a plurality of Z 1 to Z 4 , groups represented by the formula (y), Y 1 , M and MM, they may be the same or different from each other.
- [2] The coloring composition according to [1], which contains a resin. [3] The coloring composition according to [1] or [2], which contains a polymerizable compound and a polymerization initiator. [4] A color filter formed by the coloring composition according to any one of [1] to [3]. [5] A display device including the color filter according to [4]. [6] A compound represented by the formula (I). [In formula (I), R 1 to R 5 are independently hydrogen atom, halogen atom, cyano group, nitro group, -SO 3 M, -CO 2 M, MM, and 1 of 1 to 40 carbon atoms. Represents a valent hydrocarbon group or a monovalent heterocyclic group having 1 to 40 carbon atoms.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced 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 , respectively, may be coupled to each other to form a ring.
- M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N (Z 1 ) (Z 2 ) (Z 3 ) (Z 4 ).
- MM represents an alkali metal atom, a metal atom which may have a ligand, or N (Z 1 ) (Z 2 ) (Z 3 ) (Z 4 ).
- Z 1 to Z 4 independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- Q 1 and Q 2 independently represent a divalent hydrocarbon group or a divalent heterocyclic group, respectively.
- the -C (-) (-)-constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N (-)-.
- the divalent hydrocarbon group and -CH 2- constituting the divalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the divalent hydrocarbon group and the hydrogen atom constituting the divalent heterocyclic group are represented by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM or the formula (y). It may be replaced with a base. However, at least one of Q 1 and Q 2 has a group represented by the formula (y).
- Y 1 is 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.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. * Indicates a joint hand. When there are a plurality of Z 1 to Z 4 , groups represented by the formula (y), Y 1 , M and MM, they may be the same or different from each other. ]
- coloring compositions and compounds that can be used to form darker color filters as compared to coloring compositions containing Pigment Yellow 138.
- the coloring composition of the present invention contains a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) and a solvent (hereinafter, may be referred to as solvent (E)).
- R 1 to R 5 are independently hydrogen atom, halogen atom, cyano group, nitro group, -SO 3 M, -CO 2 M, MM, monovalent hydrocarbon group or carbon having 1 to 40 carbon atoms. Represents a monovalent heterocyclic group of the numbers 1-40 The -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced 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 coupled to each other to form a ring.
- M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N (Z 1 ) (Z 2 ) (Z 3 ) (Z 4 ).
- MM represents an alkali metal atom, a metal atom which may have a ligand, or N (Z 1 ) (Z 2 ) (Z 3 ) (Z 4 ).
- Z 1 to Z 4 independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- Q 1 and Q 2 independently represent a divalent hydrocarbon group or a divalent heterocyclic group, respectively.
- the -C (-) (-)-constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N (-)-.
- the divalent hydrocarbon group and -CH 2- constituting the divalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the divalent hydrocarbon group and the hydrogen atom constituting the divalent heterocyclic group are represented by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM or the formula (y). It may be replaced with a base. However, at least one of Q 1 and Q 2 has a group represented by the formula (y).
- Y 1 is 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.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. * Indicates a joint hand. When there are a plurality of Z 1 to Z 4 , groups represented by the formula (y), Y 1 , M and MM, they may be the same or different from each other. ]
- Compound (I) also includes its tautomers and salts thereof.
- Compound (I) can be used as a colorant.
- the coloring composition of the present invention may contain one or more compounds (I).
- the coloring composition of the present invention may contain a resin (hereinafter, may be referred to as a resin (B)).
- the coloring composition of the present invention may contain a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)).
- the coloring composition of the present invention may contain a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)).
- the coloring composition of the present invention may contain a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D1)).
- a coloring agent other than the compound (I) (hereinafter, may be referred to as a coloring agent (A1).
- the compound (I) and the coloring agent (A1) are referred to as “coloring agent (A)). ”) May be included.
- the colorant (A1) may contain one or more colorants.
- the colorant (A1) preferably contains one or more selected from a yellow colorant, an orange colorant, a red colorant, and a green colorant.
- the coloring composition of the present invention may contain a leveling agent (hereinafter, may be referred to as a leveling agent (F)).
- the coloring composition of the present invention may contain an antioxidant (hereinafter, may be referred to as an antioxidant (G)).
- halogen atom examples 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.
- the hydrocarbon groups represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 have 1 to 40 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 20 carbon atoms. Is 1 to 18, and particularly preferably 1 to 12.
- the monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
- the aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-shaped (chain hydrocarbon group) or cyclic (aliphatic hydrocarbon group).
- Saturated or unsaturated chain hydrocarbon groups represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and heptyl group.
- Octyl group nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecil group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl Group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentoriacontyl group, dotriacyl group, tritoriacontyl group, tetratriacontyl group, pentatriacontyl group, hexatriacontyl group , Heptatriacontyl group, octatriacontyl group,
- the number of carbon atoms of the saturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 18, and particularly preferably 1 to 12.
- the unsaturated chain hydrocarbon group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, still more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. Of these, a linear or branched alkyl group having 1 to 12 carbon atoms is particularly preferable.
- Saturated or unsaturated alicyclic hydrocarbon groups represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
- Cycloheptyl group 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethyl Cyclohexyl 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
- the saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, further preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms.
- a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group are particularly preferable.
- 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, an o-tolyl group, an m-tolyl group, a p-tolyl group, and a 2-ethylphenyl group.
- 3-ethylphenyl 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-
- the hydrocarbon groups represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 are the above-mentioned hydrocarbon groups (for example, aromatic hydrocarbon groups, chain hydrocarbon groups and alicyclic hydrocarbons). It may be a group in which at least one of the groups) is combined, and it may be a benzyl group, a (2-methylphenyl) methyl group, a (3-methylphenyl) methyl group, a (4-methylphenyl) methyl group, or (2-ethyl).
- 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,
- the groups represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 are a combination of the above-mentioned hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group), for example. Cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, (2-methylcyclohexyl) methyl group, cyclohexylethyl group, adamantylmethyl group, etc. It may be an alkyl group to which one or more alicyclic hydrocarbon groups are bonded. These carbon atoms are preferably 4 to 30, more preferably 4 to 20, still more preferably 4 to 18, and particularly preferably 4 to 12.
- the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R 1 to R 5 , 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.
- Examples of the hetero atom include a nitrogen atom, an oxygen atom and a sulfur atom.
- the number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 20, still more preferably 3 to 18, and particularly preferably 3 to 12.
- Monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; Pyrrole, 1-methylpyrrole, pyrrole such as 2,5-dimethylpyrrole, pyrazole, 1-methylpyrazole, 2-methylpyrazole, 3-methylpyrazole, 4-methylpyrazole, 5-methylpyrazole and other pyrazole, imidazole, 1 , 2,3-Triazole and 1,2,4-Triazole, etc., 5-membered ring-based unsaturated heterocycle; Pyrimidines such as pyridine, pyridazine, pyridimine, 6-methylpyrimidine, pyrazines and 6-membered ring unsaturated heterocycles such as 1,3,5-triazine; Indazole, indolin, isoindoline, indole, indolidin, benzoimidazole, quinoline, isoquinoline,
- Monocyclic saturated heterocycles such as oxylane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxolane, 2-cyclopentyldioxolane; Bicyclic saturated heterocycles such as 1,4-dioxaspiro [4.5] decane, 1,4-dioxaspiro [4.5] nonane, 1,4-dioxaspiro [4.4] nonane; Lactone-based heterocycles such as ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -valerolactone and ⁇ -valerolactone; A 5-membered ring-based unsaturated heterocycle such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran and the like; 6-membere
- heterocycle containing a sulfur atom 5-membered ring-based saturated heterocycle such as dithiolane; 6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, 2-methyl-1,3-dithiane; Thiophene such as thiophene, 3-methylthiophene, 2-carboxythiophene, 2H-thiopyran, thiopyran such as 4H-thiopyran, 5-membered ring system unsaturated heterocycle such as benzothiopyran such as benzotetrahydrothiopyran, and 6-membered ring system unsaturated Heterocycle; Benzodiazepines such as benzothiopyran and benzotetrahydrothiopyran, condensed bicyclic heterocycles such as benzothiophene, etc.; Condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.
- Monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone and 2-methyl-2-piperidone; Monocyclic unsaturated heterocycles such as oxazole, 4-methyloxazole and other oxazoles, 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, 5-methylisoxazole and other isooxazole; Condensed bicyclic heterocycles such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxan, benzoimidazoline; Condensation tricyclic heterocycles such as phenoxazine; and the like.
- heterocycle containing a nitrogen atom and a sulfur atom Monocyclic heterocycles such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole, 2,4-dimethylthiazole and the like; Condensation bicyclic heterocycles such as benzothiazole; Condensation tricyclic heterocycles such as phenothiazine; and the like.
- the binding site of the above heterocyclic group is a portion where an arbitrary hydrogen atom contained in each heterocycle is eliminated.
- the heterocyclic group may be a group in which the above-mentioned heterocycle and the above-mentioned hydrocarbon group (preferably one or both of an aliphatic hydrocarbon group and an aromatic hydrocarbon group) are combined, for example. , Tetrahydrofurylmethyl group;
- Phthalic anhydride derivatives such as; And so on. * Indicates a joint hand.
- heterocyclic group may be represented by the following formula. * Indicates a joint hand.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- a halogen atom e.g., a fluoride
- a cyano group e.g., a cyano group
- a nitro group e.g., -SO 3 M, -CO 2 M or MM.
- 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-trifluoromethyl-1-phenylethyl Group, (phenoxy) (phenyl) methyl group, (benzyloxy) (phenyl) methyl group, pyrrolyl
- An aryl group having a substituent such as a -1-naphthyl group, a 4,5,8-trichloro-2-naphthyl group, an anthraquinonyl group, a 2-aminoanthraquinonyl group (hereinafter, these may be referred to as a group B group).
- formyl group acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, 2-ethylhexanoyl group, heptanoil group, octanoyl group, nonanoyl group, decanoyyl group, undecanoyl group, Dodecanoyl group, Henikosanoyl group, Benzoyl group,
- 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 can be mentioned.
- a carbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a preferred monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is preferable.
- a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is more preferable.
- a carbonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is further preferable.
- a carbonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or a preferred monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is particularly preferable. * Indicates a joint hand.
- methoxycarbonyl group ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethylhexyl) oxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group.
- An oxycarbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a preferable monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is preferable. More preferably, an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is preferable.
- An oxycarbonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is further preferable.
- An oxycarbonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of groups A to B described above, or a monovalent hydrocarbon group described above or a monovalent heterocyclic group preferably bonded is particularly preferable. * Indicates a joint hand.
- formyloxy group acetoxy group, propanoyloxy group, butanoyloxy group, (2,2-dimethylpropanoyl) oxy group, pentanoyloxy group, hexanoyloxy group, (2-ethylhexanoyl) oxy group, Heptanoyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, (2-propenyl) )
- a carbonyloxy group, a (1-methylethenyl) carbonyloxy group, and a carbonyloxy group to which the above groups A to B or the above monovalent hydrocarbon group or monovalent heterocyclic group are bonded can be mentioned.
- a carbonyloxy group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a preferable monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is preferable. More preferably, a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is preferable. A carbonyloxy group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is further preferable. A carbonyloxy group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of groups A to B described above, or a monovalent hydrocarbon group described above or a monovalent heterocyclic group preferably bonded is particularly preferable.
- a hydrocarbon group having 1 to 30 carbon atoms, an oxy group or a hydroxy group to which a preferable group of the above groups A to B or the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded is preferable. More preferably, an oxy group or a hydroxy group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is more preferable.
- an oxy group or a hydroxy group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is more preferable.
- a hydrocarbon group having 1 to 12 carbon atoms, an oxy group to which a preferred group of the above groups A to B or a preferred monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is particularly preferable. * Indicates a joint hand.
- 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, icosilthio group, phenylthio group, o-tolylthio group, Examples thereof include a mercapto group in which a hydrogen atom is replaced with the above-mentioned group A to B group or the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group.
- methylsulfonyl group ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethylhexyl) sulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, un Decylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group,
- the above-mentioned groups A to B the above-mentioned monovalent hydrocarbon group, the sulfonyl group to which the above-mentioned monovalent hetero
- a sulfonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a preferred monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is preferable.
- a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is more preferable.
- a sulfonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is further preferable.
- a sulfonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of groups A to B described above, or a monovalent hydrocarbon group described above or a monovalent heterocyclic group preferably bonded is particularly preferable. * Indicates a joint hand.
- 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-pentyl sulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N-hexyl sulfamoyl group, N- (2-) Ethylhexyl) sulfamoyl group, N-heptyl sulfamoyl group, N-octyl sulfamoyl group, N-nony
- Substituted sulfamoyl groups, —SO 2 NH (CH 2 ) 2 N (CH 2 CH 3 ) 2 or sulfamoyl groups are preferred.
- Substituted sulfamoyl groups —SO 2 NH (CH 2 ) 2 N (CH 2 CH 3 ) 2 or sulfamoyl groups are more preferred.
- Substituted sulfamoyl groups, —SO 2 NH (CH 2 ) 2 N (CH 2 CH 3 ) 2 or sulfamoyl groups are more preferred.
- Substituted sulfamoyl groups, —SO 2 NH (CH 2 ) 2 N (CH 2 CH 3 ) 2 or sulfamoyl groups are particularly preferred.
- Carbamic 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-undecyl
- Substituted carbamoyl groups or carbamoyl groups are more preferred One or two selected from the above-mentioned preferred ones of hydrocarbon groups having 1 to 18 carbon atoms, the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups, and the above-mentioned monovalent heterocyclic groups. Substituted carbamoyl groups or carbamoyl groups are more preferred. One or two selected from the above-mentioned preferred hydrocarbon groups having 1 to 12 carbon atoms, the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups, and the above-mentioned monovalent heterocyclic groups. Substituted carbamoyl groups or carbamoyl groups are particularly preferred.
- 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 groups A to B above or monovalent above. Amino group in which one hydrocarbon group or monovalent heterocyclic group is substitute
- Substituted amino groups or amino groups are preferred One or two selected from the above-mentioned preferred hydrocarbon groups having 1 to 20 carbon atoms, the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups, and the above-mentioned monovalent heterocyclic groups.
- Substituted amino groups or amino groups are more preferred One or two selected from the above-mentioned preferred ones of hydrocarbon groups having 1 to 18 carbon atoms, the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups, and the above-mentioned monovalent heterocyclic groups. Substituted amino groups, or amino groups, are more preferred. One or two selected from the above-mentioned preferred ones of hydrocarbon groups having 1 to 12 carbon atoms, the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups, and the above-mentioned monovalent heterocyclic groups. Substituted amino groups or amino groups are particularly preferred.
- formylamino group For example, formylamino group; acetylamino group, propanoylamino group, butanoylamino group, (2,2-dimethylpropanoyl) amino group, pentanoylamino group, hexanoylamino group, (2-ethylhexanoyl) amino.
- a carbonylamino group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a preferred monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is preferable.
- a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is more preferable.
- a carbonylamino group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a preferable one of the above monovalent hydrocarbon group or the above monovalent heterocyclic group is bonded is further preferable.
- a carbonylamino group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of groups A to B described above, or a monovalent hydrocarbon group described above or a monovalent heterocyclic group preferably bonded is particularly preferable. * Indicates a joint hand.
- -SiH 3 , -Si (OH) 3 , -SiH (OH) 2 and -SiH 2 (OH), or -Si (OH) 3 substituted with three are preferable.
- -SiH 3 , -Si (OH) 3 , -SiH (OH) 2 and -SiH 2 (OH), or -Si (OH) 3 substituted with three are more preferable.
- -SiH 3 , -Si (OH) 3 , -SiH (OH) 2 and -SiH 2 (OH), or -Si (OH) 3 substituted with three are more preferable.
- hydrocarbon groups having 1 to 12 carbon atoms One or two selected from the above-mentioned preferred ones of hydrocarbon groups having 1 to 12 carbon atoms, the above-mentioned groups A to B, the above-mentioned monovalent hydrocarbon groups, and the above-mentioned monovalent heterocyclic groups.
- -SiH 3 , -Si (OH) 3 , -SiH (OH) 2 and -SiH 2 (OH), or -Si (OH) 3 substituted with three are particularly preferable.
- a phthalimidomethyl group (C 6 H 4 (CO) 2 N-CH 2- ) which may have a substituent
- substituent include the above halogen atoms and the above groups A to B.
- At least one selected from the group consisting of a group, the above-mentioned monovalent hydrocarbon group, the above-mentioned monovalent heterocyclic group and the like can be mentioned.
- the monovalent hydrocarbon group or the monovalent heterocyclic group includes -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.
- R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may be coupled to each other to form a ring.
- alkali metal atom represented by M and MM examples include alkali metal atoms such as lithium atom, sodium atom and potassium atom.
- Examples of the metal atom of the metal atom which may have a ligand represented by M and MM include a metal atom belonging to groups 2 to 15 of the periodic table of elements.
- the metal atom of the metal atom which may have a ligand is 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, It is Cr, and particularly preferably Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al and Cr.
- the ligand of the metal atom which may have a ligand is not particularly limited, and may be, for example, a halogen atom, NO, NO 3 , SO 4 , CH 3 CO 2 , OH or the like.
- the ligand coordinated to the metal atom and the carbon atom, nitrogen atom, oxygen atom, sulfur atom and the like contained in the same ligand may be coordinated to the same metal atom.
- a plurality of different ligands may be coordinated to the same metal atom at the metal atom, or an oligomer or a polymer may be formed.
- the ligand also contains a compound (I) excluding the metal atom which may have a ligand.
- the compound (I) of the present invention also contains such an oligomer or polymer. However, the charge of compound (I) is zero.
- Examples of such compound (I) include metal salts represented by the following formulas (EN1) to (EN5). However, in the formulas (EN1) to (EN5), it is shown that the structures shown in () are repeatedly bonded like oligomers and polymers.
- the metal salt represented by the formula (EN1) indicates that the same ligand is coordinated to the same metal atom.
- the metal salts represented by the formulas (EN2) to (EN3) indicate that a plurality of different ligands are coordinated to the same metal atom.
- 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.
- M is Hydrogen atom; Alkali metal atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination.
- Ni which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand.
- Co which may have, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, and has 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 ); 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 ) A group in which NH 4 such as 2 is substituted with four alkyl groups is preferable.
- Hydrogen atom Sodium atom, potassium atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination.
- Ni which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand.
- Co which may have, 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 ); 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 four alkyl groups are substituted for NH 4 such as (CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 is more preferable.
- MM is Alkali metal atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination. Ni which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand. Co which may have, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, and has 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 ); 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 ) A group in which NH 4 such as 2 is substituted with four alkyl groups is preferable.
- Co which may have, 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 ); 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 four alkyl groups are substituted for NH 4 such as (CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 is more preferable.
- Q 1 and Q 2 independently represent a divalent hydrocarbon group or a divalent heterocyclic group, respectively.
- the -C (-) (-)-constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N (-)-.
- the divalent hydrocarbon group and -CH 2- constituting the divalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the divalent hydrocarbon group and the hydrogen atom constituting the divalent heterocyclic group are represented by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM or the formula (y). It may be replaced with a base. However, at least one of Q 1 and Q 2 has a group represented by the formula (y).
- Y 1 is 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.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. * Indicates a joint hand.
- the divalent hydrocarbon group and the group that replaces the hydrogen atom constituting the divalent heterocyclic group are represented by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or the formula (y).
- the group may be a halogen atom, a cyano group, a nitro group, -SO 3 H, -CO 2 H, or a group represented by the formula (y).
- Q 1 has a group represented by the formula (y) and Q 2 has a group represented by the formula (y).
- Q 1 and Q 2 may be different may be the same, it is preferably the same.
- Q 1 and Q 2 are preferably groups represented by the formulas (QQ1) to (QQ19).
- R Q1 to R Q94 are independently hydrogen atom, halogen atom, cyano group, nitro group, -SO 3 M, -CO 2 M, MM, group represented by formula (y), and carbon number 1 to 1.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the monovalent hydrocarbon group and the hydrogen atom constituting the monovalent heterocyclic group are represented by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM or the formula (y). It may be replaced with a base.
- R Q1 ⁇ R Q94 is may form a ring by combining with one or more, each selected from R Q1 ⁇ R Q94 each other.
- 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 joint hand. ]
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. The same can be mentioned.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the monovalent hydrocarbon group and the hydrogen atom constituting the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- It is a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 .
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. The same ones as preferred are mentioned.
- R Q1 to R Q94 include the same preferable ones of 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).
- Q 1 and Q 2 It is preferably a group represented by the formulas (QQ1) to (QQ12). More preferably, it is a group represented by the formulas (QQ1) to (QQ5). It is more preferable that the group is represented by the formulas (QQ1) to (QQ4).
- the group represented by the formula (QQ1) and the formula (QQ2) is particularly preferable, and the group represented by the formula (QQ1) is more preferable.
- Examples of the formulas (QQ1) to (QQ19) include the following formulas (Qa1) to formula (Qa50); formulas (Qb1) to formulas (Qb27); formulas (Qc1) to formulas (Qc56); formulas (Qd1).
- the compound represented by the formula (I) is preferably a compound represented by the formula (I') (hereinafter, may be referred to as a compound (I')).
- R 1 to R 5 have the same meanings as described above.
- R 6 to R 13 are independently hydrogen atom, halogen atom, cyano group, nitro group, -SO 3 M, -CO 2 M, MM, group represented by the formula (y), and carbon number 1 to 1.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. Even if 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 , respectively, are coupled to each other to form a ring. Good. However, at least one of R 6 to R 13 is a group represented by the formula (y). ]
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. The same can be mentioned.
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the monovalent hydrocarbon group and the hydrogen atom constituting the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM.
- It is a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by R 1 to R 5 , Z 1 to Z 4 and Y 1 .
- the -C (-) (-)-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si (-) (-)-.
- the -CH (-)-that constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N (-)-.
- the monovalent hydrocarbon group and -CH 2- constituting the monovalent heterocyclic group may be replaced with -O-, -S-, -S (O) 2- or -CO-.
- the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. The same ones as preferred are mentioned.
- R 6 to R 13 include the same preferred ones of R 1 to R 5 and Y 1 and groups 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). Preferably, at least one of R 6 to R 9 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). More preferred.
- Examples of the compound (I) include compounds represented by the formulas (Ia) shown in Tables 1 to 7 below or alkali metal salts thereof.
- the symbols in the "Q 1 " and “Q 2 " columns in Tables 1 to 7 correspond to the groups represented by the above formulas, respectively. * Indicates a joint hand.
- Examples of the compound (I) include compounds represented by the formulas (Ib) shown in Tables 8 to 27 below or alkali metal salts thereof.
- R Ib1 ⁇ R Ib5 is RR group, other four are hydrogen atoms.
- the symbols in the "Q 1 " and “Q 2 " columns in Tables 8 to 27 correspond to the groups represented by the above formulas, respectively.
- the symbols described in the “RR” column in Tables 8 to 27 represent RR groups, and the following formulas (a1) to (a69); Equations (b1) to (b4); Equations (c1) to (c4); Equations (d1) to (d5); Equations (e1) to (e20); Equations (f1) to (f5); Equations (g1) to (g9); Equations (h1) to (h9); Equations (j1) to (j9); Equations (k1) to (k4); Equations (m1) to (m9); Equations (n1) to (n3); Equation ( Cincinnati1) to Equation ( Cincinnati5); Equations (p1) to (p23); Equations (q1) to (q26); Equations (r1) to (r26); Equations (s1) to (s26); Equation (t1); Corresponds to the group represented by The numerical values shown in the “No” column in Tables 8 to 27 represent the positions where the RR groups are substituted, respectively.
- “1” indicates that the RR group is substituted with RIb1 .
- “2” indicates that the RR group is substituted with RIb2 .
- “3” indicates that the RR group is substituted with RIb3 .
- “4” indicates that the RR group is substituted with RIb4 .
- “5” indicates that the RR group is substituted with RIb5 . * Indicates a joint hand.
- Examples of the compound (I) include compounds represented by the formulas (If) shown in Tables f1 to f6 below or alkali metal salts thereof.
- the symbols in the "Q 1 " and “Q 2 " columns in Tables f1 to f6 correspond to the groups represented by the above formulas, respectively. * Indicates a joint hand.
- a fluorine atom for example, a compound in which all the hydrogen atoms of the aromatic ring represented by the formulas (Ic1) to (Ic3) are substituted with one or more selected from a fluorine atom, a chlorine atom and a bromine atom.
- compounds 1-6 -SO 3 H is substituted on the compounds of the formula shown in Table 1 (Ia3) represents the following structure.
- -(SO 3 H) 1 to 6 means that -SO 3 H replaces any one of 1 to 6 hydrogen atoms of the compound represented by the formula (Ia3). It shall be.
- Examples of the compound (I) include compounds represented by the formulas (Ia1) to (Ia1050), formulas (Ib1) to (Ib1532) and formulas (If1) to formula (If1367). And one or more selected from the substituted anions, - -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 consisting of one or more cations selected from Na + and K + .
- Examples of the compound (I) include an anion represented by the formula (Id) shown in Table 28 below and an anion represented by the formula (Ih) shown in Table h1.
- a metal salt consisting of one or more cations selected from Na + and K + .
- metal salts examples include metal salts represented by the formula (Ie) shown in Tables 29 to 30 below.
- Mg 2+ represents Mg 2+ as a symbol described in the "Met" column in Tables 29 to 30.
- Ca 2+ stands for Ca 2+
- Sr2 + represents Sr2 + and represents Ba2 + represents the Ba 2+
- Ni2 + stands for Ni 2+ Zn2 + represents Zn 2+ and represents Fe2 + represents Fe 2+ and represents Co2 + represents the Co 2+
- Sn2 + represents Sn2 + and represents Mn2 + represents Mn 2+ and represents Al3 + represents Al 3+
- Fe3 + represents Fe 3+ and represents Cr3 + represents the Cr 3+
- Sn4 + represents a Sn 4+
- Mn4 + represents the Mn 4+
- Cu2 + represents Cu 2+ and represents Li + stands for Li + Na + stands for Na + K + represents K + .
- M in the formula (Ie) is an integer of 1 or more, preferably an integer of 1 to 20, and more preferably an integer of 1 to 10.
- N in the formula (Ie) is an integer of 1 or more, preferably an integer of 1 to 20, and more preferably an integer of 1 to 10.
- m and n are the ratio of the number of ligands and the number of metal atoms such that the charge of the compound (I) becomes zero.
- compound (I) is represented as the above-mentioned oligomer or polymer.
- Compounds represented by formulas (Ia1) to (Ia903), formulas (Ia972) and formulas (If1) to formulas (If1355) are more preferable.
- Compounds represented by formulas (Ia1) to (Ia903) are particularly preferable.
- Compounds represented by formulas (Ia1) to (Ia119) are more preferable.
- Compounds represented by formulas (Ia1) to (Ia5), formulas (Ia26) and formulas (Ia87) to (Ia89) are particularly preferable.
- Compounds represented by formulas (Ia2) to (Ia3) are extremely preferable. The compound represented by the formula (Ia3) is most preferable.
- the compound represented by the formula (I) can be produced by reacting the compound represented by the formula (pt1) with 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) used in the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is determined by the formula (pt2). It is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, still more preferably 1 to 10 mol, relative to 1 mol of the compound represented by (pt1). It is a mole.
- the amount of the compound represented by the formula (pt3) used in the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is determined by the formula (pt3). It is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, still more preferably 1 to 10 mol, relative to 1 mol of the compound represented by (pt1). It is a mole.
- 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., and particularly preferably 150 to 200 ° C. ..
- the reaction time is usually 0.5 to 500 hours.
- 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 usually carried out in the presence of a solvent.
- the solvent water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1 -Alcohol solvents such as 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 carbides such as hexane Hydrogen solvent; aromatic hydrocarbon solvent such as toluene, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzen
- diphenyl ether methyl benzoate, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene),
- examples thereof include 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide.
- 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, etc.
- trimethylbenzene eg 1,3,5-trimethylbenzene
- decalin tetralin
- 1,2-dichlorobenzene trichlorobenzene
- trichlorobenzene eg 1,3,5-trichlorobenzene
- 1-chloronaphthalene 2-chloronaphthalene
- nitrobenzene N-methylpyrrolidone, etc.
- methyl benzoate can be mentioned.
- the amount of the solvent used is the compound represented by the formula (pt1) 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 usually 1 to 1000 parts by mass with respect to 1 part by mass.
- one or more selected from acids and metal salts may coexist. preferable.
- the acid examples 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; acetic acid. , Carboxylic acids such as trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartrate; etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfon. Acids, p-toluenesulfonic acids and carboxylic acids can be mentioned, more preferably carboxylic acids and even more preferably benzoic acids.
- inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid
- 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 the compound 1 represented by the formula (pt1).
- it is usually 1 to 90 mol, preferably 1 to 70 mol, more preferably 1 to 50 mol, still more preferably 1 to 30 mol.
- Examples of the metal salt include zinc chloride and aluminum chloride.
- 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 the compound represented by the formula (pt1). It is usually 0.01 to 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, and even more preferably 0.01 to 3 mol, relative to 1 mol. ..
- the method for extracting compound (I) from the reaction mixture is not particularly limited, and it can be extracted by various known methods.
- the reaction mixture is added to a solvent such as methanol, in which the compound (I) in the reaction mixture is difficult to dissolve, but the compounds other than the compound (I) are easily dissolved, and the reaction mixture is mixed well and then filtered. By doing so, compound (I) can be taken out.
- an amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and /
- the obtained residue may be washed with an acidic aqueous solution such as hydrochloric acid and then washed with water, a low boiling alcohol such as methanol or a mixed solvent thereof, and the compound (I) may be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and / or recrystallization or the like.
- the reaction mixture may be purified by column chromatography and / or recrystallization or the like.
- the compound (I) in the reaction mixture is difficult to dissolve, but the compound other than the compound (I) is easily dissolved.
- a solvent such as methanol, and then filtering.
- Compound (I) can be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the compound represented by the formula (I) is Depending on the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), the compound represented by the formula (I ′′) (hereinafter, referred to as the compound (I ′′) may be used. ), followeded by The compound represented by the formula (I'') is hydrolyzed in the presence of a base to produce a compound represented by the formula (IM1) (hereinafter, may be referred to as a compound (IM1)), and further. It can be produced by reacting the compound represented by the formula (IM1) with the compound represented by the formula (pt3).
- the amount of the compound represented by the formula (pt2) used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is 1 mol of the compound represented by the formula (pt1). On the other hand, it is usually 0.1 to 60 mol, preferably 1 to 40 mol, more preferably 1 to 32 mol, and further preferably 2 to 20 mol.
- the amount of the compound represented by the formula (pt3) used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is 1 mol of the compound represented by the formula (IM1). On the other hand, it is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and further preferably 1 to 10 mol.
- the reaction temperature in the above is usually ⁇ 100 to 300 ° C., preferably 0 to 280 ° C., more preferably 50 to 250 ° C., further preferably 100 to 230 ° C., and particularly preferably 150 to 200 ° C. is there.
- 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) is usually 0.5 hour to 500 hours.
- 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 carried out. , Performed in the presence of a solvent.
- a solvent 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) Water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol , Alcohol solvents such as phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, 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, trimethyl
- diphenyl ether methyl benzoate, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene),
- examples thereof include 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide.
- 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, etc.
- trimethylbenzene eg 1,3,5-trimethylbenzene
- decalin tetralin
- 1,2-dichlorobenzene trichlorobenzene
- trichlorobenzene eg 1,3,5-trichlorobenzene
- 1-chloronaphthalene 2-chloronaphthalene
- nitrobenzene N-methylpyrrolidone, etc.
- methyl benzoate can be mentioned.
- 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 mass by mass with respect to 1 part by mass of the compound represented by the formula (pt1). It is a department.
- 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 to 1000 with respect to 1 part by mass of the compound represented by the formula (IM1). It is a mass part.
- the acid And one or more selected from metal salts coexist.
- Is an inorganic acid such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid; sulfonic acid such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; acetic acid, tri Carboxylic acids such as fluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartrate; and the like; preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, etc. Examples thereof include p-toluenesulfonic acid
- the amount of 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 mol with respect to 1 mol of the compound represented by the formula (pt1). Yes, preferably 1 to 70 mol, more preferably 1 to 50 mol, still more preferably 1 to 30 mol.
- 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 mol with respect to 1 mol of the compound represented by the formula (IM1). It is preferably 1 to 70 mol, more preferably 1 to 50 mol, and even more preferably 1 to 30 mol.
- Examples thereof include zinc chloride and aluminum chloride.
- 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 1 mol with respect to 1 mol of the compound represented by the formula (pt1). It is 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, and even more preferably 0.01 to 3 mol.
- 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 with respect to 1 mol of the compound represented by the formula (IM1). It is ⁇ 30 mol, preferably 0.01 ⁇ 20 mol, more preferably 0.01 ⁇ 10 mol, still more preferably 0.01 ⁇ 3 mol.
- the method for extracting the compound represented by the formula (I ′′) from the reaction mixture in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is not particularly limited, and various known methods are available. It can be taken out by the method of. For example, after completion of the reaction, a solvent such as methanol, which is difficult to dissolve the compound (I ′′) in the reaction mixture but easily dissolves a compound other than the compound (I ′′), and the reaction mixture were well mixed. After that, the compound (I ′′) can be taken out by filtering.
- an amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and /
- the obtained residue may be washed with an acidic aqueous solution such as hydrochloric acid and then washed with water, a low boiling alcohol such as methanol or a mixed solvent thereof, and the compound (I ′′) may be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and / or recrystallization or the like.
- the reaction mixture may be purified by column chromatography and / or recrystallization or the like.
- the compound (I ′′) in the reaction mixture is difficult to dissolve, but the compound other than the compound (I ′′) is easily dissolved.
- a solvent such as methanol
- the method for extracting the compound represented by the formula (I) from the reaction mixture in the reaction of the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is not particularly limited, and various known methods are used. It can be taken out by the method. For example, after completion of the reaction, the compound (I) in the reaction mixture is difficult to dissolve, but the compound other than the compound (I) is easily dissolved. A solvent such as methanol and the reaction mixture are well mixed and then filtered. Thereby, the compound (I) can be taken out.
- an amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and /
- the obtained residue may be washed with an acidic aqueous solution such as hydrochloric acid and then washed with water, a low boiling alcohol such as methanol or a mixed solvent thereof, and the compound (I) may be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and / or recrystallization or the like.
- the reaction mixture may be purified by column chromatography and / or recrystallization or the like.
- the compound (I) in the reaction mixture is difficult to dissolve, but the compound other than the compound (I) is easily dissolved.
- a solvent such as methanol, and then filtering.
- Compound (I) can be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the bases in the hydrolysis reaction of the compound represented by the formula (I ′′) include triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine, piperidine, 1,8-diazabicyclo [5. 4.0] Organic bases such as undec-7-ene and 1,5-diazabicyclo [4.3.0] nona-5-ene, sodium methoxydo, sodium ethoxydo, sodium tert-butoxide, potassium tert-butoxide, etc.
- Metal alkoxides organic metal compounds such as methyllithium, butyllithium, tert-butyllithium and phenyllithium, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like.
- Inorganic bases etc. Inorganic bases are preferred Lithium hydroxide, sodium hydroxide, and potassium hydroxide are more preferred. Sodium hydroxide and potassium hydroxide are more preferred Potassium hydroxide is particularly preferred.
- the amount of the base used in the hydrolysis reaction of the compound represented by the formula (I ′′) is usually 0.1 to 100 with respect to 1 mol of the compound represented by the formula (I ′′). It is mol, preferably 1 to 70 mol, more preferably 2 to 40 mol.
- the amount of water used in the hydrolysis reaction of the compound represented by the formula (I ′′) is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (I ′′). It is preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and further preferably 1 to 50 parts by mass.
- the reaction temperature in the hydrolysis reaction of the compound represented by the formula (I ′′) in the presence of a base is usually 0 to 100 ° C., preferably 5 to 100 ° C., and more preferably 20 to 100 ° C. ° C., more preferably 40 to 100 ° C., and particularly preferably 60 to 100 ° C.
- the reaction time in the hydrolysis reaction of the compound represented by the formula (I'') in the presence of a base is usually 0.5 to 120 hours, preferably 1 to 72 hours, and more preferably 1 ⁇ 24 hours.
- the method for extracting the compound represented by the formula (IM1) from the reaction mixture in the hydrolysis reaction of the compound represented by the formula (I'') in the presence of a base is not particularly limited, and the compound represented by the formula (IM1) can be extracted by various known methods. Can be done. For example, after completion of the reaction, the compound (IM1) can be taken out by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture to neutralize the mixture, and then filtering the mixture.
- an acidic aqueous solution such as hydrochloric acid
- amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone
- sulfoxide solvents such as dimethyl sulfoxide
- ketone solvents such as acetone
- alcohol solvents such as methanol
- nitrile solvents such as acetonitrile.
- the compound (IM1) may be taken out by washing the obtained residue with 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. Further, it may be purified by column chromatography and / or recrystallization.
- the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and / or recrystallization or the like.
- the reaction mixture may be purified by column chromatography and / or recrystallization or the like.
- the compound (IM1) can be taken out by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture to neutralize the mixture, and then filtering the mixture. Further, it may be purified by column chromatography and / or recrystallization.
- the compound represented by the formula (I) is A compound represented by the formula (IM2) (hereinafter, may be referred to as a compound (IM2)) is produced by reacting the compound represented by the formula (pt1) with the compound represented by the formula (pt3). ,continue, It can be produced by reacting the compound represented by the formula (IM2) with the compound represented by the formula (pt2).
- the amount of the compound represented by the formula (pt3) used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is 1 mol of the compound represented by the formula (pt1). On the other hand, it is usually 0.1 to 10 mol, preferably 0.1 to 5 mol, more preferably 0.5 to 2 mol, still more preferably 0.8 to 1.5 mol. Is.
- 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, and more preferably 50. It is about 250 ° C., more preferably 100 to 230 ° C., and particularly preferably 120 to 200 ° C.
- 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 hour to 500 hours.
- 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.
- the solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-.
- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether; acetone, methyl Ketone solvent such as isobutyl ketone; ester solvent such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvent such as hexane; aromatics such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin and tetraline.
- Group hydrocarbon solvent Halogenized hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrobenzene Etc., such as nitrated hydrocarbon solvents; amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethylsulfoxide; and the like.
- Halogenized hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene
- nitrobenzene Etc. such as nitrated hydrocarbon solvents
- amide solvents such as N, N-d
- trimethylbenzene eg 1,3,5-trimethylbenzene
- decalin etralin
- 1,2-dichlorobenzene 1,2-dichlorobenzene
- trichlorobenzene eg 1,3,5-trichlorobenzene
- phenol diphenyl ether, methyl benzoate, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene).
- chlorobenzene 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, etc.
- phenol and methyl benzoate can be mentioned.
- Phenol is particularly preferable.
- 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 with respect to 1 part by mass of the compound represented by the formula (pt1). It is a mass portion, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and further preferably 1 to 50 parts by mass.
- the method for extracting the compound (IM2) from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and can be extracted by various known methods. it can.
- the compound (IM2) in the reaction mixture is difficult to dissolve, but the compound other than the compound (IM2) is easily dissolved.
- a solvent such as methanol and the reaction mixture are well mixed and then filtered. Thereby, the compound (IM2) can be taken out.
- amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone
- sulfoxide solvents such as dimethyl sulfoxide
- ketone solvents such as acetone
- alcohol solvents such as methanol
- nitrile solvents such as acetonitrile.
- the compound (IM2) can be taken out by washing the obtained residue with 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. Further, it may be purified by column chromatography and / or recrystallization.
- the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and / or recrystallization or the like.
- the reaction mixture may be purified by column chromatography and / or recrystallization or the like.
- the compound (IM2) in the reaction mixture is difficult to dissolve, but the compound other than the compound (IM2) is easily dissolved.
- a solvent such as methanol, and then filtering.
- Compound (IM2) can be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the amount of the compound represented by the formula (pt2) used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is 1 mol of the compound represented by the formula (IM2). On the other hand, it is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and further preferably 1 to 10 mol.
- 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 50. It is about 250 ° C., more preferably 100 to 230 ° C., and particularly preferably 150 to 200 ° C.
- 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 hour to 500 hours.
- 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.
- the solvent in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-.
- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether; acetone, methyl Ketone solvent such as isobutyl ketone; ester solvent such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvent such as hexane; aromatics such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin and tetraline.
- Group hydrocarbon solvent Halogenized hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrobenzene Etc., such as nitrated hydrocarbon solvents; amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethylsulfoxide; and the like.
- Halogenized hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene
- nitrobenzene Etc. such as nitrated hydrocarbon solvents
- amide solvents such as N, N-d
- diphenyl ether methyl benzoate, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene),
- examples thereof include 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide.
- 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, etc.
- trimethylbenzene eg 1,3,5-trimethylbenzene
- decalin tetralin
- 1,2-dichlorobenzene trichlorobenzene
- trichlorobenzene eg 1,3,5-trichlorobenzene
- 1-chloronaphthalene 2-chloronaphthalene
- nitrobenzene N-methylpyrrolidone, etc.
- methyl benzoate can be mentioned.
- 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 to 1000 with respect to 1 part by mass of the compound represented by the formula (IM2). It is a mass part.
- Examples of the acid in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid.
- Etc. preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid, still more preferably.
- Benzoic acid can be mentioned.
- the amount of 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 mol with respect to 1 mol of the compound represented by the formula (IM2). It is preferably 1 to 70 mol, more preferably 1 to 50 mol, and even more preferably 1 to 30 mol.
- 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.
- 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 with respect to 1 mol of the compound represented by the formula (IM2). It is ⁇ 30 mol, preferably 0.01 ⁇ 20 mol, more preferably 0.01 ⁇ 10 mol, still more preferably 0.01 ⁇ 3 mol.
- the method for extracting the compound represented by the formula (I) from the reaction mixture in the reaction of the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is not particularly limited, and various known methods are used. It can be taken out by the method. For example, after completion of the reaction, the compound (I) in the reaction mixture is difficult to dissolve, but the compound other than the compound (I) is easily dissolved. A solvent such as methanol and the reaction mixture are well mixed and then filtered. Thereby, the compound (I) can be taken out.
- an amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and /
- the obtained residue may be washed with an acidic aqueous solution such as hydrochloric acid and then washed with water, a low boiling alcohol such as methanol or a mixed solvent thereof, and the compound (I) may be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and / or recrystallization or the like.
- the reaction mixture may be purified by column chromatography and / or recrystallization or the like.
- the compound (I) in the reaction mixture is difficult to dissolve, but the compound other than the compound (I) is easily dissolved.
- a solvent such as methanol, and then filtering.
- Compound (I) can be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- a sulfo group or -SO 3 M can be introduced into compound (I) by reacting compound (I) with a sulfating agent such as fuming sulfuric acid or chlorosulfonic acid.
- a sulfating agent such as fuming sulfuric acid or chlorosulfonic acid.
- the amount of SO 3 used in fuming sulfuric acid is usually 1 to 200 mol, preferably 2 to 150 mol, more preferably 3 to 100 mol, still more preferably 1 mol, relative to 1 mol of compound (I). Is 5-80 mol.
- SO 3 in fuming sulfuric acid is usually 1 to 90 parts by mass, preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and further preferably 15 to 15 to 90 parts by mass in 100 parts by mass of fuming sulfuric acid. It is 50 parts by mass.
- the amount of chlorosulfonic acid used is usually 1 to 500 mol, preferably 1 to 300 mol, more preferably 1 to 200 mol, still more preferably 1 to 150 mol, per 1 mol of compound (I). It is a mole.
- a sulfo group or -SO 3 M into compound (I) using chlorosulfonic acid it may be carried out in the presence of a solvent.
- the solvent include halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene and 2-chloronaphthalene. Be done.
- the amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of compound (I).
- the reaction temperature for sulfonation is usually ⁇ 20 to 200 ° C., preferably ⁇ 10 to 150 ° C., and more preferably 0 to 100 ° C.
- the reaction time is usually 0.5 to 300 hours.
- the method for extracting the compound in which the sulfo group or -SO 3 M is introduced into the compound (I) from the reaction mixture is not particularly limited, and can be extracted by various known methods. For example, after completion of the reaction, the reaction mixture is added dropwise to ice, and the obtained mixture is filtered to extract a compound in which a sulfo group or -SO 3 M is introduced into compound (I). Further, it may be purified by column chromatography and / or recrystallization.
- a sulfo group or -Compounds (I) are compounded by mixing with an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, and a hydrophilic organic solvent such as a mixed solvent thereof, in which compounds other than the compound into which SO 3 M has been introduced are easily dissolved, and filtering.
- an alcohol solvent such as methanol
- a nitrile solvent such as acetonitrile
- a hydrophilic organic solvent such as a mixed solvent thereof
- reaction mixture is added dropwise to ice, the obtained mixture is neutralized with an aqueous solution of ammonia, a water-soluble amine or a mixture thereof, and then this mixture is mixed with an alcohol solvent such as methanol, acetonitrile or the like.
- alcohol solvent such as methanol, acetonitrile or the like.
- a compound in which a sulfo group or -SO 3 M is introduced into compound (I) by mixing with a hydrophilic organic solvent such as a nitrile solvent and a mixed solvent thereof, filtering, and distilling off the solvent of the obtained filtrate. Can be taken out. Further, it may be purified by column chromatography and / or recrystallization.
- the amount of the salt having MM to be used is usually 0.01 to 100 mol, preferably 0.02 to 50 mol, per 1 mol of compound (I) having ⁇ SO 3 H and / or ⁇ CO 2 H. It is more preferably 0.1 to 30 mol.
- the reaction temperature is usually 0 to 100 ° C., preferably 0 to 80 ° C., more preferably 0 to 60 ° C., and even more preferably 0 to 40 ° C.
- the reaction time is usually 0.5 to 500 hours.
- the reaction of compound (I) with -SO 3 H and / or -CO 2 H with a salt with MM is usually carried out in the presence of a solvent.
- the solvent include water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, Alcohol solvents such as 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 such as hexane Carbide solvent; aromatic hydrocarbon solvent such as toluene, trimethylbenzene (eg 1,3,
- nitrile solvent such as acetonitrile
- alcohol solvent such as methanol, ethanol, 1-propanol, 2-propanol
- ether solvent such as tetrahydrofuran
- ketone solvent such as acetone
- An amide solvent such as N-methylpyrrolidone
- a sulfoxide solvent such as dimethyl sulfoxide
- a mixed solvent thereof are preferable. Water is more preferred.
- 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 to 300 parts by mass.
- reaction of compound (I) with -SO 3 H and / or -CO 2 H with a salt with MM may be carried out in the presence of a base.
- Examples of the base include triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine, piperidine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4.3]. .0]
- Organic bases such as nona-5-ene, metal alkoxides such as sodium methoxydo, sodium ethoxydo, sodium tert-butoxide, potassium tert-butoxide, methyllithium, butyllithium, tert-butyllithium, phenyllithium and the like.
- Examples thereof include organic metal compounds, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and inorganic bases such as potassium hydroxide.
- Inorganic bases are preferred Lithium hydroxide, sodium hydroxide, and potassium hydroxide are more preferred. Sodium hydroxide and potassium hydroxide are more preferred Sodium hydroxide is particularly preferred.
- the amount of the base used is usually 1 to 100 mol, preferably 1 to 50 mol, more preferably 1 mol, relative to 1 mol of compound (I) having ⁇ SO 3 H and / or ⁇ CO 2 H. It is 1 to 20 mol, more preferably 1 to 10 mol.
- the method for extracting the compound (I) having -SO 3 (MM) and / or -CO 2 (MM) from the reaction mixture is not particularly limited, and can be extracted by various known methods.
- the reaction mixture can be filtered to remove compound (I) having -SO 3 (MM) and / or -CO 2 (MM).
- amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone
- sulfoxide solvents such as dimethyl sulfoxide
- ketone solvents such as acetone
- alcohol solvents such as methanol
- nitrile solvents such as acetonitrile.
- the obtained residue may be washed and purified with water or a mixed solvent thereof.
- the coloring composition of the present invention contains compound (I) and solvent (E). According to the coloring composition of the present invention, C.I. I. A darker color filter can be formed as compared with the coloring composition containing Pigment Yellow 138.
- the color filter formed from the coloring composition of the present invention is suitably used for a display device such as a liquid crystal display device.
- the coloring composition of the present invention is preferably a yellow composition, an orange composition, a red composition and a green composition.
- the content of the solid content in the coloring composition is less than 100% by mass, preferably 0.01% by mass or more and less than 100% by mass, more preferably 0.1% by mass, based on the total amount of the coloring composition. % Or more and 99.9% by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 90% by mass or less, and even more preferably 1% by mass or more and 80% by mass. % Or less, particularly preferably 1% by mass or more and 70% by mass or less, extremely preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.
- total amount of solid content means the total amount of the components excluding the solvent (E) from the coloring composition of the present invention.
- the total amount of solids and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography or gas chromatography.
- the content of the compound (I) in the coloring composition is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001, based on the total solid content. It is mass% or more and 99 mass% or less, more preferably 0.0001 mass% or more and 90 mass% or less, particularly preferably 0.0001 mass% or more and 80 mass% or less, still more preferably 0.0001 mass% or less. It is 70% by mass or less, particularly preferably 0.0001% by mass or more and 60% by mass or less, extremely preferably 0.0001% by mass or more and 55% by mass or less, and most preferably 0.1% by mass or more and 55. It is mass% or less.
- the solvent (E) is not particularly limited, and a solvent usually used in the art can be used.
- the solvent (E) includes, for example, an ester solvent (a solvent containing -CO-O- in the molecule and not containing -O-) and an ether solvent (a solvent containing -O- in the molecule and containing -CO-O-".
- solvent No solvent
- ether ester solvent solvent containing -CO-O- and -O- in the molecule
- ketone solvent solvent containing -CO- in the molecule and not -CO-O-
- alcohol examples thereof include solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -CO-O-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.
- ester solvent examples include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, 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, ⁇ -butyrolactone and the like.
- ether solvent examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether.
- ether ester solvent examples include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy.
- Ethyl propionate methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.
- Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.
- alcohol solvent examples include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
- aromatic hydrocarbon solvent examples include benzene, toluene, xylene, mesitylene and the like.
- amide solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
- Two or more of these solvents may be used in combination.
- an organic solvent having a boiling point of 120 ° C. or higher and 180 ° C. or lower at 1 atm is preferable from the viewpoint of coatability and drying property.
- the solvent is preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2.
- -Pentanone and N, N-dimethylformamide are mentioned, and more preferably, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone. And so on.
- the content of the solvent (E) is less than 100% by mass, preferably 99.99% by mass or less, and more preferably 0.1% by mass or more and 99.9% by mass with respect to the total amount of the coloring composition.
- it is more preferably 1% by mass or more and 99.9% by mass or less, particularly preferably 10% by mass or more and 99% by mass or less, still more preferably 20% by mass or more and 99% by mass or less, and particularly preferably 30% by mass.
- the resin (B) is preferably an alkali-soluble resin, and is at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter, "monomer (a)"). It is more preferable that the polymer 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, may be referred to as “monomer (b)”). And other structural units are preferred.
- the other structural unit is a monomer copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b).
- the monomer (c)) A structural unit derived from), a structural unit having an ethylenically unsaturated bond, and the like can be mentioned.
- (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
- Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid and unsaturated monocarboxylic acids such as o-, m- and 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-cyclohexendicarboxylic 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
- acrylic acid, methacrylic acid, o-, m-, p-vinylbenzoic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an alkaline aqueous solution.
- the monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
- the monomer (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
- Examples of the monomer (b) include a monomer having an oxylanyl group and an ethylenically unsaturated bond (hereinafter, may be referred to as “monomer (b1)”), an oxetanyl group and an ethylenically unsaturated bond.
- a monomer having a saturated bond hereinafter, may be referred to as “monomer (b2)” and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, “monomer (b3)”).
- ) a monomer having an oxylanyl group and an ethylenically unsaturated bond
- the monomer (b1) is, for example, a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, referred to as “monomer (b1-1)”). In some cases) and a monomer having an epoxidized structure of an alicyclic unsaturated hydrocarbon (hereinafter, may be referred to as “monomer (b1-2)”).
- a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.
- the monomer (b1-1) for example, Glycidyl (meth) acrylate, ⁇ -methylglycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, ⁇ - Methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene,
- Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, celloxide® 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxy. Cyclohexylmethyl (meth) acrylate (eg, Cyclomer® A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, Cyclomer® M100; Daicel Co., Ltd.) Manufacture), a compound represented by the formula (BI), a compound represented by the formula (BII), and the like.
- vinylcyclohexene monooxide for example, celloxide® 2000; manufactured by Daicel Co., Ltd.
- Cyclohexylmethyl (meth) acrylate eg, Cyclomer® A400; manufactured by Daicel Co., Ltd.
- Ra and R b 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 replaced with.
- X a and X b are each independently a single bond, * - R c -, * - R c -O -, * - represents the R c -S- or * -R c -NH-.
- R c represents an alkanediyl group having 1 to 6 carbon atoms. * Represents a bond with O.
- alkyl group having 1 to 4 carbon atoms examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group and the like.
- alkyl group in which the hydrogen atom is substituted with hydroxy examples include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and 1 -Hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like can be mentioned.
- R a and R b include 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.
- alkanediyl group examples include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and the like. Examples thereof include hexane-1,6-diyl groups.
- Examples of X a and X b are 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- can be mentioned (* represents a bond with O).
- Examples of the compound represented by the formula (BI) include compounds represented by any of the formulas (BI-1) to (BI-15). Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI-9) and the formulas (BI-11) to the formulas (BI-15). The compound represented by the formula (BI-1), the formula (BI-7), the formula (BI-9) and the compound represented by the formula (BI-15) are more preferable.
- Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15), and among them, the formula (BII-1) and the formula (BII-1) are preferable.
- (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and compounds represented by formulas (BII-11) to formula (BII-15) can be mentioned.
- Preferred examples thereof include compounds represented by the formula (BII-1), the formula (BII-7), the formula (BII-9) and the formula (BII-15).
- 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.
- a compound represented by the formula (BI) and a compound represented by the formula (BII) may be used in combination.
- the content ratio thereof is On a molar basis, it is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.
- the monomer (b2) a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable.
- the monomer (b2) include 3-methyl-3-methacrylloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, and 3-ethyl-3.
- the monomer (b3) a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable.
- the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Viscort V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.
- the monomer (b) is preferably the monomer (b1) in that the reliability of the obtained color filter such as heat resistance and chemical resistance can be further improved. Further, the monomer (b1-2) is more preferable in that the coloring composition is excellent in storage stability.
- Examples of the monomer (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl.
- Halogenized hydrocarbons such as vinyl 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 ; Etc. can be mentioned.
- the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer and 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-epoxy Tricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate / phenyl (meth) acrylate / o-vinyl benzoic acid copolymer, 3,4-epoxytricyclo [
- the resin (B) a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) is preferable. Two or more kinds of resin (B) may be combined, and in this case, the resin (B) is at least It is preferable to contain at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b). It is more preferable to contain at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1).
- the polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 to 100,000, more preferably 1,000 to 50,000, and even more preferably 1,000 to 30, It is 000, particularly preferably 3,000 to 30,000, and particularly preferably 5,000 to 30,000.
- the dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1 to 6, more preferably 1 to 5, and even more preferably 1 to 4.
- the acid value (solid content conversion value) of the resin (B) is preferably 10 to 500 mg-KOH / g, more preferably 20 to 450 mg-KOH / g, still more preferably 20 to 400 mg-KOH / g, and even more preferably. Is 20 to 370 mg-KOH / g, even more preferably 30 to 370 mg-KOH / g, even more preferably 30 to 350 mg-KOH / g, particularly preferably 30 to 340 mg-KOH / g, most preferably. It is 30 to 335 mg-KOH / g.
- the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titrating with an aqueous potassium hydroxide solution.
- the content of the resin (B) in the coloring composition is less than 100% by mass, preferably 0.00001% by mass or more and 99.99999% by mass or less, more preferably 1 with respect to the total amount of solids.
- mass% or more and 99% by mass or less more preferably 1% by mass or more and 97% by mass or less, particularly preferably 1% by mass or more and 95% by mass or less, and even more preferably 3% by mass or more and 95% by mass or less. It is particularly preferably 5% by mass or more and 95% by mass or less, and extremely preferably 10% by mass or more and 95% by mass or less.
- a compound (I) -containing liquid containing the compound (I) and the solvent (E) is prepared in advance, and then the coloring composition is prepared using the compound (I) -containing liquid. May be good.
- the compound (I) -containing liquid may be prepared by dispersing the compound (I) in the solvent (E) and mixing.
- the compound (I) -containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.
- the compound (I) -containing liquid is contained in the coloring composition of the present invention.
- the solid content of the compound (I) -containing liquid is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, based on the total amount of the compound (I) -containing liquid. More preferably 0.1% by mass or more and 99.9% by mass or less, further preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 90% by mass or less, still more preferably 1% by mass. It is 80% by mass or less, particularly preferably 1% by mass or more and 70% by mass or less, extremely preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.
- the content of the compound (I) in the compound (I) -containing liquid is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass, based on the total amount of solids in the compound (I) -containing liquid. It is more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 1% by mass or more and 99% by mass or less, and particularly preferably 3% by mass or more and 99% by mass or less, more preferably. Is 5% by mass or more and 99% by mass or less.
- the compound (I) is treated with rosin, a surface treatment using a derivative having an acidic group or a basic group introduced therein, a graft treatment on the surface of the compound (I) with a polymer compound or the like, and sulfate atomization, if necessary.
- a micronization treatment by a method or the like, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment of ionic impurities by an ion exchange method or the like may be performed.
- compound (I) may be used as required.
- Granulation by salt milling method, crystal structure conversion, particle shaping and / or substantially uniform particle size Compound (I) was mixed with water and / or an organic solvent and stirred with stirring and / or heating to obtain a suspension, and then the suspension was filtered to change the crystal structure. Treatment to obtain compound (I), atomization treatment, particle shaping treatment and / or substantially uniform particle size treatment; Treatment to change the crystal structure of compound (I) by recrystallization, atomization treatment, particle shaping treatment and / or substantially uniform particle size treatment; Compound (I) is mixed with water, sulfuric acid or an organic solvent, and the mixture is stirred with stirring and / or heating to obtain a solution or suspension, and then the solution or suspension is subjected to compound (I).
- the suspension After mixing with a poor solvent of the compound (I) to obtain a suspension, the suspension is filtered to obtain a mixture containing the compound (I) having a changed crystal structure, the compound (I) and the derivative.
- Treatment of mixing with, atomization treatment, shaping treatment of particles and / or substantially uniform treatment of particle size; Etc. may be applied.
- these treatments may be performed individually, or a plurality of types may be mixed and treated.
- the particle size of compound (I) is preferably substantially uniform.
- Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.
- Alcohol solvent such as amine solvent; ether solvent such as diethyl ether, tetrahydrofuran, diphenyl ether; ketone solvent such as acetone, methyl isobutyl ketone; ester solvent such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvent such as hexane; toluene, trimethyl Aromatic hydrocarbon solvents such as benzene (eg 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene) ), 1-Chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and
- Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.
- Alcohol solvent such as amine solvent; ether solvent such as diethyl ether, tetrahydrofuran, diphenyl ether; ketone solvent such as acetone, methyl isobutyl ketone; ester solvent such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvent such as hexane; toluene, trimethyl Aromatic hydrocarbon solvents such as benzene (eg 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene) ), Halogenized hydrocarbon solvent such as 1-chloronaphthalene and 2-chloronaphthalene; and nitrated hydrocarbon solvent such as nitrobenzene; and the like.
- Aromatic hydrocarbon solvents such as benzene (eg 1,3,5-trimethylbenzene), de
- Examples of the derivative include a compound represented by the formula (z) and a compound represented by the formula (z1).
- the content of the derivative is 0.01 part by mass or more and 100 parts by mass or less, and 0.01 part by mass or more with respect to 100 parts by mass of the compound (I). It is preferably 70 parts by mass or less, more preferably 0.1 parts by mass or more and 50 parts by mass or less, further preferably 0.1 parts by mass or more and 30 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 20 parts by mass or less.
- the compound (I) can be uniformly dispersed in the compound (I) -containing liquid by subjecting the compound (I) to a dispersant and performing a dispersion treatment.
- a dispersant When a plurality of types of the compound (I) are used, they may be dispersed individually or a plurality of types may be mixed and dispersed.
- dispersant examples include surfactants and the like, which may be any of cationic, anionic, nonionic and amphoteric surfactants. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark).
- KP manufactured by Shin-Etsu Chemical Industry Co., Ltd.
- Floren manufactured by Kyoeisha Chemical Co., Ltd.
- Solsperse registered trademark
- EFKA registered trademark
- the amount of the dispersant (solid content) used is, for example, 0.01 part by mass or more and 10,000 parts by mass or less with respect to 100 parts by mass of the compound (I). It is preferably 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, and particularly preferably. Is 0.1 parts by mass or more and 300 parts by mass or less, more preferably 1 part by mass or more and 300 parts by mass or less, and particularly preferably 5 parts by mass or more and 260 parts by mass or less. When the amount of the dispersant used is in the above range, a more uniform dispersed compound (I) -containing liquid tends to be obtained.
- the coloring composition of the present invention contains a resin (B), and after preparing a compound (I) -containing liquid containing the compound (I) and the solvent (E) in advance, the present invention is performed using the compound (I) -containing liquid.
- the compound (I) -containing liquid may contain a part or all, preferably a part of the resin (B) contained in the coloring composition in advance. By including the resin (B) in advance, the dispersion stability of the compound (I) -containing liquid can be further improved.
- the content of the resin (B) is, for example, 0.01 part by mass or more and 10,000 parts by mass or less with respect to 100 parts by mass of the compound (I). It is preferably 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, and particularly preferably. It is 0.1 parts by mass or more and 300 parts by mass or less.
- the polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferable. It is a (meth) acrylic acid ester compound.
- Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. And the above-mentioned monomer (a), monomer (b) and monomer (c).
- 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. Examples thereof include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.
- the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
- examples of such a polymerizable compound include trimethritol propanthritol (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa.
- 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 particularly preferably. It is 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.
- 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, based on the total amount of solids in the coloring composition. Is 1% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 97% by mass or less, particularly preferably 1% by mass or more and 95% by mass or less, and further preferably 1% by mass or more and 90% by mass or less. It is less than or equal to, particularly preferably 2% by mass or more and 80% by mass or less, and extremely preferably 3% by mass or more and 70% by mass or less.
- the polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate 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 an oxime compound such as an O-acyloxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound and an acylphosphine oxide compound.
- O-acyloxym compound examples include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-.
- O-acyloxime compound commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used.
- O-acyloxym compound N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- At least one selected from the group consisting of 1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyl is preferable.
- Oxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.
- alkylphenone compound examples include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-. Examples thereof include on and 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one.
- commercially available products such as Irgacure 369, 907, 379 (all manufactured by BASF) may be used.
- alkylphenone compound examples include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, Also included are 1-hydroxycyclohexylphenylketone, an oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, ⁇ , ⁇ -diethoxyacetophenone and benzyl dimethyl ketal.
- biimidazole compound examples include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl) -4.
- triazine compounds examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl).
- acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
- Commercially available products such as Irgacure® 819 (manufactured by BASF) may be used.
- benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzoin compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthrene quinone, Kinone compounds such as 2-ethylanthraquinone and camphorquinone; examples include 10-butyl-2-chloroacrydone, benzyl, methyl phenylglioxylate and titanosen compounds.
- a polymerization initiator hereinafter, may be referred to as
- the polymerization initiator (D) is preferably a polymerization initiator containing 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, and more preferably an oxime compound. It is a polymerization initiator containing, and more preferably a polymerization initiator containing an O-acyloxime compound.
- the content of the polymerization initiator (D) is preferably 0.001% by mass or more and 60% by mass or less, more preferably 0.01, based on the total amount of the resin (B) and the polymerizable compound (C). It is by mass% or more and 50% by mass or less.
- the coloring composition of the present invention may contain a polymerization initiator (D1).
- the polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D).
- the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).
- Examples of the polymerization initiator (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.
- amine compound examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-Ethylhexyl dimethylaminobenzoate, 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 and the like, preferably 4,4'-bis (diethylamino) benzophenone and the like.
- EAB-F manufactured by Hodogaya Chemical Co., Ltd.
- alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Examples thereof include anthracene and 2-ethyl-9,10-dibutoxyanthracene.
- thioxanthone compound examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichloromethanexanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.
- carboxylic acid compound examples include phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanilic acid, N. -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.
- the content thereof is preferably 0.00001% by mass or more and 60% by mass or less with respect to the total amount of the resin (B) and the polymerizable compound (C). , More preferably 0.0001% by mass or more and 50% by mass or less.
- the coloring composition of the present invention may contain a coloring agent other than compound (I) (hereinafter, may be referred to as a coloring agent (A1)).
- the colorant (A1) may contain one or more colorants.
- the colorant (A1) preferably contains one or more selected from a yellow colorant, an orange colorant, a red colorant, and a green colorant, and preferably contains one or more selected from the yellow colorant and the green colorant. Is more preferable.
- the colorant (A1) may be a dye or a pigment.
- a known dye can be used, and examples thereof include known dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Color Dyeing Co., Ltd.). According to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acrydin dyes, styryl dyes, coumarin dyes, quinoline. Examples thereof include dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, and isoindrin dyes. These dyes may be used alone or in combination of two or more.
- 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.
- 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.
- I. Disperse 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.
- Lumogen registered trademark
- BASF's products include Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), Lumogen (registered trademark) F Orange 240. (BASF) and Lumogen (registered trademark) F Red 305 (BASF) can be mentioned.
- pigments known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). These may be used alone, or two or more kinds may be used in combination. Specifically, C.I. 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, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231; C. I.
- C. I. Examples thereof include black pigments such as Pigment Black 1, 7, 31, and 32.
- Examples of the colorant (A1) include a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as a "yellow colorant”), an orange dye and an orange pigment (hereinafter, these are collectively referred to as an "orange colorant”).
- red colorant red dye and red pigment
- green dye and green pigment green dye and green pigment
- yellow dye examples include dyes whose hue is classified as yellow among the above dyes, and examples of yellow pigments include pigments whose hue is classified as yellow among the above pigments.
- 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 further preferable, and C.I. I. Pigment Yellow 129, 138, 139, 150, 185, 231 are particularly preferred, and C.I. I. Pigment Yellow 138, 139, 150, 185, 231 are more preferred.
- orange dye examples include dyes whose hue is classified as orange among the above dyes
- orange pigment examples include pigments whose hue is classified as orange among the above pigments.
- an orange dye and an orange pigment are preferable, an orange pigment is more preferable, and C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 are even more preferred.
- red dyes examples include dyes whose hue is classified as red among the above dyes
- examples of the red pigment include pigments whose hue is classified as red among the above pigments.
- red colorant red dyes and red pigments are preferable, and azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane dyes and xanthene pigments.
- perylene pigments are more preferred.
- I. Acid Red 52, C.I. I. Pigment Red 144, 177, 179, 242, 254 and 269 are even more preferred.
- the yellow colorant the orange colorant or the red colorant
- the xanthene compound described in JP2013-235257A may be used.
- green dye examples include dyes whose hue is classified as green among the above dyes
- examples of the green pigment include pigments whose hue is classified as green among the above pigments.
- green colorant examples include green dyes and green pigments are preferable, green pigments are more preferable, phthalocyanine pigments are further preferable, copper halide phthalocyanine pigments, zinc halide phthalocyanine pigments and aluminum zinc halide phthalocyanine pigments are particularly preferable.
- I. Pigment Greens 7, 36, 58, 59, 62 and 63 are more preferred.
- colorant (A1) -containing liquid a colorant (A1) -containing liquid containing the colorant (A1) and a solvent (E) is prepared in advance, and then the colorant (A1) -containing liquid is prepared. May be used to prepare a colored composition.
- the colorant (A1) is insoluble in the solvent (E)
- the colorant (A1) -containing liquid can be prepared by dispersing the colorant (A1) in the solvent (E) and mixing.
- the colorant (A1) -containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.
- the content of the solid content in the colorant (A1) -containing liquid is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, based on the total amount of the colorant (A1) -containing liquid. It is more preferably 0.1% by mass or more and 99.9% by mass or less, further preferably 0.1% by mass or more and 99% by mass or less, and particularly preferably 1% by mass or more and 90% by mass or less. More preferably, it is 1% by mass or more and 80% by mass or less, particularly preferably 1% by mass or more and 70% by mass or less, extremely preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more. It is 50% by mass or less.
- 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, based on the total amount of solids in the colorant (A1) -containing liquid. .9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 1% by mass or more and 99% by mass or less, and particularly preferably 3% by mass or more and 99% by mass or less. Yes, more preferably 5% by mass or more and 99% by mass or less.
- the colorant (A1) may be treated with rosin, a surface treatment using a derivative having an acidic group or a basic group introduced therein, a graft treatment on the surface of the colorant (A1) with a polymer compound or the like, and sulfuric acid, if necessary.
- Agglomeration treatment by atomization method, cleaning treatment with organic solvent or water to remove impurities, removal treatment by ion exchange method of ionic impurities, atomization, mixing, crystal structure similar to compound (I) Conversion, shaping of the particles and / or substantially uniform treatment of the particle size may be performed.
- the colorant (A1) is mixed with the compound (I), if necessary, and the mixture is subjected to the same atomization, mixing, crystal structure conversion, particle shaping and / or particle size abbreviation as the compound (I). Uniform treatment or the like may be applied.
- the particle size of the colorant (A1) is preferably substantially uniform. When a plurality of types of the colorant (A1), the compound (I) and / or the derivative are used, these treatments may be performed individually, or a plurality of types may be mixed and treated.
- the colorant (A1) can be made into a state in which the colorant (A1) is uniformly dispersed in the colorant (A1) -containing liquid by carrying out the dispersion treatment by containing the dispersant.
- the colorant (A1) may be dispersed individually or a plurality of types may be mixed and dispersed.
- dispersant examples include surfactants and the like, which may be any of cationic, anionic, nonionic and amphoteric surfactants. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark).
- KP manufactured by Shin-Etsu Chemical Industry Co., Ltd.
- Floren manufactured by Kyoeisha Chemical Co., Ltd.
- Solsperse registered trademark
- EFKA registered trademark
- the amount of the dispersant (solid content) used is, for example, 0.01 part by mass or more and 10,000 parts by mass or less with respect to 100 parts by mass of the colorant (A1). It is preferably 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, and further preferably 0.1 parts by mass or more and 500 parts by mass or less. It is particularly preferably 0.1 part by mass or more and 300 parts by mass or less, more preferably 1 part by mass or more and 300 parts by mass or less, and particularly preferably 5 parts by mass or more and 260 parts by mass or less.
- the amount of the dispersant used is in the above range, a more uniform colorant (A1) -containing liquid in a dispersed state tends to be obtained.
- the coloring composition of the present invention contains a resin (B), and a colorant (A1) -containing liquid containing the colorant (A1) and the solvent (E) is prepared in advance, and then the colorant (A1) -containing liquid is used.
- the coloring agent (A1) -containing liquid may contain a part or all, preferably a part of the resin (B) contained in the coloring composition in advance. Good. By including the resin (B) in advance, the dispersion stability of the colorant (A1) -containing liquid can be further improved.
- the content of the resin (B) is, for example, 0.01 part by mass or more and 10,000 parts by mass or less with respect to 100 parts by mass of the colorant (A1). Yes, preferably 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, and further preferably 0.1 parts by mass or more and 500 parts by mass or less, particularly. It is preferably 0.1 part by mass or more and 300 parts by mass or less.
- the coloring composition of the present invention contains a coloring agent (A1)
- the content of the coloring agent (A), which is a combination of the compound (I) and the coloring agent (A1), in the coloring composition is the total amount of solid content.
- it is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, and further preferably 0.0001% by mass.
- % Or more and 90% by mass or less particularly preferably 0.0001% by mass or more and 80% by mass or less, more preferably 0.0001% by mass or more and 70% by mass or less, and particularly preferably 0.0001% by mass or more.
- It is 60% by mass or less, extremely preferably 0.0001% by mass or more and 55% by mass or less, and most preferably 0.1% by mass or more and 55% by mass or less.
- the content of the compound (I) is usually 0.0001% by mass or more based on the total amount of the coloring agent (A), preferably 0. It is 0003% by mass or more, more preferably 0.0005% by mass or more, further preferably 0.001% by mass or more, and the upper limit is less than 100% by mass, preferably 99.9999% by mass or less. , More preferably 99% by mass or less, further preferably 98% by mass or less, and particularly preferably 97% by mass or less.
- Leveling agent (F) examples include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
- silicone-based surfactant examples include surfactants having a siloxane bond in the molecule.
- Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK) and the like. ..
- fluorine-based surfactant examples include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554.
- R30, RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).
- silicone-based surfactant having a fluorine atom examples include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include MegaFvck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).
- the content thereof is usually 0.00001% by mass or more and 5% by mass or less, preferably 0.00001% by mass or more and 3% by mass or less, based on the total amount of the coloring composition. It is more preferably 0.0001% by mass or more and 2% by mass or less, and further preferably 0.0001% by mass or more and 1% by mass or less.
- the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
- antioxidant From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more.
- the antioxidant is not particularly limited as long as it is an antioxidant that is generally used industrially, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, or the like can be used.
- phenolic antioxidant examples include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], manufactured by BASF), Irganox 1076.
- Irganox 1076 octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF
- Irganox 1330 Irganox 1330: 3,3', 3'', 5,5' , 5''-Hexa-tert-butyl-a, a', a''-(methicylene-2,4,6-triyl) tri-p-cresol, manufactured by BASF
- Irganox 3114 Irganox 3114: 1, 3,5-Tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trion, manufactured by BASF
- Irga Knox 3790 Irganox 3790: 1,3,5-tris ((4-tert-butyl-3-hydroxy-2,6-xysilyl) methyl) -1,
- 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].
- Irgafos 38 Bis (2,4-bis (1,1-dimethylethyl) -6-methylphenyl) ethyl ester phosphite, manufactured by BASF), Adecastab 329K (manufactured by ADEKA Co., Ltd.), Adecaster PEP36 (manufactured by ADEKA Co., Ltd.) , Adecastab PEP-8 (manufactured by ADEKA Co., Ltd.), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (Weston 618, manufactured by GE), Weston 619G (manufactured by Weston 619G, manufactured by GE), Ultranox 626 (Ultranox) 626, manufactured by
- sulfur-based antioxidant examples include ⁇ -alkyl mercaptopropion of a dialkylthiodipropionate compound such as dilauryl thiodipropionate, dimyristyl or distearyl, and a polyol such as tetrakis [methylene (3-dodecylthio) propionate] methane. Examples thereof include acid ester compounds.
- the coloring composition of the present invention may contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, light stabilizers, and chain transfer agents.
- adhesion accelerator include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycid.
- the coloring composition of the present invention includes, for example, compound (I), solvent (E), and, if necessary, resin (B), polymerizable compound (C), polymerization initiator (D), and polymerization initiator. It can be prepared by mixing (D1), a colorant (A1), a leveling agent (F), an antioxidant (G) and / or other components. Mixing can be carried out by known or conventional equipment and conditions. Compound (I) was previously mixed with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size of compound (I) was about 0.2 ⁇ m or less. It is preferable to use it in the state of the containing liquid.
- a part or all of the dispersant and the resin (B) may be blended.
- the colorant (A1) is mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the colorant (A1) is about 0.2 ⁇ m or less.
- (A1) It is preferable to use it in the state of the containing liquid.
- a part or all of the dispersant and the resin (B) may be blended.
- Compound (I) is preferably used in the state of a solution previously dissolved in a part or all of the solvent (E) (the solution is contained in the compound (I) -containing solution).
- the colorant (A1) is preferably used in the state of a solution previously dissolved in a part or all of the solvent (E) (the solution is contained in the colorant (A1) -containing solution). Further, it is preferable to filter the colorant (A1) -containing liquid with a filter having a pore size of 0.01 ⁇ m or more and 1 ⁇ m or less.
- the colored composition after mixing is preferably filtered through a filter having a pore size of 0.01 ⁇ m or more and 10 ⁇ m or less.
- a color filter can be formed from the coloring composition of the present invention.
- a colored coating film can be formed by applying the coloring composition to a substrate, removing volatile components such as a solvent, and drying the substrate.
- the colored coating film thus formed is included in the color filter of the present invention.
- Examples of the method for forming the colored pattern include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable.
- the photolithography method is a method in which the coloring composition is applied to a substrate and dried to form a coloring composition layer, and the coloring composition layer is exposed and developed through a photomask.
- a colored coating film which is a cured product of the coloring composition layer can be formed by not using a photomask at the time of exposure and / or not developing.
- the colored pattern or colored coating film thus formed is the color filter of the present invention.
- the film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, it is 0.1 to 30 ⁇ m, preferably 0.1 to 20 ⁇ m, and more preferably 0.1 to 20 ⁇ m. Is 0.5 to 6 ⁇ m.
- a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate.
- Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass.
- Another color filter layer, resin layer, transistor, circuit, etc. may be formed on these substrates.
- each color pixel by the photolithography method can be performed by a known or conventional device or condition.
- it can be produced as follows.
- the coloring composition is applied onto a substrate and dried by heating and drying (pre-baking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth coloring composition layer.
- the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
- the temperature at the time of heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C.
- the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
- the film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.
- the coloring composition layer is then exposed via a photomask to form the desired coloring pattern.
- the pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
- a light source used for exposure a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it.
- Specific examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp and a halogen lamp.
- An exposure device such as a mask aligner and a stepper is used because it is possible to uniformly irradiate the entire exposed surface with parallel light rays and accurately align the photomask with the substrate on which the coloring composition layer is formed. Is preferable.
- a coloring pattern is formed on the substrate by developing the coloring composition layer after exposure in contact with a developing solution.
- a developing solution for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide is preferable.
- the concentration of the alkaline compound is preferably 0.01 to 10% by mass, more preferably 0.02 to 5% by mass.
- the developer may contain a surfactant.
- the developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
- the developed substrate is preferably washed with water. Further, it is preferable to post-bake the obtained coloring pattern.
- the post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C.
- the post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.
- the colored pattern or the color filter which is the colored coating film thus obtained may be further subjected to a surface coating treatment in order to impart various characteristics.
- the color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state imaging device, and particularly as a color filter used in a liquid crystal display device.
- a display device for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.
- a solid-state imaging device for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.
- the polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
- Detector RI
- Calibration standard material TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
- the ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight (Mw) and the number average molecular weight (Mn) obtained above was defined as the degree of dispersion.
- 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.) 6.92 parts (manufactured by Tokyo Chemical Industry Co., Ltd.) and 40.4 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed. The mixture was stirred for 9 hours, keeping at 170 ° C. To this mixture was added 7.83 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.).
- Synthesis example 1 An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was placed therein, and the mixture was heated to 80 ° C. with stirring. Then 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2.1.0 2,6 ] .
- Synthesis example 2 An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 340 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring. Then 57 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2.1.0 2,6 ] .
- Example 2 Each component was mixed at the following ratios, and the colorant was dispersed using a bead mill to obtain a coloring composition M1.
- Colorant (A) 4.50 parts of the compound represented by the formula (Ia3); Colorant (A): 0.500 parts of the compound represented by the formula (z);
- Dispersant solution DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.) 16.7 copies;
- Solvent (E) 20.0 parts of ethyl lactate;
- the coloring composition 1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a prebaked colored coating film.
- the film thickness of the obtained pre-baked colored coating film was measured using Dektak XT (manufactured by Bruker).
- the spectrum of this pre-baked colored coating film was measured using a colorimeter: LVmicr formatZ (manufactured by Lambda Vision Co., Ltd.).
- Table 31 shows the film thickness of the pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked colored coating film.
- This pre-baked colored coating film was post-baked at 230 ° C. for 30 minutes to obtain a post-baked colored coating film.
- Coloring composition M2 24.0 parts; Resin (B): 35.0 parts of resin B2 solution; Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts; Leveling agent (F): Torre Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 copies;
- the coloring composition 2 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a prebaked colored coating film.
- the film thickness of the obtained pre-baked colored coating film was measured using Dektak XT (manufactured by Bruker).
- the spectrum of this pre-baked colored coating film was measured using a colorimeter: LVmicr formatZ (manufactured by Lambda Vision Co., Ltd.).
- Table 31 shows the film thickness of the pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked colored coating film.
- This pre-baked colored coating film was post-baked at 230 ° C. for 30 minutes to obtain a post-baked colored coating film.
- the coloring composition 3 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a prebaked colored coating film.
- the film thickness of the obtained pre-baked colored coating film was measured using Dektak XT (manufactured by Bruker).
- the spectrum of this pre-baked colored coating film was measured using a colorimeter: LVmicr formatZ (manufactured by Lambda Vision Co., Ltd.).
- Table 31 shows the film thickness of the pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked colored coating film.
- This pre-baked colored coating film was post-baked at 230 ° C. for 30 minutes to obtain a post-baked colored coating film.
- the “AAA” column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum.
- the “BBB” column indicates the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
- 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 determined by C.I. I. It was found that the wavelength was longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing Pigment Yellow 138.
- the coloring composition and compound of the present invention are described in C.I. I. Since it can be used for forming a darker color filter than a coloring composition containing Pigment Yellow 138, it is suitably used for display devices such as color filters and liquid crystal display devices.
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Abstract
Description
上記の吸収スペクトルの最も長波長側の肩ピークの波長とは、
化合物が、
・C.I.ピグメントイエロー138の吸収スペクトルの最も長波長側の極大吸収波長よりも長波長側に、吸収スペクトルの最も長波長側の極大吸収波長を有さない場合で、
かつ、
・吸収スペクトルの最も長波長側の極大吸収波長よりも長波長側に、吸収スペクトルの変曲点を2つ以上有する場合に、
吸収スペクトルの最も長波長側の変曲点の波長と、吸収スペクトルの2番目に長波長側の変曲点の波長の平均値の波長を意味する。
[1] 下記式(I)で表される化合物と溶剤とを含む着色組成物。
[式(I)中、
R1~R5は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
R1及びR2、R2及びR3、R3及びR4、及びR4及びR5は、それぞれ互いに結合して環を形成していてもよい。
Mは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
MMは、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
Z1~Z4は、それぞれ独立して、水素原子、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
Q1及びQ2は、それぞれ独立して、2価の炭化水素基又は2価の複素環基を表し、
該2価の炭化水素基及び該2価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
ただし、Q1及びQ2の少なくとも一つは、式(y)で表される基を有する。
Y1は、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
※は結合手を表す。
Z1~Z4、式(y)で表される基、Y1、M及びMMがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてもよい。]
[2] 樹脂を含む[1]に記載の着色組成物。
[3] 重合性化合物と重合開始剤とを含む[1]又は[2]に記載の着色組成物。
[4] [1]~[3]のいずれかに記載の着色組成物により形成されるカラーフィルタ。
[5] [4]に記載のカラーフィルタを含む表示装置。
[6] 式(I)で表される化合物。
[式(I)中、 R1~R5は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
R1及びR2、R2及びR3、R3及びR4、及びR4及びR5は、それぞれ互いに結合して環を形成していてもよい。
Mは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
MMは、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
Z1~Z4は、それぞれ独立して、水素原子、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
Q1及びQ2は、それぞれ独立して、2価の炭化水素基又は2価の複素環基を表し、
該2価の炭化水素基及び該2価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
ただし、Q1及びQ2の少なくとも一つは、式(y)で表される基を有する。
Y1は、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
※は結合手を表す。
Z1~Z4、式(y)で表される基、Y1、M及びMMがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてもよい。]
本発明の着色組成物は、式(I)で表される化合物(以下、化合物(I)という場合がある。)と、溶剤(以下、溶剤(E)という場合がある。)とを含む。
[式(I)中、
R1~R5は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
R1及びR2、R2及びR3、R3及びR4、及びR4及びR5は、それぞれ互いに結合して環を形成していてもよい。
Mは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
MMは、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
Z1~Z4は、それぞれ独立して、水素原子、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
Q1及びQ2は、それぞれ独立して、2価の炭化水素基又は2価の複素環基を表し、
該2価の炭化水素基及び該2価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
ただし、Q1及びQ2の少なくとも一つは、式(y)で表される基を有する。
Y1は、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
※は結合手を表す。
Z1~Z4、式(y)で表される基、Y1、M及びMMがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてもよい。]
化合物(I)は、着色剤として使用することができる。
本発明の着色組成物には、1種又は2種以上の化合物(I)が含まれていてもよい。
本発明の着色組成物は、樹脂(以下、樹脂(B)という場合がある。)を含んでいてもよい。
本発明の着色組成物は、重合性化合物(以下、重合性化合物(C)という場合がある。)を含んでいてもよい。
本発明の着色組成物は、重合開始剤(以下、重合開始剤(D)という場合がある。)を含んでいてもよい。
本発明の着色組成物は、重合開始助剤(以下、重合開始助剤(D1)という場合がある。)を含んでいてもよい。
本発明の着色組成物は、化合物(I)以外の着色剤(以下、着色剤(A1)という場合がある。そして以下では、化合物(I)及び着色剤(A1)を「着色剤(A)」と総称する場合がある。)を含んでいてもよい。
着色剤(A1)には、1種又は2種以上の着色剤が含まれていてもよい。
着色剤(A1)は、黄色着色剤、橙色着色剤、赤色着色剤及び緑色着色剤から選ばれる1種以上を含むことが好ましい。
本発明の着色組成物は、レベリング剤(以下、レベリング剤(F)という場合がある。)を含んでいてもよい。
本発明の着色組成物は、酸化防止剤(以下、酸化防止剤(G)という場合がある。)を含んでいてもよい。
以下、化合物(I)の部分構造を挙げて本発明をより具体的に説明するが、各部分構造において、環構造に結合する置換基が、環構造のいずれかの部位で結合するものしか例示されていなくても、以下の例示には、該置換基が、環構造のすべての部位に、それぞれ結合する態様が含まれる。1つまたは2つ以上の置換基が環構造に結合していてもよく、2つ以上の置換基が環構造に結合する場合、該置換基はそれぞれ、同じであってもよく異なっていてもよい。
R1~R5、Z1~Z4及びY1で表される炭素数1~40の1価の炭化水素基は、脂肪族炭化水素基及び芳香族炭化水素基であってもよく、該脂肪族炭化水素基は、飽和又は不飽和であってもよく、鎖状(鎖状炭化水素基)又は環状(脂環式炭化水素基)であってもよい。
イソプロピル基、イソブチル基、sec-ブチル基、tert-ブチル基、2-エチルブチル基、3,3-ジメチルブチル基、1,1,3,3-テトラメチルブチル基、1-メチルブチル基、1-エチルプロピル基、3-メチルブチル基、ネオペンチル基、1,1-ジメチルプロピル基、2-メチルペンチル基、3-エチルペンチル基、1,3-ジメチルブチル基、2-プロピルペンチル基、1-エチル-1,2-ジメチルプロピル基、1-メチルペンチル基、4-メチルペンチル基、4-メチルヘキシル基、5-メチルヘキシル基、2-エチルヘキシル基、1-メチルヘキシル基、1-エチルペンチル基、1-プロピルブチル基、3-エチルヘプチル基、2,2-ジメチルヘプチル基、1-メチルヘプチル基、1-エチルヘキシル基、1-プロピルペンチル基、1-メチルオクチル基、1-エチルヘプチル基、1-プロピルヘキシル基、1-ブチルペンチル基、1-メチルノニル基、1-エチルオクチル基、1-プロピルヘプチル基及び1-ブチルヘキシル基等の分枝鎖状アルキル基;
エテニル基(ビニル基)、プロペニル基(例えば、1-プロペニル基、2-プロペニル基(アリル基))、1-メチルエテニル基、ブテニル基(例えば、1-ブテニル基、2-ブテニル基、3-ブテニル基)、3-メチル-1-ブテニル基、1,3-ブタジエニル基、1-(2-プロペニル)エテニル基、1-(1-メチルエテニル)エテニル基、1,2-ジメチル-1-プロペニル基、ペンテニル基(例えば、1-ペンテニル基、2-ペンテニル基、3-ペンテニル基、4-ペンテニル基)、1-(1,1-ジメチルエチル)エテニル基、1,3-ジメチル-1-ブテニル基、ヘキセニル基(例えば、1-ヘキセニル基、5-ヘキセニル基)、ヘプテニル基(例えば、1-ヘプテニル基、6-ヘプテニル基)、オクテニル基(例えば、1-オクテニル基、7-オクテニル基)、ノネニル基(例えば、1-ノネニル基、8-ノネニル基)、デセニル基(例えば、1-デセニル基、9-デセニル基)、ウンデセニル基、ドデセニル基、トリデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデセニル基、ノナデセニル基、イコセニル基、1,1-ジメチル-2-プロペニル基、1-エチル-2-プロペニル基及び1-メチル-1-ブテニル基等のアルケニル基;
エチニル基、プロピニル基(例えば、1-プロピニル基、2-プロピニル基)、オクチニル基(例えば、1-オクチニル基、7-オクチニル基)、ブチニル基、ペンチニル基、ヘキシニル基、ヘプチニル基、ノニニル基、デシニル基、ウンデシニル基、ドデシニル基、トリデシニル基、テトラデシニル基、ペンタデシニル基、ヘキサデシニル基、ヘプタデシニル基、オクタデシニル基、ノナデシニル基及びイコシニル基等のアルキニル基;等が挙げられる。
飽和鎖状炭化水素基の炭素数は、好ましくは1~30であり、より好ましくは1~20であり、さらに好ましくは1~18であり、とりわけ好ましくは1~12である。
不飽和鎖状炭化水素基の炭素数は、好ましくは2~30であり、より好ましくは2~20であり、さらに好ましくは2~18であり、とりわけ好ましくは2~12である。
中でも、炭素数1~12の直鎖状又は分岐鎖状アルキル基であることが特に好ましい。
飽和又は不飽和脂環式炭化水素基の炭素数は、好ましくは3~30であり、より好ましくは3~20であり、さらに好ましくは3~18であり、とりわけ好ましくは3~12である。中でも、シクロペンチル基、シクロヘキシル基、シクロへプチル基、シクロオクチル基、アダマンチル基であることが特に好ましい。
1-フェニルエテニル基、2-フェニルエテニル基(フェニルビニル基)、2,2-ジフェニルエテニル基、2-フェニル-2-(1-ナフチル)エテニル基等のアリールアルケニル基;
フェニルエチニル基、
等のアリールアルキニル基;
ビフェニリル基、ターフェニリル基等の1つ以上のフェニル基が結合したフェニル基;
シクロヘキシルメチルフェニル基、ベンジルフェニル基、(ジメチル(フェニル)メチル)フェニル基、
等が挙げられる。
※は結合手を表す。
R1~R5、Z1~Z4及びY1で表される基は、上記に挙げた炭化水素基(例えば鎖状炭化水素基と脂環式炭化水素基)を組合せた基、例えば、シクロプロピルメチル基、シクロプロピルエチル基、シクロブチルメチル基、シクロブチルエチル基、シクロペンチルメチル基、シクロペンチルエチル基、シクロヘキシルメチル基、(2-メチルシクロヘキシル)メチル基、シクロヘキシルエチル基、アダマンチルメチル基等の1つ以上の脂環式炭化水素基が結合したアルキル基であってもよい。
これらの炭素数は、好ましくは4~30であり、より好ましくは4~20であり、さらに好ましくは4~18であり、とりわけ好ましくは4~12である。
複素環基の炭素数は、好ましくは3~30であり、より好ましくは3~20であり、さらに好ましくは3~18であり、とりわけ好ましくは3~12である。
アジリジン、アゼチジン、ピロリジン、ピペリジン及びピペラジン等の単環系飽和複素環;
ピロール、1-メチルピロール、2,5-ジメチルピロール等のピロール、ピラゾール、1-メチルピラゾール、2-メチルピラゾール、3-メチルピラゾール、4-メチルピラゾール、5-メチルピラゾール等のピラゾール、イミダゾール、1,2,3-トリアゾール及び1,2,4-トリアゾール等の5員環系不飽和複素環;
ピリジン、ピリダジン、ピリジミン、6-メチルピリミジン等のピリミジン、ピラジン及び1,3,5-トリアジン等の6員環系不飽和複素環;
インダゾール、インドリン、イソインドリン、インドール、インドリジン、ベンゾイミダゾール、キノリン、イソキノリン、5,6,7,8-テトラヒドロ(3-メチル)キノキサリン、3-メチルキノキサリン等のキノキサリン、キナゾリン、シンノリン、フタラジン、ナフチリジン、プリン、プテリジン、ベンゾピラゾール、ベンゾピペリジン等の縮合二環系複素環;
カルバゾール、アクリジン及びフェナジン等の縮合三環系複素環;等が挙げられる。
オキシラン、オキセタン、テトラヒドロフラン、テトラヒドロピラン、1,3-ジオキサン及び1,4-ジオキサン、1-シクロペンチルジオキソラン、2-シクロペンチルジオキソラン等の単環系飽和複素環;
1,4-ジオキサスピロ[4.5]デカン、1,4-ジオキサスピロ[4.5]ノナン、1,4-ジオキサスピロ[4.4]ノナン等の二環系飽和複素環;
α-アセトラクトン、β-プロピオラクトン、γ-ブチロラクトン、γ-バレロラクトン及びδ-バレロラクトン等のラクトン系複素環;
フラン、2,3-ジメチルフラン、2,5-ジメチルフラン等のフラン等の5員環系不飽和複素環;
2H-ピラン、4H-ピラン等の6員環系不飽和複素環;
1-ベンゾフラン等のベンゾフラン、ベンゾピラン、4-メチルベンゾピラン等のベンゾピラン、ベンゾジオキソール、1,3-ベンゾジオキソール、ベンゾジオキサン、クロマン及びイソクロマン等の縮合二環系複素環;
キサンテン、ジベンゾフラン等の縮合三環系複素環;
無水フタル酸等の酸無水物系複素環;等が挙げられる。
ジチオラン等の5員環系飽和複素環;
チアン、1,3-ジチアン、2-メチル-1,3-ジチアン等の6員環系飽和複素環;
チオフェン、3-メチルチオフェン、2-カルボキシチオフェン等のチオフェン、2H-チオピラン、4H-チオピラン等のチオピラン、ベンゾテトラヒドロチオピラン等のベンゾチオピラン等の5員環系不飽和複素環及び6員環系不飽和複素環;
ベンゾチオピラン、ベンゾテトラヒドロチオピラン等のベンゾチオピラン、ベンゾチオフェン等の縮合二環系複素環等;
チアントレン、ジベンゾチオフェン等の縮合三環系複素環;等が挙げられる。
モルホリン、2-ピロリドン、1-メチル-2-ピロリドン、2-メチル-2-ピロリドン、2-ピペリドン、1-メチル-2-ピペリドン及び2-メチル-2-ピペリドン等の単環系飽和複素環;
オキサゾール、4-メチルオキサゾール等のオキサゾール、2-メチルイソオキサゾール、3-メチルイソオキサゾール、4-メチルイソオキサゾール、5-メチルイソオキサゾール等のイソオキサゾール等の単環系不飽和複素環;
ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾオキサジン、ベンゾジオキサン、ベンゾイミダゾリン等の縮合二環系複素環;
フェノキサジン等の縮合三環系複素環;等が挙げられる。
チアゾール、2-メチルチアゾール、3-メチルチアゾール、4-メチルチアゾール、5-メチルチアゾール、2,4-ジメチルチアゾール等のチアゾール等の単環系複素環;
ベンゾチアゾール等の縮合二環系複素環;
フェノチアジン等の縮合三環系複素環;等が挙げられる。
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。このような基としては、以下の基が挙げられる。
-CH2CH2OCH2CH3、-CH2CH2O(CH2)3CH3、-(CH2CH2O)2CH2CH3、-(CH2CH2O)3CH2CH3、-(CH2CH2O)4CH2CH3、-(CH2CH2O)5CH2CH3、-(CH2CH2O)6CH2CH3、-(CH2CH2O)7CH2CH3、-(CH2CH2O)8CH2CH3、-(CH2CH2O)9CH2CH3、-(CH2CH2O)10CH2CH3、-(CH2CH2O)11CH2CH3、-(CH2CH2O)12CH2CH3、-(CH2CH2O)13CH3、-CH2CH2OH、-(CH2CH2O)2H、-(CH2CH2O)3H、-(CH2CH2O)4H、-(CH2CH2O)5H、-(CH2CH2O)6H、-(CH2CH2O)7H、-(CH2CH2O)8H、-(CH2CH2O)9H、-(CH2CH2O)10H、-(CH2CH2O)11H、-(CH2CH2O)12H、-(CH2CH2O)13H、-CH2CH2OCH3、-(CH2CH2O)2CH3、-(CH2CH2O)3CH3、-(CH2CH2O)4CH3、-(CH2CH2O)5CH3、-(CH2CH2O)6CH3、-(CH2CH2O)7CH3、-(CH2CH2O)8CH3、-(CH2CH2O)9CH3、-(CH2CH2O)10CH3、-(CH2CH2O)11CH3、-(CH2CH2O)12CH3、-(CH2CH2O)13CH3等の上記の1価の炭化水素基又は1価の複素環基の-CH2-が-O-に置き換わった基;
等の置換基を有するアルキル基(以下、これらを群Aの基という場合がある)が挙げられる。
及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が結合したカルボニル基等が挙げられ、
炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニル基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニル基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニル基がとりわけ好ましい。
※は、結合手を表す。
及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が結合したオキシカルボニル基等が挙げられ、
炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したオキシカルボニル基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したオキシカルボニル基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したオキシカルボニル基がとりわけ好ましい。
※は、結合手を表す。
炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニルオキシ基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニルオキシ基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニルオキシ基がとりわけ好ましい。
トリクロロメトキシ基、トリフルオロメトキシ基、2,2,2-トリフルオロエトキシ基、2,2,3,3-テトラフルオロプロポキシ基、3,3,3-トリフルオロ-2-トリフルオロメチル-2-メチルプロポキシ基、2-ブトキシエトキシ基、2-ニトロプロポキシ基、-OCH2CH2OH、-O(CH2CH2O)4H、-OCH2CF2CF2H、-OCH2CH2O(CH2)3CH3、-OCH2CH2OCH2CH3、-O(CH2CH2O)2CH2CH3、-O(CH2CH2O)4CH2CH3、-OCH2CH2O(CH2)3CH3、
及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が結合したオキシ基等が挙げられ、
炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したオキシ基、又はヒドロキシ基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したオキシ基、又はヒドロキシ基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したオキシ基、又はヒドロキシ基がとりわけ好ましい。
※は、結合手を表す。
及び、水素原子が上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基に置換したメルカプト基等が挙げられ、
水素原子が炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものに置換したメルカプト基、又はメルカプト基がより好ましく、
水素原子が炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものに置換したメルカプト基、又はメルカプト基がさらに好ましく、
水素原子が炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものに置換したメルカプト基、又はメルカプト基がとりわけ好ましい。
※は、結合手を表す。
及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が結合したスルホニル基等が挙げられ、
炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したスルホニル基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したスルホニル基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したスルホニル基がとりわけ好ましい。
※は、結合手を表す。
スルファモイル基;
N-メチルスルファモイル基、N-エチルスルファモイル基、N-プロピルスルファモイル基、N-イソプロピルスルファモイル基、N-ブチルスルファモイル基、N-イソブチルスルファモイル基、N-(sec-ブチル)スルファモイル基、N-(tert-ブチル)スルファモイル基、N-ペンチルスルファモイル基、N-(1-エチルプロピル)スルファモイル基、N-ヘキシルスルファモイル基、N-(2-エチルヘキシル)スルファモイル基、N-ヘプチルスルファモイル基、N-オクチルスルファモイル基、N-ノニルスルファモイル基、N-デシルスルファモイル基、N-ウンデシルスルファモイル基、N-ドデシルスルファモイル基、N-イコシルスルファモイル基、N-フェニルスルファモイル基、-SO2NH(CH2)2N(CH2CH3)2、-SO2NHCH2CH2CH2Si(OCH2CH3)3、及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が1つ置換したスルファモイル基等;
炭素数1~20の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したスルファモイル基、-SO2NH(CH2)2N(CH2CH3)2又はスルファモイル基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したスルファモイル基、-SO2NH(CH2)2N(CH2CH3)2又はスルファモイル基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したスルファモイル基、-SO2NH(CH2)2N(CH2CH3)2又はスルファモイル基がとりわけ好ましい。
カルバモイル基;
N-メチルカルバモイル基、N-エチルカルバモイル基、N-プロピルカルバモイル基、N-イソプロピルカルバモイル基、N-ブチルカルバモイル基、N-イソブチルカルバモイル基、N-(sec-ブチル)カルバモイル基、N-(tert-ブチル)カルバモイル基、N-ペンチルカルバモイル基、N-(1-エチルプロピル)カルバモイル基、N-ヘキシルカルバモイル基、N-(2-エチルヘキシル)カルバモイル基、N-ヘプチルカルバモイル基、N-オクチルカルバモイル基、N-ノニルカルバモイル基、N-デシルカルバモイル基、N-ウンデシルカルバモイル基、N-ドデシルカルバモイル基、N-イコシルカルバモイル基、N-フェニルカルバモイル基、-CONH(CH2)2N(CH2CH3)2、-CONHCH2CH2CH2Si(OCH2CH3)3、及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が1つ置換したカルバモイル基等;
炭素数1~20の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したカルバモイル基、又はカルバモイル基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したカルバモイル基、又はカルバモイル基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したカルバモイル基、又はカルバモイル基がとりわけ好ましい。
アミノ基;
N-メチルアミノ基、N-エチルアミノ基、N-プロピルアミノ基、N-イソプロピルアミノ基、N-ブチルアミノ基、N-イソブチルアミノ基、N-(sec-ブチル)アミノ基、N-(tert-ブチル)アミノ基、N-ペンチルアミノ基、N-(1-エチルプロピル)アミノ基、N-ヘキシルアミノ基、N-(2-エチルヘキシル)アミノ基、N-ヘプチルアミノ基、N-オクチルアミノ基、N-ノニルアミノ基、N-デシルアミノ基、N-ウンデシルアミノ基、N-ドデシルアミノ基、N-イコシルアミノ基、N-フェニルアミノ基、及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が1つ置換したアミノ基等;
炭素数1~20の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したアミノ基、又はアミノ基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したアミノ基、又はアミノ基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ又は2つが置換したアミノ基、又はアミノ基がとりわけ好ましい。
及び、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基が結合したカルボニルアミノ基等が挙げられ、
炭素数1~20の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニルアミノ基がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニルアミノ基がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基或いは上記の1価の炭化水素基又は1価の複素環基の好ましいものが結合したカルボニルアミノ基がとりわけ好ましい。
※は、結合手を表す。
-SiH3;-Si(CH3)3、-Si(CH2CH3)3、-Si((CH2)2CH3)3、-Si(CH(CH3)2)3、-Si((CH2)3CH3)3、-Si((CH2)4CH3)3、-Si((CH2)5CH3)3、-Si((CH2)6CH3)3、-Si((CH2)7CH3)3、-Si((CH2)8CH3)3、-Si((CH2)9CH3)3、-Si((CH2)10CH3)3、-Si((CH2)11CH3)3、-Si((CH2)12CH3)3、-Si(C6H5)3、-Si(C10H7)3、-Si(CH3)2(CH2CH3)、-Si(CH3)2((CH2)2CH3)、-Si(CH3)2(CH(CH3)2)、-Si(CH3)2((CH2)3CH3) 、-Si(CH3)2((CH2)5CH3)、-Si(CH3)2((CH2)7CH3)、-Si(CH3)2((CH2)9CH3)、-Si(CH3)2((CH2)11CH3)、-Si(CH3)2((CH2)13CH3)、-Si(CH3)2((CH2)15CH3)、-Si(CH3)2((CH2)17CH3)、-Si(CH3)2((CH2)19CH3)、-Si(CH3)2((CH2)29CH3)、-Si(CH3)2(C6H5)、-Si(CH3)(C6H5)2、-Si(CH3)2(C10H7)、及び、上記の群A~Bの基、上記の1価の炭化水素基及び上記の1価の複素環基より選ばれる1つ、2つ又は3つが置換した-SiH3等;
炭素数1~20の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ、2つ又は3つが置換した-SiH3、-Si(OH)3、-SiH(OH)2及び-SiH2(OH)、又は-Si(OH)3がより好ましく、
炭素数1~18の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ、2つ又は3つが置換した-SiH3、-Si(OH)3、-SiH(OH)2及び-SiH2(OH)、又は-Si(OH)3がさらに好ましく、
炭素数1~12の炭化水素基、上記の群A~Bの基、上記の1価の炭化水素基の好ましいもの及び上記の1価の複素環基の好ましいものより選ばれる1つ、2つ又は3つが置換した-SiH3、-Si(OH)3、-SiH(OH)2及び-SiH2(OH)、又は-Si(OH)3がとりわけ好ましい。
該金属原子に配位している配位子と、同一の配位子に含まれる炭素原子、窒素原子、酸素原子又は硫黄原子等が、同一の金属原子に配位していてもよく、
該金属原子に、複数の異なる配位子が、同一の金属原子へ配位していてもよく、オリゴマー又はポリマーを形成していてもよい。
該配位子には、化合物(I)が配位子を有していてもよい金属原子を含む場合、配位子を有していてもよい金属原子を除いた化合物(I)も含有される。
本発明の化合物(I)には、このようなオリゴマー又はポリマーも含有される。
ただし、化合物(I)の電荷は0である。
ただし、式(EN1)~式(EN5)中、( )内で示されている構造がオリゴマー及びポリマーのように、繰り返し結合していることを示す。
例えば、式(EN1)で表される金属塩は、同一の金属原子に同一の配位子が配位しているものを示す。
例えば、式(EN2)~式(EN3)で表される金属塩は、同一の金属原子に複数の異なる配位子が配位しているものを示す。
例えば、式(EN4)~式(EN5)で表される金属塩は、同一の金属原子に複数の異なる配位子が配位してオリゴマー又はポリマーを形成しているものを示す。
NH4;NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等のNH4にアルキル基が1つ置換した基;
N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等のNH4にアルキル基が4つ置換した基;
及び、上記の群A~Bの基、上記の1価の炭化水素基及び上記の1価の複素環基より選ばれる1つ、2つ、3つ又は4つが置換したNH4
等が挙げられる。
水素原子;
アルカリ金属原子;
配位子を有していてもよいMg、配位子を有していてもよいCa、配位子を有していてもよいSr、配位子を有していてもよいBa、配位子を有していてもよいNi、配位子を有していてもよいZn、配位子を有していてもよいCu、配位子を有していてもよいFe、配位子を有していてもよいCo、配位子を有していてもよいSn、配位子を有していてもよいMn、配位子を有していてもよいAl、配位子を有していてもよいCr;
NH4;
NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等のNH4にアルキル基が1つ置換した基;
N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等のNH4にアルキル基が4つ置換した基
が好ましく、
ナトリウム原子、カリウム原子;
配位子を有していてもよいMg、配位子を有していてもよいCa、配位子を有していてもよいSr、配位子を有していてもよいBa、配位子を有していてもよいNi、配位子を有していてもよいZn、配位子を有していてもよいCu、配位子を有していてもよいFe、配位子を有していてもよいCo、配位子を有していてもよいMn、配位子を有していてもよいAl、配位子を有していてもよいCr;
NH4;
NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等のNH4にアルキル基が1つ置換した基;
N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等のNH4にアルキル基が4つ置換した基
がより好ましい。
アルカリ金属原子;
配位子を有していてもよいMg、配位子を有していてもよいCa、配位子を有していてもよいSr、配位子を有していてもよいBa、配位子を有していてもよいNi、配位子を有していてもよいZn、配位子を有していてもよいCu、配位子を有していてもよいFe、配位子を有していてもよいCo、配位子を有していてもよいSn、配位子を有していてもよいMn、配位子を有していてもよいAl、配位子を有していてもよいCr;
NH4;
NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等のNH4にアルキル基が1つ置換した基;
N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等のNH4にアルキル基が4つ置換した基
が好ましく、
配位子を有していてもよいMg、配位子を有していてもよいCa、配位子を有していてもよいSr、配位子を有していてもよいBa、配位子を有していてもよいNi、配位子を有していてもよいZn、配位子を有していてもよいCu、配位子を有していてもよいFe、配位子を有していてもよいCo、配位子を有していてもよいMn、配位子を有していてもよいAl、配位子を有していてもよいCr;
NH4;
NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等のNH4にアルキル基が1つ置換した基;
N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等のNH4にアルキル基が4つ置換した基
がより好ましい。
該2価の炭化水素基及び該2価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
ただし、Q1及びQ2の少なくとも一つは、式(y)で表される基を有する。
Y1は、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
※は結合手を表す。
該2価の炭化水素基及び該2価の複素環基を構成する水素原子を置き換える基は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又は式(y)で表される基であってもよく、ハロゲン原子、シアノ基、ニトロ基、-SO3H、-CO2H又は式(y)で表される基であってもよい。
Q1及びQ2は、同一であってもよく異なっていてもよく、同一であることが好ましい。
Q1及びQ2は、式(QQ1)~式(QQ19)で表される基であることが好ましい。
RQ1~RQ94は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、式(y)で表される基、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
RQ1~RQ94は、それぞれ互いにRQ1~RQ94から選ばれる1つ以上と結合して環を形成してもよい。
M、MM、Z1~Z4、式(y)で表される基及びY1は、前記と同一の意味を表す。
※は、結合手を表す。]
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
としては、
R1~R5、Z1~Z4及びY1で表される炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基であり、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
と同じものが挙げられる。
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
の好ましいものとしては、
R1~R5、Z1~Z4及びY1で表される炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基であり、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基の好ましいものと同じものが挙げられる。
式(QQ1)~(QQ19)のそれぞれは、エチニレン基を少なくとも1つ含むことが好ましく、式(y)で表される基を有することがより好ましい。
式(QQ1)~式(QQ12)で表される基であることが好ましく、
式(QQ1)~式(QQ5)で表される基であることがより好ましく、
式(QQ1)~式(QQ4)で表される基であることがさらに好ましく、
式(QQ1)及び式(QQ2)で表される基であることがとりわけ好ましく、式(QQ1)で表される基であることが一層好ましい。
[式(I’)中、
R1~R5は、それぞれ前記と同じ意味を表す。
R6~R13は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、式(y)で表される基、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
R6及びR7、R7及びR8、R8及びR9、R10及びR11、R11及びR12、及びR12及びR13は、それぞれ互いに結合して環を形成していてもよい。
ただし、R6~R13の少なくとも1つは、式(y)で表される基である。]
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
としては、
R1~R5、Z1~Z4及びY1で表される炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基であり、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
と同じものが挙げられる。
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
の好ましいものとしては、
R1~R5、Z1~Z4及びY1で表される炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基であり、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい基
の好ましいものと同じものが挙げられる。
R6~R9の少なくとも1つは、式(y)で表される基であることが好ましく、R10~R13の少なくとも1つは、式(y)で表される基であることが好ましく、R6~R9の少なくとも1つは、式(y)で表される基であり、且つR10~R13の少なくとも1つは、式(y)で表される基であることがより好ましい。
なお、表1~表7中の「Q1」欄及び「Q2」欄に記載されている記号は、それぞれ上記の式で表される基に対応している。
※は、結合手を表す。
表8~表27中の「Q1」欄及び「Q2」欄に記載されている記号は、それぞれ上記の式で表される基に対応している。
表8~表27中の「RR」欄に記載されている記号は、RR基を表し、それぞれ下記
式(a1)~式(a69);
式(b1)~式(b4);
式(c1)~式(c4);
式(d1)~式(d5);
式(e1)~式(e20);
式(f1)~式(f5);
式(g1)~式(g9);
式(h1)~式(h9);
式(j1)~式(j9);
式(k1)~式(k4);
式(m1)~式(m9);
式(n1)~式(n3);
式(о1)~式(о5);
式(p1)~式(p23);
式(q1)~式(q26);
式(r1)~式(r26);
式(s1)~式(s26);
式(t1);
で表される基に対応しており、
表8~表27中の「No」欄に記載されている数値は、それぞれRR基が置換している位置を表し、
「1」は、RR基がRIb1に置換していることを表し、
「2」は、RR基がRIb2に置換していることを表し、
「3」は、RR基がRIb3に置換していることを表し、
「4」は、RR基がRIb4に置換していることを表し、
「5」は、RR基がRIb5に置換していることを表す。
※は、結合手を表す。
なお、表f1~表f6中の「Q1」欄及び「Q2」欄に記載されている記号は、それぞれ上記の式で表される基に対応している。
※は、結合手を表す。
-SO3 -及び-CO2 -から選ばれる1つ以上が置換された陰イオンと、
Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及びK+から選ばれる1つ以上の陽イオンからなる金属塩が挙げられる。
Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及びK+から選ばれる1つ以上の陽イオンからなる金属塩が挙げられる。
表29~表30中の「Met」欄に記載されている記号としてMg2+は、Mg2+を表し、
Ca2+は、Ca2+を表し、
Sr2+は、Sr2+を表し、
Ba2+は、Ba2+を表し、
Ni2+は、Ni2+を表し、
Zn2+は、Zn2+を表し、
Fe2+は、Fe2+を表し、
Co2+は、Co2+を表し、
Sn2+は、Sn2+を表し、
Mn2+は、Mn2+を表し、
Al3+は、Al3+を表し、
Fe3+は、Fe3+を表し、
Cr3+は、Cr3+を表し、
Sn4+は、Sn4+を表し、
Mn4+は、Mn4+を表し、
Cu2+は、Cu2+を表し、
Li+は、Li+を表し、
Na+は、Na+を表し、
K+は、K+を表す。
式(Ie)中のmは、1以上の整数であり、好ましくは1~20の整数であり、より好ましくは1~10の整数である。
式(Ie)中のnは、1以上の整数であり、好ましくは1~20の整数であり、より好ましくは1~10の整数である。
ただし、本発明の化合物(I)が、前記のオリゴマー又はポリマーである場合は、m及びnは、化合物(I)の電荷がゼロになるような配位子の個数及び金属原子の個数の比率を表す最小の整数を表すことにより、化合物(I)が前記のオリゴマー又はポリマーであることを表す。
式(Ia1)~式(Ia903)で表される化合物;
式(Ia972)で表される化合物;
式(If1)~式(If1355)で表される化合物;
式(Ia1)~式(Ia903)、式(Ia972)及び式(If1)~式(If1355)で表される化合物に、
-SO3H、-CO2H、-SO3NH4、-CO2NH4、-SO2NH2、-CONH2、フタルイミドメチル基(C6H4(CO)2N-CH2-)、-SO2NH(CH2)2N(CH2CH3)2、-N(CH3)((CH2)11CH3)、フッ素原子、塩素原子及び臭素原子から選ばれる1つ以上が置換された化合物;及び
式(Ia1)~式(Ia903)、式(Ia972)及び式(If1)~式(If1355)で表される化合物に、-SO3 -及び-CO2 -から選ばれる1つ以上が置換された陰イオンと、
Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及びK+から選ばれる1つ以上の陽イオンからなる金属塩
が好ましく、
式(Ia972)で表される化合物;
式(If1)~式(If1355)で表される化合物;
式(Ia1)~式(Ia903)、式(Ia972)及び式(If1)~式(If1355)で表される化合物に、
-SO3H、-CO2H、-SO3NH4、-CO2NH4、フッ素原子、塩素原子及び臭素原子から選ばれる1つ以上が置換された化合物;及び
式(Id1)~式(Id152)及び式(Ih1)~式(Ih170)で表される陰イオンと、
Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及びK+から選ばれる1つ以上の陽イオンからなる金属塩
がより好ましく、
式(Ia1)~式(Ia903)で表される化合物がとりわけ好ましく、
式(Ia1)~式(Ia119)で表される化合物が一層好ましく、
式(Ia1)~式(Ia5)、式(Ia26)及び式(Ia87)~式(Ia89)で表される化合物が特に好ましく、
式(Ia2)~式(Ia3)で表される化合物が極めて好ましく、
式(Ia3)で表される化合物が最も好ましい。
例えば、反応終了後、反応混合物中の化合物(I)は溶解しにくいが、化合物(I)以外の化合物が溶解しやすい、メタノール等の溶媒に、反応混合物を加えて、よく混合した後、ろ過することによって、化合物(I)を取り出すことができる。さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒又はそれらの混合溶媒で、水酸化ナトリウム水溶液等のアルカリ性水溶液で、及び/又は塩酸等の酸性水溶液で、得られた残渣を洗浄した後、水、メタノール等の低沸点アルコール又はそれらの混合溶媒で洗浄し、化合物(I)を取り出してもよい。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物の溶媒を留去し、得られた残渣をカラムクロマトグラフィー及び/又は再結晶等で精製してもよいし、
反応終了後、反応混合物をカラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
反応終了後、反応混合物中の化合物(I)は溶解しにくいが、化合物(I)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I)を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
式(pt1)で表される化合物と、式(pt2)で表される化合物との反応により、式(I’’)で表される化合物(以下、化合物(I’’)という場合がある。)を製造し、続いて、
式(I’’)で表される化合物を、塩基存在下、加水分解して、式(IM1)で表される化合物(以下、化合物(IM1)という場合がある。)を製造し、さらに、
式(IM1)で表される化合物と、式(pt3)で表される化合物との反応により、製造することができる。
例えば、反応終了後、反応混合物中の化合物(I’’)は溶解しにくいが、化合物(I’’)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I’’)を取り出すことができる。さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒又はそれらの混合溶媒で、水酸化ナトリウム水溶液等のアルカリ性水溶液で、及び/又は塩酸等の酸性水溶液で、得られた残渣を洗浄した後、水、メタノール等の低沸点アルコール又はそれらの混合溶媒で洗浄し、化合物(I’’)を取り出してもよい。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物の溶媒を留去し、得られた残渣をカラムクロマトグラフィー及び/又は再結晶等で精製してもよいし、
反応終了後、反応混合物をカラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
反応終了後、反応混合物中の化合物(I’’)は溶解しにくいが、化合物(I’’)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I’’)を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
例えば、反応終了後、反応混合物中の化合物(I)は溶解しにくいが、化合物(I)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I)を取り出すことができる。さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒又はそれらの混合溶媒で、水酸化ナトリウム水溶液等のアルカリ性水溶液で、及び/又は塩酸等の酸性水溶液で、得られた残渣を洗浄した後、水、メタノール等の低沸点アルコール又はそれらの混合溶媒で洗浄し、化合物(I)を取り出してもよい。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物の溶媒を留去し、得られた残渣をカラムクロマトグラフィー及び/又は再結晶等で精製してもよいし、
反応終了後、反応混合物をカラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
反応終了後、反応混合物中の化合物(I)は溶解しにくいが、化合物(I)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I)を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
無機塩基が好ましく、
水酸化リチウム、水酸化ナトリウム、及び水酸化カリウムがより好ましく、
水酸化ナトリウム及び水酸化カリウムがさらに好ましく、
水酸化カリウムがとりわけ好ましい。
例えば、反応終了後、反応混合物に塩酸等の酸性水溶液を加えて中和した後、ろ過することによって、化合物(IM1)を取り出すことができる。さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒、アセトン等のケトン溶媒、メタノール等のアルコール溶媒、アセトニトリル等のニトリル溶媒、水又はそれらの混合溶媒で、水酸化ナトリウム水溶液等のアルカリ性水溶液で、及び/又は塩酸等の酸性水溶液で、得られた残渣を洗浄し、化合物(IM1)を取り出してもよい。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物の溶媒を留去し、得られた残渣をカラムクロマトグラフィー及び/又は再結晶等で精製してもよいし、
反応終了後、反応混合物をカラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
反応終了後、反応混合物に塩酸等の酸性水溶液を加えて中和した後、ろ過することによって、化合物(IM1)を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
式(pt1)で表される化合物と、式(pt3)で表される化合物との反応により、式(IM2)で表される化合物(以下、化合物(IM2)という場合がある。)を製造し、続いて、
式(IM2)で表される化合物と、式(pt2)で表される化合物との反応により、製造することができる。
例えば、反応終了後、反応混合物中の化合物(IM2)は溶解しにくいが、化合物(IM2)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(IM2)を取り出すことができる。
さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒、アセトン等のケトン溶媒、メタノール等のアルコール溶媒、アセトニトリル等のニトリル溶媒、水又はそれらの混合溶媒で、水酸化ナトリウム水溶液等のアルカリ性水溶液で、及び/又は塩酸等の酸性水溶液で、得られた残渣を洗浄し、化合物(IM2)を取り出すことができる。
さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物の溶媒を留去し、得られた残渣をカラムクロマトグラフィー及び/又は再結晶等で精製してもよいし、
反応終了後、反応混合物をカラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
反応終了後、反応混合物中の化合物(IM2)は溶解しにくいが、化合物(IM2)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(IM2)を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
例えば、反応終了後、反応混合物中の化合物(I)は溶解しにくいが、化合物(I)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I)を取り出すことができる。さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒又はそれらの混合溶媒で、水酸化ナトリウム水溶液等のアルカリ性水溶液で、及び/又は塩酸等の酸性水溶液で、得られた残渣を洗浄した後、水、メタノール等の低沸点アルコール又はそれらの混合溶媒で洗浄し、化合物(I)を取り出してもよい。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物の溶媒を留去し、得られた残渣をカラムクロマトグラフィー及び/又は再結晶等で精製してもよいし、
反応終了後、反応混合物をカラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
反応終了後、反応混合物中の化合物(I)は溶解しにくいが、化合物(I)以外の化合物が溶解しやすい、メタノール等の溶媒と、反応混合物とを、よく混合した後、ろ過することによって、化合物(I)を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
化合物(I)にスルホ基又は-SO3Mを導入した化合物は、本発明の化合物に含まれる。
該溶媒としては、塩化メチレン、クロロホルム、1,2-ジクロロベンゼン、トリクロロベンゼン(例えば、1,3,5-トリクロロベンゼン)、1-クロロナフタレン、2-クロロナフタレン等のハロゲン化炭化水素溶媒が挙げられる。
例えば、反応終了後、反応混合物を氷に滴下し、得られた混合物をろ過することによって、化合物(I)にスルホ基又は-SO3Mを導入した化合物を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物を氷に滴下し、得られた混合物を、化合物(I)にスルホ基又は-SO3Mを導入した化合物は溶解しにくいが、化合物(I)にスルホ基又は-SO3Mを導入した化合物以外の化合物が溶解しやすい、メタノール等のアルコール溶媒、アセトニトリル等のニトリル溶媒及びそれらの混合溶媒等の親水性有機溶媒と混合し、ろ過することによって、化合物(I)にスルホ基又は-SO3Mを導入した化合物を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
または、反応終了後、反応混合物を氷に滴下し、得られた混合物を、アンモニア、水溶性アミン又はそれらの混合物等の水溶液で中和した後、この混合物を、メタノール等のアルコール溶媒、アセトニトリル等のニトリル溶媒及びそれらの混合溶媒等の親水性有機溶媒と混合し、ろ過し、得られたろ液の溶媒を留去することによって、化合物(I)にスルホ基又は-SO3Mを導入した化合物を取り出すことができる。さらに、カラムクロマトグラフィー及び/又は再結晶等で精製してもよい。
該溶媒としては、水;アセトニトリル等のニトリル溶媒;メタノール、エタノール、1-プロパノール、2-プロパノール、1-ブタノール、1-ペンタノール、1-ヘキサノール、1-ヘプタノール、2-エチル-1-ヘキサノール、1-オクタノール、フェノール等のアルコール溶媒;アミン溶媒;ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル溶媒;アセトン、メチルイソブチルケトン等のケトン溶媒;酢酸エチル、安息香酸メチル等のエステル溶媒;ヘキサン等の脂肪族炭化水素溶媒;トルエン、トリメチルベンゼン(例えば、1,3,5-トリメチルベンゼン)、デカリン、テトラリン等の芳香族炭化水素溶媒;塩化メチレン、クロロホルム、1,2-ジクロロベンゼン、トリクロロベンゼン(例えば、1,3,5-トリクロロベンゼン)、1-クロロナフタレン、2-クロロナフタレン等のハロゲン化炭化水素溶媒;ニトロベンゼン等のニトロ化炭化水素溶媒;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒;ジメチルスルホキシド等のスルホキシド溶媒;等が挙げられ、
水;アセトニトリル等のニトリル溶媒;メタノール、エタノール、1-プロパノール、2-プロパノール等のアルコール溶媒;テトラヒドロフラン等のエーテル溶媒;アセトン等のケトン溶媒;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒;ジメチルスルホキシド等のスルホキシド溶媒;及びそれらの混合溶媒が好ましく、
水がより好ましい。
無機塩基が好ましく、
水酸化リチウム、水酸化ナトリウム、及び水酸化カリウムがより好ましく、
水酸化ナトリウム及び水酸化カリウムがさらに好ましく、
水酸化ナトリウムがとりわけ好ましい。
例えば、反応終了後、反応混合物をろ過することによって、-SO3(MM)及び/又は-CO2(MM)を有する化合物(I)を取り出すことができる。さらに、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒、ジメチルスルホキシド等のスルホキシド溶媒、アセトン等のケトン溶媒、メタノール等のアルコール溶媒、アセトニトリル等のニトリル溶媒、水又はそれらの混合溶媒で、得られた残渣を洗浄して精製してもよい。
本発明の着色組成物は、化合物(I)及び溶剤(E)を含む。本発明の着色組成物によれば、C.I.ピグメントイエロー138を含む着色組成物に比べて、より濃色なカラーフィルタを形成することができる。本発明の着色組成物から形成されるカラーフィルタは、液晶表示装置等の表示装置に好適に用いられる。本発明の着色組成物は、好ましくは黄色組成物、橙色組成物、赤色組成物及び緑色組成物である。
本明細書において「固形分の総量」とは、本発明の着色組成物から溶剤(E)を除いた成分の合計量をいう。固形分の総量及びこれに対する各成分の含有量は、液体クロマトグラフィー又はガスクロマトグラフィー等の公知の分析手段で測定することができる。
溶剤(E)は特に限定されず、当該分野で通常使用される溶剤を用いることができる。
溶剤(E)は、例えば、エステル溶剤(分子内に-CO-O-を含み、-O-を含まない溶剤)、エーテル溶剤(分子内に-O-を含み、-CO-O-を含まない溶剤)、エーテルエステル溶剤(分子内に-CO-O-と-O-とを含む溶剤)、ケトン溶剤(分子内に-CO-を含み、-CO-O-を含まない溶剤)、アルコール溶剤(分子内にOHを含み、-O-、-CO-及び-CO-O-を含まない溶剤)、芳香族炭化水素溶剤、アミド溶剤及びジメチルスルホキシド等が挙げられる。
樹脂(B)は、アルカリ可溶性樹脂であることが好ましく、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群より選ばれる少なくとも1種の単量体(以下、「単量体(a)」という場合がある。)に由来する構造単位を有する重合体であることがより好ましい。
樹脂(B)は、炭素数2~4の環状エーテル構造とエチレン性不飽和結合とを有する単量体(以下、「単量体(b)」という場合がある。)に由来する構造単位、及びその他の構造単位を有する共重合体であることが好ましい。
その他の構造単位としては、単量体(a)と共重合可能な単量体(ただし、単量体(a)及び単量体(b)とは異なる。以下、「単量体(c)」という場合がある。)に由来する構造単位、エチレン性不飽和結合を有する構造単位等が挙げられる。
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3-ビニルフタル酸、4-ビニルフタル酸、3,4,5,6-テトラヒドロフタル酸、1,2,3,6-テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸及び1,4-シクロヘキセンジカルボン酸等の不飽和ジカルボン酸;
メチル-5-ノルボルネン-2,3-ジカルボン酸、5-カルボキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-エチルビシクロ[2.2.1]ヘプト-2-エン等のカルボキシ基を含有するビシクロ不飽和化合物;
無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3-ビニルフタル酸無水物、4-ビニルフタル酸無水物、3,4,5,6-テトラヒドロフタル酸無水物、1,2,3,6-テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン無水物等の不飽和ジカルボン酸無水物;
こはく酸モノ〔2-(メタ)アクリロイルオキシエチル〕及びフタル酸モノ〔2-(メタ)アクリロイルオキシエチル〕等の2価以上の多価カルボン酸の不飽和モノ〔(メタ)アクリロイルオキシアルキル〕エステル;
α-(ヒドロキシメチル)アクリル酸等、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和アクリレート;
等が挙げられる。
単量体(b)は、炭素数2~4の環状エーテル構造と(メタ)アクリロイルオキシ基とを有する単量体であることが好ましい。
単量体(b1-1)としては、例えば、
グリシジル(メタ)アクリレート、β-メチルグリシジル(メタ)アクリレート、β-エチルグリシジル(メタ)アクリレート、グリシジルビニルエーテル、o-ビニルベンジルグリシジルエーテル、m-ビニルベンジルグリシジルエーテル、p-ビニルベンジルグリシジルエーテル、α-メチル-o-ビニルベンジルグリシジルエーテル、α-メチル-m-ビニルベンジルグリシジルエーテル、α-メチル-p-ビニルベンジルグリシジルエーテル、2,3-ビス(グリシジルオキシメチル)スチレン、2,4-ビス(グリシジルオキシメチル)スチレン、2,5-ビス(グリシジルオキシメチル)スチレン、2,6-ビス(グリシジルオキシメチル)スチレン、2,3,4-トリス(グリシジルオキシメチル)スチレン、2,3,5-トリス(グリシジルオキシメチル)スチレン、2,3,6-トリス(グリシジルオキシメチル)スチレン、3,4,5-トリス(グリシジルオキシメチル)スチレン及び2,4,6-トリス(グリシジルオキシメチル)スチレン等が挙げられる。
Xa及びXbは、互いに独立に、単結合、*-Rc-、*-Rc-O-、*-Rc-S-又は*-Rc-NH-を表す。
Rcは、炭素数1~6のアルカンジイル基を表す。
*は、Oとの結合手を表す。]
単量体(b2)としては、例えば、3-メチル-3-メタクリルロイルオキシメチルオキセタン、3-メチル-3-アクリロイルオキシメチルオキセタン、3-エチル-3-メタクリロイルオキシメチルオキセタン、3-エチル-3-アクリロイルオキシメチルオキセタン、3-メチル-3-メタクリロイルオキシエチルオキセタン、3-メチル-3-アクリロイルオキシエチルオキセタン、3-エチル-3-メタクリロイルオキシエチルオキセタン、3-エチル-3-アクリロイルオキシエチルオキセタン等が挙げられる。
単量体(b3)としては、例えば、テトラヒドロフルフリルアクリレート(例えば、ビスコートV#150、大阪有機化学工業(株)製)、テトラヒドロフルフリルメタクリレート等が挙げられる。
2-ヒドロキシエチル(メタ)アクリレート及び2-ヒドロキシプロピル(メタ)アクリレート等のヒドロキシ基含有(メタ)アクリル酸エステル;
2,2,3,3,4,4,5,5-オクタフルオロペンチル(メタ)アクリレート等のハロゲン原子含有(メタ)アクリル酸エステル;
マレイン酸ジエチル、フマル酸ジエチル及びイタコン酸ジエチル等のジカルボン酸ジエステル;
ビシクロ[2.2.1]ヘプト-2-エン、5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチルビシクロ[2.2.1]ヘプト-2-エン、5-(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5-メトキシビシクロ[2.2.1]ヘプト-2-エン、5-エトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(ヒドロキシメチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジメトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジエトキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチル-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-tert-ブトキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-シクロヘキシルオキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-フェノキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5,6-ビス(tert-ブトキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン及び5,6-ビス(シクロヘキシルオキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン等のビシクロ不飽和化合物;
N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、N-スクシンイミジル-3-マレイミドベンゾエート、N-スクシンイミジル-4-マレイミドブチレート、N-スクシンイミジル-6-マレイミドカプロエート、N-スクシンイミジル-3-マレイミドプロピオネート及びN-(9-アクリジニル)マレイミド等のジカルボニルイミド誘導体;
スチレン、o-メチルスチレン、m-メチルスチレン、p-メチルスチレン、ビニルトルエン、9-ビニルカルバゾール及びp-メトキシスチレン等のビニル基含有芳香族化合物;(メタ)アクリロニトリル等のビニル基含有ニトリル;塩化ビニル及び塩化ビニリデン等のハロゲン化炭化水素;(メタ)アクリルアミド等のビニル基含有アミド;酢酸ビニル等のエステル;1,3-ブタジエン、イソプレン及び2,3-ジメチル-1,3-ブタジエン等のジエン;等が挙げられる。
中でも、樹脂(B)としては、単量体(a)に由来する構造単位及び単量体(b)に由来する構造単位を含む共重合体が好ましい。
樹脂(B)は2種以上を組み合わせてもよく、この場合は、樹脂(B)は、少なくとも、
単量体(a)に由来する構造単位及び単量体(b)に由来する構造単位を含む共重合体を少なくとも1種含むことが好ましく、
単量体(a)に由来する構造単位及び単量体(b1)に由来する構造単位を含む共重合体を少なくとも1種含むことがより好ましく、
単量体(a)に由来する構造単位及び単量体(b1-2)に由来する構造単位を含む共重合体を少なくとも1種含むことがさらに好ましく、
3,4-エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート/(メタ)アクリル酸共重合体、3,4-エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート/ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体、3,4-エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート/(メタ)アクリル酸/N-シクロヘキシルマレイミド/2-ヒドロキシエチル(メタ)アクリレート共重合体、3,4-エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート/(メタ)アクリル酸/ビニルトルエン共重合体、3,4-エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート/(メタ)アクリル酸/2-エチルヘキシル(メタ)アクリレート共重合体から選ばれる1以上を含むことがとりわけ好ましい。
本発明の着色組成物は、予め化合物(I)と溶剤(E)とを含む化合物(I)含有液を調製した後、該化合物(I)含有液を使用して着色組成物を調製してもよい。化合物(I)が溶剤(E)に溶解しない場合、化合物(I)含有液は、化合物(I)を溶剤(E)に分散させて混合することにより調製してもよい。化合物(I)含有液は、着色組成物に含有される溶剤(E)の一部又は全部を含んでいてもよい。
なお、該化合物(I)含有液は、本発明の着色組成物に含まれる。
また、化合物(I)は、必要に応じて、
ソルトミリング法等による微粒化、結晶構造変換、粒子の整形及び/又は粒径の略均一化処理;
化合物(I)と、水及び/又は有機溶媒とを混合し、撹拌及び/又は加熱しながら撹拌して、懸濁液を得た後、該懸濁液をろ過して、結晶構造が変わった化合物(I)を得る処理、微粒化処理、粒子の整形処理及び/又は粒径の略均一化処理;
再結晶することにより、化合物(I)の結晶構造を変える処理、微粒化処理、粒子の整形処理及び/又は粒径の略均一化処理;
化合物(I)と、水、硫酸又は有機溶媒とを混合し、撹拌及び/又は加熱しながら撹拌して、溶液又は懸濁液を得た後、該溶液又は該懸濁液を、化合物(I)の貧溶媒と混合し、懸濁液を得た後、該懸濁液をろ過して、結晶構造が変わった化合物(I)を得る処理、微粒化処理、粒子の整形処理及び/又は粒径の略均一化処理;
化合物(I)と、誘導体と、水及び/又は有機溶媒とを混合し、撹拌及び/又は加熱しながら撹拌して、懸濁液を得た後、該懸濁液をろ過して、結晶構造が変わった化合物(I)を含む混合物を得る処理、化合物(I)と誘導体とを混合する処理、微粒化処理、粒子の整形処理及び/又は粒径の略均一化処理;
化合物(I)と誘導体の混合物を再結晶することにより、結晶構造が変わった化合物(I)を含む混合物を得る処理、化合物(I)と誘導体とを混合する処理、微粒化処理、粒子の整形処理及び/又は粒径の略均一化処理;
化合物(I)と、誘導体と、水、硫酸又は有機溶媒とを混合し、撹拌及び/又は加熱しながら撹拌して、溶液又は懸濁液を得た後、該溶液又は該懸濁液を、化合物(I)の貧溶媒と混合し、懸濁液を得た後、該懸濁液をろ過して、結晶構造が変わった化合物(I)を含む混合物を得る処理、化合物(I)と誘導体とを混合する処理、微粒化処理、粒子の整形処理及び/又は粒径の略均一化処理;
等が施されていてもよい。
化合物(I)又は誘導体を複数種使用する場合、それぞれ単独でこれらの処理をしてもよいし、複数種を混合してこれらの処理をしてもよい。
化合物(I)の粒径は、略均一であることが好ましい。
アセトニトリル等のニトリル溶媒;メタノール、エタノール、1-プロパノール、2-プロパノール、1-ブタノール、1-ペンタノール、1-ヘキサノール、1-ヘプタノール、2-エチル-1-ヘキサノール、1-オクタノール、フェノール等のアルコール溶媒;アミン溶媒;ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル溶媒;アセトン、メチルイソブチルケトン等のケトン溶媒;酢酸エチル、安息香酸メチル等のエステル溶媒;ヘキサン等の脂肪族炭化水素溶媒;トルエン、トリメチルベンゼン(例えば、1,3,5-トリメチルベンゼン)、デカリン、テトラリン等の芳香族炭化水素溶媒;塩化メチレン、クロロホルム、1,2-ジクロロベンゼン、トリクロロベンゼン(例えば、1,3,5-トリクロロベンゼン)、1-クロロナフタレン、2-クロロナフタレン等のハロゲン化炭化水素溶媒;ニトロベンゼン等のニトロ化炭化水素溶媒;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド溶媒;ジメチルスルホキシド等のスルホキシド溶媒;等が挙げられる。
アセトニトリル等のニトリル溶媒;メタノール、エタノール、1-プロパノール、2-プロパノール、1-ブタノール、1-ペンタノール、1-ヘキサノール、1-ヘプタノール、2-エチル-1-ヘキサノール、1-オクタノール、フェノール等のアルコール溶媒;アミン溶媒;ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル溶媒;アセトン、メチルイソブチルケトン等のケトン溶媒;酢酸エチル、安息香酸メチル等のエステル溶媒;ヘキサン等の脂肪族炭化水素溶媒;トルエン、トリメチルベンゼン(例えば、1,3,5-トリメチルベンゼン)、デカリン、テトラリン等の芳香族炭化水素溶媒;塩化メチレン、クロロホルム、1,2-ジクロロベンゼン、トリクロロベンゼン(例えば、1,3,5-トリクロロベンゼン)、1-クロロナフタレン、2-クロロナフタレン等のハロゲン化炭化水素溶媒;ニトロベンゼン等のニトロ化炭化水素溶媒;等が挙げられる。
該分散剤の使用量が前記の範囲にあると、より均一な分散状態の化合物(I)含有液が得られる傾向がある。
重合性化合物(C)は、重合開始剤(D)から発生した活性ラジカル及び/又は酸によって重合しうる化合物であり、例えば、重合性のエチレン性不飽和結合を有する化合物等であり、好ましくは(メタ)アクリル酸エステル化合物である。
重合開始剤(D)は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始しうる化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。
重合開始剤(D)としては、オキシム化合物、例えばO-アシルオキシム化合物等、アルキルフェノン化合物、ビイミダゾール化合物、トリアジン化合物及びアシルホスフィンオキサイド化合物等が挙げられる。
アルキルフェノン化合物としては、2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン、2-ヒドロキシ-2-メチル-1-〔4-(2-ヒドロキシエトキシ)フェニル〕プロパン-1-オン、1-ヒドロキシシクロヘキシルフェニルケトン、2-ヒドロキシ-2-メチル-1-(4-イソプロペニルフェニル)プロパン-1-オンのオリゴマー、α,α-ジエトキシアセトフェノン及びベンジルジメチルケタールも挙げられる。
これらは、後述の重合開始助剤(以下、重合開始助剤(D1)という場合がある。)、特にアミン類と組み合わせて用いることが好ましい。
本発明の着色組成物は、重合開始助剤(D1)を含有してもよい。重合開始助剤(D1)は、重合開始剤(D)によって重合が開始された重合性化合物(C)の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤(D1)を含む場合、通常、重合開始剤(D)と組み合わせて用いられる。
重合開始助剤(D1)としては、アミン化合物、アルコキシアントラセン化合物、チオキサントン化合物及びカルボン酸化合物等が挙げられる。
本発明の着色組成物は、化合物(I)以外の着色剤(以下、着色剤(A1)という場合がある。)を含んでいてもよい。着色剤(A1)には、1種又は2種以上の着色剤が含まれていてもよい。着色剤(A1)は、黄色着色剤、橙色着色剤、赤色着色剤及び緑色着色剤から選ばれる1種以上を含むことが好ましく、黄色着色剤及び緑色着色剤から選ばれる1種以上を含むことがより好ましい。
C.I.ソルベントイエロー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.ソルベントレッド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.ソルベントオレンジ2、7、11、15、26、41、54、56、77、86、99;
C.I.ソルベントバイオレット11、13、14、26、31、36、37、38、45、47、48、51、59、60;
C.I.ソルベントブルー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.ソルベントグリーン1、3、4、5、7、28、29、32、33、34、35等のC.I.ソルベント染料、
C.I.アシッドイエロー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.アシッドレッド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.アシッドオレンジ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.アシッドバイオレット6B、7、9、15、16、17、19、21、23、24、25、30、34、38、49、72、102;
C.I.アシッドブルー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.アシッドグリーン1、3、5、6、7、8、9、11、13、14、15、16、22、25、27、28、41、50、50:1、58、63、65、80、104、105、106、109等のC.I.アシッド染料、
C.I.ダイレクトイエロー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.ダイレクトレッド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.ダイレクトオレンジ26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107;
C.I.ダイレクトバイオレット47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104;
C.I.ダイレクトブルー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.ダイレクトグリーン25、27、31、32、34、37、63、65、66、67、68、69、72、79、82等のC.I.ダイレクト染料、
C.I.ディスパースイエロー51、54、76;
C.I.ディスパースバイオレット26、27;
C.I.ディスパースブルー1、14、56、60等のC.I.ディスパース染料、
C.I.ベーシックレッド1、10;
C.I.ベーシックブルー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.ベーシックバイオレット2;
C.I.ベーシックレッド9;
C.I.ベーシックグリーン1;等のC.I.ベーシック染料、
C.I.リアクティブイエロー2、76、116;
C.I.リアクティブオレンジ16;
C.I.リアクティブレッド36;等のC.I.リアクティブ染料、
C.I.モーダントイエロー5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;
C.I.モーダントレッド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.モーダントオレンジ3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48;
C.I.モーダントバイオレット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.モーダントブルー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.モーダントグリーン1、3、4、5、10、13、15、19、21、23、26、29、31、33、34、35、41、43、53等のC.I.モーダント染料、
C.I.バットグリーン1等のC.I.バット染料等
具体的には、C.I.ピグメントイエロー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等の黄色顔料;
C.I.ピグメントオレンジ13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等のオレンジ色顔料;
C.I.ピグメントレッド9、97、105、122、123、144、149、166、168、176、177、178、179、180、190、192、209、215、216、224、242、254、255、264、265、266、268、269、273等の赤色顔料;
C.I.ピグメントブルー15、15:1、15:2、15:3、15:4、15:6、16、60等の青色顔料;
C.I.ピグメントバイオレット1、19、23、29、32、36、38等のバイオレット色顔料;
C.I.ピグメントグリーン7、36、58、59、62、63等の緑色顔料;
C.I.ピグメントブラウン23、25等のブラウン色顔料;
C.I.ピグメントブラック1、7、31、32等の黒色顔料
が挙げられる。
黄色着色剤としては、黄色染料及び黄色顔料が好ましく、黄色顔料がより好ましく、キノフタロン顔料、金属含有顔料、イソインドリン顔料がさらに好ましく、C.I.ピグメントイエロー129、138、139、150、185、231がとりわけ好ましく、C.I.ピグメントイエロー138、139、150、185、231が一層好ましい。
橙色着色剤としては、橙色染料及び橙色顔料が好ましく、橙色顔料がより好ましく、C.I.ピグメントオレンジ13、31、36、38、40、42、43、51、55、59、61、64、65、71、73がさらに好ましい。
赤色着色剤としては、赤色染料及び赤色顔料が好ましく、アゾ染料、アントラキノン染料、トリフェニルメタン染料、キサンテン染料、ペリレン染料、アゾ顔料、ジケトピロロピロール顔料、アントラキノン顔料、トリフェニルメタン染料、キサンテン顔料及びペリレン顔料がより好ましく、C.I.アシッドレッド52、C.I.ピグメントレッド144、177、179、242、254及び269がさらに好ましい。
緑色着色剤としては、緑色染料及び緑色顔料が好ましく、緑色顔料がより好ましく、フタロシアニン顔料がさらに好ましく、ハロゲン化銅フタロシアニン顔料、ハロゲン化亜鉛フタロシアニン顔料及びハロゲン化アルミニウム亜鉛フタロシアニン顔料がとりわけ好ましく、C.I.ピグメントグリーン7、36、58、59、62及び63が一層好ましい。
本発明の着色組成物が着色剤(A1)を含む場合、予め着色剤(A1)と溶剤(E)とを含む着色剤(A1)含有液を調製した後、該着色剤(A1)含有液を使用して着色組成物を調製してもよい。着色剤(A1)が溶剤(E)に溶解しない場合、着色剤(A1)含有液は、着色剤(A1)を溶剤(E)に分散させて混合することにより調製できる。着色剤(A1)含有液は、着色組成物に含有される溶剤(E)の一部又は全部を含んでいてもよい。
該分散剤の使用量が前記の範囲にあると、より均一な分散状態の着色剤(A1)含有液が得られる傾向がある。
レベリング剤(F)としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。
レベリング剤(F)の含有量が前記の範囲内にあると、カラーフィルタの平坦性を良好にすることができる。
着色剤の耐熱性及び耐光性を向上させる観点から、酸化防止剤を単独又は2種以上を組み合わせて用いることが好ましい。酸化防止剤としては、工業的に一般に使用される酸化防止剤であれば特に限定はなく、フェノール系酸化防止剤、リン系酸化防止剤及び硫黄系酸化防止剤などを用いることができる。
本発明の着色組成物は、必要に応じて、充填剤、他の高分子化合物、密着促進剤、光安定剤、連鎖移動剤等、当該技術分野で公知の添加剤を含んでもよい。
密着促進剤としては、例えば、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリス(2-メトキシエトキシ)シラン、3-グリシジルオキシプロピルトリメトキシシラン、3-グリシドキシプロピルメチルジメトキシシラン、3-グリシドキシプロピルメチルジエトキシシラン、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、3-クロロプロピルメチルジメトキシシラン、3-クロロプロピルトリメトキシシラン、3-メタクリロイルオキシプロピルトリメトキシシラン、3-メルカプトプロピルトリメトキシシラン、3-スルファニルプロピルトリメトキシシラン、3-イソシアネートプロピルトリエトキシシラン、N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン、N-2-(アミノエチル)-3-アミノプロピルメチルジエトキシシラン、N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン、N-2-(アミノエチル)-3-アミノプロピルメチルジエトキシシラン、3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、N-フェニル-3-アミノプロピルトリメトキシシラン及びN-フェニル-3-アミノプロピルトリエトキシシラン等が挙げられる。
本発明の着色組成物は、例えば、化合物(I)、溶剤(E)、及び、必要に応じて、樹脂(B)、重合性化合物(C)、重合開始剤(D)、重合開始助剤(D1)、着色剤(A1)、レベリング剤(F)、酸化防止剤(G)及び/又はその他の成分を混合することにより調製できる。混合は公知又は慣用の装置や条件により行うことができる。
化合物(I)は、予め溶剤(E)の一部または全部と混合し、化合物(I)の平均粒子径が0.2μm以下程度となるまで、ビーズミルなどを用いて分散させた化合物(I)含有液の状態で用いることが好ましい。この際、必要に応じて前記分散剤、樹脂(B)の一部または全部を配合してもよい。
着色剤(A1)は、予め溶剤(E)の一部または全部と混合し、着色剤(A1)の平均粒子径が0.2μm以下程度となるまで、ビーズミルなどを用いて分散させた着色剤(A1)含有液の状態で用いることが好ましい。この際、必要に応じて前記分散剤、樹脂(B)の一部または全部を配合してもよい。
化合物(I)は、予め溶剤(E)の一部または全部に溶解させた溶液(該溶液は、化合物(I)含有液に含まれる)の状態で用いることが好ましい。さらに、該化合物(I)含有液を、孔径0.01μm以上1μm以下程度のフィルタでろ過することが好ましい。
着色剤(A1)は、予め溶剤(E)の一部または全部に溶解させた溶液(該溶液は、着色剤(A1)含有液に含まれる)の状態で用いることが好ましい。さらに、該着色剤(A1)含有液を、孔径0.01μm以上1μm以下程度のフィルタでろ過することが好ましい。
混合後の着色組成物を、孔径0.01μm以上10μm以下程度のフィルタでろ過することが好ましい。
本発明の着色組成物から、カラーフィルタを形成することができる。
着色組成物を基板に塗布し、溶剤等の揮発成分を除去して乾燥させることにより、着色塗膜を形成することができる。このように形成した着色塗膜は、本発明のカラーフィルタに含まれる。
着色パターンを形成する方法としては、フォトリソグラフ法、インクジェット法、印刷法等が挙げられる。中でも、フォトリソグラフ法が好ましい。フォトリソグラフ法は、前記着色組成物を基板に塗布し、乾燥させて着色組成物層を形成し、フォトマスクを介して該着色組成物層を露光して、現像する方法である。フォトリソグラフ法において、露光の際にフォトマスクを用いないこと、及び/又は現像しないことにより、上記着色組成物層の硬化物である着色塗膜を形成することができる。このように形成した着色パターンや着色塗膜は、本発明のカラーフィルタである。
作製するカラーフィルタの膜厚は、特に限定されず、目的や用途等に応じて適宜調整することができ、例えば、0.1~30μmであり、好ましくは0.1~20μmであり、さらに好ましくは0.5~6μmである。
まず、着色組成物を基板上に塗布し、加熱乾燥(プリベーク)及び/又は減圧乾燥することにより溶剤等の揮発成分を除去して乾燥させ、平滑な着色組成物層を得る。
塗布方法としては、スピンコート法、スリットコート法及びスリット・アンド・スピンコート法等が挙げられる。
加熱乾燥を行う場合の温度は、30~120℃が好ましく、50~110℃がより好ましい。また加熱時間としては、10秒間~60分間であることが好ましく、30秒間~30分間であることがより好ましい。減圧乾燥を行う場合は、50~150Paの圧力下に、20~25℃の温度範囲で行うことが好ましい。着色組成物層の膜厚は、特に限定されず、目的とするカラーフィルタの膜厚に応じて適宜選択すればよい。
該フォトマスク上のパターンは特に限定されず、目的とする用途に応じたパターンが用いられる。露光に用いられる光源としては、250~450nmの波長の光を発生する光源が好ましい。例えば、350nm未満の光を、この波長域をカットするフィルタを用いてカットしたり、436nm付近、408nm付近、365nm付近の光を、これらの波長域を取り出すバンドパスフィルタを用いて選択的に取り出したりしてもよい。光源の具体例としては、水銀灯、発光ダイオード、メタルハライドランプおよびハロゲンランプが挙げられる。
露光面全体に均一に平行光線を照射することや、フォトマスクと着色組成物層が形成された基板との正確な位置合わせを行うことができるため、マスクアライナ及びステッパ等の露光装置を使用することが好ましい。
現像液としては、例えば、水酸化カリウム、炭酸水素ナトリウム、炭酸ナトリウム及び水酸化テトラメチルアンモニウム等のアルカリ性化合物の水溶液が好ましい。
アルカリ性化合物の濃度は、好ましくは0.01~10質量%であり、より好ましくは0.02~5質量%である。現像液は、界面活性剤を含んでいてもよい。
現像方法は、パドル法、ディッピング法及びスプレー法等のいずれでもよい。さらに現像時に基板を任意の角度に傾けてもよい。
現像後の基板は、水洗されることが好ましい。
さらに、得られた着色パターンに、ポストベークを行うことが好ましい。
ポストベーク温度は、150~250℃が好ましく、160~235℃がより好ましい。ポストベーク時間は、1~120分間が好ましく、10~60分間がより好ましい。この様にして得られた着色パターンや着色塗膜であるカラーフィルタは、種々の特性を付与する為、さらに表面コート処理に供してもよい。
装置:HLC-8120GPC(東ソー(株)製)
カラム:TSK-GELG2000HXL
カラム温度:40℃
溶媒:テトラヒドロフラン
流速:1.0mL/分
分析試料の固形分濃度:0.001~0.01質量%
注入量:50μL
検出器:RI
校正用標準物質:TSK STANDARD POLYSTYRENE F-40、F-4、F-288、A-2500、A-500(東ソー(株)製)
上記で得られたポリスチレン換算の重量平均分子量(Mw)及び数平均分子量(Mn)の比(Mw/Mn)を分散度とした。
安息香酸(東京化成工業(株)製)7.72部、8-アミノ-2-メチルキノリン(東京化成工業(株)製)2.00部、4-フェニルエチニルフタル酸無水物(東京化成工業(株)製)6.92部及び安息香酸メチル(東京化成工業(株)製)40.4部を混合した。
この混合物を、170℃に保ちながら、9時間撹拌した。
この混合物に、安息香酸(東京化成工業(株)製)7.83部を加えた。
この混合物を、170℃に保ちながら、7時間撹拌した。
この混合物に、4-フェニルエチニルフタル酸無水物(東京化成工業(株)製)3.19部及び安息香酸メチル(東京化成工業(株)製)8.97部を加えた。
この混合物を、170℃に保ちながら、17時間撹拌した。
この混合物に、安息香酸(東京化成工業(株)製)7.76部、4-フェニルエチニルフタル酸無水物(東京化成工業(株)製)3.17部及び安息香酸メチル(東京化成工業(株)製)6.17部を加えた。
この混合物を、170℃に保ちながら、19時間撹拌した。
この混合物を室温まで冷却し、この混合物に、メタノール420部を加え、1時間撹拌した。
この混合物をろ過し、得られた残渣を、メタノール120部で6回洗浄した。
得られた残渣を60℃で減圧乾燥させて、式(Ia3)で表される化合物7.23部を得た。
(質量分析)イオン化モード=ESI+: m/z=[M+H]+ 619
(質量分析)イオン化モード=ESI-: m/z=[M-H]- 617
Exact Mass: 618
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート280部を入れ、攪拌しながら80℃まで加熱した。次いで、アクリル酸38部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレート及び3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)289部、プロピレングリコールモノメチルエーテルアセテート125部の混合溶液を5時間かけて滴下した。一方、2,2-アゾビス(2,4-ジメチルバレロニトリル)33部をプロピレングリコールモノメチルエーテルアセテート235部に溶解した溶液を6時間かけて滴下した。滴下終了後、80℃で4時間保持した後、室温まで冷却して、固形分35.0%の共重合体(樹脂B1)の溶液を得た。得られた樹脂B1の重量平均分子量は8800、分散度は2.1、固形分換算の酸価は80mg-KOH/gであった。
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート340部を入れ、攪拌しながら80℃まで加熱した。次いで、アクリル酸57部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレート及び3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)54部、ベンジルメタクリレート239部、プロピレングリコールモノメチルエーテルアセテート73部の混合溶液を5時間かけて滴下した。一方、2,2-アゾビス(2,4-ジメチルバレロニトリル)40部をプロピレングリコールモノメチルエーテルアセテート197部に溶解した溶液を6時間かけて滴下した。滴下終了後、80℃で3時間保持した後、室温まで冷却して、固形分36.8%の共重合体(樹脂B2)の溶液を得た。得られた樹脂B2の重量平均分子量は9400、分散度は1.89、固形分換算の酸価は114mg-KOH/gであった。
以下の割合で各成分を混合し、ビーズミルを用いて着色剤を分散させて、着色組成物M1を得た。
着色剤(A):式(Ia3)で表される化合物 4.50部;
着色剤(A):式(z)で表される化合物 0.500部;
分散剤溶液:DISPERBYK-161(ビックケミー・ジャパン株式会社製)
16.7部;
樹脂(B):樹脂B1溶液 11.4部;
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
46.9部;
溶剤(E):乳酸エチル 20.0部;
着色組成物M1 57.6部;
樹脂(B):樹脂B2溶液 27.0部;
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
15.4部;
レベリング剤(F):トーレシリコーンSH8400(東レダウコーニング(株)製)
0.00630部;
得られたプリベーク着色塗膜の膜厚を、DektakXT(BRUKER製)を用いて測定した。
このプリベーク着色塗膜のスペクトルを、測色機:LVmicrоZ(株式会社ラムダビジョン製)を用いて測定した。
このプリベーク着色塗膜の膜厚、及びこのプリベーク着色塗膜の吸収スペクトルの最も長波長側の極大吸収波長を表31に示す。
このプリベーク着色塗膜を、230℃で30分間ポストベークを行うことにより、ポストベーク着色塗膜を得た。
以下の割合で各成分を混合し、ビーズミルを用いて着色剤を分散させて、着色組成物M2を得た。
着色剤(A):C.I.ピグメントイエロー138 12.0部;
分散剤の固形分 4.21部;
樹脂の固形分 5.05部;
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
74.8部;
溶剤(E):プロピレングリコールモノメチルエーテル
3.94部;
着色組成物M2 24.0部;
樹脂(B):樹脂B2溶液 35.0部;
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
41.0部;
レベリング剤(F):トーレシリコーンSH8400(東レダウコーニング(株)製)
0.00630部;
得られたプリベーク着色塗膜の膜厚を、DektakXT(BRUKER製)を用いて測定した。
このプリベーク着色塗膜のスペクトルを、測色機:LVmicrоZ(株式会社ラムダビジョン製)を用いて測定した。
このプリベーク着色塗膜の膜厚、及びこのプリベーク着色塗膜の吸収スペクトルの最も長波長側の極大吸収波長を表31に示す。
このプリベーク着色塗膜を、230℃で30分間ポストベークを行うことにより、ポストベーク着色塗膜を得た。
以下の割合で各成分を混合し、ビーズミルを用いて着色剤を分散させて、着色組成物M3を得た。
着色剤(A):C.I.ピグメントイエロー138 4.50部;
着色剤(A):式(z)で表される化合物 0.500部;
分散剤溶液:DISPERBYK-161(ビックケミー・ジャパン株式会社製)
16.7部;
樹脂(B):樹脂B1溶液 11.4部;
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
46.9部;
溶剤(E):乳酸エチル 20.0部;
着色組成物M3 57.6部;
樹脂(B):樹脂B2溶液 27.0部;
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
15.4部;
レベリング剤(F):トーレシリコーンSH8400(東レダウコーニング(株)製)
0.00630部;
得られたプリベーク着色塗膜の膜厚を、DektakXT(BRUKER製)を用いて測定した。
このプリベーク着色塗膜のスペクトルを、測色機:LVmicrоZ(株式会社ラムダビジョン製)を用いて測定した。
このプリベーク着色塗膜の膜厚、及びこのプリベーク着色塗膜の吸収スペクトルの最も長波長側の極大吸収波長を表31に示す。
このプリベーク着色塗膜を、230℃で30分間ポストベークを行うことにより、ポストベーク着色塗膜を得た。
「AAA」欄は、吸収スペクトルの最も長波長側の極大吸収波長を示し、
「BBB」欄は、吸収スペクトルの最も長波長側の肩ピークの波長を示す。
Claims (6)
- 下記式(I)で表される化合物と溶剤とを含む着色組成物。
[式(I)中、
R1~R5は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
R1及びR2、R2及びR3、R3及びR4、及びR4及びR5は、それぞれ互いに結合して環を形成していてもよい。
Mは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
MMは、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
Z1~Z4は、それぞれ独立して、水素原子、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
Q1及びQ2は、それぞれ独立して、2価の炭化水素基又は2価の複素環基を表し、
該2価の炭化水素基及び該2価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
ただし、Q1及びQ2の少なくとも一つは、式(y)で表される基を有する。
Y1は、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
※は結合手を表す。
Z1~Z4、式(y)で表される基、Y1、M及びMMがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてもよい。] - 樹脂を含む請求項1に記載の着色組成物。
- 重合性化合物と重合開始剤とを含む請求項1又は2に記載の着色組成物。
- 請求項1~3のいずれか一項に記載の着色組成物により形成されるカラーフィルタ。
- 請求項4に記載のカラーフィルタを含む表示装置。
- 式(I)で表される化合物。
[式(I)中、
R1~R5は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
R1及びR2、R2及びR3、R3及びR4、及びR4及びR5は、それぞれ互いに結合して環を形成していてもよい。
Mは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
MMは、アルカリ金属原子、配位子を有していてもよい金属原子又はN(Z1)(Z2)(Z3)(Z4)を表す。
Z1~Z4は、それぞれ独立して、水素原子、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
Q1及びQ2は、それぞれ独立して、2価の炭化水素基又は2価の複素環基を表し、
該2価の炭化水素基及び該2価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該2価の炭化水素基及び該2価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM又は式(y)で表される基に置き換わっていてもよい。
ただし、Q1及びQ2の少なくとも一つは、式(y)で表される基を有する。
Y1は、水素原子、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M、MM、炭素数1~40の1価の炭化水素基又は炭素数1~40の1価の複素環基を表し、
該1価の炭化水素基及び該1価の複素環基を構成する-C(-)(-)-は、-Si(-)(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH(-)-は、-N(-)-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH=は、-N=に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する-CH2-は、-O-、-S-、-S(O)2-又は-CO-に置き換わっていてもよく、
該1価の炭化水素基及び該1価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、-SO3M、-CO2M又はMMに置き換わっていてもよい。
※は結合手を表す。
Z1~Z4、式(y)で表される基、Y1、M及びMMがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてもよい。]
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