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WO2020060153A1 - Composé, composition de résine colorée, filtre coloré et dispositif d'affichage - Google Patents

Composé, composition de résine colorée, filtre coloré et dispositif d'affichage Download PDF

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Publication number
WO2020060153A1
WO2020060153A1 PCT/KR2019/011995 KR2019011995W WO2020060153A1 WO 2020060153 A1 WO2020060153 A1 WO 2020060153A1 KR 2019011995 W KR2019011995 W KR 2019011995W WO 2020060153 A1 WO2020060153 A1 WO 2020060153A1
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group
formula
carbon atoms
substituent
represented
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English (en)
Korean (ko)
Inventor
카무라료헤이
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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Priority to CN201980055560.8A priority Critical patent/CN112601736B/zh
Priority to KR1020217000123A priority patent/KR102883405B1/ko
Publication of WO2020060153A1 publication Critical patent/WO2020060153A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/49—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C07D303/06—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms in which the oxirane rings are condensed with a carbocyclic ring system having three or more relevant rings
    • 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
    • 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
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • 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
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
    • 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
    • C09B63/00—Lakes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • 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
    • 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
    • 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 a compound.
  • a color filter used for a display device such as a liquid crystal display device, an electroluminescence display device and a plasma display, or a solid-state imaging device such as a CCD or CMOS sensor is made of a colored resin composition.
  • a pigment is used as a colorant in such a colored resin composition.
  • CI Pigment Blue 24 which is a compound represented by Formula (i) is known as a pigment (Non-Patent Document 1: Color Index International (American Society of Dyeing and dyeing, American Textile Chemical Technology, Dyeing) Technical Association)).
  • C.I. Pigment Blue 24 has low heat resistance, and is not suitable for a colored resin composition for forming a color filter. Therefore, the present invention provides a compound having excellent heat resistance.
  • the present invention includes the following inventions.
  • R A1 ⁇ R A10 each independently represent a hydrogen atom, a hydroxyl group, -CO 2 -, -SO 3 - , -O -, formula (a) may have a group, or a substituent represented by the great group of 1 to 20 carbon atoms represents a group of hydrocarbons, at least two of R A1 ⁇ A10 R is, -CO 2 -, -SO 3 - , -O - represents a group represented by, or a group represented by the formula (a).
  • R A11 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • L A1 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Aa (-) is, -CO 2 -, or -SO 3 - shows a.
  • T A1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. However, the aromatic hydrocarbon group does not have -SO 3 - as a substituent.
  • An is, -CO with a compound represented by the formula (IA) 2 -, -SO 3 -, and -O - it represents the sum of the number of.
  • Am represents an integer of 1 or more.
  • AX Ak (+) represents an Ak-valent metal cation.
  • R B1 ⁇ R B10 are each independently a hydrogen atom, a hydroxyl group, -CO 2 -, -SO 3 - , -O -, formula (b) may have a group, or a substituent represented by the great group of 1 to 20 carbon atoms represents a group of hydrocarbons, at least two of R B1 ⁇ B10 is R, -CO 2 -, -SO 3 - , -O - it represents a group represented by, or the formula (b).
  • R B11 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • L B1 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Bb (-) is, -CO 2 - represents a -, or -SO 3.
  • Bn is, -CO with a compound represented by the formula (IB) 2 -, -SO 3 -, and -O - represents the sum of the number of.
  • T B1 represents a divalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent. However, the aromatic hydrocarbon group does not have -SO 3 - as a substituent.
  • L B0 represents a Bm-valent linking group.
  • Bm represents an integer of 2 or more.
  • BX Bk (+) represents a Bk-valent metal cation.
  • Bk represents an integer of 1 or more.
  • R C1 to R C4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • R C5 to R C12 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms.
  • T C1 represents a trivalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent.
  • CX Ck (+) represents a Ck-valent metal cation.
  • Ck represents an integer of 1 or more.
  • R R D1 ⁇ D10 are, each independently, a hydrogen atom, a hydroxyl group, -CO 2 -, -SO 3 - , -O -, good expression of 1 to 20 carbon atoms which may have a group, or a substituent represented by (d) represents a group of hydrocarbons, at least two of R D1 ⁇ D10 are R, -CO 2 -, -SO 3 - , -O - it represents a group represented by, or a group represented by the formula (d).
  • R D11 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • L D1 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Dd (-) is, -CO 2 - represents a -, or -SO 3.
  • T D1 represents a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. However, the aromatic hydrocarbon group does not have -SO 3 - as a substituent.
  • R D21 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • DX (+) represents a monovalent metal cation.
  • a coloring agent and a resin and the coloring agent is a compound represented by formula (IA) described in [1], a compound represented by formula (IB), a compound represented by formula (IC), and a compound represented by formula (ID)
  • a colored resin composition comprising at least one selected from the group consisting of.
  • a colored resin composition comprising the colored resin composition according to [2], a polymerizable compound, and a polymerization initiator.
  • a display device comprising the color filter according to [4].
  • a new compound excellent in heat resistance is provided. Further, according to the compound of the present invention, a color filter excellent in heat resistance can be formed.
  • the compound according to the present invention is a compound represented by formula (IA) (hereinafter sometimes referred to as compound (IA)), a compound represented by formula (IB) (hereinafter sometimes referred to as compound (IB)), formula It is a compound represented by (IC) (hereinafter, sometimes referred to as compound (IC)) or a compound represented by formula (ID) (hereinafter, sometimes referred to as compound (ID)).
  • R A1 ⁇ R A10 each independently represent a hydrogen atom, a hydroxyl group, -CO 2 -, -SO 3 - , -O -, formula (a) may have a group, or a substituent represented by the great group of 1 to 20 carbon atoms represents a group of hydrocarbons, at least two of R A1 ⁇ A10 R is, -CO 2 -, -SO 3 - , -O - represents a group represented by, or a group represented by the formula (a).
  • R A11 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • L A1 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Aa (-) is, -CO 2 - represents a -, or -SO 3.
  • T A1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. However, the aromatic hydrocarbon group does not have -SO 3 - as a substituent.
  • An is, -CO with a compound represented by the formula (IA) 2 -, -SO 3 -, and -O - it represents the sum of the number of.
  • Am represents an integer of 1 or more.
  • AX Ak (+) represents an Ak-valent metal cation.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R A1 to R A10 and R A11 include an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the like.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be either saturated or unsaturated, and the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear, branched or cyclic.
  • linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, 1-propenyl group, and 2-pro Linear aliphatic hydrocarbon groups such as phenyl groups (allyl groups); branched aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group.
  • the cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic.
  • Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • aromatic hydrocarbon group having 6 to 20 carbon atoms examples include phenyl group, xylyl group, trimethylphenyl group, dipropylphenyl group, di (2,2-dimethylpropyl) phenyl group, and naphthyl group.
  • substituent which may have a hydrocarbon group having 1 to 20 carbon atoms represented by R A1 to R A10 and R A11 , halogen atoms such as fluorine atom, chlorine atom, and iodine; hydroxyl group; carboxyl group; sulfamoyl group; nitro group; And alkoxy groups having 1 to 10 carbon atoms such as methoxy groups and ethoxy groups; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl groups and ethoxycarbonyl groups; and the like.
  • halogen atoms such as fluorine atom, chlorine atom, and iodine
  • hydroxyl group such as methoxy groups and ethoxy groups
  • alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl groups and ethoxycarbonyl groups
  • divalent aromatic hydrocarbon group represented by L A1 a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms is preferable, and one hydrogen atom contained in the monovalent aromatic hydrocarbon group in R A1 to R A10 and R A11 is bonded.
  • One hand can lift one flag.
  • compound (IA) has a plurality of groups represented by formula (a), and R A11 , L A1 , and Aa (-) are present in compound (IA), they may be the same or different.
  • Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by T A1 include a phenyl group, a xylyl group, a trimethylphenyl group, and a naphthyl group.
  • substituent which may have an aromatic hydrocarbon group having 6 to 10 carbon atoms represented by T A1 , halogen atoms such as fluorine atom, chlorine atom, and iodine; hydroxyl group; carboxyl group; sulfamoyl group; -NR x R y (R x and R y are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent); nitro group; alkoxy group having 1 to 10 carbon atoms such as methoxy group and ethoxy group; methoxycarbonyl group, And alkoxycarbonyl groups having 1 to 10 carbon atoms such as ethoxycarbonyl groups; and the like.
  • hydrocarbon group having 1 to 20 carbon atoms represented by R x and R y and the substituents that the hydrocarbon group may have are the same as R A1 to R A10 and R A11 .
  • the metal having Ak as the metal having Ak as two (ie, a divalent metal), for example, alkaline earth metals such as magnesium, calcium, strontium, and barium; zinc, copper, nickel, and manganese Transition metals, and the like, and examples of the metal having Ak is 3 (ie, a trivalent metal) include, for example, typical metals such as aluminum; transition metals such as cobalt and iron.
  • R A1 to R A10 , T A1 , An, Am, and AX Ak (+) are as follows.
  • R A1 ⁇ R A10, -CO 2 -, -SO 3 -, -O -, or a group represented by the formula (a) 2 ⁇ 6 individual is preferred, and more preferably 2-4 individual to, 2 It is more preferable that the number of dogs is three. That is, An is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 to 3.
  • compound (IA) has a substituent represented by formula (a)
  • at least two of R A1 to R A10 are groups represented by formula (a)
  • two to four groups are represented by formula (a) a, -CO 2 -, -SO 3 -, a group represented by is preferable, and two are each the formula (a) having no more than a, -CO 2 - -, -O, -SO 3 -, -O - having no It is more preferable.
  • the groups represented by multiple Formula (a) are the same.
  • Formula (a) may have a group includes, L A1 is the substituent represented by the good-phenylene methylene, methyl-phenylene-methylene group, or a dimethyl-phenylene methylene group is preferred, phenylene methylene group L A1 does not have a substituent, A methylphenylenemethylene group or a dimethylphenylenemethylene group, R A11 is a hydrogen atom or a saturated hydrocarbon group having 1 to 2 carbon atoms having no substituent, and Aa (-) is more preferably a —SO 3 — group.
  • Examples of the group represented by formula (a) include groups represented by the following formulas (a-1) to (a-8).
  • R A1 ⁇ A10 are at least two of R, -CO 2 -, -O or - two or more preferable in that, the dog 1-4 -CO 2 -, or -O-dog preferred, and 2 than to a -CO 2 -, and one is the -O-is more preferred that the.
  • the group other than the group represented by (a), a hydrogen atom, or carbon atoms, and aliphatic hydrocarbons of 1 to 20 groups are preferred, hydrogen More preferably, an atom or a linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and even more preferably a hydrogen atom or a methyl group Do.
  • the hydrogen atom is preferably 4 to 8, and more preferably 6 to 8.
  • T A1 is preferably a phenyl group which may have a substituent, a fluorine atom, a chlorine atom, a halogen atom such as iodine, or a phenyl group having -NR x R y is more preferable, and a chlorine atom or -NR as a substituent. It is more preferably a phenyl group having x R y .
  • R x is a hydrogen atom
  • R y is a hydrocarbon group which may have a substituent having 1 to 10 carbon atoms is preferred and, R y may have a substituent is an aromatic hydrocarbon group having 6 to 10 It is more preferable that R y is an aromatic hydrocarbon group having 6 to 10 carbon atoms and having an alkoxy group having 1 to 5 carbon atoms as a substituent.
  • T A1 examples include groups represented by the following formulas (aa-1) to (aa-8).
  • the metal cation of the Ak number represented by AX Ak (+) is preferably a cation of a metal having 2 to 3 of Ak (i.e., a divalent to trivalent metal), barium as a metal of Ak having 2 (i.e., a divalent metal), It is more preferably a cation of zinc or manganese.
  • Me represents a methyl group
  • a-6, aa-1, aa-2, and aa-6 respectively represent the formulas (a-6), (aa-1), (aa-2), and ( It means the group represented by aa-6).
  • R B1 ⁇ R B10 are each independently a hydrogen atom, a hydroxyl group, -CO 2 -, -SO 3 - , -O -, formula (b) may have a group, or a substituent represented by the great group of 1 to 20 carbon atoms represents a group of hydrocarbons, at least two of R B1 ⁇ B10 is R, -CO 2 -, -SO 3 - , -O - it represents a group represented by, or the formula (b).
  • R B11 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • L B1 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Bb (-) is, -CO 2 - represents a -, or -SO 3.
  • Bn is, -CO with a compound represented by the formula (IB) 2 -, -SO 3 -, and -O - represents the sum of the number of.
  • T B1 represents a divalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent. However, the aromatic hydrocarbon group does not have -SO 3 - as a substituent.
  • L B0 represents a Bm-valent linking group.
  • Bm represents an integer of 2 or more.
  • BX Bk (+) represents a Bk-valent metal cation.
  • Bk represents an integer of 1 or more.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R B1 to R B10 and R B11 include an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the like.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be either saturated or unsaturated, and the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear, branched or cyclic.
  • linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, 1-propenyl group and 2-propenyl group.
  • Linear aliphatic hydrocarbon groups such as (allyl group); branched aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group.
  • the cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic, or an aliphatic hydrocarbon group containing two or more aliphatic hydrocarbon rings.
  • Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an ethylcyclohexyl group, and a group in which one hydrogen atom of dimethylnorbornane is a bond, di A group in which one hydrogen atom of ethyl norbornane is a bond, a group in which one hydrogen atom of dimethyl adamantane is a bond, a group in which one hydrogen atom of diethyl adamantane is a bond, di (methylcyclo A group in which one hydrogen atom of hexyl) methane became a bonding group, a group
  • aromatic hydrocarbon group having 6 to 20 carbon atoms examples include phenyl group, xylyl group, trimethylphenyl group, dipropylphenyl group, di (2,2-dimethylpropyl) phenyl group, and naphthyl group.
  • Examples of the substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by R B1 to R B10 and R B11 may have include a halogen atom such as a fluorine atom, a chlorine atom, and iodine; a hydroxyl group; a carboxyl group; a sulfamoyl group; a nitro group; And alkoxy groups having 1 to 10 carbon atoms such as methoxy groups and ethoxy groups; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl groups and ethoxycarbonyl groups; and the like.
  • a halogen atom such as a fluorine atom, a chlorine atom, and iodine
  • a hydroxyl group such as methoxy groups and ethoxy groups
  • alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl groups and ethoxycarbonyl groups
  • the divalent aromatic hydrocarbon group represented by L B1 is preferably a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and monovalent aromatic hydrocarbon groups for R B1 to R B10 and R B11 (however, those having 11 to 20 carbon atoms)
  • R B1 to R B10 and R B11 Although, those having 11 to 20 carbon atoms
  • the group which made one of the hydrogen atoms contained in (not including) as a bonding hand is mentioned.
  • the compound (IB) has a plurality of groups represented by formula (b) and R B11 , L B1 , and Bb (-) are present in the compound (IB), they may be the same or different.
  • the specific example of the substituent which may have a C6-C14 divalent aromatic hydrocarbon group represented by T B1 is the same as the substituent which may have a C1-C20 hydrocarbon group represented by R B1 -R B10 and R B11 .
  • the Bm-valent linking group represented by L B0 is a divalent to pentavalent hydrocarbon group having 1 to 20 carbon atoms, and a part of -CH 2 -contained in the hydrocarbon group may be substituted with an oxygen atom or a sulfur atom, and included in the hydrocarbon group.
  • a part of > CH- to be substituted may be a nitrogen atom; it is preferred; as a divalent to pentavalent hydrocarbon group having 1 to 20 carbon atoms, a part of -CH 2 -contained in the hydrocarbon group is an oxygen atom or a sulfur atom It is more preferable that a part of> CH- contained in the hydrocarbon group is substituted with a nitrogen atom, and one or more of the oxygen atom, sulfur atom, and nitrogen atom is a group having all the bonds of the linking group. desirable.
  • the Bm-valent linking group is a group having (Bm-1) hydrogen atom contained in the monovalent hydrocarbon group in R B1 to R B10 and R B11 as a bonding group, and -CH 2 -contained in the hydrocarbon group.
  • a group in which a part of may be substituted with an oxygen atom or a sulfur atom, and a part of> CH- contained in the hydrocarbon group may be substituted with a nitrogen atom is exemplified.
  • examples of the metal having a Bk of 1 include, for example, alkali metals such as lithium, sodium, potassium, and cesium, and having Bk of 2
  • examples of the metal i.e., a divalent metal
  • alkaline earth metals such as magnesium, calcium, strontium, and barium
  • transition metals such as zinc, copper, nickel, and manganese
  • metals having a Bk of 3 ie 3)
  • R B1 to R B10 , Bn, T B1 , L B0 , Bm, and BX Bk (+) are as follows.
  • R B1 ⁇ R B10, -CO 2 -, -SO 3 -, -O -, or a group represented by the formula (b) groups represented by, 2-6 individual is preferable, more preferably 2-4 individual, 2 It is more desirable to be personal. That is, as for Bn, 2-6 are preferable, 2-4 are more preferable, and it is more preferable that it is 2.
  • R B1 to R B10 are groups represented by formula (b), and two to four groups are represented by formula (b) a, -CO 2 -, -SO 3 -, a group represented by is preferable, and two are each the formula (b) having no more than a, -CO 2 - -, -O, -SO 3 -, -O - having no It is more preferable.
  • a compound (IB) has multiple groups represented by Formula (b), it is preferable that the groups represented by multiple Formula (b) are the same.
  • L B1 is preferably a phenylenemethylene group, methylphenylenemethylene group, or dimethylphenylenemethylene group which may have a substituent, and L B1 is a phenylenemethylene group or methylphenyl having no substituent.
  • alkylene is a methylene group, or a dimethyl-phenylene-methylene group
  • R B11 is a group having a carbon number of 1-2 saturated hydrocarbon having no hydrogen atom or a substituent
  • Bb is more preferably a group - is -SO 3 ().
  • Examples of the group represented by the formula (b) include groups represented by the following formulas (b-1) to (b-8).
  • -CO 2 R represented by B1 ⁇ R B10 -, -SO 3 -, -O -, and the equation (b), each independently as the group other than the group represented by, aliphatic hydrocarbons, hydrogen atoms, or 1 to 20 carbon atoms
  • Preferred is a hydrogen atom or a linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or a methyl group. It is more preferable.
  • the hydrogen atom is preferably 4 to 8, and more preferably 6 to 8.
  • T B1 is preferably a phenylene group or a naphthylene group which may have a substituent, and a phenylene group or a naphthylene group having no substituent is more preferable.
  • L B0 is preferably a divalent hydrocarbon group having 1 to 20 carbon atoms, more preferably a divalent saturated cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms, and a group in which the carbon atom contained in the saturated cyclic aliphatic hydrocarbon group is substituted with a nitrogen atom More preferably, the carbon atom substituted with the nitrogen atom is more preferably a carbon atom linked to T B1 .
  • Bm As for Bm, 2-5 are preferable, 2-3 are more preferable, and 2 is the most preferable.
  • the Bk-valent metal cation represented by BX Bk (+) is preferably a cation of a metal having Bk of 1 to 3 (i.e., a monovalent to trivalent metal), barium as a metal having Bk of 2 (i.e., a divalent metal), It is more preferably a cation of zinc or manganese.
  • Me represents a methyl group
  • phe represents a phenylene group
  • naph represents a naphthylene group
  • b-6, b-7, LB-3, and LB-4 represent the formulas (b-6) and (b-), respectively.
  • 7) means the group represented by (LB-3) and (LB-4).
  • R C1 to R C4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • R C5 to R C12 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms.
  • T C1 represents a trivalent aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent.
  • CX Ck (+) represents a Ck-valent metal cation.
  • Ck represents an integer of 1 or more.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R C1 to R C4 include an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the like.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be either saturated or unsaturated, and the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear, branched or cyclic.
  • linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, 1-propenyl group and 2-propenyl group.
  • Linear aliphatic hydrocarbon groups such as (allyl group); branched aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group.
  • the cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic.
  • Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • aromatic hydrocarbon group having 6 to 20 carbon atoms examples include phenyl group, xylyl group, trimethylphenyl group, dipropylphenyl group, di (2,2-dimethylpropyl) phenyl group, and naphthyl group.
  • Examples of the substituent which may have a hydrocarbon group having 1 to 20 carbon atoms represented by R C1 to R C4 include halogen atoms such as fluorine atom, chlorine atom and iodine; hydroxy group; carboxyl group; sulfamoyl group; nitro group; methoxy group and ethoxy. And an alkoxy group having 1 to 10 carbon atoms such as a period; an alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group; and the like.
  • hydrocarbon group having 1 to 8 carbon atoms represented by R C5 to R C12 and the substituents that the hydrocarbon group may have are the same as those of R C1 to R C4 except that those having 9 to 20 carbon atoms are not included.
  • T C1 As a trivalent aromatic hydrocarbon group having 6 to 14 carbon atoms represented by T C1 , two hydrogen atoms contained in a monovalent aromatic hydrocarbon group in R C1 to R C4 (however, those having 15 to 20 carbon atoms are not included) And a group with a bonding hand.
  • T C1 The specific example of the substituent which may have a C6- C14 trivalent aromatic hydrocarbon group represented by T C1 is the same as the substituent which the C1 -C20 hydrocarbon group represented by R C1 -R C4 may have.
  • examples of the metal having Ck 1 include alkali metals such as lithium, sodium, potassium, and cesium, and Ck is 2
  • examples of the metal (ie, a divalent metal) include alkali earth metals such as magnesium, calcium, strontium, and barium; transition metals such as zinc, copper, nickel, and manganese; and metals having a Ck of 3 (ie, 3) As a pseudo metal), typical metals, such as aluminum; transition metals, such as cobalt and iron, are mentioned, for example.
  • R C1 to R C12 , T C1 and CX Ck (+) are as follows.
  • Each of R C1 to R C4 is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a saturated chain aliphatic hydrocarbon group having 1 to 8 carbon atoms, and a saturated linear chain having 1 to 5 carbon atoms. It is more preferably an aliphatic hydrocarbon group, and more preferably a methyl group or an ethyl group.
  • R C1 to R C4 are preferably R C1 and R C3 , and R C2 and R C4 are the same group, and more preferably R C1 to R C4 are the same group.
  • Each of R C5 to R C12 is preferably a hydrogen atom or a saturated linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrogen atom.
  • T C1 is preferably a trivalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, a trivalent aromatic hydrocarbon group having 6 to 10 carbon atoms having no substituent, or 3 to 6 carbon atoms having a hydroxy group as a substituent.
  • a pseudo aromatic hydrocarbon group is more preferable.
  • Examples of the group in which two -SO 3 - are bonded to T C1 include groups represented by the following formulas (cc-1) to (cc-22).
  • the Ck-valent metal cation represented by CX Ck (+) is preferably a cation of a metal having Ck of 1 to 3 (i.e., a monovalent to trivalent metal), barium as a metal having Ck of 2 (that is, a divalent metal), It is more preferably a cation of zinc or manganese.
  • Me represents a methyl group
  • Et represents an ethyl group
  • cc-3, cc-8, and cc-20 are represented by the formulas (cc-3), (cc-8), and (cc-20), respectively.
  • R R D1 ⁇ D10 are, each independently, a hydrogen atom, a hydroxyl group, -CO 2 -, -SO 3 - , -O -, good expression of 1 to 20 carbon atoms which may have a group, or a substituent represented by (d) represents a group of hydrocarbons, at least two of R D1 ⁇ D10 are R, -CO 2 -, -SO 3 - , -O - it represents a group represented by, or a group represented by the formula (d).
  • R D11 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • L D1 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Dd (-) is, -CO 2 - represents a -, or -SO 3.
  • T D1 represents a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. However, the aromatic hydrocarbon group does not have -SO 3 - as a substituent.
  • R D21 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • DX (+) represents a monovalent metal cation.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R D1 to R D10 , R D11 and R D21 include an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the like.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be either saturated or unsaturated, and the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear, branched or cyclic.
  • linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, 1-propenyl group and 2-propenyl group.
  • Linear aliphatic hydrocarbon groups such as (allyl group); branched aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group.
  • the cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic.
  • Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • aromatic hydrocarbon group having 6 to 20 carbon atoms examples include phenyl group, xylyl group, trimethylphenyl group, dipropylphenyl group, di (2,2-dimethylpropyl) phenyl group, and naphthyl group.
  • Examples of the substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by R D1 to R D10 , R D11 , and R D21 may have include a halogen atom such as a fluorine atom, a chlorine atom, and iodine; a hydroxyl group; a carboxyl group; a sulfamoyl group; And nitro groups; alkoxy groups having 1 to 10 carbon atoms such as methoxy groups and ethoxy groups; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl groups and ethoxycarbonyl groups; and the like.
  • a halogen atom such as a fluorine atom, a chlorine atom, and iodine
  • a hydroxyl group such as methoxy groups and ethoxy groups
  • alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl groups and ethoxycarbonyl groups
  • the divalent aromatic hydrocarbon group represented by L D1 is preferably a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and 1 of the hydrogen atom contained in the monovalent aromatic hydrocarbon group in R D1 to R D10 , R D11 , and R D21 .
  • One group is a dog with a bonding hand.
  • substituent which the divalent aromatic hydrocarbon group represented by L D1 may have, it is the same as the substituent which may have a hydrocarbon group having 1 to 20 carbon atoms represented by R D1 to R D10 , R D11 , and R D21 .
  • the compound (ID) has a plurality of groups represented by formula (d) and R D11 , L D1 , and Dd (-) are present in the compound (ID), they may be the same or different.
  • Examples of the divalent aromatic hydrocarbon group having 6 to 10 carbon atoms represented by T D1 include monovalent aromatic hydrocarbon groups in R D1 to R D10 , R D11 , and R D21 (however, those having 11 to 20 carbon atoms are not included). And a group in which one of the hydrogen atoms contained is a bonding hand.
  • alkali metals such as lithium, sodium, potassium, and cesium, etc. are mentioned, for example.
  • R D1 to R D10 , T D1 , R D21 and DX (+) are as follows.
  • R D1 ⁇ R D10, -CO 2 -, -SO 3 -, -O -, or a group represented by the formula (d) 2 ⁇ 6 gae individual is preferable, more preferably 2-4 individual, 2 It is more desirable to be personal.
  • R D1 to R D10 are groups represented by formula (d), and two to four groups are represented by formula (d) a, -CO 2 -, -SO 3 -, a group represented by is preferable, and the two are formula (d) than with no, -CO 2 - -, -O, -SO 3 -, -O - having no It is more preferable.
  • the groups represented by multiple Formula (d) are the same.
  • L D1 a may have a substituent a benzyl group, a methylbenzyl group, or a dimethyl benzyl group is preferable and, L D1 is no substituent a benzyl group, a methylbenzyl group, or a dimethyl-phenylene group , R D11 is a hydrogen atom or a saturated hydrocarbon group having 1 to 2 carbon atoms having no substituent, and a group in which Dd (-) is -SO 3 - is more preferable.
  • Examples of the group represented by the formula (d) include groups represented by the following formulas (d-1) to (d-8).
  • R ⁇ -CO D1 represented by R D10 2 -, -SO 3 - , -O -, and expression as a group other than groups shown by (d), the hydrogen atom or preferably an aliphatic hydrocarbon group of 1 to 20 carbon atoms, and hydrogen More preferably, an atom or a linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a linear aliphatic hydrocarbon group having 1 to 5 carbon atoms, and even more preferably a hydrogen atom or a methyl group Do.
  • the hydrogen atom is preferably 4 to 8, and more preferably 6 to 8.
  • T D1 is preferably a phenylene group which may have a substituent, and more preferably a phenylene group having no substituent.
  • R D21 is preferably a phenylene group which may have a substituent, and more preferably a phenylene group having an alkoxy group having 1 to 5 carbon atoms as the substituent.
  • R D21 examples include groups represented by the following formulas (dd-1) to (dd-8).
  • the monovalent metal cation represented by DX (+) is preferably an alkali metal cation, more preferably a cesium cation.
  • Me represents a methyl group
  • phe represents a phenylene group
  • d-6, d-7, dd-1, and dd-4 represent the formulas (d-6), (d-7), and (dd), respectively. It means the group represented by -1) and (dd-4).
  • Compound (IA), compound (IB), compound (IC), and compound (ID) can be produced according to a known method.
  • it can be produced by reacting a known dye with an acetate, carbonate, phosphate, sulfate, silicate, cyanide or halide (preferably chloride) of the r-valent metal ion M r + .
  • a manufacturing method of the connection part of a compound (IB) you may refer suitably to International Publication No. 2018/003708.
  • the colored resin composition of the present invention includes a colorant (hereinafter sometimes referred to as “colorant (A)”) and a resin (hereinafter sometimes referred to as “resin (B)”), and the colorant (A) is , Compound (IA), compound (IB), compound (IC), and compound (ID).
  • colorant (A) a colorant
  • resin (B) a resin
  • the colorant (A) is , Compound (IA), compound (IB), compound (IC), and compound (ID).
  • the colored resin composition of the present invention further contains a polymerizable compound (hereinafter sometimes referred to as “polymerizable compound (C)”) and a polymerization initiator (hereinafter sometimes referred to as “polymerization initiator (D)”). It is preferred to include.
  • a polymerizable compound hereinafter sometimes referred to as “polymerizable compound (C)”
  • a polymerization initiator hereinafter sometimes referred to as “polymerization initiator (D)
  • the colored resin composition of the present invention further includes a polymerization initiation aid (hereinafter sometimes referred to as “polymerization initiation aid (D1)”), a solvent (hereinafter sometimes referred to as “solvent (E)”), and a leveling agent. (Hereinafter, it may be called “leveling agent (F)").
  • a polymerization initiation aid hereinafter sometimes referred to as “polymerization initiation aid (D1)
  • solvent hereinafter sometimes referred to as “solvent (E)”
  • leveling agent (F) leveling agent
  • the colored resin composition of the present invention contains at least one selected from the group consisting of compound (IA), compound (IB), compound (IC), and compound (ID) as the colorant (A).
  • the content of the compound (IA), the compound (IB), the compound (IC), and / or the compound (ID) is preferably 0.1 to 150 parts by mass, and 0.5 to 100 parts by mass with respect to 100 parts by mass of the resin (B). It is more preferable, and it is still more preferable that it is 1 to 80 parts by mass.
  • the content of the compound (IA), the compound (IB), the compound (IC), and / or the compound (ID) is preferably 50% by mass or more, more preferably 80% by mass or more, among the total amount of the colorant (A). , More preferably, it is 90% by mass or more.
  • the colored resin composition of the present invention may contain a dye (A1) and a pigment (A2) in addition to the compound (IA), compound (IB), compound (IC), and / or compound (ID) as the colorant (A). good.
  • the dye (A1) is not particularly limited and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes.
  • the dye for example, a compound classified as having a color other than the pigment in the color index (published by The Society of Dyers and Colourists), or a known dye described in a dyeing note (dyeing yarn).
  • azo dyes cyanine dyes, triphenylmethane dyes (except compound (IA), compound (IB), compound (IC), and compound (ID)), xanthene dye, phthalocyanine dye , Anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, scaryrium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.
  • the pigment (A2) is not particularly limited, and a known pigment can be used, and examples thereof include pigments classified as pigments in a color index (published by The Society of Dyers and Colourists).
  • C.I. Red pigments such as Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 ;
  • C.I. Blue pigments such as Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;
  • C.I. Violet pigments such as pigment violet 1, 19, 23, 29, 32, 36, 38;
  • C.I. Green pigments such as Pigment Green 7, 36, and 58;
  • the content rate of the colorant (A) is preferably 0.1 to 70% by mass, more preferably 0.5 to 60% by mass, and even more preferably 1 to 50% by mass, with respect to the total amount of solids in the colored resin composition.
  • total amount of solid content in the present specification refers to the amount of the content of the solvent excluding the total amount of the colored resin composition or colored curable resin composition.
  • the total amount of the solid content and the content of each component thereof can be measured by known analytical means such as liquid chromatography or gas chromatography.
  • the resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as "(a)") It is more preferable to have a resin having a structural unit derived from).
  • the resin (B) further comprises a structural unit derived from a monomer (b) (hereinafter sometimes referred to as “(b)”) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and (a) A structural unit derived from a copolymerizable monomer (c) (however, (a) and (b) are different) (hereinafter sometimes referred to as "(c)”), and an ethylenically unsaturated bond in the side chain. It is preferable to have at least one structural unit selected from the group consisting of structural units.
  • (a) specifically, for example, acrylic acid, methacrylic acid, maleic anhydride, itaconic acid anhydride, 3,4,5,6-tetrahydrophthalic anhydride, succinic acid mono [2- (meth) acrylo. Iloxyethyl] etc. are mentioned, Preferably it is acrylic acid, methacrylic acid, maleic anhydride.
  • (b) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and a (meth) acryloyloxy group. Is preferred.
  • (meth) acrylic acid means at least 1 sort (s) selected from the group which consists of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” also have the same meaning.
  • glycidyl (meth) acrylate, vinylbenzyl glycidyl ether, 3,4-epoxycitcyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl -3-((meth) acryloyloxymethyl oxetane, tetrahydrofurfuryl (meth) acrylate, etc. are mentioned,
  • (c) for example, methyl (meth) acrylate, butyl (meth) acrylate cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6 Decane-8-yl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decane-9-yl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate , N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyl toluene, and the like.
  • Resin having a structural unit having an ethylenically unsaturated bond in the side chain (b) is added to the copolymer of (a) and (c), or (a) is added to the copolymer of (b) and (c). Can be produced.
  • the resin may be obtained by adding (a) to the copolymer of (b) and (c) and further reacting carboxylic anhydride.
  • the weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.
  • the dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
  • the acid value of the resin (B) is preferably 20 to 170 mg-KOH / g in terms of solid content, more preferably 30 to 150 mg-KOH / g, more preferably 40 to 135 mg-KOH / g.
  • the acid value is a value measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.
  • the content ratio of the resin (B) is preferably 5 to 65% by mass, more preferably 15 to 60% by mass, and even more preferably 20 to 55% by mass with respect to the total amount of solid content of the colored resin composition.
  • the polymerizable compound (C) is a compound capable of polymerizing with an active radical and / or acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and the like. It is a (meth) acrylic acid ester compound.
  • a polymerizable compound (C) is a polymerizable compound which has three or more ethylenically unsaturated bonds.
  • a polymerizable compound trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, for example And dipentaerythritol hexa (meth) acrylate.
  • the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.
  • the content of the polymerizable compound (C) is preferably 5 to 65 mass%, more preferably 15 to 60 mass%, and even more preferably, based on the total amount of solid content. It is 20-55 mass%.
  • the polymerization initiator (D) generates active radicals, acids, and the like by the action of light or heat, and any known polymerization initiator can be used without particular limitation as long as it is a compound capable of initiating polymerization.
  • a polymerization initiator generating an active radical for example, N-benzoyloxy-1 (4-phenylsulfanylphenyl) butane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfur Panylphenyl) octane-1 -on-2 -imine, N-benzoyloxy -1-(4 -phenylsulfanylphenyl) -3 -cyclopentylpropane -1 -on -2 -imine, N -acetyloxy -1- (4-phenylsulfanylphenyl) -3-cyclohexylpropan-1-one-2-imine, 2-methyl-2-morpholino-1-1 (4-methyl
  • the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 100 parts by mass relative to the total amount of the resin (B) and the polymerizable compound (C). It is 1 to 20 parts by mass.
  • the productivity of the color filter improves because it tends to increase the sensitivity and shorten the exposure time.
  • the polymerization initiation assistant (D1) is a compound or a sensitizer used to accelerate polymerization of the polymerizable compound in which polymerization is initiated by the polymerization initiator.
  • a polymerization start adjuvant (D1) is included, it is usually used in combination with a polymerization initiator (D).
  • polymerization initiation assistant (D1) 4,4'-bis (dimethylamino) benzophenone (commonly known as mihira's ketone), 4,4'-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 2,4-diethyl thioxanthone, N-phenylglycine, etc. are mentioned.
  • the content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is the mass part.
  • the amount of the polymerization start adjuvant (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.
  • the solvent (E) is not particularly limited, and a solvent commonly used in the field can be used.
  • a solvent commonly used in the field can be used.
  • ester solvents solvents containing -COO- in the molecule and not containing -O-
  • ether solvents solvents containing -O- in the molecule, and not containing -COO-
  • ether esters Solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (containing OH in the molecule,- And solvents not containing O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.
  • Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and ⁇ -butyrolactone (in the molecule- COO- and solvents not containing -O-);
  • Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether (-O- in the molecule) And solvents that do not contain -COO-);
  • Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate (in the molecule) -Solvent containing -COO- and -O-);
  • Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, cyclohexanone (containing -CO- in the molecule, and -COO Solvent containing no -);
  • Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-);
  • amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone; and the like.
  • solvent (E) propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, N-methylpyrrolidone, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate and 3- Ethoxypropionate ethyl is more preferred.
  • the content of the solvent (E) is preferably 60 to 97 mass%, more preferably 65 to 95 mass%, based on the total amount of the colored resin composition of the present invention.
  • the total amount of the solid content of the colored resin composition is preferably 3 to 40% by mass, more preferably 5 to 35% by mass.
  • leveling agent (F) examples include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.
  • Torrey Silicon DC3PA, Copper SH7PA, Copper DC11PA, Copper SH21PA, Copper SH28PA, Copper SH29PA, Copper SH30PA, Copper 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 and TSF4460 (manufactured by Momentive Performance Materials, Japan) have.
  • fluorochemical surfactant As said fluorochemical surfactant, surfactant etc. which have a fluorocarbon chain in a molecule
  • numerator are mentioned. Specifically, Florad (registered trademark) FC430, copper FC431 (Sumitomo 3M Co., Ltd.), Megapack (registered trademark) F142D, copper F171, copper F172, copper F173, copper F177, copper F183, copper F554, copper R30, copper RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, copper EF303, copper EF351, copper EF352 (Mitsubishi Material Electronics Co., Ltd.), supron (registered trademark) S381 , Copper S382, copper SC101, copper SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Tablet Chemical Co., Ltd.).
  • silicone type surfactant which has the said fluorine atom, surfactant etc. which have a siloxane bond and a fluorocarbon chain in a molecule
  • numerator Specifically, Megapack (trademark) R08, copper BL20, copper F475, copper F477, copper F443 (made by DIC Corporation) etc. are mentioned.
  • the content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, and more preferably 0.002 to 0.1% by mass, with respect to the total amount of the colored resin composition.
  • the content of the pigment dispersant is not included in this content.
  • the colored resin composition of the present invention may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, if necessary.
  • the colored resin composition of the present invention includes a colorant (A) and a resin (B), and a polymerizable compound (C), a polymerization initiator (D), a polymerization initiator (D1), a solvent (E), and leveling as needed. It can be prepared by mixing the agent (F) and other components.
  • a photolithography method As a method of manufacturing a colored pattern with the colored resin composition of the present invention, a photolithography method, an inkjet method, a printing method, and the like can be mentioned. Especially, the photolithography method is preferable.
  • the colored resin composition contains a compound (IA), a compound (IB), a compound (IC), and / or a compound (ID) excellent in heat resistance
  • a color filter excellent in heat resistance can be produced.
  • the color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices.
  • C.I. Pigment Blue 24 was used as a comparative example.
  • the flask was equipped with a reflux cooler, a dropping lot, and a stirrer, and nitrogen was flowed in an appropriate amount to replace it with a nitrogen atmosphere, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85 ° C while stirring.
  • the mixture was kept at the same temperature for 4 hours, cooled to room temperature, and a copolymer (resin (B-X)) solution having a solid content of 25.6% was obtained.
  • the weight average molecular weight Mw of the produced copolymer was 8000, dispersion degree 2.1, and acid value in terms of solid content was 111 mg-KOH / g.
  • the resin (B-X) has the following structural units.
  • the measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) of polystyrene conversion of resin was performed on the following conditions by GPC method.
  • HLC-8120 GPC manufactured by Tosoh Corporation
  • the ratio (Mw / Mn) of the weight average molecular weight and number average molecular weight in terms of polystyrene obtained above was defined as the dispersion degree.
  • the colored curable resin composition was coated on a 5 cm edge glass substrate (Eagle 2000; manufactured by Corning) by spin coating so that the film thickness after post-baking was 2 ⁇ m, and then pre-baked at 100 ° C. for 3 minutes. After cooling, post-baking was performed in an oven at 230 ° C for 20 minutes to obtain a color filter. This color filter shows high heat resistance.
  • the present invention provides a compound having excellent heat resistance, a colored resin composition containing the same, a color filter, and a display device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Structural Engineering (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials For Photolithography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
  • Optical Filters (AREA)
  • Epoxy Compounds (AREA)

Abstract

La présente invention concerne un composé présentant une excellente résistance à la chaleur, et une composition de résine colorée, un filtre coloré et un dispositif d'affichage le comprenant.
PCT/KR2019/011995 2018-09-19 2019-09-17 Composé, composition de résine colorée, filtre coloré et dispositif d'affichage Ceased WO2020060153A1 (fr)

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CN201980055560.8A CN112601736B (zh) 2018-09-19 2019-09-17 化合物、着色树脂组合物、滤色器及显示装置
KR1020217000123A KR102883405B1 (ko) 2018-09-19 2019-09-17 화합물, 착색 수지 조성물, 컬러 필터 및 표시 장치

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TW202022051A (zh) 2020-06-16
CN112601736A (zh) 2021-04-02
KR102883405B1 (ko) 2025-11-06
TWI856975B (zh) 2024-10-01
KR20210046647A (ko) 2021-04-28
JP2020045436A (ja) 2020-03-26
CN112601736B (zh) 2023-12-08

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