WO2015083605A1 - 新規化合物及び該化合物を含有する組成物 - Google Patents

新規化合物及び該化合物を含有する組成物 Download PDF

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Publication number
WO2015083605A1
WO2015083605A1 PCT/JP2014/081360 JP2014081360W WO2015083605A1 WO 2015083605 A1 WO2015083605 A1 WO 2015083605A1 JP 2014081360 W JP2014081360 W JP 2014081360W WO 2015083605 A1 WO2015083605 A1 WO 2015083605A1
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group
carbon atoms
compound
represented
general formula
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PCT/JP2014/081360
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English (en)
French (fr)
Japanese (ja)
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依純 松井
俊彦 村井
光裕 岡田
有希子 金原
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株式会社Adeka
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Priority to KR1020167001471A priority Critical patent/KR20160088282A/ko
Priority to CN201480040980.6A priority patent/CN105637038B/zh
Priority to JP2015551480A priority patent/JP6518195B2/ja
Priority to KR1020217041431A priority patent/KR102369427B1/ko
Publication of WO2015083605A1 publication Critical patent/WO2015083605A1/ja

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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/20—Light-sensitive devices
    • H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/20—Light-sensitive devices
    • H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
    • H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells

Definitions

  • the present invention relates to an organic dye compound having a phenolic antioxidant structure and a composition containing the compound. Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the composition, and a color filter that uses the colored photosensitive composition.
  • Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • an optical filter for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display, etc.
  • Various compounds that absorb light having a wavelength of ⁇ 1100 nm are used as light absorbers. These light absorbers are required to have particularly steep light absorption, that is, having a small half-value width of ⁇ max and not to lose its function due to light, heat, or the like.
  • An optical filter mainly used for a liquid crystal display includes a color filter.
  • three primary colors of RGB have been used for a color filter, but it is difficult to have a pure RGB hue with a single color material, and a pure RGB hue using a plurality of color materials. Efforts have been made to get closer to. Therefore, color materials such as yellow, orange and purple are required instead of RGB.
  • Organic and / or inorganic pigments have been used as light absorbers for color filters due to their high heat resistance. However, since they are pigments, there is a problem in that the luminance of a display device is lowered. This problem has been solved by increasing the brightness of the. However, with the trend toward lower power consumption, development of color filters using dyes has become active.
  • Patent Documents 1 to 3 disclose colored resin compositions for color filters containing an organic dye having a specific structure.
  • Patent Documents 4 and 5 disclose a coloring composition for a color filter containing a pigment and an antioxidant.
  • the compounds used in the coloring compositions for color filters described in these documents are not satisfactory in terms of heat resistance.
  • an object of the present invention is to provide a colored photosensitive composition (colored alkali-developable photosensitive composition) having excellent heat resistance.
  • Another object of the present invention is an optical filter using the colored photosensitive composition (colored alkali-developable photosensitive composition), particularly suitable for an image display device such as a liquid crystal display panel without reducing luminance. It is to provide a color filter.
  • a compound having a specific structure is excellent in heat resistance, and a colored photosensitive composition (colored alkali-developable photosensitive composition) using this compound.
  • a color filter for an image display device such as a liquid crystal display panel without reducing the luminance of an optical filter (particularly a color filter), and has reached the present invention.
  • the present invention has been made based on the above findings, and is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region, wherein 1 to 1 substituents represented by the following general formula (1) are present in the molecule.
  • a compound having 10 is provided.
  • R 01 , R 02 , R 03 , R 04 and R 05 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms.
  • R 01 , R 02 , R 03 , R 04 and R 05 is represented by —O—R 1 ;
  • R 1 is a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a heterocyclic ring-containing group having 2 to 20 carbon atoms, or Represents a trialkylsilyl group,
  • the alkyl group, aryl group, arylalkyl group or heterocyclic ring-containing group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 has a substituent or is unsubstituted, The methylene group in the alkyl group or
  • R 2 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • the present invention also relates to an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region, wherein the compound has 1 to 10 substituents represented by the following general formula (1) in the molecule:
  • the composition containing this is provided.
  • the present invention also provides a colored photosensitive composition containing a polymerizable compound having an ethylenically unsaturated bond having an acid value and a radical photopolymerization initiator in addition to the above composition.
  • the colored photosensitive composition (colored alkali-developable photosensitive composition) of the present invention containing a compound having a specific structure is excellent in heat resistance. Moreover, the cured product is suitable for a color filter for a display device.
  • the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region and having at least one structure represented by the general formula (1) in the molecule will be described.
  • the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region is not particularly limited as long as it is a compound having an absorption maximum in the ultraviolet to near-infrared wavelength region, that is, 380 to 1200 nm.
  • the method for introducing the structure represented by the general formula (1) into the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region is not particularly limited, and examples thereof include a method using a known reaction. However, for example, a method utilizing a reaction such as esterification or amidation can be mentioned.
  • the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region has a structure in which 1 to 10 substituents represented by the general formula (1) are bonded. When there are a plurality of substituents, they may be the same or different. The number of substituents is preferably 2 to 6 from the viewpoint of ease of synthesis.
  • Examples of the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 in the general formula (1) include fluorine, chlorine, bromine and iodine.
  • Examples of the alkyl group having 1 to 40 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert -Butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-oc
  • Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl group, 2- Phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and the like,
  • Examples of the heterocyclic group containing 2 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl and pyrrolyl.
  • Examples of the substituent for substituting the alkyl group, aryl group, arylalkyl group and heterocyclic-containing group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include vinyl, allyl, acryl, methacryl Ethylenically unsaturated groups such as fluorine, chlorine, bromine, iodine and the like; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, Acyl groups such as pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl; acyloxy
  • the methylene group in the alkyl group or arylalkyl group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S.
  • —, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR 2 —,> P ⁇ O, —SS— or —SO 2 — may be substituted.
  • the position and number are arbitrary.
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R 2 include R 01 , R 02 , R 03 , R 04 and R 05 and the alkyl group having 1 to 40 carbon atoms represented by R 1. Among these, groups satisfying a predetermined number of carbon atoms are exemplified.
  • R 02 or R 04 is an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, or 7 to 20 carbon atoms.
  • R 03 is —O—R 1 , particularly R 1 is a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms
  • R 1 is a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms
  • at least one of R 02 or R 04 is an alkyl group having 1 to 40 carbon atoms, or 6 to 20 carbon atoms.
  • R 1 is a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms; and R 02 or R 04 At least one of those is an alkyl group having 1 to 10 carbon atoms is preferred from the viewpoint of heat resistance.
  • alkoxycarbonyl group having 2 to 9 carbon atoms examples include methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl, s-butyloxycarbonyl, t-butyloxycarbonyl, isobutyloxycarbonyl Pentyloxycarbonyl, isoamyloxycarbonyl, t-amyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, cyclohexylmethyloxycarbonyl, tetrahydrofuranyloxycarbonyl, tetrahydropyranyloxycarbonyl and the like.
  • a cyanostyrene compound a triarylmethane compound, and a cyanine compound are preferable from the viewpoint of ease of synthesis and molecular design.
  • cyanostyrene compounds those represented by the following general formula (2) are preferable from the viewpoint of ease of synthesis and molecular design.
  • A represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings represent the substituent represented by the general formula (1), a halogen atom, a cyano group, a hydroxyl group, a nitro group, and the number of carbon atoms.
  • R 5 represents a hydrogen atom, a phenyl group, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a halogenated alkyl group having 1 to 8 carbon atoms.
  • Y represents a cyano group or —COOR 8
  • R 8 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a substituent represented by the general formula (1)
  • the methylene group in the alkyl group represented by R 8 may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • X is a single bond, a nitrogen atom, —NR 9 —, an oxygen atom, a sulfur atom, a phosphorus atom, —PR 10 —, or an organic group that satisfies any of the following ⁇ 1> to ⁇ 5>, and Bonded to any one or more of R 8 , A, R 6 or R 7 when Y is represented by —COOR 8 ;
  • R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a substitu
  • the alkyl group, aryl group and arylalkyl group represented by R 6 , R 7 , R 9 and R 10 are substituted with a substituent represented by the above general formula (1), a halogen atom, a hydroxyl group or a nitro group.
  • a substituent represented by the above general formula (1) a halogen atom, a hydroxyl group or a nitro group.
  • the methylene group in the alkyl group and arylalkyl group represented by R 6 , R 7 , R 9 and R 10 is —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—. May be replaced with m is an integer from 1 to 6, It has at least one substituent represented by the general formula (1) in the molecule. )
  • X 1 is —NR 13 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, or a divalent carbon atom.
  • the methylene group in the aliphatic hydrocarbon group represented by X 1 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof.
  • Z 1 and Z 2 each independently represents a direct bond, —O—, —S—, —SO 2 —, —SO—, —NR 13 —, —PR 14 —
  • R 13 and R 14 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms,
  • the alkyl group, aryl group and arylalkyl group represented by R 13 and R 14 may be substituted with a halogen atom, a hydroxyl group or a nitro group
  • the methylene group in the alkyl group and arylalkyl group represented by R 13 and R 14 may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—.
  • the group represented by the general formula (3) is in the range of 1 to 35 carbon atoms.
  • R 21 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a phenyl group which may be substituted by an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.
  • R 22 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom
  • the alkyl group, alkoxy group and alkenyl group represented by R 21 and R 22 are substituted with a halogen atom or unsubstituted, d is an integer of 0 to 5.
  • R 23 and R 24 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or 6 carbon atoms
  • the alkyl group, aryl group, aryloxy group, arylthio group, arylalkenyl group, arylalkyl group and heterocyclic group-containing group represented by R 23 and R 24 are substituted with a halogen atom or unsubstituted
  • the methylene group in the alkyl group and arylalkyl group represented by R 23 and R 24 may be replaced with an unsaturated bond, —O— or —S—
  • X 2 represents a carbon atom substituted with R 25 , a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, Represents a trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or a trivalent heterocyclic group having 2 to 35 carbon atoms, R 25 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
  • the methylene group in the aliphatic hydrocarbon group represented by X 2 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof.
  • Z 1 to Z 3 are each independently the same as the groups represented by Z 1 and Z 2 in the general formula (3). However, the group represented by the general formula (4)
  • X 3 represents a carbon atom, an aliphatic hydrocarbon group having 1 to 35 tetravalent carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a tetravalent carbon atom number
  • the methylene group in the aliphatic hydrocarbon group represented by X 3 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof.
  • Z 1 to Z 4 are independently the same as the groups represented by Z 1 and Z 2 in the general formula (3).
  • the group represented by the general formula (5) is in the range of 1 to 35 carbon atoms.
  • X 4 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, or a pentavalent carbon atom having 6 to 35 carbon atoms.
  • An aromatic ring-containing hydrocarbon group or a pentavalent heterocyclic group having 2 to 35 carbon atoms The methylene group in the aliphatic hydrocarbon group represented by X 4 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof.
  • Z 1 to Z 5 are each independently the same as the groups represented by Z 1 and Z 2 in the general formula (3). However, the group represented by the general formula (6) is in the range of 2 to 35 carbon atoms.
  • X 5 is a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a hexavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, or a hexavalent carbon atom having 6 to 35 carbon atoms.
  • An aromatic ring-containing hydrocarbon group or a hexavalent heterocyclic group having 2 to 35 carbon atoms The methylene group in the aliphatic hydrocarbon group represented by X 5 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof.
  • Z 1 to Z 6 are independently the same as the groups represented by Z 1 and Z 2 in the general formula (3). However, the group represented by the general formula (7) is in the range of 2 to 35 carbon atoms.
  • the benzene ring represented by A, the naphthalene ring and the halogen atom which may be substituted for the anthracene the halogen atom represented by R 5 , and R 6 , R 7 , R 9 and R 10
  • the groups exemplified as the halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 Named, Examples of the alkyl group having 1 to 8 carbon atoms which may be substituted on the benzene ring, naphthalene ring and anthracene represented by A, and the alkyl group having 1 to 8 carbon atoms represented by R 5 to R 10 include R 01 , R 02 , R 03 , R 04 and R 05 and the groups exemplified as the alkyl group having 1 to 40 carbon
  • Benzene ring represented by A as the naphthalene ring and anthracene substituted alkoxy group having 1 to 8 carbon atoms, also represented by an alkoxy group, and R 5 a good carbon number of 1 to 8 and, methoxy, ethoxy, Propyloxy, isopropyloxy, butyloxy, s-butyloxy, t-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, t-amyloxy, hexyloxy, cyclohexyloxy, cyclohexylmethyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, etc.
  • halogenated alkyl group having 1 to 8 carbon atoms and the halogenated alkyl group having 1 to 8 carbon atoms represented by R 5 that may be substituted on the benzene ring, naphthalene ring and anthracene represented by A , Wherein at least one hydrogen atom of the alkyl group having 1 to 8 carbon atoms is replaced by the halogen atom described above, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, fluoromethyl, trifluoromethyl, Nonafluorobutyl and the like, Examples of the halogenated alkoxy group having 1 to 8 carbon atoms and the halogenated alkoxy group having 1 to 8 carbon atoms represented by R 5 that may be substituted on the benzene ring, naphthalene ring and anthracene represented by A , Wherein at least one hydrogen atom of the alkoxy group having 1 to 8 carbon atoms is replaced by
  • Examples include the groups exemplified as the aryl group of formula 6 to 20, Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 6 , R 7 , R 9 and R 10 include carbon represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1. Examples thereof include arylalkyl groups having 7 to 20 atoms.
  • Examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 1 in the general formula (3) include methane, ethane, propane, iso-propane, butane, sec-butane, and tert-butane.
  • Examples of the combination of these include, for example, —COO—O—, —COO—S—, —O—OCO—, —S—OCO—, —CO—NH.
  • Examples of the divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by X 1 include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2-adamantyl, noradamantyl, 2- Methyl adamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [3 .1.0] hexyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.0] hexyl, bicyclo [4.1.0] heptyl, bicyclo [3.2.0] heptyl, bicyclo [3 1.1] heptyl, bicyclo [3 1.1
  • octyl bicyclo [4.1.1] octyl, bicyclo [3.3.0] octyl, bicyclo [3.2.1] octyl, bicyclo [2.2.2] octyl, spiro [4,4 ]
  • Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by X 1 include divalent groups in which groups such as phenyl, naphthyl, and biphenyl are substituted with Z 1 and Z 2.
  • Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by X 1 include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene. And divalent groups in which a group such as thiolane is substituted with Z 1 and Z 2 . These groups may be further substituted with a halogen atom, a cyano group, a nitro group or an alkoxy group having 1 to 8 carbon atoms.
  • groups satisfying a predetermined carbon number can be mentioned
  • Examples of the aryl group having 6 to 20 carbon atoms represented by R 13 and R 14 include aryl having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1.
  • Examples include groups exemplified as the group, Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 13 and R 14 include those having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 .
  • Groups exemplified as arylalkyl groups Examples of the halogen atom which may be substituted for the alkyl group, aryl group and arylalkyl group represented by R 13 and R 14 include halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 And the groups exemplified as above.
  • the groups groups satisfying a predetermined carbon number, etc.
  • R 21 A phenyl group represented by R 21 and an alkoxy group having 1 to 10 carbon atoms which may be substituted with a cycloalkyl group having 3 to 10 carbon atoms
  • an alkoxy group having 1 to 10 carbon atoms represented by R 22 As the groups exemplified as the benzene ring, naphthalene ring and anthracene represented by A, the alkoxy group having 1 to 8 carbon atoms and the alkoxy group having 1 to 8 carbon atoms represented by R 5 Etc.
  • Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 21 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like, and these groups are the above alkyl groups having 1 to 10 carbon atoms or carbon atoms. And a group substituted with an alkoxy group having 1 to 10 atoms.
  • Examples of the alkenyl group having 2 to 10 carbon atoms represented by R 22 include vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl and the like.
  • Examples of the halogen atom represented by R 22 and the halogen atom that may substitute the alkyl group, alkoxy group and alkenyl group represented by R 21 and R 22 include R 01 , R 02 , R 03 , R 04 and group exemplified as the halogen atom represented by R 05 can be mentioned.
  • the substitution position of the halogen atom that may substitute the alkyl group, alkoxy group and alkenyl group represented by R 22 is not limited.
  • Examples of the aryl group having 6 to 20 carbon atoms represented by R 23 and R 24 include aryl having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1.
  • Examples include groups exemplified as the group, Examples of the aryloxy group having 6 to 20 carbon atoms represented by R 23 and R 24 include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4-vinylphenyl 2-oxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hexylphenyloxy, 4-cyclohexylphenyloxy, 4-octylphenyl Oxy, 4- (2-ethylhexyl) phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2.6-dimethylphenyloxy, 3.4-dimethylphenyl Oxy, 3.5-dimethylphenyloxy, 2 4-di-tert-buty
  • the oxygen atom of the aryloxy group having 6 to 20 carbon atoms which may be substituted with the above halogen atom is substituted with a sulfur atom.
  • the oxygen atom of the aryloxy group having 6 to 20 carbon atoms which may be substituted with the above halogen atom may be vinyl, allyl, Groups substituted with alkenyl groups such as 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl and the like,
  • Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 23 and R 24 include those having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 .
  • heterocyclic group containing 2 to 20 carbon atoms represented by R 23 and R 24 examples include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene. And groups such as thiofuran and groups in which these groups are substituted with a halogen atom.
  • halogen atom that may be substituted for the alkyl group, aryl group, aryloxy group, arylthio group, arylalkenyl group, arylalkyl group, and heterocyclic group represented by R 13 and R 14 include R 01 , R The groups exemplified as the halogen atoms represented by 02 , R 03 , R 04 and R 05 can be mentioned.
  • Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 2 in the general formula (4) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3). Are trivalent groups substituted with Z 1 , Z 2 and Z 3 , and the methylene group in the aliphatic hydrocarbon group is —O—, —S—, —CO—, —CO—O.
  • —, —O—CO—, —SO 2 —, —NH—, or a combination thereof may be replaced by, for example, —COO—O—, —COO—S—, —O—OCO—, —S—OCO—, —CO—NH—, —NH—CO—, etc., among others, —COO—, —O—, —OCO—, —NHCO—, —NH—, — CONH -, - O-CONH- or preferably one is replaced with -NHCO-O-, trivalent represented by X 2
  • the alicyclic hydrocarbon group having a carbon number of 3 to 35, an alicyclic hydrocarbon groups exemplified in the description of X 1 in the general formula (3) is substituted with Z 1, Z 2 and Z 3 Trivalent groups, etc.
  • the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1
  • trivalent groups substituted with Z 2 and Z 3 etc.
  • Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by X 2 include the heterocyclic group exemplified in the description of X 1 in the general formula (3), Z 1 , Z 2 and Z And trivalent groups substituted with 3 .
  • the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 20 carbon atoms, or the arylalkyl group having 7 to 20 carbon atoms represented by R 25 is represented by R 13 and R 14. Examples thereof include a group similar to an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.
  • Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 3 in the general formula (5) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3). Include tetravalent groups substituted with Z 1 , Z 2 , Z 3 and Z 4 , and the methylene group in the aliphatic hydrocarbon group includes —O—, —S—, —CO—, — COO—, —OCO—, —NH— or a combination thereof may be substituted, and examples of the combination thereof include, for example, —COO—O—, —COO—S—, —O—OCO— , —S—OCO—, —CO—NH—, —NH—CO— and the like, among others, —COO—, —O—, —OCO—, —NHCO—, —NH—, —CONH—, —O Preferred are those substituted with —CON
  • Examples of the tetravalent C6-C35 aromatic ring-containing hydrocarbon group represented by X 3 include the aromatic ring-containing hydrocarbon groups exemplified in the description of X 1 in the general formula (3), Z 1 , And tetravalent groups substituted with Z 2 , Z 3 and Z 4 , etc.
  • the tetravalent C2-C35 heterocycle-containing group represented by X 3 the heterocycle-containing groups exemplified in the description of X 1 in the general formula (3) are Z 1 , Z 2 , Z And tetravalent groups substituted with 3 and Z 4 .
  • Examples of the aliphatic hydrocarbon group having 2 to 35 pentavalent carbon atoms represented by X 4 in the general formula (6) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3).
  • pentavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 and the methylene group in the aliphatic hydrocarbon group is —O—, —S—, —CO -, -CO-O-, -O-CO-, -SO 2- , -NH -Or a combination thereof may be replaced by, for example, -COO-O-, -COO-S-, -O-OCO-, -S-OCO-, -CO Represents —NH—, —NH—CO—, etc.
  • —COO—, —O—, —OCO—, —NHCO—, —NH—, —CONH—, —O—CONH— or —NHCO—O— Is preferably replaced with
  • the pentavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by X 4 the alicyclic hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And pentavalent groups substituted with Z 2 , Z 3 , Z 4 and Z 5 , etc.
  • the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1
  • the heterocyclic group exemplified in the description of X 1 in the general formula (12) is Z 1 , Z 2 , Z 3 , pentavalent groups substituted with Z 4 and Z 5 and the like.
  • Examples of the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by X 5 in the general formula (7) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3). Include hexavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , and the methylene group in the aliphatic hydrocarbon group includes —O—, —S— , —CO—, —COO—, —OCO—, —SO 2 —, —NH—, or a combination thereof may be substituted, for example, —COO—O—, —COO—S—, —O—OCO—, —S—OCO—, —CO—NH—, —NH—CO—, etc., among others, —COO—, —O—, —OCO—, —NHCO— , —NH—, —CONH—, —O—
  • the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1
  • the heterocyclic group exemplified in the description of X 1 in the general formula (3) is Z 1 , Z 2 , Z 3 , a hexavalent group substituted with Z 4 , Z 5 and Z 6 , and the like.
  • X 3 in formula (5) is a group selected from group 3; when m is 5, X is represented by the above general formula (6), and X 4 in formula (6) is A group selected from the following group 4; when m is 6, X is represented by the general formula (7), and X 5 in the formula (7) is a group selected from the following group 5: , Raw material acquisition and production It is preferable because it is easy to manufacture and has high heat resistance.
  • R 5 is the same group as R 5 in the general formula (1), and when there are two or more in the group, they may be the same or different, and p is an integer of 1 to 3) Q represents an integer of 0 to 3, and r represents an integer of 0 to 19.)
  • Specific examples of the compound represented by the general formula (1) include compounds represented by the following [Chemical Formula 16] to [Chemical Formula 18], but the present invention is not limited to these compounds.
  • R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 and R 42 are each independently a hydrogen atom or a halogen atom.
  • X 11 represents an oxygen atom or a sulfur atom
  • Y 11 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms
  • the alkyl group, aryl group or arylalkyl group represented by R 31 to R 42 and Y 11 is substituted with a halogen atom or unsubstituted, R 32 and R 43 , R 33 and R 44 , R 36 and R 45 , R 37 and R 46 , R 40 and R 47 , R 41 and R 48 , R 31 and R 32 , R 33 and R 34 , R 35 And R 36 , R
  • R 43 , R 44 , R 45 , R 46 , R 47 and R 48 each independently represents an alkyl group having 1 to 8 carbon atoms, a phenyl group or a benzyl group
  • the alkyl group represented by R 43 to R 48 is substituted or unsubstituted with a hydroxyl group, a halogen atom, a cyano group or a nitro group
  • the phenyl group and benzyl group represented by R 43 to R 48 are substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group, or a vinyl group
  • R 43 and R 44 , R 45 and R 46 , and R 47 and R 48 may be linked to form a 3- to 6-membered ring
  • An q ⁇ represents a q-valent anion
  • q represents 1 or 2
  • p represents a coefficient for maintaining a neutral charge
  • Examples of the halogen atom that may substitute the alkyl group, phenyl group, and benzyl group represented by R 43 to R 48 are the halogen atoms represented by R 01 , R 02 , R 03 , R 04, and R 05. Group.
  • groups include R 01 , R 02 , R 03 , R 04 and R 05 and groups satisfying a predetermined carbon number among the groups exemplified as alkyl groups having 1 to 40 carbon atoms represented by R 1.
  • Examples of the aryl group having 6 to 12 carbon atoms represented by R 31 to R 42 and Y 11 include R 01 , R 02 , R 03 , R 04 and R 05 and 6 to 6 carbon atoms represented by R 1.
  • arylalkyl group having 7 to 20 carbon atoms represented by R 31 to R 42 and Y 11 examples include 7 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1.
  • R 32 and R 43, R 33 and R 44, R 36 and R 45, R 37 and R 46, R 40 and R 47, R 41 and R 48, R 31 and R 32, R 33 and R 34, R 35 And R 36 , R 37 and R 38 , R 39 and R 40, and R 41 and R 42 may be linked to form a 6-membered ring such as a piperidine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, or a julolidine ring. Ring, etc.
  • R 31 and R 42 , R 34 and R 35 and R 38 and R 39 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 49 R 50 , CO, NR 51 , PR 52 or SO 2.
  • the ring that can be formed include a dihydroanthracene ring, an acridine ring, a xanthene ring, and a thioxanthene ring.
  • Examples of the 3- to 6-membered heterocyclic ring that can be formed by linking R 43 and R 44 , R 45 and R 46 , and R 47 and R 48 include a piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiol Morpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, isothiazolidine ring, and the like. It may be condensed with a ring or may be substituted.
  • examples of the anion represented by An q- include monovalent ions such as chloride ions, bromide ions, iodide ions, fluoride ions, and the like; perchlorine Inorganic anions such as acid ion, chlorate ion, thiocyanate ion, hexafluorophosphate ion, hexafluoroantimonate ion, tetrafluoroborate ion; methanesulfonate ion, dodecylsulfonate ion, benzenesulfonate ion, Toluenesulfonate ion, trifluoromethanesulfonate ion, naphthalenesulfonate ion, diphenylamine-4-sulfonate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-amino-5-nitro
  • Organic sulfonate anions such as sulfonate ions; octyl phosphate ions, dodecyl phosphate ions, octadecyl phosphate ions, phenyl phosphate ions, nonylphenyl phosphate ions, 2,2′-methylenebis (4,6- Di-t-butylphenyl) phosphonic acid
  • Organic phosphate anions such as ON, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4-ethylcyclohexanesulfonate ion, tetrakis (pentafluorophenyl) borate ion, tris (fluoroalkyl) Sulfonyl) carbanion and the like
  • examples of the divalent include benzene disulfonate ion, naphthalenedisulfonate
  • quencher anions that have the function of deexciting (quenching) active molecules in the excited state
  • ferrocenes having an anionic group such as a carboxyl group, phosphonic acid group, or sulfonic acid group on the cyclopentadienyl ring.
  • Metallocene compound anions such as luteocene can also be used as necessary.
  • p is selected so that the charge is neutral throughout the molecule.
  • the anion represented by An q- may have 1 to 10 substituents represented by the general formula (1).
  • Examples include anions represented by the following [Chemical 19A], but the present invention is not limited to these anions.
  • quencher anion examples include, for example, JP-A-60-234892, JP-A-5-43814, JP-A-5-305770, JP-A-6-239028, JP-A-9-309886.
  • Examples of the anion represented by An q- in the general formula (I) include a monovalent organic sulfonic acid anion, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4- Ethylcyclohexanesulfonate ion, benzenedisulfonate ion, and naphthalenedisulfonate ion are preferable from the viewpoint of heat resistance, and bistrifluoromethylsulfonylimide ion is more preferable.
  • D represents a group selected from (a) to (m) of the following group I
  • D ′ represents a group selected from (a ′) to (m ′) of the following group II
  • Q represents a methine chain having 1 to 9 carbon atoms, and represents a linking group that may contain a ring structure in the chain.
  • the hydrogen atom in the methine chain is a hydroxyl group, a halogen atom, a cyano group, —NR 51 R 52 , An aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or an alkyl group having 1 to 8 carbon atoms, the —NR 51 R 52 , aryl group, aryl
  • the alkyl group and the alkyl group may be further substituted with a hydroxyl group, a halogen atom, a cyano group, or —NR 51 R 52.
  • —NR 51 R 52 an aryl group, an arylalkyl group, and a methylene group in the alkyl group are Replaced by —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH—.
  • R 51 and R 52 represent an aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or an alkyl group having 1 to 8 carbon atoms
  • An q ⁇ represents a q-valent anion
  • q represents 1 or 2
  • p represents a coefficient for maintaining a neutral charge
  • It has at least one substituent represented by the general formula (1) in the molecule.
  • D represents a group selected from groups (a) to (m) of the following group I
  • D ′ represents a group selected from groups (a ′) to (m ′) of the following group II: .
  • R 53 and R 53 ′ are a hydroxyl group, a halogen atom, a nitro group, a cyano group, —SO 3 H, a carboxyl group, an amino group, an amide group, a ferrocenyl group, an aryl group having 6 to 30 carbon atoms, or a carbon atom number of 7 Represents an arylalkyl group of ⁇ 30 or an alkyl group of 1 to 8 carbon atoms,
  • the aryl group, arylalkyl group and alkyl group represented by R 53 and R 53 ′ are substituted with a hydroxyl group, a halogen atom, a nitro group, a cyano group, —SO 3 H, a carboxyl group, an amino group, an amide group or
  • the aryl group represented by R 53 and R 53 ′, the arylalkyl group and the methylene group in the alkyl group are —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— may be substituted, and R 54 to R 61 and R 54 ′ to R 61 ′ are R 53 and R 53 Represents the same group or hydrogen atom as X 12 , X 12 ′, X 13 and X 13 ′ are an oxygen atom, a sulfur atom, a selenium atom, —CR 62 R 63 —, a cycloalkane-1,1-diyl group having 3 to 6 carbon atoms, —NH - or -NY 13 - represents, R 62 and R 63 represent the same group or a hydrogen atom and R 53 and
  • the alkyl group represented by Y 12 , Y 12 ′ and Y 13 , the aryl group and the methylene group in the arylalkyl group are —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— may be substituted, r and r ′ are 0 or (a) to (e), (g) to (j), (l), (m), (a ′) to (e ′), (g ′) to (j ′) ), (L ′) and (m ′) represent the number that can be substituted. )
  • Q constitutes a methine chain having 1 to 9 carbon atoms
  • examples of the linking group that may include a ring structure in the chain include the following (Q-1) to (Q-11):
  • a group represented by any one is preferable because it is easy to produce.
  • the number of carbon atoms in the methine chain having 1 to 9 carbon atoms represents a methine chain and a linking group that may contain a ring structure in the chain, and a group that further substitutes the linking group (for example, R 62 to R 67 below, Z ′) carbon atoms (for example, carbon atoms at both ends in the linking group (Q-1)) are not included.
  • R 62 , R 63 , R 64 , R 65 , R 66 , R 67 and Z ′ each independently represents a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, —NRR ′, a carbon atom number of 6 to 12 represents an aryl group, an arylalkyl group having 7 to 12 carbon atoms or an alkyl having 1 to 8 carbon atoms; —NRR ′, aryl group, arylalkyl group and alkyl group represented by R 62 to R 67 and Z ′ may be substituted with a hydroxyl group, a halogen atom, a cyano group or —NRR ′, and —O—, Even when interrupted by —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH
  • Examples of the halogen atom represented by R 62 to R 67 and Z ′ include groups exemplified as the halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 .
  • the aryl group having 6 to 12 carbon atoms represented by R 62 to R 67 , Z ′, R and R ′ is represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 .
  • Examples of the arylalkyl group having 7 to 12 carbon atoms represented by R 62 to R 67 , Z ′, R and R ′ include R 01 , R 02 , R 03 , R 04 and R 05 and R 1 .
  • groups that satisfy a predetermined number of carbons, and the like can be given.
  • An as the anion represented by q-, etc. exemplified groups as an anion represented by An q- in the general formula (8) below.
  • Two Ds in the general formula (10) and D and D ′ in the general formulas (11) and (12) are one nonionic group and one cationic group so that the charge becomes neutral as a compound.
  • the halogen atom represented by R 53 to R 63 and R 53 ′ to R 63 ′ in the general formulas (10) to (12), the aryl group, arylalkyl group and alkyl group represented by R 53 and R 53 ′ As the halogen atom that may be substituted, and the halogen atom that may be substituted for the alkyl group, aryl group, and arylalkyl group represented by Y 12 , Y 12 ′, and Y 13 , R 01 , R 02 , R
  • the group illustrated as a halogen atom represented by 03 , R04, and R05 is mentioned.
  • Examples of the aryl group having 6 to 30 carbon atoms represented by R 53 to R 63 and R 53 ′ to R 63 ′ and Y 12 , Y 12 ′ and Y 13 include phenyl, naphthyl, 2-methylphenyl, 3- Methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6- Dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl,
  • Examples of the arylalkyl group having 7 to 30 carbon atoms represented by R 53 to R 63 and R 53 ′ to R 63 ′ and Y 12 , Y 12 ′ and Y 13 include benzyl, phenethyl, 2-phenylpropane-2 -Yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, ferrocenylmethyl, ferrocenylpropyl and the like, An alkyl group having 1 to 8 carbon atoms represented by R 53 to R 63 and R 53 ′ to R 63 ′, and an alkyl group having 1 to 20 carbon atoms represented by Y 12 , Y 12 ′ and Y 13 As R 01 , R 02 , R 03 , R 04 and R 05 and groups exemplified as alkyl groups having 1 to 40 carbon atoms represented by R 1 , groups satisfying a predetermined carbon number, etc. may be mentioned. It is done.
  • the cycloalkane-1,1-diyl group having 3 to 6 carbon atoms represented by X 12 , X 12 ′, X 13 and X 13 ′ is cyclopropane. -1,1-diyl, cyclobutane-1,1-diyl, 2,4-dimethylcyclobutane-1,1-diyl, 3,3-dimethylcyclobutane-1,1-diyl, cyclopentane-1,1-diyl, And cyclohexane-1,1-diyl.
  • the method for producing the compound of the present invention which is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region and having at least one structure represented by the general formula (1) in the molecule.
  • a cyanostyrene compound, a triarylmethane compound, and a cyanine compound are produced by a known method as an organic dye having an absorption maximum in a wavelength region from ultraviolet to near infrared, and then, an acid chloride and a Boc reagent are added thereto.
  • Alkyl halide compounds, silyl chloride compounds, allyl ether compounds, and the like and a method obtained by introducing the structure represented by the general formula (1).
  • the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention and having at least one structure represented by the general formula (1) in the molecule will be described below as a dye.
  • a dye In addition to colored photosensitive compositions, optical filters used in displays and optical lenses, silver halide photographic photosensitive materials, dyed articles, paints, inks, electrophotographic photoreceptors, toners, thermal recording paper, transfer ribbons, optical recording dyes , Solar cells, organic semiconductors, clinical laboratory reagents, laser therapeutic dyes, dyeing, etc.
  • a thermosetting composition or a polymerizable composition as an antioxidant it is also used as a color developer in a heat-sensitive material.
  • the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention and having at least one structure represented by the following general formula (1) in the molecule is the above general formula (1).
  • R 1 is not a hydrogen atom, it can also be used as a latent additive.
  • the latent additive is inactive in a pre-bake process at room temperature or 150 ° C., and the protective group is formed by heating at 100 to 250 ° C. or heating at 80 to 200 ° C. in the presence of an acid / base catalyst.
  • latent resin additives such as latent antioxidants and latent UV absorbers; latent developer for thermal paper; latent storage stability for thermal paper Agents; latent curing agents and the like.
  • the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention comprising a compound having at least one structure represented by the general formula (1) in the molecule Will be described.
  • the composition containing an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention and having at least one structure represented by the general formula (1) in the molecule is colored.
  • it is also used as a polymerizable composition.
  • the colored photosensitive composition it is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention, and has at least one structure represented by the general formula (1) in the molecule.
  • the content of the compound is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass.
  • the colored photosensitive composition is cured by light irradiation, and may be any of photocation curable, photoanion curable, or photo radical curable, but is preferably a photo radical curable.
  • the colored photosensitive composition is photo-radical curable
  • the colored photosensitive composition is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region according to the present invention.
  • a polymerizable compound having an ethylenically unsaturated bond having an acid value and a radical photopolymerization initiator are essential components.
  • this colored photosensitive composition is also referred to as a colored photosensitive composition of the present invention.
  • Examples of the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, and isocrotonic acid.
  • X 41 is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO— or a substituent represented by the above (3-1) to (3-3), wherein the alkylidene group may be substituted with a halogen atom
  • R 68 , R 69 , R 70 and R 71 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.
  • a halogen atom and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and s is an integer of 0 to 10.
  • polymerizable compounds can be used alone or in combination of two or more, and can be used in combination with a polymerizable compound having an ethylenically unsaturated bond having no acid value. When two or more kinds are mixed and used, they may be copolymerized in advance and used as a copolymer.
  • Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, The following compound No. A1-No.
  • A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
  • a monofunctional or polyfunctional epoxy compound may be used together with the polymerizable compound having an ethylenically unsaturated bond having the acid value. It can.
  • the polymerizable compound having an ethylenically unsaturated bond having an acid value preferably has a solid content acid value of 5 to 120 mgKOH / g, and the amount of the monofunctional or polyfunctional epoxy compound used is It is preferable to select so as to satisfy the value.
  • Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
  • the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a colored photosensitive composition with better characteristics can be obtained.
  • the bisphenol type epoxy compound an epoxy compound represented by the general formula (13) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used.
  • glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
  • novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
  • the content of the polymerizable compound having an ethylenically unsaturated bond having an acid value is 1 to 95% by mass, particularly 10 to 80% in the colored photosensitive composition of the present invention. Mass% is preferred.
  • the content is with respect to 100 mass parts of polymeric compounds which have the ethylenically unsaturated bond which has the said acid value, The amount is preferably 10 to 1000 parts by mass.
  • the photo radical polymerization initiator may be any compound that can initiate radical polymerization upon receiving light irradiation, such as acetophenone compounds, benzyl compounds, benzophenone compounds, oxime compounds, thioxanthone compounds, for example.
  • acetophenone compounds such as acetophenone compounds, benzyl compounds, benzophenone compounds, oxime compounds, thioxanthone compounds, for example.
  • preferable compounds include ketone compounds such as compounds.
  • acetophenone compound examples include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl- 2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azidoben Salacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) ) -Butanone-1, Ben Zoin, benzoin methyl ether, benzoin ethyl ether, benzoin is
  • benzylic compound examples include benzyl and anisyl.
  • benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like. It is done.
  • oxime compounds examples include 1.2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2-methylbenzoyl).
  • thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
  • radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1-yl)] titanium Etc.
  • photo radical polymerization initiators can be used alone or in combination of two or more according to the desired performance.
  • the radical photopolymerization initiator as described above is a radical polymerizable organic substance (polymerizable compound having an ethylenically unsaturated bond having an acid value, polymerizable compound having an ethylenically unsaturated bond having no acid value, a single compound,
  • the stoichiometrically required amount may be used for the functional or polyfunctional epoxy compound), preferably 0.05 to 10 parts by weight, more preferably 0.1 to 10 parts by weight with respect to the radical polymerizable organic substance. It is better to mix part. If this range is exceeded, a cured product having sufficient strength may not be obtained, and if it is less than this range, the resin may not be sufficiently cured.
  • the content of the photo radical polymerization initiator in the colored photosensitive composition of the present invention is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass.
  • the content of the photopolymerization initiator is less than 0.1% by mass, curing by exposure may be insufficient.
  • the content is more than 30% by mass, the initiator is precipitated in the colored photosensitive composition. There is.
  • the colored photosensitive composition of the present invention is dissolved or dispersed in an organic solvent as necessary, and the obtained coating liquid is spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, etc. It can be applied on a supporting substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. by a known means and cured by light irradiation.
  • the organic solvent is usually a solvent that can dissolve or disperse each of the above components as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone.
  • Ketones such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether, etc .; methyl acetate, ethyl acetate, acetic acid-n-propyl, acetic acid Ester solvents such as isopropyl, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolv solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Alcohol solvents such as diol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (
  • solvents can be used as one or a mixture of two or more.
  • ketones, ether ester solvents and the like particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because of good compatibility between the resist and the photopolymerization initiator in the colored photosensitive composition.
  • a colorant can be further added to the colored photosensitive composition of the present invention, and examples of the colorant include dyes and pigments.
  • the dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm.
  • inorganic pigments or organic pigments can be used, for example, nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, Isoindoline compounds, quinacridone compounds, anthanthrone compounds, perinone compounds, perylene compounds, diketopyrrolopyrrole compounds, thioindigo compounds, dioxazine compounds, triphenylmethane compounds, quinophthalone compounds, naphthalene tetracarboxylic acids; azo dyes, metal complex compounds of cyanine dyes Lake pigments; carbon black obtained by furnace method, channel method, thermal method, acetylene black, ketjen black or lamp black, etc.
  • Carbon black prepared by coating and coating the above-described carbon black with an epoxy resin, dispersed in a solvent in advance with the above-described carbon black and adsorbed with 20 to 200 mg / g of resin, and the above-described carbon black being acidic or alkaline Surface treatment, average particle diameter of 8 nm or more, DBP oil absorption of 90 ml / 100 g or less, total oxygen amount calculated from CO and CO 2 in volatile matter at 950 ° C.
  • inorganic pigment or organic pigment commercially available pigments can also be used.
  • the content of the colorant is preferably 0 to 99% by mass, particularly preferably 0 to 80% by mass in the colored photosensitive composition of the present invention.
  • the colored photosensitive composition of the present invention can further contain an inorganic compound.
  • the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Etc.
  • a dispersant can be added.
  • any pigment or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie, Inc. can be used.
  • Polymer dispersant made of ether or polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom being an amine and / or a quaternary salt thereof, having an amine value of 1 to 100 mgKOH / g Are preferably used.
  • a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as cross-linking agents; thickeners can be added.
  • a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • plasticizer adhesion promoter
  • filler Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as cross-link
  • the properties of the cured product of the colored photosensitive composition of the present invention can be improved.
  • the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
  • Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
  • polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
  • a thermal radical polymerization initiator a chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound and the like can be used in combination.
  • thermal radical polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (methylisobutylate), 2,2′-azobis-2,4-dimethylvaleronitrile, Azo initiators such as 1′-azobis (1-acetoxy-1-phenylethane); benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate, di (4-t-butylcyclohexyl) )
  • Peroxide initiators such as peroxydicarbonate, and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.
  • a sulfur atom-containing compound is generally used.
  • Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
  • the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
  • fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
  • anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
  • silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having an isocyanate group, a methacryloyl group, and an epoxy group. A ring agent is preferably used.
  • Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
  • the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed.
  • an oligomer component may be formed.
  • hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
  • alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
  • the active light source used for curing the colored photosensitive composition of the present invention one that emits light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, Carbon arc, xenon arc, etc. can be used.
  • the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
  • the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
  • the colored photosensitive composition of the present invention (or a cured product thereof) is a photocurable paint or varnish, a photocurable adhesive, a printed circuit board, a color television, a PC monitor, a personal digital assistant, a digital camera, or the like.
  • the colored photosensitive composition of the present invention is used for the purpose of forming pixels of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel. is there.
  • the color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition on a substrate, and (2) irradiating the coating film with active light through a mask having a predetermined pattern shape. It is preferably formed by a step, (3) a step of developing the film after exposure with a developer, and (4) a step of heating the film after development.
  • the colored photosensitive composition of the present invention is also useful as an inkjet-type colored photosensitive composition without a development step.
  • Step 2> Compound No. Synthesis of 2 1 equivalent of compound 7, 10 g of ethyl acetate and 10 g of water were mixed, 1 equivalent of compound 6 obtained in step 1 was added and stirred, and then the ethyl acetate layer was separated and dried to obtain a theoretical yield of 5 Concentrated to double. The concentrated ethyl acetate solution was dispersed in hexane and crystallized. 2 was obtained with a yield of 70%. It was confirmed by 1 H-NMR and IR that the obtained compound was the desired product. Moreover, the absorption wavelength characteristic was measured. The results are shown in [Table 1] and [Table 2].
  • Step 2 Compound No. 3
  • a toluene solution containing 1 equivalent of the compound 9 obtained in Step 1 4 g of chloroform and 1 eq.
  • the mixture was stirred and oil-water separated, then dispersed in hexane and crystallized. 3 was obtained in 80% yield. It was confirmed by 1 H-NMR and IR that the obtained compound was the desired product. Moreover, the absorption wavelength characteristic was measured. The results are shown in [Table 1] and [Table 2].
  • Comparative coloring photosensitive composition No. 1-No. Preparation of Compound No. 3 in Step 2 of Example 2 1 was compared with the following comparative compound No. 1. 1-No. Except for the change to any of No. 3, the comparative colored photosensitive composition No. 1 was prepared in the same manner as in Example 2-1. 1-No. 3 was obtained.
  • Comparative coloring photosensitive composition No. 1A-No. 3 Comparative coloring photosensitive composition No. 1-No. 3 was added in the same manner as in Example 2-1, except that the following compound ⁇ was added as an antioxidant. 1A-No. 3A was obtained.
  • the colored photosensitive composition of the present invention has high heat resistance.
  • the colored photosensitive composition No. 1-No. 3 shows comparative compound no.
  • the colored photosensitive composition No. 1 was prepared in the same manner as in Example 2-1, except that 1 was added. 1A-No. 3A was obtained respectively.
  • 1A-No. 3A was coated on a glass substrate under the condition of 410 rpm ⁇ 7 sec, and dried on a hot plate (90 ° C., 90 sec). The obtained coating film was exposed (150 mJ / cm 2 ) with an ultrahigh pressure mercury lamp.
  • the coated film after exposure was baked under conditions of 230 ° C. ⁇ 30 min.
  • the absorbance of the coating film before baking (after exposure) and the absorbance of the coating film after baking at the maximum absorption wavelength ( ⁇ max) of the compound used are measured, and the absorbance of the coating film before baking (after exposure) is 100 was evaluated as relative strength. Further, the color difference ( ⁇ E ab * ) before and after firing was examined. The results are shown in [Table 4].
  • the colored photosensitive composition obtained by adding the compound of the present invention to the conventional dye has higher heat resistance than the comparative colored photosensitive composition obtained by adding the antioxidant to the conventional dye. . Therefore, this shows that the compound of the present invention has a high antioxidant function.
  • the colored photosensitive composition using the novel compound of the present invention and its cured product have high heat resistance. Therefore, the dye and the colored photosensitive composition of the present invention are useful for a color filter for a display device and a liquid crystal display panel using the same.

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WO2017146897A1 (en) * 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
KR20170126690A (ko) * 2016-05-10 2017-11-20 주식회사 엘지화학 화합물, 이를 포함하는 색재 조성물 및 이를 포함하는 수지 조성물
US10377961B2 (en) 2016-02-26 2019-08-13 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
KR102064631B1 (ko) * 2015-06-30 2020-01-09 주식회사 엘지화학 아민계 화합물, 이를 포함하는 색재 조성물 및 이를 포함하는 수지 조성물
US20210017410A1 (en) * 2018-03-30 2021-01-21 Taiyo Ink Mfg. Co., Ltd. Curable composition for inkjet, cured product of same, and electronic component comprising said cured product

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KR102092439B1 (ko) * 2016-07-26 2020-03-23 주식회사 엘지화학 감광성 수지 조성물 및 이를 포함하는 컬러필터
CN110869343A (zh) * 2017-10-05 2020-03-06 株式会社艾迪科 化合物、潜伏性抗氧化剂、组合物、固化物及固化物的制造方法

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